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Thread: My First Time

  1. #1
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    Default My First Time

    So this story is 100% true and going on my best recollection. This ended up being way longer than I thought it would be and honestly I was writing more for me to relive it than for entertainment purposes so, sorry if its a little long winded.


    Alright just to paint a little picture here, I'll give a couple details: This was a few years back- I was 21 or 22 years old at the time. I was your typical fit, young, white, college guy (like 5'11, 180). I had been curious about transexuals for at least 2 years just from watching porn and had really developed a desire to hook up with one. So I set up an account on adult friend finder and started searching.

    I found a really hot girl that I had started sending messages back and forth to. She was the same age as me. She was Polynesian, she had long slender/toned legs, a real tight stomach (really fit- not an ounce of fat), a cute face, long black hair and of course, nice tan skin. She must have been 5'10 or 5'11 because I remember she was just a little taller than me when she had her heels on.

    So I had been looking at her pictures and imagining what it would be like to actually hook up with a transexual girl.. Would she look different than her pictures? Would it just be too weird? What would it be like to actually suck her dick? Was this all just a fantasy? Should I even do it?

    Well one weekend night during the summer I had gone out drinking and was walking back to my house when I decided to send her a message. She sent one back saying she was at a party in the city where she lived, which was about an hour and a half from where I lived. I had a couple drinks in me (nothing crazy) and I finally had the nerve to ask her if I could come down and hangout with her, nothing sexually explicit, just asking if I could down to where she was. She said yes and gave me her address, I got in my car and drove down. The drive felt like it was taking forever- the anticipation was killing me, I couldn't wait to see this girl in person. I had literally been looking at her pictures for like 3 months.

    I remember pulling up to the house party and texting her, telling her I was there and I'd be waiting by my car. It took a couple minutes of waiting but I saw her walk out of the door and out towards the front lawn. It was crazy seeing her walking out of the house and towards me. It was like seeing a celebrity in person- someone you've seen so many times in pictures but it was just so different to see them in real life. I remember she was so much taller than I expected. She was wearing a pink crop top that showed her abs, tight blue jeans, and black heels. She came walking with her friend and when they were close enough I got out of my car, walked up to her and said Hi, we gave each other a hug. I remember as I hugged her I could feel her bare back, it was so smooth and soft but it definitely felt more muscular than your average genetic girl. This was my first time ever seeing or touching a transgender girl in real life, after fantasizing about it for over 2 years so I was really taking it all in. I remember her friend saying, "Oh your guy is cute!". Which was awesome to hear.

    So she walks me into the house. It was kinda weird because it was dark and there was just loud rap booming from the speakers and there were a ton of big tough Samoan dudes everywhere. I think I might have been the only white guy there. But everyone was having a good time partying so I just went with it. She asked me if I wanted a beer and I said yes. She handed me a beer from the fridge and got one for herself. I remember she asked me to open her bottle for her in a really light feminine voice. When she handed me the bottle I noticed how big her hands were, which was not a turn-off at all- I actually like t-girls who are a little androgynous. It was so hot to have this girl with such a light pretty voice and looked so feminine who was also a little taller than me and probably had hands as big as mine. She talked very softly, almost to the point that it was hard to hear but she was really sweet and laid back.

    I can't remember how long we hung out in the living room but eventually she walked me back to this room down the hallway. I remember the room was kinda dark and there was a little bed in the corner, we closed the door behind us and all you could hear was the bass from the music in the living room.

    This is when one of the hottest sexual experiences of my life started. I remember I sat on the bed and took a sip of my beer- not sure how fast or far she was willing to go... My question was quickly answered. Without saying anything she unbuttoned her pants and pulled them down, revealing her long slender legs. It was so fucking hot- she had on black lace booty shorts for underwear. I could see her profile as she pulled her pants off and the two things I'll always remember are her nice little ass- there's just something unique about a really in-shape young tranny's ass. It doesn't quite look like a genetic girls ass, it's a little more petite. The other thing was what I'd been fantasizing about for so long- a nice big bulge in the front her little panties. Seriously one of the hottest things you'll ever see in person- anyone who's been with a transgender girl knows what I mean.

    She lays down on the bed with me, wearing her pink crop top and black panties. We start making out, dry humping, grinding- I'm trying to run my hands over every section of her body... It was amazing. I took her shirt off and I sucked on her nipples, which just had the slightest little boobs underneath them. Eventually I pull her panties off to reveal a nice, hard, tan, 6-inch (guessing), circumcised cock. Being (what I would consider), a totally straight, 'normal' guy, it was so hot to be staring at a cock just inches away from me- that wasn't totally masculine but actually seemed feminine. I brought my head down to her cock and started sucking.... I remember thinking, 'This was the moment, this was it, there was no turning back from here, I'm officially hooking up with a tranny'. It was amazing, it felt so good in my mouth, it tasted good, it felt good to hear her moaning, it was fun! I remember sucking it for a little and then telling her, "I've never done this before". She giggled and told me to keep going.

    Eventually we're both naked, both hard, and both ready to fuck. She had a condom and lube with her. She gave me the condom to put on and she put a little dab of lube on her ass. She laid on her back and put her long legs up. (Now I had had anal sex with the girl I had dated prior to this hookup, and it was always a little disappointing because I'd have to go really slow and ease it in and she would try to enjoy it but I could tell she wasn't really into it.) So I was prepared to gently ease my cock into her ass and for it to be a little tight and awkward at first. But holy shit my cock just slipped right in, there was no easing it in, no loosening it up. I was able to just fuck her as hard as I wanted, she didn't even flinch. I can't even remember fingering her before I put my cock in. Anyway, I made the most of it. I fucked her missionary, doggy, she went cowgirl.. everything I could think of.

    I swear I'm not making any of this up. I don't know why or how but I eventually pull my dick out and take the condom off so she can finish me off with her mouth. She was laying on her back, legs spread wide open, jacking off her cock. And I'm next to her head on my knees as she's sucking. I ask, "Can I cum." (I had no idea if she was cool with me cumming her mouth.) She immediately said, "YES." I start jacking off into her mouth while she's jacking her self off. I cum in her mouth and a minute later she makes herself cum.

    We ended up laying around for awhile, cuddling and talking. Eventually I decide to leave and she walks me to my car, we hug and kiss and I go on my way. I've never seen her again to this day, I deleted my aff account a long time ago, lost her number at some point, I can't find her when I go looking around on-line, but I do often think about that night... Anyway, it was definitely one of my favorite sexual experiences of all time.

    Since then I've hooked up with about 10 other t-girls and I'll write about those experiences if anyones interested. Most of them have been really fun.


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  2. #2
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    Default Re: My First Time

    Man that sounds like an amazing did experience. Did you think of letting her mount you?



  3. #3
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    Default Re: My First Time

    Thanks for the well written summary! I'd enjoy reading about any or all of the rest of your experiences you'd like to share... as I'm sure many others here would as well.



  4. #4
    Junior Member Rookie Poster
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    Default Re: My First Time

    Thanks and nah I'm definitely a top and she was definitely a bottom.



  5. #5
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    Default Re: My First Time

    Very sexy experience, lucky man keep it up lol.



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