A Woman Reborn

A Woman Reborn

A lighthearted and fanciful story of a downtrodden middle-aged woman embarking on a journey of sexual discovery.

Chapter 1 - An Unexpected Friend

Jane sat in a cramped bathroom cubicle at work trying to keep her crying as quiet as possible.

It had been an almost impossibly stressful year. The start of it had been finding out that her husband of twenty-six years had been cheating on her for several of those years. Worse, he hadn't even attempted to try and salvage their marriage, suggesting instead that they get divorced. The bastard had even told her that it should be her that divorced him, as she had the more legitimate reason.

The suggestion had seemed reasonable at the time, but later she had wondered if he just didn't want the hassle of having to fill out all the paperwork himself.

John had left two weeks later. He didn't tell her where he was staying and she didn't ask. It was a week after he had left that she had gotten a call from a moving company to arrange a date for them to pick up John's belongings. She was incredulous at the fact he was actually expecting her to sort through his stuff and presumably box it up for him as well?

For a few days after hearing that John expected her to do his packing, the mounting sense of despair that she had been feeling was briefly eclipsed by an angry sense of injustice. It was because of this anger that the day before the movers were due to arrive, she went through all of their shared belongings and sorted out John's stuff. However, instead of boxing it up like he expected her to do, she merely piled it up in a large mound at the end of the front lawn.

The following day as she left for work in the rain, she smiled briefly as she drove past the soggy pile of his belongings. It might have been petty of her, but this small token of revenge felt justified.

When she got home that evening she was surprised to see John's pile of belongings was still at the end of the lawn. Either the movers hadn't turned up or they hadn't wanted to have to deal with loose items. But she tried to tell herself, it was John's problem, not hers.

When she left for work the next morning she tried not to look at the sad pile of belongings.

To her relief, it was gone by the time she returned that evening.

Her sense of relief didn't last long though. Even though she hadn't gotten around to starting the divorce proceedings yet, on the doorstep was a letter from a lawyer John had employed. The letter merely let her know that the only thing John wanted in the settlement was half the value of the house.

Jane felt crushed. There would be no way that she could buy John out, which meant she would have to sell the house and find somewhere else to live.

Now, almost a year to the day that she had received her first letter from John's lawyer, the final decree for her divorce had arrived in this morning's post.

She had thought that receiving the final decree would be a relief, but instead it felt as though everything that represented her entire adult life up until this point had just been made irrelevant.

The simple paper form had just informed her that that period of her life was now over.

So, what was she meant to do now?

That simple question had scared her badly when she had first asked it of herself.

It was probably the thousandth time she had asked herself that question since John had left, and so far she hadn't been able to come up with a good answer.

When she had married John at the age of eighteen, he had been the only man she had ever been with and for better or worse, she had been faithful to him for the entire twenty-six years.

One of the most frightening things that kept coming back to her was, did this mean she was now destined to spend the remainder of her life alone? She felt that it was too late to start over again and wasn't sure if she had the strength to try, or even wanted to.

It was thinking about the futility of her life and the deep injustice that consumed her that had led her to find solitude in this bathroom stall.

Eventually, once most of the hurt of her current situation had worked itself out of her system, she managed to stop her mostly silent crying. Dabbing her face with her hankey, she tried to make herself a little more presentable whilst at the same time listening to make sure she was still alone in the bathroom.

Finally, having gotten herself back under control, she unlatched the cubicle door and stepped out into the empty bathroom.

Except it wasn't empty.

Kim from accounting was standing by the hand basins and watching her with a mixture of concern and embarrassment.

"I'm sorry, I didn't want to pry, but I thought I heard somebody crying and I just wanted to make sure you were OK."

Jane had never really had occasion to speak to Kim before as they moved in different circles. Kim was a popular and outgoing woman... and well, Jane just wasn't. Also, even though Kim was the same age as her, maybe even a year or two older, she had a reputation for going out with several different men, many of them younger than her. She wasn't the sort of person Jane would normally associate herself with.

However, the honest concern that she had heard in Kim's voice was touching in its sincerity, to the point that it nearly started her crying again.

"I'm fine, thank you. I just need to get a bit of cold water on my face" she said hesitantly walking towards the wash hand basins.

"If you want to talk about it, I'm willing to listen. I'm not sure if I can help, but it's often better to talk." Kim was looking even more embarrassed now, but she had made the offer anyway.

"No, it's OK. I'll be OK... but thanks for asking."

Becoming increasingly embarrassed herself, Jane quickly tidied herself up in the mirror before making a quick exit, pausing at the door to thank Kim again for her concern.

For the rest of the day, if anybody else noticed that she was still upset, nobody mentioned it.

*******

That evening Jane went back to her two-bedroom apartment, and although it had been advertised as "compact", which was usually a euphemism for "cramped", it still felt too large for just one person.

She had attempted to make it more homely since moving in two months ago, but no amount of redecorating could convince her that it was her "home", especially not after living so many years in the same house with John.

She just felt so cut off from everything that had anchored her to what was normal.

Her husband had gone, her home had gone, and if she was honest, she was beginning to wonder if her own sense of self-worth was about to leave, if it hadn't gone already.

Her work was currently her only anchor, but whilst it fulfilled her on a professional level, it no longer satisfied her personally. It wasn't a replacement for the other things she had lost in her life.

Jane was an engineer in an aerospace development company called Commsnet. The company designed and constructed satellites for an ever growing list of clients as space became the new business frontier. Her specialty was structural integrity, basically balancing the competing goals of structural strength against minimizing weight. She was good at her job and never made a fuss, in fact, that seemed to be the motto of her life. She never spoke up in work meetings, just as she had never complained about John's indifference to her for all those years.

She ended up going to bed early. There wasn't really anything to stay up for.

******

The next day Jane sat alone at her desk. She had tried to focus on her work, mainly as a means of trying to block everything else out, but the constant thoughts about how much she had lost and how little she had to look forward to kept returning to distract her. She was so distracted that it took a while to realize that the woman from yesterday, Kim, was stood in front of her desk.

"I said, I was just checking to see if you felt better today?" By the tone of it, Kim had apparently already asked her once before, but Jane had been so caught up in her own little bubble that she hadn't heard.

"Um, yes, I'm OK. Thanks." She didn't really feel OK, but it was just the polite thing to say when you didn't want to bother other people.

"OK. So, I'm heading out for lunch, do you want to join me? I know this quiet little place nearby which makes a mean panini."

Jane politely declined the offer, she wasn't really in the mood to socialize.

But Kim seemed undeterred. "Look, if you come to lunch, you won't need to talk, I'm more than capable of talking enough for both of us. I just thought it might do you some good to get out instead of moping around the office."

Jane was about to deny that she was "moping", until she realized that was exactly what she was doing.

Afterwards she wouldn't be able to remember why she had decided to go with Kim that day, but it turned out to be a decision that would end up changing the course of her life.

******

Sat in the small eatery, Jane sat in silence as Kim, true to her word, managed to talk for both of them. Jane wasn't really listening to her, it was just comforting to feel part of a conversation with another person, even if she wasn't really contributing to it.

The food arrived and the one-sided conversation briefly fell off as both women ate their lunch.

Eventually the silence was broken by Kim, who was now looking more serious.

"So, do you want to talk about what was upsetting you yesterday?"

Jane had the sense the question wasn't intended to pry, instead it appeared to be asked in kindness and concern. And all of a sudden, Jane did want to talk about it, in fact for the next half an hour the story gushed out of her like stagnant water being flushed from dammed river after the dam had been broken.

She told of how her life hadn't been good for years, she told of her hurt at finding out that John had been unfaithful to her and how the hurt had gotten even worse when he left her. She finished by saying that she didn't know what she was going to do now. Life seemed so grey and meaningless, she couldn't remember the last time she had been truly happy, and didn't see that changing any time soon.

In the silence that followed Jane's emotional confession, Kim seemed to be taking her time analyzing everything she had been told, before finally delivering her assessment:

"Your ex, John, he sounds like a real fucking asshole."

"No. John, he's..." Jane stopped herself. Automatically, without thinking, she had been about to defend John, just like she had done for most of their marriage. She sighed, "Yes, he's an asshole" she finished quietly, as if admittance of his bad behavior somehow reflected badly upon her.

"I... I just don't know what I'm going to do now" Jane admitted glumly.

"That's easy" said Kim brightly, "Anything you want to do. You just need to decide what you want."

"But that's the problem, I don't know what I want... apart from the fact that I don't want to be alone anymore."

Kim thought for a while, "Look, you've led a sheltered life, I get that... but if you want to move on, you have to be willing to make some changes. And if you don't want to be alone like you say, well that will mean you'll need to start dating again."

The thought of dating was the scariest thing Jane could possibly think of at the moment. Just the thought of it sat like a cold ball of ice in her stomach., "Your probably right," She admitted reluctantly. "But I don't know how. John was the only guy I've ever been with. I wouldn't even know how to start."

Kim looked at her with a mixture of puzzlement and concern, "When you say he was the only man you have been with, you just mean the only man you've had a long-term relationship with. Right?"

Jane seemed reluctant to answer, "No, I meant the only man I ever had... sex with. In fact, he was the only man I ever dated. We met at school."

"Oh dear god. You poor thing" exclaimed Kim, real sympathy evident in her voice.

Jane just sat quietly, embarrassed by Kim's reaction.

"Well, at least tell me he satisfied you in bed?" asked Kim, looking for any reason why a seemingly intelligent woman would stay with an asshole like John for so many years.

"No, not really" replied Jane quietly. She was beginning to feel a little uncomfortable with this line of questioning, but not as uncomfortable as her own answers were making her feel.

"But he at least..." even Kim now seemed to be having trouble with the topic. The two women had only known each other for a day, and even that wasn't under the best of circumstances, and here she was trying to come up with "polite" questions about the other woman's sex life. But at the same time she had become fascinated with what the answer might be.

"If you are about to ask if he ever gave me have an orgasm... the answer is No."

"But you have had an orgasm, haven't you?" Kim wasn't sure if she was more shocked or surprised that she was having to ask another woman this question.

Jane was quiet for a long time, "I don't think I have."

"Oh babe. If you're not sure, I can say with total certainty that you haven't" Then a shocking thought struck her, "Wait, not even by yourself? You must have seen to yourself at some point?"

"No, I don't do that."

"What? Why not?"

Jane was getting seriously embarrassed now. "Because I was always taught it was wrong." Jane didn't elaborate on the fact that when she was still in her teens, her mother had walked in on her one evening whilst she was exploring the feel of her body. The resulting lecture had stayed with her ever since.

Silence settled over the table again as the two women contemplated what had just been discussed.

Finally, it was Kim that broke the silence. "Well, we can definitely rule out dating for a while. You aren't remotely ready for that yet."

Despite how much the recent discussion on dating had scared and frightened her, Jane suddenly found herself defensive about the suggestion that she shouldn't do it, "Why not?"

"Because, in your current state, you're likely to fall head over heels in love with the first guy that shows you the minimum amount of affection."

"And what's so wrong in that?" asked Jane even more defensively.

"Because you are an attractive woman and whilst you have dubious judgement when it comes to men, you appear to be intelligent, sensitive and probably have a lot to offer. In other words, you are worth a damn sight more than just the minimum when it comes to guys."

Jane was slightly taken aback. Nobody had ever spoken to her like this before. Whilst she thought the comment about being attractive was an over exaggeration, it was unexpected for somebody to say nice things about her.

Seeing that Jane was thinking a lot about what had just been said, Kim steered the conversation back to less personal topics and instead chatted merrily about the benefits of different wines and the merits of the various collections that were coming into fashion this year.

But Jane wasn't really listening anymore. She had a lot to think about. In fact she spent the rest of the afternoon and the entire evening thinking about what had been said this lunchtime.

******

Chapter 2 - Homework

The next day when Kim came around to ask if she wanted to go for lunch, Jane was relieved as it saved her the effort of seeking out Kim to ask the same thing.

Waiting to be served in the deli, Kim started chatting away, just in case Jane just wanted some company again. But today Jane had a question.

"Yesterday you said I wasn't ready to begin dating. What do I need to do to get ready?"

Kim, paused, slightly caught out by the directness of Jane's question. She could see that the question was important to Jane, so took her time thinking about her reply.

"Look, I'm no expert... although I must admit to having some experience in this field," Kim had a self-deprecating smile as she looked at Jane, "But I'd say the best way of finding what you really want is to get comfortable with who you are first."

It wasn't quite the answer Jane had expected, so she still had questions.

"Isn't dating just about finding a man?"

"Not necessarily" replied Kim, "and even if that was what you were after, what type of man would you be looking for?"

Jane's immediate thought was any man that didn't make her feel alone anymore, but she suspected that answer wouldn't satisfy Kim. So, what sort of man did she want?

"I'm not sure" she finally admitted, "I don't really have much experience with men... except John of course."

"Exactly!" replied Kim, "That's why you don't just hitch yourself to the first man that comes along, and why you need to get experience of several men before you really know what you want."

"What! I can't do that. I'm not like..." Jane stopped herself, in her shock she had been about to say "like you" whilst looking directly at Kim and had just in time realized that it might have sounded bad.

But Kim smiled at her without any malice, "Like me, you mean?" Then she gave a good humored laugh, "Don't sweat it. I know what some people think of me and I honestly don't care. I'm not looking for a man... don't get me wrong, if Mr. Right comes along, then great, but in the meantime, the reason I go out with different men is simply because I enjoy sex."

Jane wasn't sure of what to think, the conversation certainly hadn't gone the way she thought it would. In the past she had always thought of "promiscuous" women as being "bad", but "bad" certainly wasn't a word that seemed to apply to Kim. OK, she didn't know Kim very well, but Kim was the only one that showed her compassion when she needed it, the only one to see if she was alright and was even now taking the time to give Jane advice. So, was she really in a position to judge Kim?

Her current thoughts were confusing, so she decided to move onto the other thing that Kim had said she would need to work on.

"What did you mean when I said that I would need to become comfortable with who I am? You mean more confident, right?"

"Um, partly, but what I mainly meant was becoming comfortable with your own body."

