Jude and Sarah

I've always considered myself a pretty normal guy. I work hard during the week. Play football at the weekend and go out drinking in the pub, on a Saturday night. Just the sort of thing a lot of my mates had done, since we left school. I'm now in my late twenties. There is nothing special about me. I'm an engineer, fixing machinery in large factory. The company is huge. There are several hundred employees, in the factory, warehouse and offices. We have our own sports social club and it is the company football team, that I play for. We aren't brilliant. We hold our own in the middle of the league but we enjoy the games and a few beers afterwards. From time to time, I've managed to get dates with women in the offices, as well as some picked up in pubs after away matches.

For me, sex has often been limited to one night stands or short lasting relationships. I haven't yet worked out why. Is it my personality, or the sort of women I ended up with? Most were party girls, out for a good time. The sex was often frantic and satisfying for both of us but the novelty wore off quickly, usually on their part rather than mine. I have reached a point in life, where I was feeling the need for something more long term, permanent and satisfying.

I've been playing for the company football team for the last five or six seasons. There is always of lot of banter, both in the changing rooms and afterwards. The changing room layout varied with the fixtures. Ours, a large changing room with individual toilet and shower cubicles. A lot of the others, large rooms and communal showers. You get used to seeing the other players on your team naked. Some players were more comfortable with this than others. It's hard not to look and compare. None of that bothered me. The approach to pubic grooming and size of member covered all sorts. It just became normal to all of us.

Why is any of this important? Because it has some bearing on where my life has ended up. Where we work, has a large cafeteria, for any of the staff who want to use it. None of the people I actually work with or play football with were there, this particular day. I looked around as I ate, not having anyone to talk to. From the corner of my eye, I caught sight of someone interesting. Not anyone I had seen before. Long sandy blonde hair, cute face, slim figure and nice legs. She didn't look that tall. Her clothes not flashy, black skirt and short sleeved blouse, dark green stockings and black shoes with a small heel. She was heading for the toilets. She returned a few minutes later, walking right past me, probably heading for the offices. She smelt nice. A waft of expensive perfume.

I asked around the people I knew, to see if anyone knew who she was. The goalkeeper in our team thought she dealt with sales invoices. At least she wasn't a visitor. I didn't see her again for a few days. When I did, it was again in the cafeteria. She was sat with a couple of the women I saw sometimes at the social club. That seemed to point in a positive direction.

I would see her from time to time but it wasn't for a few weeks, that I saw her outside work. We had been playing a match at home and were in the social club having a few beers. There were a group of about a dozen women from the offices, sat around a large table, getting quite rowdy. The woman with no name was one of them. I kept a careful eye on her. Eventually, the group started to break up. A few of them left, presumably for a club, others possibly for home. Only two still there and they headed for the bar. I took my chance and walked over. I asked if I could buy them a drink. To my surprise, they actually agreed. A vodka and tonic with ice and lime, for the woman I had been watching. A rum and coke for her friend. I now had a name for the cute woman, Sarah. Her friend was Caroline.

Caroline also looked pretty nice. I'd seen her in the club lots of times. She had actually been out with one of the players on our team for a while. We were on the passing acquaintance level. She knew from the off, that it wasn't her that I was interested in but did want to look after her friend. A reasonable attitude as I had just appeared with a speculative approach. We sat and talked. Sarah hadn't been with the company long. Presumably why I had only been seeing her for a number of weeks. I knew that Caroline wasn't the party type, I normally ended up with and presumed that Sarah was the same. Probably the reason they hadn't gone with the others. Sarah excused herself and went to the toilet. While she was gone, Caroline said,

"She is not what you think. Or what you will be expecting."

"What do you mean?"

"I don't want you to get the wrong idea and be disappointed, or to upset her. Sarah is beautiful. No doubting that. She is also trans."

"You're kidding?"

"You can't joke about things like that. If you are going to walk away, do it politely."

"You probably have the wrong idea about me. Everyone thinks I'm just messing about and playing the field."

Before I had time to finish what I was saying, Sarah returned. She nodded her head at Caroline. She picked up her handbag and jacket and said she was leaving. I asked if I could see her again. She took out her phone and pinged me her number. Caroline looked stunned. I think even I had surprised myself. I had no idea, what going out with someone like Sarah would be like. If Caroline had said nothing, I would have done the same. I would probably have got a surprise later.

The following day being Sunday, I had a late morning. No need to get up early. I got on the internet and started trying to find out, about dating trans people. A lot of the search results were for porn sites. Not that helpful. With enough digging there was quite a lot of useful information and a few things I would need to ask Sarah.

A couple of days later, I plucked up courage and phoned her.

"Hi Sarah. It's Jude. I wondered if you would like to go out to dinner on Friday."

"Oh.... Sorry. I didn't think you would call. Caroline told me on the way home, that you knew about me. Are you serious?"

"I didn't call you as a joke, or as a dare. I want to get to know you. There's no harm in having dinner. If it doesn't work out, at least we will have had something to eat."

She agreed. We passed the occasional greeting if we me each other at work. On Friday after work, I paid more than usual care to my grooming and appearance. Neatly ironed shirt and trousers. I drove in to town rather than getting a taxi. I had no intention of drinking. I wanted a clear head. I would, if she was alright with it, make sure she got home safely. I'd booked the table for 7.30 and made sure I was there slightly early. She arrived on time. I ordered her a vodka and tonic, sparkling water for me, as we sat to look over the menu. We ordered with the waitress and began to get to know each other.

Sarah is twenty six to my twenty eight. She looks younger than that. She had known for some time, that she was a bit different. Her looks always feminine, had been a worry. She had eventually, come to terms with her short stature and looks.

"You can't beat nature. This is who I am. I tried to change myself. I just got angry and depressed. I decided to stop fighting and just accept it. I'm happier now than I've been for a while."

