Gay Wedgie Stories

23,007 results
Orientation
Length
Source
Infinite Scroll

Black Fantasy Fulfilled Three Times

by HotWildcat on Sep 13, 2017
Interracial Love

Black Fantasy fulfilled three times, part one My husband Tim and I had been married for ten years when we started to find ways to spice things in the bedroom. One night, while reading an article on ways to put the excitement back into sex it talked about sharing fantasies. This is when I shared with him a fantasy I have had since I was sixteen. I told him o...

Doomgirl Ch. 02: My Robe and Wizard

by theonethatdiditnot on Dec 24, 2019
NonHuman

The surefire way to take a Possessed out of action, other than blowing their brains out, was to make them cum. The four dicks of the Possessed on the ground around me would eventually harden again. They would wake up and pursue the next person to fuck. As much as I loved getting fucked silly, I wasn't planning on sticking around to be their fucktoy for any l...

Tinder Pt. 02

by TwistedPanties on Jan 22, 2020
Transgender & Crossdressers

I appreciate you all asking me for more of the story - It would be hotter if you begged ;) Sissies can be so over-eager... (Keep the feedback coming please, Sweeties) Background: Bryan's roommate Caitlin has just discovered his crossdresser girl Tinder profile, while her friend Allison was swiping for a new girlfriend. Bryan is in the kitchen with a baby...

Teresa Scalia: Riot in the Ring

by obo on Sep 13, 2017
Humor & Satire

Mark Anderson and Dominic Scalia were meeting in Dominic's office planning a major fundraiser for their Men's Club. The club was providing financial assistance and support to construct a new recreation facility for the youth of their city. The event, catering to the more affluent male population, was to be a night of boxing followed by an auction of donated...

A Little Wrestling Match

by Fred1177 on Aug 18, 2017
Fetish

On Tuesday, I was at the office, just another cubicle rat congregating with the other cubicle rats in the snack area. A couple of the women were talking about how they had been doing a little wrestling among themselves. My ears immediately picked up on this conversation. I found out that there were several women from the office who would participate and that...

My Ideal Morning

by atomicrocka on Aug 18, 2017
Fetish

I wake up on a queen sized bed. I was asleep on my back, belly up. I lay on the left side of the bed, and turn my head right to see you, still asleep. We are both under the bed sheets. Quietly, as not to disturb your slumber, I slowly slide the sheets off of me, revealing my sleeping attire. I am wearing nothing but baby blue panties and a white, short sleev...

An Unexpected Swim Ch. 01

by JackRabbit85 on Sep 13, 2017
Romance

I've always been one of those kind of guys that has the unusually high sex drive, and I know most guys will typically think that about themselves but mine has a bit of a twist and reason to it. For as long as I could remember I have been attracted to woman's panties, and for whatever reason... is unknown. But granted I do have my limits to what it is I am at...

Webman

by LexyHarper on Sep 14, 2017
Erotic Couplings

I nursed my fourth glass of Baileys and watched resentfully as my colleague Jewel worked her charm on Niles, the new guy at the office. She was standing so close to him, as he sat on a stool at the bar, her 32F breasts were practically in his face. When she had approached him earlier he had offered her the stool, but she had smilingly declined, knowing that...

Festival of Fucking

by MissyDemeanors on Sep 15, 2017
Group Sex

Hiya!! I enjoy writing stories on request and felt I should share some of my work. A guy requested two strangers hooking up and this is what I came up with. I'm open to constructive criticism just go gentle on the grammar bashing. I'm really working on it. ***** Bridget stuck her thumb out further sighing. Her friend Melonie came running up behind her. "Fl...

Hands-on Experience Ch. 02

by inchXinch on Aug 30, 2017
Fetish

Chapter 2: What Does That Make Me? The next time I saw Daniella, it was incredibly difficult to maintain a professional relationship around our co-workers. I don't think they noticed since the two of us had been developing a close relationship over the last couple years. They simply thought we were becoming best friends, which was true, but now that we had...