The response seemed to hang in the air as Jane began to suspect where Kim was going with this. But before she could voice her concern, Kim was speaking again.

"I know yesterday that you mentioned that you had never gotten yourself off, something I still find really bizarre, but have you ever taken the time to just explore your own body with your hands? Nothing sexual, just normal exploration, like a massage or a self-examination?"

"No" confessed Jane, such a thing had never even occurred to her before.

"So, do you want my advice?" asked Kim.

Jane nodded, afraid what the answer might be.

"OK, then I want you to go home tonight, I want you to pour yourself a drink... you like wine?" Jane nodded again, "Good, then pour yourself a large glass of wine then go and lay on your bed, naked. Shut your eyes, then just, let your hands explore your body. Nothing sexual, in fact try to avoid anything too stimulating, just explore and see how it feels."

"That's it? Just that?" asked Jane a bit relived. She had been worried Kim might have been about to suggest something more intimate.

"That's it" confirmed Kim. "If it makes it any easier for you, just think of it like getting a massage at a health spa" she finished with a grin.

Jane felt a sense of relief, this sound like something she could do. She wasn't really sure what the point of it was, but at least she felt she could do it without becoming too embarrassed.

"For a minute there I thought you were going to... you know... suggest I touch myself, "there"."

"Oh, that comes later" replied Kim, her grin even larger now, "but first we start with baby steps."

Even though she was a little nervous about Kim's last comment, a new question had just occurred to Jane.

"Kim... why are you doing this? Trying to help me I mean."

For a fraction of a second, a more serious expression flitted across Kim's face. Finally:

"At first, when I saw you were having a tough time of it, so, just common decency I suppose, I thought I could help, so I did. Later, after hearing your story, I realized that life had dealt you a pretty shitty hand and that you probably needed some help to get where you deserved to be."

"But you don't really know me" said Jane, not overlooking the fact that only Kim had shown any "common decency" towards her.

"So?" replied Kim matter-of-factly.

Still seeing some confusion in Jane's expression, Kim continued, "Look, in me you probably see a confident woman who does whatever she wants and says whatever she wants. Maybe I've always been like this, or maybe I haven't. Maybe in the past I was where you are now and needed somebody's help to pull myself up... maybe not. It doesn't matter. You look as though you could use a friend, and I'm willing to be that friend."

Jane couldn't believe that somebody as outgoing and as full of life as Kim was, could be anything like her. For a while she tried to find out more, to see if what Kim had hinted at might have been true, but Kim had managed to effortlessly deflect every question put to her. It was obvious that she didn't want to talk about that side of her past anymore, so Jane dropped it.

Lunch ended with Jane in tears of laughter as Kim recounted a time when a date had dared her to run naked around the corridors of a 5-star hotel they had been staying at.

Apparently, everything had gone fine until she had gotten back to the room and found the room door shut fast. She had hammered on the door for minutes before it was finally opened, only to find out she had gotten the wrong room. She hadn't been sure who had been more surprised, her or the 90 year old man who had answered the door and found himself confronted by an excited naked woman. Still, it had been worth it she had claimed, she won the bet and for her reward she had made her date go down on her for the next two hours.

It was a sometime later when Jane realized that she couldn't remember the last time she had laughed out loud.

******

On the way home from work, Jane had called into a store to pick up a bottle of wine. She had never been much of a drinker and never on a work night, but she was determined to go through with what Kim had suggested.

By mid-evening Jane had already finished one large glass of wine and had just started on her second by the time she realized that she was unconsciously putting off the next stage.

Eventually, fortified by another large sip of wine, she moved to the bedroom.

A massage Kim had called it. That sounded a bit more acceptable. It was just an exercise aimed at bringing awareness to her body. Oh, that didn't sound so good. Probably best not to think about the "body" part of the exercise.

She slowly began to undress and immediately began to feel very self-conscious. Thank goodness there wasn't a mirror in the bedroom or she might not have been able to go through with it at all.

Eventually she got down to just her underwear.

Surprisingly, taking off her bra wasn't too bad, as long as she didn't look down, although she suddenly found it difficult to take off her panties.

Why was she finding this so difficult? It wasn't anything different than stripping for a shower... except when she stripped for a shower she wasn't about to go touching her body all over... except that was exactly what she did when she showered. But it wasn't the same... or was it?

Jane realized that she was massively over-thinking the situation, which in turn was making her even more nervous than she had been before.

A deep breath, and the panties were finally off.

She took another large gulp of wine and got on the bed.

She closed her eyes.

She took a couple deep breaths to calm herself, then raised her right hand to her right ear. Slowly, with the lightest of touches she ran her hand down over her jaw, down her neck, across her clavicle and then back over her shoulder.

She was surprised. She must have touched herself in those places before, definitely she would have done it whilst showering or washing. But this time, somehow it felt different. Washing was so second nature to her, she didn't really think when she did it, and if she did think, she would have been thinking about the act of washing, not about how her body felt.

She traced the bony ridge of her jaw below her ear and then felt the soft hollowness on the underside of her jaw, she felt the firm but sensitive skin of her neck and then her fingers traced the bony contours of her clavicles before sweeping over her shoulder. Even her shoulders weren't a single sensation. Some of her fingers travelled over bone, some over tissue.

She used her other hand to trace a similar path over the opposite side of her neck and shoulders, marveling how complex her body was.

Together her hands slowly travelled down her sides. She felt a slight tickle as her fingers passed slowly over each individual rib until they reached her outer hips. Lying down with her eyes closed, she tried to imagine the shape of her hips just using the touch of her fingers as a guide. She must have seen her naked hips hundreds, if not thousands of times, but by touch alone her fingers were describing a much different and much more complex shapes than she had noticed before. She could feel the way the bone arched over to allow room for other bones or muscles. She noticed where her skin was firm and where it was soft and noticed which areas were more sensitive than others.

Her hands rose up the front of her body, never losing contact. She must have felt it before, but she was surprised at how high her ribs were above her stomach. But for now she kept her hands moving, up over the cliffs of her ribcage and then skirting around the sides of her breasts. Her hands met above her breasts at her sternum, resting for a second on the bony plate of her chest before they jointly swept down between her breasts to her stomach once more.

She took a deep breath in and felt her hands on her stomach raise and lower in time with her breathing. Fascinated with the movement of her body, she held her breath for a couple of beats before breathing out again. Not only was she now aware of the movement of her ribs, but with her hands she could feel her muscles move in time with her diaphragm. She had never been so aware of the simple act of breathing before.

She took a couple more breaths in and out, just to feel the movement of bone and muscles within her body, before her hands moved back up her chest again.

She guided her hands up the sides of her body, mainly because of how good it had felt the first time, but once she reached her upper chest, and before she could overthink it, she let her hands drift back down her body, except this time they went directly over her breasts and nipples. Considering how much she had been building up the moment in her mind, she was surprised at how little her touch felt erotic, instead it felt pleasant with just a little tingle as her palms brushed over her nipples. If anything, she enjoyed feeling the shape and texture of her breasts more than any erotic feelings she might have been expecting.

But keeping Kim's directions in mind, she didn't dwell too long on her breasts, just in case it did start feeling a bit erotic. Instead, she let her hands drift down the outside of her thighs.

She was surprised at how firm her thighs felt. She had always leaned towards thinness, and John was always quick to point out if he thought she had put on a couple pounds. But even so, she was surprised at how lean her thighs actually were. They weren't overly thin, but she could definitely feel muscle beneath the surface of her skin. She tensed her legs and immediately her thighs became surprisingly hard.

She brought her hands up the front of her tense thighs and after letting them roam briefly around her abdomen, she let them sink down between her inner thighs.

It was a good job that she had skirted around the outside of her vulva, as her inner thighs turned out to be particularly soft and sensitive. This was the first time in this exercise that her touch felt even slightly sexual, so without hurrying too much, she moved her hands back up her body again.

She wanted to explore more of her legs, so she turned on her side and brought her knees to her chest. From here she could explore her lower leg and especially her bum. She had always thought her bum as a uniformed curved shape, but in this position her fingers told her that it was made up of both curves and flats as her bent legs caused her glutes to come under tension. Wow, it felt so lean and hard in this position.

After letting her hand explore for a while, she turned onto her other side so that her other hand could explore her other leg and bum cheek.

Finally finished with her leg, Jane turned onto her back once more.

She decided to stop there for tonight, worried that the temptation to explore her body more might lead to other things, although before she finally stopped, she flowed her hands back up her body, and then with a smile on her face, she gave her breasts a quick playful squeeze.

Finished, she lay where she was for another minute, just feeling her body breath, fascinated that now she was paying attention to it.

When she finally got up, she didn't fully dress. Instead, she wrapped a blanket from the cupboard around her naked body and picking up the half-finished glass of wine she wandered out into the main room. She put on some music and sat slowly sipping the last of her wine whilst she thought over what she had experienced over the last half an hour.

Kim's description of getting her mind in tune with her body was accurate, but it didn't really cover how it had felt. She realized now that for her entire life she had taken her body for granted, so it had been a revelation to discover how complex it was and how nice it was to touch. This thought brought a brief moment of sadness - if John had been a better lover, would she have experienced this much sooner in her life? But the moment was only brief, she no longer wanted to think of John and the past, she didn't want to look back, she wanted to look forward.

She still didn't know exactly what she wanted, but she knew that it was definitely going to be better than she had before.

******

Two days later and Jane rushed into the office where Kim worked and excitedly dragged her new friend into a nearby staff toilet, after first checking that it was empty.

"I had an orgasm!" proclaimed Jane excitedly.

Kim laughed heartedly, "Congratulations. But maybe you don't want to shout it too loud unless you want the rest of the office to know."

Jane lowered her voice a fraction, although nothing was going to dampen her current excitement. "I did what you said and tried giving myself a massage without it becoming too... you know... intimate. I managed it for the first couple of nights and it felt really good." Jane actually blushed a little at what she was admitting to. "But last night, my hands sort of, um, went where they wanted to... and they started touching places... and... I HAD AN ORGASM!" She was no longer able to contain her excitement. "When do you think would be a good time for me to start dating?"

Kim had a moment of realization. She had thought that Jane just needed somebody to talk to, maybe somebody to give her advice, but now she realized that what Jane really wanted was somebody to tell her what to do, to be a sort of mentor as she navigated the minefield of personal relationships. And apparently Jane had picked Kim to be that person.

But did Kim want that level of responsibility? She looked at Jane's excited face and immediately knew that she couldn't turn her down. The poor woman was completely out of her depth when it came to sex.

"Ok, steady on. We are probably still a little ways off you being ready for dating. So, getting back to last night, how many times did you get yourself off?"

Jane looked confused, "What do you mean? I had an orgasm." She felt the need to clarify that she had had an orgasm, just in case Kim had missed the importance of what she had told her.

"Yes" replied Kim patently, "But how many orgasms did you have?"

Now Jane's face was a mixture of surprise and shock, "You mean I can have more than one orgasm... in a single night?"

"Yes" replied Kim, this was going to be more work than she anticipated.

"Do you have multiple orgasms?" asked Jane fascinated. She was still coming to terms with the fact that she had recently experienced her first orgasm, so the thought of multiple orgasm seemed beyond comprehension.

"Depends on my mood" replied Kim in an off-hand tone, "If I've had a stressful day I tend to give myself a minimum of a couple, one to relieve the tension and another for pleasure."

Jane was amazed at the casual way in which Kim was discussing something she had previously thought of as verging on the mythical. "So what do I do next?" she asked.

"For now, you just keep doing what you are doing but try varying it up a bit. Just have fun and experiment, you'll soon find what you like most. Who knows, you might even find something else that gets you off faster"

Jane thought this through. It seemed to be a lot to take in, but her musing was interrupted when Kim next asked her a question.

"It's Saturday tomorrow, do you have anything planned?"

"No" replied Jane, these days she never had anything planned, life was just one long trudging procession to the next day.

"Fancy coming shopping with me tomorrow? I thought I might help you pick out a new toy."

Jane was excited to be unexpectedly invited to go shopping with Kim, not so much to go shopping, but just because somebody was inviting her to do something.

Although why did Kim seem to think she might be interested in toys? Surely Kim didn't think she still played with toys... then the realization came to her... "Oh."

******

Chapter 3 - The First Date

It was now three weeks since Jane's first orgasm and she now considered herself an old hand at the ancient art of self-pleasuring, especially when she used her new toy.

The toy she had chosen, with a lot of encouragement from Kim, turned out to be six inches of purple vibrating happiness... with knobbly bits.

Since then she had practiced with it every night. And what an experience it had been. She now knew there were actually different types of orgasms, from the slow-burn relaxing orgasms to the intense whole body trembling orgasms, from orgasms that involved her rubbing her clitoris furiously (thank goodness Kim had insisted that she buy some lubricant when she purchased her toy), to the deep mellow vibrating orgasm she experienced when slowly moving her vibrator in and out of herself.

This was a completely new world of experiences that she had never suspected had existed.

But with these new experiences came a number of bitter sweet emotions.

Her joy at discovering a whole new world of pleasure was tempered by the fact that it had been denied to her for most of her life... well, maybe "denied" was the wrong word, She hadn't "known" that such pleasure was available to her. But now she knew, and best of all she now knew that in a very literal way, her pleasure was very much in her own hands.

However, today wasn't a day to be looking back and wondering "what if?", today was a day for looking forward and taking her next step to becoming...

... actually, Jane didn't know what she wanted to become, she just knew that anything would be better than what she had been. And today was the next big step.

Today she was going to ask Kim about dating.

The thought of dating filled Jane with a sense of dread and excitement. She really did want to meet new people, but the thought of going on a date and perhaps even... sleeping with someone new, made her feel queasy with nerves. But it was also something she desperately wanted to do.

She was meeting Kim for lunch, to better give themselves time and privacy to discuss the matter.

"So, how do I go about meeting new men?" asked Jane nervously.

"Easy" replied Kim brightly, "Dating apps."

Jane was a little puzzled, "But I thought you wanted me to avoid long term relationships? Isn't that what dating apps are meant to be for? To find your ideal partner."

