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Gracie Green and Ryan Driller in My Sister's Hot Friend

L-O-S-E-R! That's the message Ryan's getting from his sister's cheerleader friend Gracie May Green. She's over at their house practicing her cheers and waiting for her friend, who gave her the message to deliver to Ryan. He was apparently a stud in high school, but things have changed for the worse for the jobless slob as time's gone on. But he does impress Gracie when he tells her that he dated her cheerleading idol back in his heyday, and he banged her after they were crowned prom king and queen. The story turns Gracie on so much that she's willing to give her friend's supposed loser brother a chance, and when she finds out his big dick still works well, she finds he isn't so bad after all! But he still needs a job.

Cherie DeVille and Ryan Driller in My Wife's Hot Friend

Ryan can't handle it anymore. Even since he's been introduced to his wife's work friend Cherie DeVille, he's wanted to fuck her brains out. And now that she's over for a dinner party, he has no choice but to confront her about it. He finds her alone upstairs and doesn't exactly tell her, but shows her with the big boner in his pants, how he feels about her. He's comforted to know that she has similar feelings for him, so they decide that the only way to solve the issue is to fuck! He's desired Cherie's nice big tits, fat ass and beautiful legs for the longest time…now is his chance to get what he wants!

Ashly Anderson and Ryan Driller in My Sister's Hot Friend

Ashly Anderson has been dying to ask her friend's brother Ryan to go with her to a sorority dance, and now that she finally has time alone with him, she musters up the courage! But the dickhead says no. His sister left to see her boyfriend, and all he can do to little Ashly Anderson, standing by the staircase, is deny her something she so dreamily desires. Well, fuck him. Those are the thoughts, both figuratively and literally, of Ashly. She follows him upstairs to his bedroom and tells him she still wants to hang out with him. Even when he requests she wear a particular pair of fishnet stockings to do so (who is this guy???). So she does. And she bends over. And Ryan rips open the stockings and…well, we'll let you see for yourself whether Ashly gets what she ultimately wanted!

Kimber Veils and Ryan Driller in My Dad's Hot Girlfriend

Welcome to the country! Kimber Veils just arrived at her boyfriend's 400+ acre farm while he's out of town, and she has no idea what the hell she's supposed to do. Her BF's son Ryan shows her the ranch where she's staying, and invites her to go to the “mart” for any of her shopping needs, and explains that the entertainment highlights tend to be riding horses and ATVs, then gathering with a group of six to hang out in the mart's glorious parking lot at night. Yee-haw! Destitute, Kimber finds solace in that the only thing she's going to ride for the next two weeks is Ryan's dick! The tattooed beauty gets naked for her boyfriend's son, then proceeds to give him a farmhand job he'll never forget!

Megan Sage and Ryan Driller in My Sister's Hot Friend

Megan Sage accidentally walks into the bathroom at her friend's house and sees her friend's brother Ryan naked, just as he's trying to hop in the shower. Awkward! But since her friend isn't there, Megan makes the most of the situation and decides she wants to fuck him! So, once he's out of the shower, Megan tries to make him feel better by walking into his room without any pants on. And, oh, does he feel better! In fact she moves his needle so much that it stands straight up! Megan takes that as a sign that it's the perfect time to suck and fuck her friend's brother's big dick and do away with any of the awkwardness!

Sarah Jessie and Ryan Driller in Neighbor Affair

Sarah Jessie's about to start a new life after her divorce: sell her stuff, sell her house, and move to Hawaii. That's why her neighbor Ryan is over looking at the grill she's trying to hawk. He's in the market for one, and she's a tattooed vegan with big tits, so they make the perfect yard-sale couple. What else is perfect is that Sarah's not married anymore, which means she's single, which means she's horny for cock, which means it's Ryan's lucky fucking day. And when she steps into the house for one minute and back out wearing lingerie, Ryan immediately stops poking around Sarah's grill outside, but moves inside — to the bedroom — where he can poke around her other grill with his dick. Suffice to say, Sarah gets the cock, Ryan gets the grill, but he doesn't get the girl because Sarah just wanted to get laid on the mainland before she gets lei'd in Hawaii.

Jane Doux and Ryan Driller in My Wife's Hot Friend

Ryan's so sick of his wife's college friends coming over and staying for days -- weeks -- on end. He's so sick of it in fact he tells his wife this over the phone, all the while one of those said college friends, Jane Doux, is already at the house, waiting for Ryan in the bedroom, in lingerie. He walks right into her trap and gets the first impression of her that she was hoping to give him. And once his hard dick meets her mouth and pussy, Ryan learns that his wife's college friends aren's so bad after all.

Daddy's New Wife

Ryan Driller comes home to meet his father but instead finds his new step mommy Cherie Deville in a bikini by the pool. Dirty Cherie shows her new step son that she doesn't marry for love (wink wink). Daddy's new wife is really slutty.

