Wedgie Dare Stories

42,476 results
Orientation
Length
Source
Infinite Scroll

She Sucks She Cock by the Sea Shore

by FredTR on May 21, 2019
Transgender & Crossdressers

It felt like it had been years since Liz had been able to take a day and just relax. Her first year at college had been a whirlwind of papers, tests and classes. And her job at the bookstore. Sure she'd gotten laid a few times (okay, maybe more than "a few" times), but that just seemed to stress her out more because she always felt guilty and worried her boy...

Ms. Jiggles Ch. 04

by Cappadonna on Sep 25, 2017
Mature

Halloween was approaching, and Ms. Jiggles could not wait to play dress up. Whenever she showed up to a costume party, women kept a close eye on their boyfriends. She always found that funny since their men would always make their way to her anyway, trying to sneak in some conversation. One Halloween she was dressed as an "Ass Goddess." One person, thought...

Make Me Believe

by northcountrylass on Sep 13, 2017
Anal

I was in the kitchen cleaning up when you got home from work. I heard you come through the front door, and I tried hard to stay focused on the task at hand and pretend as though I hadn't been waiting for you to come home all day. It was a blatant lie, of course, and my clothing fairly well advertised the fact. After all, who cleans kitchens in flirty, ruffly...

Jeff's Business Trip

by seasparks on Sep 13, 2017
Erotic Couplings

It started out just like all the other days in the office. Nothing exciting. Same old same old. Then the boss called me into his office. "Listen up Smith, I need someone to go to Arizona and check out some property that the firm is interested in buying. I picked you. Pick up your company credit card and tickets from Candy down in Accounting. I want you bac...

Unbelievable

by hotmann on Sep 19, 2017
Group Sex

Looking back, it was just like every other night, but due to the random occurrences, turned into a night to remember. I mean, I'd done the same thing 100 other nights during college, but just for one night, the laws of probability got thrown out the window, and I did something that every red-blooded American guy dreams about. Like I said, it started like ev...

My Girlfriend's Sister Pt. 01

by NoblePursuit9 on Aug 13, 2019
Fetish

So it's a typical lazy day off weekday for me. I'm in an old t-shirt and mesh gym shorts playing some video games. It's a scorching summer day out and I want absolutely nothing to do with it, and I have been addicted to this game for days so my butt will be glued to the floor for the remainder of the day in my happy place. Every hour seems to pass faster tha...

Aubrey and the Sorority

by yesplease17 on Oct 6, 2020
Exhibitionist & Voyeur

"Form a line, bitches!" Aubrey found herself somewhere in the middle. She waited timidly at attention with the rest of the sorority recruits. Their leader, Chloe, an older redhead in a pink undershirt and shorts, strutted down the line as if it were boot camp. "Over the course of this week, you'll be expected to prove yourself and support your future siste...

Life of Leigh Ch. 01

by Lee_Bee on Sep 1, 2017
Erotic Couplings

Authors Note: So this is a true story but I do have to change some things so that it's not blatantly obvious who I am and where I'm from. Contrary to popular thought Canada is actually a pretty big place and that's as specific as I'm getting. I would also like to forewarn people that where this is my life, a real life, not everything works out the way you wa...

Sissy Secrets

by DawnCutie on Feb 26, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Every Sissy is just a cross-dresser until someone stronger takes advantage of them. Either they give themselves to a Dom or a Dom takes control of them. This is my story of how my dom found me and turned my life into what it is now. If you're not a sissy let me tell you how we...

Hormone Hijinks

by TheCanadian on Aug 26, 2018
Miscellaneous

Travis wandered through the Megamart, heading on a roundabout path to the men's clothing department. He did it on purpose, cutting into the smaller aisles through the petites and women's departments, subtly sneaking peeks into the racks and displays of sleepwear, lingerie, and panties and bras of all sizes. Like other teenage guys, he already had a consuming...

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