Kim burst out laughing, "You really don't want to go believing all those shmaltzy adverts. Most dating apps are all about hooking people up for gloriously meaningless one-off sex."

"Here, give me your phone" Kim said, holding out her hand.

As Jane watched Kim type furiously on her phone for the next twenty minutes, she couldn't help but reflect on how differently the two of them viewed dating. Kim viewed dating as just a way of meeting and fucking new and exciting people without the need for messy entanglements, whereas deep down, Jane just wanted to find a man that would accept her, look after her, and if she was lucky, to make her feel good.

Kim had tried to explained to her that she needed to experience a certain level of "meaningless" sex in order to really know what she wanted, in order to avoid what Kim described as "falling madly in love with the first jerk that makes you cum."

Jane thought that Kim was being a bit too cynical about it, but on an intellectual level she could see some sense in what Kim was saying. Even if it did conflict with how she felt emotionally.

"There," exclaimed Kim at last, "all set up." She handed Jane back her phone.

For the rest of their lunch break, Kim showed Jane how to use the dating app and they even had a bit of a giggle looking at some of the profiles people had uploaded to it.

That night, before her pre-sleep orgasm, Jane scrolled through the many profiles of all the men prepared to "date" her. There were so many potential dates that it was hard to know where to start. However, knowing that there were so many options gave Jane a little buzz of excitement.

Over the next few days, Jane and Kim worked through some potential dates on the app. Some of the ones Jane picked out, Kim ended up dismissing out of hand. There were a few that looked hopeful, and at Kim's suggestion, Jane messaged a few with some questions and asked them to tell her more about themselves. Based on the responses, Kim dismissed even more of the potential dates. However, eventually they had their first candidate - Justin.

One of the ways that Justin stood out from the crowd was his profile picture. Whilst most of the men tried to look mysterious and brooding, with varying degrees of success, Justin's picture portrayed him with a simple friendly smile.

Jane messaged Justin a few times and his responses seemed to meet with Kim's approval. At least on the surface he appeared to be a nice guy. Which is why Jane finally agreed to go on a date with him this coming Friday evening.

Jane couldn't decide if she was more excited or nervous. The two competing emotions were fighting for dominance within her. She couldn't believe she was actually going to do this.

However, it appeared that Kim wasn't finished playing mother-hen just yet.

As Jane wasn't used to dating, Kim insisted that they set up some safeguards. For a start, Kim would phone Jane an hour after the date was due to start. If the date was still going well at that point, Jane could cryptically let Kim know everything was alright. Alternatively, if Justin turned out to be a creep, then Jane could pretend the call was notifying her of a family emergency, and that she needed to leave right away.

Also, Kim wanted Jane to call her no later than an hour after they got back to Justin's place, assuming the date got that far. Kim wouldn't know when that would be, so Jane had to call her, no later than 11:00pm mind, just to let her know everything was OK.

Jane was a little surprised that Kim was being so cautious, and it made her a little nervous that Kim thought such precautions were necessary, but she was also very grateful that somebody was looking out for her.

******

Friday evening and Jane was practically shivering with nervous excitement as she entered the restaurant.

She had agreed to meet Justin here at 7:00pm but had purposefully turned up ten minutes late. Normally Jane hated not being punctual, but she hated the thought of sitting alone in a restaurant even more.

Luckily the maître d' informed her that the other dinner guest had already arrived and led her to her table.

Jane was relieved to see that Justin actually looked like his profile picture on the dating app, something that Kim explained wasn't always the case.

Jane was also pleased to see him stand to greet her. He didn't try to be overfamiliar, he just greeted her in an open and friendly way, then remained standing until she was seated.

She couldn't help but admit to him that she was a little nervous about the date, although Justin assured her that it was normal and they could just take things as they happened.

Between courses, the two of them chatted, Jane finding it surprisingly easy to talk to Justin. They didn't talk about anything impactful, just filling in a few more details about themselves, their likes and interests and what they did for a living. It was just a pleasant conversation that did a lot to help her relax.

When her phone rang a little later, Jane had almost forgotten that Kim had arranged to call her. She made apologies to Justin and then answered.

"Oh, hi Kim. Look, I'm sorry, I'm with a friend" she smiled shyly at Justin. "Can I call you later... Great. Speak to you soon."

Turning to Justin, "Sorry about that. Just someone I know who just wanted to chat."

In fact, the use of the word "friend" was the codeword she and Kim had agreed on to let Kim know the date was going OK.

The rest of the meal went fantastically. Jane barely noticed her food as she was becoming more and more enamored with Justin. But the meal was drawing to a finish and soon she would have to decide on the next step.

In the end, things did get a little awkward. Jane realized that she wasn't keeping up her end of the conversation as much as she had been, as she nervously contemplated her next big decision. For his part, Justin seemed keen to take things further but also seemed reluctant to pressure Jane into anything. So, the conversation lulled even more.

Finally, Justin spoke up.

"So, I've had a great time, and I was wondering, did you fancy coming back to my place, for a coffee or anything else?"

There was a definite implication of what "anything else" was, although, despite Justin's easy confidence, there was no sense that he automatically assumed she would take him up on his offer. In the end it was Justin's easy confidence that encouraged Jane to accept.

"I'd like that. Thank you."

After he had paid for the meal, where Justin had insisted on paying for both of them, he led them back to his apartment.

Luckily it wasn't far, and the weather was still warm enough to be pleasant even at this time of night.

Jane's mind was swirling with possibilities. She still couldn't believe that she was doing this and had absolutely no idea as to what was going to happen next. But whatever was going to happen was only occurring because she, with a little prompting from Kim, had chosen to take a chance. The thought was surprisingly comforting.

When they got back to Justin's apartment, Jane was a little surprised.

At first glance the apartment appeared to be a haphazard assortment of furniture and decorations, but the more she looked, the more she realized it actually had a theme to it. She wasn't exactly sure what the theme was, but it all seemed to harmonize together. Somebody (Justin) had gone to a lot of trouble to make sure the room had a distinct tone, which appeared to convey a relaxed comfortable feeling. Neat enough to be pleasant, but not so neat that you would be afraid to move anything from its allotted place.

"Can I get you anything to drink?" asked Justin as he offered her a seat on the couch.

"A wine if you have it." She responded guardedly.

"Anything in particular?"

"White please."

"Sure, but I meant any particular variety or year?"

That caught Jane off guard. "Um, do you have any Moscato?"

Justin seemed to contemplate for a moment, "Embarrassingly I don't, but I do have a quite good Riesling 2015 I think you will like."

"Ok, that will be fine." Jane had never had Riesling before, but she would try it, just to be polite.

When Justin got back and handed her wine, he took a seat in an armchair opposite her, as if giving her space to decide what she wanted to do next.

She took a sip of her wine, it was rather good, and glanced around the room again. The more she looked at it, the more she thought it reflected Justin. The decor was a little unconventional, but relaxed and comfortable, just like him.

"So, you use X-Dating app?" asked Justin.

It was a completely redundant question because of course that was how they met. Instead, Jane thought that Justin was purposely giving her an opening to talk about herself and let her maybe give some hints about what she hoped for or wanted from tonight.

"Well, I've not really had much experience dating. I was married for so long and...." she started hesitantly.

But before she could help herself, Jane was completely unburdening herself to him. She knew that she shouldn't, but didn't seem to be able to stop herself, he looked so kind, and he was such a good listener.

In the end she had told him everything, about the fact that her ex-husband John was the only person she had ever slept with, how that she suspected that he hadn't really loved her, but she couldn't find the courage to do anything about it and how in the end it was him that had left her and how broken and miserable it had made her feel.

She told him everything. And in the end, she even shed some tears over how depressing her story was.

Justin moved over to sit beside her. He put an arm around her - she flinched slightly, then lent into him.

"I'm sorry" she said, "I didn't mean to ruin your evening."

"It's all right" he assured her. "If you're not ready for anything else to happen tonight, we can just sit and chat. It's your choice."

Jane looked at him quickly, "No, I want... it to happen. I do. If you still want too of course." She was fully aware of how much of a mess she was making of her first date and couldn't blame Justin if he wanted to back out.

There was the briefest of hesitations from Justin, "Look, you're a beautiful woman, and yes, I'd like to take you to bed, tears and all," he gently brushed a lone tear off of her cheek, "But I won't unless I'm sure it's what you really want." He looked at her, a note of seriousness mixed with concern in his expression, "Is it what you want?"

For the first time since the thought of dating entered her mind, Jane knew what she really wanted, "Yes" she replied breathlessly.

******

Justin's bedroom was in a similar theme to the main room, chaotic, but coordinated calmness, although whereas the main room was in shades of rich browns, the bedroom was decorated in shades of pale blue.

The bed was of course the focal point of the room. Both the headboard and the footboard were formed with intricate brass swirls. Anywhere else the bed would look eccentric and out of place, but here, it perfectly matched the style of the rest of the apartment as well as Justin himself.

Justin led Jane into the bedroom and just before reaching the bed he turned to face her. There was a brief pause before he moved closer and gently held her waist as he leant in to kiss her.

The kiss was soft and gentle, but the tenderness behind it completely made Jane melt, especially so soon after he emotional unburdening. She found herself savoring the feel of his kiss before not being able to hold herself back from kissing him in return.

Jane's kisses became more passionate as she felt his hands slide up from her waist until they encircled her back, pulling her closer to him.

As his soft kisses continued to excite her, Jane's inhibitions were quickly falling away. She had been so long without any real affection that his kisses were like the first water after a lifetime of drought. Almost by themselves, her hands were working on the buttons of his shirt, eager to access his chest.

She groaned deeply as he lowered his head and began painting soft kisses down her neck. Her hands were now beneath his shirt, feeling and exploring his hot hard chest.

She gave a small moan of disappointment as he slightly moved away, but it was only so that he could step behind her. She gave a contented sigh as he first moved the hair aside on the back of her neck and then felt his hot breath on her sensitive skin a fraction before his lips found her neck once more.

There were several more wonderful kisses before Jane felt a slight tugging at her back. There was the unmistakable sound of a zipper, just before her dress went loose. Justin lowered her dress and she quickly stepped out of it.

Justin was now back to kissing her now bare shoulders as his hands caressed her upper arms. She leant her head back and let out a long contented sigh, his touch felt so good.

Another movement, another slight tug at her back and her brassiere suddenly loosened. She lowered her arms and let her bra slide free, joining her dress on the floor.

With her brassier discarded, the realization of her situation came home to her. Here she was, largely naked in a strange man's bedroom. She was still very nervous, but now her excitement warmed her, and let her know that she wanted more, a lot more.

There was another sound of cloth moving against skin behind Jane and then Justin stepped in front of her, just wearing his boxers, before leading her up and onto the bed.

Jane went willing, still in a partial daze, but now her daze was caused as much through arousal as it was nervousness.

Justin lay her on her back and then positioned himself beside her. Leaning slightly over her so that he could look her directly in her eyes, "Do you still want this?" he asked in a quiet voice, letting her know the choice was entirely hers.

Jane simply nodded, she didn't think she had wanted anything more in her life.

Justin kissed her fully and softly, whilst his hand gently cupped her breast.

Jane felt herself melt even more. Her arms wrapped around his neck as his hand began to explore the soft slopes of her breast.

Jane completely lost any concept of time as Justin slowly went about exploring every inch of her body with his hands and mouth.

By the time Justin was back kissing her face and lips, Jane's had lost her panties and her entire body was burning with desire. After fiercely kissing him, she broke the kiss long enough to speak a single word, "Please."

Instantly Justin knew what she wanted, moving gently atop her, his legs between hers, he kissed her gently as he moved one hand down between their bodies.

The next thing she felt was the head of his cock pressing against her labia, he moved a little more, now he was pressed against her hot entrance.

Justin paused long enough to raise his head so he was looking directly into Jane's eyes. She saw the lust in his expression that matched the way she felt herself. She reached up and pulled his head to her in order to feel his lips once more against hers, but her kiss turned into a long drawn out moan as he slowly pushed into her.

Her head arched back, her hips raising slightly to meet his. His movements so slow that she could feel the fullness of him moving up inside of her.

She let out another sigh as he began to just as slowly withdraw from her.

Jane was certainly not a virgin, but she felt like one in this moment. This was like nothing she had experienced before. The tenderness and emotion she was feeling from Justin, the softness of his touch, the hardness of his body, the way her body was reacting to his, she could barely contain the emotions welling up inside of her.

As Justin began to stroke inside of her, Jane completely lost herself to the sensations flooding through her. She clung to him as she felt his cock filling her up, the way his pelvis pressed into her clitoris on every thrust, the way her pussy felt stretched, but not painfully so.

Jane's arousal increased with every thrust of Justin's cock. Every stoke into her took her higher towards her ultimate pleasure. Soon she was gasping as if the air around her was too thin, or her chest too tight. The fire from her loins had now spread throughput her whole body. She was burning with desire. Her body moving in time with Justin's. Her ecstasy reaching heights that she hadn't previously imagined possible.

And then her mind went soaring.

She cried out as her whole body shook uncontrollably at the force of her orgasm.

She clung desperately to Justin, afraid to let go.

Even the orgasms that she had given herself, either through fingers or vibrator, were only a pale imitation of what she was feeling now.

Whilst her body convulsed with pleasure, she was only dimly aware that Justin was cumming as well. She heard him cry out, she felt a new sensation inside of her, but she was too deep into her own ecstasy to fully realize what was happening.

Justin's own orgasm had been pretty impressive, even by his own experiences. But there had been something within Jane that had stirred him.

He had been a little hesitant at first, not wanting to take advantage of a vulnerable woman, but seeing her hopeful willingness, and noting the obvious need inside of her, he hadn't been able to resist.

As he tried to catch his breath, he tried not to put too much weight on Jane, but it was a little tricky as she was still holding onto him tightly, his head resting in the crook between her shoulder and neck.

It was whilst he was resting there that he heard the faint sounds of crying, but so quiet it was hardly louder than Jane's breathing.

Immediately he levered himself up so he could see Jane clearly.

"Are you alright?" he asked concerned and afraid that he might have pushed her into something she wasn't ready for.

