Free Spanking and BDSM Videos and Galleries with Ivy Sherwood. We have previews with Ivy Sherwood from Assume The Position Studios and Worst Behavior Productions.
Are You Going To Be A Good Girl? Ivy Sherwood Punished Hard And BareIvy is bent over the arm of the couch, topless, her panty covered bottom pushed high in the air for discipline. The slap of leather on the thin cotton of her panties, searing pain right through. Are you going to be a good girl, is answered with a resounding 'Yes, Sir' Her pretty cheeks wobble and jiggle under a long and forceful strapping. Her full bottom panties are peeled down to her thighs, leaving her bare bottomed for a heavy strapping. Ivy bravely takes her licks, relieved when he finally announced her final swats. The big wood paddle cracks down firmly on her peachy round globes. Her bottom is swollen and bruised as she whimpers and cries for her final paddle swatsRemove Your Top And Bend Over The Couch - Ivy SherwoodIvy is instructed to remove her bra, bending back over the arm of the couch with her bare breasts swinging freely. The impact of the strap makes her pretty tits jiggle with each impact. A heavier strap is used to get the message across as Ivy begins to gasp and whimper in pain. Her pretty face betrays her, as the punishment begins to have its intended effect. A large wood paddle makes a satisfying crack across her jean clad bottom as the lesson is driven home.Meet Me In The Living Room - Ivy Sherwood DisciplinedIvy is instructed to meet her boyfriend in the living room for discipline, Her ass looks incredible in tight white jeans, bent over the arm of the couch. The RAZOR STROP slaps down across the tight denim, Ivy takes the opening licks bravely. A thicker domestic straps echoes with each intense lick, Ivy begins to jump a bit. A round paddle swats crisply from cheek to cheek, raising the heat through her jeans, Ivy begins to whimper.Ivy Sherwood Nude Belt Whipping And PaddlingAfter Ivy is rewarded with a much needed orgasm, she is stripped naked for inspection over the bed. The big strap lands with force, jiggling her pretty round cheeks as she fights to take her discipline, A final volley of her favorite belt lays fresh welts across her poor bottom. A big school paddle delivers a final dose of discipline, Flattening crack of the paddle, jiggling as she gasps through 10 final swats. She is all too eager to drop to her knees to show her appreciation for her spanking.Shared Boyfriend- Shared Belt - Part 2Ivy's boyfriend comes home to find two spanked girls snuggling naked on the bed. Confessions all around until it is decided that since they are already sharing him, he will spank them together. Stevie and Ivy line up side by side on hand and knees for a good hard belt whipping. Seeing these two naked girls getting their backsides tanned with the belt is something special to behold. Turning up the heat with a BIG paddle, hard swats echo off the walls of the room as both girls gasp and cry under his stern attentions. Turned on by his relentless heavy hand, they discuss what they will share for the rest of the evening with sore bottoms.My Roommate Is A Secret Stripper - Part 3Stevie discovers her roommate Ivy has been lying to her, concerned about her late night activities. After weeks of suspicious behavior, Stevie confronts her with skimpy lingerie found in the laundry. Ivy confesses that she took a job stripping and has been lying about where she goes at night. Sorry for making Stevie worried and all the deception, Ivy vows to make things right by submitting to a spanking. Stevie enjoys this predicament, stripping her naked for punishment in a variety of humiliating positions Turned on by the naked beauty, Stevie can't help but to punish Ivy's pretty pussy, eventually rewarding her with a series of powerful orgasms. Ivy cums over and over, squirting all over, throbbing and satisfied. As she gets up to leave the room, she notices a very specific pair of boxers on the floor…My Roommate Is A Secret Stripper - Part 2Stevie discovers her roommate Ivy has been lying to her, concerned about her late night activities. After weeks of suspicious behavior, Stevie confronts her with skimpy lingerie found in the laundry. Ivy confesses that she took a job stripping and has been lying about where she goes at night. Sorry for making Stevie worried and all the deception, Ivy vows to make things right by submitting to a spanking. Stevie enjoys