Cuckold+and+stockings Stories

359,783 results
Orientation
Length
Source
Infinite Scroll

Jill and Hob's Micromanaged Romance

by oneofthetwelve on Sep 16, 2017
Romance

Chapter One: Boy Meets Girl I noticed her on the bus ride to downtown in the morning. She was a very pretty young woman in her mid twenties with a nice shape but painfully shy. She had a faded purple streak in her brown hair but now she was sporting a new style, blond curls with highlights. She worked in an office and always wore sneakers even with her dres...

An Interlude, Bailey on the Prowl

by Sissy_Chantel on Nov 26, 2017
Transsexuals & Crossdressers

A little quickie story published between my continuing chapters of Recruiting a Sissy Maid... I hope you all enjoy it and find it, well hot... Characters in it will be new. All names and persons here are fictitious and any resemblance to real persons is coincidence. **************** As I sit here at my bedroom's makeup table, freshly showered, shaved, swee...

A Christmas present

by Shrubbery on Aug 19, 2017
Exhibitionist & Voyeur

This is a true story, although the names and some of the details have been changed. Jennifer, I can only say sorry it took me so long to get round to writing it down! ********* Walking over the worn carpet of the steps down into the warm fug of popcorn and leather seats, I already had goosebumps and shivers cascading over my skin and a hungry, flutteri...

When Love Returns

by xtcnymphette on Sep 16, 2017
Sci-Fi & Fantasy

When love returns. An older nymph finds love in the arms of a young boy and she is torn between her desire for his love and the urgent need to feed her nymphen hunger. It had become so much more complex than she remembered this process of transformation. So many passport issues and bank account transfers. The lawyer lying comatose on the bed across the roo...

Madonna v Chelsea FC

by bigaldo on Sep 17, 2017
Celebrities & Fan Fiction

Madonna didn't enjoy these charity ceremonies, but she did like the after show parties, and tonight, with Guy away filming in LA and the kids staying with their nanny, she decided to let her hair down and give it a go. The limo dropped her off at the end of the red carpet, and she was met by a battery of flashlights from the assembled paparazzi that were fig...

Olivia's Revenge

by OliviaFantasy on Sep 13, 2017
Erotic Couplings

This is not a multi-part story but it might have a sequel if people thought it could. It is my first on literotica so I hope you like it. ***** Olivia sat down at her desk stunned. Moments before she had expected to be given a promotion and made director. But she watched her boss name Sharon to the job. She liked Sharon, she was nice enough. But Sharon was...

Finding the Perfect Fit Pt. 12

by Joshana on Jan 27, 2020
Transgender & Crossdressers

After Waking up disorientated and wrung out, I lay there looking at my dorm's lumpy, discolored ceiling before noticing Jamie's breathing next to me. Lulling my head to the side, I saw him flat on his back, still with stockings on but having cleaned up at some point. The steady, slow tempo of his breathing was comforting and the view of his chest rising and...

What's The Password?

by bigdaddysmooth on Sep 12, 2017
Interracial Love

The dimmed hallway led to an old gated freight elevator. It looked like the setting for a horror movie, but they walked down anyway...cautiously. As they made their way, their heels clacked against the hard tiled floor. Meanwhile, in a darkened room...camera monitors track every step of these two sexy, young, Asian ladies. At the elevator door the two wom...

The Short Skirt

by babswalker on Sep 25, 2017
Mature

After my rather drunken night, I was a little apprehensive about going down to breakfast and seeing James the young waiter or Henri the barmen, with whom hubby Tom had shared me the previous night. All sorts of thoughts went through my mind - that it would be all over the hotel, that having had a bit of fun with an older woman they would treat me as a bit of...

Sex in the Sahara Ch. 04

by sweetlinda on Sep 19, 2017
Erotic Couplings

Chapter Four: Wet Dreams Linda’s narrative The sun had disappeared and the clear, bright stars had been lighting up the un-polluted sky above us for an hour or more when I spotted a grove of trees just to the left of the vehicles headlamps. I had been driving for about 2 hours and my mind had cleared from the affects of the beer and shit I had been smoking...