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Becoming Chrissy

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Author’s note. This is a story about Dominant/submissive relationships. It includes descriptions of cross dressing, BDSM, cuckolding, enforced chastity, incest and some other aspects of a Female Led Marriage. All the fetishes described are performed consensually, and all participants are well over the age of eighteen. If any of the above offends or does not meet with the reader’s approval, do not read this story.

Chapter 1: The First Time. (Autumn, 1993)

“There we go. All finished.”

My wife of nearly thirty years, stepped aside, leaving me to look at myself in the full length mirror in our bedroom. I had one hell of a shock. I was transformed. And without wishing to sound boastful, I looked gorgeous. Well, I thought I did, anyway, and judging by the way my cock was sticking up, I wasn’t too far off the mark. I smiled, and my fully made-up reflection smiled back at me.

“Oh, Olwen,” I said, “it’s even better than I imagined. Thank you so much, dear.”

My wife frowned.

“What did we agree?” she asked in a cross voice. “When you are dressed and wearing your make up, you refer to me as ‘Madam’ and you don’t speak in Christopher’s voice. If we are going to make this work, you have to remember the rules.”

“I beg your pardon, Madam,” I replied, blushing. At the same time, my cock seemed to me to get even harder. The humiliation of being made to look and sound like a woman was such a thrill for me.

May I introduce ourselves, and give you, the reader, a brief explanation of what was going on in the scenario that I have described above? It was all so new then, and although I didn’t know it at the time, that evening in early October, 1993 was to prove to be a very significant date indeed.

Olwen, my wife and I have been married for twenty nine years. We are both in our late forties, although I am three days younger than Olwen. She has always referred to me as her ‘toy boy’ as a result.

We met at a swinger’s night at a fetish club in a town nearby to where we both lived at the time. Although it was advertised as a swinging event, submissives like me went along in the hope of some action. I certainly struck lucky. Olwen had attended the event seeking a new submissive partner.From the moment we were married, we enjoyed a Female Led Marriage, and within a year I was playing the role of cuckold as well as that of Olwen’s submissive.

Our two children, Mary and John were born eighteen months apart, and have long flown the nest. Mary is married to a fellow barrister, and they live a few miles away from us, although they tend to keep themselves to themselves. We see them a couple of times a year, which is great. It means our chosen lifestyle can remain private.

John came out as gay whilst at University, and he now lives in Berkeley, California, with his husband, who is also called John. They both lecture at the University of California, Berkeley, but, unlike Mary and Dewi, neither of them really come into this story.

Whilst the children were growing up, we were very discrete. Olwen still went out and met her lovers, returning to feed me cream pie, which I loved. But the days of me coming home from work and being taken upstairs for a spanking or a pegging (or both!) dropped away until they disappeared altogether. Our FLM continued, but without the added spice of regular play sessions. I had to be content for a number of years with being a cuckold.

At some point, just after lap top computers were becoming all the rage, Olwen suggested that we watch porn together. I agreed and we started off watching some appalling stuff, with no plot, ‘starring’ viagra-enhanced men who always seemed to keep their socks on, and pneumaticly inflated women who gasped and groaned their way to scarcely credible orgasms. It did nothing for us.

We diversified and started to look at Hot Wife and cuckold clips. This was much better! We got into a routine whereby we’d watch clips during the week, and on weekends Olwen would go off for a date at the local fetish club, and on her return, she’d tell me all that her latest lover had done to her. She always got fucked, and one night she returned home having been fucked in her cunt and up her arse. That was a really lovely double helping of cream pie, and it led to the next step in our FLM fetish lifestyle. It happened like this.

We were by now regular attendees at a local swinger’s club. Twice a month, Mary and John would spend one weekend with Olwen’s parents and one weekend with mine. We took advantage of their absence and joined the club, making quite a few new friends in the process. Our preference was well known. Olwen would make herself available and allow her lover to fuck her whilst I was made to watch. If I’d been good, I would be fed a cream pie.

Olwen was being fucked by Eric, a young black man one evening. He seemed to have no objection to my standing in the corner watching him and Olwen fucking. After he’d finished and they were both recovering, he asked Olwen if she was interested in becoming ısparta seks hikayeleri his regular fuck partner.

She never even hesitated. Smiling at him, she nodded eagerly and winked at me.

“You’ll be getting regular cream pie from now on, cuckold,” she told me with a grin.

