What Might Have Been

What Might Have Been

Does John really understand?

This story was written after several role plays with Prodiver, where we explored various less frequently visited aspects of cuckolding and submission. I thank him for his help in formulating this rather disappointing story...

The Ad

Wanted - loyal, loving life partner

I am 33, vivacious, curvy and very loving. I am looking for a man who can give me love and loyalty. You should be dependable, intelligent and very understanding.

This is going to be my first long term relationship and I want it to last, but it will not be conventional.

Sex and love will be central to our relationship; we will both get a lot of sexual satisfaction from being together, but you will NEVER have sexual intercourse with me.

If you are intrigued, get in touch...

It was ten years ago that I placed this ad on Craigslist. As you can imagine I had hundreds of replies and sifting through them was not easy. In the end, I listed my top 10 and started my search by replying to what, on paper, looked like the most promising response I had received.

His name was George. He was 40. After exchanging a dozen emails it turned out he was 63, married and wanted a dominatrix to spank him.

I reset my expectations and worked through the list until I got to John. John had not written as much as some in his response to my ad, but there was a sense that he knew what I was looking for. After just 3 emails we had agreed to meet at a local Starbucks and I was feeling positive. When I arrived, John was already seated in a comfy armchair by a low table with an empty two seater sofa diagonally across from it. He stood up and guided me to the sofa. Asking what I would like to drink. He went to the counter and bought my drink. When he got back to the table, he carefully handed me my cappuccino and sat down in his armchair.

John was 47 years old - a school teacher. He had a self contained confidence, but very little bravado. He had never married and had no kids. During that first date, he didn't seem like he was trying to impress me. He was just getting to know me and sharing his story. He was an only child and had already inherited a lovely house from his parents. He lived a comfortable life and had reassuring savings.

"So please tell me Rebecca, what did you mean when you referred to sexual intercourse?"

I was taken aback by such a direct inquiry and had not really planned how I would answer such a blunt question.

I fumbled a little. "Um, well..." I smiled at him. "It's complicated, but I guess I will have to just tell you what I am expecting from our relationship." I hesitated at this point - realising I didn't know enough about John to predict what his expectations might be. "Maybe we need more time before we get down to details. Please allow me to ask you some questions first. You said you have never married, but have you ever lived with a girlfriend?"

It was his turn to hesitate. "Well, um, not exactly, but I did have a two year relationship that was going that way. Unfortunately she dumped me before we moved in together when she discovered my fetish for wearing ladies lingerie. Just about all my relationships have ended when this has come out, so now I always mention it early on to get that out of the way. I have tried many times to stop dressing up, but I always go back to it, even after years of suppressing it. I am actually wearing stockings, a suspender belt, panties and a bra under my suit today" he blushed.

I smiled, suppressing a giggle, "Let me see!"

He bent down and lifted his trouser leg exposing black sheer nylon stockings above his socks.

"Ah," I replied, "so you are no stranger to the kinky side of life?"

He went on to tell me how he loves nothing more than driving to a different area from where he lives to shop for lingerie which he always wears under his men's clothing and, wears exclusively when home alone in his secluded house. Holidays are his most daring times - often leading to his most exciting encounters with women, but never to anything long lasting.

"Well, John" I said, "the good news is, you have found a woman who is not put off by your kink. You were right to let me know from the beginning. I value honesty and openness above all else. Allow me to respond in kind. I hadn't planned to just blurt this out so soon, but I feel you may be able to handle it... I want you to be my cuckold hubby. I will regularly fuck my boyfriends, but I will always come home to you. It may take you some time to... no, let's not get into details too quickly. Tell me how you feel about me. My looks, my personality..."

"Well Rebecca, obviously you are beautiful and I am very attracted to you. It is also obvious that you are way out of my league. If we marry, nobody will believe you could be my wife. As soon as I saw you, your ad made sense to me. I will just want to worship you from a distance. Bask in your glory. Feel fortunate just to know you. I already feel compelled to obey and serve you. I can't even imagine making any demands on you."

I smiled. "Oh my, John! We are on the same wavelength. Come and sit next to me on the sofa."

John stood up and first moved his coffee to the other side of the table, then carefully sat next to me, leaving a respectable gap between our knees. I immediately reached over, putting an arm around him and pulled him closer. He leant in tentatively, but I pulled on him. "That's it John, shuffle in closer. You don't need to be afraid. I love the sound of being worshipped, but you don't have to put me on a pedestal. We can be close and loving. I know you will have urges and needs of your own and I will help you with all that. Allow me again to make some assumptions. Tell me if I am warm... You are a sensitive lover, always lots of foreplay, especially oral given by you. You can spend ages licking and gently sucking and sometimes your lover has multiple orgasms before the fucking even starts. It all gets you so aroused, that when you finally get inside her, you cum after only a few strokes. Other times, when you are working away down there, you go soft and can't do anything about it. You eventually have to apologise and she reassures you that it doesn't matter. But it really does and you both know it."

