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There will be more! Don't miss our updates for Lily Swan!Stay informed by EmailCheerleader SpankingsLily SwanPaul Rogersspanking, m/f, otk, uniform spanking, cheerleader, wooden paddle
May 09Mascot Misdemeanor
What did Lily think would happen when she stole a rival school's treasured mascot and took it home to hide? Her tight panties are pulled down and her red buns are smacked harder before she is told to bend over the chair, presenting her bottom for the paddle.Momma SpankingsLily SwanKatherine Worthingtonspanking, f/f, otk, hairbrush
Lily's Bedtime Spanking
Mommy is not happy with Lily and takes it out on Lily's tight, bare bottom with a mean, hard hand spanking. This punishment is far from over and to teach this brat a lesson she will remember, Mom uses a hairbrush to teach her girl that laziness has consequences.Cheerleader SpankingsLily SwanAndy Moonspanking, f/f, uniform spanking, cheerleader
Never Be Late Again
Andy is taught that there will be no lateness tolerated in the future or there will be more painful consequences. For those that like to see a hard uncompromising hand spanking punishment, this is the one to watch... coach Lily Swan really does have a mean hard hand!Spanking 101 VideosLily SwanAva NyxPaul Rogersspanking, m/f, otk, uniform spanking, cheerleader, humiliation
Ava's And Lily's Long Schoolday - Part 11
Sassy sisters Ava Nyx and Lily Swan stay in trouble all day long with firm Principal Tubaman. By the end of the day, they have received an ass-searing 21 (!) spankings, strappings, and paddlings. These two young ladies will be attending their classes standing up for the foreseeable future.Cheerleader SpankingsLily SwanJas JayBirdspanking, f/f, otk, uniform spanking, black girls spanking, cheerleader
Spanked For Divided Loyalties
Lily Swan takes errant young lady Riley across her lap, lecturing her while given a spanking over her tight panties. However, she knows the best lesson is learned on the bare and pulls down those tight panties and starts to spank Riley's quivering buttocks even harder.AAA SpankingLily Swanspanking, m/f, strap
Lily's Living Room Discipline
Lily Swan has really done it this time... She is spanked over her tight leggings, her toned thighs and bottom rippling underneath the thin material... until her bottom is bared for a hard hand spanking in the plank position and lifting weights spread out on the floor.Sarah Gregory SpankingLily Swanspanking, m/f, otk, uniform spanking
Lily's Red Shameful Bottom
Stepdad takes Lily over his lap for a much deserved punishment. She is spanked over her regulation school knickers, then on her bare bottom. After a hard over the knee hand spanking, stepdaddy takes his belt to the girl's already sore bottom.Cheerleader SpankingsLily SwanKajiraspanking, f/f, uniform spanking, cheerleader
Kajira Goes Too Far
Kajira admits that she did what it takes to get the highly coveted position by giving her coach a blow job... Lily decides to punish Kajira and she does what she feels is necessary by giving her slutty friend a hard hand spanking.AAA SpankingLily Swanspanking, leather paddle, hairbrush, self spanking
Lily Spanks Herself Hard!
