Bully Roommate Sissy Stories

23,222 results
Orientation
Length
Source
Infinite Scroll

Sodomy in Santorini

by gomorrah on Sep 14, 2017
Fetish

I first met Soula seven years ago whilst on my way to do archaeological fieldwork at Akrotiri on Santorini. I had caught the Blue Star ferry from Piraeus (Athens Port) via the Greek islands to Santorini. The whole trip takes about 17 hours and goes via some beautiful islands - Parros, Naxos, & Ios - but takes so long there is not much to do. As the sun set...

Shooting The Moon Ch. 02

by SEVERUSMAX on Sep 15, 2017
BDSM

Apparently, I fell asleep drunk and tired, which wasn't too surprising, given how much Jameson I drank the night before and how much I had fucked my three playthings. I didn't wake up alone, however. I was in my studio apartment, lying on the sofa, with Dana planting kisses on my cock and balls. Oh, yes, Dana ... the pizza girl, who had been so passionate an...

First Time Out

by Fairy_Nancy on Sep 14, 2017
Transsexuals & Crossdressers

I'm so excited and want to relate this 100% true story quickly while it's still fresh. Please forgive any typos. [My background: Age 48. Closet dressing in earnest for 15 years. Began with slips stockings and nighties but have collected extensive full wardrobe and accessories over time. Boobs, wig, jewellery etc. Slim with shapely legs, dress size UK 14. Se...

Inaugural Crossdress Sexfight Ch. 02

by danidhotcd on Sep 16, 2017
Transsexuals & Crossdressers

CXSFL – Match 2: Dani vs Jamie With my first match under my belt, albeit a humiliating lopsided loss, I felt better prepared and even more excited to try another match. I was hoping to be on the giving end for my next match and felt I had learned some valuable lessons that would increase my chances of getting a win. Although it's difficult to complain about...

Damsel in Distress Ch. 02

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Imagine your sister asking you to chaperone her on a date. Would you? Debatable - Now suppose you had to dress as her girlfriend? Duncan did but it was his sister who came to his rescue when subjected to a humiliating ordeal. This story can be misleading. It starts as an endearing sister, brother crossdressing scenario that develops into a humiliating and b...

Does He Really Want That? Ch. 06

by goamz86 on Sep 18, 2017
Loving Wives

Note from the author: This is a continuation of a story with five previous chapters. This chapter win not make a lot of sense without reading the previous chapters. Furthermore, this is a cuckold, Femdom, sissyboy story. If you don't like thos kind of stories, please move on. Don't read it an leave senseless comments at the end. I love feedback, as...

Mistress Di

by justincbenedict on Sep 14, 2017
BDSM

Di gently stroked Trent's dick with her red nails. "You like that, Trina, you little bitch?" she whispered softly in Trent's ear. "Mama may want you to go suck some dicks for her later worthless little tranny-bitch." She lay next to Trent in her low cut blue velvet embossed chemise and scalloped lace trim. Trent, for his part was wearing pink stockings and...

Halloween Party

by cuck2serveU on Nov 26, 2017
Interracial Love

Trish and Brent hosted the Halloween bash this year. Once again Jennie was still busy with her new vanilla man so she opted to send a replacement for me to service. Once again it would be a surprise because that's how she rolls. As always, this party is the most expensive of the year because it's held at a hotel in Vegas and there is an entry fee for all cou...

Spanking Jay

by Kimberleigh65 on Sep 17, 2017
BDSM

"Let's stop here." "Jay, I'm tired of being in the car." Melissa gazed out of the car window. "We're out in the middle of nowhere. We can pull over, get the picnic, walk for a few minutes then have something to eat and relax. Then find the place. It's on this road – County road 67, we just haven't driven far enough." Jay pulled the car over to the verda...

Cabin Outing

by DarkYaish on Sep 19, 2017
Loving Wives

The woman across the table was on the younger side of middle aged, attractive, and at least partly asian in descent. Her figure was well shaped, with a bit of plump lushness that hinted at full bodied passion in everything she did. That figure was encased in a sheer black dress, stopping just short of mid-thigh. Her long, slim legs were highlighted by black...