https://www.freepornflix.com/categories/wedgies/ Sun, 21 Jun 2026 21:43:55 UTC https://www.freepornflix.com/video/1007661/popular-bully-wedgies-nerd-at-a-party-featuring-violet-vega-and-violescent/
]]> Sun, 21 Jun 2026 10:28:53 UTC https://www.freepornflix.com/video/1007661/popular-bully-wedgies-nerd-at-a-party-featuring-violet-vega-and-violescent/ https://www.freepornflix.com/video/1004583/school-nerd-wedgie-fight-wmv/
In this custom video we start with ryan studying for a test with some nice upskirt shots. laney and charlie barge in and give her a wedgie, which starts a huge wedgie fight with the school girls! ]]> Fri, 19 Jun 2026 11:34:04 UTC https://www.freepornflix.com/video/1004583/school-nerd-wedgie-fight-wmv/ https://www.freepornflix.com/video/1002819/princess-wedgie-fight-ayla-vixen-zara-hidef/
Ayla and zara are tired after a busy night at the biggest ball in kingdom. they dined and dance, met potential suitors and made many new friends. back in their room they are catching up about the night - when they both realize they both have fallen for same prince.  each girl thinks they will win prince charming's heart, but soon a caddy disagreement soon turns into a huge wedgie fight! they start yanking each other's panties up deep into booty cracks. using their strong arm muscles they yank harder and harder.  atomic wedgies oh no! these princess will never be the same... ]]> Fri, 19 Jun 2026 08:54:57 UTC https://www.freepornflix.com/video/1002819/princess-wedgie-fight-ayla-vixen-zara-hidef/ https://www.freepornflix.com/video/999921/comfortable-underwear-ripped-wmv/
Kendra spots paris' comfortable underwear.  she taunts paris til they are torn. ]]> Wed, 17 Jun 2026 11:07:31 UTC https://www.freepornflix.com/video/999921/comfortable-underwear-ripped-wmv/ https://www.freepornflix.com/video/999323/the-wedgie-challenge-orgasm/
The wedgie challenge! you must complete it off you want to cum, i have a timer in my hand and humiliation on my mind! you will do exactly as you are told. but will you cum? it won’t be easy.  ]]> Wed, 17 Jun 2026 10:23:47 UTC https://www.freepornflix.com/video/999323/the-wedgie-challenge-orgasm/ https://www.freepornflix.com/video/998372/comfortable-underwear-ripped/
Kendra spots paris' comfortable underwear.  she taunts paris til they are torn. ]]> Tue, 16 Jun 2026 14:30:07 UTC https://www.freepornflix.com/video/998372/comfortable-underwear-ripped/ https://www.freepornflix.com/video/990536/a-wedge-between-us-pervert-wedgie-punished-jasper-reed/
Jasper thought she had the night off from her life as a dominatrix to enjoy a movie with an old friend. goddess jasper reed took the reins the moment said “friend” came out in tight boxer briefs & nothing else… the male species is nothing if not desperate and disgusting. what kind of game did he think he could play with a seasoned vet like jasper? whatever he may choose, he’ll lose — with a punishment that perfectly suits the crime.  a wimpy nerd in tight little undies, hoping to get his pathetic penis a fabrics distance from a goddess, will get far closer than he ever imagined. punished with the very fabric meant to arouse him, he’ll be bent over, held down by her feet, and wedgied until those little boxers rip into a miniskirt… … & then she’ll use his little flap to keep going.       wedgie wedgies wedgied bully bullies brat brat girls mean girl femdom female domination punishment man wedgied boxer briefs brief ass slapping spanking otk spanking shamed humiliated emasculated dry humped mocked undies ripping emasculate emasculating humiliating humiliatrix humiliation slave training pervert punished  ]]> Sat, 13 Jun 2026 14:06:12 UTC https://www.freepornflix.com/video/990536/a-wedge-between-us-pervert-wedgie-punished-jasper-reed/ https://www.freepornflix.com/video/984878/naughty-student-swirlies-wedgie-punishment-ft-goddess-fina/
