#206) Headmistress Musings

One of my favorite ways to drift off to sleep is to fantasize about being the headmistress at an all-girls preparatory school. I wouldn’t be a very good administrator, I confess; I’d discipline the poor girl’s mercilessly. The prettier and more shapely girls would certainly get it all the worse.

The schoolgirl featured above is Donna from Real Spankings Institute. Her redhead’s complexion makes her skin so creamy and fair. Coupled with the fact that she has a smart-aleck’s attitude, I know that I’d be caning her bottom frequently. And NOT with the standard “six of the best” cane stripes, either! I’d keep Donna bent over the table in my office all afternoon while I administered twenty or more wicked welts to her proffered posterior. Does she know that whipping her excites me tremendously? Does Donna suspect that while I’m whipping her, I’m reaching into my knickers, I’m touching myself lewdly? Does she notice that, as I bring her thrashing to a crescendo with the cane, I’m crying out from the finger-flogging I’m giving my aroused pussy almost as loudly as she is? Donna keeps returning to my office on a very regular basis for punishment. No sooner have the stripes from the last beating healed than there she is in my outer-office, sitting tentatively on the hard chair, knowing that she’ll be squirming soon…

The schoolgirl featured below is Cherry from Spanking Emporium. She has such cherubic cheeks; I absolutely love giving her well-upholstered backside a sound plimsole paddling as often as needed! And Cherry is in the habit of getting sent to my office for such treatment just as frequently as Donna, about once a week or so. It’s as if her plump bottom was made for paddling! Cherry whimpers so satisfyingly as I start to wallop her, breaks down into tears so endearingly, and has the endurance to take such a long, hard thrashing! After I’ve worn Cherry’s big bottom out with the sole of the gym shoe, I lecture her, caressing her burning hot and fiery red flesh, parting her to glimpse her feminine charms. Sometimes I can barely pull up her knicks and usher her out of my office before I convulse in climaxes.

I very good Friday for me is to see Donna at my door mid-morning, and then have Cherry visit mid-afternoon. Higher education can make me high as a kite from orgasmic euphoria because of these two and other misbehaving students. It’s a tough job, but someone has to do it!

8 responses to “#206) Headmistress Musings”

  1. I’m feeling elated today. I still have the skin cancer radiation treatments stretching into mid-May, but several other demands on my time & attention have just been completed. So I made two postings today, and celebrated with a lovely, long Saturday morning masturbation session. Enjoy!

    Liked by 3 people

  2. I LOVE the school girl discipline scenario…though, I am always the school girl in these fantasies. My tummy full of butterflies, knowing that I misbehaved, and knowing that I will be disciplined for that misbehavior. Great selection of photos! XOXO

    Liked by 2 people

  3. Sexy nice! If there is one thing I could use more of its deservingly naughty schoolgirls in need of firm (skirts up, panties down) bare bottom spankings along with red bottom on display corner time. Now where did I put my tweed jacket and “board of education”
    🤔🍑✋🏻

    Liked by 1 person

    • Oh, Big K, you make me wish for the best of all possible worlds where “tweedy professor-types” could be easily matched-up with naughty & deserving, nakey & mischievous schoolgirls for discipline and fun!

      Liked by 1 person

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