"I'm not looking to change that but you are going to have to help me. This is all new for me. It isn't something I've ever considered."

"It's pretty unusual for me too. Gay men aren't interested in me, because of how I look. Straight men find me attractive, until they find out more. Occasionally, straight women get curious."

The evening passed off pretty well, considering her initial reservation and my uncertainty, after Caroline's comments. Sarah accepted a lift home. When we arrived at her place I turned on the courtesy light. Leaning over I kissed her, strawberry lip balm? She invited me to lunch on Sunday. Again, no strings attached, just food and talk. I accepted and drove home. This would be a novel situation for me. Two dates and no hint of sex. Perhaps this had been where I was going wrong.

I left the club early on Saturday evening. The rest of the team were still drinking heavily. A good nights sleep and rising earlier than normal, I started to get ready. A wash, shave and a different look to the one at the restaurant. Slightly more casual but clean and tidy. She had asked me to arrive at noon with lunch planned for one. I obliged. Her place isn't that different to mine. Hers ground floor maisonette, small but with all she needed. Mine a small flat, in the middle of a three storey block. She opened the door and let me in.

"Would you like a glass of wine?"

"No thanks, I'm driving. A coffee or a soft drink would be great."

She poured me a glass of tonic and a small wine for herself. We sat together on the small couch. She began asking me about my past. Probably on the back of the comments made by Caroline. It appears that I have a reputation, even though I don't think it is deserved. Had I been with a guy? With my negative response, was I concerned about where this might lead? I had to say I was nervous about it. I presumed that I was like everyone else in that regard, it was something new.

After we had eaten in the kitchen diner, we returned to the lounge to continue the conversation. I don't think either of us felt comfortable discussing sex while we were eating.

She explained, that she hadn't needed or wanted to take puberty blockers. With how she looked now, you couldn't disagree with that. She is on low dose hormones, which had some relatively mild effects. One of which was slightly increased breast tissue. Only small but I had been with at least a couple of women with less. It wasn't something which was high on my priority list. Nor surgery. She didn't want large breasts. Understandable with her small stature. The thought of the results and ongoing issues with bottom surgery, had made her feel sick. She also liked the endorphin rush of having an orgasm and didn't want to lose that. I know what she meant.

"Do you know about tops and bottoms?"

"I've done a bit reading. I understand that it's about giving and taking."

"Close enough. There are people who switch between the two. I'm one of them. I don't want to make this difficult. If we take things further, it will probably be better, if I take the bottom role. At least to begin with. Does any of this put you off?"

"Actually, not as much as I thought it might. I see plenty of naked men in the showers, occasionally one with an erection. I'll admit to being curious. Although I've never done anything about it."

"Aside from the physical side of things, you will probably have to deal with how other people will treat you. Most will see you in a relationship with a woman. Some think that you are with a guy in a dress. I know I pass pretty well but it is something you need to be aware of."

"Do you still get that?"

"Not so much these days but it still goes on."

This was all a lot to take in. In some ways, I was still struggling to understand why I was drawn to Sarah. Undeniably pretty but I knew she was beneath it all, male. Yet I wasn't put off. Maybe I was just drawn to her as a person. I'm not clever enough to work it out. Late in the afternoon, I took my leave. We got up from the couch. I put my arms around her gave her a hug and a kiss. Physically, no different to kissing a woman. Emotionally, a bit odd. I could feel the unmistakable sensation of an erection pressed against my thigh. That wasn't the first thought to cross my mind. The first was, how short she was. Maybe 5'4" or 5'5" to my 6". Even for a woman, that is average. For a guy it is short.

On the drive home and that evening, I was still trying to work out how I felt. That night in bed, I had an absolutely amazing wank. My cum shot up my body, as far as my chest. My fantasy? Having sex with Sarah, in whatever form that might take. Did it feel weird jacking off, thinking about it? Yes, slightly. Would the reality match up to what I had just imagined? I had no idea. One of the party girls liked to finger my arse, when she sucked my cock. I liked it. What would it be like with a cock? What would it be like sucking a dick? A couple of the girls I'd been with choked and gagged. Others loved it. A strange thought to end the day with.

My football match the following Saturday was called off. Several members of the opposing team were sick. I decided to spend the day with Sarah. We went in to town. We held hands as we walked around the shops. We stopped for coffee. Nobody had looked at us strangely. It was just like any other date, I had ever been on. We had lunch at a cafe, at the end of which, she invited me back to her place. The implication being that things would get intimate. We got back to the car and I let her in. She asked,

"Are you going to be alright with this?"

"In theory yes. No way of knowing until we try it. I hope neither of us will be disappointed."

I was quiet on the drive back. I parked on the street outside her house and followed her indoors. I'd only been in the lounge and kitchen diner before. She went straight to the bedroom, with me in tow. Neutral decoration, plain curtains and bedding. Had I expected something more feminine? A few prints of famous art works on the walls.

She began to undress. Her flowery summer dress had buttons all the way down the front. She undid them slowly, hanging it on the back of the door. Now stood before me, the most I had seen of her, since we met. A small pink bra and matching pants. A distinct bulge in the latter. Thinking it would be odd with me fully dressed, I took off my shoes, shirt and trousers, putting them on a chair in the corner. I must have looked apprehensive. She approached me, up on tip toes and kissed me, her hands ran down my back. She reached the waistband of my boxer shorts and took hold, a hand on each side. She disappeared down my body, my shorts going with her. Normally, in this situation I would have had a hard on. With her hands, one on my cock, the other stroking my balls, it didn't take long to remedy that.