She beamed up at him, her radiant smile in contrast to her teary eyes, "More than alright, that was beautiful. I've never felt anything like it"

He leaned down and kissed her lips softly before then kissing the tears from her cheeks.

"You had me worried there for a moment," he confessed.

She smiled wanly up at them, then they both laughed as the tension between them broke.

For the longest time afterwards, Jane just cuddled into Justin. It just felt so good to be with somebody who treated her with love and respect. She had completely forgotten what it felt like.

Finally, "You don't regret sleeping with me, do you?" she asked in a quiet voice.

"Of course not" he responded a little perplexed.

"It's just that I thought I might have frightened you off, what with me getting a bit emotional when we first got here."

Justin turned his head and lightly kissed her on the forehead.

"Well... it was a little unexpected. But we all have our own hangups. I just hope I was able to help a little with how you were feeling."

Jane leaned up briefly to give him a quick kiss before snuggling back into his chest, "Oh, you certainly helped with the way I was feeling. I've never felt so good."

There was a pause.

"Justin...?"

"Yes?"

"Can we do that again?" She looked up at him hopefully. She might be a forty four year old woman, but at the moment she felt as excited as a teenager.

Justin laughed, "Only if you promise not to cry afterwards. You gave me a fright last time."

This time they both laughed.

"I'll try, but no promises" Jane replied with mock seriousness.

This time the passion came easier and faster for both of them. This time Jane found herself taking a much more active part in their mutual pleasure.

As they began to kiss, Jane's hand slid down between their bodies until she could grasp Justin's cock. He grunted his appreciation as she first squeezed him before leisurely beginning to stroke him.

In response, Justin's kisses became more passionate and his hands began to massage her breasts with increasing firmness.

Their movements were much more urgent than last time, but neither of them were currently able to slow the pace of their passion.

Jane gasped as she next felt Justin's hand on her pussy. She gasped again as his hand briefly passed over her clit, then groaned deeply as she felt one of his fingers enter her. There was practically no resistance at all to his digit as she was already soaking wet and ready.

"Christ you're hot!" he exclaimed.

Aroused as she was, Jane wasn't sure if he meant her in general, or whether he was referring to the state of her soaking pussy.

"Fuck me Justin" was all that she could manage in response.

Not the most eloquent thing she had ever uttered, but luckily he got the message.

They both groaned deeply as he entered her.

Justin was content to stroke into her slowly, giving them both time to enjoy the sensation. However, Jane found herself to be extremely horny, even as she was trying to let Justin set his own pace. But the effort needed to restrain herself was having the opposite effect as she found her arousal levels climbing fast.

Jane was just about to lose her battle with her self-restraint when on his next stroke Justin completely lowered himself so that he was lying fully on top of her, pushing himself further into her than he had before. Jane hummed her appreciation, then sighed as she felt Justin briefly nibble her earlobe.

"Wrap your legs and arms around me" he whispered into her ear.

Jane wasn't sure what he had in mind, but did what she was told.

After a quick kiss, she felt Justin shuffle up so that his knees were now next to her backside and he had lifted her hips off of the bed.

She felt his arms slide under her back. What was he doing?

"Hold on tight" he told her with a big grin on his face.

Jane tightened her grip with her arms and legs as she suddenly felt herself lifted into the air.

She came to a brief stop, still clinging to Justin as she saw he was now kneeling on the bed.

Suddenly Jane began to laugh out aloud as she realized that all through Justin's unexpected bedroom gymnastics, his cock had been inside of her the whole time. For some reason she found this hilariously funny.

She had hoped that this date would have introduced her to the pleasurable side of sex, although it had never occurred to her that sex could also be fun. It really was a revelation.

Justin shuffled around a bit more until he could stretch his legs out in front of him.

Jane now found herself sat in Justin's lap, his cock still firmly planted inside of her.

Still smiling to herself at the erotically humorous turn of events, she eased her grip on him slightly, but she didn't let him go as it just felt so good to hug him close in this position.

She kissed him again, laughter still in her eyes, "What was all that about?" She enquired with a smile.

"Well, I was hoping we could take things a bit slower this time, but I could see you were getting a bit excited..."

He wasn't wrong she admitted to herself.

"... so I thought this position might help us take things a little slower."

Now she was sat in his lap, Jane could see why Justin had moved them to this position. He could hardly move and if he held her hips, she wouldn't be able to move much either. So, he wanted it slow did he? OK, she could manage that.

She began to slowly walk soft kisses up the side of his exposed neck, whilst at the same to she began flexing her inner muscles around his cock, which was something she had only previously done with her vibrator.

She ran her tongue around the inside of his ear before asking in a whisper, "Slow enough for you?"

The reply was a breathless "Yes" as she squeezed his cock as hard as she could.

For the next forty-five minutes Jane and Justin concentrated on keeping their joint arousal level high, but never high enough to approach orgasm.

Sometimes she just squeezed him, sometimes she ever so slowly rode up and down on his cock whilst she let him kiss and lick her nipples. But the thing she found that she liked to do the most was to just slowly move her hips in slow circles around his lap, just feeling the different places he was touching her inside. Sometimes they kissed, sometimes they just looked into each other's eyes as they both enjoyed the physical connection they shared.

However, after nearly three quarters of an hour of being slow fucked, Justin couldn't take it any more.

He began to encourage Jane to move faster on him, which she was more than willing to do, as she was getting more than a little desperate herself.

Jane was just about at the stage of completely losing herself to her passion when she felt herself being forced backwards onto the bed again.

Through some magic Justin was back on top of her and thrusting hard into her.

She looked up and saw that his normally calm and happy-go-lucky expression was gone, replaced with an animalistic desperation to cum. His teeth were clenched and she could even see the veins on the side of his neck due to the pressure building inside of him.

It was the most erotic thing Jane had ever seen.

She began thrusting up against each of his stokes, now desperate to cum as much as he was.

She clung to his neck, her mouth close to his ear, "Cum for me Justin" she urged.

Whether he heard her or not, she wasn't sure because just at that second Justin cried out and thrust even harder into her, his semen coating her insides.

The expression of ecstasy approaching pain on Justin's face as he came was enough to tip Jane's pleasure infused body over the edge of her own orgasm.

She clung to him with arms and legs until the last tremors of both their orgasms had receded, then she found herself still reluctant to release him until they had both got their breathing under control.

Finally, Justin leant down and kissed her softly, "So, are you going to let me go, or are we going to have to stay like this all night?"

She laughed and finally let him go so that he could roll over and lay beside her.

There then followed another long bout of the pair of them silently basking in the warmth of each other's company.

Jane was just beginning to get restless again when a thought struck her. Damn, she was meant to give Kim a call to let her know everything was OK, but in the passion of their encounter she had completely forgotten.

She quickly turned to Justin "Um, sorry, be right back. Just need to make a call."

Justin looked perplexed, but before he could say anything, Jane was out of bed and running naked across the bedroom as she had left her clutch and phone in the main room.

She didn't want to get into a conversation with Kim, as she was already keen to get back to Justin, so she messaged Kim instead, "Great time. Spk Mday."

Almost instantly a message came back from Kim, it was just three emoji's, a thumbs-up, what looked to be an auberge, and a winking face.

Jane wasn't sure what the auberge was meant to signify, but she assumed Kim was just wishing her well.

As Jane walked back into the bedroom she could see that Justin was waiting for her. He looked fantastic lying naked on the bed.

"So," Jane began coyly, "Ready for more?"

She could see by Justin's smile and his stiffening cock that he certainly was ready.

********

It was a long wait until Monday lunchtime, but Jane reasoned that something this momentous couldn't be handled over the phone, despite how desperate she was to talk to Kim about it.

So, it was just after twelve o'clock Monday lunchtime, the two of them sat in a quiet diner, before Jane was at last able to confide in Kim about her date with Justin.

"He was fantastic!" gushed Jane before Kim even had a chance to ask. "He was even really sympathetic when I told him about John and how bad things had been for me. He didn't even mind when I cried."

Kim was shocked, "Oh god no! Please tell me you didn't go on about your ex, and please don't tell me you cried. You didn't, did you?"

Jane was a bit bashful when she admitted that she had in fact done those thing, although judging by the way Kim was reacting, she certainly wasn't about to admit that she had also cried after her first orgasm with Justin.

"And he still fucked you after that?" asked Kim incredulously.

"Yes, a few times" Jane responded a little defensively.

Kim eyed her seriously, "He wasn't some sort of pervert who got off on vulnerable crying women was he?"

"No!" replied Jane immediately coming to Justin's defense, "He was really nice about it. In fact, he said we didn't have to do anything at all, we could just sit and chat if I wanted."

Kim groaned, "Oh god, you got a romantic one, didn't you?"

"Maybe, he was very sweet. I'm not sure why that's a problem?" replied Jane.

Kim sighed, "Remember I said it wouldn't be good for you if you fell head over heels for the first guy that gave you an orgasm?"

"Well yes... but maybe he's the one."

"Maybe, but you don't know for sure do you? After all he's only the second guy you've ever slept with, isn't he?"

"Yes, but..." Jane could see the sense in what Kim was saying, but Justin had been so tender and special. She was sure that he would be the right one for her.

"So" continued Kim, "Tell me everything, especially all the gooey details."

So excitedly Jane told Kim everything that had happened that night, even the gooey details.

Kim seemed impressed. "So, did you stay the night?"

Blushing, Jane admitted that she had.

"And the next morning?" Kim enquired, a slight grin on her face.

"Justin was a real gentleman" Jane confirmed.

"Not too much of a gentleman I hope?"

"Well, it might have been getting close to near mid-day before I left." Jane grinned in return. The morning had turned into a session every bit as good as the night before, maybe even better.

"Good girl." Kim gave an approving nod, "So now we can start looking for your next date."

Jane wasn't sure that she wanted to date anyone else, even if she actually could see the sense behind it.

Although, she did now have Justin's number, so she might just drop him a message... just to say thank you... and maybe just keep in touch? She would like that. And if things developed further....

********

Chapter 4 - Obeying Can Be fun

It was a few months since her first date with Justin and life was quite a bit different for Jane.

At work the differences were subtle, like the fact that people actually seem to notice her more and often took the time to chat with her. Also, she tended to get invited to more planning meetings, something she still felt a little uncomfortable about.

But the big change was that with Kim's help, she was more actively dating, although it hadn't all been plain sailing.

The first date after Justin hadn't gone well. She couldn't put her finger on it, but she just didn't gel with the guy. At the end of the meal she had paid her share, just to show there were no hard feelings and then left.

Initially she had viewed it as a setback and had worried she wasn't really cut out for dating. However, Kim had reassured her that she was just suffering from second stage rebound syndrome. In Kim's words, it was just Jane's bad luck that she had dated somebody like Justin so soon after becoming single.

Jane didn't really see it as being bad luck but decided not to argue the point.

Luckily the next couple dates had been a lot better and she had ended up going back to the guy's apartment both times.

Each of those dates had been real eye openers for Jane. Whilst they didn't have the specialness she had experienced with Justin, they had both been really good in different ways, especially when it came to the sex. Jane was beginning to realize that sex with a new partner was like a mystery gift, you never what you were going to get until you experienced it.

Even more surprising was the realization that not only were her partners different, but that Jane's attitude to sex changed depending on who she was with, sometimes she wanted it romantic, sometimes she wanted it energetically passionate.

Unfortunately, her most recent date had also been a washout.

On the surface the date appeared just her sort, pleasant, funny, attentive, good looking... but again, something just didn't gel with her, so she again ended up going home alone after the meal.

She had thought that Kim might have disapproved of her not following through with the date, after all, each new date was a new experience, but it turned out that Kim saw it as a good sign.

"Don't sweat it. You're just beginning to figure out what you want" explained Kim, "You're making your own decisions. And that's good."

It might have been a sign of emotional growth, but after building herself up for the date, she was now feeling a little sexually frustrated.

Time to find the next date.

********

It took another two weeks and a couple more abortive attempts before they found the next candidate for Jane to date - Tom

It was Kim who first found Tom's profile on the dating app, and it had caught her eye because it looked "interesting".

Looking at Tom's profile, Jane could see why.

Tom's profile listed his occupation as simply "Businessman", and whilst he was a few years older than her, he wasn't that much older. But what caught her attention most was his direct method of writing when she read the rest of his profile. In his profile Tom made it very clear that he wasn't looking for a relationship or even friendship, he was only interested in sex. Whilst this direct approach might have put off a lot of women, it was currently just what Jane was looking for. So she dropped Tom a PM to enquire more about him.

As it turned out, Tom had his own requirements, the chief of which was that the potential "date" should not wear casual clothes but instead present themselves in a dress, preferably formal, preferably of a plain dark color. A degree of elegance would also be appreciated. Tom also made it clear that if they met, Jane should not ask any personal questions of him as he would not answer them, which also suited her just fine.

Instead of being put off, and despite her normal preference for a more romantic date, Jane was actually a little intrigued with Tom. He appeared to be very clear in what he wanted, he was confident enough to ask for it directly and seemed unconcerned if she accepted his terms or not.

The confidence this implied was actually a bit of a turn-on, and after recent events, Jane surprisingly found Tom's strength of character extremely appealing.

After a few more back and forth messages, the date was agreed and Tom provided Jane with the address of his home. Apparently pre-sex meals were also something Tom didn't care for.

Two nights later and Jane was stood at Tom's front door. She was surprised to find that she was actually more excited than nervous, but tried not to show it as she knocked on the front door of the large house.

After a brief pause the door was opened by a tall powerful looking man who was dressed in suit pants, a shirt and a tie, as if he had just stepped out of a boardroom.

"Hi, you must be Tom, I'm Jane."

Tom's slightly stern expression didn't change, instead he took a few seconds to very obviously look her up and down before giving her the briefest of nods of approval.

"Pleased to meet you, do come in."

He stood aside to let her in and then led her into a large main living space. To call it a room would have been a disservice to how large it was, yet at the same time it felt surprisingly empty. The biggest piece of furniture in the space was a large leather couch that looked as though it could comfortably seat six people and two matching leather armchairs. On one wall hung a modest sized television, which was the only decoration on the walls. Jane guessed that Tom didn't spend much time in this space.

