The more I became entwined with Mistress R and her clients, the more her work fuelled and powered my sexual addiction. And like most addictions, there were negative side effects. For me it was the impact it was having in the relationship with my boyfriend T.

Not the actual sex, as I knew my boyfriend was sleeping around with others at the same time, and I never cared if he did. Monogamy was not something I demanded or required in a relationship. However living three hours away, the time I spent in the city was stretched thin between entire weekends spent with Miss F or with Lady M – not to forget the time I spent alone with Mistress R. Mr EU only took up a few hours at most and was easy to slot around Miss F or Mistress R.

But lost among them was I not bothering or paying attention to maintain my relationship with T. I was failing at that due to my blindness of my situation. When T had voiced how we rarely saw each other, sometimes I brushed him off and sometimes I suggested that he visit me more often. However his visits to me confined us to my apartment. In my own home town I was closeted and too afraid to go out with him in public, because sooner or later personal or family acquaintances I knew, who knew nothing about my true sexual nature, would inevitably cross paths with us and figure us out.

My life in those years was an unstoppable whirlwind of sex that I was just hedonistically riding with no direction in mind, but T’s life was nearing crossroads where he needed to make some career decisions, some of which would require him to relocate some distance away. Whenever he brought up his career, I told him don’t let me hold him back at all.

We both knew that a long-term relationship or anything more serious was completely out of the question for me. I knew at some point I would need to land or crash back down to earth and reintegrate with my family – and there was no possibility or place for a gay relationship in that mix. I had made that clear to him, numerous times: ‘if you need to better yourself, then leave and look after yourself.’

In time, we would go our separate ways. We didn’t break up, officially. We just drifted farther and farther apart until one day we stopped seeing each other and stopped calling each other. But in those dying days of our relationship, T would play a part in setting me up with my fourth and final client (or, rather, clients) for Mistress R.

* * * * * * *

Unlike my three other clients, I had, in a manner of speaking, met my next clients although I didn’t know it at that time who they were.

When T worked as a male prostitute for Mistress R, the couple had been regular clients of his.  Even after he stopped doing paid work for the Mistress, he still met with them on a semi-regular basis for sex with both of them. This irked Mistress R but there was little she could do but privately protest her disapproval to T, because the couple really liked him and she did not want to cause a split with them.

The background details were never explained to me how I got offered up to them, but looking back and putting the various pieces in place that I observed or heard, it felt to me that T and Mistress R had come to some mutual understanding and I was the commodity exchanged between them, with my boyfriend using me (and my insatiable sex addiction) to find a solution for Mistress R and her two clients as well as perhaps create more of a wedge between him and me, as I would see him even less than before. What was obvious to me was that both T and Mistress R were fully involved in conspiring to set me up with these new clients.

* * * * * * *

Mistress R telephoned me one night at home midweek. Not uncommon, but those calls always meant that something important was to be addressed or attention required.

‘I am holding a cocktail party in two weeks when you are here next…’, my first thought being that she was planning another gangbang session and wanted me part of it, before she continued ‘…and I want both you and T to attend, together, as part of the invited guest list’.

My curiosity was at full attention. Obviously thinking this was future sexwork, soon came some of my questions. ‘Are you shopping me around? How do you want me to dress?’

‘Yes, I am. And, this is a delicate situation for all involved, which requires upmost discretion. Do you understand?’ – ‘Yes, of course.’

‘I also want you to show up wearing full drag, and act publicly during the event as T’s date.’

‘Sure, but you know I don’t do drag well, but I’ll try pull it off. How do you want me to act?’ – ‘Act your bi-self but the more you can play up your fem side, the better. I know yours and T’s relationship is rocky right now, but if you can play it up, I would be appreciative and happy. This couple likes boys like you and T’.

‘A couple…?’ I asked in amazement. ‘Yes, a couple. And if they like you, which I hope they do, they’ll both want a piece of you.’

* * * * * * *

The event was scheduled for a Saturday evening, so after a quick morning fuck session spent with Mister EU, I then returned to Mistress R’s studio and spent the rest of the afternoon there cleaning up and preparing myself. She had an old claw-foot bathtub in her personal bathroom there which I liked to use, so I soaked in it and shaved my entire body. On my way back to the studio, I had stopped first to get my hair trimmed down, as it was getting a little too long for me to wear a wig comfortably.