John blushes. "Oh my god, that's amazing. How could you know so much about me?"

"Believe me John, you are not that unusual, but you are lucky to have found someone who understands you at last. We can dispense with all that anxiety. You are not built to fuck a woman, but you do still have urges. You do get hard sometimes, but not always when you want to. You never need to be embarrassed with me. I will always understand. Like now you are so aroused. Let's go to the bathroom and I will take care of that for you."

I get up and offer John my hand. I lead him to the back of the cafe and we enter the disabled cubicle. "Now, don't worry about a thing." I say as I kneel down, unbuckle his belt and unbutton his suit trousers. "Lovely! Ivory lace!" I whisper as I see his panties and suspenders. I ease the panties down and his little throbbing 4 inch willy springs free. "Awwww. Beautiful." I whisper as I kiss the tip. I feel him start to quiver as I take his lovely little swollen head between my lips. My right hand gently cups his balls as, inside my mouth, my tongue is circling his cock and he starts to spurt. I keep my lips tightly around his narrow shaft as his pulses slow. I pull slowly back off his willy, closing my lips as the tip of his head squeezes out. Then I stand up and hold John's head in both my hands. I move in slowly to kiss him and his lips part. I gently allow all his sperm to flow into his own mouth. "There you are sweetie. Swallow it all down like a good boy. Now tidy yourself up and I'll see you back at the table." With that, I leave the cubicle and go back to our little sofa.

A moment later John joins me on the sofa and already seems more relaxed. "You see..." I say softly to him, "I am a slut. I suck a stranger off within 5 minutes of meeting him. Just think of what I will get up to in a nightclub with horny studs all around, or when you take me on holiday to a Caribbean paradise. What's more I will revel in telling you every detail of how I have been fucked and I will save all the mess they leave inside me for you to lap up and swallow, just like you did just now. I really hope you like the taste of other men's cum..." I pause for a moment, shocked at how much I have shared after so little time. "We seem to have clicked, John. Tell me how you feel. Are we going straight back to your place now?"

John turns and looks me straight in the eyes. He is smiling, but still nervous looking. "I can't believe what is happening, what has already happened. I feel as if we belong together. I think I understand what you feel about the difference between the men you fuck and me. They, real manly men, can do whatever they want with you. Your body and soul is theirs to use and abuse however they see fit. At the same time, I can love you and you can love me but it's different. My little willy is not a weapon. It does not invade. It pleads. It needs loving care and encouragement and you are happy to indulge it - indulge me, as long as we accept our place and our role."

I smile, delighted and surprised that he's already adopted my word for his cute little penis. "Oh John! You really do get it! It's incredible. I could never have said it like that, but you are absolutely right. Your willy pleads for help, and I will always indulge it, and you, but my lovers' cocks are weapons that invade me and use me. I submit to them and welcome their power. They will use and abuse me and I will come home to you for love and happiness. With you, for the first time in my life, I will have security and contentment as well as excitement and adventure. I used to feel so lonely when I got home after one of my many adventures, lonely, empty and forgotten."

John agrees; "I have been lonely too, Rebecca. All alone in that big rambling house, after another girlfriend has dumped me, or coming home alone after a fun holiday or even just shopping. Let's go home together now and start our new life - together!"

I followed John in my car as he drove slowly out of town and then to the edge of his village where his impressive Georgian house stood at the end of a curved gravel drive behind high fir hedges. He got out of his car and came straight over to mine and opened my door for me. "Welcome home Rebecca. Please come with me." He took me by the hand and led me to the big red front door, which he opened and guided me through. As soon as he came in after me, he took off his jacket. I could then see the outline of his ivory white bra under his shirt and he said softly to me, "Is it ok if I show you my lingerie now Rebecca?"

"Of course John. You are with a kindred spirit. Do as you please."

I watched him as he took off his tie, then his shirt. The bra looked faintly ridiculous on his slightly hairy chest, but I was surprised at how his manboobs actually nicely filled what looked like B cups. "John." I stated, "We will have to sort out that hairy chest of yours."

