Wedgie Girl Stories

196,722 results
Orientation
Length
Source
Infinite Scroll

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...

Just Across the Hall Pt. 04

by EROTICbearscribe on Aug 6, 2019
Transgender & Crossdressers

Chapter Five ACCEPTANCE The assortment of clothes in my pink suitcase reflected my taste and my curiosity about feminine attire but I didn't own a lot of things. Not as much as I would have liked, anyway, especially at this very moment. That is to say, I didn't own any 'sexy' lingerie. Or, what, in my mind would be considered sexy. It was just I never fel...

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...

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...

Mom Makes My Bully into My Boss

by I_Love_MILF on Jul 8, 2019
Mature

My mom, Charlotte, was the owner of The Fan, a popular sports bar where I earned extra money for my college classes working as a busboy. She decided to promote me to a managerial position, and as such, we put out an ad for a new busboy to fill my old position. My mother went through potential applicants, and to my horror, the last person interviewed was Todd...

Best Summer Job Ever!

by amaleSwitch on Nov 7, 2017
Fetish

For 30 days so far this summer my job as a lifeguard at Spankas County Country Club had sucked. Stuck with the early shift it was my job to watch the pool from 6AM to noon and clean the men's changing room and toilets both before and after my stint on the pool. Needless to say it wasn't quite what I envisioned when I applied for the job. All the hot girls in...

Those Jeans Don't Fit

by whostheboss on Sep 12, 2017
Anal

Molly lies on the bed, wiggling her way into her new pair of jeans. "Almost there," she grunts. She's got this habit of buying clothes online that don't quite fit her, but she never wants to declare defeat. She's squeezed the button shut somehow and jumps up from the bed. She's got a bowlegged stance and looks pretty uncomfortable. "Not bad, right?" she say...

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...

Doubleheader

by wickedlorelei on Sep 13, 2017
BDSM

The Cubs were losing the game 9-4, and it was the bottom of the 7th. A rally looked unlikely. The players seemed to just be going through the motions today. Considering that it was the second game of a doubleheader against the Cardinals and the temperature was in the 90s in St. Louis, Anya couldn't really blame them, and it was nice to be watching the game...

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...