Wedgie Boy Stories

105,330 results
Orientation
Length
Source
Infinite Scroll

The Game

by charlotsky on Sep 16, 2017
BDSM

'Am I awake, or am I sleeping. I can't move... And, where am I?' I became suddenly aware that I was finally awake, but what happened? I find myself naked, gagged and blindfolded. I am strapped facing a device of some sort, in the form of a large 'X' leaning slightly forward; my hands spread and strapped above my head, and my legs spread and strapped. There...

Mistress J

by kotori on Sep 17, 2017
BDSM

It all starts innocently enough, with kissing of course. On the mouth, on the ears, on the cheeks and the eyelids. Gentle nibbles and licks of her tongue and lips. Meanwhile, the hands are roaming, caressing and fondling: shoulders and arms, hips and breasts. You let me undress you as this commences, so those kisses slowly move down from lips to chin to neck...

Christopher and Melissa

by WilkesMistress on Sep 13, 2017
Romance

Christopher Richman. He was without a doubt the most irascible, intractable man she had ever known. Why else would he persecute her so, skulking around her stage door, always with that same amused smile lifting the corners of his immaculately trimmed mustache? They'd hardly spoken in over a year, so what had excited this new attention, this grand patronizi...

Back In The Swing Ch. 03

by Rings3 on Sep 13, 2017
Fetish

The atmosphere in the beachhouse was electric, the four had woken earlier, showered and were once again in "Beachhouse Gear", on the deck sipping ice cold beers. Earlier Garry, Mia and Justin had suckled Sorrell to relieve her milk heavy breasts, there had been some surreptitious fondling and all were feeling quite frisky, the boys were evidently semi hard a...

Shadow Lake Estates Ch. 04

by swingerjoe on Sep 17, 2017
Loving Wives

"There he goes again," Hank noted. The old man held a pair of binoculars to his eyes as he peered through his window from behind the curtain. He checked his watch. "Like clockwork. Every Tuesday and Thursday." Patty shook her head and returned to her knitting. "Such a shame," she said. "Shame?" Hank responded. "These people have no shame. They're like a bu...

My Northern WI Vacation Ch. 02

by alexjackson on Aug 16, 2017
Exhibitionist & Voyeur

=== Part II === I made my way downstairs for breakfast around 7:15. The one thing I did like about working at my grandmother's over the last four days was that she let me sleep in. Now, 7 may not sound like sleeping in, especially since I'm a college student, but I've always had a hard time sleeping past 6. The days work, however, kept me busy enough that I...

Mancation

by jomar on Sep 17, 2017
Group Sex

It came to me at 2:17am while I was watching the 1974 British Open highlights on ESPN23. I was in a rut. I was bored. I needed some excitement. My job was going well, but was on autopilot for now. I wasn't dating anyone steadily, and with the cold and amount of snow outside I might as well be hibernating. I desperately needed something. I was about to go t...

A Hot Summer Night

by Moistlips on Sep 12, 2017
Exhibitionist & Voyeur

Rebecca arrived home after work and quickly went to the air conditioner and flicked the switch to the 'on' position. The heat outside had risen to well over 100 degrees in the Arizona desert and her mobile home was hotter then hell. She felt a drop of sweat run down between her breasts and another quickly followed. Dropping her purse, then pieces of clothing...

Trans Dork Love

by PrettyJana on Sep 16, 2017
Transsexuals & Crossdressers

He pulls my shirt down with his teeth; he’s cute like that. I smile at him as my breasts come free. “Love ya’ sexy babe,” I tell him. He winks and goes back to work. I look over at his shirt carelessly tossed to the floor and then back to him, his smooth chest, god, so sexy, I love it. His pecks stand out subtly and I feel the smooth bumps and dips that...

Innocence Lost Ch. 21

by bradley_stoke on Sep 14, 2017
Novels and Novellas

In Which Leon rediscovers Innocence; and Honore is introduced to virtues beyond the normal condition. Leon never enjoyed his visits to the city of Congress whenever they were necessary. He was very uncomfortable squeezing his enormous penis into the leg of his trousers - even though he always made a point of wearing them very baggy irrespective of how fashi...