John blushed, but carried on undressing until he was just in the lovely lingerie. His little willy was already straining at the lacy panties. He was just standing there so proud,

I had to take a pic. I got my phone from my handbag and took a quick snap. "Lovely John. Would you like to show me how you jerk off?"

Again John blushed, but I just smiled. "Don't be shy. Show me."

"What here?" he asked.

"Where ever you like John. I just want you to be comfortable. Would you prefer to be lying down to jerk off? Is that it? Shall we go up to the bedroom? Whatever is best for you John."

John looks bemused. I can tell he wants to ask me to suck him again, but inside he isn't sure if he should ask. I enjoy his discomfort. He is right to hesitate. He shouldn't expect that for every little erection.

After a long pause, John stutters, "Y-yes Rebecca, upstairs. On the bed. Sorry!" and he scurried off up stairs, I follow behind and see him get straight onto his big

King size bed and pull his panties down.

"Good boy John. Let me see you jerk that lovely little willy. Let's see how much more you can cum and how far it spurts up your tummy. Do you think it will reach your sexy bra?"

"I don't know Rebecca. I'll try."

"Awwww, so sweet John. Do your best..."

John is jerking his hard little willy so fast, it is quite comical, so out comes my phone again and I start videoing him jerking off. I giggle as he starts to cum again. Three quite strong spurts send ropes of cum up to beyond his belly button, but well short of his ivory lace bra.

I sit on the bed next to him and using thumb and finger of my right hand, pick up a stringy glob of his cum. I bring it up to his mouth and he opens wide. "That's it John, suck it off my fingers." I then take another glob and eat it myself. "Mmmmm, lovely! You do taste good. Now you scoop up the rest and eat it up like a good boy." I then watch as he eats it up and am pleased to see him relishing it without any hesitation or complaint. I then bend forward and gently lift his little soft willy up to my lips and kiss the last trace of cum from his hole, licking my lips as I put his penis back neatly in the lacy panties. "There, John. Does that feel better?"

"Yes, thank you Rebecca. Much better!"

I smile to myself. Content that he now knows who is in charge. It is not an uncaring strictness, but it is a recognition that he should never expect service from me. Everything is on my terms.

The rest of the day was very pleasant. We talked about everything. John cooked two delicious meals which we both enjoyed eating with French wine and Belgian beer, we never stopped smiling the whole time we were together. Between the meals, John showed me round the house and garden, staying in his sexy lingerie the whole time. We listened to music and watched a bit of TV.

Even though John had had two beautiful orgasms and we had both eaten his cum, he never touched me sexually or saw me naked. This made me so happy and optimistic for the future. He was behaving so perfectly it got me believing that I may be able to control him even more than I had originally thought. Part of me felt a little guilty and that I was going to try to withhold full intimacy from him for as long as I could, but my kinky adventurous side felt that it is always worth trying, as long as I am prepared to give enough when he really needs it.

As I was thanking John for such a beautiful day, he surprised me even more by asking if I would like to move some of my stuff in to make it easier if I wanted to spend the night. It was the sweetest way I had ever heard of edging towards living together and it was at the end of our first date. I managed to keep my composure and gave him a big kiss and a big smile saying, "That is a wonderful idea John. I know a man with a van. I will let you know when he can fit us in. This is so exciting - you don't waste any time when you make up your mind, do you John?"

John held me after the kiss. "I don't want to waste any time getting to know you better Rebecca. I think I am already falling in love with you. I have never felt like this on the first day I met someone. I feel so close to you. Like we understand each other."

"Me too John." I whisper into his left ear. You are definitely one of a kind - and a perfect match for me."

John and I chatted the next day and I told him that I had arranged for a man with a van to help me bring some stuff over to his place and that he could fit us in early evening on the very next day. John offered to pay, but I told him there was no need. Everything was already taken care of. What John didn't know was that Leon, my man with a van, had done a few jobs for me before and no money had ever changed hands. He actually came over at lunch time and I made him a hearty lunch. When we had both finished our jacket potatoes, I showed Leon all the things I wanted taken to John's place and finished packing my cases. Loading the van took no time at all and once that was all done, that is when the fun started...

I did a quick check around the house to make sure I hadn't forgotten anything and told Leon to go upstairs and make himself comfortable. He knew where my bedroom was and bounded up the stairs two at a time. I followed a couple of minutes later and found him lying naked on my bed, one knee bent and his enormous cock lying across his other leg as he beckoned me over to him. I unbuttoned my dress and let it slip down off my shoulders revealing my specially chosen lingerie for this momentous day. It was all pure silk, powder blue and shimmering. I had a balcony bra that really lifted and displayed my boobs. The panties were high thigh, but not too brief. The ensemble was finished with matching suspender belt holding up sheer tan stockings. When I stepped close to the bed, Leon let out a low whistle and grabbed me around the waist. Flipped me onto the bed and crouched over me, looking down at my expectant face framed by my long blond hair strewn around my head on my burgundy bed cover.

