JollyJohnnyP's blog post - Transexual Encounter (gay fiction)

I was out walking in a local park when I saw, coming towards me, a most interesting looking person in tight light grey leggings and a figure-hugging pink lycra top. I say "interesting" because there was a very noticeable bulge in the leggings at the crotch and also two equally obvious bulges at chest level with the nipples clearly outlined. I wanted to get to know "her" and I hoped that she'd be interested in me, a gay transvestite male. As we approached to within talking distance, I said,
"Good afternoon. Do you have the time?"
I ought to mention that my clothes at the time comprised a silky blouse, not frilly or lacy but fastening the women's way, and a pair of women's shorts, not blatantly feminine but pleated in a way only found on feminine shorts and trousers. Underneath, my undies were all feminine - a lacy cotton chemise and a pair of tight black lacy panties with frills across my buttocks. I was also wearing trainers and white socks.
Her reply was most encouraging,
"I do. Do you have the inclination?"
I replied in the affirmative and joined her walking back in the direction from which I had come. Our conversation revealed that she had noticed my feminine blouse and shorts and had thought that I might be an interesting person to know. By the time we reached the car park we were on first name terms; I had revealed my sexual orientation and interests, in particular a desire to get to know a transexual who had breasts and lived as a woman but had no intention of changing her masculine genitals. She, in return, had told me that she was single and looking for a boyfriend who would accept her as she was and would be willing to take both sexual roles, giver and receiver.
She invited me back to her house and led the way in her car. When we arrived I was pleasantly surprised to find that she lived only a couple of streets away from my home. As she welcomed me into her lounge I noticed a dark wet spot on the front of her leggings where she had leaked a little pre-cum. I commented and after mentioning that her knickers and leggings would have to go in the wash she told me to follow her to the bathroom where, after removing her shoes, she stepped into the bath, turned to face me and her small wet spot became an ever-growing dark area as she deliberately wet herself, flooding her knickers and leggings with the contents of her bladder. By now my cock was rigid and tenting the front of my shorts which were also showing a small damp spot. As my new friend lowered her now sodden leggings and knickers, she bent over, turning her back to me and telling me there was some lube in the small cupboard with the mirror door over the wash basin. I hurriedly lowered my shorts and knickers, found the lube and applied some to her anus and some to my cock. A moment later I was pushing at her sphincter and suddenly as she pushed back I felt her anus yield and I slipped all the way in, my balls slapping against hers as I started fucking her in earnest. I did my best to hold back and managed to last just over five minutes before I felt my spunk rising and the increased sensitivity of my cock which heralds an imminent orgasm. I thrust deeply into her as far as I could as I felt my cock spasm as I orgasmed and shot a huge volume of semen deep inside my new friend. I didn't want to pull out but inevitably my cock softened and slipped out with a soft plop followed by a dribble of spunk. Julie asked me to photograph her anus with the blob of semen still visible. She told me where to find her camera and, after pulling up my knickers and shorts, I took several shots as, once she'd heard the first click, she started pushing out more of my semen, so she ended up with about a dozen pictures of her anus in various stages of discharging my gift of love juice. She then pulled up her wet knickers and leggings and, after fetching a waterproof plastic sheet from her bedroom, she covered the sofa in the lounge with it and invited me to sit down next to her. I always have a need to pee after an orgasm and I mentioned this to Julie who told me to just do it in my knickers as I was sitting there. I followed her suggestion and thoroughly enjoyed the warm flood over my belly, cock and balls as my bladder emptied.
It had been a deightful way to begin a new friendship and I was sure we'd have many more wet and messy intimate sessions in the weeks to come. I'm looking forward to receiving her love juice up my mancunt next time!