Custom clip! hi goddess fina, i am a long time fan and i am very excited to get my own custom! i mainly enjoy wedgie/spanking videos, with soft femdom. i don't enjoy harsh degradation (pathetic, loser, etc.) i prefer playful intimidation (bend that booty over right now!). for this video i would love it if you were my an older authority figure, like a governess. as soon as i return home from university you call me into the living room with a disappointed look. you told me that if my chores weren't done i was going over your knee for a spanking, and you meant it. but you notice my tighty whities are stretched out and hanging out of the back of my pants. you ask what happened, and tell you that a female athlete cornered me in the bathroom and gave me a wedgie. she ordered me to turn around, place my hands on the wall, and stick out my butt. with her muscular arms she hoisted and yanked repeatedly calling me a nerd. she bounced me like a yo-yo and thoroughly flossed my booty. eventually she made me kiss her bare butt, gave me a swirly, and an atomic wedgie to end our bullying session. i was told to leave my wedgie firmly up my bottom for the rest of the day, and to meet her in the bathroom daily. as i tell you the story you repeat back what i say in shock and sympathy. you offer to rub my sore behind, to help pick it out, and demonstrate a wedgie on yourself to show me that its not that bad. finally you tell me that from now on i am to submit my butt for my daily wedgie to my bully without protest. if i comply, she might take it easier on me. to end the video you tell me to get over your knee, even a severe booty flossing doesn't get me out of my spanking punishment. i hope you like my idea goddess fina! please let me know if you'd like to do this and if you have any questions/concerns :)   ]]> Thu, 11 Jun 2026 10:56:12 UTC https://www.freepornflix.com/video/984878/naughty-student-swirlies-wedgie-punishment-ft-goddess-fina/ https://www.freepornflix.com/video/970979/eden-wedgie-humiliated-courtney/
Courtney is admiring how good eden's body has become, as she prepares for the fitness competition. fit and beautiful but what are these that you are wearing. what competitor wears granny panties? she gets humiliated until her panties are torn. (starring eden sins and courtney cummz) ]]> Thu, 04 Jun 2026 10:07:09 UTC https://www.freepornflix.com/video/970979/eden-wedgie-humiliated-courtney/ https://www.freepornflix.com/video/969776/eden-humiliated-courtney/
Courtney is admiring how good eden's body has become, as she prepares for the fitness competition. fit and beautiful but what are these that you are wearing. what competitor wears granny panties? she gets humiliated until her panties are torn. (starring eden sins and courtney cummz) ]]> Wed, 03 Jun 2026 11:02:16 UTC https://www.freepornflix.com/video/969776/eden-humiliated-courtney/ https://www.freepornflix.com/video/968563/wedgies-for-my-roommate/
I have literally had the worst work day ever!! since we have agreed that as roommates, we can take our frustrations out on one another, i desperately need to do it tonight! i am going to destroy your ass by giving you every wedgie i can think of!! i want to put your in a hanging wedgie, i want to squeaky clean wedgie you, and i definitely need to give your a massive atomic wedgie! prepare yourself nerd!! ]]> Wed, 03 Jun 2026 09:36:27 UTC https://www.freepornflix.com/video/968563/wedgies-for-my-roommate/ https://www.freepornflix.com/video/966190/rookie-vs-lingerie-fight-champ-wedgie-trap-undies-between-ass-pussy-lips-jackknife-pin-tap-out-ziva-vs-autumn-pt1/
Lingerie fighting championship star and martial artist ziva fey (5'1" 102 lbs) takes on rookie autumn ehr (5'7" 119 lbs) in an electric, no holds barred topless female wrestling battle. autumn towers over pettite ziva and feels that depite her lack of experince her hight and weight advantage will serve her well. autumn really surprises ziva fey with body scissors and a painful armbar that only serves to anger her foe as she retaliates with a rear naked choke while taking the opportunity to pinch and twist autumn's pert, sensitive nipples. a surprising figure four head scissor submission by autumn leaves ziva wheezing and gasping for air. ziva retaliates with immobilizing grapevine pins, belly punching and forearms across the throat then resorts to wedgies that trap undies in between wet pussy lips. she continues the punishment with facesits and even the biting of tits aren't off limits as the match descends into chao. hair is pulled, body punches thrown, breasts are squeezed and pussy is attacked as these ladies fight to exhaustion in a fierce showdown where only victory matters. a sharp elbow to ziva's ribs turn the tide leaving ziva flat on her back before autumn nearly breaks the loser in half with a jackknife pin submission. ]]> Mon, 01 Jun 2026 11:52:10 UTC https://www.freepornflix.com/video/966190/rookie-vs-lingerie-fight-champ-wedgie-trap-undies-between-ass-pussy-lips-jackknife-pin-tap-out-ziva-vs-autumn-pt1/