Pillow Riding Stories

99,788 results
Orientation
Length
Source
Infinite Scroll

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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The Tales of Crissy the Sissy Ch. 02

by EPCene on Oct 12, 2020
Transgender & Crossdressers

Chapter 02 Chris Masters found his phone plugged into the charger. There were 37 new messages. He scrolled through the first few. It was a few of the guys from work. Some of them were giving him shit for calling out sick and a couple were worried about what had gone down the night before. A majority of the messages were from an MM. He clicked on the contac...

Bree Impaled

by CandyBree83 on Sep 25, 2017
Toys & Masturbation

She awoke from her dream - aroused. Bree had been dreaming of her new purchase from the night before. Saturday evening she had sat drinking a bottle of wine and surfed the net for something to spoil herself with. Since breaking up with her boyfriend Bree had been feeling increasingly horny with every passing day. So the night before she had decided to do so...

Second Time Around 02

by Diziet on Sep 17, 2017
BDSM

This is a follow on from Second Time Around: Ch 1. Apologies for the shortness of the previous submission, this one is longer. Again, thank you for reading and any feedback would be greatly appreciated :) So the story so far... Christina and Dan have met up for the first time in several years, they used to date and Christina was the dominant one, however th...

Pillow Top

by MandolinRain on Sep 16, 2017
BDSM

"Am I ready, Master?" She did a slow spin, arms a bit spread, teasing grin on her face. The black velvet skirt was cut high on her thigh, the emerald green silk shirt elegant and lovely. Seamed black stockings bridged the gap between skirt hem and the ruthless height of the black velvet pumps. The teasing grin was because this had been a ritual of theirs...

Horse Riding

by lfullback on Sep 19, 2017
Toys & Masturbation

Let me tell you a little story about the girl down the hall from me. She always seemed like the nice, wholesome girl next door. She was smart, reserved, prim and proper. In a word, people described her as "innocent." However, I learned a few years ago that the ones you think are the most innocent might just be the wildest. It was my sophomore year of colleg...

Paradiso Ch. 10

by SlyKink on Sep 19, 2017
Fetish

Day 3 Continued Sara and I arrived at the spa a half an hour after leaving our room. It was still early and there weren't many people out in public fucking just yet, even though it was shaping up to be a beautiful day. We stopped only once to watch a foursome consisting of two men and two women, none of whom wore anklets. One pair was going at it missionary...

Alternative Therapy

by evil_from_cssa on Sep 14, 2017
Celebrities & Fan Fiction

The sun had sat on another Los Angeles day and Bridgit Mendler was ready to hit the town, if only she could decide what to wear. Her room was a mess with clothing everywhere as she tossed one top to the side along with another skirt that didn't quite look right. Bridgit put her hands on her hips and sighed, she just couldn't find anything to wear. She looke...

Saint or Slut?

by firehorse8 on Sep 14, 2017
Erotic Couplings

Dedicated to my gorgeous wife J, whose recent 'secret' visit to Paris was inspirational. ***** My hot-shot wife just got came back from a week's training with her company. Actually I think it was more of a reward for her performance than a real training program. It's not the first time she's been away like this, and when she's away I often wonder who she's...

A Vacation To Remember Ch. 04

by masked_maiden on Sep 16, 2017
Celebrities & Fan Fiction

The phone rang waking Heather up she heard Sara answer it. "Really? Okay you can just send him right up." Heather's voice was muffled s she spoke though the pillow and Blankets. Who's being sent up?" "Oh no one just a young man with flowers, a shirt, oh and your glasses. So now I guess well get some answers." Heather rolled her eyes and tried to get up....