Blog : First time with TG

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11/4/2022 7:18 pm

First time with TG

I experimented with a few bi guys into crossdressing when younger but until last weekend had never played with a tranny (transgender).

Adriana sent me a few photos, fully dressed in nice sexy satin dress and a few of her in sexy satin lingerie inc. seamed stockings. She also mentioned that she is a sub, something I had the impression of already and into degradation and humiliation. As a lover of lingerie (and someone who occasionally<b> dresses </font></b>in certain kinds of lingerie for sensual pleasure) and a lover of humiliation from a dom's perspective, I knew we could have some very kinky fun together.
I went so far as to mentioning that my last long term sub affectionately considered me to be a pervert, an opinion that I happily agreed with.

After a few drinks Adriana slipped out of her dress to reveal a sexy figure dressed in seamed stockings and suspenders (garter belt), pink satin high waisted panties with matching pink bra. I took off my clothes down to my own undies; black satin high waisted crotchless panties. Being open crotched my cock and balls protruded from them. I asked to see Adriana's cock. she pulled her panties to one side and to my delight I saw her very large cock. I would guess about 8 inches but also very fat girth. I am also similarly well endowed so it felt natural to immediately touch and play with each other. Her big penis swelled in my fingers and stroked it masturbating her slowly. Adriana dropped to her knees and sucked on my cock. I had wanted to try TG cock for a long time so I suggested we 69. We did 69 with her on top and then me on top. Positioning herself so her head was just over the edge of the bed I slid my cock down into her mouth so that the glans of my cock went into her throat. Gently pumping back and forth I fucked her mouth and throat. Adriana asked if she could lick my asshole. Opening my legs wider I sat astride her face and lowered my asshole down to her lips. She pulled the opening of my crotchless panties wider and lapped at my anus then went all the way in with her tongue. Lowering myself down I rubbed my wet anus against her nose and lips. Adriana had said among other things she identifies as a toilet slave. Pushing with my sphincter as if to go my anus loosened and she went even deeper with her tongue. This was almost enough to trigger my orgasm but I knew I wanted to cum inside her so quickly she turned over and pulled her panties to the side. Pushing my wet cock up her asshole in one big thrust I felt the tightness of her anal ring around my cock. Some hard vigorous ass fucking and her ass was pumped full of semen. Adriana sucked me straight from her ass and i wiped my cock on her face and hair.
Restraining her ankles I positioned her stood bent over with legs apart and I got a glass. Putting the glass to her crotch I told her to piss herself. Nothing was immediately forthcoming so for some encouragement I took a leather tawse and whipped her on each buttock in turn and then very hard between the legs. Adriana squealed and half heartedly asked me to stop. Repeating the lashes I did them twice as hard, even more so between the legs on her balls and cock. A dark patch appeared in her panties which spread outwards and a steady trickle of pee streamed through her panties into the glass. When the glass was almost full I took hold of her hair, tilting her head back and told her to drink it some which she did. Squirting a little lube onto my cock I told her to masturbate me into the glass which she did, making a copious load of sperm float in the pee. Tilting her head back again I put the glass to her lips and told her to drink which she obediently did.
Following some more attention to her crotch with a flogger I released her ankles and told her to sit with her legs wide apart on the sofa and masturbate for me so I could watch. Having never seen a TS/TG climax I wanted to see her do that and slipped an ultra thin condom on her big erect penis to collect the liz. Pushing into her asshole I fucked her quite hard while she stroked and played with her cock. As Adriana moaned quite loudly I watched the head of the condom fill and swell with her lovely cum as her cock squirted. I couldn't resist kneeling down and licking and sucking her balls as she climaxed. Sucking them into my mouth I thought 'sucking TG balls...another first for me'.
Getting back to the humiliation previously mentioned, I got her to kneel astride a bowl and piss in it, then I pissed on her face and in her open mouth, the pee running down her body soaking the bra and panties. Then she was instructed to get on all fours and lap and suck the pee from the bowl.
We continued with some more lashes between the legs and on her ass cheeks, more pissing fun, fun with dildos and vibrators for several hours.


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