Tag Archives: Lilly Calloway

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 …

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 …

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 …

Schoolgirl Lilly Calloway has forged and faked her way onto a school trip. Discovered, Lilly must now face the consequences, a spanking from the teacher in charge and the strap …

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 …

In this comprehensive disciplinary saga, I, Miss Kelley May, guide my little Lilly Calloway through a journey of correction and redemption. This two-part video captures the full arc of Lilly’s …

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 …

“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 …

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 …

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 …