While it has never happened since, I can honestly say that I don’t regret the experience, albeit the escort part I could likely have done without.
I was around 22 years old, and with time on my hand and the internet being what it is I found myself drifting from time to time to shemale porn. Now don’t get me wrong, if I was, and still am, attracted to women and women only. But I found that woman was more of a description than a gender in this case. So ultimately anyone I happened to watch was a woman, with the exception of what happened to be between her legs.
This carried on for a fair bit longer but one long weekend it just got the better of me. I HAD to get laid and, at the same time, I HAD to know what it was like to be with a trans woman. Now I’ve never been the outgoing type. Yeah I keep get a good conversation going but I never really had the confidence to get it started, not to mention, I had no idea where to look. So my porn addled mind jumped to the next best alternative, an escort.
I could look around, “window shop” if you will, until I found someone I was interested in that was nearby. It was easy, private, and perfect, so the thought of this being an escort who would have been with other men, likely in the same day, was of no concern. It didn’t take too long, not being in a major city lead to limited choices but, with my luck, the right one just happened to be nearby and visiting.
She was tall, beautiful, and much more feminine than her pictures. There really was no way to tell that she was no ordinary woman. So I stepped inside the hotel room, we chatted and she made sure to tell me to take my time as she recognized it was in fact my first time (with an escort/trans). She offered me her shower to freshen up, and though I didn’t need to I found it helped calm my nerves. Though I didn’t stay calm for long.
Turning the corner after stepping out of the bathroom I saw her in all her glory, and with that, all worries gave way.
As I mentioned, even with this new horizon I still hadn’t changed. What I was attracted to was a woman and, despite the cock steadily growing between her legs, that is exactly what was standing before me. She had long blonde hair, perky c cup breasts, an ass to die for, and legs that seemed to go for days.
Though at a loss for words, she knew I liked what I saw. I was at full mast within seconds. Walking up towards me she pulled me in for a kiss. Our tongues danced between our lips while her fingers danced around my now throbbing cock. I felt her stroke and tease it, gently rubbing it against hers.
After what felt like forever she pushed me onto the bed. Then slowly crawled up between my legs, kissing my thighs as she made her way up to my cock. I honestly thought I was going to blow. I’ve always been a fan of foreplay, and love to go down on a woman, but I’ve never had the same done to me to this effect. It was an experience I could never describe, and it was only the beginning.
After a while I sat up, and told her to lie down where I did. I still can’t believe it now, but I wanted to return the favour, even more, I wanted to see what it was like. I still can’t explain it. While it didn’t feel particularly good, it wasn’t bad either, however, that changed when I heard her moan. No matter what, what I love most is to make a woman moan, and now I knew that whether it was a cock, ass, or pussy, it didn’t matter as long as it was driving her crazy.
Stopping me before it went too far she asked if I was ready and, to be honest, I wasn’t. But then, when she bent over and showed me that glorious ass it didn’t take much convincing. I slipped a condom on, grabbed her ass, and slid every inch inside.
Now I don’t think I’m a particularly blessed man, but I do like to think I’m at least above average. 7″ long and 6.5″ thick (circumference) when hard, I was amazed to watch her take every bit of it, even more so when I felt her push back against it and moan, I only wish I could’ve lasted longer. Though it was shorter than usual I gave each thrust everything I had. Going harder and harder the more I heard her beg. With one final thrust my cock pulsed as I pumped every single drop of cum inside of her (well, in the condom). Yet somehow she milked it for more, the feeling of her ass squeezing on my cock as she herself came was one of the single most amazing experiences of my life.
We collapsed shortly thereafter. Talking for a few minutes before taking a shower together and ultimately, saying our goodbyes. Though she invited to call again I never did. Sure we chatted from time to time, texting about a new adventure, I never did see her again, and now, probably never will.
Source: reddit.com/r/gonewildstories/comments/fqd6sh/mtf_i_tried_something_new_and_you_know_whati