Wedgie Boy Stories

105,330 results
Orientation
Length
Source
Infinite Scroll

Enjoy the Silence

by Ironnick on Oct 14, 2017
Sci-Fi & Fantasy

Jeremy strolled into the busy coffee shop. He looked around at the customers and smiled smugly. It was a target rich environment. He went to the counter and ordered a large coffee with a shot of espresso. After receiving his drink, he concentrated then everything went silent. Jeremy had a special gift. He could stop time. Time was not really stopped, more...

The Ultimate Smother

by hithere222 on Sep 12, 2017
Fetish

Samuel gracefully rolled over in his bed, flashing his eyes open to take in his surroundings. Closing them again, he quickly yanked them open, gasping at the sight. His bed was enormous, his pillow giant enough to engulf him, and his clothes had not shrunken to his size, leaving him wrapped in his shirt. He struggled and fought his way out, and surfaced, try...

Project Alice

by FemFreak on Jun 4, 2019
Transgender & Crossdressers

Summary: A female doctor administers the first phase of a clinical study to reduce crime rates by taking potential male criminals who fit certain traits and feminizing them into obedient girls. This includes a physical workout, and testing the sexual boundaries of the subject to encourage feminine rolls during sex. ~~~~~ The subject's name was Stanley Lan...

Becoming the Neighbor's Wife

by marriedhubbi on Sep 13, 2017
Transsexuals & Crossdressers

I like my neighbors and I am grateful for the way we look out for each other. Take Tony, the 60 year old, barrel-chested guy who lives alone in the house next to me. My garage faces Tony's house, and a couple of times last fall he came over to warn me that my garage door was left open. I thanked Tony each time he came over to tell me. One time he came ov...

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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College Life: Panty Thief UnMasked

by MadisonRoux on Nov 27, 2017
Fetish

It all started in my dorm room with my missing thong. . . You know how weird things tend to happen in college? How one day you are walking to class and a drunk student runs through the campus in a banana costume or worse butt-naked! All those stories you see from all the college life snaps that you never thought could happen to you! I never thought I would...

Danielle's Life Ch. 01

by chasingDan on Sep 12, 2017
Interracial Love

Brett and I have been married for 4 years now. We are both very sexual people and have an open marriage of sorts. We don't get downright destructive or vindictive of each other, but we are just basically a really horny couple and just about anything goes. Brett is a handsome guy about 5'10" and slender with an average build. He has a great ass and his cock i...

Expectations be Damned Ch. 02

by Angelpenpal on May 18, 2020
Transgender & Crossdressers

I woke up with that gross feeling of makeup left on overnight. The warmth of my sweet seducers was nowhere to be found. In fact, it was quite cold as the covers were gone. As I attempted to reach for them I found my situation had changed quite a bit since my last moment of wakefulness. I was tied to the bed, hands over my head and feet stretched to the lowe...