After offering her a seat on the couch, Tom asked if she wanted a drink.

"A white wine would be nice, thank you."

Tom nodded and left the room, because of course there wasn't anything so out of place as a drinks cabinet to spoil the emptiness of this room.

When he returned, Jane was surprised to see that he hadn't fixed a drink for himself.

Accepting the wine, she took a quick sip, more to calm herself than because she needed it.

Tom took a seat in one of the armchairs opposite her and just regarded her in silence for a couple minutes before speaking.

"I hope I made myself clear in my correspondence with you. I am not looking for a relationship nor a friend, I am simply interested in sex with you. I will do my best to make the experience pleasurable for you and in return I expect you to do the same for me. Is this acceptable to you?"

For a second Jane was caught off guard by the blunt directness of what he had said. It was one thing to read it in a post, it was quite another to have it said to her in such a straight manner.

She drew in a deep breath, "Yes, that is perfectly acceptable to me." Then, before she could change her mind, "Shall we proceed to the bedroom? There doesn't seem to be much point in delaying if we both agree why we are here." She was surprised that her voice sounded so calm and business-like, because she certainly didn't feel it at the moment.

Tom nodded, obviously pleased at her response.

"Certainly, this way if you please."

Tom led her up the stairs and along a hallway lined with several doors to what she assumed was his bedroom. The bedroom was fairly formal, but unlike the downstairs space it at least looked like a room Tom might actually spend some time in. Again, there was the minimum of furniture present, but the enormous bed more than made up for it.

Jane was halfway across the room when Tom called her to a halt.

"Turn around" he causally instructed her.

She did as he requested and saw that he was still standing next to the door.

"Undress." It was a single word command delivered with a measure of natural authority.

Jane wasn't used to being ordered around in such a blunt manner and her first instinct was to rebel and refuse, which actually came as a surprise to her.

But then a thought occurred to her. She had come to realize that she was going on these dates to prove to herself that she could decide how she lived her life and that she could be in charge of her own pleasure, that she could be strong. Paradoxically, this also meant that if Tom was to order her around, it would only happen if she willingly allowed it to happen.

Her decision made, Jane reached behind her back and with just a little fumbling located and pulled down the dress's zipper. She eased the dress down her waist and over her hips before letting it pool on the floor. She picked up the dress and neatly folded it on one of the room's few pieces of furniture, then she bent over to undo the clasp on one of her shoes, until Tom stopped her.

"No, leave your shoes on. You can keep the jewellery on as well but lose the rest."

Jane first checked that she was OK with this new instruction, then removed her bra and panties before defiantly facing Tom. To her great surprise she actually didn't feel embarrassed standing almost completely naked in front of a man that she had first met less than an hour ago. She knew she had a good body for her age and by his appraising looks, Tom thought so as well.

"Very nice, now kneel down facing me" he instructed.

With the briefest of hesitations Jane did as she was told.

Once she was kneeling, Tom began to undress himself, his eyes never leaving hers.

As he unbuttoned his shirt, Jane could see his large frame didn't have any excess fat to it, his chest was sculpted of solid muscle. Given that Tom obviously didn't have a manual labor job, she guessed he must spend a lot of time in the gym and judging by his enormous pecks and biceps, most of that time was likely spent on weights.

Unlike her, Tom didn't bother to fold his clothes, instead he merely discarded them on the floor next to him.

When he lowered his suit pants, Jane wasn't surprised to see how muscly his thighs and calves were, but she was quite surprised to see how large his package was as it pushed against the front of his boxers.

As he lowered his boxers Jane tried not to stare.

He was huge! Noticeably larger than any man she had been with up until this point. She had never guessed there could be so much size variation in men.

Once he had finished undressing, Tom walked across the room until he stood so close to her kneeling form that his now semi-stiff cock was nearly touching her face.

Jane at last tore her gaze from the cock in front of her to look up at Tom.

"I want you to take my cock in your mouth and I want you to make me cum" he told her simply.

She involuntary glanced down at his cock and then back at his face. His expression was neutral, merely appraising her. He wasn't forcing her to do anything, he had merely, in a very blunt way, made her aware of what he wanted. The choice still appeared to be hers.

She looked down at his cock again. This close-up it looked absurdly large and hard, and she could see all the big and small bumps along its shaft and the noticeable vein that ran down one side. The head of his cock was darker than the shaft and much smoother. She was so close she could clearly see the frenulum beneath the head and the soft reddish opening on the tip.

This was the moment of truth. She asked herself if this was something she really wanted to do? Just because Tom had asked her to do it, she didn't have to do it if she didn't want to, and she got no sense that Tom was likely to force her if she refused. It was her decision.

So, did she want to do this?

As she watched Tom's cock she saw it twitch, and felt a corresponding tingling sensation between her own legs. She was also aware of the nice warm glow of arousal that was emanating out from between her pressed together thighs.

Oh yes, she had decided that this was something she definitely wanted to do.

She then reached out and lightly grasped the shaft of his cock with one of her hands. My god it felt huge!

She had a moments nervous hesitation as she wondered if she could even get the head of his cock in her mouth, but already a more primal part of her mind was anticipating how good it would probably feel in her pussy.

With the briefest of glances back up at his face, Jane opened wide and guided the head of his cock into her mouth.

It was a tight fit, and she had to concentrate to not let her teeth drag across his length, but once past his glans she realized that it wasn't quite as tight as she had feared.

She had worriedly half expected Tom to start thrusting into her mouth the first chance he got, but for now he seemed to be willing to place his pleasure in her hands, and her mouth.

She started by caressing his head with her tongue whilst at the same time slowly stoking his shaft with her hand.

"Hmm, that's good" she heard Tom murmur from above her.

Now that she was getting used to the size of him, Jane was beginning to experience how nice his cock felt in her hand and mouth. She began to take slightly more of him into her mouth. She ran her tongue around the base of his head where she knew it was the most sensitive and was rewarded with a sigh of pleasure from above. She kept the slow caressing up for a while longer then began to increase the speed and pressure of her hand as it slid up and down his shaft.

Jane was just getting into her stride when she felt a hand rest lightly on the top of her head, followed by a new instruction from Tom:

"I want you to see how much of my cock you can take into your mouth."

Jane was slightly daunted at this command, as not only had she never experienced a cock this large before, but she had not really tried deep throating, as it had never really appealed to her. But then she reminded herself, the main reason she was doing this was to prove to herself that she was capable of taking on new challenges and experiencing new things.

With that, she leaned forward and began to take more of Tom into her mouth.

It didn't take long before she could feel herself beginning to want to gag. It wasn't a full on gag reflex yet, just an uncomfortable sensation at the back of her throat.

To give herself some control she shifted her hands so that each was reaching around and holding onto Tom's buttocks. Damn, they were as hard and as toned as the rest of his body, it was like holding onto warm stone.

She slowly eased more of him into her mouth. The gag sensation was getting stronger, so she pulled herself closer using his buttocks as leverage in order to counter the fact her mind wanted to pull away from the sensation in her throat.

A little further...

Suddenly, amidst all the emotions swirling through her at the moment, a clear thought cut through the fog of her arousal. Was she really doing this?

Only a matter of months ago her idea of sex was to lay back and accept what meager pleasure came her way, but now, she was apparently taking actual pleasure in trying to deep throat a man she hardly knew. It all seemed so surreal... but it also didn't feel wrong.

Was she losing control of inhibitions, or was she gaining control of her desires?

She heard a subvocal groan of appreciation from Tom, so for now she put away her musings and went back to concentrating on the challenge she had set herself. The urge to stop and pull back from his cock was almost overwhelming, she was seriously on the verge of gagging hard now as she felt the head of his cock at the back of her throat, but at the same time she just wanted to try and fit a little more of him into her mouth.

"Hmm, that's very good, just hold it there for a moment."

She tried to hold on, but the gagging sensation was getting stronger by the moment.

Just when she didn't think she could last any longer, "Ok, you can back off now."

She immediately withdrew her mouth fully from his cock and gasped for air.

After she had taken a few deep breaths, she heard the next command from Tom:

"That was good, now do it again."

Surprising herself, Jane found that she did want to try it again and not just because it had pleased Tom, but also because she wanted to prove to herself that she could take more of him on her next attempt. So, with one last deep breath, she guided his cock back into her mouth and began to ease herself down that magnificently thick shaft.

Almost immediately she could feel the beginning of her gag reflex start up again, but she pushed on, determined to do better this time.

She squeezed and pulled on Tom's fantastic ass as she slowly eased him into her mouth, then to the back of her throat and then a little further beyond. The sensation was unlike anything she experienced before, yes, part of it did feel unpleasant, but also another part felt amazing. She had never felt so intimately connected to a man's cock before, not even when it was deep in her pussy.

She pulled herself a little further forward until she reached her limit, then held it there. Part of her mind was freaking out, she couldn't breathe, the need to gag was overpowering, but she held position, just a second more...

She pulled away from Tom quickly and did begin to gag quite strongly. It took a few seconds before she could catch her breath and when she looked up at Tom's face her vision was slightly blurry with tears even though she wasn't crying.

Jane had already assessed that Tom wasn't a very emotional person, and he certainly wasn't good at sharing what little emotion he had, but she was sure she detected a pleased and possibly even an impressed look to his half smile as he looked down on her. The thought of his approval pleased her a lot more than she thought it would have.

"Very good, now make me cum."

With that simple instruction from Tom, Jane found herself eager to comply, as if she was determined to show that she was up to any challenge he might give her.

She immediately took just the head of his cock back into her mouth and began caressing it with her tongue whilst the firm grip of her hand began stroking up and down his shaft.

Beginning slowly, but then gradually picked up speed, Jane found a rhythm that she felt she could sustain for an extended time and went to work on him, listening to the more frequent noises of appreciation he was now making.

She began to move her mouth up and down his shaft in time with her hand and was soon rewarded as he groaned out loud and began to shake as warm fluid spurted into her mouth.

Not sure how Tom normally liked to finish a blowjob, Jane tried to swallow as little of his semen as possible whilst continuing to massage his twitching cock with her mouth and tongue.

Eventually Tom eased himself out of Jane's mouth at which point she sat back on her haunches, looking up at him patiently for his next instruction.

"Have you swallowed?" he asked her once his breathing had calmed.

She shook her head whilst still keeping her mouth closed.

"You may swallow it if you want to."

Jane wasn't sure if it was merely a suggestion or an instruction, however, she had never had any issue swallowing semen, so she made a show of doing it now.

Tom seemed pleased.

"That was nice. Please let me return the favour. Get on the bed and lie down."

Jane was getting used to Tom's direct manner of speech, so she did as she was instructed without comment.

As she lay on her back, naked except for her heels and her jewelry, Tom came and reclined next to her.

"Please close your eyes." Although it was spoken as a request, there was still something in his voice that carried the weight of a command.

With her eyes closed, Jane didn't have to wait long before she felt the fingertips of one of his hands lightly touch where her neck met her collarbone, at which point his fingers slowly trailed down her chest, down between the mounds of her breast, across her fluttering stomach, before lifting off just before they reached her mons.

The touch had been very light, but the sensation as his fingers left an electric trail of excitement down her body let her know just how aroused she was at this moment.

For the next several minutes Tom slowly caressed her entire body, sending shiver after shiver of excitement running through her. Tom might not be a very emotionally open person thought Jane, but his touch was surprisingly sensitive.

Soon Jane found it hard to keep a sense of calm as Tom continued to caress and tease her. Part of her didn't want these feelings to end, but another part of her now wanted nothing more than a good fucking.

Suddenly the hand between her legs stopped its circling.

"Spread your legs."

She had been so caught up in her erotic inner turmoil that it took a few seconds for Jane to realize what Tom had told her to do. However, once the message had got through the cloud of lust that was fogging her mind, she quickly complied.

She felt Tom moving and so opened her eyes to see what he was doing.

"No, close your eyes" he instructed.

She again did what she was told.

She felt Tom moving on the bed and could feel him position himself between her legs.

The next sensation she felt was of shocking intimacy as he parted her labia with his fingers. She was just coming to terms with the new sensation before she gave an involuntary yelp of surprise as his tongue slowly dragged itself over her now exposed and extremely sensitive clit. Before her mind could come to terms with what was happening there was another long drawn-out lick, followed by another.

Jane didn't even try and stifle her groans of lust as Tom continued to first draw his tongue slowly between her wet lips, before then beginning to trace circles around her sensitive nub with the tip of his stiff tongue. He then began to intersperse his caressing with a series of short fast licks on and around her clit before occasionally then sucking it hard into his mouth. Whenever he sucked hard on her clit, the sensations were so intense they never failed to draw a sharp gasp of pleasure from her.

Jane was already quivering with how intense the sensations centered on her clit were. She was no longer concerned with being fucked, she just didn't want the blissful licking to stop. Ever.

On and on Tom went, and more and more the intense feeling of pleasure grew within her.

Soon the pleasure was no longer warm and fuzzy, it was becoming an all encompassing raw pleasure that made her muscles tighten and her breath rasp in her throat as her chest heaved with exertion and lust.

She wanted to move and squirm in order for her lust to have its way with her body, but Tom was resting his strong powerful arms on her thighs, trapping her and preventing her from moving.

Still the licking went on.

When Jane finally came, she screamed out in pure ecstasy as her back arched off of the bed.

She was dimly aware that she was holding the back of Tom's head as her hips tried to grind against his face.

Once her shaking had eased and she had regained a little clarity of thought, she open her eyes and saw that Tom was sat casually at the bottom of the bed regarding her with his unreadable expression.

"Good?" he asked simply.

"Yes... very good... thank you" she managed to finally get out as she fought to get her breathing back under control.

Tom merely continued to regard her with his neutral expression.

Not for the first time, Jane wondered what made Tom tick. Initially she had thought Tom's face was expressionless, but that wasn't quite true, because she had begun to read the very slight signs of emotions on his face. Also, the way he had made her feel, spoke of a very passionate person, or at least someone who could inspire passion in others. He seemed to be a living breathing contradiction of a person - although she wasn't about to complain, not if he could give her orgasms like that.