For my outfit, I opted for my black cheongsam, forgoing the inflatable bra underneath as I wanted to show with my flat chest there was a boy underneath all of this. The dress was short so I wore some black opaque stockings gartered to my corset which I wore under the dress, the corset both an arousal item for me as well as a necessity so I could fit inside the snug dress.

To top everything off, I wore my black bob wig and powdered my face with my geisha oshiroi white powder, before applying some black lipstick. I then slipped into my favourite five-inch heels, the ones my boyfriend had bought for me. I then went looking for Mistress R, who was working at her desk, to get her critique and approval.

“So, how do I look?” – Mistress R was very happy with my appearance. “Wow, very nice. I wish you would dress like that for me sometimes.”

She then pulled over a chair near her and motioned for me to sit down. She wanted to talk, explaining to me in serious tone the sensitive nature and discretion required for this couple.

* * * * * * *

An hour or so later, the guests began to arrive at Mistress R’s studio – including my boyfriend T. As soon as I saw him appear, I immediately made my way over to him and kissed him. Throughout the evening I could sense the mental distancing between us, but I did my best to stay close to him physically. Sometimes he put his arm around my waist, and I would hold on to his hand there as I did not want it to leave me.

When we had a quiet moment together, I asked him ‘What do you know about this couple that Mistress R is shopping me out for? She said you have history with them.’

He explained to me that he met them one night while he was working at the restaurant, when Mistress R came in with both of them as a means of introduction. They were both very rich and somewhat known around the city, well at least the woman was, as she was a dealer in high-end artwork and had a gallery downtown. Her husband was some sort of international banker or accountant. On the surface they maintained a close relationship both for the sake of their business as well as their family appearance – as they had two or three adult-aged children, T couldn’t remember for sure.

But behind closed doors at home, it was a different matter. He was gay and in the closet, although his secret sexuality supported by his wife who had apparently known ever since they met as teenagers. Meanwhile she had her own proclivities as well, a raging sex drive and a craving for young men to fuel her – and by men, sometimes plural, as in two taken at a time and preferably those willing to sleep with both her and her husband. This was where T had caught their mutual attention and desires, and for around three or four years up to and including time when he and I were an item, he had satisfied both of their sexual needs. All of this was hidden from their public persona and their family life behind the façade of their marriage.  

He finished up his summarization with ‘They’re nice – I know they’ll like you and I think you’ll like them. Keep them safe, and you can trust them.’

I knew T had ‘cheated’ on me behind my back, never saying with whom, so it was now a little strange to finally meet some of the ‘competition’. I didn’t have to wait long as a few minutes later Mistress R brought them both over to where T and I had been standing off in a corner.

Directed toward my benefit, Mistress R said ‘I’d like to introduce you to Mister and Mrs…’ – but for the sake here I will call them the Moneybags.

‘Hello T, always good to see you my boy!’ the lady said as both T and her exchanged affectionate kisses on their cheeks. I don’t know why but for some reason I felt really nervous, as Mrs. Moneybags then shifted her attention to me, held out her hand to shake. ‘Oh my, and this must be your wonderful boy I have heard so much about, so much about indeed!’, at which I gave a sheepish smile in reply as I shook her hand.

T was right, she could barely constrain her hormones as I could feel her predatory gaze scanning all over me, like she was searching me out for something. And then it hit me, I suddenly recognized her voice! She was the same woman who had come into the fuck room when I was tied up and blindfolded doing the gang bang hors d’oeuvres. I looked at her hands, with their long painted finger nails, the same hands that had groped my ass and tugged on my penis with approval.

Mistress R then made room, gently ushering her aside, so I could then have the opportunity to meet her other half – and his voice, too, I also remembered from the fuck room. As I found out later, he had indeed plowed my ass that night although neither knew at the time my personal connection with T.

It’s strange when you fuck someone you cannot see, and how you image them to look and then how similar or different they are when you finally get to see them. He was much better looking than I was expecting, taller than me by a couple inches. Despite being in his 60s with a full head of silver, short hair, I found that I fancied Mr. Moneybags as being more attractive looking than Mister EU who was probably 5 to 10 years younger than him. She was, I think, very late 50s but hard to tell with her steel grey hair, permed out and hair-sprayed into a wavy long bob. Both seemed to be a little older than my own parents, which unsettled me at first until I got to know them more intimately, that age often does not matter if in similar frames of mind.

