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My First Time With A Transwomen
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First off let me say I love this subreddit & love hearing others first time transwoman escort stories. My story starts off very simple probably like others. I’m a younger guy 20 years old who was always into cis-women porn. One night when I was in high school, I clicked on what I thought what was standard women fingering herself webcam porn which actually turned out to be a chick with a dick moaning & stroking. At first I wasn’t into it, then I got hooked to it & now to this day it’s my favorite porn genre. I’ve wanted to hook up with a transwoman for a long time now for around 2 years now. Anywho let’s get to the story of my first ever hookup with a transsexual woman. I showed up at her hotel room. She was probably I’d say around 5’10 to the 5’11 range for height. She was some sort of Spanish decent & she smelled great, had long black hair, had a nice fat booty & some decent sized breasts. Best of all was her penis. Pretty big for size & I just want to say I underestimated penis sizes. For my first time I think I chose a transwoman who was way too big for me but I still had so much fun. We started off by taking off our clothes. She had me lay down. I’m not too big in terms of my own penis so I specifically bottomed for her. Basically I started out sucking her penis on the bed it felt pretty weird at first but then I calmed down. Giving her head was honestly my favorite part. Then she tried to perform anal on me: it was my first time. She was too big. Didn’t really work out. I was way too tight so eventually she had to stop. Then she face fucked me for like 20-30 minutes. Then she pulled out then came on my face. We cleaned ourselves after that then I thanked her we laid there for a little bit cuddling together & kissed a little bit. This was such a fun experience that I would recommend to all curious guys! It was very fun but I’ve got to emphasize this one point. Fellas: Before you try to go see a functional trans women with a large penis: if you plan on having her perform anal on you, it might be best to practice with a bigger dildo before actually trying it from another person. Start with a small dildo then work your way up cuz you can experience a pretty decent amount of pain in your anus if you’re still tight & you’re a beginner to bottoming. But sucking her off was fun, having her face fuck me was awesome then she came. 8/10 experience in my opinion. UPDATE: Saw her again for a second time! Had a ton of fun again & this time I was a lot more relaxed so she topped me again I was still tight but it was much better this time around. Then she face fucked me which is my absolute favorite part about sex with a functional trans women is having her face fuck you &/or giving her oral. This time some of her cum got in my mouth. She is flying back to her home country so I won’t see her for a while but we genuinely like each other & I can’t wait to keep on seeing her whenever she’s in my neck of the woods (no pun intended). 10/10 experience!

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2 years ago