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 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.
