First time with a trans girl

An old romance from my younger days, but one I tend to think about as we move into the colder weather. My friend was going to a small college a few hours away and invited me out to their Fall Fest. He lived in a big house off campus with a bunch of other students. They were hosting a pre-party before the actual Fall Fest, and that’s where I met Sara. She was pretty, almost waifish, and dressed in a style that we would have called alternative at the time, a short skirt, fishnet stockings, and black boots. She was there visiting her friend and we just hit it off.

A fun day of partying ensued and I ended up running into her in a bar later that night. I slid into the booth next to her and we recounted the day’s adventures. We were definitely getting cozy sitting there talking, at a certain point she leans in and says, “you know I’m trans, right?” and after what was probably a long pause added, “I just didn’t want you to be mad” I leaned over and gave her a big hug and that seemed to make her happy.

We walked back to the house and I go to a spare room to crash, thinking the evening was over. A couple minutes later, Sara knocks on the door and asks if she can sleep there, someone had snagged her spot in another room. She offers to sleep on the couch but I wave her into the bed. I see her kick her boots off and slide down her stockings

She climbs into bed, we’re both laying on our sides talking. After a few minutes she says, “you can kiss me if you want” and without any hesitation, I do. As we’re making out, I begin to run my hand up her leg, starting to go under her skirt. She stops me and gets up on her knees in bed. She lifts up her skirt to show her small, erect penis. “No surprises? I told you I was trans” I assured her it was ok and pulled down my boxers, showing my considerably larger dick, also quite hard.

She gets out of bed to take her skirt off, and I can hear her rustling around. She gets back in bed right on top of me and starts grinding into me as we kiss. I begin groping her ass and realize she’s put lube on herself. I rub a finger around and gently push it in. She lets out a little sigh and continues to grind away.

After a few minutes of this, she slides forward a bit and reaches around to grab my dick and guides it into her ass. She slowly rides me for a few minutes, my dick sliding deeper as she picks up the pace. I hear her begin to start breathing heavy and with a sudden gasp, I feel her cum on my stomach. She rode me a little more until I came in her.

She fell asleep in my arms, me still swooning a bit. We said our goodbyes the next day, hoping we would stay in touch