If I had not ever been a prostitute, I would never thought for a moment of having sex with someone more than a few year older than me. But all my clients were much older than me and I soon learned that it was very easy to please older sexual partners when you are the younger male in the mix – especially with older women.

Just from our introduction alone, I knew right then and there I had them hooked on me, so I decided to play the rest of the evening more coy and evasive and not seem too eager on the surface.

* * * * * * *

When I wore full drag, it was not something I usually found pleasant or enjoyable. For starters I always kept talking with those I did not know to an absolute minimum, or at a whisper, because I really didn’t like how my odd accented voice went with my appearance.

Plus, now, there was the constant lingering tension with my boyfriend, now taking a strange new twist by how I was being offered up like a piece of used meat by him and Mistress R to these newcomers. If I felt like my relationship with him was nearing its conclusion, then here I was now being handed over, by him, for others now to have their turn and fun with.

Of course the pervert and slut in me was excited by prospects of new fun flesh to fuck and be fucked by, but at the same time I felt like his garbage being taken out to the curb for others to pick over. Looking back now however, I have only myself to blame for neglecting him.

Mulling all this over put me into a foul mood inside so it just made it easy for me to play-act hard to get.

* * * * * * *

An hour or so later, and with a couple drinks deep inside of me, I decided to see what would happen if I wandered off alone. Sure enough, both of them had been keeping one eye on my movements all night – and once I was alone, he made the first move.

I had gone out into the hallway of the studio’s floor with the premise to get some air. There was a glass-windowed door at the end of the hallway, so I had gone and opened it, so I could look out on the small one-person balcony adjoined to it. I soon sensed someone approaching behind me, so I turned around to see who it was. Mister Moneybags was there, with a drink in hand, for me.

‘The bar told me you like…’ as he handed the drink to me. ‘Thanks’ I said quietly and demurely, thinking actually how shy Miss F would have acted in a similar situation, as how I would play him.

We launched into some small talk, with him doing most of the talking, explaining some background, although cautiously guarded, about both of them. Much of it I already knew from Mistress R’s preparation talk, but I played it interested as if I was hearing for the first time. He also asked what I did for work, where I was from, and some general harmless personal questions about what I liked for pastimes and stuff.

He then asked me about T, initially very general enquires before becoming more specific and pointed, as I sensed he was trying to scout out how intimate T and I were, and whether that intimacy could be replicated between him and me. I played it vague and shy but still just enough details thrown his way to hopefully excite him.

We spoke for around half an hour until he took leave of me. T was correct, he was nice. I felt that if I could have sex with Mister EU, then I could certainly have sex with him.

* * * * * * *

Then, expectedly, almost like clockwork, his wife Mrs Moneybags made her own move, zeroing in on me like a shark for the kill. Where he was reserved, sincere, and delicately polite, she was much more brash and to the point.

‘So, my boy, you are the one that T hides from us!’ – ‘Yes, I suppose I am’, I laughed, ‘although I could say the same about him and you.’

‘Does it bother you… you know, about him and us?’ She was trying to imply all the fucking between the three of them, said in a tone conveying as much innuendo as possible.

‘No, not at all. He is free to be with who he wants to be, and the same is true with me. We are not each other’s masters’. – She replied with a slow, slinky ‘…good’

She stood there, looking at me shifting her pose as if trying to get different angles of view on me.

‘You’re quite a pretty little faggot, aren’t you! So do you dress like this all the time?’ – ‘No, not too much, well, not like this exactly, but I do like to wear this and that when I go out clubbing. Or when I play with others’, giving her a wink when I said the word ‘play’. I then added, ‘And I’m not really a faggot, as I enjoy women as much as I enjoy men.’

‘You do, do you?’ she commented, then adding ‘well, I like faggots who like women, so we shall see about that, sometime…’

In my head I could hear the ringing of an imaginary cash register sounding off. I then thought to myself: I wonder how fast it will be before I am bedding these two?