Tom showed no sign of movement, so Jane lay back and just let herself enjoy the postcoital experience.

Then Tom spoke again.

"Are you ready for sex?"

Jane smiled at the directness of his question and then nodded to confirm her readiness.

"Get on your hands and knees facing away from me" Tom directed.

Although she was still fairly aroused, Jane was surprised that they were apparently moving to sex without any further foreplay, but then her mind turned to his magnificent cock and she turned and got onto all fours, to find out if the reality lived up to her very vivid imagination.

"Please caress yourself" Tom instructed, and then as though he felt some clarification was needed, "between your legs."

Jane was completely caught off guard by the instruction. This definitely wasn't something she had expected at all.

It wasn't as though she was a stranger to masturbation. At least she wasn't a stranger any more, she corrected herself. Over the last few months it had become her favorite bedtime activity, she even had a growing collection of toys to pick from. However, the issue was that she had come to think of it as a personal and private thing. She had never imagined the possibility of masturbating in front of somebody else.

Jane hesitated just a moment longer, then placing a hand to her mouth, she wet her fingers. Lowering her head and shoulders to the bed she moved her right hand to her pussy and slowly and gently began caressing herself.

It didn't take long for Jane to discovered that she was still more physically aroused than she had thought she was, and almost immediately her fingers slipped between her lips to circle her exquisitely sensitive clit.

She had always preferred to start by tracing slow gentle circles slightly away from her clit, far enough away that the initial stimulation was very faint, but close enough that the stimulation from her touch could just be felt in her most sensitive spot. Very slowly, never rushing, her touch would gradually begin circling closer as her arousal began to rise.

Her fingers continued to circle and her sighs became deeper.

By the time her fingers were circling close to her clit, Jane found she was in a state of bliss, she had almost forgotten that she wasn't alone as she continued to enjoy her growing pleasure.

She lowered her hand until it was at her entrance and slowly pressed first one, then another of her fingers inside of her.

Oh fuck that felt amazingly good. Even though she suspected that she would be wet, she hadn't anticipated quite how wet with arousal she was.

Reluctantly removing her fingers, she went back to circling around her clit. The intensity of her touch was now different due to her slick fingers. She could now rub herself harder and faster without the intensity becoming too much and as a result the sensations felt as though they were sinking deeper into her body. It felt pretty fucking fantastic.

Lost in her own growing pleasure, Jane barely registered the feel of the bed moving behind her, but suddenly she gave a startled yelp of surprise as she felt two powerful hands firmly grip her bare hips.

"Don't stop" came Tom's calm voice from behind her.

Jane had a moment of mental dislocation as she again realized that she wasn't alone. However, even without Tom's encouraging words, her body practically demanded that she continue pleasuring herself. Her body was currently so full of wanton desire and need that she thought she would probably have gone back to rubbing herself even if she was being watched by a roomful of people.

She tried to start again slowly, but her desire soon overtook her, and her fingers were soon racing her towards her inevitable climax.

Without warning she suddenly felt something warm and hard pressed up against her now very wet entrance, however she didn't stop her strumming fingers as the pleasure began to take on a life of its own.

Jane cried out as Tom began to push himself into her. The dual sensation of cock and fingers was intoxicating and clouding her ability to think straight.

As Tom continued to ease himself into her with excruciating slowness, she felt a slight stinging tightness as her pussy had to stretch to accommodate him. She had previously only thought that his was the biggest cock she had ever seen, but now she knew beyond doubt that it was the biggest she had ever had. She could feel every inch of him as he pushed into her, his maddening slowness in complete contrast to her fast fluttering fingers.

Jane was gasping hard now, and she wasn't sure if it was because of the pleasure centered on her searingly sensitive clit or the effort of accommodating Tom's large cock.

Tom began to slowly ease back out of her pussy and the passage seemed marginally easier, probably because his cock was now coated in her wetness.

Once the head of Tom's cock was at her entrance, he pushed into her again, but a little faster and harder this time. The passage was a little easier, but even the slight increase in speed and force of his cock had Jane biting her lip as she felt herself stretched out once more.

Tom's next stroke was a little faster and the one after that faster still.

Jane was beyond the ability to think straight, but her fingers needed no guidance, they knew exactly what she needed as they continued to rub her clit as hard and as fast as they could.

Suddenly Jane's whole body exploded with blindingly bright pleasure as her orgasm tore through her.

Her whole body shook as she cried out at the release of so much unbearable pleasure.

She was aware of her inner muscles trying to clamp down on the massive cock within her, the effort of which sent new spasms of euphoria racing through her body.

Jane half collapsed on to the bed as she continued to be shaken by her orgasm's aftershocks. She would fully have collapsed on the bed, but Tom was still holding onto her hips.

As she fought for breath, she could feel the pounding of her heart in her chest and her still spasming pussy. Jesus Christ. She was sure she had never come so hard in her life. She was exhausted.

As the waves of pleasure coursing through her body began to lose some of their intensity, she became aware that although Tom had slowed the pace and force of his thrusts, he was still slowly moving within her.

The slow movement of his cock within her seemed to prolong the pleasure of her postcoital bliss without intruding upon it.

Jane sighed contentedly at how good she felt at this moment. She didn't want the feeling to end, so she simply gave herself over to it, letting the pleasant sensations continue to wash over and through her.

It took a few seconds for Jane to realize that Tom still wasn't stopping his movements, if anything he was slowly beginning to thrust slightly faster within her.

"Tom...?"

"Quiet. It's my turn now" he told her in his emotionlessly calm voice.

Surely he couldn't be serious? She was still experiencing the aftereffects of her last orgasm. She wasn't ready.

But then she felt his grip on her hips tighten as he pulled her onto his next thrust.

Jane cried out as her still over-sensitive nerve endings were subjected to Tom's large cock sliding hard within her.

She bit her lip as she felt his next thrust, unsure if the ecstasy was mind-blowingly good or too much to bear.

But Tom was only just getting started.

The sensations raging through her were some the most intense she had ever experienced during sex. Soon it seemed the whole of her existence was reduced down to just her pussy and Tom's hard thrusting cock.

But then she felt a new sensation join the mix.

She could feel something circling her sensitive anus. She wasn't sure, but she suspected it was Tom's thumb. Whatever it was, it was producing a new set of thrilling sensations within her.

She gasped all the harder as the sensations within her built up. Then shockingly, the thumb started to push into her anus.

Her mind was in turmoil. She wasn't sure she wanted it to happen. She had never imagined it happening. But mixed with the sensations of Tom's cock the new shockingly erotic sensations coming from her anus had her gasping for breath.

And then she let out a small cry of pleasure as the thumb began to move in and out. It wasn't much, just fractions of an inch, but the effect was magnified with what was happening to her pussy.

With the added stimulation, Jane was soon on the verge of another orgasm, although she was desperately trying to hold it off. She now had the strong belief that even if she did cum again before Tom, he wouldn't stop or even slow down until he came. And she didn't think she could endure that extreme level of ecstasy.

So she hung on. Trying to control her breathing. Trying to resist the strong temptation of putting her hand back between her legs again.

And still Tom kept thrusting into her.

It was a losing battle for Jane. Her body was still too sensitive, his cock too good, his thumb too stimulating. She couldn't hold on much longer.

And then she came... again... hard... very hard.

As her body shook uncontrollably, the sensations were so intense that for a brief moment she could only think in colors, words were completely beyond her. She gradually became aware of being able to hear distant screams of pleasure, only to realize that it was her.

From somewhere she had found a pillow and had buried her face into it in a fruitless attempt to stifle her screams of ecstasy.

And still Tom's cock thrust into her. It hadn't even slowed.

She was just trying to find the energy to beg for a rest when she heard Tom bellow out a shout of release from behind her.

Jane cried out in relief when she felt Tom cum inside of her.

There were two more extremely powerful thrusts from Tom as he finished cumming. Then without warning he simply let her go.

She fell on the bed in a heap of limbs, sweat and sexual fluids. But despite having to fight for breath and her heart feeling as though it was going to burst from her chest at any second, she was smiling. That was without doubt the greatest fucking she had ever had.

For a few minutes she just lay where Tom had dropped her, unable and unwilling to move, afraid any movement of her highly over-stimulated body would be too much.

Finally, Jane managed to turned onto her back and continued to try and calm her breathing. Tom lay beside her, his hands casually clasped behind his head as he appeared to calmly contemplate the ceiling. For all of his efforts and the apparent forcefulness of his own orgasm, he now appeared calm and relaxed, he wasn't even breathing hard.

Normally Jane liked to cuddle after sex. She found the feeling of being close to her recent lovers and being held by them was comforting and it had always helped her to relax and appreciate the intimacy they had just shared. However, she got the sense that Tom was not the cuddling type, so she merely lay on her own side of the bed and tried to come down from her sexual high by herself.

At first it seemed a little awkward, the way they were just lying side by side in their own personal space, despite the fact they had just been as intimate as it was possible for two adults to be, but after a while she drifted off into her own thoughts.

She reflected on how strange this evening had been. Sex with Tom had probably been the most extreme, if not the greatest physical sexual experience of her life. But at the same time the whole encounter had largely been devoid of emotion, at least as far as Tom was concerned. She didn't hold it against him, as she had come to realize that was just the person he was. He certainly wasn't callus and she suspected he wasn't uncaring either, in fact she suspected he might actually be quite a sensual person, he just didn't possess the ability to express it.

It was like now, judging by his composure, she suspected that as far as Tom was concerned, this evening's encounter was effectively concluded. But he hadn't said anything, instead giving her the space and time she needed to work it out for herself. Although he was very direct in his manner of speech, maybe even blunt, she suspected in his own peculiar way he couldn't abide rudeness, either in himself or others. Therefore, he patiently waited for her to be ready.

Jane glanced across at Tom and was surprised to see that he was looking at her with a faint happy and affectionate smile. However, no sooner than she saw him looking at her, he turned to look back up at the ceiling, an odd look on his face, almost as though he was embarrassed that somebody had caught him showing emotion.

Jane felt a slight pang of pity for Tom. What had made him so afraid to show emotion? He was obviously a sensitive person, it was just a shame that it was likely that most people didn't even suspect it of him.

After taking as much of a rest as she needed, Jane turned to Tom.

"Tom, I've had a fantastic evening, but I think it's time I should be going."

Tom hadn't moved or spoken up until this point, but his reply was instant, "Ok."

As Jane swung her legs out over the side of the bed in order to retrieve her clothes, she felt the bed move on the opposite side. A quick glance over her shoulder confirmed that Tom was getting up as well.

She busied herself by getting dressed and it wasn't until she was reaching behind to try and locate the zipper on her dress that she glanced across at Tom. Tom was now wearing what appeared to be a plain silk robe that was tied at his waist, he wasn't doing anything except watching her and waiting patiently for her to finish.

Given that a strange man, who she had met only a couple hours before, was silently watching her dress, Jane surprisingly didn't feel intimidated by the experience. Given his physique and blunt manner, she suspected Tom could be very intimidating if he wanted to be, but she didn't get the slightest sense that he wanted to be intimidating to her, he was just waiting for her to finish dressing.

When she had finished, Tom silently led her back down to the front door.

At the door Tom addressed her,

"You were good company. You did as I asked without questioning me", She guessed this was high praise indeed from Tom, "If you wanted to meet again, I would probably be inclined to agree to it."

Jane smiled to herself, he certainly had an odd way of expressing how much he had apparently enjoyed her company. She was about to bid him goodbye when a thought struck her - despite how mind-blowingly awesome the sex had been, She didn't remember her and Tom actually kissing during the whole encounter... well, not on the lips.

"Tom, would you mind if I kissed you?"

Tom looked a little puzzled, "Do you want to?"

"Yes, if you don't mind, I'd like to kiss you" she responded kindly.

There was another pause, then "OK."

Jane took a half a step towards him and despite wearing heels, she had to raise up on her toes in order to kiss him. At first she didn't think he would respond to her kiss, but just as she was about to stop, she felt his strong hands on her waist as he pulled her closer and finally let some of his repressed passion enter their kiss.

Finally, the kiss ended and she took a step back.

"Thank you for a fantastic evening Tom, I really enjoyed it."

There was the briefest flicker of happiness across his face before it quickly disappeared.

Then, as he regained his composure:

"You're welcome" he replied simply, then he shut the door.

********

Jane couldn't wait until Monday to discuss her highly unusual date with Tom, but before then she had some serious thinking of her own to do first.

With Kim's help she had started on this journey to become more confident in relationships and to take charge of her own happiness and pleasure. So what did it mean that she had so willingly given up control to a man she had just met?

Was this a betrayal of her goals? Was she sliding back to becoming the malleable submissive woman she had once been?

But the more she thought about her encounter with Tom, the more she knew that this wasn't the case.

Yes, she had ceded a certain amount of control to Tom... but it had been on her terms.

So, the next question was, having gotten so much pleasure from the encounter, did this mean she was always going to be submissive by nature? Although this would explain a lot about her past life, she wasn't sure she liked this implication, if true.

But it didn't take much thought to realize this wasn't true either. When compared to John, who always took from her and never gave anything back, the encounter with Tom was all about mutual respect. Also, despite being an emotional recluse, Tom had been far more compassionate than John had ever been.

So why had she allowed herself to be submissive to Tom? The only answer she could think of was, that in that situation, in that moment, it had been exciting for her.

So, if she had enjoyed the romance of Justin, but at another time she had also enjoyed the dominance of Tom, did that mean that arousal and pleasure were dependent on situation and mood?

Hmm, this was a lot to think over. Discussing it with Kim was now an imperative.

Monday at work:

"It was strange." began Jane.

Kim leant forward with interest, "What, the date or the sex?"

"Well, both actually."

Now she fully had Kim's attention, "Ok, so tell me everything, and no leaving out the juicy bits."

So Jane told her everything, from what Tom was like, his way of instructing her to do things, how it made her feel and of course what the sex had been like.

