Gay Wedgie Stories

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Orientation
Length
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Infinite Scroll

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...

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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Now and Then

by Jim_and_Sarah on Sep 16, 2017
BDSM

Now. I stand under the needling hot spray until the water starts to cool, and shut it off, and push the wide glass door open to release billows of steam. Drip and splash across the wide marble floor and wipe a clear circle on the mirror with a thick white towel. Behind me the sun is trying, and failing, to pierce the overcast. Not likely in February. We're h...

Blood & Magic Ch. 12

by bbettyblambabam on Sep 19, 2017
Erotic Horror

Kirstin walked into the department feeling on edge, her eyes scanning coworkers she passed by, looking for any smirks, raised eyebrows, quick avoiding glances, anything that might hint at Alan sharing the story of her humiliating experience at the warehouse. She almost bumped into people due to focusing her attention on listening rather than what was in fron...

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...