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I was asked to go on a fly-Me-to you to see a very eager boy who wanted to serve Me diligently and with true devotion. So of course the new boy must prove his total and utter devotion to My happiness and receive a punishment with a hated implement. This one hates the hairbrush and so must receive an over the knee, hard hairbrush hammering his backside. Every boy despises the hairbrush. So humiliating to be disciplined with such a feminine implement some might think., Over a Ladies knee, exposed, rubbing against soft nylon, turned on yet embarrassed and comforted at the same time. It's so confusing and taboo by definition in My opinion. This is why I love to give a brutal hairbrushing .... this boy needs training but you can watch as his bottom turns red and purple as I spank and caress, spank and caress, choosing each brush as I go along. Some nice deep bruises appear and you can see in the mirror as I spank him, My leg entrapping him so he can't squirm away.

Using My gorgeous Kent cherry wood hairbrush and a stunning vintage clothes brush which is large and covers both cheeks very well. This submissive wants the chance to become' Miss Ruby's very good boy' - a part of My trusted inner circle, under consideration - so he must submit to the harsh punishment over My knee. I want 2 perfectly round bruises, small and compact but dark and purple on his cheeks. This means striking him over and over in the exact same spot before I part his cheeks and give him something to remember Me by. Making him think of Me whenever he sits down for the next week. I stroke and caress him throughout with My hand and the brushes, deepening his connection and submission to Me with each therapeutic motion. But deepening his pain each time too.

This spanking formed his real life punishment and reward from his entries on The List. My disciplinarian log book of the strokes owed to Me. This boys punishment continued with whipping and caning which are to be released separately.

See My other OTK clips here

Hit With The Hateful Hairbrush WMV