SLAP!

My left cheek stings. I look up at him, stunned. He crawls back, tugging my silk panties off as he looks down at me. Suddenly, he straddles my tummy. He yanks my beautiful silk bra up and lies his growing pulsating cock between my breasts. He spits down onto his cock and over my breasts a few times, pushes each breast up with his hands and slowly starts to fuck my breasts. "Spit Beccy, spit." He urges me. Get them lubed up. I add my spit to my breasts as he fucks them faster. I feel his hardness increasing and his cock getting longer. Next he moves his knees higher and his cock is on my face. I reach up to hold it and guide towards my lips. I kiss his monster cock and take the massive swollen head between my lips. My mouth stretched as wide as it can go. He thrusts forwards, I lift my head to help him side into my eager mouth. Leon then clambers even further up and lowers his cock into my waiting up turned mouth. It slides into my willing throat and gurgling noises emanate from my mouth. I relax and accept his invading member into my throat and try to overcome the desire to pull away. He keeps thrusting forwards filling my throat with his throbbing shaft until he is balls deep in my face.

My face mouth and throat are now united as a sexual organ. Welcoming his massive cock. Unable to breathe, I surrender to his invasion, feeling a tingling in my toes and fingers as he rhythmically pounds my face with his huge manhood, I feel a darkness encroaching on my vision with sparkly stars all around. Suddenly he pulls out and rolls off me. I drink in oxygen as I gulp the air into my lungs. Panting so fast at first and then gradually coming back to normal.

Before I know it, Leon has my feet up by my ears, I am bent double and he is already inside my sopping pussy. Pounding my real sex with the same relentless rhythm, Leon again slaps my face. "Take it Beccy! Take it all! I hear and feel his heavy balls slapping on my ass as he ploughs into me. Stretching my pussy to the max, he pounds away. I feel my orgasm building, intensifying with each stroke. Every now and then he stops when he is all the way in. He grinds his hips against mine, squashing and mashing my clit against his rough pubic hairs. Pushing me further towards my inevitable orgasm. I start to shudder, my tummy clenches, my legs stiffen then shake. I totally lose control and quiver beneath him and around him, my pussy clenching and releasing involuntarily. Then Leon stiffens. He groans as he starts to pump his seed deep into my sex. Hot sperm gushing into my receptive pussy as he enjoys his climax with me breathless underneath his powerful body. Finally Leon collapses onto me, holding me in his strong arms. He rolls over and leaves me on my back, getting off the bed and putting his clothes back on. "You are a great lay Beccy. I never have to hold back with you. If you can drag yourself to the van we can get going now."

By the time I struggle off the bed, Leon is downstairs checking the van. I sit up and pull my bra back down and retrieve my panties. I put the powder blue silk panties on again, even as I feel Leon's sperm oozing out of my well used pussy. I grab my dress and put it back on, smoothing it down. I go into my bathroom to brush my hair back to a respectable state of order and look at my totally messed up make up. That is not a quick touch up. I think to myself. Maybe John can see the real me today. After all, we are going to be living together. I quickly wash my face in the sink and then rinse it in cold water. I pat myself dry with a towel and stare into my own eyes. John will see me like this soon enough and it makes me look so housewifey. I smile as I think of the present I have for him inside my panties. Leon calls from downstairs, "Hurry up Beccy. I have somewhere to be later. Leon looks up as I walk down the stairs. "Very librarian Beccy. Nobody would ever guess."

I playfully punch him in the arm as I slip past. "Well a certain someone isn't going to have guess tonight. He will know for sure!"

We arrive at John's house at 5.00pm. He comes out and welcomes me with a lovely kiss. And tells me I look beautiful. I thank him and say I like his shirt and the bra I can make out under it. He blushes, but thanks me too. "I'll take my main case up to the bedroom to unpack, you help Leon with the bigger things please John." In the bedroom, I see that John has set up a dressing table for me from one of the spare rooms and made space in the wardrobe and drawers. I busy myself unpacking and then lie exhausted on the bed.

Downstairs, John and Leon have brought everything in and Leon is ready to go. John thanks him for his help and offers his hand to shake. Leon shakes his hand warmly. "All the best my man. You have got yourself a handful there. Good luck and God bless." With that, he turns and gets into his van, driving off at speed smiling to himself.

