I consider myself straight most of the time. Besides women, who have been 90% of my encounters and relationships, I have been with a handful of trans women in my past. Recently, I have been watching more trans porn and I have had such an itch to be with one again. It had been a good couple years since my last encounter, when I traveled to Boston for work. I’ve been posting on local R 4 R subs the last couple weeks. After weeding out fake accts and non trans people, I started to chat with one individual for a few days. We got the basics out of the way and became really flirty on another app with each other. She had been transitioning for a couple years now and looked fantastic. She has very pretty green eyes, a killer figure and such a pretty smile. I thought I hit the jackpot and couldn’t believe my luck. But, there is always a catch. She was in town and staying with her family at a hotel for the week for a family wedding. They were flying back out this last Wednesday. All day Monday, all I could think about was kissing and touching her. It was driving me mad. It was bitter cold outside. Towards the end of my work day I texted her and asked if she could hang out. She said she had like a 2 hr window before her family was back from shopping at a nearby mall. I said that’s fine and that I had to see her and that we would make it work.

I hopped in my full size SUV and headed over to get her from the hotel. You’re probably thinking, why not go in and go to her room. Well, taking a chance of her parents coming back would not be ideal. I arrived at the lobby and texted her. She came out the door and hopped in my vehicle and looked at me with her pretty eyes and smiled as she said hello. I instantly melted and reached in for a quick peck on the lips. She didn’t have much time and I didn’t want to waste another minute of what time was left on finding somewhere to go. There was a big box store near the hotel. We decided to give it a shot. I pulled in and parked pretty far from the store, in between cars. It being so cold, I figured it had to be employees parking there so we should be safe. I also have tinted windows so it helps. I put the car in park and without hesitation we both got out and jumped in the back seat.

My truck was nice and toasty. We took off our jackets and started to make out. She had nice soft lips and knew how to work her tongue. I was instantly aroused to the point it was hurting. As we kissed, I unbuttoned her cute little flannel shirt and pulled up her sports top. I’m not sure her breast were big enough for a bra but they were a handful and felt so good to caress. As I teased her nipples she started kissing me harder and I knew she wanted more. At this point, with the cold and our heavy breathing, the windows were all fogged up. I unzipped my pants and took them off, revealing my throbbing penis. I unzipped hers and took of hers to reveal the same. We both started to stroke each other as we kissed some more. I could feel her wetness whenever I’d slide my thumb over the slit of her penis. I whispered to her “I want to taste you” and she said the same. I laid down on my back and she turned herself around and sat on my face. She propped her ass up and let me take her in my mouth. Being on meds for a couple years, she was not big and I was able to take her all in. She groaned as she leaned down to stroke me and the she started to take me in her mouth. She tried a few times to take me all the way in but started to cough. She was pretty good at this. She massaged my balls as she stroked me and sucked on my head. I wet my finger and slid it in her ass as I sucked on her rock hard penis. I could taste the sweetness of her precum and knew she was feeling good. A couple mins of my finger being inside her and I felt her prostate enlarging and knew she was close. I started sucking faster and put more pressure on her rock hard prostate until her clear girl cum dripped in my mouth. Her moaning and shaking as she came. I swallowed every drop. She got off me and I slid to one side of the bench seat. She got between my legs and propped up my legs. She licked my asshole and then left some spit on it. Now she slid a finger in me and rubbed my prostate as she sucked on me. This lasted for a couple mins until it was my turn to explode. Unlike her little amount of cum, I filled her mouth with mine and she took every drop too. It felt so good. I sat up and kissed her some more until she turned to look at the time and said she had to go. We got dressed and hopped back in the from seat and I took her back in time. We kissed once more and told each other we had a good time and promised to reconnect next time we were in each others town. I smiled the whole way home. It was such a great experience. We still chat all the time. Sorry for the novel but I wanted to explain it in detail. I hope you enjoy my experience.