By the time she had finished, Kim was bright eyed with excitement, "Fucking hell that sounds hot. He sounded like a real Dom... and you his willing servant." She grinned at Jane.

"No, it wasn't like that. Not really." Jane was still trying to sort out how she felt about the encounter, "He was very blunt in how he talked and very clear in what his demands were... but, well, I always had the sense that it was my decision in the end."

"So you did it because you wanted to?" asked Kim, still excited but also very curious.

"Yes", Jane had already worked that much out for herself.

"You wanted this strange man to dominate you?" Kim asked with a little smile of mischief.

"Well, maybe that was part of it." This was the bit Jane had been having trouble working out for herself. "Sure, that side of it was a turn on, but there was something else. Knowing it was my choice to give Tom what he wanted or not to give it, well, it made me feel like I had a bit of power over him too. Look, I know how it sounds, but obeying him, on my terms, it sort of felt empowering. Weird eh?"

Kim was actually thoughtful for a moment, "Not really. It was a bit of an extreme situation, but when you boil it right down, that sense of power you felt, it was because you were making decisions about what you wanted. That was really what it was about."

Jane was amazed, that was a surprisingly sensitive and insightful assessment from Kim.

"Yes," said Kim, "You thought, how hot would it be for this monster cock to face-fuck me? Come get it big boy!"

Hmm, perhaps she had spoken too soon. The real Kim was never far beneath the surface.

As Jane pause for reflection, Kim snatched up Jane's phone and began typing.

Personal space was another concept Kim either didn't understand or just plain ignored. She had also wheedled Jane's passcode out of her weeks ago.

"What are you doing?" ask Jane casually.

"I'm copying Tom's contact details of course. He sounds like the sort of person I need to meet."

"If you do see him, you be nice to him, he's sensitive" replied Jane slightly defensively. Despite his odd manner, she had actually quite liked Tom.

Kim merely raised an eyebrow in Jane's direction and then went back to typing on her phone.

There was something else that Jane wanted to discuss with Kim. She knew Kim wouldn't be shocked about it, but she found it a little embarrassing to discuss.

"Um, Tom did something else whilst he was, you know, having sex with me from behind."

Jane's hesitant statement drew Kim's focus like a tractor beam.

"Yes?" Kim was giving Jane her full attention once more.

"Um, yes, whilst he had his cock in me, he sort of also put if thumb into my bottom." A few months ago, Jane couldn't even imagine the possibility of discussing such a thing, let alone having it happen to her. But the things that she had felt when Tom had done it... well, it was just hard to explain.

Kim was now grinning from ear to ear, "Did you like it?" she asked bluntly.

"Well, I wasn't sure at first, but it was well... sort of different, it was a bit exciting and... yes, it felt good, especially when he started to move it around."

"I take it you've never done anal before?" It was actually more of a statement from Kim than an actual question.

"No!" replied Jane with a bit more forcefully than she had intended.

"But you would like to?" Kim really was curious now.

"I'm honestly not sure" replied Jane, "I've never even thought about it before. But there was something about the way Tom touched me. It felt thrilling. But full-on anal sex? I'm not really sure."

Kim looked surprisingly serious for a moment, "Look, some women like anal sex, some don't. It's just a preference. Personally, I love it. However, it's not the sort of thing you want to be trying with a first-time partner... That said, if you ever did want to try it, let me know as I might know somebody that could help."

Jane still wasn't sure how she thought about the whole anal play / sex business, but she thanked Kim for the offer anyway.

She again had a lot to think about.

********

Chapter 5 - Coming From Behind

A few days later Jane did something that she had never done before. In fact, up until recently she couldn't even imagine herself doing it. What she had done was to speak up in an office meeting. Even more surprisingly, what she had said was "No."

She had been asked to sit in on a meeting that was to discuss the company's new satellite launch strategy, specifically the systems related to payload stability. She had guessed that she had been invited because she had worked in that field for such a long time, and was probably just there just in case any of the important people had any technical questions. Certainly not because they wanted her opinion.

But the more that she listened to what was being discussed, the more she realized that these managers were talking themselves into making a huge mistake. Their new "radical" idea had been tried before in the past and had failed spectacularly. Unfortunately, the managers present were all too new that they weren't aware the idea had been tried before, so they thought "their" idea was going to revolutionize the company.

If only there was somebody here that could tell them about the problems in their plan.

With a sinking feeling Jane realized that there was a person here that could warn them of their mistake.

Unfortunately, that person was her.

She tried to look inconspicuous, to try and tell herself that it wasn't her place to speak up. But the more the other's talked themselves into this half-baked plan, the more the knot of nervousness grew in her stomach, until finally...

"No."

By shear bad luck, the moment she chose to speak up was the moment that everyone else chose to stop speaking. So unfortunately, everybody heard her.

Even more unfortunately, every person in the room then turned to face her.

"I'm sorry, you said something?", asked the CEO at the head of the table as he stared right at her.

Jane felt physically sick at being the center of so much attention.

"I said no... it wont work."

There was general muttering around the room and more than a few people glanced nervously at the CEO.

"Why not?" he finally asked.

She tried to read the older man's expression, but she couldn't, he was unreadable.

Taking a deep beath and wishing that she had kept her mouth shut, Jane started to explain the flaws in their plan. She started hesitantly, but the more she spoke the more confident she became, after all, she was just explaining the technical aspects of the problems, something she knew very well.

At one point she was nearly thrown off her stride when somebody asked, "So how would you do it?". Luckily, she was so far into the zone of technical explanation that she was quickly able to sketch out an outline of a new plan, a better plan.

Finally, she stopped talking and again realized that everyone was still staring at her.

There was a moment more of silence before everyone in the room suddenly burst into conversation. Everyone was urgently talking over each other, but thankfully she appeared to have been dismissed from their scrutiny.

Jane sat quietly for the rest of the meeting whilst her betters discussed the merits and disadvantages of the plans.

She just hoped that she would still have a job by the end of the week.

********

A week later and Jane still had a job. The meeting now felt like a distant but unpleasant memory.

She and Kim were sat in the park eating their lunch and just chatting about who Kim was currently seeing as she always seemed to find the most interesting guys.

Jane was feeling pleasantly mellow today, as she had gone on another date with Justin last night. She had told herself that she had called him, just to make sure that she wasn't slipping back into being overly-submissive after her encounter with Tom. But the truth was that she had really seen him because she wanted to.

Even now that she had other lovers to judge Justin against, he still managed to satisfy her emotionally in a way that nobody else had been able to do so far.

With her mind wandering elsewhere, Jane was caught off guard when Kim unexpectedly brought up the topic of anal sex.

A few days ago Jane had confided in Kim that maybe she was interested in trying anal sex after all, if she could find the right person of course. They had talked it over for a while, but nothing more was said about it at the time.

"So, you still interested in trying anal?"

Jane quickly glanced around to make sure nobody was in earshot, as Kim didn't seem to have a volume filter when it came to talking about topics that Jane thought were a bit sensitive.

"Um, well, I still think about what Tom's thumb felt like and I'm interest... but..."

"Yes or no?" asked Kim simply.

It was clear that Kim wasn't about to encourage Jane or talk her into it. She wanted this to be Jane's decision.

But she already knew what she was going to say. She had been thinking about it since that night with Tom. It was just that she had been reluctant to admit it.

"Yes, I want to try it." Surprisingly her voice didn't have a trace of hesitation in it now that she was finally admitting to herself it was what she wanted.

"Great!" exclaimed Kim with a grin, "So my present isn't going to be wasted after all." She handed Jane a small discreet box.

It looked like a jewelry box, about the right size to hold a bracelet or large pendant.

Jane opened it cautiously, to find nestled inside on a satin cushion, a stainless-steel butt-plug.

She looked up at Kim who was grinning manically. "I didn't bother to get you any lube because I guessed with your growing toy collection that you have plenty."

Sometimes Jane wished that she didn't find it so easy to share her most personal secrets with Kim. But on the other hand, she couldn't imagine how bad things would still be for her without her best friend.

"Um, thank you?"

"Don't mention it, and don't worry, I have your next date lined up for you as well."

Jane looked up at Kim sharply.

"Don't worry, he's and old friend of mine and just happens to be extremely gentle when it comes to anal sex. You'll like him." She finished with a wink.

Seeing that Jane still didn't look convinced, Kim carried on.

"Look, I said you shouldn't trust your ass to some random stranger, and Peter - that's his name by the way, is a sweety. He'll be gentle. Just what a girl needs for her first time. That is if your really do want to go through with it?" For a moment Kim had become serious again.

"Yes, I do want to try it, I was just a little caught out by the suddenness of it." Then she remembered her present, "So what's this for?"

"Glad you asked" replied Kim, all semblance of seriousness instantly dropping from her. "A virgin ass like yours takes a bit of warming up to the idea of things going in as opposed to just coming out. So, the plug is to help you get used to the feeling of it before your date. What I would suggest is that you practice with your new little friend between now and then just to get used to it, and for the love of god, use plenty of lube.

So now you have confirmed your up for it, are you free next Friday evening?"

Jane confirmed that she was.

"Great, I'll let Peter know."

********

Jane met Peter at his apartment as he had suggested a dinner date would be a good way for them to break the ice.

When he had opened his apartment door to her, Jane was surprised to see that Peter appeared to be charmingly normal. She wasn't sure what she had expected, but this slightly built, neat and tidy man with the big, faintly shy, smile wasn't what she had imagined.

She had been thinking about anal sex all week and in her mind it had become something that was exciting and daring, maybe even a bit extreme, and performed by exciting people who were also a little on the extreme side.

A description that really didn't seem to apply to Peter.

"Jane? Pleased to meet you. Please come in."

Peter showed Jane to the main room and offered her a drink.

Whilst he was off getting her wine, Jane looked around the apartment. It was obviously homely and comfortable, but also very neat and tidy, but in a quite relaxed way. In short, a perfect reflection of its occupant.

When Peter got back he handed Jane her drink and took a seat opposite her with his own drink.

"Dinner shouldn't be long; I've just got the joint resting before I carve it."

Peter had already checked that Jane hadn't any special dietary requirements and that she would be OK with the beef and light salad that he had proposed.

"So, how long have you known Kim?" asked Jane looking for a way to get the conversation started.

Peter gave a brief laugh. "A few years now. We met through a dating app."

Jane suspected as much, although Peter didn't seem Kim's normal type. Judging by her stories Kim seemed to favor people that could match her high levels of "enthusiasm." As tactfully as she could, she mentioned this to Peter.

This time his laugh was much fuller, and Jane found herself liking the sound of it. Peter had an honest laugh which seemed to reflect his natural sense of humor. "Kim doesn't like to admit it, but she does have her sensitive side and sometimes likes to indulge that side of her with someone that wont make demands of her. And sometimes, well, occasionally, when I'm in the mood, I like things a little more "exciting", and I'm sure you can imagine where Kim helps with that." he finished with a grin.

"And you don't mind that she sees other people?"

"Of course not" replied Peter, as though the idea had never occurred to him. "We are just friends. Friends who sometimes have needs which the other one is able to help with."

This was something new for Jane to think about. With the possible exception of Justin, she didn't think that any of the dates she had been with had seen her as anything more than a one-off opportunity for sex, and if she was being very honest with herself, she had felt the same way about them.

Jane was still thinking about this when a little later Peter announced that dinner was ready.

As Peter held Jane's chair for her to sit, he commented on the small meal laid out before her. "Just so you don't thing I'm stingy on my portion size, I thought with what we, ah, might be doing later, it would probably be best if we kept things light."

Jane could see the sense in this, and although what Peter had prepared looked and smelt fantastic, she wasn't overly hungry due to nerves.

The conversation during the meal was very pleasant and relaxing, Peter was an easy person to spend time around. Although the conversation did occasionally dip into topics that didn't normally come up in other dinner dates she had been on.

"So, Kim tells me that you don't really have any experience when it comes to anal sex?" It was a testament to Peter's easy going and pleasant demeaner that the question wasn't as shocking as it might have been any other time. As a result, Jane wasn't embarrassed to answer honestly.

"No, not really, not full on sex certainly. Although I have been practicing with a butt-plug for the last week."

"That's good to know. Anal sex can be a little challenging, if you aren't prepared. How did you get on with it?"

In fact, the little metal butt-plug was Jane's new favorite toy, especially since she had discovered how it could really enhance her enjoyment of all of her other toys. The thought of how strong the sensation was as she felt her muscles grip that unyielding piece of metal in her backside during orgasm sent a thrill through her loins even now.

She had even worn it to work a few times. Each time she had worn it in public, the stimulation had been as much mental as it had been physical.

"Um, I like it." she replied, still a little self-conscious to admit just how much she really liked it. "It was a little difficult to fit it in the first couple of times even with plenty of lubrication. But once I learnt to relax it became easier."

"It sounds like you've made a good start." Peter was thoughtful for a moment, "You know, I've never done this before."

Jane was shocked, "What, you've never had anal sex before?"

This time Peter's laughter was full throated, "Oh, I've done that plenty of times. No, I meant I've never been asked to be somebody's first time before, at least not on a blind date."

There was a brief pause before Peter spoke again.

"Which is why I just want to be sure that this is really what you want."

Despite the excitement that had been growing within her all week, Jane took the time to really ask herself if this really was something she wanted.

Finally, she looked at Peter, matching his gaze.

"Yes, I want this." There was clear certainty in her voice.

******

They were now in Peter's bedroom, although neither of them seemed too certain how to proceed.

Unlike her other dates, where a certain amount of sexual tension was present right from the start and built up throughout the evening, culminating in (hopefully) great sex, Peter had come across almost like a friend, so there hadn't been any sexual tension, despite the topic of some of their conversations.

"I was thinking, it maybe easier if we start with something non-sexual first. Maybe a massage?" suggested Peter.

"Sounds good."

"OK, if you want to get undressed and lie on the bed, face down, I have some things I just need to sort out." Peter left the room.

It was whilst she was getting undressed that Jane suspected that Peter had only made an excuse to leave the room, probably to give her some privacy whilst she undressed. On one level, it seemed odd, given the purpose of this encounter, but Jane found it endearingly considerate.

