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

(This is a true story and also my first attempt at writing. Hope you enjoy)

This happened back in college at the 21st birthday of an acquaintance of mine. My friend Josh was a pretty cool guy, lived in a decent sized house off campus, and loved to throw parties. Josh also happened to be gay as were most of the attendees at the party. I had hung out with him before and knew what his party scene was like. Although I was straight none of his antics never bothered me or made me feel uncomfortable. The same cannot be said about his roommate.

The party got started about 9 o'clock and there were probably 30 to 40 people in the house. Josh's roommate was there and was already drunk by the time I got there. His normal aggressive manners were on full force thanks to the alcohol. I had come in from the patio to get another drink and the roommate corners me by the drink table. He basically pushes me into the table, grabbing at my crotch, and tries to kiss me. Now, I'm not homophobic in any way, but I can't stand this type of aggressive behavior from people.

As this is going on a girl comes over to the table and tries to get the roommate to back off. From what I could tell, this girl knew him and had seen this before. She successfully redirects him to another group of people outside and comes back to the drink table to apologize for his behavior.

Even with everything going on I can't help but notice how cute this girl is. She is about 5'7", brunette, and is wearing a pink maxi dress that shows off her obviously fake, but fantastic tits. I'm immediately smitten. She introduces herself as Claudia and I mumble out my name in return. We start chatting about what just happened and eventually get to the point where I can laugh about it.

As we were talking she gets around to asking "so, outside of the rapey vibe, did it get you excited at all?" I replied "yeah, I mean, as long as I'm not being assaulted, anyone rubbing my dick feels great." She asks if I cared it was a guy rubbing me and I said "no, a hand is a hand." She kinda smirks and says "interesting."

We mingle around the party a while and go outside to partake in a joint that is being passed around. After getting sufficiently lit, she takes my hand and walks me back into the house, down the hallway, and into an open bedroom. She is leading the way and I'm intently watching her ass sway in her dress.

As soon as she closes the door we are making out. My hands are all over her body and are drawn to her ass like a magnet. After making out a little bit she slips to her knees and starts unbuckling my belt and opening my pants. As her well-mannered fingers rub and stroke my cock through my underwear, she asks "are these hands ok?" Before I can respond she is tugging my underwear down over my impossibly hard cock and slips it in her mouth. She is both tender and relentless at the same time. This is by far the best blowjob of my life. As she is going to town on my cock she hooks her thumbs in the top of her dress and kind of just shimmies out of it. I reach over her and unhook her bra and I am staring at a beautiful set of what I would guess are a full c-cup.

After blowing me for a while I have to pull her up off of her knees so I don't cum yet. She stands back up, her hand never leaving my cock, and we start making out again. We are kissing, she is stroking me, and I am in heaven. I can't wait to fuck her so I reach down between her legs to get her going a little. As I touch the front of her panties I immediately feel an unmistakable bulge. I pull my hand back a bit from sheer surprise. I would never have guessed. She looks at me, smiles, and says "a hand is a hand, right?" She moves a little and slips out of her panties. She then takes my hand and puts it on her bare cock. She is already semi-hard and I begin to stroke her as best as I can.

Having never stroked another cock, especially one facing you, I was a bit awkward. Sensing me fumbling a bit, she reaches down, takes both of our cocks in her hand, and begins stroking them together. This is a completely new, super hot experience and I once again have to back off to keep from cumming. Not wanting to kill the mood, I do the only thing I can think of doing at that moment to keep her excited and into this…I slip down to my knees. She starts to say "you don't have to…" but I'm already licking the side and underside of her cock. I have no idea what I am doing, can't believe I'm doing it, but I am so hot for her I just put her cock in my mouth and do what I think would feel good. I guess I was ok because she is panting "oh shit, oh shit", grabbing the hair on the back of my head, and pulling me down deeper.

After a couple of minutes she pulls me off of her and up on my feet. She says "I need you to fuck me, NOW." She grabs a condom from her purse and tosses it to me. As I am rapidly putting on the condom, she is rubbing her fingers over her hole. I didn't even see her grab lube but that is obviously what she is doing. She kisses me again, leans over the end of the bed and begs me to fuck her.

I slip in without as much effort as I anticipated, but God was she tight. We start fucking with abandon. She's moaning loud and now is the first time I remember we are at a house party. I think to keep a little quieter, but this girl is not going to be denied. I'd like to say we banged all night, but with this sensory overload, I don't last very long. Before I know it I'm coming hard into the condom. I pull out and she rolls over frantically telling me she's close. She grabs my hand and puts it back on her cock, guiding my hand to stroke her. Seconds later she is cumming all over our hands.

