Articles

Tranny Surprise: First Time Experience

Woman Pulling Man's Tie

Bringing you a hot first-time experience story this week. Enjoy…

I was on a business trip in Phoenix. My wife wanted to come along, but I’d told her she would barely see me as the schedule was tight and she’d be bored stiff. Well, tight and stiff certainly are words to describe my trip.

At the workshop I sat beside Elena. She wore a tight pencil skirt, sheer charcoal stockings, black stilettos, and a pinstripe blouse with just a hint of her lacy bra showing. She wasn’t the kind of woman I normally met on trips, that’s for sure. Her left thigh was brushing against my pant leg. I almost got hard sitting beside her. I definitely wasn’t focused on the presentation.

Meet Local Transwomen at TSmeet.com Now

She was staying on the same floor, right beside mine. I was instantly thinking of doing her. I had only cheated on my wife once, and shit, it took years to repair that damage, so I was only fantasizing, or so I thought. After the meeting, I went to the hotel lounge for a few drinks to cool off, but I ended up back in my room to jack off. I went outside for a smoke and found Elena on the shared balcony.

She’d lost the pantyhose, heels and the blouse. She just had her skirt and a pink camisole on. I didn’t mention, but she had fake boobs, that heaved forward as she spoke. When she asked if I wanted to come through to her room, I obliged. Nothing wrong with a little innocent flirtation, I thought.

We drank make-shift martinis that she concocted from the mini bar. she touched my leg when she laughed, and I could imagine my cock, which was barely under control, sliding in and out of her dripping pussy. I kept thinking about my wife to bring myself back to reality, but Elena was a living breathing babe that was flirting right then, right there. When she leaned over to kiss me (she was a little taller than me and I liked that) her tongue knew exactly what it was doing. My hands were hesitant, but she placed them on her breasts and massaged them around.

She suddenly pulled away and I figured she noticed my wedding ring, but instead she asked me to wait on the balcony while she went inside. She had a surprise. She asked me close my eyes and turn away. I did, obediently. She rubbed up against my back and I could feel something poking at my pants, against my asshole. A dildo! She was kinky, I thought, and it couldn’t get any better than this. I had completely forgotten about my wife at this point. “You’re dirty, Elena,” I moaned, sticking my butt out, my hands on the balcony. I felt like I was in a porno.

She reached around and unbuckled my belt, sliding my pants down. My cock popped out, happy to escape and ready to go. The dildo was wet as it slid between my legs and up through my butt cheeks. I’d never had it in the ass (all the girls I’d slept with were way too prissy). “Oh, god, ya,” I remember saying. I turned around wanting to suck her awesome tits before she initiated me. “Fuck, holy, fuck!” I blurted out when I looked down. It wasn’t a dildo, it was real fucking cock. Her cock? His cock? I froze and felt a little dizzy. I was trying to comprehend what was going on. Okay, those aren’t real tits, but that is one real dick, no strap-on bullshit.

Then I looked at her face – all woman, her legs – all woman. Hell, her whole body was ten times better than what I’d ever laid. She didn’t say anything. That was the weird part. She was waiting for me to react, to decide what to do. My cock was still hard as a rock. I turned back around and bent over the railing. She didn’t hesitate to shove her shaft up my ass and ram me over and over. She pulled out and came all over me. The juice ran down my legs, that were shaking. It was unreal.

I have to admit I don’t remember much after that. I think I was in shock, NO, I know I was. I’ve never told anyone this story, but ever since I’ve had a hard-on for chicks with dicks. And after finding multiple trans dating sites, I know I’m not alone. I’d just rather keep this part of me…

– Anonymous

Want to have your own first-time experience with a trans woman?

Read: Where to Meet Transexuals  or consider our list of the Best Transexual Dating Sites.

Tell us what you think!

guest
4 Comments
Newest
Oldest
Inline Feedbacks
View all comments
Jeff
Jeff
4 months ago

I’d like some feedback if possible. I know the transgender community doesn’t like the term shemale, but I don’t feel the term is meant in a derogatory way. To me, the term transgender or transexual describes a person who is born as one gender but identifies as the other. They, for example, were born male and are in the process of transitioning to female. She may have just started. She may be halfway there, or she may have had elective surgery. Thus the word “trans.” On the other hand, the lady may have started with the intention of completing the… Read more »

trackback
2 years ago

I enjoyed your wonderful blog.

Thank you for the very hard work done.

Jeff
Jeff
3 months ago
Reply to  Ivon Gregory

That you for your response. Now that I’m past that; if I were to date a transgender she wouldn’t be anything short of a lady to me. Her equipment would have nothing to do with it.

trackback
2 years ago

I enjoyed reading your blog.

I want to thank you for the hard work.

To Top