Bully Roommate Sissy Stories

23,222 results
Orientation
Length
Source
Infinite Scroll

The Cuckold Husband

by alwaysready4 on Sep 18, 2017
Loving Wives

My wife Kim met Jim a 23 year old college student when she was in a chat rooms online. They had chatted in the room for a few nights then went to a private room. They exchanged photos and began talking on the phone. They talked till the wee hours of the morning. I would lay in bed and hear her laughing and talking about the kind of sex she wanted to have wit...

The Trouble with Roommates Ch. 07

by KaylaG on Sep 18, 2017
Transsexuals & Crossdressers

Kneeling on the passenger seat with her short skirt and panties facing the window and her mouth wrapped around Brian's cock while he drove, Nicole was ecstatic. Not even the hoots and honks from truckers going by could break her good mood. Brian was going on a business trip for 2 weeks, and Nicole would have the house to herself the entire time. Two weeks wi...

Slave Ch. 03

by slaveheathen on Sep 25, 2017
Fetish

Note: This is a fetish story involving a bisexual submissive man. So there's guy-on-guy action, piss play, cross-dressing and much more. If that's not your bag, please don't read it. If it is, enjoy! Comments are welcome, including constructive criticism. Now on with the depravity... ***** Good thing the next day was a Sunday. I was walking funny. I was...

My Brother, My Sister Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

I wrote this story originally under the title "Be Careful In the Park" about an older crossdresser who meets a street gang in a park and gets more than she bargained for. There was no incest in the original version. I like this version better as it includes all my peccadillos: incest, crossdressing, nylon fetish, and forced sex. A warning to those who find t...

Damien Skylar Ch. 04

by xxxArtemisDawnxxx on Sep 16, 2017
Erotic Horror

**Author's Note-Again everything belongs to me. I hope you enjoy it, and again there are different points of veiw, you'll be notified when it changes, and as promised this one contains more sex than the last. If you haven't Id recommend reading the first 3 chapters before you continue this one. Hope you enjoy.** '...' thoughts **...POV** Point of veiw chan...

The Hitch Hiker: Amy

by Just Plain Bob on Sep 17, 2017
Loving Wives

"My trousers fell to the floor and her eyes widened as she saw my proud tower of flesh. She stared in fascination as I climbed on the bed and positioned my thick, eight-inch piece of man meat at the entrance to her tunnel of love. Suddenly, as if coming out of a trance, she cried out, "No, we can't, we must not. It would kill my husband if he found out." "...

Another Time & Place Ch. 1

by WolfSpirit on Aug 16, 2017
Exhibitionist & Voyeur

The young lovers cuddled under the blanket, hands busy arousing, caressing and teasing each other. She was wearing a replica of an antebellum gown, complete with silk frills on the scoop-necked bodice and a tight corset giving her a wasp-like waist. It fit her submissive nature perfectly: her breasts rested on bone-hard braces, the nipples uncovered and show...

Separation Trial (Trial Separation)

by fetisha_44 on Sep 2, 2017
Fetish

We had been married about three years, when my wife and I decided that it just wasn't working. We agreed to a "Trial Separation" with the proviso that we could see others if we wished to, but somehow I didn't think that Gayle would do anything about it in a physical sense. I had always been a gentle lover, and she seemed like the quintessential "ice queen."...

I Learn My Place In Our Marriage

by Quietoldie on Sep 14, 2017
Loving Wives

Jane learns to take the upper hand The sex in our marriage was becoming a bit samey as both me and my wife are not very assertive so I thought I would try to spice it up a bit. My wife, Jane was brought up by her grandparents and she seems to have internalised their rather outdated attitudes towards women's lib so I searched around on the internet and found...

Dede does Joseph

by Newkinkstories on Sep 14, 2017
Erotic Couplings

She stood five foot eight and one half inch. A former cheerleader, she now taught at the local Catholic school. Her blonde hair, green eyes and large 36DD breasts were the cause of many a wet dream for the teenage boys in her class, but Dede wasn't taking any chances with them. She and her best friend Jennifer worked together and always made sure they were...