To jump right in this was some time a few years go when Craigslist still had personals. I was pretty young fresh 21 and had been partying with college friends. I usually struck out at college house parties and clubs so I’d end up jacking off on my down time. Every now and then I’d luck out and get some head from a co-worker (F) or the full course. I loved women and never thought I’d be curious to try a transsexual experience.
One weekend I was super horny and I ended up look into the Trans for Male section. Some were the real deal others were men cross dressing and I wasn’t into that. (Not saying anything is wrong with that because it’s cool if you do you).
Long story short I replied to an ad for the hell of it. At first I thought I’d play around get some nudes and jack off for a successful session. However, this idea seemed really curious as I started to think about it. I haven’t felt the touch of someone else in about a month so I was desperate. The ad was for a busty Latina trans women. 7 inch cock and thick. She had black hair and tanned skin with smooth looking skin. She said she was down as she was in town and staying until Monday. It was Saturday night and she was down for some fun. I sent the first nude of my cock rock hard and she was down without a face pic! She asked what I liked and I was curious so I told her I’d try a little bit of everything of the normal. She said she was fine with that.
I pulled up to the hotel and she texts the room number. I’m sweating and nervous and I’m considering just going back to the car and calling this off. I’ve never really randomly rolled up anywhere to meet up with a women for sex yet here I was ready to have a trans women rip my ass open.
She opens the door with nothing but a robe on and hugs me and we exchange greetings. My heart was pound so hard but I was ready. We chat for about 2 minutes and she says, “you ready to get naked?”
I strip down to bare birthday suit and she’s already naked as well. We stand up in front of the bed and start making out kissing passionately. She starts to direct my head to her boobs which are nice C size cups and I sucked on her nipples.
She then takes my head down further and just like that I’m on my knees sucking a cock. My lips wrap around her cock up and down. She lets me suck as I please with just her hand on the back of my head for support.
She then leads me over to the bed where she continues to enjoy my mouth. I felt like I was sucking for hours but it probably was about five minutes. She tells me to get in top and we proceeded to 69. She’s a bit bigger than me in sizes all over. (I was 5’8 and a skinny 130 then).
I continue to suck her cock as she starts taking my cock in her mouth. She stops sucking and starts to eat out my ass hole. A rush of warmth ran though my body and I suck her cock faster and harder. I eventually take her cock out of my mouth and she begins to softly slap my ass with her tongue still on my ass hole.
We finish up oral fun and then, the virgin ass of mine was officially over. She preps a condom on her cock. Thank god she had lube as she sticks her index finger full of it in my ass and finished up the outside rim with more.
At this point I lay down in missionary position and I feel her cock enter in. It was huge, uncomfortable, and my ass was tearing up. She tells me to relax as she’s done this before and can tell my ass is tight. I breathe and take her cock for again what seems like hours. She tells me to flip over and now I’m in dogglestyle position. She slides right in taking my ass as her own. I moan away and she goes faster and faster. At some point my legs give out and now she’s pounding me as only on my belly. I hear a little moan from her and before you know it that was it. She would cum in the condom pull out and take it off.
Since I didn’t get my chance to cum she laid me down on the bed and proceeded to give me head until I cum hard in her mouth. She handled me a towel to wipe my ass and wet cock.
We exchanged satisfaction comments and she said she was headed to a local club which I knew was a gay club. She said she was in town one more night if I was interested in more.
I left and never ever experienced that again. I was fine with that one experience although now I may consider. It’s about 9 years since that experience and I never hooked up with any other genders but a woman from there.
Source: reddit.com/r/gonewildstories/comments/hfp1k7/my_curiosity_for_a_trans_story
> I never hooked up with any other genders but a woman from there.
You also didn’t hook up with any genders other than a woman in this story.