My First Time With A T-Girl hot Sex Stories – Y2 Stories

One hundred percent true story, I swear!

It was the 80’s. I was in my 20’s, good looking, horny, and bi. I’m still horny and still bi, but not as good looking as I used to be. I had recently discovered the joys of cruising, hooking up anonymously in mostly public places. I started going to this old theater that had converted to porn some years earlier. It was a fun place with a lot going on. Besides guys hooking up with each other, management let hookers work the place too. So you could get as much dick or pussy as you wanted.

The place was particularly busy on Friday nights. Besides the hookers working and guys cruising, swinger couples often met there too. I went in one Friday and the place was really busy. I got propositioned by a couple hookers as soon as I walked in. I wanted to see what was available before I settled on one of them, so I politely declined. I walked around a bit, taking in the action going on around me. Guys were blowing each other, women were blowing guys, all kinds of different combinations. I decided to sit in a somewhat empty area towards the back of the theater and just observe for a while before I got into anything.

A hot blonde caught my eye fairly quickly. I watched her stroll up and down the wide middle aisle, flirting with guys as she went. I thought that if she was a hooker, I’d pay for some action with her. She was probably in her late 20’s. Her hair was shoulder length, her sensuous lips painted red, as were her nails. Her tits weren’t big, but they filled the tight, white sweater she wore nicely. Her long legs were encased in fishnet stockings, her leather miniskirt short enough to show that they were held up with a garter belt, her lacy panties peeked out too. Her shoes were the high-heeled “fuck me” variety.

I watched her for a bit before she headed to the back of the theater, out of my sight. I returned to watching the action around me and the action on the screen. It was a porn theater, after all. After a bit, I heard someone sit down behind me. Like I said, the area I had sat in was fairly empty, so I figured whoever sat there was looking to hook up. I didn’t want to appear too eager, so I didn’t react right away. I sensed some movement and heard some moaning that sounded feminine. Finally I turned around to see who my prospective partner was. It was the hot blonde!

I couldn’t believe my luck! She had passed all through the place and apparently chose me to hook up with despite not even having spoken to me. Wordlessly signaling to each other is usually how hookups between guys go, but not with the hookers, you have to negotiate with them. Turned out, she wasn’t a hooker after all.

The movement I sensed turned out to be her stroking her beautiful cock! She had her miniskirt pulled up and her lacy panties pulled aside. She was so damn pretty that I had no idea she was trans! Her cock was magnificent! About 8 inches and thick! Completely clean shaven, both mound and balls. She was slowly stroking it as we locked eyes. I reached out to grasp it and she put her hand over mine. I got up and climbed over the seats, pulling out my own stiff cock before I sat next to her. She took hold of my 6.5 inches as I once again took hers in hand. Our lips and tongues met in a hot, passionate French kiss as we jerked each other.

I had been with lots of women and men at this point in my life, but never a trans woman. I had never been with any woman as hot as her, for that matter, and I had been with some good looking women. I was so damned turned on! We had been making out for a while when another guy came and sat next to her. She didn’t even look at him when she reached over to grasp his cock. It seemed like she was expecting him. He whispered something to her like, “Looks like you found a good one, baby.” It was obvious then that they were there together.

She broke our kiss and turned him, whispered back to him, “Yes, he’s cute. “. That was fine with me. I was happy to be part of this three-way. I really wanted that beautiful girl cock in my mouth, so when the two of them started making out, leaned over and started sucking it. I could hear her moan into her boyfriend’s mouth. I licked it up and down, sucked it down to the root, licked and sucked her beautiful balls. I reached under her sac and tickled her asshole. This drove her wild and soon she was shooting a huge load in my mouth and across my face. She had stopped kissing her boyfriend and moaned, grunted, and loudly yelped her climax out. Other people heard her and stopped to see what was going on.

She grabbed my face and started kissing me again, licking her cum off my face. Then she stood up, turned around, bent over, and pulled up her skirt to present her her shapely ass to me. Her ass, legs, and hips were so perfect, it was hard to believe she wasn’t actually born a woman. She pulled her panties away from her asshole and wiggled her sweet bum at me as she bent over to take her boyfriend’s cock in her mouth. I spread her cheeks open and stuck my tongue up her tight back hole. It was just as hairless as her cock and balls. She squealed at the sensation.

I licked and sucked her boy pussy like it was a girl pussy, getting it nice and wet. Then I stuck one, then two fingers in it to loosen it up. She turned and told me to get on with it and fuck her already, I was driving her crazy. I told her I didn’t have any condoms; she said she didn’t care, just do it! Who was I to argue? I knew I was clean, but she couldn’t know that for sure. I stood up and lined up my cock with her pucker. She was sucking her boyfriend again as I slowly entered her, but threw her head back and moaned at the intrusion.

I started pumping slowly at first, then picked up speed as I went. I looked around and saw that our threesome had attracted an audience. I also got my first look at the boyfriend. He was much older, probably in his 40’s. Good looking guy, though. I would have been happy to hook up with him myself. These distractions actually kept me from cumming in her sexy ass too soon. But I could only hold off for so long.

Soon I shot my own huge load up that tight, hot fuck hole. I quivered and grunted as I came, holding in place for a few seconds before I pulled my softening cock out of her with an audible pop. I’ll never forget that sound. I flopped back into my seat, spent for the moment. She was still sucking her boyfriend’s cock, her ass still pointed my way. My cum was dribbling out of her still gaping hole. It looked so tasty that I couldn’t help myself, so I licked and sucked my spunk out of it. She was moaning again from my tonguing. Her legs were quivering. I didn’t know how she held her position, bent at the waist, for as long as she did. I felt relieved for her when her boyfriend finally came in her mouth.

She flopped herself down in her seat, grabbing my face and kissing me again. I still had my cum from her ass in my mouth, and she had boyfriend’s load in hers. We shared the two loads before she broke the kiss and turned to him, letting him have a taste. After a few minutes rest and thanking each other, she pulled her panties and skirt back in place. We two guys zipped up, and the three of us went our separate ways, the two of them leaving the theater together. I stuck around for a while and hooked up with a couple guys that had been a part of the audience watching our show.

It was a great night. Unfortunately, I never saw that couple again. I’ve been with several other trans people since then, both MTF and FTM and enjoyed every encounter, but that first one will always be special…