this predicament, stripping her naked for punishment in a variety of humiliating positions Turned on by the naked beauty, Stevie can't help but to punish Ivy's pretty pussy, eventually rewarding her with a series of powerful orgasms. Ivy cums over and over, squirting all over, throbbing and satisfied. As she gets up to leave the room, she notices a very specific pair of boxers on the floor…Shared Boyfriend- Shared Belt - Part 1Ivy's boyfriend comes home to find two spanked girls snuggling naked on the bed. Confessions all around until it is decided that since they are already sharing him, he will spank them together. Stevie and Ivy line up side by side on hand and knees for a good hard belt whipping. Seeing these two naked girls getting their backsides tanned with the belt is something special to behold. Turning up the heat with a BIG paddle, hard swats echo off the walls of the room as both girls gasp and cry under his stern attentions. Turned on by his relentless heavy hand, they discuss what they will share for the rest of the evening with sore bottoms.A Summer Internship - Ivy Sherwood Sore Bottom College Credit - Part 2Ivy has a job at a small office for a summer internship while she is home from college. Her new boss is a friend of the family and she is looking forward to an easy summer of slacking off surfing the internet for college credit. At her desk, she neglect the work she has been assigned and begins to look at her favorite porn. Oblivious when her boss enters the room, horrified to find her looking at pornography. Scolding her and threatening to tell her parents, Ivy is all to eager to work out alternate arrangements. Standing up to bend over her workstation, skin tight skirt pulled taut as her punishment begins with the yardstick. The thin wood stings up and down her bottom and thighs. Picking up a heavy leather strap and paddle to drive the lesson home. The Boss pulls up her skirt to apply correction to her exposed bubble butt, scolding as he punishes. Lecturing her about modesty, she is instructed to pull her breasts out of her top, now fully exposed under his eye for the remainder of her ordeal. After another round of the yardstick, strap, and paddle, she is sore and contrite. Sitting back down on a sore bottom, she worries that this won't be the last spanking she will suffer this summer.Boxers On The Floor - Roommates Spanking Revenge - Part 2Before Ivy leaves the room, she sees her boyfriends boxers on the floor, demanding to know 'Are you fucking my boyfriend?' Stevie admits to pleasuring her boyfriend when the attraction became too much to ignore. 'Well he does stop by sometimes when you're not here… Ivy decides to take her revenge on Stevie's bottom. Stripping her naked Hard bare bottom spanking with followed by an Orgasm.Boxers On The Floor - Roommates Spanking Revenge - Part 1Before Ivy leaves the room, she sees her boyfriends boxers on the floor, demanding to know 'Are you fucking my boyfriend?' Stevie admits to pleasuring her boyfriend when the attraction became too much to ignore. 'Well he does stop by sometimes when you're not here… Ivy decides to take her revenge on Stevie's bottom. Stripping her naked Hard bare bottom spanking with followed by an Orgasm.A Summer Internship - Ivy Sherwood Sore Bottom College Credit - Part 1Ivy has a job at a small office for a summer internship while she is home from college. Her new boss is a friend of the family and she is looking forward to an easy summer of slacking off surfing the internet for college credit. At her desk, she neglect the work she has been assigned and begins to look at her favorite porn. Oblivious when her boss enters the room, horrified to find her looking at pornography. Scolding her and threatening to tell her parents, Ivy is all to eager to work out alternate arrangements. Standing up to bend over her workstation, skin tight skirt pulled taut as her punishment begins with the yardstick. The thin wood stings up and down her bottom and thighs. Picking up a heavy leather strap and paddle to drive the lesson home. The Boss pulls up her skirt to apply correction to her exposed bubble butt, scolding as he punishes. Lecturing her about modesty, she is instructed to pull her breasts out of her top, now fully exposed under his eye for the remainder of her ordeal. After another round of the yardstick, strap, and paddle, she is sore and contrite. Sitting back down on a sore bottom, she worries that