Adding to this painful ordeal though, was the fact that Mrs Harwood the Headmistress had remained in the study for the duration of his caning. Although it was customary for two members of staff to be present whenever corporal punishment was being administered, the fact that one of them was not only female, but the Headmistress herself, was a point beyond humiliation for Alan. Although in her forties, Mrs Harwood was an extremely attractive woman. Ever since Alan had gone on a fishing trip with classmate and friend, Jonathan Elliot along with Jonathan’s father, Alan had found himself entering into what was perhaps, forbidden territory for an eighteen-year-old lad, and had begun including the headmistress in many of his masturbatory fantasies.“God, she’s got an amazing arse that headmistress of yours, pretty decent tits too, gorgeous woman, gorgeous woman,” Jonathan’s father had said as they sat patiently in the small, fibreglass dingy a mile or so from shore as they waited for the. And I have a dress with a low scoop neckline and an even shorter skirt to wear for dinner and dancing. You’ll have to stay close to me so no one can see up my … or down my … so they can’t see anything. You’ll have to protect me, Lover.’ She kissed my cheek at the side of my mouth and gently grasped my erection through my trousers. I was privately enthusiastic about her wardrobe – who wouldn’t be? But I also was surprised, because Dorothy, by upbringing and nature, was a conservative dresser. Hmmm, we each were evolving. Traffic was light as we got further from town. I turned to kiss her briefly. ‘I’ll be honored to protect you from the wandering eyes of strangers, Sweetheart. But I’m very weak when it comes to your charms – I’m going to have a tent in my trousers – a lot – because I’ll be drinking in your loveliness at every opportunity – just as I am now. Your legs are absolutely stunning and I’m looking at them hugging my hand between your kissable thighs.’ ‘Uuhhmmm, I know. That’s.
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