A little over a year after taking over the day to day workings of our family farm, I met this pretty, reserved raven-haired woman in the town near our village. She was a couple years younger than me. I would see her around and about when running my errands, sometimes passing by her walking along the sidewalk when I drove in for work or was walking about our main market for groceries. We soon found ourselves looking at, and checking out, each other from afar, when our paths crossed.

One morning I decided to ride my horse into town instead of taking my car. As we trotted our way back home in the glorious sunshine, she came along the road, alone in her car, towards us. As she slowed down ahead of me, to give me room and pass by, she and I stared intensely into each other’s eyes until she had passed by and our eyes were forced to break contact. I felt an electric connection with her. She was unlike the rest of women in our area, and I correctly suspected she was not originally from around our area.

These encounters went on and off for some months, just us glancing at each other, never saying anything more than a smile and exchanging silent wonderment between us. She had strong facial features, a nice body shape and dressed on the playful side, although she did not show much skin apart from her knee-length dresses she usually wore – but it was her jet black shoulder-length hair with a slight wave in it that always caught my attention. If she had any identifiable style to her, it would have been closest to a toned-down rockabilly and 1950’s style.

One day I was working in one of our barns when I heard someone riding up our lane on a squeaky old bicycle. I poked my head out and saw it was her.

Her name was N and curiosity had finally gotten the better of her. She had been asking around about me, what I did, where I lived. She told me I was difficult to track down. No surprise as I had purposely kept to myself since returning back home as I had the property and house to myself – but some long-time locals, who knew me growing up as a child, ended up pointing her in the right direction. I went and got her some coffee from inside the house, and the two of us spent the afternoon sitting on the field fence talking.

N was different, perhaps because she was the first woman – first anyone – I had met since I had left my familiar youth (and sex) scene who had no ties whatsoever to it. Unlike the women in town and our area who still remained from our childhood days, most who had since settled down in marriage, or knew me as that oddball goth kid, she was new, unknown, and a blank book. She had moved to our country from Hungary as a young child, now finding herself relocated to our town due to her job posting. She had moved here around two years after I had first left home.  

Even before I met her, I was unsure about my past and how it would come to play in any relationship going forward. I had kept myself sexually inactive since leaving Mistress R and had kept to myself socially. I took it really slow and distanced myself physically with her over the next while as we met up more frequently, and I could tell she sensed something was on my mind and kept us at arm’s length.

One evening that summer she had come over to visit after work and we found ourselves sitting outside on the porch as the sun was going down. Up until then we had not initiated any physical contact, but this particular evening we found ourselves sitting next to each other on a wicker loveseat swing that hung from the house stoop overlooking our field and barns.  

Naturally and effortlessly, N took my hand. I jumped and pulled it back from her, in surprised shock, and she seemed taken aback by my sudden negative reaction.

‘What’s wrong? Sorry, I thought you like me?’ – ‘I do… but before we think about going on any further, I really need to tell you some things about me, about my past, because I don’t know how this may work between us if you find out later.’

I then came out to N and explained my secret sexual nature and my secret past – as well as how I had been trying to put that all in the past and I was now trying to write something new in my life, although I was unsure exactly what that would be. I confessed I had not been looking for anyone but our frequent encounters in passing had made her impossible to ignore.

Thankfully she was open-minded enough that I soon became comfortable with telling her my story. I did not want to lie to her and so I left out no details or toned down the explicitness. At one point I went inside the house to retrieve some of the black and white photographs (posted in my albums) I still had from those days, to prove to her my story. If she was someone I was going to become serious with, and wanted to become serious with, I wanted her to know exactly what broken goods she was getting in return.

When I had finished telling my story, I could tell she was overwhelmed by the rawness and unusualness of it all, but never once did she come across as judgmental or cut me off. She could have just got up and walked away, which I wondered through it all if she would do at some point, but she didn’t. She heard me out.

When I said all I needed to say, I sat back, looking at her, and said, ‘There you have it… all I ask is that you keep all this between us because I feel I can trust you enough to do that. And after hearing all this I have just told you, if you feel you don’t want anything to do with me, I totally get that. I leave it with you to accept or reject me.’

N sat there silent for a couple minutes, now in the dark, thinking to herself, as we gently swung on the wicker chair.

She then, finally, spoke: ‘What you did in the past, is now in the past. Look, I’m not into any of that stuff, but so be it if you were. What I am more concerned about, here and now and in the future, is your bisexuality or whether you would stray with other women. If we do get together, I want us committed in a monogamous relationship. For example, how would you cope with not being able to have sex with men, as long as we are together?’

I suddenly thought back to the Moneybags, and when Mrs. Moneybags was explaining their own situation to me. I wondered if this was how it was like for them in their youth trying to cobble out their own relationship situation. Now I found myself in a similar situation.

‘I don’t know, to be honest, if it bothers me or not anymore. Since I returned home here, getting it on with men, or getting it on with anyone, actually, hasn’t been a concern of mine. I don’t socialize in town. You have been the only person I have spent any time with outside of my own immediate family. You and I know this area is not particularly friendly or open to homosexuality and displays of it, so that alone has probably helped keep a lid on me.’

‘As for the women here, I grew up with and around almost all of them – you’re the exception. If I never connected with any of them before, it is not going to happen now. The ones who aren’t married yet, aren’t really relationship material, if you get my drift.’

‘That said, alone in bed sometimes I do find myself stroking myself off thinking about my old boyfriend or the black chauffeur I told you about, or looking through a gay porn magazine I still keep hidden away…’

I paused for a few seconds before then adding, ‘…that is, those times when I haven’t been alone in bed thinking about you’. She broke a shy smile of appreciation as she thought about what I had just said, before replying.

‘I really like you, and I really appreciate how you have been completely honest and upfront with me. I agree with you, it is slim pickings around here – for men and for women – and neither of us have anyone else competing for our attention, so let’s see if we can make this work between us. I’d rather try and fail, than possibly lose someone I would later regret not trying and losing.’

She then added, ‘As long as you are loyal to me and do not sleep around with anyone else, man or woman, then I don’t have a real problem if you find you need to daydream or read porn to help release any of your other urges you find you need to deal with. Just keep it to yourself in private, and out of my sight.’

‘However, if you do find yourself struggling to cope, please talk to me about it first. I don’t want you to be hurting inside. And if you find you are going to stray with someone else, at least give me respect to tell me up front first so we can mutually and amicably end our relationship. Okay?’

I smiled back, this I could live with. ‘Okay, let’s give this a go.’

Perhaps to seal our agreement, she then leaned over to kiss me, but I stopped her and put my hand up to her lips. ‘No, not now. Explaining this all has been heavy for both of us. Let’s stop now and just go home right now, our separate ways, and sleep on it. That’ll give you one last chance to back out, and if you decide not to – then tomorrow or then next time we see each other, you and I begin with a new fresh day.