this won't be the last spanking she will suffer this summer.My Roommate Is A Secret Stripper - Part 1Stevie discovers her roommate Ivy has been lying to her, concerned about her late night activities. After weeks of suspicious behavior, Stevie confronts her with skimpy lingerie found in the laundry. Ivy confesses that she took a job stripping and has been lying about where she goes at night. Sorry for making Stevie worried and all the deception, Ivy vows to make things right by submitting to a spanking. Stevie enjoys this predicament, stripping her naked for punishment in a variety of humiliating positions Turned on by the naked beauty, Stevie can't help but to punish Ivy's pretty pussy, eventually rewarding her with a series of powerful orgasms. Ivy cums over and over, squirting all over, throbbing and satisfied. As she gets up to leave the room, she notices a very specific pair of boxers on the floor…You Might Be Due For A Little Reward - OTK Orgasm For IvyIvy takes her spanking like a good girl, knowing that rewards will come as he teases and spanks her needy pussy. Oiled cheeks bouncing under his hand, as he applies the vibrator between her legs. Ivy moans and gasps, quivering as she tries to hold off her orgasm. Quickly she is overcome, letting the orgasm take over. His hands return to her bouncing bottom, spanking and caressing her incredible cheeks as she basks in the afterglow.Oiled Bubble Butt Spanking IvyIvy strips out of her skin tight catsuit, leaving her in nothing but a skimpy thong. Her pretty bubble butt is bent back over the bed for another dose of the strap. Her cheeks are beginning to swell, pausing to massage oil into her pretty round globes. She crawls back across, straddling his knee for him to rub the oil into her punished skin. The prettiest jiggle as his hand begins to spank again, not neglecting her pussy.Blistered OTK - Home For The Summer - Part 3Naughty girls get paddled on their bare bottoms, hooking the waistband of her thong panties they are pulled down to center thigh. The heavy paddle splats across her bruised cheeks as she promises to get her grades up and behave. Step daddy picks up the most painful paddle drilled with blistering holes. In between excruciating swats his hand inspects her progress. Ivy obediently takes her punishment, gasping and fighting back tears. She counts 10 final Swats as she holdbacks tears. Her bottom is bruised and blistered, a reminder to stay focused and behave like a proper young lady.A Proper Young Lady - Home For The Summer 2 - Pink Thong Panties Spanked And Paddled OtkIt is no mystery why pretty little Ivy receives so much distracting male attention at school. With her shorts pulled down her perky little butt is revealed. Impossibly bubbly cheeks framed in a bright pink thong. Step daddy's big hand has her cheeks bouncing as the heat rises from her punished skin. Smack, flatten, jiggle, Ivy whimpers has his hand echoes off her bottom. Despite her promises to behave he picks up the paddle and delivers painful swats to her exposed cheeks.Good Girls Get To Cum- Nude Spread Spank And Hitachi - Ivy SherwoodMoving on to the bed, Ivy knows her reward is near. Straddling his lap, she gives him full access to her delectable ass and pussy. Oiled, glistening cheeks bouncing under his big hands, she relishes the heat building between her legs. Massaging her mounds, his fingers pet and caress her cunt. Unsnapping the crotch of her bodysuit, he applies the hitachi to her needy princess parts. Continuing to slap her oiled cheeks, Ivy grinds into his lap, begging for permission to cum. Exploding over his lap as he caressed her punished flesh, Ivy collapses. Eager to return the favor she climbs off his lap, crawling up to unzip his jeans with mischief in her eyes.Ivy Sherwood Belt Whipped Beauty - Warm Bottom Welcome HomeShe craves and fears the belt, her pussy quivers as she hear the leather slides through his belt loops. Her skin tight jeans are pulled taut across her peachy mounds, making a perfect target. Ivy braces herself, gasping at the sting, pushing back for more. His hand caresses her hot bottom, lingering between her legs, knowing exactly why she is there. Counting off 20 hard licks, Ivy can barely wait for his to take her jeans off. Her bubble butt spread across his knee, he soothes her swollen cheeks with oil, continuing her spanking.Ivy Sherwood Summer Break Spanking - Home From CollegeIvy is home from school for