I looked down, in time to see a small, cute pair of lips slip over my knob. Strange? No. The sensation every bit as good as any oral I'd ever had. It was getting better. Ever so slowly, her lips moved closer to my abdomen, until my whole cock disappeared. No woman had ever done that to me before. Her head withdrew and she licked and sucked the tip of my knob before my cock sunk from view again. Her right hand move to my buttock holding it softly. Her left, initially holding my balls, moved slightly, a finger rubbing my anus. No attempt to push inside, just stroking gently.

"SARAH! SARAH! CU....."

Whether my warning was too late, or she had intended it all along, I came, with her nose jammed against my pubic hair.

"HUUGH!"

No gagging, my hand stroked her cheek as she swallowed. Holy fuck, that was intense. Her hand ran back across my scrotum. I let out a little sound and my legs trembled. She drew her lips back along my shaft and over my knob. I shook again. I reached down my hand and helped her up. I was still looking down. An erect and circumcised knob was poking out of the top of the pink briefs. I couldn't help, putting my hand down. Was this what I was thinking about doing? My fingers and thumb pointing straight down cupped the knob in my fingers. Slippery with fluid. Hadd she really been so turned on from sucking me? She let out a cute little sigh. Her arms wrapped around my back.

I still have my foreskin. Rubbing directly on my glans is usually uncomfortable, until I'm turned on and producing a lot of pre cum. This was different. I was careful, not to be too rough. I started dragging my fingers up and down the increasingly wet knob, my thumb brushing the thin tight skin of the frenulum. She was pushing her head hard into my upper chest. All of a sudden her hips jerked backwards, away from my hand and let out really quiet,

"Huwwww."

Cum spattered my hand and beyond onto my thigh. I don't know if this is strange or not. How many men have tasted their own cum? I had licked my fingers after wanking. I'd also gone down on one of my more adventurous partners, after I had cum inside her. I lifted my hand and licked my palm. Sarah took my hand and licked my fingers clean, used not only to her partner's cum but also her own. She looked up and asked,

"Are you alright? I wasn't expecting that. This was for you."

"I'm good. You?"

"Great."

She stood back slightly and unclipped her bra. If this was down to hormones, they were doing a good job. Cute little mounds with small, pale pink nipples. She slid down her briefs. The full extent of what I had been rubbing revealed. A cock roughly the same size as my six inches. Where I have trimmed pubic hair, she had none. Scrotum still tight and small. It was only now that I realised she was stood there just wearing her shoes. She slid them off and went to lay on the bed. I stepped out of my boxer shorts and went to lay beside her.

My mind was spinning. Not because of what we had just done but because of my own mental baggage. I had just wanked and been sucked off my another man, who looked amazingly pretty. Did that make me gay? I wasn't attracted to other men, in the normal scheme of things. In fact this was the first time I'd touched one. Was I attracted to trans women? Not really. Not many actually looked female, in my eyes. It wasn't a general attraction. Laying on my back looking up, I think I was frowning. She was on her side looking at me.

"What's wrong? Regrets?"

"No."

I explained what had been thinking.

"Demi."

"What?"

"It's called demisexual. Being attracted to someone, because you have a particular feeling for them. You felt something for me, when you thought I was a woman. Even though you know I'm not, you are still here."

I turned to face her. She moved closer and our lips met. As they did, our groins did too. The movement and perhaps the thought of what we were doing, meant that we were both erect. The incongruity of the beautiful face I was looking at and the cock rubbing against mine, was still on my mind. He small breasts rubbed against my chest. She pulled her lips away slightly, words spilled from then,

"I want you, I want you now."

She rolled away from me, opened a draw beside the bed and took out a bottle of lube. The implication was clear. I'd had anal with one woman. I find it interesting that something which is so off limits to some, is a must have for others. I actually did her arse more than her pussy. I took the bottle from Sarah.

She lay on her back, pulling he knees up. Her anus as cute and hairless as the rest of her. Above it a tight scrotum and hard cock pointing up her belly. Taking a blob of lube on my hand, I smeared it on her wrinkled hole, she let out a little squeal. Cold? I rubbed with my index finger pushing within. A sigh. More lube to ease the entry of a second finger. Yet more on my cock. I'd learned this much from my female companion. A lovely and contented smile crossed Sarah's face. Removing my fingers, I placed the tip of my knob, where they had been. Slowly, I increased the pressure. I could see her opening to accept my entry. My knob was accepted. In my mind, I'd expected this to be easy. I assumed, I was nowhere near the first. She was tight. The tension on my skin, incredible. A couple of minutes of very slight movement and my entry was eased but only slightly. A couple more and I felt confident enough to increase my movement.

My gentle thrusts causing the cock before me to twitch bounce. I reached out a hand and took hold. Forming a sort of tube with my hand, the cock fucked it as I pushed home into her arse. Never in my life, had I contemplated fucking a guys arse. Less still wanking a cock at the same time. Yet here I was, even though, in my mind I was thinking of Sarah as a woman.

I didn't last long. Not as long as I'd hoped. One more pump and jets so spunk erupted from my cock. The impact on Sarah was immediate and surprising. Her back curled lifting her bum. Cum shot out of her, up and across her face, on her cheek nose and even her forehead. I'm not sure either of us made a noise. If we did, we didn't notice. Caught up in the sensation of a couple of massive orgasms. Sarah continued to shake. I eased my cock out. For some reason, I can't explain, I bent forward and took the knob of her cock in my mouth and licked the opening at the tip. She bucked, pushing several inches of cock into my mouth.

Lifting myself up, I moved up and over her body, hands either side of her shoulders. I lowered my head and kissed her lips. The aroma of cum filled my nostrils. Despite all that we had done, it was still early. Late afternoon or maybe early evening. Raising myself up, she had a really cute looking smile on her face. She mouthed a silent thank you. We had both cum twice and Sarah was covered in it. I shuffled over and lay beside her. She rose,

"I need a shower. I'll sort you out some things."

