A little about me. I’m a 22-year-old American guy. I’m on the slim/toned side, and stand at 6′ 3″. I’d say I’m decent looking, people (girls/sexual partners) call me “cute” a lot because I still have the face of a 14 year old kid and my skin is soft and smooth. I consider myself very open-minded sexually, but wouldn’t really consider myself bisexual since I’m only interested in relationships with women.
I’m typing this on my couch about 8 hours after I met up with my first Tinder date, Jessica, in my new city. I matched with her about a week ago, and thought she looked pretty hot. She was a latina with insanely long black curly hair and smooth caramel skin. She had an athletic body and a face that reminded me a lot of Penelope Cruz.
When I intially looked at her profile I assumed she was a cisgender woman. There was nothing about her that resembled a trans person or any traces of masculinity. So suffice to say when she told me she was trans I was pretty blown away.
I’ll be honest, I kinda have a fetish for trans girls and watch trans porn sometimes. I’ve always wanted to have fun with one.
So, I asked her if she wanted to grab drinks last night and she said sure. I told her I’d be happy to pay since she lives a ways away and had to uber into the city and it was like $60. She texted me about 2 hours before we were supposed to meet and said she wanted to go dancing at a few clubs after we got drinks.
My stomach went into my throat when I imagined myself dancing. I became really nervous, but I wasn’t going to back out and said alright but I would need a few drinks before I started dancing.
Anyway, we met and went to 2 different bars and 2 different clubs and had a good time. I had actually never been to any of the bars in my area yet so it was a cool experience. And a fucking expensive one. I spent almost $200 on drinks, cover charges, and Ubers. Good thing I don’t do this very often or I would be deadass broke right now lol.
She was wearing a red silk cocktail dress and fishnet stockings (those things drive me nuts lol) with a fur coat and heels. I thought she looked really sexy. And her voice sounded exactly like a girl’s too.
We met up at 9 PM and got to know each other. She works at a vet office and draws in her free time. She showed me some pictures of things she had drawn and was actually a really good artist. We got very tipsy at these two really cool bars, and danced at 2 clubs until around 2AM. She started to grind on my crotch area with the beat of the music. She turned to me and kissed me. We started making out on the dance floor and I asked (well I kinda yelled, because the music was so loud) if she’d like to come back to my apartment.
She just smiled and walked me out of the club by the hand and asked if I would order an uber. She was holding on to me as we were walking out of the club, and we started making out again in the back of the uber. Her lips were so big and soft and I was feeling up and down her thighs and butt as we rode home. It was around 3 AM when we burst into my apartment making out and taking our clothes off piece by piece. She pulled my shirt off and started kissing my abs. I took her shoes off and helped her get her shirt off, revealing her small but perky tits.
As I did when I lost my virginity to Katie a few months back, I picked Jessica clear off the floor and carried her into my bed. We were kissing and licking and running our hands all over eachother.
Now, I should probably mention that I had not masturbated for 6 days prior to this, so my dick was pushing at my jeans so hard it was painful.
Jessica took off my jeans and started rubbing my dick through my underwear, which had me shibering in pleasure. She took my dick out and started sucking, it felt so so good. My dick is 7″ long and she was able to fit the whole thing in her mouth.
I pushed her back onto the bed and started agressively kissing her while grinding my steelhard dick on her belly. The only clothing Jessica had on were her fishnet stockings. She said she wasn’t comfortable displaying her penis, so she pulled her legs back on the bed, pulled her stockings back, and revealed her pink asshole.
I put on a condom and lubed up my dick and she put sone lube on her asshole.
I went in slowly.
Then I began to speed up a little. Her asshole felt so good and tight around my hard dick. For a few minutes, the only sounds in my apartment were the moaning of Jessica and I, and the squeaking of my bedframe.
Then, Jessica started to really get into it, and started yelling, “Yeah, fuck me fuck me!”
After a little longer, I pulled out, slipped off the condom, and climbed on top of her.
“I want you to cum on me.”
I was determined to try and cum, and I started jerking my dick. After a minute or so, I started to feel a massive orgasm building up. Then, I reached the point of no return and my dick became a firehose. I squirted rope after rope of thick cum on her face and chest.
Then we both collapsed there. I got a towel for her so she could clean the cum off of her, and we just laid there and kissed for a while.
She couldn’t stay over, so I ordered an Uber for her and walked her down to the street. She gave me one more kiss before she got into the car.
And that was my Friday night. I definitely enjoyed myself, and am really glad I got to experience it.
Source: reddit.com/r/gonewildstories/comments/du325t/mt_didnt_know_she_was_trans_until_she_told_me_and
Was that the last of her?
You definitely need to meet up again and repay the favour of cumming followed by a cummy kiss