Sorry if writing is bad. Doing it from my phone.
So little about me, I’m 25 and straight my whole life. Never even thought about being with a guy or Transgender. Got out of a shitty relationship and was swiping on tinder one night. There was this sexy 45 year old woman who looked like a sexy soccer mom with a boob job. She was about 5’9″, red hair, nice big round ass, and big breasts. We matched and began chatting with her. We exchanged numbers and texted for the next week. I was going out of town that week so we made plans to grab dinner when I got back.
We finally got out to dinner and she was super nice and funny. We were clicking, and as we go out to leave, we begin to make out in the parking lot. She propositions I come back to her place, and I quickly agree. When we get to her place she pours us a drink and puts on a movie. She then goes back into her room for a while to change. When she finally comes back she’s wearing just a sexy black bra and black panties, but to my surprise there was a 7″ thick Cock in her panties. She saw I was quite surprised by it, but she strolled confidently to the couch and began to unzip my pants. I was so turned on at this point I knew there was no going back.
She slides my jeans off and my Cock comes out of my boxers. She begins to give the best blow job I ever received. The whole time she’s moaning and stroking herself. After about 2 minutes she stops and we begin to make out and undress. When we both are naked, she begins to reach around to my ass and begin to play with my butt with her finger. This absolutely drove me crazy. She puts a finger in my ass, which at first I hated, but after a couple seconds felt better as I relaxed. She could tell I was enjoying it, so she proposition ed to go to the bed where there was lube.
We go to there and she takes the lube and begins to lube up my ass with her fingers. I was pretty nervous and almost shaking with anticipation. She lays down face up on the bed and I begin to work her dick up my tight ass. It was very slow and uncomfortable at first. She kept on wanting to go faster and I had to hold her back from thrusting. To be honest it wasn’t much fun until about 10 mins in and I finally got all of her in me. It was euphoric. I begin to slowly go up and down and she’s just moaning and yelling my name. I rode her for about 5 mins of her fully in before she came. Feeling her cum I immediately I came right after blowing all over her tits and face.
I ended up sleeping at her place that night. I was super sore for the next few days, but I’ve seen her about 5 or 6 times after that. Maybe I’m not totally straight because I love the feeling of her dick inside me now.
Source: reddit.com/r/gonewildstories/comments/50i7em/first_time_with_a_transgender_woman_from_tinder
Good work.
Sounds like a lot of fun!
She is what I imagine my first time being toped to be like, nice story man!
Awesome!
So she didn’t mention she had a dick before you guys for intimate? I’m not trying to hate but they seems like an important thing to mention before you get to the nightcap part of the night. Not everyone likes surprise penis.
Best of all worlds
This is one of my top fantasies. Even more so if it had an element of force, as in her forcing me to take it hard…