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  1. #1

    Talking My first time...

    So I've been lurking here awhile and finally opened an account a few weeks ago. Oddly enough, this took place the very next day. I've lost track of the number of TG porn vids I've jerked off to, particularly the variety where she's fucking him. I had always wondered what it would feel like, and a few years back, I had a girlfriend that occasionally enjoyed fucking me with a dildo while she gave me a blowjob. That wasn't enough. I wanted to try the real thing, and I finally got to a few weeks ago...

    Where I live, we don't see too many transsexuals. To the point that I was giving serious consideration to just letting a guy do me so I could see how it feels. I look through the ads on CL, Backpage, etc... every once in awhile in the hopes that a girl shows up, or I look in other cities and let my imagination run wild. Usually when an acceptable girl that I can find reviews on pops up, something makes it not happen. Not enough money, poor timing, I chicken out... You get the idea. This night, a girl named Deseraye showed up, looked amazing in her pictures, had good reviews, timing was right. Everything fell into place. I setup an appointment and headed for her hotel.

    She met me at the door and I'm pretty sure my jaw hit the floor and I started drooling everywhere. She was gorgeous. She was wearing this sexy little dress, and nothing else. Her legs were about a mile long and her skin was so dark I felt like I could fall in. I was nervous as all hell, but she quickly put me at ease. The blowjob probably helped too. She asked me what I wanted to do and I managed to blurt out that I wanted her to fuck me. She smiled and asked if I'd ever been fucked before. I told her I'd never had the real thing yet, just toys. She went back to sucking my cock and I reached over and started stroking hers. She started getting harder, and larger... I started to second guess if this was a good idea or not. I should probably mention at this point that her ad stated she has a 9.5" cock. I didn't have a tape measure handy, but I'm pretty sure she wasn't lying. Probably not the brightest choice when I haven't had anything bigger than a finger up there in well over a year.

    She told me to get on my hands and knees on the bed, and at this point I was pretty sure she had grown to about the proportions of a telephone pole. I watched her slip a condom on that monster and grab a bottle of lube out of the nightstand. She lubed up her fingers and started to loosen me up. Next thing I know, she takes her fingers out and I hear her lube herself up behind me. I felt the bed moving around as she got into position and then I felt the head of her cock on my asshole. She started to put it in and HOLY SHIT, it hurt like hell! I unintentionally yelped and scooted away from her, figuring it wasn't going to work and I had wasted everyone's time. She got something else out of the nightstand. I didn't see what exactly it was, but I soon felt it. It was a dildo of some sort, that started out small and progressively got bigger. She started fucking me with that and damn, did it ever feel good. A little bit later, she asked if I was ready to try again. Naturally I said yes.

    This time, she got it in there. All the way. I couldn't believe it when I felt her bump into my ass cheeks. I reached back and felt around. Sure enough, she was balls deep. I gave them a little squeeze and said, "Okay, let's give it a shot." I lost my anal virginity with style. A BBC belonging to a beautiful t-girl that massaged my prostate with every thrust. Oh, it still hurt, but it also felt so good, I didn't care. All too soon, she told me she was going to cum, then I heard her breathing get heavier and she rammed herself even further inside me than before. Guess she wasn't balls deep after all... I was hoping it would feel like they describe in some of the stories I've read where they say they feel the cock throbbing inside them as they cum, but I didn't get anything like that. Of course, the nerves in my ass were making enough noise of their own that I probably just didn't notice. I kind of collapsed and rolled over on the bed after she pulled out.

    I was laying there enjoying the aftermath with a big ole, shit-eating grin on my face and she asked me if I liked my first time. My answer was something along the lines of "Hell yeah!" Then she said it was my turn. She put a condom on me and assumed the position. I tried to put it in, but my dick just wasn't cooperating with us, so she took the condom off of me, lubed up her hand and gave me the best handjob I've ever experienced. I couldn't believe the amount of cum that came out of me. I was almost embarrassed. And it was all over her, the wall, the bed... Oops. It felt like the whole experience was over in no time at all, but when I got back out to my car and looked at the clock, I realized I had been in there for well over an hour.

    So yeah, three weeks later and I still get a grin every time I think about that. I can't wait for the opportunity to present itself again.


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  2. #2
    Senior Member Veteran Poster daBXitalian's Avatar
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    Default Re: My first time...

    Good story



  3. #3
    Rookie Poster
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    Default Re: My first time...

    Fantastic, thanks for sharing



  4. #4
    Junior Member Rookie Poster
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    Default Re: My first time...

    Awesome story! I wish my first time story went like this. My first experience was pretty bad



  5. #5
    Greatest Member euro4ts's Avatar
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    Default Re: My first time...

    Why was it bad?



  6. #6
    Rookie Poster holyshit's Avatar
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    Default Re: My first time...

    Sound like my first, except for the sex part. My first was kinda bad but my second were a lot better.



  7. #7
    Junior Member Rookie Poster
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    Default Re: My first time...

    I'm jealous as hell of this!! That sounds like a life changing experience!! Lucky!!



  8. #8
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    Quote Originally Posted by Andyg125 View Post
    I'm jealous as hell of this!! That sounds like a life changing experience!! Lucky!!
    Yes. Thats what Id do too.But only for starters!



  9. #9
    Junior Member Rookie Poster
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    Default Re: My first time...

    Great story. She sounds like a great woman to have your first-time experience with. Well written as well.



  10. #10

    Default Re: My first time...

    What city did this happen in? I want to meet this girl!



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