Free Spanking Videos and Galleries with Cupcake SinClair. We have previews with Cupcake SinClair from 4 Premium Sites.
Co-Parenting CupcakeCupcake is caught trying to play her step-mom for a fool with a skimpy dress that both Alex and her school think she should not have. A phone call reveals Cupcake's deception and decides her punishment: A spanking from her step-mom and Alex's hairbrush applied hard to her naughty bottom.Real Spankings - Exclusive Updates - Part 55Cupcake SinClair - The Prize - Part 2Something very special today! Filmed back in 2016, this is a long-format film written by and starring Stephen Lewis alongside Cupcake SinClair. Sit back and enjoy some wonderful acting as they tell a dark story that might have a happy ending for someone... or maybe just an ending! Cupcake has the misfortune to be the long-suffering girlfriend of a degenerate gambler. This time he has outdone himself by losing a stack of money in a card game to Stephen Lewis, a dangerous gangster with a sadistic reputation. In lieu of the debt, and likely lethal consequences, Stephen has demanded that he send Cupcake to his hotel room. In the sexy, slinky black dress Cupcake wears as a nightclub hostess, she enters Stephen's hotel room thinking this is going to be purely for sex, seemingly confirmed as he humiliates her and orders her to strip. She knows well Stephen's reputation; she's frightened and wants this encounter to be over as quickly as possible. Stephen has other ideas. He has outfits for her to wear and he makes it very clear that Cupcake is going to suffer punishment for the financial loss her useless boyfriend has caused him. As the story unfolds, Cupcake's loyalty is severely tested, as well as how much punishment and humiliation she can take: a humiliating diaper position spanking in a school summer dress; a caning in sexy, silky lingerie, all the while being reminded how she ended up in this situation, and how much better her life could be... should be.Cupcake SinClair - The Prize - Part 1Something very special today! Filmed back in 2016, this is a long-format film written by and starring Stephen Lewis alongside Cupcake SinClair. Sit back and enjoy some wonderful acting as they tell a dark story that might have a happy ending for someone... or maybe just an ending! Cupcake has the misfortune to be the long-suffering girlfriend of a degenerate gambler. This time he has outdone himself by losing a stack of money in a card game to Stephen Lewis, a dangerous gangster with a sadistic reputation. In lieu of the debt, and likely lethal consequences, Stephen has demanded that he send Cupcake to his hotel room. In the sexy, slinky black dress Cupcake wears as a nightclub hostess, she enters Stephen's hotel room thinking this is going to be purely for sex, seemingly confirmed as he humiliates her and orders her to strip. She knows well Stephen's reputation; she's frightened and wants this encounter to be over as quickly as possible. Stephen has other ideas. He has outfits for her to wear and he makes it very clear that Cupcake is going to suffer punishment for the financial loss her useless boyfriend has caused him. As the story unfolds, Cupcake's loyalty is severely tested, as well as how much punishment and humiliation she can take: a humiliating diaper position spanking in a school summer dress; a caning in sexy, silky lingerie, all the while being reminded how she ended up in this situation, and how much better her life could be... should be.Spanked And Caned At WorkCupcake Sinclair has shown up for her first day on the new job wearing a cute little dress. Mr Lake is far from impressed. This is not the kind of attire that his employees represent his company in. She learns quickly about the companies ways of discipline if she wants to keep her job. She is spanked hard and then given 12 hard cane strokes.Curfew CaningCollege girl Cupcake returns, very late, from a night out to be met with a furious reception for breaking her curfew. She has been warned of the consequences of doing so for a second time: a severe punishment. Having had her bottom smacked hard, Cupcake must now endure a caning on her bare bottom before being sent to bed, with the promise of further discussions on the subject the next day.Exclusive Education 14 - Volleyball Team SpankingExclusive Education Year 14 is here. It stars Snow Mercy as the volleyball coach who must deal with her team fighting and all ganging up to spank tall beauty Alice Goods, who they blame for losing their recent match. Snow spanks each girl over her knee while the others watch. She then allows Alice to spank each of her naughty teammate over her knee with a hairbrush. Finally Snow paddles Elori and Cupcake, the instigators. Lots of excellent spankings all in one massive scene.A Chance To Own Up - Part 1+2An end-of-term exam paper has disappeared from the Head of Physics' tutorial room. At the time of the disappearance four girls were unsupervised in the room, where the exam paper was in a desk drawer, for just five minutes. One of them took it and they all know which. This is clearly the most serious of disciplinary matters and the Head of Physics is well-known for his uncompromising attitude towards using corporal punishment on his students when, (never if), they deserve it. Dr Kennedy announces his intention