Two days later she rode up our lane. I saw her coming and waited for her to stop her bicycle in front of me. She smiled at me as she leaned it up against the fence.

‘Good morning, N!’ I said to her, while she replied ‘Good morning!’ as she put her arms around me and we kissed. Some months later, she moved in with me and we were married in small ceremony on our farm.

* * * * * * *

In early 2013 an appointment related to our farm found me needing to go to the same big city where I had done my sex work, the first time I had returned there since leaving those days behind me.

Before I made my trip, I sat down with my wife N to discuss my upcoming trip, as she knew the significance of the location. I told her that while I was there, I wanted, for my own curiosity sake, search out all that had happened over the years, to see if I could track down any of those I had been intimate with – first and foremost, Mistress R. I was simply curious to find out if she was still in business or what she had gotten up to since. Nothing more.

Finding myself now back in my old city of sexual sin, it felt strange. Much of it seemed familiar although I now felt I did not fit in the surroundings I now found myself back in.

I asked around the same daytime haunts that we had frequented, in the hopes that Mistress R still resided or worked in the area and still patronized them. When I had earlier phoned the previous numbers I knew, or went by her studio office, she was no longer answering nor there. I had success at the same coffee shop from that rainy day when Mistress R first made her offer to me. The manager working there, knew her and I managed to get a new phone number. Within half an hour, we were catching up on each other’s past dozen years.

As she explained to me, five years after I had left her, Mistress R – or, rather, now just R – had gotten spooked when her studio office got raided. She was unsure who ratted her out, but while she managed to talk herself out of anything serious, she decided right then and there it was time to quit that line of business. She always meant to do it ‘for fun’ as well as keep others safe, but over the years it had gotten bigger than she had anticipated – and now she felt vulnerable and it was time to move on.

She admitted she could understand now why I needed to leave when I did, because my gut was telling me it was the right time. Hers, too, had told her the same thing.

She sold off her office space, her partner shares in the night club, and buried herself out of sight in her daytime work. In time she met a woman whom she married a few days after gay marriage was made legal in our country.

I then asked her if she had any news or knowledge about the others.

Mr. EU and Lady M she had lost contact when she closed down, while she still bumped into Miss F through their mutual day jobs. Miss F was still ‘Miss’, still searching for her man. She had continued to ask about me in the months after I had quit, but with Mistress R unaware what had happened to me, after a while she stopped asking.

But while fate may have been sad to Miss F, as for the Moneybags, their years since those days had been more tragic: Mrs. Moneybags became suddenly ill and passed away the year (2006) after Mistress R had wrapped up her business affairs while Mr. Moneybags, now alone, then sold their mansion and his shares in their business before moving overseas – R had heard no other news since then about him, or whether he too was still alive. (I since found through recent online searches both Mr. EU and Mr. Moneybags have also passed on).

As for my old boyfriend T, she had lost contact with him a couple years after I had left, when he too moved overseas, to Asia, marrying a local woman he met and settling down there. They had written for a while until one day the letters from him just stopped.

We clinked our wine glasses and toasted them all. ‘Has it really been that long ago?’ one of us asked as we talked for hours about those days, which had seemed a haze for me in the years that follwoed, was all now vivid again.

Then at some point during our time catching up, one of us asked the other: ‘do you miss or regret those days?’

Our mutual consensus was that it had been an interesting, fun experience, but a crazy wild ride that neither of us would likely repeat if we were re-living our lives. Perhaps both of us had been naïve at the time to the dangers we may have put ourselves in.

I told her that, if anything, if I were back in my youth now but reliving those days, I would probably have explored doing porn instead of prostitution (we did not have easy acces to digital media back in those days) – while she said that she had enjoyed and still sometimes missed her dominatrix side, but she would not do the madam aspects. She said she was surprised she managed to stay out of attention and out of trouble with the authorities (or organized crime) for as long as she had.

When it was time for us to go our separate ways, we made promises to try stay in contact – but the distance between our homes as well as our life situations so far has made that our last meeting.

When I got home a couple days later, with my memories now revitalized from my meeting with R, I talked to N again about those days as well as convey what all I had learned since from R. At that time I decided to write down my recollections so I would not forget them again, as it was a remarkable experience.

Perhaps one day, I thought to myself, I would share my three years of sexual sin with a wider audience – although some details obviously cleaned to preserve mine and others’ privacy and discretion.

My writings transcribed here which I have shared with you, are the product of those notes… my adventures as a prettyboy whore.

END / ENDE / FIN

To my surprise, two women also paid for dances with me. One of them was a heavyset yet still very pretty goth woman all decked out in a tight PVC dress. She seemed recognizable from the usual people who I saw frequented there, and over top of the music and crowd noise she told me how much she liked my appearance and stuff like that.

The other woman, I found much more interesting. She too was on the chubby side as well but had an alluring hourglass figure accented by her hips and ample bust. Her face was round with doe-like eyes, and her golden blonde hair was parted on one side and went down to her chin in a long bob cut. She wore a white t-shirt, black leather jacket, spandex skirt, and knee boots. She seemed a little shy and unsure of herself, as if she were out of place, when she introduced herself to me as AB.

We danced a couple songs together before my attention was taken elsewhere when her time with me ended.

A couple hours later in the early hours of the morning night, when I had finished my work stint, I found myself at the end of the bar having a drink. I spotted AB around twenty feet away, seemingly alone and periodically looking over at me. When our eyes met, she’d quickly turn away. After about the fourth time playing this game, I waved at her and then motioned for her to come over to where I was.

‘Hey there! ~ ‘Hey!’ we awkwardly reacquainted ourselves. I could tell she was nervous about something, so I broke the ice.

‘I do have to ask you, not that I did not enjoy myself, but why did you want to dance with me? I’m usually the type men want, not by the pretty girls like yourself.’

She blushed, and her hesitancy in replying told me something troubled her.

‘I wanted to dance with you… because I had never danced with someone else… wearing a skirt… and heels… and umm, I wanted to see how it felt.’

She seemed embarrassed with her reply and blushed again as she continued. ‘I’m sorry, it is just that I have feelings I don’t understand and I am not sure how to deal with them.’

‘What kind of feelings?’ I asked her ~ ‘I don’t know for sure but I think I like women, sometimes. It's like I like men, a lot, but then sometimes I see another woman and I get tingly in my body and in my head’.

I smiled back to help put her at ease. ‘Hey, AB… that’s okay. Nothing wrong with those feelings, I have been there too. Story of my life’

She now seemed a lot more relaxed and began to open up to me. I told her about my own bisexuality and experiences dealing with uncontrollable, confusing feelings and arousal – especially during those early days when I was coming out to myself.