John doesn't think much about it and goes back inside. As he closes the door, he hears, "Jo-hn! Can you come up here please. I need your assistance."

John climbs the stairs quickly and coming into the bedroom he sees me lying on my back on the bed. "Take those clothes off and come here John. I have something very special for you."

John strips down to his own lingerie. Pink today. Shiny satin with white bows and frilly edges.

"I need you to take my panties off, get between my legs and eat all the cum from my pussy."

I have no idea what was going through his head, but he just stood there motionless as I lifted my knees and raised my bottom to help him remove my panties. "Chop chop John. Get on with it!"

John suddenly stepped forwards and knelt at the end of the bed. He reached out with trembling hands and eased my panties off my hips and down my legs. Holding the panties he stared at the half dried cum on the gusset and then up at my swollen glistening wet pussy. First he licked the panties, then he placed them carefully next to me and leant in towards my used pussy. "I am at the gates of heaven Mistress Rebecca. Thank you so much for inviting me in."

I felt his warm breath on my pussy as he got closer, then I felt him tentatively lick my outer lips as his words swam around my head. Mistress Rebecca, mmmm, I wasn't expecting that. "That's it John. Lick it all up."

John probed with his tongue between my inner lips and I felt Leon's cum start to flow out. Slurping sounds filled the room as John lapped up the cum eagerly. His hands reached up to my hips and he pulled down on me to bury his face in my sopping cum filled pussy. He licked sucked and swallowed until no more cum seeped out. He then moved his mouth up towards my clit and very gently started licking around it.

A very different kind of orgasm was starting to build in my loins. It grew slowly as John worked expertly on my whole pussy and clit. As it gradually gained momentum, the warmth and intensity seemed to envelop my whole body. I was rotating my hips and grinding against John's face as I tensed up. All four of my limbs stiffened then my whole body writhed and shook uncontrollably. John immediately slowed his movements and eased the pressure he used on my clit and let me wind down from the incredible intensity I had just experienced. I had been spot on with my suggestion that he was an expert cunnilinguist and was now just wallowing in the subsiding sensations of the most wonderful clitoral orgasm I had ever had.

John now came up from between my sweaty thighs and lay next to me. He rested his head gently on my shoulder and cuddled me. I felt his little stiffy pressing against my thigh and reached over with my right hand to hold it gently. He reacted with a sharp intake of breath to my loving touch. He was throbbing so much and even harder than he had been yesterday. I could tell he was on a hair trigger, so I very slowly pulled his fore skin back. "Lie back and relax darling." I whispered. Everything is going to be alright. He got comfy and I sat up, so that I could give his little willy the attention it deserved. Two more deliberate strokes and he starts tensing up. I start stroking a little faster and feel him reach the point of no return. I relax my grip a tittle as he groans, but keep moving up and down. He starts to spurt. Much stronger than yesterday. Ropes of cum up hit tummy onto his bra, even up to his chin.

I slow my hand right down and lift his subsiding willy as I lower my head and I suck the sperm off the end of his softening shrinking member. "Yummy!" I smile as I swallow his sperm. I proceed to gather as much of his sperm as I can between the palms of my hands on his tummy and chest then bring them carefully up to John's mouth. "Open wide darling," I urge as I allow the gooey sperm to slip down into his eagerly open mouth. "Good boy! You are Mistress Rebecca's good boy aren't you?"

I lie back down and rest my head on his shoulder now. Holding him tenderly. I am still not sure how I am going to use this welcome development to my advantage, but things are definitely going to be interesting as our relationship deepens. Will Mistress Rebecca have a willing slave, or devoted submissive. We'll have to see where things go from here. What I know is that I have made John cum three times already and he has given me one mind blowing orgasm, but he has never seen me naked. Never touched my breasts. But he has hungrily eaten another man's cum from my well used pussy. A decidedly unusual situation with exciting possibilities, that's for sure.

We lay together for a long time. Our breathing naturally synchronised and we shared our warmth. We were together as one and I felt content and safe in John's house, in John's bedroom, in John's bed and in John's arms.

I was also getting hungry, so I roused John. "Is anything planned for dinner darling? Maybe you should go down and it started..."

"Oh yes Mistress Rebecca. It's all prepared down in the kitchen. It'll only take me a few minutes to finish it all up. You stay here and I'll get it all sorted."