After we calm down and collect ourselves, we get dressed to rejoin the party. We run into one of Josh's friends that I know and I'm sure he could tell what we had just done. I couldn't care less. It really was one of the best moments in my life.

I got Claudia's number and we did get together one other time, but things didn't really progress from there. We were both graduating in a month and were moving away from that town so the timing was shit. I wish I could have explored that relationship more, but so is life.

Source: reddit.com/r/gonewildstories/comments/3zf18g/my_first_time_with_a_trans_girl

49 comments

  4. We don’t have better words to describe the multiaxis space of gender. That’s not a proscription on reality. It’s a failure of our language to describe reality. Until language catches up, a polite person uses the word the subject wants.

  5. DNA and biology determine gender, not the "feels". GET THE MEMO. It’s not "fluid", subject to "debate" or "interpretation" by half-wits and simpletons. You may not believe in Newtonian Physics but the facts don’t care if you believe them or not, as they’re still true. Grow up.

  6. It’s actually pretty simple. Sex does not equal gender. So yes biologically male. But a woman in mannerisms and mind.

  7. There’s some delicious irony with someone telling a bunch of people to "grow up" for not being bigoted and hateful enough.

  8. Who are you quoting there? Some demon that haunts you? Kudos! Newtonian physics is a perfect analog for static binary-genders. It’s good enough for a lot of cases, but it’s terribly flawed on the fringes. The computer in front of you is prone (and relies on) physics that fail at its small scales, and the GPS in the phone you’re holding relies on other ways Newton’s physics fails (in two different ways!) at fast and gravitation-affected frames. The failure of Newtonian physics is a splendid example. Thank you. Facts are not words and words do not define reality. Language lags behind our understanding.

  9. You poor, delusional, uneducated, histrionic, irrational, logically/intellectually/factually challenged rube. You’re ridiculous. Interesting posting history. I should’ve know you were one of "those". Lol Please start posting after you finish high school, get a job, lose a lot of weight and your virginity. :)

  10. I suggest you lose your virginity, get an education, get a job and lose some weight before you post again and remove all doubt as to how much of a ridiculous fool you are. PS: Amusing posting history. You wear the confused neck beard well.

  11. Hah! Too good! Thanks for that. Are you ever scared or sad the only mark you’re making in the world is your comment history? It’s not even a good mark, is it?

  12. Honey, when you write terrible fiction for sale on amazon because of your, obvious, sexual frustrations you really need to get a life. You don’t know WTF you’re talking about and I’ll happily compare my educational background, CV, balance sheet and accomplishments with an obvious failure, like you. :) PS: You really are a terrible writer and unemployed. Enjoy poverty.

  16. Good to know? Thanks for reaffirming what we were all thinking about you. It’s ok.

  21. This is a huge fantasy of mine, not much literature on it though, thanks I realllly enjoyed this. Would love to hear the second part more detailed and longer too!

  22. Thank you. This was my very first attempt at writing this down. I will work on detail for the second part.

  23. Wow, this is a fantasy of mine, you’re a lucky man. Should of let her fuck you too ;)

  27. The only simpletons who write ridiculous shit like that are: weaboos (you’re obviously one), fat people, the uneducated, the unemployed and losers. It’s a safe bet that all apply to you.

  28. Haha bro if you dig into my post history you’d know I’m not any of those things. Good job repeating the same thing over and over to different people in this thread though, you sound A+ sane and stable and like an all around cool guy, we’re all very impressed (obviously).

  33. No. There is something wrong with someone who, through DNA and biology, is one sex while "proclaiming" they’re another. It’s ridiculous. Stop being an idiot and develop some reading comprehension.

  34. While your other comments do paint the picture of you being an insufferable twat, I can’t disagree with your point here. I too disagree with having society decide gender over genetics. The biological makeup doesn’t change, and stating it does just seems like an exercise to further drive us apart, and create more biases and ways to discriminate.

  36. Confirmed: You’re a loser. Just be the fat, neck beard loser that you are. It’s rather amusing when grown men have roommates.

  37. Hahahaha. I only hear that kind of shit people who frequent Tumble, and use the phrase "shitlord". It’s quite entertaining actually. Do tell, what else is wrong with me? Do I lose at life? Will I never be able to please a woman? Will I never earn the respect of my peers? Or should I go with a different canned insult that was written by somebody else in a different post?

  41. He really does. I don’t think he even read that I was partially agreeing with him. Considering that, I’m pretty sure he/she is just an internet troll, and this is about all he has going on.

  42. S/he does not have negative Karma so obviously s/he is not successful at being a troll.

  48. I’m straight, but passable shemales are one of my turn ons. Literally a woman with a cock. I would definitely have done it, too. Sounds like a blast!

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