(M)y second time with a (T)rans girl

This is a follow-up to my first story. Still a true story, so I apologize in advance if something is less than sensational. This one is a bit longer though.

I left my friend's birthday party in a fog. I had just had the most amazing sexual experience with a trans girl I had met at the party. It was something so unexpected, both for the fact that it happened and because I had never thought of doing anything like that before. Don't get me wrong…I had no hangups about it. No regrets or anything like that. I was just in this stupor from how awesome it was.

I went home that night and couldn't keep the night from replaying over and over in my head. And yeah, I rubbed one out thinking about it. I was still so hot over the situation.

Before we left the party, I got Claudia's number. I definitely wanted to see her again, but also was trying to play it a little cool by giving it a day or two before calling her. The party was on a Saturday and by Tuesday, I couldn't wait any longer and gave her a call. It was a bit awkward because I was thinking the whole time "hey, you remember Saturday when we banged like there was no tomorrow? Yeah, I want to do that again." To her credit, she was really easy to talk to and seemed eager to meet up again.

We agreed to meet for drinks that Friday afternoon. I picked a low-key outdoor bar close to my place. Somewhere we could hang out and chat, and somewhere close enough to get back to my place quickly if things progressed.

I showed up first and got a table. She arrived shortly after me. This was the first time I had seen her outside of any form of inebriation, and she was just as stunning as I remember. She was dressed simply in a tight tank top, tight jeans, and fashionable sandals. Her hair was up in a ponytail and she had on very light makeup. She did have on this rather bold lipstick. It was the same shade of red as her nails.

She smiled as she sat down and kind of exhaled. I asked her if everything was ok ad she replied "yeah, I just always get nervous that a guy I like might get second thoughts once the excitement of the night wears off. I always expect to be stood-up or to have the 'look, we had fun, but…' conversation. I was just relieved you showed up and was checking me out as I walked over."

Having that out of the way, we had a few drinks and talked about school wrapping up, our next plans, and of course, her background. I didn't come right out and ask, but she seemed open to talk about it and I wanted to learn about her.

She told me she had been living as a woman full-time for about five years now, having transitioned in high school. Her family was supportive, but relationships had been difficult. She then point blank asks me why I am OK with her like she is. I'm sure I stuttered out my answer, but I explained that until she showed me her body, I had no idea. My thought on the matter was, here is this really attractive person who is obviously into me, good personality, and wanted to have some fun. I had never thought of pursuing someone like her, but also had no objection to it. Ultimately, she looked like a girl, acted like a girl, and in her mind was a girl…good enough for me.

She seemed to like that answer and the conversation eased up a bit. We had a few more drinks and the topic inevitably turned to sex. I admitted that, while I was totally cool with everything that had happened, it was all new and I was woefully inexperienced in pleasuring someone like her. She reassured me that I did quite well for my first time and asked me how I liked it. I replied "I loved it. Being completely new to me, it was like a sensory overload." She assumed, but asked anyway, that I had never sucked a cock before. Blushing, I replied, nope, first time. She said "well, you were really good at it. With a little practice you would be an excellent cocksucker." Did she really just say that in public?

I about spit out my drink. I'm sure I was five shades of red, but I mumbled out, "thanks." I told her it was really nice playing with a cock that wasn't my own and I hoped to get more time to learn. She got a little quiet and asked, "is there anything else you are curious about?" I gave a very non-committal answer like, "I'm curious about being with you again, seeing what else there is."

She seized this opportunity and asked me if I would consider letting her fuck me. Now, I figured if we got together again that this may come up. I knew not all trans girls like to do that, but it was always a possibility. To be honest, I had gone that far already, I figured, why not?

I told her "that's something I would consider, but you would have to really earn it." She smirked, raised her hand,and called for the check. I'm thinking to myself, "damn, this girl wants to fuck my ass so bad she just picked up a decent bar bill to convince me. What did I get myself into?"

I walked her back to my car and told her if she wanted to, I could driver her back to my place, since it was close, and we could get her car later. She responded by stepping in front of me and giving me a very erotic, tongue-heavy kiss. I had that unique taste of lipstick on my lips and it lit a fire in me. I kind of shook my head in awe…we were going back to my place and I was about to get my ass fucked.

It was a short drive home and she had her hand on my crotch the whole way. Her manicured nails rubbing, teasing, playing with my cock through my jeans. I had to pull her hand off once because I was getting a little too excited.

We get back to my place and, once again, as soon as the door is closed, we are all over each other. We move directly to my bedroom and begin undressing each other. I take her tank top off and she removes my shirt. She is wearing this little lacy bra that makes her tits look unbelievable, but it comes off as well pretty quickly. We move in to each other and our hands find their ways to each other's pants. She is stroking the front of my jeans and I am doing the same to hers. I can feel her responding to my touch. It was strange but really hot. I could feel her cock twitch and slowly grow in her pants. I'm rock hard at this point and want nothing more than to get this going, so I slowly back her up to my bed and start unbuttoning her jeans. I wiggle them down over her hips and see the product of my efforts…her engorged cock struggling to escape her panties.

