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Up the Ass Stepsis

We've got a raunchy new Selects, so let's get nasty and jump into the mix! We love girls who love anal, and over the years, we've captured some truly magnificent up-the-ass scenes. The girls who take cock up the ass best of all are the horny stepsisters who want a piece of their stepbro's cock. This compilation showcases some of our favorite moments of the hottest stepsisters letting their brothers pound their backdoors. When having their mouth and pussy used isn't enough, or they have to find a loophole to retain their virginities, these girls have to take it up the butt. Of course, the guys are happy to make their stepsister's anal wishes come true. The babes in this compilation are true pros and take cock like it's nobody's business. If you're a fan of anal scenes, you've hit the jackpot. When you're done here, go back and watch the full scenes to get the stories in their entirety.

Bride-To-Be's Bachelorette Debauchery

Andie Anderson is getting married and her friends (including pervy Penelope Kay) are throwing her a bachelorette party she'll never forget! This involves surprising the bride-to-be with a stripper (Kyle Mason) who's DTF. After some hesitance, Andie decides to go wild on Kyle's cock... but will her fiancé coming home early lead to disaster or can the other party-goers keep him distracted?

PENELOPE WOODS Anal Fuck, Pussy Squirt

Sweet, dark-haired Penelope Woods teases in a bright green bikini with a choker and clear heels. The young, natural-bodied sex freak strips and spreads her holes, eagerly showing off her perky tits and freshly shaved slit. She crams a dildo up her ass while talking dirty to the camera, encouraging viewers to jack off. Hot anal masturbation warms her up for super-hung Vince Karter. The top stud spanks Penelope's plump rump while fucking her butthole. She takes a fuck ride with his big cock reaming her pussy. Penelope slobbers while giving a nasty, ass-to-mouth blowjob, loudly declaring, 'I can taste my asshole on that cock!' Intense, all-holes action delivers hard-choking fellatio, rectal gaping and dick/dildo double penetration! Vince fingers Penelope's pussy to a squirting orgasm! He blasts a hot load over her fluffy, pink lips. Following the creamy cum facial, Penelope spreads her worn out holes.

A Break From Dicks

Tiny has been trying to get back to the dating world after her divorce, but she's not quite there yet. All the guys she's seen so far are assholes, and her self-esteem is at its lowest point as she's not confident about her sex appeal. Her younger friend Penelope comes to visit her and tries to reassure her by complimenting her juicy tits. Secretly, she has been longing to taste her bestie's nipples for a while now, but Penelope has only been focusing on guys and hasn't really paid attention to her. However, after noticing the sexual desire in Penelope's eyes, she decides to make an exception: they can still be friends and fool around. Penelope jumps at the chance of fondling her milfy friend while Tiny finds the perfect excuse to taste her first wet pussy. A horny lesbian session unravels as Tiny and Penelope's mouths go wild all over each other's tight bodies, pressing her fingers deep inside each other's cunts, and using a handy strap-on dildo to enhance the sesh.

Penelope's Cookie Conundrum

Penelope needs to sell more cookies, but she doesn't know what she's missing that the other girls have. Jerry wants to show Penelope the art of the deal, so he teaches her a thing or two about how to sell cookies. Penelope gives Jerry a bit of her cookie in the mix, letting the lucky stud have his way with her. He gives her a creamy load to enjoy and use as inspiration for all of her future sales.

Double Trouble Anal Hime Marie And Penelope Woods

Penelope Woods and Hime Marie arrive at Jules' home, where they find him blindfolded sitting in a chair. Excitement builds as they realize what lies ahead. Jules takes control of the situation, guiding both women through their shared experience. They begin by taking turns sucking his cock, building towards the main event. Jules penetrates each woman in turn, first with anal sex, bringing them both immense pleasure. Their bodies become entwined as they reach their peak together. The girls Jerk Jules off until he cums. Penelope and Hime swap Jules' semen amongst themselves.

Latina neighbor Penelope Woods has a special welcome gift for her new neighbor

Penelope Woods notices she has a new neighbor so she stops by to drop off her special meatloaf as a welcoming gift. Penelope notices that her new neighbor is kind of attractive though and Penelope's husband hasn't given her dick in a while so she sure is horny. So Penelope makes her move and has her new neighbor take her to pound town. After all, what are neighbors for?

Perky neighbor Penelope Kay tests her neighbors cock before inviting him into her swinger parties

Sam is a bit annoyed that his neighbor, Penelope Kay, is always throwing parties. People leave empty bottles on his property and the noise is too much, but that is not the main point he is annoyed at. Sam has had a hunch that these shindigs going down are really swinger parties and he wants to be a part of it. His neighbor understands so Penelope has to test out his cock first and see how well he fucks before letting him in.

