Tag Archives: Miss Matthews

Throwback to Annabelle getting a walloping in November. It will surely be her turn again soon… File Name : Throwback to Annabelle getting a walloping in November.mp4 File Size : …

Final hairbrush spanking for @annabelletrouble (Annabelle Trouble Maker) Another video of the lovely Annabelle Trouble getting the discipline she so deserves and desires. Enjoy. File Name : Final hairbrush spanking …

We are excited to welcome Winter Ryleigh to our website receiving her very first caning! Winter has been a very naughty girl who has been sent to Headmistress Matthews to …

Having been previously chastised by Miss Matthews (Clara Hewitt, missmatthews123), Sophia (Sophia Myers, Sophia Quinn) discovers messages that mean she can get her own back on her employer with wedgies, …

Cheeky young Dilan has raided the staff room drinks cabinet, got soaking sozzled and now stinks of booze! She’s rapidly sobered and scrubbed clean in a hot soapy bath by …

Bella sits in Headmistress Scarlet’s office between the stern lady and her own mother. Mother is to be informed that Bella’s grades have been slipping and she has been caught …

Dylan has been such a disrespectful brat and her new stepmother, Bernadette, has had enough of this behavior. She has permission to take matters into her own hands and teach …

Winter’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 …

The spanking fun continues at the Sapphire Club. Controlling their gambling habits being the order of the night for both Miss Prentiss and Lady Cavandish- as both come in for …

Willow’s chores for the day as a nanny are finished and she is about to go out, dressed in a sexy outfit. The lady of the house, Clara, walks in …