Lily has 2 implements, a leather paddle and a hairbrush which she uses as well as her own hard hand. Watch her bottom turning red before your eyes as she relentlessly whacks her cheeks for your viewing pleasure. This spanking turns her on and she imagines that you are there with her.Cheerleader SpankingsLily SwanReyna St. Clairspanking, f/f, otk, uniform spanking, cheerleader
Sassy Bratty Reyna Spanked
Coach Lily Swan has a private showdown meeting with Reyna after the latest disastrous practice thanks to this spoiled brat. Reyna's bottom reddens in shame as the coach's hard hand smacks this sassy, spoiled brat's jiggling booty.Momma SpankingsLily SwanMiss Elizabethspanking, f/f, otk, hairbrush
Lost Panties Spanked Bottom
Mommy is shocked when she pulls up Lily's dress to find no panties... none at all! Lily is ferociously hand spanked and then with the wooden hairbrush which really stings, making Lily yell even louder. Her bottom turns a dark shade of crimson and marks at the hard strokes of the brush.AAA SpankingLily SwanSamantha Bspanking, f/f, strap
Lily's Well Deserved Punishment
Mom wastes no time taking Lily over a chair to spank Lily's bare toned cheeks. They quickly turn a shameful red and the family strap, a new stiff leather implement is then used on the insolent girl's sore buttocks. Lily yelps and cries out in pain as the leather turns her bottom a darker crimson.Cheerleader SpankingsLily SwanAmy Foxspanking, f/f, uniform spanking, cheerleader, wooden paddle
Amy Wrong Footed By Coach
The sassy cheerleader is laid out flat over the wobbling table with continual, hard hand swats across her bare bottom with withering scolding remarks from the assistant coach! The hand spanking quickly leaves Amy's cheeks a shameful red but this is far from over.Momma SpankingsLily SwanSamantha Bspanking, f/f, otk, hairbrush, uniform spanking
Lily's Afterschool Spanking
Lily confessed to Father O'Mally about smoking 'Pot' with friends. Lily is taken over mommy's lap and given a spanking whilst still in her school uniform pinafore dress, then over her starched navy regulation school knickers, and of course... as always at home, on the bare, jiggling bottom.Cheerleader SpankingsLily SwanSarah Gregoryspanking, f/f, otk, uniform spanking, cheerleader
Booty Shaking Spanking
Witness the beauty of 2 hot ladies in their colorful uniforms, with Sarah over Lily's lap getting a well-deserved spanking over her tight-fitting shorts. Of course, to learn her lesson and without the dignity of wearing her shorts, she receives a mean bare bottom hand spanking too.AAA SpankingLily SwanSarah Gregoryspanking, f/f, otk
Lazy Lily Slut Shamed And Spanked By Sarah
Watch Sarah enjoy humiliating and taking control of Lily as she slut shames and spanks her helpless roommate, legs splayed and reminding her who is in charge! This is such a hot spanking scene, Lily's bottom really turns a burning red and Sarah plays with her like a cat would a mouse!Cheerleader SpankingsLily Swanspanking, m/f, otk, hairbrush, uniform spanking, cheerleader
Lily Spanked For Skipping Practice
Lily skipped practice to hang out with some weight-lifting guys. Dad is furious and tells her it's high time she received an old fashioned spanking across his lap. He spanks her so hard it quickly turns her bottom a flaming red. Lily is left to reflect on her punishment in the corner.Sarah Gregory SpankingLily Swanspanking, m/f, otk, strap, paddle
Dominatrix Dominated
Lily Swan doesn't like being spanked and strapped one little bit but John is having far too much fun especially since she tried to pull one over on him. Watch her athletic, toned legs kick out and her strong body struggle as John spanks her beautiful jiggling cheeks.Cheerleader SpankingsLily Swanspanking, m/f, otk, strap, uniform spanking, cheerleader
All Your Fault
Lily's tight panties offer no protection from his hard hand and he removes these, embarrassing Lily further as her reddening bottom is spanked on the bare. She is placed over the desk, bottom out, and given a double strapping with 2 leather implements.Spanking 101 VideosLily SwanPaul Rogersspanking, m/f, riding crop
Lily's Long Week - The Riding Crop
Lily Swan finds out very quickly that misbehavior will not be tolerated, and that attitude is quickly and firmly dealt with. By the end of the week, she has been cropped, strapped, paddled twice, and spanked OTK an ass-searing eight times, and her attitude is significantly changed!AAA SpankingLily Swanspanking, m/f, strap, pyjamas, carpet beater
Dirty Defiler Disciplined
