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my adventures as a prettyboy whore
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For about two and a half to three years in my late 20s, every four weeks I would travel a few hours away to the big city where my mistress resided and worked. As soon as I packed and left home for the weekend, I would take the train there and be met at the station either by her in person, her personal assistant (who also filled the role of chauffeur), or occasionally one of her other working girls or boys in employed by her. If it was her, then we would return to her studio office by limousine and discuss our business for the weekend. Sometimes I was just there to visit with her, because as well as having a working relationship, we were also really close friends and casual lovers in a sense. We would dress up and go out the next couple of evenings drinking and dancing the night away at one of goth or alterative clubs we frequented. But if she had one of her short list clients lined up for me, then we would talk about if I felt game, and who it was and what they wanted.
My mistress made good income off me, but I simply enjoyed the opportunities and connections to explore my sexual fetishes and kinks and be able to hook up with likeminded people. So our mutual agreement was as long as all my expenses were covered while under her wing, I work ‘en gratis’ and had the freedom to choose and accept or turn down work offered. Not that I did often, as she had just four clients who had access to request me – and all of them I felt comfortable and safe with even though all had their strange quirks.
One of them was a Chinese woman around ten years older than me, named F, a shy demure business type lady who liked young men but was socially awkward when it actually came to picking up men and dating. She knew my mistress as a personal acquaintance in their daytime employment and I was offered up to her. Usually our time was split between me as a date for some business social function she was attending, or she would take me out and wine and dine me, followed by all-night sex at an expensive hotel room she had rented for the weekend. With her, I stuck to the role of a boy and none of my fetishism or bisexuality ever came into play. She was sweet and I believe she kept hoping one day I would fall in love with her, because I could sense strong affection from her, but for me she was just not the relationship material I wanted. One thing I did like about her, is in her attempts to try winning my heart over, she would dress up in styles and manners that she knew I found attractive and arousing in women. I love women in business attire, high heels and skirts, the secretary look, and she was more than happy to dress that way when we were together. However she did seem bewildered and confused whenever she saw the photos of me at the mistress’ office wearing womens clothing – unaware or oblivious that I was into other sexual enjoyments. She was sexually naïve and anything besides heterosexuality was foreign to her.
My next regular client was an older European gentleman who simply liked fucking boys. Of all my clients it was usually cut to the chase with my clothes off and spreading my ass wide for him, or sucking off his cock. He was the easiest to please – and sometimes I just wanted to be used and discarded and so he sufficed my desires in that regards. His was the least developed connection and the abruptness and rawness of our sexual interaction did not lead into any emotional bond for him or for me, it was strictly physical, animalistic, and be done. It was always hard with him, intense like he only knew one gear, grunting away while he grabbed my waist and thrusted. His time was also probably the messiest work, as I was almost always covered in sweat and cum afterwards. He did have a nice cock and I liked sucking it and he would then spray his load over my face. Then and now, I wear glasses most of the time – and he liked seeing cum drip off them. He would pay extra just for me to wear them and I had to start bringing a spare pair along just for him as I did sometimes break them when he got rough.
My third client was a woman around 15 years older than me who liked to dominate and abuse men. I think she was a lesbian and I feel like in the past she had once been intimate with my mistress, just a hunch I always had when around her and my mistress. She liked me because I was into crossdressing and enjoyed playing the sissy, willing to be pegged. I was told she had spotted me at a fetish club one night while out with the mistress, and was taken in with my androgynous appearance as I wore a corset and latex tank dress with tights. Seeing me as part of my mistress’ entourage, she enquired about me and found that I was available for use. Her name was M, and working for her usually required the most stamina from me as our bdsm play was by far the most strenuous and exhausting for me, mentally and physically. She loved verbally abusing me and I would wear dog collars with ‘slut’ or ‘fag’ on them. It was actually one night with her, when she was stuffing a rubber dildo down my throat while she choked my neck, yelling at me that I was a ‘cock loving faggot’, that it dawned on me that I actually was one, in fact. I was tied up in all manner and positions and while I enjoyed playing bitch for her, a couple of trips heading back home, I could still feel the sting of leather burns and bruises she had inflicted days before or my ass was still too raw to sit down without discomfort.
The fourth and last client was a couple – and the most intriguing.
Older, I think in their mid-50s to early 60s. They were both well off. Old money, very old money and lived in a city pioneer mansion. They were also the clients who required the most discretion as she was an artist with a downtown gallery and I think he was high up in finance. My mistress got paid very, very well from them, because over time as we got to know each other, they valued and appreciated my professionalism and respectful discretion. We – and I mean my mistress, myself, and both of them – all knew that I was their dirty little secret, but never once did I ever think to exploit that – simply because they were nice to me and treated me like family when outside their bedroom or playroom. Sometimes instead of sleeping at the mistress’ studio office, I would stay over at their mansion.
With them, I would split my time with him and her separately. He was closeted gay and their marriage was a protective front – although they seem to have had genuine affection for each other and had children around same age as me. He enjoyed how I dressed up in the bedroom, and how I made him feel. His wife was dignified reserved on the surface but a sexual pervert when behind closed doors. She too liked men who crossdressed as well as how I could pleasure her with my mouth or fuck her all night. Often when she and I were engaged sexually, he would get off from watching us fuck.
I had come to their attention in a roundabout way. Not only did they know my mistress socially, but they also knew a casual boyfriend I had in that city. He worked at a restaurant they went to, and during a cocktail party my mistress held one night for her clients and her working boys and girls, they noticed that him and I were an item. Unknown to me, he had sometimes been one of their mutual fucks before I came along. The woman was intrigued by me and one night I got a call from my mistress, sounding me out if I would pair up with my boyfriend and perform a gay show for them. I agreed, mostly because it meant some quality time with my boyfriend. The two of us showed up at their massive home and were led to a room, all in black with a stage at one end of it. Here, for the next two hours, after stripping down for them, my boyfriend and I oiled up each other and we proceeded to dance with each other, our cocks flopping about as we tugged and writhed with each other, before we ended down on the floor of the stage, having sex, sucking each other off, finally ending with us ass to ass with a dildo between us. All while they sat and watched us from two chairs, sipping from their wine or drinks as if they were watching a movie. She got up at near the end and walked up and looked into my eyes as we fucked, staring mesmerized at my facial expressions of pleasure until I finally orgasmed. With semen dripping, she dipped my cock into her wine glass and then drank from it, before giving me this thin but appreciative smile and a wink.
Sometimes when he was away on business trips, it would be just her and I for the weekend and I became her date for going out for dinner or places where she could be discrete with me and not worry about been seen by those who knew her in public. Once I managed to goth her up and took her out to one of the fetish clubs, where she could experience the fetish scene in close quarters and she could relax and be her perv self in public, so to speak. It was intriguing and for me actually arousing to see this mid-late 50s woman, head to toe in a lace dress, her face caked with white make-up and black lipstick and a long black bob wig over her natural, steel grey wavy locks. By the end of the night, I wanted her badly and I took her, much to her delight.
When I decided I needed to retire, due to conflicts and demands with my ‘at home’ life, I had to endure protests from F and the old money couple. Both wanted me to stay in their lives and continue, but I felt I couldn’t mesh my sexclients any more with home life or day job. F hinted she would marry me if I asked, while the old couple even offered to set me up with one of their daughters for a wife match, so I could still stay close to them, but I immediately turned down that offer as it would have been beyond awkward knowing ‘my wife’ had no knowledge that I had repeatedly slept with her parents.
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Posted on : Sep 24, 2021
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Commented on Sep 25, 2021
Great description of an very interesting time
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