The two Bellas are paired up for Team Nightmare going up against Cheyenne Jewel and Penny Barber for Team Dragon. Bella Wilde is the smallest girl on the mats today but she puts up a strong fight in the arm wrestling bout against Cheyenne and holds her ground pretty well the first minute of the match. Syd's coaching from the side lines is really benefiting the team. Dragon doesn't need to do much coaching since her strategy is working perfectly......keep the weak link of team nightmare on the mats for as long as possible.

Francesca Le has the best hand at the poker table and when the girls can't pay their debt she uses her hand to put them over her knee and spank their round bottoms. Sadie Santana and Penny Barber pay their debt anally. They are spread open, Penny is fisted in the ass and her pussy. Both girls are fucked with a giant strap on by the talented Francesca Le

One working over was not enough for this greedy MILF. Penny Barber is legendary for how mouthy she is. This brat needs breaking but always bounces back twice as bratty as before. Jack Hammer decorated Penny with bruises and strict restraint for Infernalrestraints, but it was obvious it was not nearly enough. In the end, he brings her over to Hardtied where Rain DeGrey is waiting to take a crack at her.Once Jack dumps off his used plaything, Rain pounces and gets to work immediately. That mouth has always gotten Penny in trouble. Time to show her the price for insolence. Penny is tightly tied and gets her mouth washed out with soap and water. Her makeup is destroyed in the process but the attitude remains. The soap is shifted into a gag and Penny is left to wallow in soapy anguish as drool pours out around her gag.Pulling our busty MILF into a bent over position, Penny is tied down so that her juicy bubble butt is perfectly exposed. A fierce and relentless flogging on that iron ass doesn’t even get her attention, and Rain has to switch to her fist. The fist does the trick as a noticeably less lippy Penny cums hard, glassy eyed and twitching. Pleasure seems to have more of an impact then pain, and Rain explores that with a merciless strap-on pounding.Evidently pleasure is the key to unlocking this brat, and Rain binds her into a chair tie that perfectly displays that greedy cunt. Penny can not close her legs or shift in the slightest, and is promptly overloaded with with a onslaught of vibrator and fist. As her eyes roll into the back of her head, the sassy backtalk are noticeably absent. Of course, the big black ballgag firmly wedged deep between her lips probably helps too. Once every last orgasm is ripped out, our bound and destroyed fucktoy is left lolling in her ropes, drool pouring out and a distant look in her eyes.

It's coffee time for this group of powerful and influential stock speculators and Penny wants to serve them right - with a little cream and sugar. But that's not all she wants to serve them! These fellas may have met to go over their investment portfolios but soon Penny has made a better offer - investment into all her greedy holes. She's ravaged just like she wants with power hungry cock-sucking, double penetration, and double-vag! The deal ends with her left covered in cum and a briefcase worth of bills!!

Penny Barber and Savanna Fox have gone back and forth on winning and fucking each other. Penny Barber won one match then Savanna fox won a match. This rubber match will finally decide who the meanest bitch is. Who ever wins gets to fuck the loser with the biggest cock Ultimate Surrender has ever seen. Loser is fucked and humiliated like ever before.

All Tony wants to do is watch his game which would be fine except the big game happens to be on Valentines day and his woman, Penny Barber, expects to be wined and dined.

Professor Penny Barber is more than happy to trade grades for sexual favors, IF the young man in question is cute enough and, more importantly, big enough. If what he has in his pants impresses her enough it won't really matter what he has in his head. Her newest candidate for boytoy of the semester, Sam. has an honor roll face but Penny is very disappointed when she makes him unbutton his pants to reveal a D- cock.Penny takes out her annoyance by humiliating the wannabe stud for his inadequate dick. She even makes him fetch a ruler so she can find out exactly how little he is down there. Professor Barber might not have gotten the plaything she was hoping for but she can still amuse herself with mocking him. Verbal humiliation is always more fun when your sitting on your target's face so Penny makes him strip totally naked and lie down facing up. Once Penny has Sam pinned beneath her for some smothering pussy worship she promises to tell every girl in his class exactly how tiny his cock is!Ever since the day Professor Barber made you drop your pants in her office, she has kept your tiny cock a secret in exchange for total obedience. You grade her papers, run her errands, and do any other task she feels is beneath her. Your only reward is the occasional glimpse up her skirt or a pair of dirty panties to sniff. Professor Barber also likes to make you work naked so she can tease your little dick and laugh when you get a boner.Sometimes she makes you jerk-off before she lets you start your chores. She claims it is to help you focus but she really just likes how much it embarrasses you to play with yourself in front of her. Professor Barber might give you a pair of wanking panties as a treat but treats from her are just a humiliation trap waiting to be sprung.