She disappeared for about ten minutes. When she came back, her body wrapped in a towel, another in a sort of turban round her head. She handed me a towel.

"Sorry but all of the shower gel and shampoo is a bit feminine."

I went to the bathroom and took a shower. She was right. I came out smelling of roses. I really didn't care. She was sat on the edge of the bed, when I got back to the room. She stood up, dashed over and wrapped here hands round my neck. All of a sudden she jumped, hooking her legs behind me. I grasped her bum, in case she fell.

"That was great, Thank you so much...... I wasn't expecting you to..."

"I wasn't expecting me to either."

"You can stop groping my bum now."

I let go and she slid back down to her feet. She gave her hair a rub with the towel before draping it over the post at the foot of the bed. She undid the towel round her body and did the same. It was the first time I'd seen her from the rear. Her bum looked so small and cute. Pale and soft. She went to the chest of drawers took out some clean knickers and pulled them on. A clean dress from the wardrobe followed. I had no option other than to dress in the clothes I had arrived. in.

She went to the kitchen and started to get some food together. I stood, watched and talked. She is a fantastic cook. She told me she spent a lot of time with her mother, when she was younger and learned a lot. Including how to make amazing food. I've got used to cooking for myself but I'm not a patch on her. After we had eaten, she invited me to stay the night. I agreed. We had a few drinks and learned about each other's lives. Mine, nothing to write home about. School, college to learn engineering and work at the company. Going with the flow, no dramas. Hers a bit more involved. School and university interspersed with bouts of depression, which meant it took longer to graduate than she had planned. Another job before coming to our company. She left because of the less than accepting attitude, to who she was. She gets on really well now. Plenty of friends, including Caroline, who has taken her under her wing.

That night we just lay in bed cuddled together, continuing our talk until we fell asleep. In the morning, I sat and drank a coffee with her, before driving home for some fresh clothes and to get ready for work.

On Monday lunchtime I was sat in the cafeteria, again on my own. A tray appeared on the table, sat opposite was Caroline.

"I'm impressed. I always had the impression that you were a total arsehole. I was wrong."

"Thanks. I think. What brought that on?"

"I thought you were leading Sarah on and she would end up getting hurt."

"I really like her. She probably told you. How did I end up with such a bad reputation?"

"Probably because you went out with a lot of sluts."

"A bit blunt but possibly true."

"It probably went down OK with your football mates. What are they going to think now?"

"No idea. It doesn't matter to me. I think they will be alright. There is a gay guy on the team. He doesn't get any hassle. I'll just have to see what happens. I'm not going to shy away from it."

As we ate our lunch, we discussed my embryonic relationship. I thought she was going to rip me off a strip. She actually wanted to help. As Sarah's best friend, she wanted to do all she could, to make sure she was happy. It became clear, that Sarah had shared a lot of detail with her. Caroline seemed quite impressed, considering what she had thought of me previously. Her parting words,

"Don't mess it up."

I had no intention of doing any such thing. I was seeing Sarah, outside work, about three times a week. She and Caroline came to watch me play football. We had some drinks in the bar afterwards. Nobody seemed bothered that I kissed Sarah. In fact, I don't think anyone had the impression that she was anything other than a woman and my new girlfriend. The one comment I did get was,

"A lot nicer than your usual."

I left with Caroline and Sarah. We got a taxi, dropping Caroline at home, we ended up at Sarah's. I was a bit more prepared this time. Along with my football kit and wash bag, a spare set of clothes. We had planned for me to stay over. With Caroline's words ringing in my ears, I was determined to give Sarah everything she wanted. I wanted to make her happy. No rush. We had Saturday night and all day Sunday to explore each other.

No hesitancy, no doubts or strange thoughts. Sarah is my girlfriend. Biological issues aside, this was no different to any other relationship. A mutual interest, in enjoying each others company and making our partner happy. We Kissed and caressed each other for ages. A surprise, stroking down Sarah's side, she is quite ticklish. A sweet little squirm and giggle as I did. Being so much larger than her, it wasn't difficult for me to maneuver her on to her back. I began kissing down her body. I love her nipples, so small and pale. I kissed, sucked and nibbled them. As I moved down her body, reaching her abdomen, she raised her legs. Did she think I was going to fuck her? I had other ideas.

I know what I like and I used that as a guide. I stroked the small wrinkled scrotum. Her cock twitched. I took the shaft in my left hand, lifting it slightly, I slid my lips down across her knob. A wince. My thought, sorry, I'd caught my teeth on the crest of the glans. Concentrating hard, not to do it again, I tried to give an impression of a blowjob. I hoped that she would like it. There was no way I could take as much as she did. I tried and gagged. I lifted my head slightly. I concentrated my efforts on her knob, lips and tongue. My hand still on her balls, I could feel them tightening. I wondered if she would push my head away. She didn't. Slipping a finger lower, I stroked her anus. The response was instant. A quite groan, a thrust with her hips and spunk flooded my mouth. I'd tasted her and wasn't bothered by it. I couldn't cope with how much there was. I pulled my head away and spluttered it out onto her belly. Her immediate response was one of concern.

"Oh, god. Are you OK?"

"Sorry. That was my first time. A lot to learn."

She held out her hands. I moved up on top of her. I guessed the cum was now on both of us. With my head on the pillow next to hers, her lips tickled my ear.

"That was great. Thank you."

I was actually a bit disappointed in how it ended. I'd wanted to swallow it, like she had. Although, she appeared happy with my inexpert effort. I moved on to my back, needing a change of position and not wanting to crush her. Her hand sought my cock. It was slippery. Some of my fluid and her cum. Her tiny hand with it's delicate fingers began to stroke my shaft and balls. Not smooth but I'd trimmed as best I could. The light touch felt incredible. I couldn't possibly replicate the feeling wanking myself. Then something new and unexpected. Her other hand pulled back my foreskin. A finger on my knob and the skin rolled back over it. I could feel myself leaking pre cum like mad. Her finger gently rolled back and forth under my foreskin. Too much to take.

