This happened on Sunday, November 2, 2014. So technically, I am not a virgin anymore. But I feel like I still am. Nothing magical happened. Nothing spectacular. I didn’t transform into some experienced guy who is now mature, and is good with women. I’m still the same old nervous, shy, and sensitive guy that I was before sex. But am I still really a virgin?
Okay, so if you remember my I like Trannies blog, the story doesn’t end there. But it continues with this post. I saw this same girl on cl (recognized her body as there was no face pic), and e-mailed her saying what’s up. She was wondering who knows her by name and we connected. After sending her a few pics, she remembered me. We decided to hook up, and went to a place with hot tubs. It’s sort of like a hotel room, but with a little bed and a hot tub. My first time there, but I remember seeing them from porn.
So I get real nervous meeting her for some reason. I’m not sure if maybe we have no connection, or there is such a huge cultural barrier between us, that it’s hard to find a common language. Maybe we just don’t vibe? I don’t know. But the whole time I was nervous, and this isn’t like me usually. I used to be this way before, but nowadays I am more relaxed around people. Was it because she was a woman? Well, technically a Tranny, but a woman in my eyes.
We get to a hot tub, I pay for our private room. And we undress, touching each other. We talk a little bit, and then get in the tub. It was so hot at first, but took me awhile to get used to it. I took a hit from her blunt, so that got me sort of acting weird, and nervous. I freaked her out a little bit when she was touching my cock and I pulled away. Like I was afraid of her having STDs, etc.. Then She says ‘you wanna fuck me?’ I say yeah. I put on a condom, get some lubricant, and she guides my cock into her ass. 3 Strokes and I pulled out because I felt like I was about to cum. That KILLED THE WHOLE VIBE! This girl is fucking BEAUTIFUL, and I’m guessing she isn’t used to guys pulling out so quickly. She sort of got weirded out, asking me why I’m so weird. After talking for a few minutes, she felt bad, and we just got back into it. I was really cautious, and I told her that it’s my problem. I am overly cautious, and she technically is an escort. But she is upscale. Has her website, doesn’t post on cl for her services (outside of hooking up I guess). Her clients are very well off, and not bums off the street. She told me she doesn’t do it that often, and only once a month. I killed the vibe again because I was reluctant to lick her ass. Then she says “how do I know you’re clean?” And even though I told her I NEVER had unprotected sex, she still was technically right, and told me she never had either. How do we both know we’re clean?
So I said fuck it. I am taking a business class right now. And it talks about how if you want to become an entrepreneur at some point in your life, you gotta take risks. There is no way around that. I started jerking her off, playing with her breasts, and the whole time we making out in between talking, and playing around. I told her to get out of the tub and sit on the edge. She was SO FUCKING SEXY! Cinnamon complexion that gets darker around her ass and privates, super clean, smells good, good girl, very cautious around the type of people she is friends with. I think to myself “this isn’t a girl who’d be dirty”. So, I just went with my feeling.
I start licking her ass, and her balls. Then eventually make my way to her asshole and OMFGGGGGGG…. THIS WAS THE BEST PART OF THE SEX! I didn’t even cum because my boner lost Its power when I killed the mood by pulling out. when she started calling me weird, I just couldn’t be that horny anymore. But licking her brown, clean, fresh, soft, tender, juicy ass was the ultimate fantasy I’ve had with Trannies. THIS WAS AMAZING!!!!!!!!! She came in like 3 minutes cuz she said she was really horny. She liked me fingering her ass while I rim it, but that was kinda hard. My tongue was also sore cuz HOT DAYMN IT’S HARD WORK AND WORKS YOUR TONGUE MUSCLES! I thought it was easy from watching it in pornos.
I don’t know, but there is a lot more details I’m leaving out because there is just too much to include. She is looking for a guy to be fwb with, and I’m so open to that. But I just don’t know if we have any connection. It was amazing just holding her and kissing her. My first technical “girlfriend” experience I’ve had with any girl.
The thing that made me think I’m still a virgin, was how short it was. She even let me fuck her hard afterwards but stopped me 30 secs in; said I was hurting her. I don’t know but seems like Trannies are sensitive. But I fucking love them. I don’t think I’d have the same attraction towards women. Too much bad experience, and I feel like there is a block in my mind, or In between me and the female species. Ehhh… who cares. This whole experience was just amazing. Better than the last 2, but so far I’ve yet to enjoy sex by cumming. It’s not the same. It’s not like holding your dick in your hand and squeezing it at the time of the orgasm. When you cum in a girl’s mouth, or her ass-pussy in this case (no homo of course, yes Tranny), it feels weird… It’s like I have no control over how good I feel at the time of the nut.
We’ll see what happens with this girl. But I’m gonna ask her if she wanna get a hotel room next week and spend the entire weekend fooling around together. I really like her. She is honest, even about her being materialistic. But that’s what I like, honesty. And I told her that I’m the same.
Hopefully, there is a part 3 coming soon to this chapter. Stay tuned…
p.s. I kinda feel special, because I taught her what French kiss means. She is taking ESL classes, and so was I when I came to US. Also, she asked me for some help with learning about indigenous cultures, and I was like are you fucking serious? That’s all I fucking know, and study on my own time. Shamanism is the TRUTH that lives in the heart of the Amazon. So, technically I taught her 2 things. The second about ayahuasca, and she already said she wants to drink it. I think we can learn a lot from each other. So, I’m hoping for the best. But you never know. Shit falls apart when you least suspect it to. I digress.