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My first and only time with a transvestite
This is a true story that I would like to share, and happened during a holiday trip to the beautiful country of Philippines, 4 years ago.
A group of four friends and myself, decided to spent a week at a resort near Cebu city. The guys were talking about the crazy nightlife,
and how they wanted to meet local girls and get hammered. I mostly wanted a peaceful few days next to a pool bar. I had the luck to had
had extensive holidays in my time, as I was mostly working at resorts around the med for many summers. Sex was plenty, as was short term
relationships, of which I had had enough in all fairness.
On the third day there, the guys convinced me to follow them to the nearby town, were a nightlife crowd was gathering. As we sat in the tiny bar, we started attracting
a curious crowd of locals, from watch sellers to girls and women of all ages. Some of the girls were pretty, some other indifferent, a lot of them ugly. What was astonishing to me, was the flirtatious nature of them, the politeness and the silly giggles. I was not in the mood for sex, but I bet I could have gone back with at least a couple of them.
As my partners in crime were indulging in the spoils of love, a transvestite dressed in a killer miniskirt sat close to me. That she was a transvestite was obvious, although she had a killer body, and the miniskirt tight on her waist was complimenting her figure. Why you don t play with the girls, you no like girls? , she asked, to which I replied that I wasn t in mood for it. We started talking about life and her dreams. She had a feminine voice, somewhat deep. She was talking about her dreams of moving to America one day, and that she wanted to work as a nurse, although currently she was a hairdresser. I noticed she was very well mannered. In my life I have met a lot of gay men, few transvestites and transsexuals. I always thought they are good fun to be with, but never had sexual contact, despite having been offered a few times. She was different, less confident about herself, with a romantic melancholy on her face. Small dark eyes, very penetrating, and a long slim nose. Her chin was almost that of a young boy, but she was just 3 years younger than me. Very smooth skin, hairless, with nice long legs.
At some point she got up. I am going to toilet she said, and turned away to disappear in a narrow dark corridor. I noticed the nice curvy arse on her. And then it hit me! I needed to fuck that arse that same night! As she returned, I said I would love to see your place . She replied that it wasn t a problem as her house was 5 minutes away. I said goodnight to the rest of my friends, who were already drunk and half asleep.
I followed her. She was about a head taller than me. We arrived at what seemed to be a very modest house, with some flowers at the front in makeshift pots. She opened the door and let me in a very modest accommodation with a room adjacent to a tiny kitchen. She had a double bed, but the walls were in a terrible need of fresh paint! Sit , she said showing the bed. You are my first boy , I said. She laughed I don t believe you .
Since the time I knew I will fuck her, I was wondering what would happen if she wanted to do the same to me. What if she had one of those massive cocks like the shemales in porn movies? What if she wasn t satisfied in a passive role? With these thoughts in my mind, she was pulling down her nickers to reveal a magnificent arse. I felt my cock throbbing. Her slim legs were ending in a curvy bum, with muscle. She turned around to reveal a black thick bush. To my relief her dick was about 1inch. Under the heavy bush, she pulled the foreskin back and then I realised she was already erected. The glans was tiny,the size of her thumb nail. Her dick was strangely small, but her scrotum was enormous! The scrotum was clean shaved in contrast to the bushy pubic hair.
I stood up, pulled down my pants and underwear, my cock was hard as fuck, the cock head purple from the blood flow. She approached and said Your cock is curvy like a banana . She took it in her hands and started softly rubbing the shaft. She had taken off her heels, and we stood at the same height. She came closer, and with my cock she rubbed her cock head. A current of lust as I felt the tiny red head with my urethra, hot and moist. She pushed closer, so I could feel her enormous balls squeezing against mine. You shave daily? she asked, I try I replied, and felt her soft hand rubbing my balls. I reached for hers. I felt them cool and heavy in my palm. They were two massive balls, smooth and sweaty. Baby, suck my nipples she said with a fainting voice. I took her breasts in my palm. They were budding, as she hadn t operated yet. I suck on her nipples, feeling the areole, salty and dry. As I had bend to reach her chest, my cock head had pressed against her massive balls, her scrotum resting on my cock, with the two balls hanging either side of my glans. I breathed heavily, as I was thrusting my cock under her scrotum. She moaned.
I want that cock inside me she said, and she kneeled at the side of the bed. She lift her magnificent arse, lowered her torso and rest her head on the bed. The crack was deep, I held the cheeks with my two hands, and pulled them apart. The smell of sweat and human body filled my nostrils, as I was blaming my unpreparedness for not bringing condoms with me. Like she felt my hesitation she mumbled Don t worry baby, I douched earlier. FUCK ME . I looked at her tight hole, clean shaved and bleached. My cock was wet and drops of precum were forming on the glans. Her balls her hanging half way down her inner thighs. I lined my shaft with her crack and rubbed it against her cheeks. As I pressed against her, our balls touched repeatedly, and I felt their weight while mine slapped against hers. I pulled back and my glans left a trail of precum on her left asscheek. I braced myself for pain as I held my cock against the asshole. The precum helped, to slide my cock head inside the tight hole. I watched my glans disappearing in it, as she grunted an Aah .
I spit thickly aiming on my shaft and pressed steadily against her. Till all of my cock disappeared inside her ass. I pulled slowly back and spit a couple more times on the hole. We both started breathing heavily, and the next thrust was easier. I stepped on the bed to rest my knees, and I was physically on top of her ass. Then I noticed the mirror at the side of the bed, right in front of us, that was positioned in such a way that we could both see our reflection both from the front as well as from the back, as another dressing mirror was right behind us, on the other end of the room. I just got so horny by watching the action, from every angle. My hairy ass was making a stark contrast to her hairless one, and my balls were bouncing nicely, as I was thrusting my cock almost vertically into her. I had the chance to compare her hanging balls, that were roughly twice larger than mine, hanging heavily from a long scrotum, between her legs.
We were both drenched in sweat, I saw her back glistening. She was masturbating her cock, while I stepped down from the bed and onto the floor, continuing my thrusting action. I felt her hand holding both sets of balls at some point, while my dick was entirely inside her. You make me crazy I whispered, as I stopped the thrusting to feel the moment. She lift her torso to a proper doggystyle position. Fuck me hard baby, I wanna cum to which I replied a faint Me too . I cannot say how long and how forcefully I thrusted. At some point I felt the air as my cock head popped out of her narrow hole, and the a painfully hit her left cheek. She reached to grab it and pressed it nicely in her gaping hole. We both moaning and grunting.
At some point, driven by the moans, the rhythmical slapping noise of my body slapping her ass, her hand rubbing my balls, I couldn t hold more. I m cumming I grunted, and pulled my cock out , as three ejaculutations directed a rather runny cum, on her hole, down the crack and dripping from her balls. I was still holding her, when after a few moments of intense masturbation, she cum too. From her tiny glans and onto the bed cover, seven large thick ejaculations, produced a pool of thick, creamy semen.
It was the fuck of a lifetime for both of us. I layer beside her breathing heavily, and light headed. You fuck good baby she managed to wispear and reached over to kiss my chest. Can I take a picture of you? I asked. Only my ass baby. ,she replied. Fine with me I laughed. And the pictures are now on my profile.
Hope you enjoyed!
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