As the night neared closing time, and people began to head towards the exits, she thanked me for our talk. She then asked, ‘So, do you still like girls?’ ~ ‘Of course I do!’ I eagerly replied.

‘Sometimes I feel like pussy and sometimes I feel like cock. I just sort of ebb and flow between the two of them. Most of the time I don’t think about it, really. It’s more like someone gets me aroused and I go home with them. I think about if they have a pussy or cock later.’

AB then moved closer to me and leaned into my ear, asking ‘My pretty boy, would you like to come home with me?’

I was a little taken aback by her offer. After thinking about it, I replied affirmatively. ‘Yeah, yeah I think I’d really like that.’ I thought about how long it had been since I had gone home with someone from a bar and not being the product of solicited sex. I wanted pick-up sex tonight, and not be a prostitute tonight. Looking back now, I do remember I really liked how she called me ‘pretty boy’; she may have won me over just by saying those two words.

‘AB, before we leave, can I ask you something? How much did you pay for your dances with me?’

When she told me, I felt a pang go through me – from how this sexually confused girl was willing to spend money to figure out what her mind was telling her.

‘Hold on, I’ll be right back.’

I then made my way over to where Mistress R had been sitting all night. She could tell from my expression that I was upset.

‘What’s wrong, you okay?’ ~ ‘That blond girl over there, who danced with me, I want you to give her money back!’ I then explained to Mistress R all what AB had confessed to me. ‘I cannot let some curious and scared bisexual, just how I was once, pay for her own curiosity. If you don’t pay her back, I will myself!’

While I didn’t doubt Mistress R agreed with me, her reluctance to act immediately on my request caused me to storm off, back to AB who was still waiting patiently for me to return.

‘Everything okay?’ she asked. I had cash enough on me, stuffed down inside my corset, which I had fished out and forced into her hand.

‘Here you go, our dances together are on the house,’ I said as I took her hand and made for the door. As I left, I looked back and scowled at Mistress R. After stopping by the coat check, we made our way out into the street to hail a taxi. And I did not let go of her hand until we reached her apartment some fifteen minutes later.

Once inside her apartment, AB and I rushed for the nearest couch and began kissing. Half an hour or so later when it felt ready to move on to more intimacy, she then stood up. ‘Wait out here for five minutes before coming into my bedroom, okay?’ before she then went off to her room ~ ‘Okay, sure’

I then sat on the couch, looking at a wall clock slowly ticking away. At some point, she called from her room, ‘I’m ready!’

I walked into her room, to find her lying naked on her bed, with her hands handcuffed to her bed’s backboard. I cannot remember how she worded it, but she then said something along the lines of ‘fuck me please, take me, do what you want with me.’ 

I began to undress, extracting myself from the confines of my corset and tight skirt. After removing my latex and fishnet top, all that remained was my stockings and heels – but she then asked me, ‘No, leave some of that on please!’

I acceded, on a whim putting my corset back on. I then crawled on to her bed and buried my face between her legs. As I ate her delicious pussy, she writhed and kicked her legs about in pleasure and began rhythmically moaning. This girl was a loud one and I sensed from her sounds that it had been a while since she had last gotten laid.

When I was finished working her slit, I moved myself up on to her and sucked her nipples. Both of them were pierced with rings, so I played my tongue around them, licking and moving them around and sometimes gently tugging on them.

She then used her legs to push and indicate she wanted me on her, inside her. I sat back and looked at her as she laid there with her arms tied back. She smiled at me expectantly. I decided, however, she really needed some affection and her arms around me, I wanted her arms around me and mine around her, to feel loved, so I took the handcuff key on her bed table and unlocked her.

* * * * * * *

The next time I saw AB again, it was one evening at the club some months later. She had a woman friend with her, and when AB and I made eye contact, she smiled at me and then nodded at her friend. I smiled back at her in approval, hoping that some of what I had told her had helped her make her first steps.

But, however happy I was for AB, my encounter with her had also made me begin to question my activities with Mistress R. While her and I never brought it up, we both knew my outburst about AB’s dance had created a rift between us.

Some weekends when I did not have one of my clients arranged for a Friday or Saturday evening or night session, I would invariably find myself at the underground goth club we all called home. Some of those instances I would fill in as one of the go-go dancers there, usually this would be when Mistress R was hosting some special event there.

Positioned around the club’s main dance floor were risers on top of the soundsystem speakers, where club patrons would jostle for space to dance and show themselves off. On each corner were iron cages, four in total, in which a dancer, or a pair of dancers, could be locked inside. These cages would be manned by professional dancers on the club’s payroll – or someone from Mistress R’s coterie, when the subject matter inside them required a more risqué or perverted nature.

Twice I did duty inside the dance cage. The first time I was just dressed my ‘normal’ self. To keep my stamina and energy going for the two to three hours I would spend in constant motion, I required a few drinks to get my blood sugar pumped up as well as drunk enough to weaken my inhibitions in a public environment as this. I recall enjoying the sensation of being inside the cage, the sensation of knowing you were the attention of unknown number of watchers, and the helplessness of being unable to have refuge from those times when people on the outside would put their hands through the bars and try touch and grope me. Sometimes I let them, sometimes I did not.

My second dance session inside a cage was for a club-wide fetish night special event. Patrons gaining entry, beyond prior personal invitation issued, had to adhere to a strict fetish dress code. The evening vibe oozed raw sex, sensuality, kink, and perversion. For this event, I was paired up with a woman dancer and both of us were naked except for matching latex masks, stay-up black stockings, and heels. I have no clue who she was, never got her name and never saw her face, but we quickly established great chemistry between us.

Two people inside the cage made for cramped space, and we could only stand up with one of us positioned in front of the other. As we took in the energy of the music and the crowd around us, our arms wrapped and writhed and slithered around each other, as she would move her hands around my exposed, hard penis and my body, as I then worked her small but firm breasts and occasionally fingered her vagina when she was positioned in front of me. When she was behind me, she would reach around and make sure I was hard – sometimes stroking me off to the point of dripping my load. At one point we somehow managed to get one of her legs up enough that I could get some of myself inside her from behind, before quickly slipping out. A few times my attention on her would be broken and I would then look around us, and notice the curious and enthralled faces looking up at us as we danced our mutual, spontaneous sex show. When we were finally released from our dance jail, both of us were soaked from each other’s sweat and body fluids, as well as exhausted from being forced on our feet for so long.

From her movements and confidence, I felt that she probably had experience as a stripper, while I myself felt both shy at my exposure in public – but also aroused, too, as this would have been the greatest number of random people to see me naked or in a sexual situation at any given time.