What neither of us knew was that Eric was bi-sexual. He bided his time until Olwen was really hooked on black cock. One weekend, when the children were away on a school camping trip, he stayed with us. That was the first time I ever fluffed a lover of Olwen’s and cleaned him up after he’d fucked her.

The thought of being made to suck a man’s cock was so humiliating. I loved it, and when Eric actually put his cock in my mouth, the look on Olwen’s face was priceless. We had a threesome in bed that night, and although it was a while before Eric actually fucked me, Olwen’s imagination had been stimulated.

Over breakfast the next morning, Eric made a suggestion.

“Christopher is a very good looking man, Olwen,” he said with a smile. “You ought to consider turning him into a sissy. In a nice flouncy, frilly dress and with some make up and a wig, he’d be a very pretty sissy. I’d certainly fuck him, and he’d be a big hit down at the club. They have a sissy night a few times a month.”

I held my breath. Olwen looked at me, her head tilted on one side as she considered the possibilities.

“It would be a great idea,” she agreed. “The only problem is the children. They know nothing about what we get up to, and it’s only because they’re away this weekend that we’re able to host you here. I intend making the most of you,” she added with a grin. “After breakfast I want to go back to bed for some more of your lovely cock!”

Eric continued as Olwen’s lover for a number of years after that weekend. He also took control of me. By the time he announced that he was leaving the area to take up a more senior position in his company, he’d been fucking both Olwen and me for over five years.

In the lull in playing after he’d gone, Olwen and I were mainly occupied with making sure that John emulated his sister and passed his school exams and went to University. Mary had already left home and was well into her second year of a law degree.

When John left home the following year to go to study for a business degree, we breathed a sigh of relief. We were alone again in the house. The first weekend of freedom that we enjoyed was spent down at the swinger’s club.

Over the years, the membership of the club had changed. Many of our friends no longer attended, having ‘grown out’ of their swinging phase. Olwen and I were the opposite. We wanted to make up for lost time.

By coincidence, that first weekend back just happened to coincide with a sissy weekend at the club. Following an increase in membership of the club, a lot of unfamiliar faces were in attendance and Olwen hooked up with a couple who had no objection to letting me watch.

Seeing Olwen with a man (even a man wearing a dress and full make up) and another woman was mind blowing. She was being spit roasted, sucking the sissy’s cock whilst his wife fucked her with a strap-on from behind.

Viv and Larry became Olwen’s regular lovers and my Mistress and Master. They were both bi-sexual, and when Olwen mentioned that she was considering sissifying me, they both were very enthusiastic. Larry had already been transformed and was a regular sissy to Viv and her many lovers.

Viv was a doctor and she was able to put me on the same course of drugs as her sissy husband. I took them regularly, and they gave me man boobs like Larry. When Olwen took me to buy my first corset, I was thrilled when wearing it to see that I had a cleavage.

“Now don’t forget. Tonight you are Chrissy the Sissy, not Cuckold Christopher,” Olwen warned me as I made my way downstairs very carefully. I’d been practicing wearing high heels, but I still had the occasional stumble.

“I’ll be fucking Viv and possibly Larry, of course,” she continued, “so Cuckold Christopher will get his cream pie later on, but I want to see Chrissy the Sissy on parade tonight. She is to suck as many cocks as she can, and her arse is to be available to all and sundry. I mean to expose you to as many club members as possible this evening!”

We were going to the club to meet Viv and Larry. This would be the first time I’d ever been out of the house whilst dressed. Olwen stood in front of me in the hallway to give me the last check over.

“You’ll do,” she giggled, brushing her hand over my rampant cock, which was causing my skirt to stick out in a very obvious way.

She picked up her hand bag, handed me mine, and we went out through the kitchen into the garage. Although it was October, and the evenings got dark quite early, neither of us wanted to shock our elderly neighbour, who spent a lot of time these days staring out of her front window.

I lay down on the back seat of the car, and Olwen drove out of the garage and headed for our destination, the local swingers’ club.

It was only a fifteen minute drive to the club. Olwen parked the car and arm in arm we made our way to the discrete building on the edge of the town’s industrial estate. To the uninitiated, it was a lap dancing club, but to the aficionados, it was a swinger and a fetish club. The local council turned a blind eye towards what went on there, mainly it was rumoured, because so many councillors were members.

We walked in, showed our membership cards and Olwen asked Cindy, the receptionist if I ‘d need another membership card in Chrissy’s name.

