Lilly and Kelley are long-time real life friends and play partners (Lilly is one of Kelley’s bridesmaids!), who have a special dynamic. Specifically, Kelley has been punishing Lilly for various …
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Kelley May, Lilly Calloway – Panties Are NOT Optional – Northernspanking
Recently introduced, this is Lilly’s first ever spanking film and we are delighted that she chose us to fulfill a long-held ambition. You will be seeing much more of this …
Read More »Lilly Calloway – How To Punish A Princess – Northernspanking
Private detective Kennedy is on a revenue protection gig for a casino. Having studied her gambling habit carefully, and done some digging, he visits Lilly unannounced in her room and …
Read More »How To Survive Hazing – Spankedanddiapered
Lilly Calloway is a beautiful, popular sorority girl. Her little sister, Lola, is just getting to be college-aged herself, and she’s always looked up to Lilly. She’s excited when her …
Read More »Slacking Off – Northernspanking
Lily takes her schoolgirl daughter Jess to work for the day and soon comes to regret it. Instead of learning something about the hospitality industry that is her mom’s chosen …
Read More »Lilly Calloway – Summer Of Swats – Universal Spanking and Punishments
“Summer of Swats” is the follow up to “College Girl Strapped” and Stars the bratty and beautiful Lilly Calloway. Previously, Lilly was caught in a scandal where several college girls …
Read More »Wet Little Sister – Spankedanddiapered
File Name : Wet Little Sister.mp4 File Size : 488.53 MB Resolution : 1920×1080 Duration : 00:13:16 Video : AVC, 4 979 kb/s, 59.940 (60000/1001) FPS Audio : AAC, 160 …
Read More »Naughty Ella Gets A Spanking – Spankedanddiapered
Lilly Calloway is babysitting Ella Raine. Lilly is a wicked girl who starts humiliating and regressing her young charge. After babytalking to Ella about how little she looks in her …
Read More »Girls Night Out – Spankedanddiapered
Strict mom Lilly is so disappointed when her daughter, Kiki, and her best friend, Anastasia, get caught trying to get into a club with fake IDs. She drives to the …
Read More »Do Not Disturb – Northernspanking
Lilly’s morning is not off to great start. Somehow, the “Do Not Disturb” sign got removed from her hotel room door and she is loudly wakened by housekeeping. Shortly thereafter …
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