* * * * * * *

The closest I ever experienced during my time involved with Mistress R with actually being whored out, as in not having a say regarding the clients, were two instances when I filled in as a paid dancer at the club.

Most Saturdays at the club, in the invitation-only level overlooking down on to the main dancefloor levels, Mistress R would have a few of her crew working as paid, private dancers who could be bought for more intimate one-on-one contact – either for single songs, or for set periods of time. The private area had its own small dance floor as well as another two iron cages for dancers to be put on show. Clients would be handed various coloured tokens, that indicated number of dances or time length, which they would then present to their desired dancer.

Mistress R insisted on some strict rules: we were not allowed to remove our clothing and we were not allowed to talk at all to our partner, even if they asked us something. All we could do was smile, nod, or convey our answer from our motion, actions, or with our eyes. Lastly, we were not allowed to kiss on the lips.

Often these particular dancers were new to Mistress R’s employ and new to the business, often being shown off for potential future sex work to clients in attendance. If she was unsure whether a particular boy or girl had what it took mentally and emotionally for sex work, she would try them out as these dancers to see how they could cope being groped or whatever light physical contact was allowed.

In my own case, I just offered to help fill in a vacant spot a couple of times when she was short for private dancers. Many of the details between those two nights in question are now blurred together. I think overall I danced with around nine partners, but only four of them – two bad and two good experiences – do I still have any memories. All but two I danced with, were males. For selection Mistress R would have an assortment of feminine women, firm men, and in between and out in left field, which is where I fit in.

For this particular role, Mistress R asked me to dress as slutty and sissy-boy feminine as possible. I believe the photographs of me in my ‘sissy slut boy action’ album were taken during those two nights. Much like my experience inside the main dancefloor cage, I expected I would be subject to a lot of groping – which is why I wore my shortest, tightest skirt, to accent my firm tight ass.

Two guys in particular were absolute perverts trying to push boundaries beyond what were permitted – and one of them actually scared me a lot. All the while we slow danced together, he was grabbing my ass and kneading it hard with his hands, hard enough it began to hurt. At the same time, he was telling me all about how I was a little faggot boy and if he saw me outside when I left at the end of the night, he was going to drag me off to the alley, rape my ass until I bled and beat me up like I was his bitch, and stuff like that.

Now, from the smell of his breath I knew he had been drinking a lot, so part of me wondered if this was just him talking up his fantasies or that he thought I perhaps liked and got aroused hearing that kind of aggressive talk – but there was just enough nastiness edge and anger in voice to make me wonder too if his threats were actually serious. When I did leave that night, I never did see him waiting for me, but I still made sure I was in the close company of Mistress R and her majordomo M, whom I stayed real close to, he wondering why I was holding on to his arm until we got to her car.

However, there was one guy on my first night who was the complete opposite.

He was around ten or fifteen years older than me, and when he walked up to me with his token in hand (for an hour), I would never have guessed from his appearance that he in any way held any sort of attraction to men. I think he was Italian or Spanish, judging from his look and accent – and was stylishly dressed in a designer black suit. He was outstandingly gorgeous, exuded masculine style, strength, and importance. I could sense he was ‘somebody’, and from overhearing later talk, and the crowd he kept around him, my suspicions felt confirmed.

He treated me with sincere respect and dignity as we held our bodies close to each other. My heart fluttered whenever he touched my lower back or ass, and I did not want to let him go. When we took breaks between dances, he would put his arm around my waist as we stood at the bar, him talking to others, and no one batting an eye that this guy had his arm around another man, dressed in a skirt, corset, and black lipstick. Once, I remember he had his hand resting flat on the lower part of my corseted back, and I gently pushed it down slowly but firmly to my ass and gave his hand a squeeze, trying to indicate my own attraction and desire for him.

During one dance, we could feel our bulges pushing into each other’s. I had my head on his shoulder, purring away so happy and content as he gently kissed and tongued my ear. I kept hoping that Mistress R would tell me at the end of the night that he wanted to hire me for more than just dancing. I wanted him so very badly. I would have gleefully slept with him, sucked him, offered my ass over to him, whatever it was he wanted from me, I would have given him in a heart-beat… but to my disappointment the request never came. I thought about breaking my silence but I suppose my professionalism got the better of me. At the time I felt if it was meant to happen, it would happen – but looking back days, months, years, later, I wish now I had spoken up. Even today, years later, thinking about him makes me hard (such as I write now) and I often stroke off in bed or in the shower thinking about him.

A few stays at the mansion found Mr. Moneybags away on business trips overseas, and therefore Mrs. Moneybags having me all to herself for the weekend. We took advantage of this extended time spent together to experiment and play out some of her fantasies – as well as enjoy some private social time together.

One weekend I played the part of her sex slave. I stripped down completely naked and was chained by my neck, locked so I could not remove it, to her bedpost from Friday evening until Sunday morning when I packed up and left for home – only being unchained when she would lead me on my hands and knees crawling to the ensuite washroom in her bedroom to relieve myself. Otherwise, with around ten feet of chain and my dog collar limiting my movements, I waited in her bedroom to show up throughout the day as she desired instant sex. Which was a lot, and more than I could physically keep up with. Her sex drive like many weekends was incredible to witness and experience as she fucked me dry and limp.

Often she and I would dress up in the evening and go out for dinner dates far away from her known establishments where she would be unknown and not recognized, so that we could express some intimacy in public and she could show off being seen with such a young conquest. While our obvious age difference would have normally suggested that I was perhaps her son, her more than revealing manner of dress, such as a low-cut or off-shoulder dress displaying her ample cleavage went a long way to negate any indication of a mother-son paring – and conveyed a more sensual and perverted twist to our relationship, which no doubt left some observers wondering what exactly was the true nature between us.

The most enjoyable experience I had with Mrs. Moneybags was when I took her out one night to the goth alternative club where Mistress R and the rest of us held court. She was intrigued to see first-hand the fetish scene world in which Mistress R and I called home, to see me behave in my natural element as well as see first-hand how other couples expressed their perverted selves in a public domain.

Obviously she was concerned, rightfully so, that she would be recognised by the more artistic souls in our community, some who no doubt had been to her gallery and art shows – but with the assistance and encouragement of Mistress R, we costumed her up enough to hide her identity.

We took her over to Mistress R’s studio so we could go to work transforming her. I dressed her up in a long lace, see-though dress borrowed from Mistress R’s wardrobe, under which she wore some latex stockings and latex underwear which we had bought for her earlier in the day. I wanted to see if I could push her comfort boundaries as well as let her simply let loose, so I convinced her to expose her buxom tits and go topless with nothing but electrical tape X’s stuck over her nipples and the shroud of the lace cascading over her bust. I loaned her my corset to help accent her figure and draw even more attention to her 36Ds.

