I went down to Orlando a few years ago to visit an old high school friend whose birthday lines up with Gay Days every year. He’s gay, I’m straight, and every time I go down there, it turns into a bit of an adventure.
That weekend we ended up at the now defunct Parliament House, which was hands down the best bar I’ve ever been to (but that’s neither here nor there).
Now historically, Orlando has been very good to me. I tend to meet women, hit it off, and go home with them. So walking in that night, I fully expected more of the same.
One woman caught my eye right away. She was tall, blonde, busty, wearing an insanely tight silver mini dress hugging her curves and had the mouth of a sailor. As luck would have it, she was friends with my high school friend that I was visiting.
Also, she was trans. Definitely passing, but trans none the less.
I couldn’t help myself and turned the charm on immediately.
We talked for a bit, flirted, but I got the sense she wasn’t totally into it. And I had that internal “hold on” moment where I said to myself “I’m straight. What am I doing hitting to this person?”.
So I drifted. Talked to other people, had a great time, I’d spot her laughing and talking with other guys and I was fine with that. This was Gay Days, I am straight, she is trans and that’s the end of that.
And then right before last call, I feel a hand on my shoulder.
“Where have you been all night?”
It’s her.
At that point, I didn’t care about labels or logic. She was the hottest person in that bar, and I wanted to go home with her. I had told myself that if I pull this off, I was going to treat this like hooking up with a cis girl who was just really into butt stuff and would completely ignore what she has between her legs (selfish, I know).
She asked if I’d ever been with a trans woman. I lied. Said yes. She invited me over, and the second we got in her car, we were all over each other aggressively making out.
Naturally, I grabbed her tits while she rubbed over my jeans, feeling how hard I was. I was hesitant to touch hers and I said something like “let’s get to your place, fast”.
By the time we got back to her place, I still had that voice in the back of my head asking questions. but it was getting quieter. She told me to go to the bedroom while she gets ready for bed in the bathroom. I stripped to my boxers and lied waiting, watching her. She had removed her tight silver dress, and put on bed time shorts and a t-shirt. I thought, “are we just going to sleep? Maybe that’s for the better”.
Her back was to me and she started brushing her teeth. The movement caused her perfect plump ass to shake and I couldn’t wait any longer.
I got up, crossed the room, and put my hands around her waist, pressing my hard dick against her ass and started kissing her neck. My hands moved up to grab her tits. Eventually I turned her around and we were face to face. I pressed against her again as we started kissing, and for the first time, I felt her hard cock against mine.
I can’t explain it, but at that moment, all trepidation about hooking up with a trans girl went out the window. I reached down and pulled her dick out of her shorts and started stroking it while my tongue was in her mouth. It was about 7 inches, cut, completely smooth and beautiful. She did the same to my dick. She started rubbing my dick against hers and stroking them both at the same time and I freaking loved it. My thoughts went from “I can’t do this” to “this is what I’ve been missing?!”
We got into bed and started rolling around like animals. She would pull my hair while liking my neck. I played with her big tits while feeling her dick rub all over my body. She was so soft and smooth and aggressive and hot.
I was kissing her all over her body and not after long, without any hesitation, I did something I never in a million years thought I would ever do. I pushed her on her back, her tits bounced as she hit the bed, and her beautiful hard dick was pointing straight up. I started slowly stroking her shaft. She started breathing heavier. I spit on the tip, bent down, kissed her dick from the base to the top a couple of times, and finally wrapped my stubbled straight cis male wet lips around her cock and started sucking.
It unlocked something in me. I loved it. I loved every second of feeling her hard dick in my mouth, on my tongue, pushed against my throat, pressed against the inside of my cheeks. When my hands weren’t grabbing her big tits they were grabbing and squeezing her ass to make her dick go deeper in my mouth. She was moaning as I let the drool fall out of my mouth on to her. After a few minutes she said “fuck me”. So I did!
Here’s where I think the cat was out of the bag regarding my experience with trans girls.
I bent her over and tried to shove my dick in her ass because that’s how I thought you were supposed to do it!
She stopped me, flipped back over on her back, and guided my dick into her. I started slow, kissing her lips and tits and slowly stroking her cock. She continued to moan and tell me how great my dick felt in her ass. Before long, I started fucking her harder and faster. When I wasn’t jerking it, her dick was flopping around like her tits. Before I could cum, she pushed me off, got on top of me and masterfully started jerking me off until a came all over her face. Followed almost immediately by her cumming all over my stomach.
We both toweled off, made out for a little while on the bed and went to sleep naked and spooning.
I woke up with my morning wood pressed against her. We didn’t care about morning breath, and made out and fooled around a little more. She got ready for work, and drove me back to the bar we had met at.
That was my first experience with the male genitalia that was other than my own, and as I stated earlier, I loved it! And I’m glad to say it wasn’t my last time.
I still identify as straight. I’m still attracted to women. Always have been.
If she’s beautiful, if the chemistry is there, and if it feels right, I’m in.
And if that beautiful, curvy woman happens to come with a little something extra?
Turns out I’m into that too! 😎
I hope you enjoyed my little story.