The gorgeous Savannah Fox takes out her two foxy MILF butt sluts to play! Dark haired Penny Barber is so glad to be out of her cage, and super blonde London River is eager to get fucked. First Savannah must make sure each ass is tender. She spanks her toys' asses and takes a deep whiff. She uses Penny's mouth to warm up London's asshole and when Penny gets mouthy, she shoves her head right in between London's cheeks. Then London gets to lick and smell Penny's delicious asshole. Once these two sluts are all warmed up, Savannah breaks out the toys! She starts with the fat, cold stainless steel double ended dildo. She teases Penny with it before plunging it in London's greedy asshole. For Penny's asshole, Savannah chooses a glass corn on the cob dildo. Penny squirms as the cold toy gets pushed slowly in and out of her asshole. These hungry slutholes are aching for more and Savannah knows just how to satisfy them. She has London hold Penny's legs open as she slides her fist right into Penny's ass. Penny screams as the fist slowly sinks into her ass and tries to squirm away, but is unable to escape and made to orgasm on Savannah's fist. Then Penny holds London's legs open as Savannah pushes her fist into London's slutty asshole. Once the fist is in, London can't stop cumming as Savannah fist-fucks her hole. As a reward for being so good, London gets stuffed with Penny's fat cock. London moans as her ass is fucked and Savannah is so turned on, she starts masturbating and fucking her own asshole. The more London screams, the more aroused Savannah is. She squirts all over London, covering her dirty sluts in cum.

Penny Barber is well known for two items: Her gigantic beautiful tits and her big mouth The secret is that Penny does like to submit, but first one has to beat her beyond words. Luckily she comes to Hogtied asking for some marks and to see if she has a limit for orgasms. I was happy to oblige. The first scene find our classic beauty hanging by her jugs, toes barely touching the floor, with a couple pounds on metal hanging off her pink labia. Add a vibrator and some flogging and now we have a babbling Barber. She still managed to sneak in some smart ass remarks, but a flogging on her sore nipples helped with her compliance. In the second scene I bound Penny in a tight kneeling position, tits out and tightly bound for maximum sensitivity. Another ten screaming orgasms in and she found she was no longer committed to finding her orgasm limit, but she was convinced to recommit after a strict caning all over her tight body. This lady can take it! And I am more than happy to give it. The last scene I put a worn out Penny on her back, legs in a spread frogtie, and took her round ass for a ride with two big rubber dicks. She resisted until the very bitter end, but on her umpteenth orgasm she was willing to admit, "I'm a double penetration anal slut MILF!" Finally we agree on something!

Penny Barber is well known for two items: Her gigantic beautiful tits and her big mouth The secret is that Penny does like to submit, but first one has to beat her beyond words. Luckily she comes to Hogtied asking for some marks and to see if she has a limit for orgasms. I was happy to oblige.The first scene find our classic beauty hanging by her jugs, toes barely touching the floor, with a couple pounds on metal hanging off her pink labia. Add a vibrator and some flogging and now we have a babbling Barber. She still managed to sneak in some smart ass remarks, but a flogging on her sore nipples helped with her compliance. In the second scene I bound Penny in a tight kneeling position, tits out and tightly bound for maximum sensitivity. Another ten screaming orgasms in and she found she was no longer committed to finding her orgasm limit, but she was convinced to recommit after a strict caning all over her tight body. This lady can take it! And I am more than happy to give it. The last scene I put a worn out Penny on her back, legs in a spread frogtie, and took her round ass for a ride with two big rubber dicks. She resisted until the very bitter end, but on her umpteenth orgasm she was willing to admit, "I'm a double penetration anal slut MILF!"Finally we agree on something!