I then sat her down and began to make up her face. I could tell from her breathing as I worked on her, that she was both uncertain of herself as well as aroused and excited by the unknown environment for our evening. Using old black and white movie vamps from the 1920’s as inspiration, I pinned up and back her steel grey wavy hair before I began to cake her face porcelain white with powder make-up. Mistress R then took over and applied some eyeliner and gave her a gothic Egyptian cleopatra look around her eyes, before then giving her some black lipstick on her lips. To finish it all off, I then lowered my black bobbed wig on her, before adjusting it slightly and then handing her a mirror. We did a great job hiding both her identity as well as her age, and her immediate reaction was a surprised, yet sensual, “oh my!”

However we wouldn’t let her look at herself in a full-length mirror, as we wanted to put in her head some mystery how she may have perceived she appeared. We told her, rather, let the looks you get around you, give you an idea how you look. We also did not want her to have regrets with her appearance and back out if she knew how exposed her body was from her normal comfort level. Secretly I wanted to show her off, as she did have a great body for an older woman. As Mistress R later expressed to me, ‘this is something she needs to do for her own sexual confidence sake’.

The three of us then piled into Mistress R’s Mercedes and made our way out to the club. Much what happened there I have forgotten from our mutual drunken stupor, except as soon as we arrived and she settled into her new surroundings, both of us found us aroused and physically drawn and close together all night, holding hands, dancing, arms around each other, and kissing when opportunity presented itself. I wanted her, badly.

We decided to leave an hour before closing, so we could get Mistress R’s limousine drop us off at the mansion before returning to retrieve Mistress R at the end of the night. Heading through downtown, we found ourselves passing by her art gallery – so impulsively I told Mistress R’s chauffer M to pull over and stop in front of it.

‘What are we doing here?’ she turned surprised, asking me. ‘We – are going to fuck – right now – right here – in the car – in front of your place’. She then cast a glance over at M in the driver’s seat, wondering about him and our privacy. I brushed him off, replying loud enough for M to overhear me, ‘M and I have been intimate, so everything he sees or hears here, stays here – I can fuck in front of him, and so can you.’ Later I did wonder if she was thinking M would be joining us as well, but even if he did, there was just not enough room in the back of the car for a third participant.

I positioned her around on the back seat so she was facing out sideways and looking through the smoked glass windows of the car at her art gallery, and took her from behind. While I fucked her, I held her head firm with both of my hands, forcing her to stare at her gallery across from our view. I whispered in her ear, ‘now whenever you look out of your gallery window, you’re going to think back to this time we fucked right here’. Both of us were absolutely horny and it only took a few minutes before we both came. I am sure anyone walking by the car, while not able to see inside, would have heard her loud moans as she orgasmed.

As soon as our breathing calmed down and we recollected ourselves, M then drove off to take us back the mansion.

We continued driving through downtown with the bright lights and glare of the night city flashing all around us. I then moved myself so I could lift up her legs, spread her, and eat her soaking pussy all the while Mrs. Moneybags could watch the familiar world around her pass by unaware to those around us as she soon came again.

The call from the Moneybags came four days later. Mistress R telephoned me at home late on a Tuesday night.

‘You made an impression with both of them and they liked what they saw. How soon do you think you could get out here for a session with them? It would be for the whole weekend and you’ll be staying with them the whole time. At their home – and, in their beds.’

Mistress R and I discussed my schedule as it related to my day job as well as upcoming sessions with my other clients and we soon figured out the earliest opportunity.

She then added, with some uncertainty in her voice how I would react, ‘They have already asked T, if he would join you as well, when you make your debut with them… are you okay with this? Mrs. Moneybags has a thing for watching gay men get it off together, so she thinks you and T paired up together would fit that bill nicely.’

Mistress R then added some details, new to me. ‘T has already done stuff like this before, so it all depends on if you are comfortable with performing with him, for them…’

T had never told anything substantial about his own time while working for Mistress R, nor what other men he had slept with while on the job, but once the momentary thoughts of being taken aback hearing this tantalizing new detail had passed, I agreed. With how distant and disinterested our relationship had now become, if anything else it gave me one last round of sexual action with him – and ultimately, this voyeur show for the Moneybags did end up being our last fuck together.

* * * * * * *

A couple weekends later, on my arrival in the city, Mistress R picked me up at the downtown station. We returned to her studio office where T was already there waiting and packed for our weekend. The three of us sat down over some drinks as we talked about what was ahead for me and what I should expect. Admittedly it was strange for me to be working alongside anyone else, let alone my soon to be former boyfriend T, but the excitement soon got the better of me and made me forget about any reservations or unease I may have had.

As he and Mistress R explained to me, when T had serviced them in the past, he would usually spend one night alone with Mr. Moneybags, and then the following night alone with Mrs. Moneybags, although since both of them enjoyed voyeurism, sometimes one would watch their other-half getting fucked. Mr. Moneybags really enjoyed seeing his wife with others, but she did not seem to share the same arousal watching him getting pleasured. She did enjoy seeing other men together, just not with her husband.

The three of us were unsure how the weekend would play out with both T and me there at once, so we decided we would just react to whatever transpired at the moment and pair off and play it all by ear. Mistress R figured, based on her behavior at the previous cocktail meeting, that Mrs Moneybags would be wanting to get her claws on me at first opportunity. But then she also really loved her time spent with T, so perhaps she may want to get one last session of lovemaking in with him, since he had left the business so to speak.

T then interrupted Mistress R, asking skeptically ‘Talk about this voyeur session they want.’

‘Yes, that…’ – bringing us up to speed, Mistress R explained that they ‘have asked to watch both of you perform in front of them, as in have sex for them.’

I looked over at T and said, ‘well I suppose I will take my usual bottom station, then?’ but then Mistress R interrupted, looked at T and then over at me. ‘I think she will want you both to take turns on each other.’

I had never fucked my boyfriend in his ass before – I had only ever topped another guy once, in what was my first gay experience. This would be serious uncharted and psychologically uncomfortable territory for the both of us. When I asked him, ‘Are you okay with this?’ I could tell he was not, and so too could Mistress R.

The three of us then sat in an uncomfortable silence for around a minute, thinking this out collectively in our heads. Mistress R then piped up, ‘how about you guys use a double ended dildo on each other? The sight of you two going at it with your asses slapping each other might actually be more visually erotic and interesting than simply doing anal on each other’.

I looked over at T, saying ‘of course I’m good with that’. Realizing this was probably the best of a bad situation for him, T then grudgingly agreed, ‘I suppose so’.

