Bully Roommate Sissy Stories

23,222 results
Orientation
Length
Source
Infinite Scroll

Make Up Exam

by ZackOShea on Sep 1, 2017
Humor & Satire

"Come on, what's in the bag?" Woodrow used his elbow to give Eddie's a nudge as they headed down one of St. Agatha's halls. The bespectacled doodler just wasn't giving up. All three of the presidents had noticed the extra bit of plastic poking out of Eddie's backpack. Woody had just been the first to bring it up, he wasn't going to let it go. It was mostly b...

Rebecca and Rob

by marissacd on Sep 13, 2017
Transsexuals & Crossdressers

I'd been friends with Rebecca and Rob for years, and we'd spent a lot of time together. They didn't mind me being the third wheel, and I loved being in their company. The fact that I was sexually attracted to both of them was a secret I thought I'd kept reasonably well. She was dark haired and blue eyed, a fitness nut with a firm everything. Five and a half...

Dressed for Sex

by call_me_dana on Sep 18, 2017
Transsexuals & Crossdressers

This is a prequel to the Sissy Nicky story ... "Thanks Dana, I'm glad you could get here on such short notice." "No problem Angie, I'm glad I could help you out." "I'd have waited until Nick got home from his trip, but I really needed to get the laundry started and I haven't had water all weekend." "Why don't you show me to problem and I'll see what I ca...

Caught in Panties Ch. 02

by pantyperv on Sep 25, 2017
Fetish

The ride to the mall with Lisa and Tammy was long and silent. I couldn't believe my wife and her sister were taking me shopping for panties, especially when the panties we were shopping for would be mine to wear. The closer we got to the mall the more I hated myself for getting caught wearing panties. I knew I was in for a humiliating day. When we arrived T...

Labor Day Party Ch. 03

by nully on Sep 12, 2017
Group Sex

This story is the culmination of a long erotic dream I had one morning. I fleshed it out and added more details to make it longer. None of the people are real, but are loosely based on people in my life. If cuckolding isn't your thing...well, you can always click away. Or keep reading. You may find something you like... Donna stands in the doorway, softly...

Knight's Conquest Ch. 2

by evilernie on Sep 18, 2017
Sci-Fi & Fantasy

[Note: First, give me the chance to thank you for reading the first Chapter. I specially appreciated the nice feedback I got. This chapter is not a continuation of the first. I know people are aching to know what will happen to our hero. Well, I am afraid to that you probably have to wait months before we get to that. I am planning to narrate the events le...

Jerkboy Life Ch. 06

by stratoblaster on Sep 19, 2017
Exhibitionist & Voyeur

If you haven't read previous chapters, there may be some trigger-inducing stuff here. Keep in mind the characters are feeling what they perceive, not necessarily what's real. For those into exhibition and humiliation head trips...have fun! ***** The Landtree women met in the bar of a strip-mall eatery for happy hour. Suzette was talking about her sister Sa...

The Visit Ch. 06

by stateofdenial on Sep 15, 2017
Fetish

The very next morning after they arrived home she called his mistress to get the key. He was devastated when Tweets told him that she was out of town until the end of the week. She told him not to pout, that it was just little longer till she got the key. During that time she also had her way with him in every room in the house, in the pool, on the patio and...

Joel's Stressful Afternoon

by justincbenedict on Jul 18, 2018
BDSM

"You are, too a crybaby." Yvette smiled as she said this to the perspiring Joel, her ever devoted older boyfriend. They'd just come in from walking home with ice cream cones. "You complain, and whine and wimp out. You're a big sissy." Joel, not yet scenting the danger, protested good naturedly. "I don't think that's true. I do give you your own way a lot,...

Breckyn's Bashful Boss

by justincbenedict on Jul 4, 2018
BDSM

Loudon and Jeanelle Gaskin waved at their baby sister as she walked down the hall of the big law firm. "Make us proud, Breck, baby." Jeanelle called. The legal secretaries of their formerly white-trash family had been enriched by this amazing place... Juanda, Riva and Desna, Breckyn's great aunts were "document specialists" whatever that meant, and had rec...