to spank them, each in turn, until one of them owns up. Needless to say, that girl may expect to be severely punished. Apart from the usual protestations about innocence and fairness, none of them say a word during the spanking.A Hand In Her PunishmentCupcake SinClair has been dragged into the hallway by her teacher, Paul Kennedy. Cupcake has been disruptive in class... again. Mr. Kennedy carries a tawse on his shoulder under his jacket when teaching, and he takes it out to put it to good use. He makes Cupcake face the wall and lift her skirt, then applies the tawse to her bottom immediately, without any warm up. Cupcake whimpers and protests, but she takes a hard leathering, first across her white school panties and then on her bare bottom. But eventually, Cupcake reaches her hand back to try to stop the punishment. When this happens, Mr. Kennedy decides that he will be shifting the style of Cupcake's correction, and makes her turn around and put her hands out one at a time to have them strapped. Cupcake takes eight hard strokes of the strap on her hands, making her crumple over in pain.Off Key - Group PunishmentMiss Kelley May is a young choir director taking a group of students on an overnight trip to the other side of the state for them to perform. She's accompanied by Mr. Lewis: the choir director for their entire district. The girls were instructed to get some rest the night before the performance, with the two soloists, Maddy Marks and Cupcake SinClair, given a special room in hopes that they wouldn't be disturbed. Unfortunately, Maddy is a bit of a ringleader among the other girls, and she strongarmed straight-laced Cupcake into throwing a party with a few of their friends. Adriana Evans, Nuna Starks, Ava Nicole, and Harley Havik showed up. Wine coolers were procured. Clothes were removed. Spin the bottle was played. The girls weren't expecting to be caught in this state, but with all the noise they were making, maybe they should have been. Both Miss May and Mr. Lewis arrive at their room, and Mr. Lewis has a cane in his hand. After both their teacher and their director scold them about this behavior, Miss May announces that they need spankings to get them back under control. And that's exactly what happens: Miss Kelley takes a seat on the sofa and pulls one girl across her lap and Mr. Lewis pulls out a straight-backed chair in order to put another one in the same position and each girl is soundly spanked, first on their tight-fitting white panties and then on their bare bottoms. But one spanking is not enough: after being spanked by one of their authority figures, each girl is sent to wait in line for punishment from the other. Two hard spankings leave the girls rubbing and wiggling, and looking very contrite indeed. But Cupcake and Maddy were truly responsible for this whole debacle, and Mr. Lewis feels that the two of them should know better than to have behaved the way they did. So, with all eyes on them, Cupcake is made to bend over for a caning. Maddy is next, and receives even more strokes since she was the one who started the whole thing. Then, it's off to bed for all of the girls. Hopefully, a lesson was learned and there won't be any further problems from these sorry schoolgirls!Exclusive Education 12 - Day OneTeacher Snow Mercy is getting her class ready for a field trip when she finds them acting up. She, along with new Principal Clare Fonda, decide to give the girls some discipline to make sure they behave on the trip. So Snow and Clare take turns spanking each of the naughty school girls, over their knee in the break room. The first day is some very sound hand spanking that turns these glorious bottoms bright red. The naughty ladies are Ashley Lane, Elori Stix, Cupcake Sinclair, Apricot Pitts, Alice Goods, Veronica Ricci and making her spanking debut, the feisty Joy Luck. The is Part 1 of a 4 part epic that will include 12 amazing ladies in total.Tea & SpankingOver their weekly tea and cookies, best friends Alex and Cupcake discuss the latest developments in their love lives. Alex is distraught to hear that Cupcake has, once again, disclosed details of a new relationship that Alex had hoped to keep under wraps. This time Alex has had enough and determines to curb her friends gossiping habits once and for all. Without further ado, Alex turns Cupcake across her lap and administers a sound spanking with her hand and a solid wooden clothes brush.By Order Of The Court - Part OneThis is a 40min film featuring Cupcake SinClair, Harley Havik, Violet October and Alex Reynolds. Four girls convicted of offences of violence and prostitution are sentenced to severe corporal punishment by the court. The method is strict; All must strip and in turn be taken to the punishment room to receive their beating. We have only visited the judicial theme once before, many years ago. We hope you enjoy our latest effort, featuring as it does three of our gorgeous new spanking starlets!A Good FriendAlex likes to look out for her little sister, so when she finds out that her best friend, Cupcake, has been seeing her boyfriend behind her back, she is very upset. Confronting Cupcake on her behaviour, Alex knows there is only one solution, a very sore bottom indeed for her little sister's bad friend. 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