* * * * * * *

The evening of our session, the three of us piled into the Mistress’ black Mercedes as she drove us over to their house. It was a nasty, cold and rainy night, and as we drove along I would peer out the windows trying to figure out where we were headed, but this was a part of the city on the outskirts where I had never venture to during my previous visits.

At some point I became bored with the blackness of the rain and night, and so my attention shifted over to T, sitting next to me in the backseat, silently in thought and looking out the window just as I had been doing.  

My boyfriend had decided to accent his shapely, muscular physique by wearing some pvc-leather pants but was otherwise topless – his leather jacket would come off once we had arrived and gotten ourselves out of the rain. Besides, it was not like we would be keeping our clothes on for long.

Since Mrs. Moneybags had liked seeing me in drag, I decided to dress up feminine if nothing else for my arrival at their home. I wore my favourite short, pleated black skirt with a white shirt and black tie. For the same reasons of us soon becoming undressed on arrival, I did not bother covering my legs and I just wore some doc marten boots. To help play up Mrs. Moneybag’s apparent interest, I had made up my face with black lipstick and some face powder and Mistress R had drawn some eyeliner on for me. My now short hair I had simply gelled and slicked back. As a last girlish touch, I had opted to wear a hoop earring in my nose.

After what seemed like a longer than anticipated journey, all in silence as the three of us kept our thoughts to ourselves, the Mistress’ car turned up a long dark driveway and through a pair of stone pillars and an open gate, which then closed after us. The Mercedes pulled up in front of the house, but in the rain we made a quick run for the secondary side entrance. As I went through the welcome, open door rescuing us from the torrents of rain, I looked back at the Mistress’ automobile, and spotted a servant or some sort of staff hauling our two suitcases out of the car, before Mistress R then drove away.

T and I were greeted by someone who appeared to be their butler and T exchanged some small talk with him, while I now took in my location and became fully aware of the size and scale of their mansion they called home. It was very soon clear to me that this very stylish, old house was easily the most extravagant home I had ever been invited to. T then got my attention and took my hand. ‘Come with me, I’ll show you to the sitting room where we can store our stuff as well as change’.

After T and I had re-united with our suitcases and removed our wet coats, he explained the general rundown of the place and where to find things.

‘Like I said before, they are a really nice couple and once you and them begin to feel comfortable, it becomes very easy to take a liking to this place and feel at home, so to speak. Just relax.’

The house was massive, even though only the two of them lived there full time. T showed me where the main kitchen and pantry was, where I could get something rustled up to eat on request – they had their own in-house chef. I was amazed by this, and asked T: ‘How many people live here? How many staff do they have?’ and other such details I want to know. Along with the chef, and the butler, they had two or three others that were basically part-time assistants who maintained the grounds, cleaning, and other general labor duties – probably one of those who brought our suitcases inside.

T and I waited in the sitting room, enjoying a drink which had been brought to us, and having seen no sign yet of the husband and wife of the house.

We were then interrupted by the butler: ‘Everything is all set, when you are ready for show time, we’ll make our way down to the theatre room’.

Hearing this, I was like ‘theatre?’ – and T explained that most of the house was actually vacant and empty, and part of the basement had been covered into an arts and performance area. That was where we would put on our show.

T then stood up, looked at me, and said, ‘Well, let’s get this started…’ as he began to undress in front of me.

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?

After I had agreed to become a prostitute for Mistress R, she explained to me what would happen next. Mistress R had devised an initiation process for all her pleasure girls and pleasure boys, as she called her workers. I would first have to complete a sex ritual which she had devised, and then I would be presented to a select group of her clients in what she called ‘the meat market’ to be shopped out for prospective business.

* * * * * * *

‘Have you ever heard of apostolic succession?’ she questioned me – ‘No, I haven’t’, I replied, confused. ’What the fuck is that?’ – about which she then explained to me:

‘Apostolic succession is a tradition in some Christian churches, where there is an unbroken legacy or line of continuation of ordination back through the ages – and all priests and bishops can in theory trace their ordination back to the start.’

‘When I started my “coterie” (that is what she called her operation), I thought it would be interesting, as well as create some blasphemous notoriety, to create a similar process or ritual, where all my new workers were initiated into my service by those who came before them.’

‘Because almost all my clients come from outside participation in our goth scene, I can very easily play up that dark, sinister element and present myself to them as some sort of succubus selling sin to them, making a carnal deal with a she-devil. I make it known to most of them that my servants are bound to me by a sex ritual, the one you will soon undertake’.

‘Everyone who starts work for me, I initiate them into my service by making them have sex with one woman and one man who already works under me. While I do this mostly for my own amusement and intrigue, I have found over time it actually does serve a purpose – as I require all my boys and girls to be willing and ready to sleep with both boys and girls, so this helps weed out any ‘problem cases’ one may have with performing homosexual acts. Anyway, once they fulfill these requirements of initiation, then I say they are bound to my service’.

‘For my new boys, they must kiss another boy for five minutes, suck cock for five minutes, and then take cock in their ass for five minutes. They then must kiss one of my girls for five minutes, eat pussy for five minutes, and then fuck them for five minutes.’

‘Oh really?’ I exclaimed, partially confused by what all she had just said, and partially intrigued by what I had to look forward to. ‘So what do your girls have to do?’ I asked her. ‘Pretty much the same; kiss, suck cock, ass fucked, and eat pussy – all for five minutes at a time.’

Thinking about my own upcoming initiation, I asked ‘so who does all this with me?’

‘Oh, you can choose, or I can arrange for you - all those under my employ are expected to fulfill their part in the initiation process when asked and required. In time you yourself may be called on to play your part as well’, she said with a smile.

I then glanced over at the open hallway area, where her muscular, gorgeous black bouncer chauffeur, was positioned at his station watching the entrance area to her studio office.

‘So… what about him?’

She seemed surprised at my suggestion. ‘He is pretty big, you know, and I am not talking about his frame – but yes, if you think you can take him, by all means. He has gone through the same ritual.’

Naively not realising fully what I was getting myself into, ‘yeah him, I want him pretty bad.’

Mistress R called over to her bouncer, named M, ‘Could you come here? My new boy here tells me he’d like you to initiate him’. M walked over towards us, breaking into a big smile, ‘yes ma’am!’

I wasn’t expecting that it would happen right then and there, but as I found out later from her, Mistress R took advantage of the spontaneity of the moment to catch me off guard to see how I reacted and responded under pressure and whether I could perform on a whim.

‘You two, follow me…’

M ushered me to follow Mistress R who led us into one of the private rooms across the hallway from her main office area.

The room was mostly empty, expect for a couple of chairs. M walked to one of the walls to retrieve a rolled up tamami mat, which he then unrolled and laid out on the floor.

