Wedgie Orgasm Stories

207,473 results
Orientation
Length
Source
Infinite Scroll

Jeanie with the Light Brown Hair

by acgolf on Sep 17, 2017
Loving Wives

story I am about to post was written as a contest entry. The rules of the contest were to use the inspiration of the picture of a kneeling woman clothed only in shear thy high stockings and a white feather boa draped over her shoulders. There was a caption under the picture, "you want me to do what? with this boa?" that had to be used somewhere in the story....

The Visitor

by awin9696 on Jul 3, 2018
BDSM

------HIM------ As you type this message I am already behind you. You don't see me. You feel only my hands grapping you. It's too late for you. I use force and throw you into the wall and I put my big body against you. You can't move as my hand reaches down, get a good grab of your underwear and pull it up. You start asking for pity. "You little bitch cun...

The Lady and the Fat Man

by mstrhole on Sep 16, 2017
Fetish

A number of years ago, I knew a woman (on-line) from Germany who had a very (to me) peculiar fetish. She was a zaftig blond who could have been a stand-in for any Valkyrie Maiden swooping down on some ancient Norse battle field, plucking fallen warriors and transporting them to Valhalla. She was also a prostitute. A large (but not fat) woman herself, she was...

Her Panties and a Wet Spot

by daves40004 on Sep 18, 2017
Toys & Masturbation

Jennifer heard the office door open along with a male voice, "I can't imagine what was going through her mind...I mean, seriously, who exercises in a public gym wearing a thong leotard?" Jennifer's hands froze over her keyboard. She recognized Joe's voice. Another male voice responded, "Was she wearing tights or something underneath?" That voice belonged to...

Home Movies with Patsy

by LitEroCat on Sep 1, 2017
Exhibitionist & Voyeur

This story was hijacked, or maybe even inspired without my knowledge, by my WONDERFUL, GENEROUS, BEAUTIFUL AND DISCRETE(?) Muse, Lois. Right, my goddess? ARE YOU LISTENING? "I'm ALWAYS listening. Flattery will get you EVERYwhere." "I'm so whipped! And I don't get any tail from you" "Don't you wish? Get on with the story I gave you." "Yes, my idol." Grrrr...

Jessica's Change Management Ch. 27

by Cathartico on Oct 19, 2020
Exhibitionist & Voyeur

-- Saturday -- This was it! The grand finale was hitting the home stretch! Time for a status update. It was make-or-break time, 'cause I was down a buncha scores. It was all-or-nothing, 'cause I had totally gotten outmaneuvered by Ortega. Despite everything that had happened, the task was still the same. I had to broker new contacts for LGZ. The goal was...

Stephanie Wants to be Seen Pt. 01

by alittlecloser69 on Sep 26, 2017
Exhibitionist & Voyeur

She sat there quietly contemplating how she had gotten to this point. She knew what she was about to do was risky, but she couldn't help herself. She loved the thrill. The chills that she got deep down in her bones every time she got away with it were what gave her an indescribable high. She waited patiently in front of her high school for the beginning of t...

Doubleheader

by wickedlorelei on Sep 13, 2017
BDSM

The Cubs were losing the game 9-4, and it was the bottom of the 7th. A rally looked unlikely. The players seemed to just be going through the motions today. Considering that it was the second game of a doubleheader against the Cardinals and the temperature was in the 90s in St. Louis, Anya couldn't really blame them, and it was nice to be watching the game...

Sally's First

by sally_spandex on Sep 16, 2017
Transsexuals & Crossdressers

My heart was racing a mile a minute as my hand reached for the door knob to open a whole new world to me. Altho I had been dressing for about 15 years, at 23 I still hadn't been outside or let anyone in on my secret. The last 3 years had been hell for me as I had started to play with dildo's and catching my cum in my open mouth, and craving the load of ano...

Book Store Slut

by fuckup77 on Aug 19, 2017
Exhibitionist & Voyeur

Henry always was fairly shy. Always scared to reveal his true self to the world. Terrified to find out exactly what the rest of the world might think of him. 6' tall, combed back shaggy hair, and a relatively average body. Never overly popular with the ladies, but still some experience. Henry worked at a local bookstore. One of the most exciting moments of...