John gave me a tender kiss and got out of bed. I enjoyed seeing him stop by the mirror to check his lingerie. He tucked his little willy into his satin panties and straightened his stockings, then headed down stairs. I decided to have a shower and change into my nighty. This meant that John was not around while I was undressing, showering and getting dressed again in my sleepwear. I really like the idea of delaying him getting too familiar and accustomed to my casual nudity and any sexual contact with my body. How long can I maintain this distance, this aloofness, even though he will be regularly eating other men's cum from my gaping pussy.

John has unwittingly given me this challenge and I am going to enjoy pushing things as far as I can without putting him off or making him feel neglected. But why would he feel neglected? I have sucked his little willy, given a hand job and watched him jerk off all in two days. I figure that, as long as I don't actually refuse a request or rebuff an advance, I can make believe that I am not withholding anything from him. It is just his own natural reticence that is preventing him from daring to take the initiative with me. Such a fun feeling playing and winning a game with someone who doesn't even know we are playing.

I put my dressing gown over my nighty and go downstairs barefoot to see a beautifully set dining table with dinner for two all prepared. "Oh John, you are a marvel. So clever to have this ready for us so quickly." We both savour the much needed food and wine. Three delicious courses and two different wines. The conversation never strained, we talk about the neighbourhood, local shopping, nearby walks, restaurants, cinemas, movies, music, everything.

The only worrying thing is the look on John's face when my phone chimes with a message and I spend a few seconds reading and answering it. After the third time, I put my phone down and look straight at John. "Is something wrong darling?"

"It's just the m-messages Rebecca. They interrupt our c-conversation somewhat!" He stutters.

"Well darling, I have to answer. It would be rude not to. Wouldn't

It? And they are about tomorrow night, so I can't delay too much can I? Well? Do you agree

John? Would it be rude to ignore a boyfriend trying to arrange a date?"

John just looks at me. Obviously surprised at my openness. I hand him my phone so that he can read all the messages. "These messages are of interest to both of us darling. Carl is only in town for a couple of days and really wants to see me."

Carl had invited me to his hotel for dinner and been very detailed in what he expected of me that night. I had answered playfully, and very positively, but my last message had said that I just needed to confirm with my significant other that I would be staying out until the next day. "So darling, I was just about to let you know my plans when your petulant reaction to the texts spoilt the evening. Anyway, I've told you now, so I will text him back that it's a date."

John cant get his words out quickly enough, "Oh Mistress Rebecca, I am so sorry. I didn't mean to criticise your manners. I just didn't think properly. Of course you need to answer urgent texts. I apologise for being so silly. I should really be thanking you for thinking of me before you confirmed. Please forgive my rudeness."

I smile at his eagerness to explain himself. "I understand John. Don't worry yourself. I know it's hard getting used to a new situation. We can't expect everything to be perfect from day one now can we? Now, you tidy everything up in here and I will go and relax in the living room." I get up and give John a warm kiss, then go out of the dining room, through the hallway and into the living room.

I text Carl to confirm tomorrow night, but also tell him about John. Carl is pleased that I have found a willing cuckold, but is a bit worried that maybe John isn't as accepting of the situation as I have made out. I assure him that John really is on board, but he wants to hear it from John himself. Half an hour later after hearing pots and pans, chinaware and cutlery splashing and clattering I see John stepping into the living room. He goes towards the big armchair in the corner, but I beckon him over to me on the sofa. "You don't have to worry about your silly outburst earlier. I do understand how hard it can be and I know you didn't mean to disrespect me or Carl. Carl would like you to call him, just to check that you are cool with tomorrow." I hand him my phone and he sees the call ready to be started. He looks at me... hesitates, then presses the green button. This is what I hear:

"Hi, yes, this is John. Um... Rebecca's ummm cuckold.

Thanks, yes she is....

Em, I just want to tell you that I am happy for Rebecca to go have dinner with you tomorrow night...

Y-yes and stay the night

Ummmm (John hesitates, listening)

You need me to actually say it? Um ok

You can fuck her. Yes in the pus... ok, in the cunt

And in the face yes...

And in the asshole.... (John is blushing deep red and looking quite worried)

A buttplug, ok I'll ask her.

And yes, I'll drop her off at 8.00 and pick her up at 10.00 the following morning. Thank you, Sir."

John returns the phone to me and I wrap up the call saying I'll see him tomorrow and I can't wait!

I look at John, smiling reassuringly. "It's ok John. I'm used to it. Carl loves anal sex. You will have to help me get ready tomorrow. I will need to have an enema before I meet him and the buttplug he suggested will help me be ready to take his very thick cock all the way into my asshole."

"How do I give you an enema Mistress Rebecca?"

"Don't worry John. I have everything we need in those boxes. We can fully unpack tomorrow morning. Spend the afternoon getting ready and then you can take me out at 7.30.

