Wedgie Punishment Stories

31,807 results
Orientation
Length
Source
Infinite Scroll

Mistress Encounter

by WellBehavedMan on Sep 15, 2017
Fetish

Eva gets back to her hotel room from her business meeting, glad to be back, the meeting went ok, could've been better, they could all be better she reminds herself, as people don't give everything for nothing. As she flicks on the main lights she jumps as she see's you on her soft double bed, right where she left you before she went out, however she did not...

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....

Touhou Mind Control

by plorbus on Nov 22, 2020
Fan Fiction

This story is fiction! All characters are over the age of 18. Gensokyo is a land of possibilities and opportunities, even for a lowly mundane human such as yourself. At the very least, strange things can happen and fortunes can change. You are down on your luck, at your lowest, but things are really about to turn around. You find yourself in the local pawn s...

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House-Sitting Panty Lover Pt. 03

by sissydn on Sep 13, 2017
Transsexuals & Crossdressers

... As I stood there in the parking lot I felt like all eyes were on me. But why wouldn't they be? I had substantially bigger breasts than the average busty girl and were wearing a skirt shorter than that of the high school slut. As I had been standing still for a moment Megan got impatient. "Come on pretty. Don't let me get over there and grab your thong...

Teresa Scalia: Magical Mystery Tour

by obo on Aug 31, 2017
Humor & Satire

Teresa and Dominic Scalia were busily brainstorming entertainment ideas for the upcoming Community Chest gala. "We've got the band with a featured singer, but I think we need something else. Something for a change of pace." said Teresa. Dominic thought for a moment. "How about a magician? It could be the first act right after dinner and before we clear the...

Beneficially HIS

by lil_elvis_lover on Sep 16, 2017
BDSM

Author’s Note: This is a retelling (from the woman’s point of view) of my husband’s (Lime) story, “The Benefits of Reading,” so if it seems familiar, please bear with me. Yes, I admit it. I’m a slut, but not a drop to my knees for any hard cock slut. No, I’m his slut, my husband’s slut, George’s slut. But it’s our secret. Walking down the street, everyone...

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...

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...

Bliss

by IreneXXX on Sep 14, 2017
Erotic Couplings

His meeting took longer than expected and he was late picking me up. Nonetheless I was glad to see him after his busy week. He looked really tired. I was worried that he'd be exhausted since he'd just had a long day at work. But he insisted he was fine and despite a headache, wanted to dance, too. We were supposed to meet 2 girlfriends at Brix, so he decided...