Trans Dating Stories from a Woman

I know, you guys can’t help yourself. You’re always thinking about us getting naked together. I totally get it—I think about girl-on-girl too.

Many friends have asked me whether I date trans girls, and then shamelessly ask me for the dirty deets. So I’ll tell you!

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The first ts girl I dated was a super-skinny, skyscraper-tall woman. She was an artist and the most chic, sophisticated woman I’ve ever known. She was all angles, including the sheet of sleek blonde hair, and chunky designer rings. Her makeup was straight out of European couture, but she could do it with one hand while driving.

I was out of my mind in love with her, but she was twice my age and thought it was wrong to seduce me, even though I begged for it.

We made out like the ship was going down but unfortunately never took off our clothes.

I would have given up everything—even men—for her in a heartbeat, but last I heard, she had married some kind of count and bought a hotel in Dubai.


Julia—otherwise known as Julio—was a gorgeous, bubbly Mexican-American gal with starry eyes, a wide smile, and the sexiest accent ever.

She was a regular at the nightclub I went to. She wore saucy stilettos. When not swapping lip gloss, Julia and I would swap saliva. She liked to straddle my lap and make all the boys crazy horny.

One day I was getting some cash after work, and when I turned around there was this total Latin hunk with curly hair pulled back into a pony, with a soccer player’s body.

He was grinning at me and I thought he thought I was cute.

Then a voice said, “You don’t recognize me, do you, baby?”

It was Julio. I couldn’t believe it. I didn’t know Julia still lived another life—it had never occurred to me. He offered to give me a ride. It was totally surreal, especially since we ended up fucking twice at my place.

I never saw Julio again, but necking with Julia at the club drove me halfway around the bend forever after.


Connie was a quiet, intellectual sort that I met online when looking for a threesome.

She intrigued me because she was so shy, yet had wild fantasies that she was looking to fulfill.

We began to message and talk on the phone. We went out for pints. Connie was into physics and rocket science. She told me a lot about astronomy and computers.

She was far too shy and private to let me get below the belt, but she spoiled me with the only four-hour pussy licking session I’ve ever spread my legs for.

I called her back and left so many messages that it’s no wonder she didn’t call the police. I never saw her again.


I went out with Desiree for six months and we’re still good friends.

She’s a sweet, funny, kind soul and the only reason we broke up is because I’m not ready to settle down.

Desiree was looking for a long-term partnership, not a kinky playmate who was always running off with other girls—and boys too—on the side.

In deep fantasy sessions, she taught me how to focus on nipple sensation and move deeper into my own body that.

Desiree was very spiritual in that way, always quoting Buddhist and Hindu philosophers from India, where she’s from. She made everything sensual, from cooking to working to housecleaning.

As friends today, it’s not even remotely weird that we used to have sex. We were two women with different needs, and she has settled down with a great guy who likes to meditate and make love slowly. I know I’m missing out, but I’m grateful for the gift of friendship.

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