"Uh. Uh. Uh."

Withdrawing her finger, another stroked my balls. I curled up in a ball. That was the best wank I've ever had. Both of us were now smeared with cum. She did what I had and lay on top of me, as soon as my body had unfurled. Tired from the earlier football, drinks and now this, I slept. I woke some time later as Sarah moved off me. Had she been asleep too? It was pitch black. I fell asleep again.

I woke in the morning, alone. I could hear the running water of the shower. She came back in, as before in two towels. I took my towel and wash things from my bag and went to get clean. I took my time. Nice to have fresh clothes to put on this time. Sarah was in the kitchen making coffee and getting out some cereal. After breakfast, we sat and talked.

"Did you feel you had to suck me off last night?

"No. I wanted to. You said that you do the top and bottom thing. I want to try too. I'm sure you've had better. Give me time."

We discussed all manner of things. Where to got on our next date. What we liked to read, watch on TV and at the cinema. Our favourite and least favourite foods. On the more physical side, whether I should shave as she did. She was alright with the short trim. In the afternoon, a drive to the country and a boat trip along the river. This actually felt like a proper relationship. More so than any I'd had before. All of which revolved around bars, clubs and sex. Virtually nothing beyond that. Dinner at a restaurant on the way back.

It had been a great day. In bed that night, I decided to go to the final step. After some lovely gentle foreplay, I got onto my hands and knees. Surprised, she asked,

"Really?"

I didn't move, giving her the invitation. I was right with her reaction previously. The lube was cold. She whispered some hints in my ear, as her fingers probed my rear. She pushed me forward. I guessed the reason. Being so much shorter than me, I needed to be lower. Taking her guidance onboard, I felt pressure against me and pushed out. Quite an odd sensation, doing it. Whoa, she was in me. Definitely a stretch beyond fingers. She didn't move, other than to reach round and take hold of my cock. She started to stroke my shaft, without moving within me. I'd expected pain. It didn't come. Just a bit of discomfort. I relaxed. The stroking of my cock was coating her hand with pre cum. Lots of it. The shaft within me began to fuck me, slowly and gently. I could see why Sarah liked this. From what I was experiencing, more men should try this. The sensation was exquisite. I had to say,

"Easy."

I wanted her to enjoy this and I was getting close. The pressure on my cock reduced. She was using longer strokes within me. A couple of times, I felt the knob slip out and immediately back in. All the way in, I felt her body against mine. Her hand now harder and faster on my cock. Holy fuck, I thought I was going to pass out. I shouted, god knows what. Cum shot out of my dick in what felt like a dozen spurts. She kept rubbing my knob. A mixture of pain and pleasure. I felt the throbs as cum entered my arse. I felt her collapse against my back. I was struggling to stay in this position and I too flopped forward. I lay face down on the bed with her light frame on top of me. No words exchanged.

I thought that I was giving up my arse, for Sarah to enjoy herself. I hadn't anticipated the intensity of my own orgasm. It was almost mind blowing. I'd taken what I considered to be a gamble, even being with Sarah. In my view, it was paying off, in ways I would never have considered. I felt an emptiness as a limp cock slipped out of my anus. She asked,

"OK?"

"I've made a mess of your duvet cover."

"I don't suppose it will be the last time. I hope not."

We slept. Sarah set an alarm, for us to get up early and shower. She dressed for work. I put on the clothes from yesterday and drove the pair of us to my place. A quick change and I got us both to work on time.

My lunch hour never really seemed to match up with Sarah's. Mostly I ate alone. My only shared lunchtime was Wednesday when yet again Caroline sat down with me.

"Still all good?" She asked.

"Great actually and getting better."

"Amazing, isn't she." Said with a wink.

I sat and contemplated what she had said and the facial expression she had accompanied it with.

"You haven't?"

"Friends help each other out, when times are tough. Before you get any ideas, the three of us isn't happening."

Having dropped that bombshell, she returned her tray and went back to work. Life and work got in the way and I didn't have chance to meet up with Sarah until after football on Saturday. I showered after the game and left the club as soon as I was ready. A quick drive home to drop the car off and a taxi in to town to meet up. She had wanted to visit a club with burlesque dancers. All new to me but why not. We met just outside, I had arrived about ten minutes before her.

It was quite plush inside, dim lighting, comfortable chairs and small tables, around a small dance area and stage. Smart waitresses, in what I guessed was an approximation of Victorian dress. We ordered drinks and between the acts we talked. I was keen to find out if what Caroline had told me was true.

"I was in a really dark place. Caroline came to stay and look after me, for a week. I needed a hug and a shoulder to cry on. After a few days, it just happened. She is the only woman, I've been with. Like you, not what I was expecting but at the time, we both needed something."

An interesting evening beyond that. Several dancers, scantily clad, in exotic costumes, performing with ostrich feather fans, or with whirling tassels on their breasts. We had plenty of drinks and it was really late when we left. Not much before 2am when the taxi dropped us at my place. Undressed, straight to bed and sleep. We had reached a point, where we didn't feel the need to have sex, all of the time. Just physical contact was enough, for us to feel at ease. I think I had drunk more than Sarah the night before. I slept longer. Judging by the state of my throat, I had been snoring. Not too loud, I hoped.

I was woken by my cock being rubbed, in a rather suggestive way. The duvet was peeled back off me. I'd bought some lubricant, in the early days of our relationship. That was not what Sarah had in her hand. I suppose she had some in her handbag. What did she have in mind? I was still only half awake. I didn't have long to wait. My cock slavered with lube, hard and held upright. She mounted me, feet either side of my body, she lowered herself on to my cock. She started to ride me hard. Those cute little buttocks slamming down on to me. Even my anally fixated girlfriend had never down this. As she rose and fell, her cock bobbed and swayed. An interesting view. She rode me hard. Minutes passed. I was gritting my teeth. No good.

