Pussy Wedgie Stories

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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...

Caught Relaxing Pt. 01

by StephaniePlayland on Aug 6, 2019
Transgender & Crossdressers

This is going to be a short series of stories. This one really starts the journey out, they won't all be in exact order or have a proper linear flow to them. Just depends on what's has caught my interest that day, and needs to flow out of me. It's Friday night, no plans or anything to do a perfect night to dress up. Hangout have a drink and relax being Ste...

The Freshman

by playbabyf on Sep 13, 2017
Erotic Couplings

I was a dork during high school. Not in looks, or in personality really, but I studied a lot. That was my parents' expectation. So I got good grades. I didn't party. I had a few friends, and they studied a lot and got good grades as well. We were all going to be successful. Of course, I was a little pent-up, so the summer after graduation I had a beer, tried...

Team Day

by Youngandfun22 on Aug 21, 2019
Mature

Living in New England, one can expect one thing during football season, you can expect to see the Patriots in postseason and very likely another consecutive Super-Bowl. Every year, Phillips Academy has a spirit week, and one of those days is "Team Day". This year isn't any different for Joanna, except this year she's finally 18, graduating high school in j...

A Night at the Gym - F/M Mixed

by Notbob8448 on Jul 1, 2019
Fetish

She was introduced as Margot at a party of a mutual friend. She was very attractive and I was thrilled to be introduced to her at first, but her conversation starter was, "You look kind of wimpy." I'm not a big muscular guy, but I'm relatively fit and I get occasional compliments on how I look. I'm pretty confident in my physical abilities. I played footbal...

Jenny's Holiday Income Ch. 02

by StoneKidman on Sep 5, 2017
Fetish

Ch.2: the giant Jenny arched her back up off the mat after she was just slammed again by Giselle. The 6'7" giantess once again hauled my 42 year old girlfriend up by her long, dark hair. Giselle guerrilla pressed Jenny high in the air, one thick hand wrapped around Jenny's throat and the other digging into her crotch. The giant had light brown hair just a...

House-Sitting Panty Lover Pt. 03

by sissydn on Sep 13, 2017
Transsexuals & Crossdressers

... As I stood there in the parking lot I felt like all eyes were on me. But why wouldn't they be? I had substantially bigger breasts than the average busty girl and were wearing a skirt shorter than that of the high school slut. As I had been standing still for a moment Megan got impatient. "Come on pretty. Don't let me get over there and grab your thong...

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...

Under The Table

by Nat_Needs_Humiliation on Apr 15, 2020
Fetish

My friends and I are always making stupid bets with one another, or giving each other juvenile, puerile dares. The stakes vary wildly, from a simple thing like buying someone's dinner to something far less platonic. One forfeit that always sticks in my mind was the time we made Amelia put most of her meal into her knickers to eat later. I remember watching...