Cindy giggled.

“No, I don’t think so, Mrs. Simpson,” she answered. Olwen tutted.

“I wish you’d call me Olwen,” she said with a mock glare. “Mrs. Simpson makes me sound so old!”

Cindy blushed. I knew that Olwen had taught her in junior school many years ago, and old habits were hard to break. We both smiled at her and went into the bar area of the club.

Viv and Larry were there already. They were on the lookout for us, and as we walked in, Larry raised his arm in greeting and waved us over.

“Remember, it’s Chrissy the Sissy mode,” whispered Olwen as we made our way over to the booth where our friends were sitting. “Don’t use Cuckold Christopher’s voice.”

“I’ll remember, Madam,” I replied in my sissy tone. My cock throbbed as I imagined what was going to unfold.

When we got to the booth, Larry was on his feet, smiling a sincere welcome. Wearing a1950s style vintage dress, with cinched waist and a full skirt, with red lipstick and elegant made-up eyes, he didn’t need to wear a wig. With naturally curly hair, when he was dressed, Larry wore his hair in a classic 1950s style bubble cut. He kissed Olwen full on the mouth and helped her to sit between himself and his wife. Viv put the cigar she was smoking down in an ashtray and kissed Olwen too.

“Well, what have we here?” drawled Viv, picking up her cigar and puffing a cloud of blue smoke in my direction. She knew that Larry and I shared a fetish for women who smoked. She’d even introduced Olwen to cigars, much to my delight.

“Good evening, Mistress Vivian. Good evening, Sir,” I lisped in my best sissy voice. “May I get you both a drink?”

“I’ll have a gin and tonic with a slice of lime and plenty of ice,” replied Viv, and Olwen nodded in approval.

“Same for me, Chrissy,” she said curtly, taking her cigar case out of her handbag.


I addressed Larry.

“Whiskey,” he replied, smiling at me. “Irish, of course. No ice.”

I turned away to go back to the bar. I’d gone about five yards when Olwen called my name. I returned to the booth.

“You may get yourself a drink,” she smiled. “Something appropriate for a sissy. I don’t want you drinking pints of bitter tonight.”

“Thank you, Madam,” I replied. “Is a crème de menthe cocktail appropriate?”

Olwen considered her answer as she lit her cigar.

“A frozen grasshopper seems perfectly girly,” she replied, “and the lovely green colour will go with your hair!”

(Olwen had put a subtly tinted red wig on me earlier).

I went off in search of the drinks.

At the bar, I stood waiting whilst the young barman served a couple that I didn’t know. Behind me a voice said,

“Well aren’t you a pretty little thing. Do you come here often?”

I turned and smiled at whoever it was that had spoken. It was a silver haired gentleman, who smiled back at me.

“Good evening Sir. I’m Chrissy, and I’m here with my Madam. She intends playing with her girl friend and her sissy this evening. I believe that the two ladies are looking for some real men to fuck.”

“Well that seems most unfair. Playing with her friend and leaving you out. What does she intend for you whilst she’s getting herself fucked?”

“I may be permitted to watch, Sir,” I replied. “And I’m hoping for a nice cream pie at some point in the evening.”

“Do you think I might be permitted to give you an hors d’oeuvres before your main meal?” he asked, unzipping his trousers and taking out his cock. Members were never shy of making their intentions known at the club.

“My instructions were to suck as many cocks as possible this evening,” I admitted, feeling my own cock stirring and beginning to push my skirt out at the front.

“I’ve been sent to the bar to get drinks, but the barman seems to be busy. I’d be happy to suck your cock whilst we wait.”

Carefully kneeling to avoid laddering my stockings I opened my mouth and he slid his cock in. I love feeling a soft cock thicken and harden in my mouth. I had sucked a fair few since Olwen had become a Hot Wife and transformed me into Chrissy the sissy.

He tasted fresh and clean and he was soon rock hard in my mouth. I bobbed my head back and forth and within seconds he was leaking pre-cum. I heard the barman coming over and it occurred to me that Olwen, Viv and Larry wouldn’t thank me for keeping them waiting for their drinks. I bobbed quicker.

My mysterious gentleman friend’s breathing quickened.

“I’ll have a large scotch on the rocks,” he gasped in answer to the barman’s question. “Oh fuck! That’s nice! This sissy is an excellent cock sucker!” he said, presumably to the barman.