summer break. Her report card reveals that she is on academic probation, distracted by all the boys on campus. Defiant during her scolding, she will soon change her tune over step daddy's lap. His hand slaps down on the seat of her shorts before picking up a paddle. Her pretty face grimaces in pain as the burn of the paddle penetrates her round little bottom. Her cheeks burning from the paddle, terrified has his fingers hook the waistband of her shorts to pull them down.Ivy Earns Her Cum - Strapped And Spanked To Orgasm - Ivy SherwoodHorny little Ivy does her best to earn rewards over his lap. Spanked and working into a frenzy, she is instructed to hand him the hitachi. The powerful head placed on her pussy as she begs for release. Laying across a pillow with her bottom thrust in the air, the vibrator is positioned between her legs. Grinding on the head, the heavy strap slaps down, postponing her pleasure. Pulling her tits out, the strapping continues, her pretty bottom grinding into the vibe as she is beaten. Her cries of ecstasy fill the room along with the crack of leather. She begs for permission to cum. Writhing, grinding, crying with pleasure as her well earned orgasm pulses through her.Home For The Holidays - Bubble Butt Paddled In JeansWhen Ivy comes into town for the end of the year, she has more than family visits on her mind. She craves his special touch, the way he puts her across his knee and smacks her bottom. Nervously she sends the text, setting up their meeting, and a sore bottom. He loves her curves in skin tight jeans, leading her to the bedroom, positioning her firmly across he knee. Caressing her succulent cheeks, pitter patter of soft slaps, building rhythm. She moans under his adoring attentions, relishing at the building heat. His big hands cover each cheeks, alternating slaps as they juggle and bounce. She can feel the warmth between her legs, the vibrations of his spanking having their intended effect. How long until he pulls down her pants and panties and discovers her wetness?Pajamas Down - Paddled And Pleasures - Ivy SherwoodPicking up a thick wood paddle, Ivy gasps at the first impact. Ragged breathing as she tries to absorb the punishing swats, whimpering over his lap. After a good paddling, her pajama pants are pulled down to inspect her hot flesh. Some hand spanking, his hand trails to pet her pussy, working her into a frenzy. As she nears climax, he removes his attention, continuing her spanking on exposed hot flesh. Teasing, tantalizing, punishing, Ivy melts into a puddle under his touch. Will he let her cum??Pajama Spanking OTK - Ivy SherwoodDressed for bed, Ivy won't be happy until her bottom is dealt with and a handful or orgasm to send her to blissful sleep. Her magnificent mounds stretch the thin fabric , barely protecting her tender flesh. Bouncing under his hand, she moans with need as his hand trails to the warmth between her legs. Alternating his hand with a paddle intensifies the sting through her thin pajamas painful, yet undeniably turned on.Nude Wheelbarrow Spanks And Thanks - Ivy SherwoodThe paddle collides with her oiled cheeks, moaning, turned on, ass on fire. Her thong bikini is pulled down, leaving her completely nude and exposed over his lap. Rhythmic spanking on her cunt, she spreads her legs, his fingers pushing her over the edge. Ordered off his lap, she is re-positioned face down, straddling his lap in wheelbarrow position. A delectable position to swat her juicy cheeks and tease her pretty bare pussy. She promises to be a good girl, crawling to her knees to unbuckle his belt.Ivy Sherwood Pleasure Swats Erotic SpankingIvy's cheeks are swollen and red from spanking as she pushes up to meet his hand. Slathered in oil, his hands caress, petting her pussy in between swats. She moans, crying out as he pushes her to an explosive orgasm. This is just the kind of spanking she likes. Untying her bikini top, her hand reaching between his legs. On her hands and knees, she is spanked and paddled on her oiled bottom, as she urges him on with her hand on his cock.Oiled OTK Spanking - Ivy Put In Her PlaceReturning from the pool in a thong bikini, Ivy pulled across his lap for some immediate correction. A lesson in modesty under his heavy, she does her best to distract and seduce her boyfriend. She knows her epic bottom will distract him, spreading her legs to encourage his hands. Slathering her skin in coconut oil, soothing before