Birthday Threesome

Penelope just turned 18 and only wants one thing for her birthday: a chance with Skyler, her recently engaged friend. Desperate to get her, she fakes a whole birthday party and only invites her and Vince, her fiancé. When Vince leaves them alone, Penelope confesses to Skyler that she's had a crush on her for the longest time and kisses her. This leaves Skyler all confused and things turn awkward. Yet suddenly, she comes up with a solution: She will let Penelope eat her pussy if she agrees to let Skyler's fiancé fuck and cum inside of her. With nothing to lose, Penelope sits on Vince's cock in exchange for tasting her friend's sweet pussy.

Nothing Under the Gown

Will is taking graduation photos of his stepdaughter Camila and her best friend Penelope. At first, the photos are playful and innocent, but the girls have a little secret: they want to use the photo shoot to seduce the hot dilf. Will is no stranger to the girls' naughty charm and raises the bet by asking them to pull up their gowns for the pictures. When he discovers they are already nude under their robes, he knows the new graduates want a hot reward for their hard work. Before they go to college, it's Will's duty to show them how to party and handle dick.

The Irresistible Penelope

Tetsuya and Rambo get to go double on Penelope, filling her up and worshipping her pussy. The sweet babe treats the guys right and lets the studs kiss her body all over.

Banging Penelope Woods In Front Of Her Hubby!

So Penelope Woods was doing her weekly discipline to her cuck husband. As she does enjoy this, she decided to change it up a bit and have her friend Slim Poke come in and bang her out while her husband watches. She called Slim in and started sucking his cock and spitting the drool into her cuck husbands mouth. He was all about that. Then she had Slim bend her over and bang her out as her husband watched closely. Penelope had one orgasm after the other while riding Slims dick. Then when Penelope was getting railed on her back she asked Slim to bust a nut inside her so her cuck husband can clean it out. Her husband was all about it as Slim filled her up with his man goo.

Tastes Like Candy: Liv Revamped and Penelope Woods

Super-hot Penelope Woods makes her debut on Kink.com with this very sexy Everything Butt update. Partnered up with another hottie, Liv Revamped, things get hot fast, so fasten your seatbelts, turn on your fans, and be ready for some seriously sensual, steamy girl on girl anal action. Penelope and Liv are fed-up secretaries at a corporate company. To get back at their boss, these horny sluts sneak into his office and fuck each other on his desk. He?ll never know! Penelope has a little case filled with a variety of butt-toys. She pulls out a glass butt plug and gets started on Liv?s tight ass. She slides it in her tight hole to warm her up and then going from ass-to-mouth licks it clean. To return the favor, Liv tears open Penelope?s black stockings and licks her asshole to get her all lubed up and then stuffs the pretty pink butt-plug up her hungry ass and makes her cum good. Next, Liv wears a huge strap-on dildo. After throat fucking herself, Penelope climbs on top of Liv and rides her cock, first in her ass, and then her wet pussy, all the while dripping ass juice all over the boss?s desk. Then it?s Liv?s turn to cum, so in reverse cowgirl she slides onto that long cock and bounces her way to another hot anal orgasm. Things just keep getting juicier and more exciting as the day goes on. Liv slides a long slink inside Penelope?s butt and fucks her hole until she is quivering and cumming in total ecstasy. Next, these ass-loving ladies are ready for some even bigger toys. Gagged and bent over the desk with her ass up in the air, Liv gets her ass pegged with a thick metal g-spot dildo causing her to moan and gape. Penelope tastes Liv?s asshole and fucks her harder, making her cum again and then lets her lick all the cum off of the big toy. Liv wants more and feels adventurous, so she takes a huge pink and white dildo up her ass, stretching her hole wide that it gapes. Switching back and forth now Penelope is on her side looking super sexy with her torn nylons framing her curvy ass. She rubs her clit and Liv fucks her butt with the metal dildo until she trembles with pleasure from multiple orgasms. Their boss?s desk is a total mess all covered with cum and sweet ass juice. Fuck it!

Penelope Woods Gets Spit Roasted And Split Open In Her Very First DP

Penelope meets Jules and Zac at Jules' house. Jules and Zac begin by taking turns pleasuring Penelope orally and manually. The tension builds as they move closer to the main event - double penetration. Jules and Zac take turns entering Penelope from behind while she lies on her back. Their movements become more intense, each man trying to outdo the other in pleasure. In an explosion of passion, Jules and Zac both enter Penelope simultaneously, driving her over the edge with unparalleled intensity. She screams in ecstasy as they continue to bring her to new heights of pleasure.

Penelope Woods Cooks To Get Creampied

Good food is the way to a man's heart. Penelope Woods delightfully prepares a meal for Danny Mountain. The beautiful babysitter has long black hair and wears a light pink tank top with skimpy jean shorts. Finished cooking, Penelope serves the meal to the lucky stud with a sweet and inviting smile. Danny enjoys the food, so the naughty babe gives him another meal after kissing him passionately. Moving over to the living room, he continues to explore the slim sweetheart's body by licking her tits and shaved pussy. The sensual foreplay continues with fingering and blowjob-handjob combo before fucking in cowgirl. They pleasure each other with a 69 and fuck each other in reverse cowgirl, spoon, doggystyle, and missionary. Danny thrusts shallowly as he cums into Penelope's pussy.