Crossdressing Stories

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Orientation
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Infinite Scroll

A Taste Of Lace

by AdamZasse on Sep 13, 2017
Transsexuals & Crossdressers

By Adam and Evie Zasse The authors would like to extend our thanks to volunteer editor 'Larry in Seattle' for his help in proof reading this story and for his insights and suggestions I've never been into crossdressing. Oh sure I swiped a few pairs of panties from my mom over the years. But they were only something to wrap around my dick when I jerked o...

Giving My First Blowjob

by SLMaid on Sep 16, 2017
Transsexuals & Crossdressers

After a few beers and chicken wings, I left Jim at Gunny's. As I got up to leave I handed him an envelope and told him to give me a half hour then come over to my hotel room. As I left I wondered if he would go through with this. In the envelope was a pair of black nylon full brief panties with a note that said "Put these on before you come over", Sara. Aft...

The Awakening Ch. 04

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

Part Four – Michele Returns The woman is slim. She is wearing a cerise satin blouse, black leather skirt and black high-heeled pumps. Flesh-toned fully-fashioned stockings sheath her long well defined legs. She is wearing a blonde bob, her bangs direct your gaze to heavily madeup eyes, and she's wearing glistening ruby-red lipstick. She is mature but sexy...

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...

Tales of The Great Shift.

by joshman110 on Aug 2, 2019
Fantasy

On a other-wise average day on planet Earth, a strange force of energy passed through the planet. This force was The Great Shift, A supernatural that shifted the minds of 90% of the worlds population into different, random bodies. Say, an 80 year old man is shifted into the hot college co-ed down the street and his old body now has the mind of a twelve year...

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All Inclusive Resort

by Dayeandknight on Sep 26, 2015
Transsexual

Tracy fell back onto the bed, finally able to rest after his ordeal. He worked in an office and he dearly needed a break from the monotony of it all. Cancun, Mexico would be his escape from his life. He worked with a travel agent and got a travel package to his liking and saved what he could for the trip. The airport was a nightmare he thought would never en...

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Boy to Bride Pt. 01 Ch. 01

by sissyscarlet on Jun 19, 2018
Transsexuals & Crossdressers

Part 1: Adam MacDonald Chapter 1: Ms. Alice the Widow Adam carefully shifted the wooden board back in to its place. If only people knew what I kept up there, Adam thought, and smirked to himself. Before he was down from the stepping stool, he looked up at the ceiling 2'x2' entry leading to the attic—an artifact left for insulation and electrical, but Adam...

My Story of Degradation

by Philippasubmaid on Aug 28, 2018
Transsexuals & Crossdressers

A Story of Degradation. This story involves BDSM and crossdressing, change of lifestyle and full submission both mentally and physically. If this is not for you feel free to read elsewhere, please. I was 47, just divorced for the second time and for the first time in years able to be myself and enjoy what I wanted to do in my own time. I should explain...

Disgraced Fiancee

by rik581 on Sep 16, 2017
Transsexuals & Crossdressers

"OMG, Laura please, don't make me do this," Dave pleaded one last time as it was now time to stand before her entire family and beg their forgiveness for his sexual indiscretions. She straightened the dress he was wearing, then adjusted his earrings. "No Dave, the talk is now over. You will perform this embarrassing act for me, and ask my family to forgive...

A Night Drive

by 13feathers on Oct 3, 2018
Transsexuals & Crossdressers

My heart was pounding; my parents had finally, finally, left. On date night, they might be out of the house for four hours, maybe more. It was more than enough time for what I had planned. They were standing by the curb, smiling as I waved to them from the veranda. As they took off and drove, my body quivered with the thought of what I'd do next. The secon...