Prissy Sissy Stories

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College Crossdressing Confessions Ch. 02

by wifetoy on Sep 11, 2017
Transsexuals & Crossdressers

My wife's control over me insures that I have no secrets from her no matter how depraved my hidden desires. As part of my training, she has ordered me to confess my prior deviant acts to the world. This is the second part of a series in which I obey her command that I confess my past experiences as a panty thieving college cross dresser. I have changed some...

David & 'Lyssa Ch. 02

by millennium_bard on Sep 15, 2017
Sci-Fi & Fantasy

Prissy let her block on 'Lyssa's powers dissolve away. She figured that the nicer she was for now, the better her chances were of coming out of this mess in one piece. David paced through the entrance hall looking at his surroundings. Fine wood paneling lined the walls; Furniture any piece of which would bring a fortune from any antique auction decorated t...

Teacher's Descent into Ecstasy

by DDDDave on Sep 25, 2017
Erotic Couplings

"Big Tits, Big Dicks and Fantasy Fucking" ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) He strolled into the classroom over twenty minutes late. Again. It was the last class of the week, a study hall for students taking the absolute minimum of classes to graduate. Most of the time he just skipped. He was repeating the...

My Girlfriend's Sissy Roommate

by SEVERUSMAX on Sep 15, 2017
Transsexuals & Crossdressers

"Look, Stan, there's ... there's something that I have to tell you and explain. It's not easy. In fact, it's very fucking weird, even to me, even while I've been letting it happen. I have to level with you, because, well, you and I have been flirting for a good while now and I'm smart enough to realize that you want me. Hell, I want you, too. This is very .....

Find the Cheerleader, Save the World

by Sissyhalo on Sep 16, 2017
Transsexuals & Crossdressers

It started with my brother Holt. A year younger than me he's...he's turned into a fucking cuck sissy faggot. I'm serious and I'm not just spouting off. Holt's always been a dense guy but this...he starts hanging with this loser from high school and I mean a loser. AV club, geek stuff, nothing in Holt's yearbook that said anything but loser, geek and loser...

Keeping Up With the Joneses Ch. 01

by DarkBlush on Sep 25, 2017
Interracial Love

This is the sequel series to my story The Monster Behind The Desk. It's my most read yet second popular series but all the while my lowest rated. Dylan Jones is my favorite character so I'm going to keep it going. All of these are going to be vignettes under 2000 words. So enjoy. ***** Prissy did her best to sneak down the stairs into the kitchen. She look...

Poolside Pussy

by Boxlicker101 on Sep 13, 2017
Exhibitionist & Voyeur

Priscilla Larson is usually called "Prissy" by her friends, but the name is a joke, and everybody knows it. There is nothing the least bit prissy about her. She loves putting her sexy body on display, but she loves it even more when the men or women looking at her want to go much farther than that. Pricilla had finished her first year at the state universi...

Helping Jess Pt. 05

by mski on Sep 25, 2017
BDSM

I slept well that Sunday night which surprised me, though I guess I was probably exhausted. I woke up with my normal hard-on a bit before 5am, well it would have been a hard-on but for the cage. My penis was certainly trying. I never found it an uncomfortable feeling, just frustrating that there is no ending and I could not jerk off, and now who knew what wa...

Summer Hire Ch. 05

by brentaden on Sep 11, 2017
BDSM

Decision "So we didn't say anything more. We got back to his house, and I didn't really say goodbye or anything. I just kept on walking up to where I'd left my car and drove away." Melissa looked up from her unfinished bottle of beer, which had grown warm while she told Malcolm about her day with Erik. Shame and sadness tempered her voice. She did feel a li...

Cornholed

by LaBlancheTraversee on Sep 11, 2017
Fetish

I'm in Tori's basement - tied to a chair, blindfolded, naked and gagged. My hands are cuffed behind me and my rock-hard cock is locked in the plastic cup of a chastity belt, engorged and aching for the feel of her delicate skin. Fantasies of her jacking me off with her hand send a jolt of electricity rushing down to my cock as thoughts of our earlier phone c...