Mistress R then turned to me, ordering ‘strip down’. Both M and I undressed, and when I found myself completely naked, I turned to face a massive 7 or 8 inch cock. I felt my insides flinch, as I had never seen a cock so big.

I looked at Mistress R, who looked at me and then looked at his cock. ‘Begin’.

I got down on my knees and positioned my mouth in front of him. I touched the tip of his penis with a finger, it was both hard and smooth – and then took it into my mouth, wide open. The whole time I worked my tongue and lips around him, I was wondering to myself just how the hell on earth was I going to fit him in my ass?

A few minutes into the act, I took both of his hands, and guided them to my head. He knew what I was trying to indicate, as he grabbed my head and he began to push my head forcefully back and forth, and forcing my throat deeper around his hard manhood. I looked over sideways at Mistress R as she sat watching and smiling with intense curiosity. I could feel his penis-head pushing farther and farther into my throat, choking and gagging me, forcing out audible, rhythmic choking grunts as he thrusted.

When it was becoming too intense for me, I instinctively tried to push him away from me when I could not breath, but Mistress R shouted at me, ‘Oh no, keep your hands down you little slut! This is what you wanted, now take it.’ I then felt his pre-cum seeping down the back of my throat, and I began to gargle it back out from reflex. The whole time, the cock-slut I was, absolutely loved what was happening to me.

When Mistress R told us that we had done enough, M pulled himself out of my mouth, and then grabbed me roughly to position myself on my knees, to take my ass as his own. He pushed my back down so my face was down on the ground – and he held my arms back behind me. I felt cold liquid on my asshole, as Mistress R squirted some lubricant on me. I then felt his thumb work it around and force its way into my opening to lube me up.

M then asked me, ‘Are you ready?’ – my face now down on the ground, I simply moved my knees to spread my butt checks wide, inviting him inside me – as I braced for the unknown pain I knew was going to hit me.

He entered me fast and hard. It felt like my ass was being ripped apart by a vice, or that I had been impaled on a stake like from some old vampire woodcut of Dracula and his victims.

My ass hurt – my muscles there burned, like I was being torn apart. I began to scream, over and over ‘OHH FUCK!’ and ‘OWW!” because it was all I could do. Mistress R later told me that it sounded like I had realised I had made a serious mistake. As M pumped me, for what felt like an eternity, my body began to feel numb like it was paralysed. The pain was intense and hurt brutally, and then I realised I was crying in pain. It was all I could do while I waited out the pain, I cried and screamed like a little sissy.

Finally the required time had passed and M pulled out as quickly as he had entered me. The pain my asshole had endured stopped and I could feel my opening shrink back down to normal, but my inside still felt numb. I crumpled on the ground and went into fetal position, my face and hair soaked from my tears. Both Mistress R and M bent down over me, now caressing me as I recovered and regained my composure.

I sat up and wrapped my arms around my knees. M then humbly apologized, ‘I’m sorry I hurt you’ – ‘No, it is okay, to be honest.’ We then kissed each other on the lips, and I told him ‘I secretly had been wanting you, so I only have my selfishness and stupidity to blame’. We smiled at each other and M walked off to collect his clothes while Mistress R wrapped a towel around me and hugged me.

She then whispered in my ear, ‘excuse the pun, but then hard part is now over. Maybe next time you visit me, we will arrange for the second part then’.

Right away in our relationship Mistress R had made it absolutely clear to me the sexual boundaries between us with two rules she insisted.

She explained to me how she was a lesbian when it came to physical sex, so we would never have intercourse together – or as she explicitly spelled it out to me: ‘your penis will never touch or penetrate my vagina’. That was the first barrier; the second was that I would never see her naked body. If I ever performed oral on her, I would be blindfolded and completely tied down, so I could not try to touch her private areas with my hands.

Despite the physical sexual barriers built between us, we shared deep feelings for each other and we would still find and build a lot of intimacy between us. For the approximately three years I knew  Mistress R intimately, she was the closest woman I could describe as anything like a ‘girlfriend’ at that time – except we never used ‘girl-/boy-friend’ terms to describe us, nor publicly referred to ourselves outside of anything platonic. Once, I attended a wedding as her date – but she passed me off, for anyone who asked who I was, as her younger brother. I do know we drew some curious eyes that day, because we would still sneak some hand-holding, I think because she was trying to mischievously disturb those observers too curious for their own good, as us being siblings too close for accepted comfort.

No, we saw ourselves best described as ‘lovers’. She had female sexual partners, whom I never saw although I had strong suspicions who they may have been, but when I stayed with her, either at her apartment or her studio, we shared the same bed. Underneath the sheets we hugged, we kissed, and although we never consummated our relationship with traditional intercourse, we had sex together countless times as she fucked my ass with her strap-on and other sexual tools. My role in her life was that of her primary male company, when she required such both publicly as well as what I could provide to her emotionally in private.

When I had asked Mistress R what she, herself, wanted from me, she explained that despite being surrounded by constant sex around her due to her night work, like any human being she still required private intimacy which that ‘harsh’ or ‘hard’ aspect could not provide for her. Despite being a lesbian, she still enjoyed being around pretty boys, like myself, and the company and intimacy we could provide her. Being a Mistress was her public persona, but behind closed doors at home she was just as human and vulnerable like anyone else with the same emotional needs. When one night she had privately lamented her loneliness and need for intimate friendship, to my boyfriend T and his woman D, it was them who thought I may be a suitable candidate to provide her with some comfort and tenderness.

We had this unspoken, intuitive connection between us that we both somehow seemed to know when we were acting in ‘mistress and slave’ roles and we were ‘lovers and equals’, and sensed when it flowed back and forth switching between the both. Within the limits that were possible in our unique relationship, I felt I truly loved her – as I loved how she made me feel sexually, physically, and emotionally at the time. She taught me aspects about sex, pleasure, enjoying life, and pushing one’s limits, which I would never have experienced otherwise. She helped me feel comfortable with accepting my bisexuality and my androgynous crossdressing as a means to explore that sexual aspect of mine.

Back in those days, ‘pegging’ was relatively unknown. The term had not yet been invented, and strap-on sex performed on men was something considered to be on the edge. She had read about it somewhere and she was curious to try it, as she liked how it would give her a new means to dominate over a submissive man. Since I was willing to give this a try, and soon found that I thoroughly enjoyed the role and position reversal, as well as the pleasure it gave me, ‘pegging’, or strap-on sex, or ‘bobbing’ (another term sometimes used back then) was something we frequently did when intimate or during our master-slave sessions between us.

Most women don’t know the physical motions for fucking with a penis, so here I taught her how she needed to thrust her hips when making penetration, instead of bouncing her body up and down like how some women seem to behave when wearing and using a strap-on.

