Pillow Hump Stories

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Orientation
Length
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Infinite Scroll

Freddie Gives Gayle Anal

by BOSTONFICTIONWRITER on Sep 14, 2017
Anal

"Hi, Freddie." "Oh, hi Vinnie." "What's wrong? You look down in the dumps." "I'm stuck writing a story." "You? Stuck? Are you kidding me? You've written a million stories already. You've written so many stories that I can't keep up with you. It makes my head hurt to read that much. Besides, I had to take a break because my finger is blistered from going...

Crossdresser's Rassling Dreams

by footqueen99 on Sep 17, 2017
Fetish

The following is an email chain between two crossdresser's who enjoy wrestling. All persons depicted in this writing are well over 18 years old. ***** I wish i could have been there! I would love to see a few pics if u can share. I love pro style fantasy matches. I love all the holds, drama, trash talking and victory poses where u pose with your stocking...

Another Day at the Office

by evesdream on Sep 17, 2017
BDSM

This scenario was written in honour of a friend’s entrepreneurial scheme, his infectious obsession with the "sexual underclass" of New York and a sex toy known as the Real Doll. **************** "How many men have you fucked today?" "....9...?" "10. And it isn't noon yet. What does that make you?" "...a whore." "A fuck-ing ho." Bored female voice ove...

The Pillow

by dscott1947 on Sep 16, 2017
Toys & Masturbation

Copyright 2007 by Dwight Scott All rights reserved. Other than downloading one copy for strictly personal enjoyment, no part of this story may be reproduced or transmitted in any form or by any means, electronic or mechanical, except for reviews, without the written permission of the author. However based on real events and places, "The Pillow" is completel...

Let's Edge Together Ch. 01

by Appl3bottom24 on Apr 9, 2019
Erotic Couplings

A few days ago, I reposted a point system to earn my orgasms. I was so excited to try it! I ended up not doing it alone. One of my lovely followers decided to help me earn points, added some new ways to earn points, and coached me through my edging. Now I'm going to share with you how my morning went... To begin, he had me smack my clit 30 times to wake me...

Baby Sister Ch. 11: BUTTercUP

by SZENSEI on Aug 24, 2020
Exhibitionist & Voyeur

"I do not want to be a girl anymore. I want to be a woman." Maria Blanco threw a tantrum while following her stepbrother Owen Barnett through their mansion home in the bowels of Texas. He had taken her virginity two nights before and had warned her that there was more than just losing her virginity to being a woman. In her naivety at knowing pretty much not...

The Crowd

by SillySexter on Mar 31, 2020
Exhibitionist & Voyeur

My mouth is currently on your dick. And it’s fucking SUCKING IT!!!! (The crowd ooosand aaahs) (I give them a thumbs up without stopping!) Isn’t it great to know the crowd’s impressed?! Then I say “lets go somewhere more private” and stand up and pull you into a private room backstage not too removed from the crowd’s earshot. We find a comfy beanbag!!!!! (Isn...

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Sweet Surrender Ch. 03

by mdp_2004 on Sep 16, 2017
Transsexuals & Crossdressers

Nikki inhaled sharply and said "get the fuck off me." I hesitated, unsure that she meant what I heard. "Now baby, get up. I want to fuck the shit out of you." Her lust took hold of both of us and I acquiesced. On withdrawing, the air inside her popped as my cock came out. What's that smell? Oh my god, her shit is on my cock. "I need to go clean up" I said a...

PeePillow TM Pt. 02

by kayleekennicott on Sep 25, 2017
Fetish

After I chugged a couple glasses of water and was ready to go again, I carefully balanced the webcam on the corner of my bed, setting up the PeePillow and correcting for proper angles. I wanted viewers to see me from the shoulders down, while keeping my face from view and preserving a bit of anonymity. So when I was ready, and my fingers were tingling a lit...

Was It Worth It? Ch.02

by Rbk_47 on Nov 24, 2017
Toys & Masturbation

This is the second chapter of the 'Was It Worth It?' series. I'd recommend reading the first chapter before proceeding with this. This chapter introduces a few new characters that'll hopefully spice things up. Enjoy! And apologies for the slightly long wait. I'll try to be faster with the third chapter. P.S. All the characters in this story are 18 years and...