My First Time
I got into trans women and transvestites in the early nineties and back then it was far less in the political and more sexual. Most of the trans women and transvestites I met were part of the fetish scene or they were sex workers. There was always a sense of danger, secrecy and forbidden fruit to the whole experience. The trans women and transvestites I met would dress in the most provocative ways and usually be based in basement apartments in the darker side of town. The whole experience was thrilling. It had nothing to do with wanting a loving responsible relationship or the political struggle to be accepted. It was knowingly about sex, secrecy and the juxtaposition between desire and taboo. Whilst I totally support trans rights and their desire to be accepted fully rather than sexual oddities, I must admit I miss the sleazy forbidden nature of of those times.
When I was 19 my first sexual experience was with a 50 year old transsexual sex worker who took me into a deep sexual fantasy world I still have dreams about.
My first time with her I spent an afternoon alone with her in her apartment in the red light district.
She was resplendent in the outfit of a rich older lady. Heavy make up, a big blonde bouffant wig like a matronly heir to Joan Collins. She wore a pearl coloured silky blouse and a black pencil dress with a split up one leg revealing her loooong, thick stocking clad leg with the pale skin of her smooth thigh provocatively exposed and framed by her suspender straps at the top of her sheer stockings. She was 6ft plus in her black shiny high heels and I was a small teenager at 5ft 6". I quaked with excitement standing next to her and looking up at her breathing in her old fashioned perfume.
I spent ages with her sitting in her darkened apartment watching TV as she drank wine and smoked her slim menthol cigarettes and I sat expectantly at her feet and filled her wine glass when she required a refill. After what must have been an hour of me breathlessly waiting at her feet she fixed me with her stern gaze and opened her thighs revealing her bulging, black silky knickers. Something snapped inside me and I kissed her stocking tops, suspender straps and the creamy white flesh of her thighs and begged her to make me her lover.
I wasn't just overwhelmed by my respect, awe, lust for her sexual power. I was acutely aware of how forbidden my feelings and the position I was in were. I drank in the warm, musky scent of her private parts which were inches from my face barely hidden behind the thin fabric of her undies. As my face nestled between her thighs and I gingerly kissed the skin of her thighs around the leg elastic of her knickers and she reached down with one hand and pulled my face into her crotch as she used her other hand to pull her panties aside so her erect penis sprang against my eager face. Her penis was so perfect, pale skinned soft, warm and meaty. 8" Uncut with a pink pouting foreskin and framed by an unruly bush of blonde pubic hair. It was engorged and heavy as it dangled between her legs. The scent of talc and musky sweat overwhelmed me as I gingerly kissed the tip of her powerful penis and whispered my muffled devotion to her from under the steamy folds of her skirt. She became so erect her penis defied gravity and I was able to kiss the underside of her shaft, respectfully hold her balls and bury my nose and lips in her pubic bush.
I had never been so excited and in need for another human being in my life and she knew it. She had me take off her shoes and kiss and lick the stocking soles of her feet as she masturbated then literally scooped me up in her arms like a rag-doll and carried my quivering teenage body to her bed where she stripped me naked and took my virginity
I was infatuated with her after that and kept going back to her for years after.
That was my first sexual awakening.
PS: The pictures are not of her but they remind me of her or my time with her
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05-11-2015
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