You know John, I have really enjoyed helping you cum these last two days and I think it would be nice for us as a couple if I was always there with you every time you cum. Do you agree John? Would you like to keep me involved in all your orgasms?"

John replies enthusiastically. "Oh Mistress Rebecca, that's a lovely idea. Yes, let's try it."

I reach down to John's crotch and feel that his little willy is hard again. "Oh John, you are all hard thinking about me and Carl aren't you? How sweet! You lie down on the sofa and I will kneel next to you and help you have your orgasm."

I slip off the sofa and kneel by his crotch and pull his panties down a little, freeing his little erection. "Awwwwww it looks so sweet surrounded by so much satin. Such a darling little willy!"

I hold it gently and start stroking up and down covering his swelling head with his foreskin, then pulling it right back and exposing everything. Each time I pull back I plant a little kiss on his most sensitive part or give it a little lick. I raise my body a bit unbending my knees and hover my mouth above John's eager little willy. I open my mouth and sink down onto it slowly. Engulfing the throbbing organ in my warm wet mouth. My tongue swirls around his swollen head and I suck gently. My head starts going up and down as my hands caress his balls. That is all it takes to push him to the edge. I feel him tense up as his skin all reddens. Then he shoots his load into my warm mouth.

"Thank you Mistress, thank you. I love you so much."

I move over so that my head is above John's and I lean down to kiss him. He opens his mouth and I allow his sperm to flow down into his waiting mouth.

"Eat up, there's a good boy."

I move back to his crotch and take his now soft willy into my mouth again. Sucking the last drops that ooze out of his peehole and pulling his panties back up to cover his little soft willy.

"There you are John. That's better isn't it?"

"Yes, thank you Mistress"

I kiss him gently and say. "Right, time for bed. Let's get upstairs John. We have a big day tomorrow."

I climb the stairs as John locks up and turns off all the lights. When he gets up to the bedroom. I am already in bed, with his side of the covers folded back welcomingly. He climbs in and cuddles up with me. We hold each other and kiss lovingly. We start to relax more, each closing our eyes as our breathing synchronises. We both drift off to sleep happy in our new togetherness.

Next morning, I am up first. I shower and get dressed casually in jeans and a loose top. I put my hair up in a bun and don't put on any make up. I go straight downstairs and have my first real exploration of the kitchen, as I hear the sounds of John showering and dressing upstairs. I eventually find everything I need and manage to rustle up a nice breakfast for two with coffee, cereal and warm croissants. Just as I am setting the table, John comes into the kitchen. He is wearing cotton chinos and a Lacoste polo shirt. Very 90s man about town and quite handsome I have to admit, but I am disappointed that he is not just in ladies' lingerie and wonder why...

He comes over and gives me a warm kiss on the lips. "Good morning Mistress Rebecca."

"Good morning John. Why are you dressed like that. I though you always wore lingerie about the house. That is what you told me. I wasn't expecting to see you looking like a man about town."

John blushes. "Sorry Mistress, but I am expecting a delivery this morning and... erm... I didn't want to embarrass anyone."

"Oh John, I thought more of you than this. I thought you accepted who you are. Your little willy has been so erect and so proud with me. Bursting out of those lovely panties you wear, desperate for attention. I'm sure a delivery driver won't care what you are wearing. Listen, maybe if the lingerie is too much for a stranger, what if you wore a full lady's outfit? That would not be indecent. You would not be showing your underwear. What do to think? Can we compromise? Could you stay true to yourself, while not offending any visitors?"

"Oh Mistress Rebecca, you are so insightful. I had honestly not though of that. I could take you on a shopping trip and we could both buy some new outfits."

"Good idea John, but not today. We have too much to do before I meet Carl. If you like, I could lend you something like a loose fitting skirt and blouse, I think I may have a few suitable outfits. Now, get out of that silly man's outfit and let me see what you have on underneath."

John strips down to his lingerie and I am greeted with another beautiful matching set of black silk with red trimmings.

"That's lovely John. You look beautiful in that. So much better than that silly man's costume you had on. Now sit down and have your breakfast with me."

We sit and eat together smiling and touching hands often as we talk about everything we have to do today. When I have finished I say. "Ok John. I will go up and find some suitable clothes for you, just for today, you can tidy up in here before we start unpacking my boxes."

John gets to work eagerly and I go upstairs to find something he could wear. Just as he is putting away the last bowl I come in with a plain black skirt and a loose pink knitted top. He puts them on eagerly and I watch him smiling. "Give me a twirl John. How does it feel?"

