Wedgie Punishment Stories

31,807 results
Orientation
Length
Source
Infinite Scroll

Sister Catfight

by JingleheimerSchmidt on Oct 13, 2014
BDSM

It's a hot July day. There are two sisters hanging out in their house, Jena and Riley. Jena is 18, 5' 1", Chestnut hair, fairly skinny with B-Cup breasts and a small but firm ass. She's wearing a pair of pink and white striped panties and a black camisole. Her Sister Riley is 19, 5' 7", Strawberry Blonde, she has a very well toned body with D-Cup b...

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Faced

by Ailsie on Nov 4, 2019
Fetish

This next match was one that I actually helped set up. It was a friendly bout between myself and another one of the other women in the circuit. She was having a bit of a rough patch, so I offered, well, an easier match up. Myself. At this point, I'd actually won a few matches, so I wasn't entirely on a losing streak. So it was arranged. For this one I actu...

Death by Cupid

by gldngolfer on Sep 17, 2017
Loving Wives

Here is another quick and dirty for the BTB crowd. I tried to throw a little humor in it just to lighten it up a bit. There is mention of one of my favorite StangStar06 stories. For those who read his stories, you will know what I am referring to. I beg his forgiveness if he takes offense, but thanks for a wonderful set up. No persons or animals were harme...

Sensual Weekend Getaway Ch. 04

by Sexy_Boy_90 on Sep 28, 2020
Exhibitionist & Voyeur

Hannah and Brandi walked me back to their hotel room and made sure I was visible for anyone to see in only my red thong. As soon as I entered the room, Hannah glared at me. "I hope you're not ignoring the dress code!" she exclaimed. "No, ma'am," I replied and slipped out of my thong, once again completely naked. Brandi grabbed it from the floor. Hannah sat...

Sailor Moon Ch. 02

by embarrassednakedmale on Feb 3, 2020
Transgender & Crossdressers

The alarm had been buzzing for a solid two minutes when a bleary-eyed Scott finally rolled over and slammed his hand down on the offending device. The harsh noise ceased immediately, and Scott groaned as he rolled back again and cautiously stared at the ceiling. It was still dark in his bedroom, although a single beam of light cut through a tiny gap in his...

Young Guy Goes To College Ch. 05

by pantysubsissy on Sep 26, 2017
Transsexuals & Crossdressers

Sorry that this took so long to post. I will try to get the next chapter out quicker if there is positive response. * The sound of my sister Robin and her incredibly hot roommate Kelly coming down the stairs to my hopefully new girlfriend, Julie's room had me scared to death. It's not that either one of them scared me but it was the predicament that I was...

Stacey Tries Out Bondage Ch. 02

by storytime90 on Sep 26, 2017
BDSM

Sorry for the extremely slow second chapter, I haven't really had any ideas or time to do in but I got a night this week to write this up and hope you enjoy it. If you have any ideas of what you would like to see happen in the next chapters leave a comment. ***** After a couple of uneventful days and trying not to think about what happened during work hou...

Chelsea's Humiliating Misadventures

by Arlingtonc on Sep 26, 2017
Fetish

It's been a long day for Chelsea Arlington, the leader of the cheerleaders, prom queen and (known to everybody since their first day at school) queen bee of the Clayton high-school. The 5'9" 20-year old blonde bombshell, right now approaching her white Mercedes S-class, spend the whole day dealing with this disgusting bunch of so-called teachers, actual...

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Debbi's Shameful Exposures

by enthusiast on Jan 4, 2018
Exhibitionist & Voyeur

At the age of 26, Debbi seemed to have it made. She had risen to be Team Leader in her I.T. company and seemed destined for great things. She had worked hard but it was also true to say that her progress had certainly not been hampered by her good looks. A very pretty petite brunette, she was happy with her small but well proportioned breasts and while she h...

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Beach Interlude

by meltwater on Sep 14, 2017
Erotic Couplings

You close your eyes I'm standing behind you my arm comes round your waist and across your stomach. I kiss your neck as my hand trails lower reaching down; I undo your jeans letting them drop. My fingertips lightly brush the front of your thighs as they teasingly get nearer I proceed to nibble on Your ear as my hand finds your panties and slips beneath. T...