Pillow Humping Stories

65,943 results
Orientation
Length
Source
Infinite Scroll

Julie's Big Day Pt. 02

by LaceyDresser on Jul 13, 2020
Mature

Prologue: The below narrative is obviously a continuation of Julie's Big Day, which I recommend reading first, although it isn't absolutely necessary. And please be advised the following documents a sex session between four mature bi-sexual women. If lesbian sex is not your "cup of tea" as the Brits like to say, it might be best to find something else to re...

Tara Ch. 02

by foxxisamms on Sep 17, 2017
Loving Wives

To my surprise I arrived home to find a voice mail from my old college room mate Devon. She'd be in town for a conference and wanted to try and get together for dinner. I smiled knowing Art would be expecting a private little show from Devon and I. Then it occurred to me, why not give Art and Mr. King a show. It would be a "shoe in" for Art's promoton, and I...

Wedgie-Self

by wrbsuperman on Aug 18, 2017
Fetish

~~~This story got rejected 4 times, because the paragraphs were too long and because they thought I was advertising for sites I'd mentioned. I prefer real-world stories that other members of the wedgie fetish community can relate to, and apparently I can't do that. The story isn't the same since all these "revisions" but I hope you can find some enjoyment no...

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...

Twisted Passion

by ScottRichardson on Sep 15, 2017
BDSM

***One*** It's been a long grueling couple of months... On a Friday after coming home from work my wife told me to get cleaned up, shower, shave and brush, just like you were going on a hot date, oh and, make sure to pay special attention down below, "I expect your privates clean and shaved. Oh, and make sure your ass is clean. Let me know when you're do...

Wives on Vacation: Ann's Massage

by sjones on Sep 26, 2017
Interracial Love

"Baby this going to great!" I said as I looked out the airplane's window. "The water is as blue as the sky," I continued, as I gazed down below. My wife, Ann, was seated next to me at the window, and I was leaning across her body as I took in the spectacular scenery. Our jet was on final approach to our island vacation destination. I purposely had a case of...

Best Friends Forever Pt. 08

by Kantarii on Dec 25, 2018
Transgender & Crossdressers

"Flip over..." Those two words come as a surprise, filling my mind with expectations. I find it interesting that Brian wants to switch from doggie style to a more traditional sex position, a romantic one at that. Hopefully, he won't be turned off if he sees my cock while we're having sex. I hope not. Playing with myself is the only sexual joy I have these...

The Cuckquean POV

by edgequean on Sep 14, 2017
BDSM

I am a submissive wife and my husband, Ethan, owns my horny cunt. When we first met, he was generally your average passive guy, except sometimes he can be domineering and condescending to me. It caught me off guard, but I learned to love it. Ethan soon controlled all my orgasms, when I was allowed to cum and in which manner, humiliated or not. He also has th...

Secret Hauntings

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

They told me it was haunted, but I didn’t listen. What can ghosts do to someone who doesn’t believe they exist? It was a small house, once rumoured to have been owned by a young lady who killed herself one night after her lover left her. I didn’t care, the price was right and the house suited my needs so I snatched it up quickly. The realtor said she was g...

Deborah Reel from Agnes Scott

by MasturbationSuperstar on Sep 16, 2017
Letters & Transcripts

Dear Deborah, "First impressions are the most lasting." The first impression you made on me has lasted over 20 years and to this day it is still a strong and powerful one. I still remember the first time I saw you. The April 1991 issue of Playboy magazine arrived in my mailbox and took it along with the rest of my mail up to my apartment. I put the mail on...