Wedgie Dare Stories

42,476 results
Orientation
Length
Source
Infinite Scroll

Archer's Lane Case 01 Ch. 01

by KatPissinger on Oct 30, 2018
Non-Erotic

1 "Wanted: Typist and editor in full time employment. Perfect English and German language skills are a requirement, both in writing and speech. Room and board may be provided. If interested, respond to this paper under No 434/23" Eliza put down the Anzeiger and circled the ad with a pencil. If this was what it sounded like, it might be the best offer she h...

Jaime and Mike Pt. 01

by LadyMelodyDarkheart on Nov 20, 2018
Transgender & Crossdressers

This is my first story but not my last. More to come in this saga. *** It was 3 days before Halloween, and as usual, being a chef, I was going to have to work that night. Fortunately, there was a party this evening at a local club and I was set to go. I had found an old tux with tails in a second hand shop and after I'd done my sugar skull make up, I was...

Mystery Lover

by Writerly417 on Aug 13, 2019
Loving Wives

I'm worried about my marriage. I love my husband and he loves me. In most ways we get along fine, we care deeply about each other. But our sex life has left both of us frustrated. Rick is 33, I'm 32. We've been married five years, we've been talking about having a baby. But should we bring a child into a marriage like this? One that, I have to say, might no...

Hot and bothered

by nothingisalways on Aug 20, 2019
Erotic Couplings

I admire the hell out of my wife's vagina. I mean, three of my kids have slid out of it- three times she's swelled up like the legendary victim of a swallowed watermelon seed, past the point where I started to feel panic stricken when I imagined the process by which the thing had to make its way out of her. But she'll just smile all serene and stroke her bel...

Sissy Arlene's Soul Mate Ch. 02

by SissyArlene on Jul 10, 2019
Transgender & Crossdressers

Note to reader; This is part of the ongoing story of sissy Arlene. To get a full sense of this Saga, you need to read the 3 parts of "SIssy Wants Her Wife's Boyfriend," and then read "Sissy Arlene's Soul Mate." And now, "Sissy Arlene's Soul Mate chapter 2." ***** I awoke to the smell of coffee and bacon. My first thought was that my wife had slipped out...

Private Self Ch. 03

by Lustymarriedmomcantgetenough on Dec 11, 2018
Erotic Couplings

A thank you again to my reliable and trusted editor, who wishes to remain anonymous. Also, thank you to all the readers who have sent me encouragement to keep writing. If you leave a comment, I will let you know when next chapters are available! (For me to contact you, I must know your Lit username, and you must opt to receive PMs) I hope that you enjoy thi...

Fat Blob, Hot Asian, White Stud

by godzillastail on Nov 27, 2018
Exhibitionist & Voyeur

Bob Rosenberg worked as a lowly paralegal at a law firm. He was once a powerful movie producer. But he had lost that position and done a stint in prison because he was a fat, ugly, and sexually frustrated blob who had tried to force his fat, disgusting self on women who were actually good-looking and wanted nothing to do with someone as hideous as him. After...

Wastelands Vixen Pt. 01

by johnharem on Apr 8, 2019
Sci-Fi & Fantasy

The leather seats burned her bottom as she drove. She shifted gears and the car blasted over the blacktop. She didn't know where the road would take her, but it was the only road around so she had no choice. Nothing but sand dunes around her, as far as the eye could see. She looked at the fuel gauge with sorrow. Unless she found something soon, this was goi...

The Commissar's in Town Ch. 03

by SEVERUSMAX on Jul 10, 2018
First Time

"Wow, that was quite the supper, Trudy, I must confess! And you say that I can bring some home to Dad? That would be very lovely if possible. I imagine that by now, he's rather worried about his future now that I have no job, if he's heard about it, which he might have by this point," Sasha reacted to the wonderful pot roast and dry red wine that she enjoyed...

Keeping the Bailiffs away Turns Fun

by goldcloak on Apr 10, 2019
Fetish

It was the last few weeks of term. I had done all my exams at school and I was only going in to finish off final assignments. The pressure was off and university was only two months away. It was a hot day and I couldn't wait to get out of this uniform. We had to wear these cheap white polyester shirts and a yellow and blue school tie. We also had a choice...