Bully Roommate Sissy Stories

23,222 results
Orientation
Length
Source
Infinite Scroll

The Constance Gardener

by CarrieQ on Sep 16, 2017
Transsexuals & Crossdressers

This is a tale of a chance encounter along the long tow-path that trails below the garden gates found between Runnymede and Windsor. I guess, if you wanted, you could wander all the way from London to Reading on that path? Not my idea of fun though, as I'd waste an otherwise perfectly good pair of heels, but I reckon it's doable. My friend Connie lived abou...

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...

Chrissie a True Slut

by easyballs on Sep 14, 2017
Erotic Couplings

Chrissie 'Cums' to prefer the 'Bully Boy' to Fiancée Again my thanks to Jill for her input and suggestions. If you are easily offended by stories regarding sexual intercourse don't continue reading go buy the dandy! ***** Hi my name is Chrissie, I'm a nineteen year old student and I just had to tell someone about my own story. I had a boyfriend who I was...

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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Her Bully's College Roommate

by samwalser on Sep 26, 2017
BDSM

Amy was giddy with excitement when her parents dropped her off at the Central University of North Texas. Everything was about to change for her. She'd been teased and bullied all through high-school for her appearance (she's barely five feet tall, skinny, flat-chested (but with big, sensitive nipples, and freckled) and for her general nerdiness—she read a lo...

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A Slut's Triangle Pt. 14

by Kantarii on Sep 19, 2017
Transsexuals & Crossdressers

It's funny how things never go the way they're intended to. For a transvestite, I seem to get myself in a mess in a hurry. My random idea to suck Keith's cock and, hopefully, allow Kimberly to think that he's my boyfriend is going horribly wrong. Brenda told me not to do anything stupid, but, as usual, I fail to listen. Blinded by my need for some dick, I...

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...

X-Change

by Noah_Peal on May 15, 2015
Miscellaneous

Pills Pink pills change males to females. Blue pills change females to males. Purple pills (X-Trans) change males or females into transgenders, can be combined with pink or blue. X-Change (Formula subject to change) Acquired from unlicensed "street" vendors. Changed (defective/in testing) formula. Cheapest. High pregnancy risk. Can lead to mental a...

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The Roommate Pt. 07 - Miranda

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

The next day, when Josh returned home from teaching college students (who were only around six years younger than him), Miranda met him at the door. She seemed in a fine exuberant mood and gave him a smile. Sometimes he didn't know which personality he'd find - the friendly, mother-like woman who helped him become Lori, or the controlling figure who could...