Bully Roommate Sissy Stories

23,222 results
Orientation
Length
Source
Infinite Scroll

Riding the Train

by Agnol on Sep 1, 2017
Group Sex

Just a quickie I tossed off. Everyone is over 18 * Cold rain whipped at the platform, umbrellas held low almost like shields to protect the passengers who waited in the shifting lines to board the train cars. Elizabeth Reynolds, sandwiched between two large men tried to maintain some semblance of propriety but the surging crowd made it impossible not to cr...

The Day My Life Was Changed Forever

by cddream on Sep 15, 2017
Fetish

First i have to really have to thank g1dnshwrgr1 for all her help putting this story together, edditing and re-writing the final draft!! thanks again!! Hope everyone enjoys my experience as much as i did!! I may not remember what I had for dinner last night, but I can definitely remember the exact day my dirty little secret started. On a hot summer day,...

Tell Me

by monika ikon on Sep 16, 2017
Transsexuals & Crossdressers

It was a Friday night, in the middle of summer, and I didn't know it but my life was about to change forever. I had just come in from a quick before-dinner dip in the pool. Wendy greeted me with a drink and a sexy little smile that told me she was in the mood to fool around. I was beat from a very hard day at the office and a long hot commute home from the...

Stuart's Psychologist

by justincbenedict on Sep 13, 2017
BDSM

"Take them down, Stuart...like the shameful little boy that you are!" Stuart couldn't believe Dr. Townsend was talking this way. And right in front of Moira, too. She looked horrified at Stuart's therapist, a muscular silver haired, pinstriped John Forsythe look-alike--yes, he looked very much like Forsythe's "Blake Carrington" character on Dynasty. Dr....

Maltese Penis

by Jenny _S on Sep 1, 2017
Humor & Satire

Someone knocked on glass door of the Spade & Archer office. From under his dark brown fedora, Sam Spade pried open one eye then placed the half bottle of Old Sweat Sock in his desk drawer while he shoved the cock he had been stroking back in his pants. Rising, he straightened his trench coat, drawing the belt tight around his waist and tied it in a knot. "Co...

Greta Fights Mommy Adriana

by Gretatv on Sep 16, 2017
Transsexuals & Crossdressers

Dear Readers, this is the second part of the Mommy Adriana series. I hope you enjoy the ride, there is more to come. * * * * * Mommy Adriana continued her assault on my boycunt with her 10 inch strap-on dildo stretching me to the hilt. Meanwhile Andrea, my wife, had gotten up from my face, leaving me drenched in her juices. She sat exhausted on the couch...

My Date

by corsetheelscollar on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One The first date went well. I met Francesca outside the cinema. She looked exactly as she had described herself. Tall, particularly in the incredible black boots, athletic, with long auburn hair. I was attracted to her straight away, and loved the way she took my arm, smiled and walked with me into the cinema. We had a few minutes before the fi...

On the Bike

by Cat_Fantastic on Sep 13, 2017
Erotic Couplings

The knock on the hotel door sounds so loud in the empty room. Taking one last look in the mirror, I move towards the door, tucking a short strand of hair behind my ear. Hair braided, tank top and bra, jeans, and Harley boots complete my outfit...I hope it meets your approval. A nervous breath and I open the door to see you standing in the hallway, mischief l...

Crime Doesn't Pay

by Virgil_Assad on Sep 14, 2017
Transsexuals & Crossdressers

::A note for the readers. I came upon the idea for this story some time ago. Most forced feminization stories are told from the POV of the subject being forced. I decided to change the format a little and tell a story from the other side. Special thanks to Anelle for help in editing.:: I had originally intended to move straight from one apartment to the...

Stuart's Secretary

by justincbenedict on Sep 17, 2017
BDSM

Stuart thought dreamily of his days at the firm in Chicago, and the two male Masters he'd lived with... One of them deaf. The rich 26 year old Stuart had loved and feared the two men. Now he watched BDSM porn... The way that model has his cock whipped reminds me... Of the day Master Pietro caught me with the Frederick's of Hollywood catalogue that I'd...