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’.