"Haaaaaar."

As the last of my cum entered her rear, she spurted. The bobbing motion flinging cum in several directions. Some on me, some on the bed, a bit back on to her stomach. A handsfree orgasm. Incredible. She collapsed on to my chest. I could feel the cock, still hard, pressing in to my stomach.

"Have you ever cum like that before?" I asked.

"Just once, with a dildo. That was much better. Sorry if I took advantage."

"I'm glad you did."

We both let out a low sound as my cock slipped out of her. We went to shower together. Nothing new for me, showering like this. Well not quite. I don't think wanking each other would go down too well, in the showers after a game. Sarah almost collapsed as she came. I held her. Looking down we needed another wash.

No need to dress properly. A quiet Sunday. I pulled on some shorts and a polo shirt. Sarah a cotton robe. I made the coffee. Sat on the sofa, Sarah came and settled across my lap. An arm around my shoulder. I tried to recall, if I had ever had a relationship which lasted this long. I was struggling.

"What would you think, if I told my parents about us? What would yours say?" I asked.

"That's alright with me. I think mine would be pleased. They normally only see me when I'm down. It's them or Caroline who pick up the pieces."

After we drank our coffee, I phoned my mum. A much easier conversation, than it would be with my dad. I don't get to see them often, because of the distance to travel. She went silent for a while, when I explained everything.

"I know it is a lot to take in. You might not understand. I was like that to start with. Please say something."

"Sorry. You took me by surprise. I don't really understand but that doesn't matter, as long as you are happy."

What my dad would make of it, I had no idea. He would probably understand even less than mum. Time to set those thoughts aside. There wasn't anything I could do about them. I just had to concentrate on things I could control.

On Monday morning, I drove the two of us to work. People were getting used to seeing us together. A few people whispered behind our backs but most were fine with it. Those close to us were really supportive. This was particularly evident, when the football season ended. At the end of each season, there is a presentation evening and celebration dinner, at the social club. I invited Sarah and Caroline to accompany me. At least we were sat at a table, away from Caroline' ex. All of the other players were great. No hint of any awkwardness. The three of us really enjoyed the evening. Although, we probably drank too much. It was late when we left. The taxi dropped the three of us at Sarah's. Caroline went to the spare room. The two of us undressed and flopped in to bed.

I'd not seen Sarah for a few days. She was in need of some activity. I was woken by her burrowing beneath the duvet. The first touch of that penis against my hole, is always filled with thoughts of what is to come. Stroking my cock as she entered, the feeling was incredible. The touch of her fingers, so gentle. Just like a piece of silk being dragged across my skin. I was enjoying being a bottom, far more than I'd thought. She seemed to get so much enjoyment from it. Her thrusting was getting harder and deeper. The expression on her face priceless, as she got close. Her fingers now in harder contact with my exposed knob, would mean I joined her. The trembling of her body and a quiet

"Uuuuh."

As she came. I arched my back, cum erupted from me. All the way up my chest. She continued to rub the tip of my knob. My body was shaking violently.

"AHHHHHHH!"

She didn't let up. Eventually, I could take no more and grabbed her hand. A noise by the door. I turned my head to see Caroline, stood in the doorway, not a stitch on. She scurried away in the direction of the bathroom.

"Oops." Was all Sarah said.

We heard the toilet flush. A minute later Caroline reappeared, she said sorry and pulled the door closed. We extracted ourselves from the compromising position and went to clean up. I'd started to leave some things at Sarah's place. Both wrapped in robes, we went downstairs. Caroline was dressed and getting ready to leave. Sarah stopped her.

"Come on. Sit down."

She put her arm round Caroline's shoulder. I went to make some tea. When I got back, Caroline seemed to have calmed down. The two of them were just sat, side by side on the couch. I put the drinks on the coffee table and sat in the armchair. Sarah kicked off with an apology.

"I'm really sorry. I needed a wee in the middle of the night. I forgot to close the door, when I went back to bed. Not what you were expecting or wanted to see. Are you alright?"

"I'm fine. I feel bad for intruding. I should just have gone to the loo. I couldn't help it. I got sucked in, to how much you were enjoying it. Both of you. I've never seen any man cum like that. It was incredible."

"It's because you don't fuck them in the arse." I said.

She burst out laughing.

"You just witnessed the best orgasm I've ever had. It would have been better still, if I'd seen you before I came. You look amazing." I added gallantly.

"Embarrassing. I should have put something on."

"I'm glad you didn't."

"We're still not doing it. You had a good look. That's as far as it goes."

I can't say that I would turn down a threesome. She really did look amazing. Her short cut hair accentuates her pretty features. Her body is great. Small perky tits with small pointy nipples. Flat stomach, nice small waist, landing strip pubic hair and from what I saw as she turned away, an awesome arse. If I had seen her like that, a while back, I would have become obsessed with her. Now, I liked what I saw but I would respect her wishes. I had started to see her as a friend. She really was doing her best to help myself and Sarah.

With the atmosphere cleared, at least to an extent, Caroline stayed with us for the rest of the day. By the end of the afternoon, we were all laughing about what had happened. Caroline left to go home, just before dinner time. We ate and settled down to watch TV for the evening. Sarah asked,

"Would you have sex with Caroline?"

"Who wouldn't want to. She looks incredible but I'm with you. I made that choice. Besides, I think she is still a bit uncertain about me. I can't deny it, her body is great but I see her more as a friend. It wouldn't feel right."

I think she liked the answer. Perhaps, me having seen Caroline naked, Sarah feared losing me to her. That wasn't going to happen.

