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Disobedient sissies who do so are caned by their respective Head-Girl, caged for one week and caned each day for that week; this sissy is waiting by matron’s office; she’ll have a final caning from her and her pathetic dick will be released. The irony of the punishment is she’ll be aching to come after a week of canings, so Matron will take her to Mistress Bow’s office and she’ll be made to masturbate before her as a final humiliation.” Pepper’s anus clenched at the plug and her little cock stiffened at Grace’s words; her enjoyment and approval of the scenario was all too evident in her tone, and the thought of a caning, and then being made to masturbate before such a stern woman gave the sissy a submissive thrill as she took in the foreboding atmosphere of her new home Tomkins took them up several flights of stairs until she reached a long corridor in the apex of the roof of this part of the huge building; she opened a door to a room within which were four double beds; Pepper had. ....it took two or three passes in broad daylight before I could walk in without some blond girl being too close and giving me a weird look. I slipped inside and got some more cash out of the atm before doing a little more shopping. I managed to find a small mini (more like micro) skirt, a medium flesh cock butt plug, and a bottle of KY jelly. Unlike at the Victoria's Secret counter, there was no judgment at Danny's...just a shrug and look that said "whatever gets you off." By the time I got back to my hotel room it was already close to dark.....I gave my parents a quick and awkward phone call and I hurried off to get a shower. I shaved every inch of me while I washed off, and before climbing out of the shower I grabbed the bottle of KY and the new toy. I started working the KY around and into my tight pink hole with one finger. Then I added a second as my ass slowly stretches around my invading members.After a few minutes of teasing my own ass I open the package for this new toy. It.
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