Latest updates featuring Oliver Flynn

Sonna loves decorating the house for the festivities. There's just something magical about good ornamentation for the holidays, and that makes the petite vixen both jolly and horny. Dressed as a snow angel and setting everything up for the occasion, she receives the visit of her good friend Oliver, who will give her the extra she needs to enjoy the season to the fullest!

Is your house filthy? Then, my friend, you're in luck! Macy, the cutest (and sassiest) little maid you've ever seen is here to clean it up! The petite babe loves to play around as she does her work, and she doesn't mind going the extra mile to leave everything spotless, even if it means stripping off her clothes to do it. Once her job is done, she takes time to relax and play with Oliver's big cock.

Khloe and Laya are so excited (and a little bit horny) about the party they are going to tonight with their boyfriends. The two twin-like step-siblings are almost ready to go when Khloe receives a call from her boyfriend telling her he is not coming. Laya can't stand seeing her stepsis down, so she asks her man Oliver to make her feel better somehow. The couple decides to include Khloe in an intense threesome that helps her forget about her ex.

What's up, Mylf lovers? It's time for another Mylf of the Month celebration, and if you've been keeping up with our miniseries, Momster-in-Law, then you'll be elated to know Ryan Keely is May's Mylf of the Month. Ryan is the world's best stepmom and has nothing but love (and maybe a little lust) for all her studly stepsons. This busty legend shows off what she does best in this MotM update. With the help of Oliver, Ryan goes all out and wastes no time getting down and dirty. She's got a body that will knock your socks off and a fierce sexual appetite. So help us show Ryan some love as we honor all her hard work!

Momster-in-Law (Part 3 of 3): The wedding day is finally here, and tensions are at an all-time high between the bride, Serena, and Ryan, her awful stepmother-in-law. Minutes away from walking down the aisle, Serena is horrified to find Ryan wearing a white dress just like hers. Serena freaks out and confronts an adamant Ryan, starting a tremendous fight. Serena finally decides to call the wedding off and tell Oliver, the groom, that she can't accept his stepmom. Suddenly, Ryan comes in and apologizes to Serena. The two patch things up and the ceremony is back on, setting the mood for a very hot wedding night between husband and wife…and stepmom-in-law!

Momster-in-Law (Part 2 of 3): After Serena's boyfriend Oliver proposed, the fairy tale feelings seem to fade away as Ryan, Oliver's manipulative stepmother, continues to give Serena a hard time. By pretending to feel under the weather, Ryan keeps bossing Serena around, to the point of asking her to join her in bed. Serena does her best not to break, doing everything her soon-to-be stepmother-in-law requests. Suddenly, Ryan comes up with her most devilish idea yet: testing her future daughter-in-law's abilities to please her stepson.

This Team Skeet Classics update features Natalie Porkman and Oliver Flynn. Originally released on Nov 7th, 2019, this Family Strokes scene was and still is a major hit! Natalie is studying to be a nurse, so when her stepbrother Oliver gets injured she's in charge of taking care of him. Natalie quickly notices that Oliver is often jerking off under the covers and when she's faced with his huge boner she figures she could take care of it as well!

Family is the most important thing in the world, so when Ryan learns her stepson, Oliver, is getting married, she does everything in her power to drive his fiance, Serena, away. Ryan needs to know she isn't replaceable, so like a good stepson, Oliver fucks her hard to show her he still cares. Later, Ryan puts Serena to the test to make sure she's good enough for her sweet Oliver. Serena is a champ and takes on every intense sexual act Ryan throws at her. But the fun doesn't end there. On the big day, Ryan, Serena, and Oliver officiate their eternal bond as husband, wife, and stepmom. Serena and Ryan ride Oliver's hard cock and take turns pleasing him, all while making sure they keep each other satisfied, too - it looks like family really is the most important thing in the world.

Kay Lovely is about to show us her rigorous workout routine with TeamSkeet. She begins by stretching and putting effort into a deep span of her legs; then, she demonstrates just how low she can go with her squats. She suddenly stops because of her sweaty tits, but we've been great students, so Kay has a treat for us; she brings out her moist boobs and begins showing off how much they can bounce on the exercise ball, which has her craving a hard dick. Luckily, Oliver gets here just in time, and when Kay notices just how ready he is, it's time for the best part of this Lovely exercise routine.

Originally released in May of 2019, this Team Skeet Classic features bombshell Paige Owens and Oliver Flynn. This scene does so well because it combines excellent fantasy and comedy, and the actors shine here. As a longtime fan favorite, we're happy to have selected this scene for our Team Skeet Classic series. Paige Owens is always teasing her watchful stepbrother, Oliver Flynn. When her stepdad goes away for the afternoon, Paige finally catches Oliver alone and takes full advantage of the opportunity.

When petite stepsister Dixie Lynn catches her stepbrother Oliver Flynn playing with himself all the time, she challenges him to do 'no nut november', so for the whole month he's not allowed to touch himself, and Dixie is confident he won't be able to resist. But turns out that Oliver wins, so Dixie delivers her beloved prize as promised.