This is another excellent 'Catholic Discipline' films. Ecstatic moaning is coming from Lily's room... and she is caught by Mr. Osborne with her pajama pants pulled down and her fingers dipping into her 'devil's gateway' reading what appears to be contraband and highly illicit BDSM literature!AAA SpankingLily SwanSamantha Bspanking, f/f, otk, hairbrush, pyjamas, rectal thermometer, humiliation
Lily's Humiliating Punishment - Images Preview
The lying daughter is left to contemplate her foolish actions... and she is still going to school that day with a very sore reminder that 'Mom knows best!' This film features Lily's first-ever, and possibly only, rectal thermometer temperature taking scene!Cheerleader SpankingsLily SwanAdriana Evansspanking, f/f, otk, uniform spanking, cheerleader
Lily Taught A Lesson
Adriana Evans spanks Lily Swan, stood up against the wall, and quickly removes a struggling Lily's white panties and continues to spank the sassy cheer girl... until her bottom starts to turn a shameful red.Cheerleader SpankingsLily SwanMadison Swanspanking, f/f, otk, hairbrush, uniform spanking, cheerleader
Spanked For Fighting
The eldest, Lily, is first to go over her mom's lap as her toned, round cheeks are given a hard hand spanking both over and without the dignity of her tight shorts. You can imagine how embarrassing this is for her to know the younger sis is watching her bottom getting spanked like that.Sarah Gregory SpankingLily SwanAva NicolePaul Rogersspanking, m/f, otk, uniform spanking, wooden paddle
Lily And Ava's School Punishment
Lily is first and she howls as his hardened hand reddens her bare bottom with her regulation school panties pulled down. She is sent back to the wall while Ava takes the same position, she kicks and yelps as she receives the same humiliating treatment.AAA SpankingLily SwanSamantha Bspanking, f/f, otk, hairbrush, pyjamas, rectal thermometer
Lily's Humiliating Punishment
Caught in her own web of lies Lily reluctantly presents her bottom for inspection and having the thermometer inserted rectally. This proves to Mom that she is faking ill and she grabs the nearby hairbrush next to Lily's bed insisting her daughter be punished for lying to her.Cheerleader SpankingsLily SwanSamantha Bspanking, f/f, hairbrush, uniform spanking, cheerleader
Thieving Lily's Liquor Lickin'
She places her daughter, still dressed in her cheer outfit, over the table and spanks her hard whilst scolding her naughty girl. Those tight white shorts are pulled down and Lily's beautiful toned butt cheeks are given a further licking from mom's mean hands. Oh, the shame and humiliation!Sarah Gregory SpankingLily SwanMadisonspanking, f/f, wooden spoon
Competitor's Corporal Punishment
Madison confronts Lily about why there are needles and steroids being planted in her locker and bag. Madison has a plan, to spank Lily good and hard until she agrees to confess to the coach that she has been the one planting the drugs and gives a sincere apology.AAA SpankingLily SwanDelta Hauserspanking, m/f, caning, severe
Judicial Canings of Delta and Lily
This is a very severe custom caning with an accurate and well delivered caning with the precise amount of deliberate humiliation from the medical staff to ensure this entire punishment is an extraordinary and unforgettable piece of film making.AAA SpankingLily SwanRaven Mackenziespanking, f/f, wooden paddle
Personal Training Punishment
Raven takes a hand spanking over her tight leggings and then with her panties pulled down, bottom fully exposed as she is spanked on all fours. She starts to feel the burn and sting of Lily's hard hand, but there is more...AAA SpankingLily Swanspanking, m/f, caning, otk
Spanked Strapped and Caned into Shape
Lily is spanked over her tight yoga pants as she squirms and wriggles over his lap before they are pulled down for a far harder and more embarrassing bare bottom hand spanking. However, this is nothing compared to the heavy leather strapping and caning she receives next!Cheerleader SpankingsLily Swanspanking, f/f, otk, hairbrush, uniform spanking, cheerleader
Spanked For Streaking
She makes her daughter to ask her to use the hairbrush on her bare bottom... how humiliating is that? Poor Lily cries out in pain, feeling embarrassed and the pain of the 'thwack' of the nasty, relentless hairbrush spanking.Cheerleader SpankingsLily SwanAva Nyxspanking, m/f, otk, strap, uniform spanking, cheerleader
Thieving Troublemakers Punished
Their attitude stinks, their morale is low and a competition is near... Ava and Lily need to be taught a lesson. Ava is first, taken over the lap of Principal Rogers as his hard hand smacks her tight bottom, making her squirm and kick her legs.AAA SpankingLily SwanDelta Hauserspanking, m/f, caning, severe
Judicial Canings Of Delta & Lily
