Crossdressing Sex Stories

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Orientation
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Infinite Scroll

Home in the Hills Pt. 01

by ValoryG on Dec 10, 2019
Transgender & Crossdressers

All names and characters in this story are fictional and have no connection with any actual person living or dead. ***** Jonathon Worley is in his sophomore year at Onanoma State University, majoring - at least for the time being - in art history. He's the third child in his family, and after his parents paid for the first two to go to college, there was...

The Marriage of Martin Hastings Ch. 17

by rik581 on Sep 14, 2017
Transsexuals & Crossdressers

Martin sat alone in a small interrogation room. The large wood table with the two empty chairs on the opposite side of the table were all the furnishings in the room. The humiliation Martin had suffered as he was brought through the police station, the giggles, sneers and staring were still fresh in his mind. Though he was told he was not under arrest, he fe...

My Wife Cheated, But I Liked It

by Jackb120 on May 6, 2019
Interracial Love

I've always been the average guy. I'm into normal things like working out, watching TV, and drinking beer with my friends. That said, I was shown porn as a teenager and found myself into interracial cuckolding and even crossdressing before I had my first real girlfriend. After highschool I moved away from home and stopped the crossdressing but kept the porn...

My Babysitter Ch. 02

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

There it was again. That hard, warm cock in my mouth. I loved it. I needed it. I knew it wouldn't last, though. I awoke from my dream with my hands on my dick as usual, but my mom was standing by my bed. I was so surprised to see her standing over the bed I almost forgot to conceal my erection. "Hey son we're home from our trip to Hawaii!" she beamed. "Oh...

Adventures after Dark Ch. 01

by classmate1119 on Sep 16, 2017
Transsexuals & Crossdressers

-Author's note- I started crossdressing in my teens, but coming from conservative South-east Asia, it was definitely my darkest secret for many years. I would often dress in my mother's dresses, and put on her makeup when I was home alone, but I stopped crossdressing when I moved away to start college. When I won a scholarship to study in the UK, I did no...

Kasey's Legs

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

I had been crossdressing for close to ten years. It started as a Halloween costume gag where I shaved my legs, put on a cheerleader outfit and wore a scary mask. After I kept getting compliments on how good my legs looked I continued shaving them and experimenting with dressing in a variety of women's outfits, skirts, high heeled shoes, panties and bras. It...

Mistress Chantel, Tranny Dominatrix Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Prefix: Welcome to my next erotic story. This story will be written from the point of view of a Transvestite Dominatrix. It is a new twist in my mindset as I normally identify as submissive and as a sissy maid and slut to a dominant Master. It's my 'kink' but I have danced around in my mind a story from a position of Chantel being a true Transvestite Dominat...

How I was Forced Out of the Closet

by gtanya on Apr 4, 2018
Transsexuals & Crossdressers

I was again dreaming of the night I would lose my anal virginity. It had been such a constant since last 3 weeks. I had been talking to a beautiful CD named Rachel since last 6 months and with the thought of meeting her in person, I had planned a vacation to China where she was living. The only problem that I had here was I was going to be on the vacation wi...

Ash's Metamorphosis

by Katnaace on Aug 6, 2019
Fan Fiction

Ash took a deep breath. For as good as life had been for the trainer, things were starting to become... stale. It felt as if he was stuck in a loop of sorts, unable to break free no matter what he did. "I just want a change." he thought, laying down in his bed. Sleep came quickly, with him unaware of what would await him come tomorrow.What's next?...

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Sex therapist

by qaz on Sep 1, 2016
Miscellaneous

Who do we follow?What's next? A boy A girl What's next? A boy A girl...

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