Caught Crossdressing Stories

164,111 results
Orientation
Length
Source
Infinite Scroll

Teach You a Lesson

by Tinkerbell0417 on Sep 12, 2017
Erotic Couplings

Stomach in knots, a tall blonde knocked on the door to Darren Cook's classroom. Tapping her foot anxiously, Brianna White waited for the teacher to answer. After what seemed like hours, a low husky voice answered. "Come in." Licking her lips briefly, Brianna opened the door and let herself in. "Hello, Mr Cook," she spoke softly, voice trembling with nerve...

Panty Boy

by 32B_minus on Sep 13, 2017
Fetish

The first installment telling the tale of a young man's fascination with ladies underwear, his family and his sexual development. As always, I reserve all rights and warn you that it is vaguely incestuous and certainly a bit fetish oriented so if that's not your cup of tea, stop reading. Comments and helpful criticisms are always welcome but the anonymous, i...

Christine's Advice

by AnnHoytRedlass on Aug 18, 2017
First Time

They had been together for a little over three years. She was his best friend, and he was hers. They were deeply in love and the sex, although infrequent as it used to be, was still considered "good" by both parties. With their hectic work schedules and the other responsibilities of adult life, sex often took a back seat to other day to day distractions. It...

One Magic Night

by BrenKyveli on Sep 18, 2017
Erotic Couplings

All characters are over twenty-one. ***** Rachel folded herself into her favorite corner of her overstuffed couch, in her cozy apartment. She had a new book in one hand and a hefty glass of wine in the other. She wasted no time at all and eagerly delved in. Several minutes later Rachel had to put down her book and fan her face with her hand. "Wow. Now...

Touch of the Wolf Ch. 02

by whitesabretooth on Sep 25, 2017
NonHuman

Author's note: All characters and companies mentioned in this story have no existence outside the imagination of the author, and have no relation whatsoever to anyone or anything bearing the same name or names. Events portrayed in this story are pure invention and have not been based on any events that have happen in real life. All the characters involved in...

A Job in the Theatre Ch. 15

by BothWorld on Sep 15, 2017
Transsexuals & Crossdressers

Chapter 15 -- Doing Darrin Sarah and Paula shared at drink as they tried to decide what to wear for their date. "Every good outfit starts with lingerie. What do you think of these?" Paula asked holding up a pair of baby blue panties. "Nice. But I really think these will be better" Sarah said holding up a pink pair featuring ruffles across the back. Paula...

Satan's Whore Ch. 01

by ktmccoll on Sep 14, 2017
NonHuman

Following the events related in the series "Incubus", the succubus named Kat goes into voluntary exile. This is her story. *** "Why me? I'm at the end." The elderly man was half asleep and his words -- thin, dusty syllables -- seemed to come from a great distance. What could she tell him? That she hoped that her stain on him might be less than on someon...

Going Deep

by zrob on Sep 12, 2017
Mature

Ryan Grant was nearly finished with the neighborhoods he had been given in the yearly fundraiser. The seniors on the Middleton Bison football sqad were required to go door-to-door to sell Varsity Cards which provided discounts to local stores and restaurants. Ryan was the first team QB, so he was able to swing the assignment to one of the more affluent subdi...

Changed Ch. 02

by a_koozie on Sep 25, 2017
NonHuman

Once she got home, Karen cleaned the house from top to bottom, and then baked 3 batches of cookies and a cake to work off all of her nervous, pent up energy. Finally, she allowed herself to sink into her old fashioned claw footed bathtub. She sighed and the days tension seemed to flow out of her. Leaning her head back onto a pillow, she let her thoughts repl...

Manipulated Virgin Secretary

by Unkith on Sep 26, 2017
First Time

Sameer was losing his mind. He would try concentrating on his work but his thoughts would continuously wander into imagining a sexual encounter with his secretary, Sonia. And how was he to resist this temptation? Day after day, week after week and month after month she had been working with him, sitting directly across from him and giving him an ample view...