This is a very severe custom caning with an accurate and well delivered caning with the precise amount of deliberate humiliation from the medical staff to ensure this entire punishment is an extraodinary and unforgettable piece of film making.Momma SpankingsLily SwanSarah Gregoryspanking, f/f, otk, strap
Lesbian Lovers Spanked and Strapped
Lily and Sarah are busy having sex on Sarah's bed when mommy comes home. She is appalled that what she thought was her innocent daughter having sex. She takes each naughty girl over her lap for a hand spanking before administering the family strap nice and hard to their sore red bare bottoms.AAA SpankingLily Swanspanking, f/f, otk, paddle
Bratty Stepdaughter Punished
Lily's thighs and bare bottom are whacked hard and without mercy and the red bruising easily shows up on her legs. Thus endeth the lesson for Lily: Do not to wear such provocative clothing, be better behaved, and definitely go find some panties!AAA SpankingLily SwanRaven Mackenziespanking, f/f, wooden paddle
Personal Training Punishment
She starts to feel the burn and sting of Lily's hard hand, but there is more... Lily also uses other implements when needed, so until their next meet in seven days, she gives Raven seven hard swats with a wooden paddle stick to remind and motivate her new client!Cheerleader SpankingsLily SwanRaven Mackenziespanking, f/f, otk, cheerleader, wooden paddle
Raven Spanked by Coach
Placed over the sofa, Raven's bottom is vulnerable and exposed as the wooden paddle hits its target again and again. This is one very sore, sorry cheerleader who has plenty to think about if she wishes to remain on the squad!Sarah Gregory SpankingLily Swanspanking, m/f, leather paddle
Attitude Ass Whooping
Lily is being a complete bitch to everyone in the club. Girls are complaining about her as well as the customers and even the DJ. Her boss calls this sassy stripper into his office to teach her a lesson and show her what will happen if she continues to have an attitude.Sarah Gregory SpankingLily Swanspanking, m/f, otk, strap, severe
Lily's Painful Lesson
Lily isn't very happy to get a hard bare bottom spanking and strapping when Dad discovers she comes back after curfew. Not only is she late, but she is dressed like a slut and has no panties on. Lily is a fighter and dad has to leg lock her down.Sarah Gregory SpankingLily Swanspanking, m/f, caning, uniform spanking, classroom
Late for Detention
She was already going to get a spanking, but now she will get a caning as well. Lily is made to bend over her desk for a bare bottom spanking before a good old hard caning. Lily will soon remember to behave in school and show up to detention on time.AAA SpankingLily Swanspanking, m/f, caning, strap, tattoos
Spanked Strapped and Caned into Shape
Fitness and Lifestyle Coach, Lily Swan, has been feeling sorry for herself by eating junk food instead of her usual strict dietary regimen that she teaches others. See Lily Swan in another hot video punishment from our special 'Exercise and Discipline' series.AAA SpankingLily Swanspanking, m/f, otk, jeans spanking, tattoos
Brewing Up Trouble
He gave her a spanking that made her bare bottom sore and she knew she had to take this hard spanking for her obvious deception and lack of respect toward her trusting landlord!AAA SpankingLily Swanspanking, m/f, caning, severe, paddle
Pain Slut Maintenance
Lily Swan requires a routine of various spanking and maintenance punishments to keep her rebooted and she is never happy unless her bottom has a constant reminder of further consequences in her private life if she strays from her disciplinary path.AAA SpankingLily Swanspanking, m/f, caning, strap, severe
No Pain No Gain
He strapped her hard making her perform her precious PiYo moves before using the cane whilst she reverted to Abs & Core Strength exercises such as The Plank which was made so much more difficult with the cane biting into her very sore red welted bottom.Free Sites featuring Lily SwanAAA Free Spanking GalleriesAAA Spanking Free VideosPaul Rogers Free Spanking 101Spanked GirlsSpanking24 Daily UpdatesUniform SpankingTheme collections featuring Lily SwanGirls Self Spanking PunishmentsRectal Thermometry before SpankingPremium sites featuring Lily SwanAAA SpankingCheerleader SpankingsMomma SpankingsSarah Gregory SpankingSpanking 101 Videos
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Addie JuniperRio IIKami RobertsonPaola HardKay RichardsIris SunLinny LaceClare FondaBambi BelleMoeka KuriharaKiki CaliKotomiJessicaIroha TsubakiZazieKaelahAdriana EvansNuna StarksDorothy BurnettJessica FTVJas JayBirdMaria FTVYurinaCasey CalvertSybil KuechlerChloe FTVIsabellaAngelica VeeRia KurumiArielZafiraAoi YuukiNikeAlice WayneDr. LompSofia SaintGracie FTVAmelia Jane RutherfordHyley FTVRaye FTVSinn SageReeseSierra II FTVStevie RoseNanamiMiriyaPeaches RSAshleyLOAD MORESEARCH MORE