Crossdressed Stories

155 results
Orientation
Length
Source
Infinite Scroll

Dormitory Fire Drill

by Lia Monde on Sep 13, 2017
Transsexuals & Crossdressers

The bed in Beverly's dorm room was narrow. It forced their naked bodies close. That was fine with Les, it increased the intimacy. As they spooned together, Les's arm draped across her waist and fondled the bottom of her left breast. His face pressed into the hair at her neck and inhaled the wonderful aroma. His erect penis rested in the crack of her ass. Be...

Life and Time of Lady Vargos Ch. 10

by rik581 on Mar 25, 2019
Transgender & Crossdressers

Chapter Ten "The Vow and Portrait Ceremony" It would be a night to remember for the guest that were arriving at the manor and a night Martin would never forget. Martin sat in a comfortable chair with his hands on the arms, his legs crossed as he listened to Phoebe's questions. The only other person in the room was the photographer, who had already snappe...

Sleeping Beauties Ch. 01

by MicheleNylons on Dec 2, 2019
Transgender & Crossdressers

Chapter One - The Bride Wore White Author's Note: Penelope Bishop first appeared in my story 'Cop Town Girl'. This saga stands on its own but if you want to read about Penelope's past, the story is available for your perusal. I hope you enjoy this thriller. ***** Penelope Bishop woke up to the ringing of her cell phone, her head groggy; to her it sounded...

A New Day Dawning

by Gratefilled1 on Oct 6, 2020
Transgender & Crossdressers

When I heard that Jeff was going to spend the summer at home this year I was thrilled. It had been a few years since my son and I had been able to spend this much time together. He was finishing his third year of college on the west coast and we hadn't really had the money for a lot of visits to see each other, and when we did they were brief and busy. To be...

My Metaphor

by hyperpress on Dec 24, 2018
Fetish

The audience drops into a continuing story written in first person POV (mostly). The following based on a true story. Given enough time, any question that occurs to the reader shall be answered, eventually. * I woke the next day, showered, put on a comfortable chemise, a microfiber and nylon blend thong and open toed sandals, made some coffee and sat down...

Whores And Pimps Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

Malcolm was a middle manager in a small business in a large city. Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm had a few girlfriends over the years but never anything serio...

Indoctrination

by cuck4Traci on Sep 25, 2017
Loving Wives

I must have dozed off at some point. The sound of my wife coming home woke me up, the front door opening, closing, and the dead bolt locking. Happily, I heard my wife's angelic voice, oddly though it sounded as if she were addressing someone. And then there it was, a deeper voice in reply. "Damn," I thought, "She did bring him home." I felt my cock involun...

American Vacation

by hyperpress on Dec 24, 2019
Transgender & Crossdressers

After picking up my luggage I walked out where all the taxis and buses and family members queued up to pick up passengers arriving from around the world. Miami Dade. You waved from your little SUV. You were smiling. I smiled back and hugged you before you could get all the way out of the driver's seat. You opened the back, I threw my suitcase in and hugged y...

Daniel and Jamie's Romantic Night Ch. 02

by lockedinsteel on Apr 17, 2019
Group Sex

Daniel woke up and realized that someone warm was pressed into his back, their arm draped over his side, their face nuzzled into his neck. As he opened his eyes he saw the clock and realized that it was later than usual, almost 10am. The events of the previous night came flooding back as his mind shook off the tendrils of sleep. He remembered submitting to...

Slut for All Pt. 07

by Knightofround on Sep 26, 2017
BDSM

It has been over a month since the night I crossdressed and got fucked by Anthony, a large black man with a massive cock. Vikki and I have gone back to our normal sex routine. The rules of wearing my collar and panties are still there, but she hasn't used a strap on or any toys in my ass for the first two weeks. I guess she wanted to make sure I recovered ni...