Sissy Roommate Stories

20,331 results
Orientation
Length
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Infinite Scroll

Slut for All Pt. 06

by Knightofround on Sep 19, 2017
BDSM

"That's it baby! You are such an amazing cock sucker!" Anthony stands towering over me from my knees. Like a proper slut, I make sure to keep eye contact with my new master. I moan around the cock in my mouth as I bob up and down quickly. Anthony puts his hands on the back of head to grab my hair and stops me from moving up and down the amazing nine inch c...

Sarah had a Surprise Visitor

by SarahCD on Mar 26, 2019
Transgender & Crossdressers

A few years ago I was working in Hamburg, Germany, and living in a nice, all expenses paid, downtown apartment. Visitors had to be 'buzzed' into the building and so I believed that I could never be surprised by a visitor. I could either ignore them or put on a dressing gown before they got to my door. This was good since I love to dress as a girl whenever I...

The Roommate Pt. 03 - Miranda

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

Author's note: I notice there are several other Literotica stories also using the title "The Roommate," so I decided to differentiate this series by adding "Miranda" to the title. Thanks for your comments; I enjoy reading them. ***** Miranda and Josh didn't see much of each other for a week and a half. She took off for a few days to visit relatives (drivi...

Darling Nikki

by Latexsissy69 on Sep 25, 2017
Transsexuals & Crossdressers

Chapter 1 - The Setup "I'm going to catch him!" Samantha thought to herself as she looked at her disheveled panty drawer. She now had proof that her roommate, Nick, had been wearing her clothes, but had to catch him in the act. She did a search online for ideas on how to catch him. She looked at cameras, tape recorders, etc... but she knew it wouldn't hold...

Virus S

by thisisnttaken8 on Jan 17, 2021
Bisexual

"FUCK ME YOU STUD!" the slender new trap screamed in agonizing bliss as the muscular stud pounded him from behind. Connor could see the brute's body changing by the second. He arms grew more muscular and his jaw grew more angular, but even stranger was his cock. It seemed to be growing thicker and larger as he plowed the twink's ass. The bull wasn'...

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Gothic Sissy Snowbunny

by Satanicsissybitch on Mar 2, 2020
Transgender & Crossdressers

Don't ask me why but I've recently decided to come clean. To the world, my readers, my friends and most importantly, to myself. I can't hide or pretend anymore and I've decided to just put it all out there for the world to see and, believe me, it's extremely difficult for me to tell the story I am about to tell you. First, I think it's probably important t...

A Husband Named Cathy

by cathynylons on Sep 25, 2017
Transsexuals & Crossdressers

When my wife Jane first found out about my naughty little secret she flew into a rage and launched into a tirade calling me a lying, duplicitous, deviant, degenerate pervert sissy faggot. She stormed out of the house slamming the door behind her. About an hour later she returned and had calmed down. In a very apologetic tone she said that she was sorry and...

Becoming Sissy

by SissyCockWorship on Nov 25, 2016
Transsexual

A slim boy, slouched in his seat. The ramblings of his cute professor were barely audible to him. His mind was racing. Today had snuck up on Keith. He could not believe what was going to take place later tonight. "Keith..." His beautiful professor snapped him out of his day dreaming. Her low cut top revealing her full breasts was barely a distracti...

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An Expensive Addiction Ch. 03

by NeverGuessWhatsNext on Sep 16, 2017
Transsexuals & Crossdressers

The Friday after my second encounter with English was just as eventful as I had thought it would be. My girlfriend got to town, and since we hadn't seen each other in weeks, she was hornier than hell. I picked her up from her parents house around 5 and we went straight back to my place to have sex before going to the party. A couple of months after we starte...

The Blackmailed Sissy

by jmanrules on Sep 13, 2017
Transsexuals & Crossdressers

Jon walked into his roommates bedroom looking for the phone charger he loaned Eric the night before. As Jon was looking around he saw several pairs of panties, bras, and pantyhose. Not thinking anything of it Jon just grabbed his charger and left with it in hand. After he sat down it dawned on him that Eric has never brought a girl over and even if he did th...