Penny Barber had one little problem: her out of control little slut step daughter Mercy West. Using her perfect MILF body and uncontrollable sex appeal to bring Mercy’s punk boyfriend on board for disciplining Mercy, she get’s a little more than she bargained for. After having her juicy round ass spanked a deep red, clamped, flogged, and controlled by Xander’s thick cock, she leaves Xander with a few tools to persuade Mercy with: handcuffs, wax, and a dress for her little princess to where to tea. All lines of dominance eventually meet in confrontation when Mercy starts acting up again, resulting in Xander and Penny teaming up to get that pretty little punk covered in cane marks and her boyfriends huge dick in her tiny virgin ass. With the newly minted little angel lapping at Mommy’s cunt full of her boyfriend’s dick, Mercy learns what it’s like to really earn some cum.

In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who land themselves in county jail for turning tricks and selling drugs. Penny is desperate to get home to her kid and creates animosity between the two of them by claiming to be able to give better sexual favors to the female officer to get out of jail quicker. Officer Aiden Starr uses this to her advantage handcuffing, nipple clamping and spanking both girls for being such bad sluts. She makes the two of them eat each others pussies for her amusement and instructs Penny to spray her lactating breasts into Vicki's mouth. Both girls are fucked with a strap ons. One in the pussy and one in the ass, proving to both be skilled prostitutes!

Penny Barber is bustling around the house preparing a cookie plate for her thick dicked step-son to get home for Christmas. Her husband is safely scheduled to return a day late, leaving her lots of time to get all her slutty holes filled and get her round ass punished for all her misdeeds this year with a strict belting and caning. Huge tits bouncing in her Christmas sweater she runs right into a holiday disaster: her step-son making out with his goth girlfriend he brought home for Christmas. Cookies come crashing to the floor as Penny regards her new rival Ivy LaBelle. A curvy perfect body to match Penny's with plenty of attitude, iconoclast Ivy is having none of Penny's holiday cheer, and drags her boyfriend upstairs to fuck her in tight bondage, flogging her wet cunt, and spanking her big round ass. Xander takes Ivy to task for thinking she's superior to his step-mother, but nothing prepares him for when Penny charges right up the stairs and calls him out of his bedroom in a clever bid to get some. He politely tries to stay out of trouble, but Penny get's right on his cock and tell's him she needs her punishment. Her handsy bullshit activates a sadistic flare in him, and he throws her over the couch, spanking the shit out of her, belting her ass, and giving her a strict caning. Putting her in tight belt bondage he plows her ass hard and fast, making her scream and cum like a whore in the living room. However, even that isn't enough for Penny. She waits like a cat for her prey in the living room all night, and eventually is rewarded when Ivy appears to steal some cookies from Santa's platter. She gives Ivy her Christmas present early: a big metal butt plug to prepare for her step-son's monster cock. Before she can get fucked, Ivy has to endure confessional, having hot wax dripped all over her tender flesh, flogged off, and made to hold her orgasms back while holding heavy buckets of coal. When Penny is sure this little goth slut is good enough for her step-son, she commences in training her how to take a huge dick in her tight ass, smothering her new step-daughter in her tits and cropping her swollen red cunt until she cums, shuddering and screaming in front of the Christmas Tree.

Marcelo (sissy name Marcy), in his pink satin dress, is locked to the floor with his legs spread and his balls tied taught to a post, leaving him fully exposed for Mistress Penny Barber to do as she wishes. She starts with some cock and ball torment but that only gets Marcelo harder. So, to teach his disobedient cock a lesson, Penny decides that sounding is the right medicine. Next, Marcelo is on his back, legs tied wide open so Penny can use the paddle he made especially for this meeting. Penny doesn’t limit herself to just paddling his ass, she gets in some good foot torment and caning for good measure and then stuffs her fist up Marcelo’s welcoming asshole. After some thorough exploring of Marcelo’s guts with her fist Penny moves on to a big black dildo to finish her happy little sub. Finally, Marcelo is lying face down in a neck-down body-bag where his naked Mistress paddles his ass before she eats it, then flips him over to give him the reward he’s eared by being such a good sissy all day.