Once undressed, she got on the bed and lay on her front, her head resting on her crossed arms.

She didn't have to wait long before she heard soft footsteps crossing the bedroom floor, then a shifting of the bed as Peter joined her.

"Ready?" he asked.

"Um Hmm"

A while later, Jane thought to herself that Peter could probably do this for a living, he was very good.

Despite them both being naked, (she had snatched a quick look to be sure), and him caressing her all over her body, there hadn't been anything sexual in it, instead he had made her feel incredibly relaxed.

But then imperceptibly, something changed and now Peter's touch was a little more sexual as he slowly began to explore her slightly more sensitive areas.

But then his touch became more sensual still and she felt herself becoming hotter and more aroused.

Peter was now exploring high up on her inner thighs, with the occasional caress over her vulva.

Hmm, Jane was now somewhere between extremely relaxed and highly aroused... and it felt great!

As Pater's fingers of one hand started to caress her vulva with slightly firmer touches, his other hand was gliding over her bum and taking the occasional detour down between her cheeks. Each time his hand lightly glided over her anus, she felt the breath catch in her throat.

At one point Peter paused his caressing and asked Jane to get onto her knees but she could keep resting her head on the bed if she wanted. As she knelt in position, Jane heard the distinctive snap of a plastic bottle cap. The next thing she felt was a pair of slick fingers gliding between her labia, stimulating the soft sensitive skin beneath.

She was just getting used to the increased stimulation, which was already causing her to sigh deeply, when she felt another slight shift in the bed. She had a fraction of a second warning as she felt hot breath on the soft skin between her butt checks, when suddenly and shockingly she felt a hot wet tongue lick right over the top of her extremely sensitive anus.

Caught completely by surprise, Jane let out a yelp of surprise. But it wasn't just the surprise that had made her yelp. The feel of the wet tongue on her hot and sensitive little hole had sent a jolt of pleasure right through her lower body.

But that was just the beginning.

Peter began to set up a rhythm that seemed tailor made to excite every nerve ending in her pussy and bum, which soon left Jane breathing hard.

The slick fingers gliding between her labia was great, although most of her focus was being drawn to the exquisite feelings emanating from her anus as Peter's tongue circled, licked and prodded her anus. Each time his tongue prodded at her entrance, she couldn't help but gasp.

She really was floating on wave of growing arousal when Peter paused again.

"Do you think that you are ready to try a finger?"

Immediately she knew what he meant and immediately she knew that she was more than ready.

"Yes." She breathed.

Another pause, another snap of a bottle cap, and then she felt something firmer but just as slippery circling her anus.

Peter's finger was noticeable stiffer than his tongue and he was pressing slightly harder as he began circling her rosebud.

She felt her anticipation building as his finger began spiraling in towards her entrance, her breath catching as she felt the sensation shift from pressing on her anus to being at the point of pushing inwards.

"Are you ready?" he asked gently.

Oh, she was much more than ready, and told him so.

Jane's breath came out in one long drawn out sigh as Peter's slick finger began to push into her.

He moved slowly and gently, pausing often to check that she was alright, but eventually his entire finger was snuggly embedded in her anus.

When Peter at last began to move his finger inside of her, Jane let out a low guttural moan.

His finger wasn't as wide or hard as her butt-plug but having something moving within her felt infinitely more intimate.

Long minutes of intimate internal caressing followed, in which Jane learnt a whole new range of exciting sensations.

Jane felt a soft kiss on her lower back and then Peter asked, "Do you want to try the next step."

By this point Jane guessed there was only one more step and by this stage she knew that she not only wanted it, she needed it.

She felt Peter reposition himself behind her, then his finger was back, except it was moving more systematically than before as it spread slickness around and within her anus.

A movement, a hand on her hip, then something was pushing against the entrance to anus.

It was softer than a finger, but noticeably much bigger.

Peter was very gentle but Jane still gasped as she felt the head of his cock pressing against her entrance. By the time the head of his cock was most of the way into her, she knew for sure that his was much thicker than her little sleek butt-plug.

Peter paused his forward advance and just held where he was, just making fractional movements back and forth to allow her muscles time to adjust.

After a pause, "More?" he asked.

Despite feeling far more stretched than she had ever felt in her life and despite the slight stinging sensation she could feel, Jane nodded her readiness.

Over the next few minutes Peter moved slowly deeper and deeper into her, stopping often to let her and her muscles get used to the new sensations she was feeling.

The point when Jane felt Peter's hips make contact with her bum cheeks brought a sense of elation to her as it signified that he was now fully inside of her. The sensation was almost beyond her ability to express. The sense of fullness was expected, but the tightness in her muscles and nerves were giving her sensations the sort she had never felt before.

After pausing, Peter began to just as slowly withdraw from her.

The passage of his cock as it withdrew was easier but no less stimulating as her muscles gripped and slid along his firm length.

Slowly, Peter started to set up a rhythm. Each stroke just a fraction faster than the one before. Even then he would pause occasionally to ask if Jane was OK, but within a few minutes Jane was rocking her hips back to meet Peter's thrusts.

Not even her cherished butt-plug had prepared her for sensations on this level.

Soon she was gasping at the intensity of her feelings, she felt on the edge of cumming but couldn't quite reach the next stage that would take her over the edge into orgasmic relief.

The pleasure was incredible, the imagery of what was happening to her was extremely erotic and arousing... but it wasn't quite enough.

Underneath all of that fantastic pleasure and erotism, there was still something holding her back. She was now taking Peter more easily, especially after his liberal application of lube, but she still wasn't relaxed enough that there wasn't just a faint stinging sensation due to how tight she was. It was this infinitesimal amount of discomfort that was holding her back.

But Jane was too far gone to stop.

From her kneeling position, she reached up between her legs and began to massage her clitoris. She started slowly, but soon her movements became frantic. Together with the feelings that Peter was producing in her ass, her fingers had jumped her over the last hurdle of her resistance and was now hurtling her towards an explosive orgasm.

As she came, her whole body tensed up with the extreme emotion she felt. The feel of her anal muscles clamping down on Peter's cock had all her muscles quivering like never before.

Jane felt that Peter had stopped thrusting inside of her and was just holding position, fully inside of her. In a fanciful thought she wondered if he wasn't moving in order to giver her time to experience her first anal orgasm, or was it the fact that she was clamping down on him so hard that he couldn't move?

But eventually she did relax and Peter finally withdrew and lowered her gently to the bed.

As soon as Peter was lying next to her, Jane gathered him into a hug and thanked him with kisses.

"Well, what did you think of anal sex?" he asked once Jane had finally released him.

"It was different, but good, very good. Really erotic... and thank you. You were really gentle and I was glad you were my first time... well, with anal at least." she finished with a smile.

Peter blushed slightly at the compliment, "I'm glad, because I enjoyed it as well."

After a pause, "After I've had a chance to catch my breath, can we go again?" even the slight stinging sensation she still felt couldn't dampen Jane's excitement at having experienced something so new and erotically stimulating. "That first time was so overwhelming, I'm not sure I had a chance to fully take it all in."

Peter grinned, "Sure, whenever you're ready."

The second time that Peter entered her delicate little rosebud, Jane was on her back with her thighs pressed up against her chest. And this time she didn't need her fingers to make her cum. In this position, Peter wasn't penetrating Jane quite so deep, although the increased tightness and accompanying fullness she felt more than made up for it. Additionally, being able to see his face contort with effort was the final thing that she needed to tip her over into orgasm from anal sex alone.

After her second anal orgasm, Jane felt she was a little too sore to go again, even though a part of her really wanted to, but another thought had occurred to her.

"Peter?"

"Yes?"

"Is there anything I can do for you?"

"What do you mean?"

"Well, all evening you have been concentrating on my pleasure and making me feel good. So, I was wondering, is there anything special I can do for you that would make you feel especially good?"

Peter paused for a moment, thinking, "Well, there is something, but only if you really wanted to" he actually sounded a little embarrassed to ask, which Jane found quite charming, especially considering what they had just been doing, "Um, well, I do like it when a woman rides me on top, and well... uses me just like a... sex toy. As if I wasn't really there, just my cock. And they just used me for their pleasure.... I know it sounds weird, but do you think that is something you might want to do?" he asked in a hopeful voice.

Jane was already moving to get on top of him, a wide mischievous grin on her face, "Oh, I think I can manage that." she said with relish.

They both groaned as she lowered her very wet pussy down on onto his very stiff cock.

********

The following Monday Jane was walking quickly to Kim's office at work, eager to tell her all about the previous Friday's adventure, when she was called into her manager's office.

Oh crap, thought Jane. She bet this was about how she had spoken up in that meeting the other week and how she had disagreed with the other managers.

She hoped she wasn't about to get anything more than a warning. She was back to really enjoying her job again and didn't want to risk losing it now.

As it turned out, the talk was about the previous meeting, but not for the reasons Jane had imagined.

She was being asked to head up a new project. Apparently, someone had liked her idea and was giving her a "Put up or Shut up" opportunity. Essentially, she was being asked to back up her words with actions.

Her mind went immediately to the company's CEO. He had been unreadable during the meeting, but she had heard that this was just the sort of thing he tended to do, to in his phrase, "Weed out the bullshitters." She just never imagined it would happen to her.

She was going to be given two months to come up with a report that was to outline a new containment systems that would provide adequate protection for the new generation of micro-satellites whilst also maximizing the number that could be carried by the rockets that were currently available to them. The report would need to include an outline of the new proposed system, an estimate of timescales to implement, a high-level cost estimate to implement, as well as any likely manufacturing issues that would need to be resolved.

The thing that came as the biggest surprise though was when her manager started to discuss her staffing needs. The report was required to be detailed and comprehensive, to the point that it was expected that Jane would require a staff of three to assist her. If she could supply a list of her preferred three names by the end of the day, he would do his best to free them up for her use during this project.

More than anything else, Jane had difficulty getting her head around the fact she was going to have a staff. People were going to be working for HER?

It might only be temporary, but even so...

As soon as her manager had let her go, Jane practically ran to Kim's office. She now had TWO important bits of news for her friend.

********

A month later Jane was asked to present an interim version of her report to the board of senior managers.

Normally such a thing would have scared Jane ridged, possibly to the point that she wouldn't be able to speak.

However, on that day Jane had something much more important on her mind.

Earlier that morning she had received a tracking notice that her latest toy was due to be delivered today. It was a mains-powered wand vibrator. According to her research it was meant to be one of the most powerful vibrators on the market... and she couldn't wait to get home and find out if it really lived up to the hype.

As a result, Jane was extremely distracted throughout her presentation and really had to concentrate on the contents of her report and try to resist not thinking about how she was going to spend her evening once she got home.

It was a few days later when her manager congratulated her on her presentation.

Apparently, her presentation had gone over well with the rest of the management team, with a few people commenting on how focused and confident she had been.

If only they had known thought Jane.

********

Chapter 6 - The Next Chapter

It was now a year since her presentation to the management board and so much had changed in her life since then.

For a start, it had turned out that the project she had been given all those months ago had actually been a form of job interview and one that she had apparently passed with flying colors.

She now headed up her own section of seven people who were putting the final touches to the preparation stage for the new satellite cradle system before it went into full production. In fact, she was so busy, she might need to take on another couple of staff in order to cope the amount of CNC code that was going to be necessary for the manufacturing stage.

Jane had never imagined herself in this position. She had always known that she was good at her job, even if she had previously had difficulty admitting it to herself or other people.

Having to head up a team was a completely new experience for her and at first the thought of it had made her doubt herself once more. However, it had become another lesson for her when she finally discovered that she was surprisingly quite good at it. A new challenge taken on, a new experience gained, and she was now stronger because of it. It seemed to be the story of her life at the moment.

But the really important changes went deeper than that, her advancement at work was just a byproduct of her newfound self-confidence and commitment to be in charge of her own destiny.

Jane had gone on many more dates in the last year, and each of those dates had been a new experience for her. Each one hadn't just opened her up to new sexual experiences, although some of the experiences had been surprisingly intense, but each date had also taught her something new about herself. She was becoming more confident and willing to take on new challenges. She was also gaining a better understanding of who she was sexually and about recognizing what made her feel good and what fulfilled her.

However, there was still occasionally time for reflection. As good as the last year had been, she still looked back with fondness at what she called her "original lovers", Justin, Tom and Peter. Each of those wonderful men had taught her so much about herself and had helped break down the chains that had held her back, releasing her to become the woman that she was still on her journey to discover. Thanks to them, she had not just discovered confidence and the courage to try new things, but more importantly she had learnt that her pleasure and happiness were in her own hands.

As she reminisced, her mind drifted back to last week's encounter with Rob and Jase. Now that was an extreme encounter that had certainly taught her an awful lot about herself in just the span of a single night.

She felt a distinctive and pleasant warm glow between her legs at the thought of what had happened that night. She grinned to herself, thinking of how she had even shocked Kim with what she had gotten up to.

Thinking about Kim brought a smile to her face. The woman never stopped amazing her. At the moment Kim was currently enamored with her new boyfriend, Garry, to the extent she was actually contemplating surprising him with a threesome. In the way that Kim had confided this to Jane, Jane was almost sure that Kim had also been sounding her out on the idea.

A year ago the mere idea of an intimate encounter involving another woman, especially one she considered a friend, would have shocked her to the core.

But she wasn't that person anymore.

She had come to the belief that the giving and receiving of pleasure between two consensual adults could never be wrong. So, did that still hold true if the consenting adults also happened to be friends?

She had to admit, the thought of sharing such an intimate experience with Kim was intriguing and just a little exciting. But until Kim came right out and asked her about it, it would currently remain just the subject of pleasant musings.

Besides, she didn't have time for such idle thoughts, as pleasant as they were, because Jane also needed to give some serious thought to what she wanted to say when she met up with Justin tonight.

Jane knew that on her journey of personal growth, there was still a lot more to find out about herself, but she had also begun to wonder if Justin might want to be a more permanent part of that journey?

It could be a new chapter in her life.

A better chapter.

And to think, at one time she had actually thought her life was over.

Oh, how wrong she had been.

The End.