He gripped my head, knocking my wig askew, but we were both too far down the line now to stop to make adjustments. He started to skull fuck me.

My eyes,nose and mouth were all streaming as I struggled for breath. At last he gave a final thrust and I felt his cock explode in my mouth. A lovely thick strand of hot cum filled my mouth, and I swallowed just in time to receive the second blast. I swallowed that too, and the subsequent weaker pulses. His cum tasted wonderful, hot, thick and creamy.

When he’d finished cumming, he pulled out of my mouth carefully and thanked me, putting his by now soft cock back in his trousers and zipping himself up. He waited until I had adjusted my wig and then he helped me to my feet.

“Thank you, Chrissy,” he smiled, handing me a clean paper handkerchief from a box on the bar. I blew my nose and wiped my eyes. My make up would be in ruins, I knew, but it would have been anyway by the time Olwen, Viv and Larry had finished with me. And I was under orders to suck as many cocks as possible that evening.

Picking up his drink, he sauntered off without another word, raising his hand in a gesture of farewell as he left.

“Well you certainly put a smile on his face,” grinned the barman. “Did you recognise him?”

When I admitted that I didn’t know him from Adam, the barman smirked knowingly.

“That was Councillor Joe Morgan. It’s thanks to him and his fellow councillors that this place is never bothered by the authorities.”

“Now then, unless you’d like to come behind the bar and suck my cock too, what can I get for you, my pretty sissy?”

Sissies like me never hesitate when given such a choice. I raised the bar flap and went to join him behind the bar. I gave him my drinks order and sank to my knees again. It would take a couple of minutes for him to pour all four drinks. I was confident in my ability to empty his balls before he’d completed my drinks.

When I eventually got back to our booth, Olwen was lying on the table with her legs apart. Larry had his face in her cunt and Viv was behind him, pegging him slowly and deeply. They were all so engrossed in what they were doing that no-one noticed me. I stood with my tray of drinks and waited patiently for them to finish.

Eventually Viv looked across at me and smiled her beautiful, cruel smile.

“I’ll get to you in a minute,” she said, continuing to peg her sissy’s arse. “From the time you’ve been away, and judging from your smudged lipstick and panda eyes, I’d say that you’ve been sucking cock. Am I correct?” She reached across without breaking her rhythm and took her gin and tonic.

“Perfectly correct, Mistress Vivian,” I replied. “Madam told me that she expected me to suck as many cocks as possible this evening. I was doing what I was told.”

Olwen was writhing in ecstasy on the table in front of me. She’d obviously heard my confession, and coupled with Larry’s cunt eating technique, she was exceedingly turned on.

“Hurry up and finish pegging him, Viv,” she gasped. “I don’t know about you, but I’m gagging for some proper cock. We can leave these two sissies together and go in search of some real men!”

Viv pulled out of Larry’s arse, and he gave a yelp of pain. He stood up straight and helped Olwen off the table. Larry always had perfect manners, even when his face was red and sweaty and covered in cunt cream.

Olwen took her gin and tonic off my tray, and clinked glasses with Viv.

“Here’s to some proper cock,” she toasted her friend, and they both drank deeply.

“Behave yourself, Chrissy,” muttered my Hot Wife as she sauntered off. “Don’t forget my instructions. I want to hear that you’ve sucked at least six cocks before we go home tonight. I’ll have a nice cream pie ready for you!”

“So will I,” smiled Viv, leaning in to kiss her husband. “Don’t neglect Chrissy, dear. That pegging seems to have given you quite a nice hard-on. It’s just a pity that even fully hard your cock resembles one of those cotton buds I use for my make up!”

Larry grinned self-consciously, and raised his glass in a toast to his departing Hot Wife.

“Bring us both a cream pie back,” he called before turning to face Chrissy.

“Sit down, sweetie,” he invited. “I think it’s time you and I smudged one another’s lipstick even more. Now are you going to suck me off first, or would you prefer that I went down on you?”

Chapter 2: Unexpected Visitors (December 1999)

“Now remember Chrissy. You and Larry are here to serve tonight. Viv and I have worked very hard to persuade these two young men that you two sissies present no threat to them. We’ve told them about you and Larry, and they’re both ok about fucking us whilst you two watch. But once things get started, you both will be on fluffing duty. Then you may both stand in the corner and watch until you are required for clean up. Do you understand?”

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