"It feels wonderful Mistress. Thank you for letting me wear your clothes and sorry for being so silly earlier. I see a bulge in the skirt he is wearing and smooth it down with my hand. "Whoops! What's that?"

I lift the knee length skirt to reveal his black silk panties bulging with another erection. "Oh John, look at you. All aroused by my outfit. Poor little boy. Shall I help you deal with that?"

"Yes please Mistress." John says meekly and without me saying anything he walks over to the living room and lies on the sofa. He pulls his skirt up and his panties down and waits for me to come over.

"Good boy John. You get nice and comfy and I will look after that silly little erection. I take his hard little willy in my hand and start to slowly stroke him up and down. After a short while he starts to tense up, but I keep stroking faster and faster. Surprised at how long he is lasting I grip harder and jerk faster. Eventually, after my right arm is feeling really tired John's whole body jerks and he spasms on the sofa. His little willy throbs and a tiny dribble of cum appears out of his little peehole in his swollen head."

I look at him quizzically. "John... is there something you need to tell me? After a full nights sleep, I would have expected a lot more sperm than this. Do you remember our conversation about me always being involved in your orgasms? Well, did we not agree that I was always to be with you when you orgasm?"

"S-sorry Mistress, I didn't think this morning in the shower."

I stand up abruptly. Looking down at John sternly. "You fell at the very first hurdle John. Maybe I have been wrong about you. Maybe you just don't get it. Maybe you are not ready to be with me. I can easily give Leon a call. After all we haven't fully unpacked yet. A man's outfit at home and a solo jerk in the shower. Not a great start to the day..: and after I made you breakfast too."

Now I am more talking to myself than to John. "It had to be too good to be true. He is just playing games like every other man I have known. I shared my innermost feelings and he just thinks I am wank fodder like Pornhub. No understanding of what we could have had together... Tears start to roll down my cheeks as I bury my face in my hands. "After all that talking, zero understanding." I shake my head dejectedly and turn away from John. I go out into the hall and then trudge sadly up the stairs.

I lie on the bed and my mind wanders back to when I was 19 years old. I was dating an older man and he was very dominant. David had been spanking me regularly and we had had fantastic sex. I started being bratty and insolent towards him to make him need to spank me more and more, but instead of making things better, my immature behaviour started to make the relationship go off the boil. He was getting sick of my playing up and eventually sat me down and told me it was over between us. I was so shocked, but eventually realised that playing at being submissive by being bratty and disobedient was actually the opposite of being submissive. I often wondered what would have happened if I had behaved differently with David. Maybe be we would still be together in a real sub/Dom relationship.

Now, John had really only made one mistake with me and it is really early days. Maybe this can be salvaged if I really make him understand how seriously I take this. I decide after 20 minutes, to go down and see if I can talk to John. I find him sitting on the sofa crying and I sit next to him and put my arms around him. "Shhhh shhhhh John. Let's talk calmly about this. Are you ready to talk and to listen. This is our last chance, but I need you to understand what you have done wrong and how that kind of unthinking stupidity could end our whole relationship. Now, stand up and tell me how you feel, what you did wrong, why it was wrong and how you hope we can move forwards from here.

John started talking and he did seem genuinely sorry. He said he knew as soon as he orgasmed in the shower that it was a mistake, but I don't even believe that, because if it was true, he would have come straight down and told me about it. We would have been able to sort that out together, because he would have shown the maturity to acknowledge the consequences of his actions. He carried on promising to behave better and follow my rules, but he didn't seem to get that they weren't rules. They were an understanding between two mature adults. What he was really telling me was that he needs rules, discipline and punishment to be able to control his urges. Just the promise of a feeling between two adults is beyond his comprehension right now. Could he eventually learn? Who knows? But for now we need a completely different basis for this so called relationship. I guess the first red flag for me should have been him calling me Mistress. That had not occurred to me before he said it, but it is obviously what he needs and craves - a dominatrix in black leather, with whips and chains!

What should I do? I had been hoping for a kind of sharing relationship where we both understood each others' needs and desires and he would acknowledge his sexual inadequacy and enjoy having a partner who could give him release and satisfaction, while also sharing my own submission to true men who knew how to take me and use me like I deserve to be used, safe in the knowledge that I could go home to him and have his love and devotion. I am so close, but maybe there is not a man in the world who could cope with all I have described.

I am sorry to say that I did ring Leon later that day and he came at around 3.00 to pick me up. The look he gave John when he arrived made me feel sorry for poor little John, but trust was lost and there was unfortunately no future for us...