I told her she got to take the lead at the party, but today it was my turn. She was half-sitting, half-leaning on the end of my bed as I kissed my way down her body. As I got to her panties, I licked the outline of her cock in her panties a few times before sliding them over her boner and down her body. Once they were off, I looked up and all I could see at the top of her thighs was cock and balls. I licked the inside of her thigh on my way back up, and then gently took one of her balls in my mouth. It was so smooth and soft, I couldn't believe it. I switched to her other ball then ran my tongue up the length of her cock before taking it in my mouth.

I must have been doing something right because she is white-knuckling the edge of my bed. She also starts to get verbal, telling me "suck me, suck my cock." She is looking down at me and says "yeah baby, suck my cock. You need to get it hard and wet so I can fuck you." This is driving me wild and I'm sucking her for all I'm worth. After a couple minutes she pulls me up to make out some and then rolls me over onto the bed. It's her turn.

She unbuttons my pants and has them off of me in no time. Underwear comes off with them. I'm still hard and she asks me if sucking her cock gets me hard. I tell her "you have no idea." She doesn't waste any time and takes me in her mouth. It's still a great blowjob, but I can tell she has more on her mind. She has me scoot up a little on the end of my bed so that my butt is on the edge where my feet can't touch the ground. She has me lean up an sticks her index finger in my mouth. She tells me to get it good an wet so it doesn't hurt. I'm thiking, "oh shit, here we go."

After a couple of seconds of fellating her finger, she pushes my chest back so I will lay my back down on the bed. She goes back to work on my cock and starts teasing my asshole with her finger. Then, without a hint of hesitation, goes all the way down on my cock while sliding her finger in my ass. Having had nothing up there before, I'm surprised that there was little discomfort. She gave me a couple seconds to adjust then starts working my cock and ass at the same time. I don't know what came over me, but I start bucking into her finger. Man, this feels good.

She stops for a moment and looks around. She tells me to wait a second and hops up and bounces out of my room. She is only gone for a moment, though, to get her purse she had dropped by the front door. I watch her walk back in the room, her hard cock bobbing with her steps, and I just smile. She sees me smiling and asks if I'm sure I want to do this. There is literally nothing that would have stopped me at that point.

So she gets out her lube and a couple of condoms and tosses them on the bed next to me. She opens the lube bottle and squirts some in her hand. She takes the finger that has already been exploring, and the one next to it, and starts rubbing my hole with this twisting motion. Each twist adds a more and more pressure until she has two fingers inside me. She fingers me like this for a bit and all of a sudden I blurt out, "i need you to fuck me."

She giggles and backs up, grabbing her cock, and asks me "is this what you want?" She leans back in and tells me to get her ready. I waste no time in getting off the bed, on my knees, and put her cock back in my mouth. I bob back and forth on her cock for a while when she bumps my shoulder to hand me a condom. I open the condom and roll it onto her dick, the whole time thinking, what a different situation. Anyway, I tug on her cock a couple of times and she motions for me to get on my knees on the bed. I climb up and feel the bed shift under her weight when she joins behind me. She takes some more lube and spreads it on her cock and my ass and just kind of leans in. I can feel her cock at my hole, pushing ever so slowly in. This part hurt a bit, but I'm still into it. She can sense my pain and tells me to push like I am trying to poop. The moment I start to do that she slides in. I think I actually said "holy shit, you're all the way in."

She laughs but isn't going to let me rest. She starts sliding in and out with short, slow strokes at first then starts with longer, harder strokes shortly thereafter. It feels amazing. Actually, too amazing. I'd like to say we fucked in a bunch of different positions but after a couple of minutes I feel the most urgent orgasm I have ever had boiling to the surface. She takes an exceptionally long stroke and I cum the life out of me. I'm so spent I have to have her stop. I know all she wants to do at this point is to get off, but I can't move for a moment.

Once I come around, I lay her down on the bed, take the condom off her cock, and put it back in my mouth. She is still pretty hard from fucking me, so it doesn't take long to get her revved up again. As I am sucking I can feel her cock getting firmer and bigger in my mouth. Before she can warn me she is about to cum she unloads in my mouth. She must have been saving up in hopes this day turned out well because she came a lot. I had to swallow twice to get all of it down. I'm also proud to say I swallowed without any hesitation. And I have to say, it tasted pretty good. Maybe it was just the hotness of the situation, but it really did taste good.

It was rather late after our antics and she asked if she could stay over. I agreed as long as she would hang out in the morning and teach me other things. That is for another time and is, unfortunately, the last time we were together.

Source: reddit.com/r/gonewildstories/comments/3zsfau/my_second_time_with_a_trans_girl

11 comments

  1. Can’t wait to read more! This was so good and I became so invested in the two of you that I was sad to read that there was only one more encounter… What happened?

  2. This all happened the summer we graduated college. She got a job in New Orleans and I headed to D.C. for grad school. Without Facebook or anything like it we just lost touch.

  3. Great story, that’s a shame this was the last time. Your last experience too?

  4. It was my last time with a trans person. I’ve had a few mm experiences since then…may get around to write about those.

  5. I don’t understand? You said the same thing on his part 1 story. The title is very clear on what is involved in this story, so don’t read it, If it’s not your thing. Why bring so much hate on the world.

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