Bathing Beauty

Brooke Wylde is ready for her bath, complete with warm water, soap, and rose petals. She can't help but feel up her big natural boobs as she takes her bra off. Once her breasts are free, she gives in to the temptation to play with them by squeezing, shaping, and pinching her nipples. Slipping off her panties, she cups the heat of her shaved twat for a moment before stepping into the water.Now that they're all slicked up, Brooke can't stop stroking her huge bazongas. That's how Ryan Driller finds her. With such a sumptuous display before him, Ryan makes his presence known. Brooke is all smiles, leaning forward to whip out his cock. Kneeling in the water, she wraps her sweet mouth around his dick and starts sucking.Ryan enjoys the bathtub BJ, but he eventually leads her to the bedroom for a more comfortable romp. Once she's settled in, she pushes her big bosoms together and leans forward for a titty fuck. Then she scoots up Ryan's body enough that he can slide into her greedy fuck hole. Sinking down onto Ryan's fuck stick, she kicks off a fast and furious stiffie ride that leave her jiggling and bouncing in Ryan's face in a tantalizing way.Bending over, Brooke lifts her ass to open herself for Ryan's possession. He takes her from behind, working her in a doggy style pussy pounding that hits all the right spots. Brooke's gasps and moans fill the room, especially when Ryan leans forward to palm her heavy boobies as he keeps pumping his hips for both of their pleasure.Resuming her ride, this time with her back to Ryan, Brooke bumps and grinds to hit every delectable spot deep inside. This position enables her to reach forward to rub her tender clit as Ryan continues to fill his hands with her swinging breasts. Their mutual enjoyment is only increased when they fall to their sides so that Ryan can spoon Brooke from behind with deep slow strokes that finally bring her off with the deepest of joys.Still enraptured with her favorite toy, Brooke lays on her back and presses her jugs together for Ryan to fuck. That silken sheathe helps him reach the end of his endurance. With only a gasp of warning, he enjoys an explosive orgasm that covers Brooke's face and chest in a shower of love.

Seeing Double

BIgtit Blonde Brooke Wylde is all dressed up for her date with Alison Tyler and Ryan Driller. When Alison joins her at the window, a kiss on the back of her neck is all it takes to leave Brooke too horny to leave. She turns around in Alison's arms and pulls the brunette's dress down for a taste of her girlfriend's huge knockers, enticing Alison to return the favor.Soon both girls have peeled off their dresses and relocated to the couch wearing just their thongs and high heels. That's how Ryan finds them, and he's smart enough to mentally write off their date so that he can join in on the action. The girls work on getting him out of his clothes, dropping kisses and pressing their boobs to every inch of revealed skin.Rearranging herself so that she's seated on the back of the couch, Alison hums with excitement as Ryan leans forward to lap at her sweet juices while pressing two fingers deep into her tight twat. Brooke is eager to help double down on Alison's pleasure with deep kisses. When the trio switches it up so that Brooke is receiving the same attention that Alison just enjoyed, the blonde can't contain her joy.When it's Ryan's turn to enjoy some oral sex, he lays back and lets Brooke and Alison take turns doing all the work. They hold each other's hair while they deep throat Ryan's stiffie one at a time. Next, they each push their breasts together so that Ryan can titty fuck them in turn. Their double BJ keeps on going as they share his cock and balls, enjoying every moment of their musky delight.Dropping to her hands and knees, Brooke presents her bare pussy for Ryan to take however hard he wants. Alison is right there for Brooke's enjoyment, rubbing her jugs and offering deep kisses to muffle her cries of delight. Ryan doesn't falter for a moment as he pounds away at Brooke's creamy snatch, leaving her right on the verge of cumming.Making eye contact with Alison, Ryan knows just what his brunette coed wants without any words being exchanged. He curls up behind her, spooning her as he slides deep. His long sure strokes are just what Alison needs to fill the room with a chorus of monas as Brooke stands by to enhance her enjoyment any way she can.When it's Brooke's turn for another round of pussy pounding, she climbs on top of Ryan's hardon and slides down until she's fully impaled. Thrusting her hips, she works up and down while her bosom bounces in time with each movement. With Alison's helpful hand rubbing her clit, Brooke works her way to a body shaking climax.Climbing aboard Ryan's dick the moment Brooke is finished with her ride, Alison enjoys her own pussy pounding adventure. Although Brooke takes a moment to come down from her climactic high, she soon finds herself straddling Ryan's face so that he can feast on her slippery snatch as Alison continues working towards her enjoyable finish.When the girls are satisfied, they make sure to give Ryan the same level of enjoyment that they have just experienced. Pressing their boobs together, they work him with long strokes until he explodes all over both of them. Exchanging one last kiss, Alison and Brooke enjoy the last moments of their passionate threesome.

