Free Spanking Videos and Galleries with Winter Ryleigh, also known as Winter Leigh. We have previews with Winter Ryleigh from 4 Premium Sites.
Winter Spanked By StepmotherWinter, a college-age girl living with her father and stepmom, Clara, tests the limits of household rules. Defying curfews and riding her boyfriend's motorcycle against strict prohibitions, Winter's rebellious behavior reaches a peak when she comes home in a revealing short dress. Clara, frustrated by Winter's flagrant disregard for the rules, decides it's time for a firm, old-fashioned lesson. Watch as Winter faces the consequences of her actions through a disciplinary spanking with hand and hairbrush, meant to teach her the importance of respecting household boundaries and authority.Accomplished Liar Frequent FlyerOur spanking flight attendant series is back and Winter Ryleigh looks stunning dressed in the AAA Airlines uniform. She has been summoned to the local offices where HR manager, Miss Matthews has made a startling discovery about Winter's job application. It would appear that she had lied about her references and got others to cover up this fact so that she could complete her training and fly the skies as a flight attendant. In fact, as Miss Matthews discovers... Winter is an accomplished liar and although she was actually good at her job, this should never have happened. Having so much time and money invested in her training, Miss Matthews decides that Winter can keep her job. However, that depends on her accepting corporal discipline, the old-fashioned way... with an embarrassing spanking punishment. Winter's long legs drape over the HR manager's lap as she is spanked and her gorgeous curves are accentuated in the tight pencil skirt. The sight of her lacy panties pulled down, with her bare bottom spanked, is a spectacle to behold! Once Winter's bottom is suitably reddened, her bubble butt is given a leather strapping (her first ever) as she winces and squeals in surprise. This is one disciplinary meeting Miss Ryleigh will not soon forget!Disciplined For DeceptionThis is Winter Leigh's first appearance on Cheerleader Spankings, and also her first ever rectal temperature taking on film. It's Casual Friday and the school's cheerleaders are allowed to wear their uniform. It's also a Double-Math Day for cheergirl Winter and she doesn't want to endure that in the afternoon. Winter decides to try and fool the new British nurse, Miss Matthews, by pretending to have picked up an illness and visits the medical room to see if she can get the rest of the day off. Nurse Matthews is an old hand at seeing through a miscreant's lies and quickly deduces that the cheerleader is faking it. She decides to see how far Winter will go with this deception, even giving her a thoroughly humiliating and unnecessary rectal temperature taking for that so-called 'fever' and the desperate madam complies. Naturally, there is nothing wrong with her and the nurse eventually gets this information out of the lying cheer girl which results in a rather uncomfortable lesson courtesy of Miss Matthews' hand and leather strap across Winter's exposed bottom. She is spread out on all fours on the examination table and her bare, exposed parts are reddened perfectly until the nurse is satisfied that Winter has learned her lesson by not wasting any of the medical staff's valuable time. Double Math in the afternoon will now be even more uncomfortable for Winter since she will not be able to sit down without remembering the error of her ways!Winter Ryleigh's Hairbrush SpankingWinter's new stepmom (Miss Matthews) has been given permission to deal with her whenever and however she needs to... using the 'old-fashioned' methods of correction. This means that a rude slutty brat can, at last, be taken over her lap for a long overdue and richly deserved spanking. Miss Matthews has had enough of Winter's back talk and dressing inappropriately like a 'common harlot'. After a stern scolding about how inappropriate her new dress is for going out, she takes the stunning, naughty rude redhead over her lap for a hard-hand spanking. Winter's sassy behavior also merits the use of the Mason & Pearson hairbrush and this stinging implement of correction really grabs the young lady's attention. She wriggles and kicks over her stepmother's lap as her bottom ends up as red as her lush pin-up red hair. Her punishment ends when Winter is genuinely apologizing and promising to dress more appropriately as she assures her new stepmom that she will have a better attitude at home.Winter's First CaningWe are excited to welcome Winter Ryleigh to the website receiving her very first caning ever! Winter has been a very naughty girl who has been sent to Headmistress Matthews to be dealt with. She has received 3 demerits and that means a caning. She is soundly spanked over Miss Matthew's lap on her bare bottom before being given her first caning. She bends over the desk for some sharp strokes of the school cane.Spanking Positions - Winter RyleighPlease welcome our fabulous newcomer to our network of sites, Winter Ryleigh, in her first-ever spanking shoot alongside Clara Matthews. This is a most memorable debut appearance and we decided to showcase this natural girl next door with 3 of our classic spanking positions. Ryleigh has a perfect 1950s pin-up figure (Bettie Page is one such inspiration) as she dressed to impress with vintage lingerie in a sumptuous Living Room location. She is sprawled over Clara's lap on the classic Chesterfield sofa ready as the film starts. OTK is always the first position of choice and Clara gently turns Winter's bubble butt a gorgeous shade of pink, admiring the way she takes her first spanking. She isn't shy at all and gives feedback on her glowing bottom as the 2nd position of the Wheelbarrow Spanking sees her bottom turning darker from Clara's hand and leather teardrop paddle. Various intimate camera angles capture this full spanking experience before the final position sees Miss Ryleigh spread across the sofa on All-Fours. Her long stocking-clad legs parted and her bottom fully exposed for the last spanking and leather strapping that has her cooing in delight at the new sensations she receives. This girl is a natural and we know you will enjoy seeing her spanked as much as we did! We promise, there will be more of Winter coming to our network very soon! 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