After what had gone on this morning, neither of us felt the need for anything in bed that night. I drove her to work in the morning. With the amount of time we were spending together, we both had clothes in each others places. We started to talk about the practicalities of being together, in the long term. Having one flat or house would save us money and make things easier all round. We were both renting. Together, we could afford to buy. For now, I gave up my flat and moved in with Sarah. Fewer stairs to climb and a bit of outdoor space. If things went well, we would buy somewhere together.

Time to meet the parents. Hers were overjoyed, at how settled and happy she had become. Mine flat out refused to believe that Sarah wasn't female. They thought I was joking. Their issue, ours. Sarah certainly wasn't going to provide them with proof.

I still wasn't meeting Sarah very often for lunch. Most days this was time for myself and Caroline, to trade mock insults or have some serious conversations about relationships. With myself and Sarah now settled, she was happy to expand the conversation beyond that. She hadn't been in a relationship, since the one with my team mate. I think she was done with footballers. I may be able to help her out but I didn't bring it up at the time.

"It's just been my and my rabbit, for a while now. It'll be worn out soon."

"You'll be fine, something good will turn up. You never know where, when or who. Look at me."

"I suppose so. Who'd have though of you as a sissy boy, sucking cock and getting it in the arse."

"I'm not sure I'd have put it quite like that but you get the point."

"Just think. The only person either of us have taken it in the arse from, is Sarah."

"I'm trying to eat my lunch."

"Good job it isn't sausages."

Not the ideal topic of to talk about over lunch. A bit more information in the locker. Caroline didn't do anal, before her time with Sarah. Back to trying to help her. None of my workmates would suit her. Too rough and ready. One college friend might. Luke was on a couple of the courses I took. He was the only person from that time, I kept in touch with. He doesn't live far away. I'd met up with him frequently, until I got together with Sarah. Less so now. While I'm hands on and practical, he is intellectual and theoretical. I fix things, he designs them. I sent him a message, with a photo of Caroline from the presentation evening. He was really interested. Over the next couple of days. I tried to coordinate a blind date. Arrangements made for Saturday evening, I wasn't even sure Caroline would turn up.

That was out of my control. What was within my control on that particular Saturday, was pleasing Sarah. Her knowledge of the mechanics of our relationship, was so much better than mine. For the most part, I think that I was getting the best out of the sex. I don't think that she was worried in the slightest. I still felt like I should be doing more. I was trying. If anyone had said, months before, that I would be swallowing someone else's cum, I'd probably have felt sick. Now it felt perfectly normal. Today and after a fair bit of trial and error, I managed to give my first deepthroat blowjob. No coughing no gagging, as cum shot into my throat.

What followed, may have felt like torture. I eased my cock into her arse. My movements were minute, fractions of an inch. All the while, I was brushing her cock, slowly, softly, no rush what so ever. Almost half an hour of this and Sarah was virtually screaming at me to fuck her. Not a chance. I kept up the torment, maybe another fifteen minutes. Eventually, I relented and increased the depth of my stroke but kept to the slow tempo. I wrapped my hand and let her fuck my fist. If I had thought my orgasm was intense, when Caroline had seen us, this was on another level. She came with a whimper and then went totally limp, eyes rolled back in her head. The only sign of life, the slight rise and fall of her chest. Hardly concerned about myself, I think I came just before she did. I pulled out my cock, got beside her and took her in my arms. Everything I said, went unanswered. I was worried.

It seemed like an eternity before she said anything. When she did, it was just one word,

"Bastard."

"Oh, god. I'm so, so sorry. Are you alright?"

"Will you marry me?"

"Huh. Is that even possible?"

"I don't know and I don't care."

She wriggled round in my arms and kissed me. She fell asleep right there, her lips fell away from mine, soft gentle breaths leaving her mouth. She may have slept but I had a lot keeping me awake. I'd never considered getting married before. I was now wondering if it was possible to marry a biological male who lived as a woman. No wonder my head was spinning. It may have been a couple of hours before I dropped off. Even then, it wasn't good sleep.

I woke as Sarah nuzzled up close to me and started playing with my dick. I was erect and coating her hand with pre cum, when the doorbell rang.

"Fuck."

I got up grabbed a robe and went to the door. Stood there, smiling, was Caroline.

"Pleased to see me? Not sure that suits you."

In my rush, I'd grabbed Sarah's cotton robe, rather than mine. Shorter and flowery, rather than my longer one with geometric patterns. What's more, I still had a hard on and there was a small wet patch on the blue fabric. She didn't wait for a reply, brushing past me and sitting down in the lounge.

"Sorry for barging in. Were you fucking?"

"Not quite."

Sarah came in with my robe on, it was dragging on the floor. Caroline put her hand over her mouth, to stifle a laugh.

"I interrupted your fun."

"It's OK, we can start again, later." Sarah said.

"Can I watch him cum?"

"Behave. It's too early for jokes."

"I wasn't joking. Anyway. I just had to come. Jude, you are amazing. Thank you so much. Luke is incredible. So handsome, intelligent and gentlemanly. I may have come across as desperate. I invited him home. He walked me to the door kissed me, said goodnight and said he'd call."

She got up, placed a hand on each of my cheeks and kissed my lips. The first real physical contact we had ever had. I'm not the sort of person who hugs everyone. I don't think she was either. Sarah interjected,

"Put him down. He's mine. We're getting married."

She'd had asked. I wasn't sure she was serious, or whether it was just a heat of the moment comment. I'd just come back with a question. She seemed to have taken it as being a done deal. In fact, I'm pretty certain neither of us were against the idea, if it was legal and possible.

"Yes! The bridesmaid gets off with the best man. Luke?" Caroline asked.

"Getting ahead of yourself there." I replied.