Fishnet stockings, big juicy tits, and an extra tight bod – ebony babe Jordy Love has it all. Add the fact that her favorite workout is pole dancing, and it's obvious why she's so in demand.

Curly-haired Ella Cruz can be a real brat when she doesn't get her way. Today, her boyfriend has to leave on a big business trip, and she doesn't want to let him go. Luckily, the super petite Latina fits inside his luggage, so she sneaks inside and goes along for the ride. But when her laser-focused boyfriend discovers that Ella's a stowaway, he's livid. To make it up to him, Ella grabs onto his shaft and shoves his cock down her throat while she's still in his luggage. To make it even sweeter, she bounces on his dick and takes a hot cum facial.

Pierced nipples, a thin waist, and long blonde hair, teen cutie Aubrey Thomas has all it takes to make your dreams come true. She loves bouncing her ass in a see-through white leotard, and her twerking abilities are top notch. She even makes a wish before smashing a birthday cake with her fat ass! Lucky for her, the wish comes true as our stud presents his huge cock for her to twerk on. She pops her pussy for him and her ass jiggles as he works her cunt from behind. He slams her passionately and then drops a gooey load of cum on her booty. Let them eat cake...

A small babe like Skylar Valentine loves a big dick inside her petite pussy, and sometimes she likes to add a little spice to the fun. Today, she wears a lusty black cat mask as she sucks and fucks a huge cock. The sexy bleach blonde stuffs her cunt with a big dildo and then gives our stud a drooling blowjob. Then, she pops her pussy on the couch as he strokes inside her aggressively. Skylar closes her eyes and feels waves of pleasure wash over her nubile body. She cums multiple times and then enjoys a milky helping of cum. Skylar is one sexy pussy!

Teeny tiny Alicia Williams is all kinds of excited when her brothers best friend pulls in the driveway. She has been dreaming of getting her pussy plowed by his cock for weeks, and she is ready to put her charm to work. She shows him some sultry pics of her cute tits, and pretty soon the guy is rock hard. He tries to keep it together, but he just cannot resist her pretty face and slim waist. She grabs onto his dick with both hands and sucks sensuously. Then, he pleases Alicias twat, pulverizing her with his boner before shooting cum on her cute face! This blonde temptress is all about her getting her nut.

Teeny tiny Athena May has an undeniable sweet tooth, so when she sees our stud munching on some candy, she needs a fix. But when he catches the brace face eating sweets, he is pissed. The only way he will keep it a secret from her parents is if she sucks on his lollipop. She agrees, and he shoves his long cock between her lips. Athena gags as she makes stunning eye contact with her pristine blue eyes. Then, the beautiful babe enjoys a deep pussy pounding and gets a splash of cum on her chin! Do you think Athena is a bad girl? Let us know in the comments!

Tatted up cowgirl Gina Valentina is ready to take on the world with her riding abilities. She wants to show off just how well she can keep a cock up and work her hips into a friction frenzy. Today, she gets her chance, riding our studs prick as she moans in pleasure. The gorgeous brunette shows off her bubble butt and her petite physique as she plays with his prick, letting it slide down her hungry throat. Then, she launches into the rodeo ride of her life, taking a big shlong deep inside her velvet holster. This cowgirl definitely knows how to wrangle a dick!

Super thicc ebony chick Adriana Maya redefines the term brown sugar when she shows up in a skimpy outfit and high black stilettos. The girl is an absolute STALLION in the best sense of the word, and she knows how to rock her hips and make her body talk. She peels her underwear off and oils up her fat ass in preparation for our stud to present his big prick. He whips it out and she gobbles it down before spreading her legs wide open. The lucky guy penetrates her delicious cunt and plows her hard before serving up a dripping facial. Adriana is one of a kind!

There is nothing like a beautiful set of natural titties to start the new year off right, and Michele James is definitely giving us our fix in 2020! She lets her knockers bounce and jiggle in lacy red lingerie that nearly melts off her scalding hot body. By the time she finally gives us a full peek at her perfect titties, our stud shows up ready to work her over by the pool. Micheles pierced nipples get rock hard as he caresses her cans and knocks her cooch from behind with his thick cock. Then, he titty fucks her until she sticks her tongue out to enjoy a splashy cum facial that leaves her one hundred percent satisfied. Michele is an uncut gem!

Tiny hottie Spencer Bradley is excited for her first day on the job as a babysitter. She really wants to earn some money, so much so that she is willing to steal to do it! She looks around the house while her new boss is out and finds his secret stash of loose change. But when he discovers she is a thief, he punishes her with his massive cock. She gets down on her knees and begs for forgiveness before opening her mouth and taking his long dong down her throat. Then, he plows her while she sits in a baby carriage. The fun ends with him covering her pretty face in his dripping nut. Spencer will not be stealing again anytime soon.

