Since my fiance and I broke up, I got really into prostate massage and got some toys to help out. I would sit for hours and watch porn and just slowly milk myself before letting my self cum. I got into a lot of shemale and ladyboy porn in the process and eventually started jerking off to femme bois and some crossdressers as well. I even mail ordered some lingerie to wear while I do it and started to shave my legs since I have a stocking and garter belt fetish. After a while more I wanted more than just toys in my ass. I wanted to have a real life encounter but didn't know how to do it but figured a gay bar was the best bet because I could likely find someone for a casual hook up who I could let fuck me in the ass. But without the lingerie I'm just not as into it and I wasn't sure if I could really do it. I put on a pair of panties, a garterbelt and some stockings under my jeans and went to a gay bar last weekend, but chickened out because I don't know much about gay culture and don't know what they think about crossdressing. I looked at a few guys and wondered what it would be like to suck their dicks but got scared, went home and jerked one out instead. Last night I tried it again and hooked up someone. He didn't seem to mind my stockings. We sucked each others dicks for a little bit, and then I let him fuck me in the ass. It was different than milking myself, but I really liked it. Now I want to do it again, but this time I want to suck more cock and actually swallow someone's load. Some people on here will call me a fag, but whatever, I bet they'd still let me suck their cocks too.
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I confess I may have fucked a post op ladyboy today.
I'm in Thailand and this afternoon I went for a sex massage. I pick the girl form the goldfish bowl, she looked ok but when she came out I noticed she's a bit tall for a Thai girl. So as she took me to the room we started talking and her voice was a little bit deep but i was still unsure
. So when I got striped ready to get into the bath I watched her undress half expecting her to have a dick. I was thinking at this time what will I do if she does? Do I run out the door or do I just go with it? I've always been curious.
Anyway she takes of her clothes and she didn't have a dick but she did have a big bush though, so it was vary hard to get a good look at her pussy to judge if was a post op pussy or areal one. I'm sure she had a boob job and a flat stomach no stretch marks witch is unusual for a girl in her early 30s to be working in a place like that, usually there's kids to be fed that's why there in that line of work.
Later as I was giving it to her looking down on her pussy it did look normal but still hard to judge because of her hairy bush.
So I'm sure if I fucked a transsexual today
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