Whether with my boyfriend, and now with her, my favourite sex position when receiving was on my back, my legs spread wide as possible or back up and around behind my head. Thankfully whenever Mistress R pegged me, she liked taking me from the front on my back, so we could look at each other and kiss while in coitus. I especially liked wearing stockings and heels, as she liked the feel of them on her whenever I would wrap my legs around her body to hold her close to me.

And, as much as I enjoyed being tied up, broken in, violated, tortured, and screaming as she fucked and whipped my ass and abused my body during our mistress-and-slave sessions, I also enjoyed those quiet days where we went out, held hands, and explored the city around us. In the months since we had first met, our relationship had become closer privately between us. When I visited and stayed with her, we shared the same bed and would kiss and cuddle at night. Those moments were just as pleasurable and exciting. We saw ourselves simply as two lovers passing by each other on the carnal road of life.

Both Mistress R and I knew full well this relationship between us was temporary, but during the time we maintained it, I absorbed and enjoyed every second of it.

* * * * * * *

One early afternoon while visiting with Mistress R, we found ourselves tucked away at a small coffeehouse in an older part of downtown. We had gone out shopping that day but were caught in a sudden rainstorm, so we decided to find shelter and wait it out. We found a cozy, private corner along the brickwork walls to call our own.

We settled into our seats, a long pillowed bench along a wall and behind a heavy wood table where we could view the comings and goings of the establishment. Mistress R, who in her daytime street clothes, looked nothing like a mistress, and everything like one of the college kids who were here around us, shifted up close to me so we could talk privately us and not be overheard.

Mistress R put her arm around me, pulled me closer, and kissed my ear. She then whispered, in a serious tone, ‘I want to ask you something’.

I responded, ‘Go ahead, ask away. There are no secrets between us’ – not wasting any time, she then dropped the bomb on me: ‘Would you ever do any sexwork for me?’

The question took me aback, I may have even appeared startled by it, because even though I had seen her night work in action around me, I never thought I would get involved in it. I had simply looked the other way whenever it came within my vicinity when at the clubs or at her studio office.

‘You mean, like a male prostitute?’ – ‘Yes. Exactly. A male prostitute.’

I sat back and collected my thoughts and questions that were now swirling inside my brain.

‘Why would I want to do that? Truthfully, it has never crossed my mind’.

I must have sounded defensive or perhaps critical, as she sat up, narrowed her eyes and chirped back at me, ‘why you ask, you little bitch?’, loud enough to make her point but not loud enough to attract the attention of those around us: ‘Seriously, look at yourself in a mirror next time before we go out… there are a lot of people who would pay good money for that tight ass and mouth of yours – let alone how you dress and act.’

‘Really?’ (although truthfully her answer did not really surprise me, I was aware of the attention I drew from the perverts out there in the scene). ‘Umm, would it change anything between you and I? – or my boyfriend T?’ I asked.

‘No, nothing with me…’ she said as she put her hand on my knee. ‘…and knowing T myself, I don’t think with him either but you would need to have that talk with him. If T were that protective of you, he would never have introduced us and shared you with me. Remember, T and D have done some work for me too in the past – so, you see the picture… and both of them have confessed to me that you are good in bed, with girls and with boys.’

‘To be honest here, cards on the table, I have to admit I am intrigued – but also a little turned off and cautious as well. I really don’t know if I could fuck just anyone that I don’t know… well, no, I probably could… if they are good looking enough, but still for my personal safety sake, physical and medical, first and foremost, I am not so sure… and are we talking men or women here or what?’

‘Both – whatever you are comfortable with. I service the needs of clients of both sexes. Sometimes couples. And everyone I take on as a client, I vet them for criminal dangers, as I have friends in important places who can help with that. All my clients are an exclusive group and I ask for regular proof of clean STD tests, stuff like that. I don’t serve to just anyone off the streets.’

Then I brought up some more of my personal reservations about her line of work, but despite all the mental obstacles and genuine concerns I kept throwing up to roadblock her enquiries, she gave what sounded like reasonable and reinforcing answers – while the slave buried deep inside me was secretly enthralled and aroused by the thought of being used as a sexual play-thing.

‘‘Look Mistress, despite what you say about money, the fact is I really don’t need it and I don’t want it. My day job looks after me quite well for my needs. And frankly I feel really uncomfortable and uncertain with the monetary aspect. But… I would be lying if I don’t find the idea of being used as someone’s fuck-meat really, really intriguing, arousing, and enticing… because there is nothing more I love doing more than fucking or getting fucked. I love sex and I cannot get enough. When I am home alone, I am always horny and getting myself off. So yeah, having that kind of access to willing and eager partners is something I find hard to outright ignore or turn down…’ 

We then looked at each other, awkwardly, for the next minute or so, as we waited in the impasse for the other one to say something further. She may have even been wondering if she had crossed the line with me.

I spoke first when an idea came to my head and I then countered her original question with an offer of my own: ‘Okay, hear me out… how about this:’

‘First… give me absolute control and say over who I service, and when I service them – this way my safety concerns are satisfied and I can work this around my day life. After all, I don’t live here, so logistics dictate that I could only do this once every few weekends when I travel here to visit you and T’.

‘Second… offer me to repeat clients, so I get to know them and feel safe and comfortable with them. I am open for anyone, men or women or whatever – except, one firm deal-breaker with men is they must be circumcised, as I don’t suck or sleep with foreskin, for hygienic reasons. A clean smooth cock is a must for me – that is something I won’t compromise’.

‘Third…’ and I was curious how this would strike her… ‘you tell me when and where and with whomever, and this slave-slut will show up, do what is asked of me, leave – and this slave-slut, being a slut and a slave, after all, will never see or hear anything at all about money… nothing. If I do this, I do this for my own self-enjoyment.’

Mistress R sat back with a perplexed look, uttering ‘Huh…?’ as she took in what I had just proposed.   
I added, ‘you do what you do at your business end, I don’t care what you make off me – honestly, go ahead and exploit me. If anything, this would make me the perfect slave for you in the absolute sense, because both of us would get to experience the sense of servitude and exploitation. I would be a slave through and through’ – although years later, away from those years, I did take delight and self-pride thinking back that I was a male prostitute… a whore… a real whore.

I then sat back and let my offer sink in, watching her eyes and her face movements to gauge a sense of what she made of all I had just said. I then looked around the coffeehouse, at the random chatter and noise of life going on around us – all obvious to our talk of carnal business going down in that corner.

When I then re-affixed my eyes on Mistress R, she rolled and bit her puckered lips in thought.

She then extended out her right hand across the table to me – not to kiss, but rather to shake and seal our agreement.

‘Okay. Agreed’.