ThatGuy41

ThatGuy41

M44

Unexpected encounter

March 11 2025

After the end of a long relationship I was not doing well so my friends decided to take me out for a night of drinkng and strip clubs. The first stop was a club where I saw an incredibly beautiful woman. I thought I had no chance but still went over to her and offered to buy her a drink. To my surprise she accepted and we started talking.

We ended up dancing (well what I did what I charitably call dancing). My hands on were on her hips and I went to pull her closer. She stopped me and I thought I'd fucked up. She looked me in the eyes and said "Before we go any further, I need to tell you I'm trans". I was a bit shocked. I have spent the majority of my 43 years assuming I was straight but here was this beautiful woman who just happened to have a cock. I could see she was worried how I'd reacted. I just pulled closer so we pressed against each other and told her that was absolutely fine with me. I could feel her bulge and she could feel mine. We smiled at each other and then kissed. She then whispered in my ear "I love not to far away if you want to go somewhere more private". I wasn't gonna say no. I told my friends I was leaving and we got a taxi to her place. We spent the majority of the ride kissing. She was an incredible kisser.

We arrived at her place and she lead me to the couch where we continued kissing. She straddled me and took off her top revealing a beautiful set of tits. I wasted no time in taking them in my mouth and teasing her nipples with soft flicks of my tongue and gentle nibbles. She asked if I wanted to see her cock. I happily said yes. She stood up and removed her pants. Her hard cock flopped out in front of my face. I'd never been that close to another cock before but that didn't matter, I started kissing the top and then licking up and down the shaft. Her moans let me know she was enjoying it. Turned on by this I took her cock in my mouth and started sucking. She was thrusting into my mouth and soon she was filling my mouth with cum. It was amazing. She leaned down and kissed me and then said "your turn". I quickly undressed and she got to work giving me the most amazing blow job I've ever had. After I came in her mouth, we went to her bedroom and got on the bed and caressed and kissed each other until she was hard again. I looked at her and said "I've never thought about this till now but I want you to fuck my ass". She asked if I was sure and when I assured her I was she lubed me and her cock up and then slowly slide her cock into my ass. It felt very different but amazing. She started thrusting harder and fasted and then she pulled out and shit her load all over my ass and back.

We went back to kissing and then asked if I wanted to fuck her ass. Again, there was no way I was saying no. Her ass felt amazing around my cock and I came hard and fast inside her.

When I went out that night I never expected anything like that to happen. It was an incredible night that led to a few more amazing fuck sessions.