Sissy Lingerie Stories

30,229 results
Orientation
Length
Source
Infinite Scroll

Prisoner Of Lust

by ChainedToAKeyboard on Sep 28, 2020
BDSM

Prisoner Of Lust A Latex Futa Nuns From Hell Side Story Camilo paced nervously in the kitchen as he looked at his phone. It would ring any minute and his nerves were standing on edge. He'd just closed his laptop after a brief chat with a woman on Fetlife. At least, he hoped it was a woman. One could never be certain a stranger's profile was real until y...

Hermaphro-Love

by JaJimLy on Oct 26, 2020
First Time

Erotica 10 – Love Found It has been a long day. Deborah, although longing, has never been much for the world of romance. Her calendar never leaves her much time for building seriously a relationship that could support that kind of thing. She was always more pragmatic, trying to figure out how to survive or, when surviving wasn't an issue, and college offere...

Wife's Business Trip

by Woulditkillyou on Sep 25, 2017
Loving Wives

My Husband has always had a fantasy about watching me with another man. I personally have never been interested in this type of fantasy. Not that I don't have a few fantasies of my own, but to be with someone else just doesn't turn me on. I don't understand why this is such a big turn-on for him seeing me be with someone else or knowing someone else has been...

My Initiation

by cdandy on Sep 18, 2017
Transsexuals & Crossdressers

Chapter 1 She was ambling slowly through the mall gazing in shop windows. A stunningly beautiful brunette wearing dark stockings over long shapely legs, a white cotton blouse decorated with delicate embroidery and a beige skirt that seemed to hug the hips then flair out at the knees. Unable to help myself, I stared openly at her legs beneath the skirt, the...

Interesting Consequences

by jordanmoss1000 on Aug 19, 2017
Exhibitionist & Voyeur

"What a sweet girl." That's how almost anyone in my home town would have responded had you mentioned my name. Looking back I suppose I was the embodiment of the innocent, fresh-faced and naïve teen-aged girl. In some strange way I guess I knew that and embraced the role with a flourish, always smiling, always sweet, always sickeningly cute to be honest. I...

Sherry's Test Ch. 07

by PolyVoyeur on Sep 11, 2017
Exhibitionist & Voyeur

Author's Note: Please read this story in sequence, otherwise it may not make sense. Comments/Feedback will be greatly appreciated and responded to. If you like the story, please take a moment to vote. ------------------------ -------------------------- Thursday and Friday at school was awkward for Nancy. The Principal had forbidden any overt references...

Carrie's Pussy Ch. 03

by 0ra11yfix8ed on Aug 28, 2017
Fetish

When I left Carrie's apartment Saturday night it was a little messy! I was just too tired to clean to after myself. Not to worry she had called and told me her return flight was Tuesday. I'd have loads of time to get things back in order. I was sore. Really sore! So sore and spent that I didn't wake up with an erection. Apparently keeping yourself hard for...

A Virgin Roughly Handled Ch. 02

by ArielRacine on Sep 14, 2017
Erotic Couplings

All the characters who appear in this story are over 18. Yesterday, Sandy was seduced by the man she had a crush on. Today, she's giving him everything. If you haven't read Chapter 1 yet, go there first. This chapter stands alone, but it's even better if you know how Sandy and Jim got here. Enjoy! -AR ***** "Good morning Kitten" was the first thing I heard...

Samantha's Secret Submission Ch. 04

by SubmissiveVirginSlut on Sep 19, 2017
BDSM

I woke up the next morning in my own bed, naked beneath my lavender cotton sheets. I didn't even have a moment to wonder if last night's intense sexual encounter was a dream before I moaned at the aches in my body. I rolled onto my back to ease the tightness in my shoulders from having had my hands bound behind my back. My red raw nipples extended from my br...

Roommates Ch. 01

by Radnok on Sep 13, 2017
Erotic Couplings

[Made in all fantasy, enjoy.] My best friend, Isabella, and I were always flirtatious. It was a habit of ours, neither "good" nor "bad". I've always had a crush on her for the longest time. She was the first person to become my friend when I moved here. We grew up, she went on to date other guys, but I was always there for her. When she and her boy friends...