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."