Studious Natalie Porkman is trying to get some serious studying in today when her hung study partner shows up late yet again. Nevertheless, she keeps her eyes on the prize, hitting the books with dedication. But the distracting guy keeps looking up her skirt while she tries to memorize information! To get the dirty dudes mind off sex, Natalie pops her pussy while she works on the school project. He slips his prick inside her love tunnel, pounding her from behind, making her moan and squirm in pleasure. Then, he gives her a gooey cum facial to cap off the study session. These two are sure to get an A!

Lady of the house Crystal Rush is willing to do anything for her new foster kids. The young siblings are looking for her love, affection, and a little extra nourishment. In fact, Crystals foster stepdaughter, Carmen Rae, is absolutely thirsty for Crystals tits! She wants to suck and nibble on her pretty nipples. At first, Crystal is appalled. But after a little consideration, she realizes she needs to the roll of foster stepmom to its utmost. Her new foster kids lick her titties and then ravish her sexually. Her foster stepson sticks his huge, long dick inside her MILF cunt and then takes a turn plowing out his sisters pussy too! What a way to start a foster family.

Super cute princesses Ella Cruz and Lola Leda never miss a chance to get into a heated threesome situation with each other, and today is no exception. When our stud shows up, the girls know exactly what they want. They tell their boyfriends that they are going to be busy for the next hour and a half. Little do the poor guys know, they are busy fucking another guy! They surround him and pull his pants down, gobbling up his big dick like they have been waiting forever to taste him. Then, they bust out their perky titties and get into some serious penetration action. The hung guy fucks them one at a time as they moan in wild pleasure. Looks like these girls have some explaining to do with their BFs!

Ebony babe Kosame Dash is what we like to call a unicorn. Not only does the hottie have an incredibly sexy body, but she also has one of the most seductively gorgeous faces we have ever seen. When this thicc princess bends over and spreads her legs, it is like watching heavens gates open up. Lucky for us, Kosame loves getting a fuck session in right after a hard work out! Today, she lavishes our lucky stud in sexual attention. He taps it from the back, sliding his dong in and out of her juicy pussy. Then, she goes for a wild cock ride that ends in a splash of cum on her pretty face. Kosame is a star!

Petite princess Ella Cruz is a little bit of a goody two shoes when it comes to school. Her boyfriend is always helping her out with her homework and chores, but when Ella keeps giving him blue balls, he gets totally fed up! Finally, Ella plays a game of hide and fuck with her man, getting butt naked on her bed for the lucky guy to find her. When he sees her sexy body, he dives right into her tight pussy. She chokes on his thick rod and arches her back as he inserts his prick into her tiny cunt. Then, she takes a splash of cum all over her cute face. When Ella puts out, she goes all the way!

Nerdy Kali Roses has been really hitting the books recently. But all this studying comes at the expense of her relationship with her horny boyfriend. The guy is supportive, but how long can he take looking at this banging blonde teen without sticking his cock in her tight, young pussy? Finally, he thinks of a solution. He uses an age old technique to get Kali to obey whatever commands he delivers. When she is in a receptive state, he demands that she opens her mouth wide to give him a deepthroat blowjob. She does, slobbering all over his cock and getting it drenched for penetration. Then, he slams her bookish twat before filling it up with a hot creampie. That should hold him over for a while!

Sweet Sofi Ryan has a bubbly personality, and she just loves working out. Today, she shows off her round ass while she gets ready to put in some serious reps. She jumps some rope, letting her perky tits bounce out of her top as she works. She likes getting sweaty and feeling her skin glisten in the sunshine. When she finally pulls her workout pants down around her ankles, our stud shows up to give her another round of cardio. She busts her tight young pussy open and sits on his huge dick, pushing back on it as she goes for a crazy ride. She screams out as she cums, letting the orgasmic pleasure rush through her whole body. Do you think Sofi is super cute? Let us know in the comments!

Sweet blondie Kali Rose is so excited that she has someone coming over to help her learn how to paint. But this girl is ambitious. She immediately wants to get into some of the finer parts of the art, including nude modeling. She gets her teacher to strip down, and when he shows her his huge cock, she is super turned on. She yanks down her overalls and exposes her cute young ass. Then, he shoves his long dick inside her wet cooch, fucking her from behind as her face contorts in pleasure. Kali cannot believe how deep his dick is going as her eyes roll back orgasmically. Finally, she gets her face painted by some sticky cum, and Kali is satisfied.

Honey Moon has been devastated ever since her boyfriend broke up with her for cheating on him. But they say the best way to get over a guy is to get under one, and that is exactly what Honey has on her mind. She gets on a dating app and matches with our lucky stud, inviting him to come over right away. When he gets there, he sees how hot this sexy little Asian chick is and then reveals that he is actually a high school student. Honey does not let his age get in the way. She whips his tree trunk dick out of his pants and jerks him until she is ready to get penetrated. Then he slams her tight Asian pussy until she is cumming harder than she ever did with her boyfriend. Seems like a match made in heaven!