Sissy Girl Stories

198,414 results
Orientation
Length
Source
Infinite Scroll

Costumed Ball

by Selbryth on Sep 14, 2017
Transsexuals & Crossdressers

So there I was, at a Halloween costume ball on campus (of a rather prestigious college), having my first real lesbian stolen kiss—behind the fichus on the second floor balcony of the fraternity—and though I was dressed like a drill sergeant and she was dressed like the Elf Princess from Lord of the Rings, I really loved the heck out of it! I mean, it's not l...

A Perfect Fit Pt. 12

by umami on Mar 6, 2018
BDSM

All characters are over 18 years of age. ***** Mark is out of sorts. The loft has an uncanny appearance and creates a funny feeling in him that makes him count out his pills. He's just checking the number against the calendar. He had been taking them correctly. It's that his girl is not there. She's packing her remaining things at her old apartment and i...

Pegged for Love

by silkstockingslover on Jan 31, 2018
Fetish

Summary: Straight guy is pegged by the girl of his dreams. This is a 2018 Valentine's Day story so please vote. Thanks to Tex Beethoven, thor_ph, Robert, and Wayne for editing. Pegged for Love It is probably the truest saying in the world: you can't just be friends with a girl of the opposite sex. I mean it may be possible when you're an adult or marri...

Forever Alone's Guide

by OzzyDaBum on Sep 13, 2017
How To

After my exile from my home to study the dull career of computer programming, I've been overexposed to the internet trolling and the quite side of living the bachelor's life. For me it was weird to image that some people couldn't blossom as I did, but some people just won't shut up about how its SOOO hard to find anyone. This is list for that "Forever Alone"...

Remedial - 9:00-9:30 AM

by Alex Finch on Sep 14, 2017
Erotic Couplings

It’s morning, not particularly early, but overcast; if you are the romantic sort, or the depressive sort, or some easy combination of both, it gives the distinct impression of faded photographs. Those gray skies. It’s like the whole of the earth is encased inside of a slate chest that just had the lid shut; it’s foreboding and draining. It saps the strength...

Lighting up Starlight Ch. 02

by MTL17 on Nov 16, 2020
Celebrities & Fan Fiction

Disclaimer: I do not own The Boys. I do not make any money from the writing of this story. ***** Queen Maeve tried not to smile when she saw Starlight, and failed, but managed to turn away from the nearest camera while doing it, and then tell the other girl, "I need a word with you." "Erm, sure..." Annie replied nervously, then as they started heading tow...

"Yes, Mistress Valerie" Pt. 02

by whistlingogre on Sep 25, 2017
BDSM

Read part 1 here http://www.literotica.com/s/yes-mistress-valerie ***** "I want you to suck on my nipple." Clara's eyes widened. "Yes, Mistress." "Don't act so surprised, bunny. Did you think I was just going to stand here and talk to you?" Valerie stretched her shirt taught and moved so that her nipple was right in front of her friend's mouth. "Close yo...

Taming the Dom

by Ben Rosewood on May 31, 2019
BDSM

This story has been created with Game Mode in mind. For the best experience, please turn Game Mode on. Your best friend Eddie had said it was urgent. Upon receiving his text, you head to your normal meeting place, Godzilla's Pizza Dojo. The place is covered in framed monster-movie posters and arcade machines that Eddie has topped the high scoreboards on. You...

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Study Session

by CaliVal on Mar 26, 2019
BDSM

I come into your small office, dressed in a short plaid skirt, and a white button down blouse and high heels. My hair is in the cutest pig tails you've ever seen and I'm sucking on a lollipop. I start to unbutton my blouse button by button slowly revealing my front clasping black bra. You can start to see my tattoo that's situated right between my breast. Y...

Car Fucked

by Analqueen22 on Sep 16, 2017
Anal

"I bet you she's a nerd," Sam blurted to his brother when he saw the perky black-haired girl sitting alone in a booth next to the door of the coffee shop they just parked in front of. "Just because she's wearing glasses doesn't automatically make her a nerd, Sam. She could be a special needs person," Dean tried to reason. Sam just shrugged and got out of t...