Sarah went to make coffee for the three of us. All thoughts of what she had started upstairs, now gone. Along with my erection. We sat and talked. It became clear that Caroline hadn't been joking. Frustrated by months without sex, she wanted something. She had hoped, probably, that Luke might have been less of a gentleman. The build up from her night out, needed somewhere to go. I looked at Sarah, I was really uncertain, even though Caroline had seen us before. That was accidental. Caroline was looking for something different. Last time she had gone to hide. What did she want now? Sarah's first thought was for her best friend.

She took Caroline's hand and went towards the bedroom. What could I do but follow. Sarah hung my overly long robe on the back of the door. Naked, while Caroline remained in her outdoor clothes. How many times had they been together like this? Neither seemed bothered by the situation. Caroline began to remove her things. Was she going to join in, despite what she had told me? I got my first proper view of her bum. It was every bit as good as I had thought. I suppose it was my turn. With the wet patch I'd added to Sarah's robe, I dropped it into the laundry bin. Caroline mounted the bed, kneeling on one side. I got a brief flash of her pussy from behind. Sarah gestured for me to get on the bed and lay down.

Was she intending a repeat of what of what Caroline saw, even a reversal of last night. Caroline was kneeling next to me, legs slightly apart. The sight from my angle looked enticing. Enough to get my cock stirring. Sarah, noticing my gaze,

"Hey. I'm over here."

Caroline sniggered. Sarah's lips began to kiss their way from my balls up my shaft. What had started stirring was now fully at attention. Sarah pulled back my foreskin and rubbed dry finger against my knob.

"Pffffff."

Punishment for looking at Caroline? This was quickly relieved, by her wet mouth sliding over it. My assumption had been right, whether this was retaliation, or she wanted me to experience what she had last night, I don't know. Even the application of lube was slow, deliberate and sensual. Caroline had shuffled so close to Sarah, her breath must have been brushing Sarah's cheek. If anything, the insertion into my anus was even slower than the one I'd made. The tracing on her fingers along my dick, almost too light to feel.

Quick glances at Caroline were telling. Her expression one of pure animal lust. Her left arm round her back, hand between her legs, fingers in her pussy. Her right slid down her stomach and a couple of fingers were slowly and delicately stroking her clit. I'd seen some of my conquests, I could hardly call them girlfriends, wanking. They had all gone at it harder than this. My attention was called back to Sarah, with her focus now on my foreskin. An initial brush was followed by, the slowest retraction you could imagine. Eventually, the roll of skin settled behind the crest of my knob. The close up view of this obviously did something for Caroline.

"Uh. Uh. Uh. UH."

I could hear the slopping noises, as her fingers delved in to her pussy. She leant over and kissed Sarah's cheek. Would she leave us to it? Not a bit of it. Her movement did at least mean Sarah's cock went a little deeper in to me.

Fluid was pooling on my belly as my cock leaked. In the frequent periods between the women I'd been with, I had edged myself while wanking. That was nothing, compared to what was happening to me now. Occasionally, she would thrust deep within me. I think this was for Caroline's benefit. My grunts, seemed to help her along. With one of these, she came again. I got the impression she could cum frequently but was holding off as much as she could.

Every time I began to shift and wriggle, Sarah held my hips still. The idea obvious, don't move. How long had we been going? I had no idea. I'd been so close, a couple of times, it was agony. All I could do was watch the two of them. All of a sudden, Sarah said,

"Now."

I think she was struggling as much as I was. She began fucking my arse, hard. Her hand stroking my exposed and very slippery knob. I could see why Sarah had reacted the way she did. She came in my arse. As she did, the only way I can explain what happened, was a whole body orgasm. My bum cheeks tightened, my hips bucked and rose, my legs shook. I'm not sure I can recall much else, other than a massive amount of cum shooting everywhere. For the first time I can recall, it reached my face. All I could do was gasp. To my right, Caroline had an orgasm approaching, the intensity of mine.

"AH. AH. AH. AHHHHHHH!"

She fell to her side, her right hand gripped between her thighs. Her hard nipples brushed my arm. I don't think any of us moved for a while. Sarah was the first. She pulled her cock out. I twitched. Caroline, raised herself up on her elbow and kissed my lips. She must have tasted my cum.

"You lovely man. Thank you. Not just for this but for being there for Sarah and for Luke."

She got off the bed and began to get dressed. She used her knickers to wipe the fluid from her thighs and pussy. Ready to leave, she kissed Sarah and departed. When she had gone, Sarah said,

"Great isn't it. Thanks for helping her out. That means a lot to me. She has done so much for me, it's nice to be able to give something back."

I didn't say anything. I was still trying to take things in. I'd just had an amazing orgasm. I'd watched Caroline, who didn't want to get involved, cum several times. She'd brushed her tits against me and kissed my cum covered mouth. All of this and it wasn't even Sunday lunchtime.

My Monday lunchtime with Caroline was a relaxed affair, no name calling or rude banter. I think she was genuinely happy and grateful for yesterday morning.

"That was amazing. Don't expect too many repeat performances. Do all guys cum like that, with it in their arse?"

"How the hell would I know."

"I wonder if Luke does?"

"Ask him. I've no idea what he does in bed. I only know him as a really good friend."

"We're out next Saturday."

"No need for an early morning call on Sunday. You can tell me everything on Monday."

Picking up on her comments, 'too many repeat performances' did that mean there would be some? I got the report of her date, on Monday. She had taken Luke back to her place. He was going to sleep on the couch but that wasn't going to cut it for her. I didn't want to know the intimate details. She loved what they did. In her view, I'd gone from potential villain, to really good friend.

All of this, I could never have contemplated, a while back. I was in a great and settled relationship, with a beautiful trans woman. I'd made a good friend of a woman, who probably wouldn't have given me the time of day. Plus I'd set her off, on what everyone hoped, would turn out to be a long term relationship.