intensity of an oiled spanking.Cum Whipping For Ivy - Punishment Ritual - 4After a lengthy erotic flogging on her most sensitive princess parts, Ivy is once again turned over to present her ass for discipline. She is overjoyed to be handed the Hitachi to pleasure herself as she is whipped. The lash of the whip falls rhythmically as she luxuriates in the buzzing between her legs. Her ass and thigh jiggle under the heavy whip, begging to cum. Finally given permission, she collapsed in ecstasy. She crawls to the edge of the bed, frantically unfastening his pants to collect her reward in her eager mouth.Tits And Cunt Flogged - Ivy Punishment Ritual 3A big school paddle explodes across Ivy's poor little bottom. A moan, a gasp, swat, finally she is uncured from the bench and ordered to lay on her back. The flogger trails drop from her full breasts to her exposed cunt. Moaning as the leather bites into her princess parts. The larger flogger is used to caress and punish her thighs. Ivy enjoys the attention to her most sensitive bits, her beautiful face betraying her arousal as she is intimately punished.First Taste Of The Lash - Ivy Flogged And Whipped - Punishment Ritual 2Stripped nude and spread over the punishment bench, Ivy will have plenty of time to consider her behavior of the past week. The heavy oiled cowhide flogger splat across her ass and thighs. Moaning as she fights to absorb the pain, the heavy leather falls stinging and burning without a break. A few well placed strokes punish her cunt as she gasps. The single tail whip sizzles through the air, exploding with a crack. The whip sears into her skin, the burn tests the edges of her tolerance. The lashes fall hard and steady, burning angry red welts with each crack.A Date With Discipline - Friday Nighty Punishment Ritual - Ivy SherwoodFriday nights are a standing date for Ivy to be disciplined for the naughtiness of the week. Reporting to the bedroom, she drops her robe, climbing naked across the punishment bench. The giant leather strap collides with her pretty bare bottom sending ripples through her exposed flesh. A heavy leather paddle flattens her cheeks, Ivy gasps at each application. His hands sooth and tantalize as she is punished, preparing her for more to come.Ivy Sherwood Belt Whipping CumAfter a dose of the hairbrush on her throbbing backside, Ivy is bent over the edge of the bed. His belt slides through the loops as she waits anticipation the warmth of the leather across her deserving bottom. The familiar hum of the vibrator is positioned between her legs. His hands squeeze her succulent tits as she moans on the vibe. The belt begins to crack across her jiggling bottom as she works towards an explosive orgasm. Begging to cum, the belt falls hard and furious as she is finally given permission. Sh eagerly falls to her knees to say thank you.Ivy Sherwood - OTK Spank And PetEagerly, Ivy spreads her incredible round bottom across his knee. His hands caress and tease her needy cunt, petting and spanking. Her perfect bubble butt bounces as she moans her approval. The imprint of his hand blazes glows in the center of each cheek, framed by her thong and thigh high socks as he continues to spank and tease.Home Early From Work, Ivy Sherwood POVIvy seductively rolls around the bed in panties and her favorite naughty crop top. Petting herself, her panties are pulled aside, lost in ecstasy she barely hears the door open. Home early from work, exactly what she needs, she begs for cock, teasing with her body. His big hands reach out to smack her tantalizing bottom. Reminding her that is she want to get fucked, she's going to get spanked first! Raven MackenzieTani RogueKobe LeeBrittany ShaeKitty CatherineBettie BloemDylan RollinsMs. MystiAlex ReynoldsMiss LovecraftMackenzie ReedCleo DivineCasey CalvertSage PillarKeaganDixie CometZoe VandolofDelta HauserMiss IceniAliceAndy MoonCary NeelySophie TylorCheshire SmilesViolet OctoberMichele NolimiKajiraAngel WickyKim MulingKayleeGoverness Miss ZeeJoelle BarrosRaysi GStella MacalayLucy LaurenAshley LaneMayMar 01, 2025Isabella IIMar 01, 2025Riley ReidMar 01, 2025Krissy FTVFeb 28, 2025Ren NuisanceFeb 28, 2025Scarlett RosewoodFeb 28, 2025Yui KyounoFeb 28, 2025Josephine JamesFeb 28, 2025Lilly MaysFeb 28, 2025Kali RosesFeb 27, 2025Thomas StoneFeb 27, 2025Nata GoldFeb 27, 2025GianaFeb 26, 2025Sana LoriFeb 26, 2025Akita ThaiFeb 26, 2025Seina ReyesFeb 26, 2025Ophelia FaeFeb 26, 2025Vanessa Sky