Sudsy Sexy Shower

Showertime is always fun for Jean Michaels, who takes keeping her big boobs clean very seriously. She soaps up her breasts several times, rubbing herself down with the suds while making the occasional foray further down to fondle her bare pussy. When she is finally satisfied that she's clean, she turns off the shower and prepares to get dirty all over again when she goes in search of Ryan Driller.When she finds Ryan sleeping in bed, Jean wakes him by pressing her breasts to his morning wood. Ryan wakes and is happy to help Jean remove his briefs so that Jean can wrap her puffy lips around his hardon. Her long sucks are interrupted only as she strokes Ryan off and then presses her breasts together for a titty fuck.Laying Jean on the bed, Ryan worships her knockers with deep kisses and teasing licks. His end goal is the sweetness of her bare twat. When he arrives, he flicks his tongue out in a teasing caress before settling in for a lengthy pussy feast.Swapping spots with Jean once again, Ryan finds himself on his back on the bed. He watches with anticipation as Jean swings a leg over his hips to straddle him and then sinks down onto his stiffie. Once she is fully impaled, she starts bouncing with long strokes that make her breasts bounce enticingly. Ryan soon gives in to the temptation to reach up and grab those jiggling globes for both of their added pleasure.Turning around, Jean moans with excitement as she bumps and grinds against Ryan's hardon in reverse cowgirl. He still can't keep from groping her big areola boobs, but Jean loves every moment of it. Even after Ryan anchors his hands to her hips to help her double down on her pleasure, Jean takes over squeezing those tender globes.As Jean takes a break by flopping onto the bed, Ryan ensures her continued pleasure by finger banging her eager fuck hole and then wrapping himself around her so that he can spoon her from behind. His hands continue to work Jean's tits as his hips thrust in and out of her dripping twat. He keeps up the long hard strokes until she is moaning her orgasmic bliss.Moments later, Ryan is forced to pull out of the warm tightness of Jean's sheathe. She turns onto her back, presenting her chest just in time. A heartbeat later, Ryan covers Jean with a jizz shower that is satisfying evidence of his love.

Getting Off The Typing Pool

Monique is fed up with Mr. Driller. He's been using her ideas to make their company millions, and she's not going to stand for it anymore. She decides it's about time to show Mr. Driller who the real boss is around here, starting by giving him a face full of her bountiful breasts. She ready to take her rightful place at the top of the firm, and it doesn't matter who she fucks or fucks over to get there. It's certainly one way to get out of the typing pool.

Avi Love and Ryan Driller in Diary of a Nanny

Nanny Avi Love knows how much her boss Ryan loves her for the work she does, not to mention her lithe body, over which he drools nearly every day. Avi's always daydreamed about fucking Ryan, but she's not sure how she'd feel about being with an older man. But when she witnesses her boss pass out drunk, then fantasize about fucking her, she makes up her mind!

Slut Hotel - Part 4

Ryan is finishing up his stay at the Slut Hotel with a nice four handed massage. He's nice and relaxed, but little does he know checking out of this place isn't that simple. He'll have to fuck his way out just like the other guy. With two insatiable babes like Anya and Ashley, he has his work cut out for him.

Big Boob Workout

Peta Jensen needs to keep her tight body in perfect shape, and she accomplishes that by working out. From jumping rope to lifting weights to doing pull ups, she won't stop until she's covered in sweat and satisfied that she's pushed herself to the max. As she is doing her cooldown yoga, Ryan Driller joins her in the gym and pulls her in for a kiss. That's the moment Peta knows that her workout is finished, and she is all smiles as she accepts the inevitability.Dipping his head down, Ryan drops sweet kisses on Peta's enhanced boobs through her bra. Disliking the way the material gets in the way, he frees them from their constraints so he can really go to town. From there he squeezes and sucks to his heart's content as he worships Peta's enhanced bosoms.Continuing his journey south on Peta's body, Ryan urges her out of her workout pants. When she settles down on a piece of gym equipment, he kneels between her spread thighs and goes in for a taste of her slippery bare pussy. She's nice and wet and totally horny from her workout, making it easy for Ryan to slide two fingers deep inside while working her clit with his magic tongue.Peta can't contain her lust for Ryan's cock, so she turns the tables on him after getting him out of his clothes. Opening her mouth, she takes the head of Ryan's dick in her mouth and then starts bobbing her head back and forth until she's deep throating him with every evidence of pleasure. When she backs off, she pushes her big boobs together and offers them up for a titty fuck.That just gets Ryan harder than ever and eager to fuck. Peta turns around so that he can slide into her greedy snatch from behind. As Ryan flexes his hips for both of their enjoyment, Peta fills the gym with her moans of excitement.Never one to be a passive partner, Peta urges Ryan to lay down on the bench she was just using. Once he's situated, she climbs on top of him and anchors herself with her feet on his thighs. She slowly positions herself so that her slick snatch hovers over the edge of his stiffie, and then sinks down until she's totally impaled. As soon as she's comfortable she kicks off a hard ride that gets her titties quivering and bouncing as she goes at it until she's moaning her ecstasy.As the couple seats themselves facing one another, Ryan once again drives into her. Their position facing each other makes for shallow strokes that hit Peta's g-spot while letting them maintain sensual eye contact. That's the perfect way for Peta to get off once again. Ryan can't last another moment as he feels Peta's pussy walls throbbing around him. Pulling out, he has just enough time to let Peta assume a position where he can cover her tits in cum and then he explodes in a satisfying climax that leaves his lover sticky and satisfied.