Reginald’s Fate

Hello Dear Slaves. Autumn is here and it’s time to wrap up nice and warm. I always find a Latex bodysuit does the trick. Maybe with a nice ballgag to keep your mouth nice and warm, a defense against the winter chill. Oh, and of course a great big buttplug to stop the wind rushing up your dirty little hole!
It was on a particularly wet and rainy day last week, that one of my regulars crawled into the dungeon. Hadn’t seen him for weeks. Thought he’d dumped me for another Mistress, but it seems he’d been “trying to give me up”. Cheeky little sod. Of course he couldn’t, men find that particularly difficult. They say I’m addictive as Heroin. I suppose I am, but you’re left on a much bigger high after a few hours with Athena.
Anyways, my little regular – I’ll call him Reginald (well, that is his name! sorry, Reggie) – was ready for his usual. I knew he would be. I was already dressed as a school headmistress because I just knew Reggie would take off his long overcoat to reveal his school uniform, complete with shorts and old school tie. Reggie actually went to Public School and the uniform matches the one he wore 30 years ago! He had it specially made, the dirty little perv!
My cane was ready for action as poor little Reggie apologized for being late for class. He sat down at his desk, nervously rubbing his hands. “I’m so sorry Headmistress. My mum forget to pack my gym shorts so I had to go back for them,” He whimpered.
“Wilson minor”, I screamed (that was how the poor sod was addressed at his old school) “this is the third time this week you’ve been late.”
Before he had time to come up with an apology, I’d slammed the desk with the cane. 
“Stand up Wilson Minor,” I said. “Bend over your desk and pull those shorts down and those disgusting little underpants.”
Poor Reggie was almost in tears as he leaned over the old desk and eased his kecks down over his nobbly old knees. The little perv was wearing tiny girl’s knickers. He always does.
“Wilson Minor. You are a filthy little wretch. Not only that, your dress as a girl, so you are a sissy too. I will tell the whole class about your perv boy,” I shouted.
“So sorry Mistress. Please don’t cane me again,” he begged. Not too convincingly as he bloody loves a few strokes over his hairy butt.
The time for talking was over, I lashed his little bum with my cane. Five time at first. He screamed half in pain and half in pleasure. The pleasure side was indicated by his impressive erection that bulged out of his panties.
Just for that, I gave him another five of the best. Red stripes started to glow across his buttocks. 
He tried to wank himself, but his headmistress does not allow that. I grabbed his hands and quickly cuffed him behind his back. No chance for dirty little Reggie to play now.
I gave him another six of the best. He yelled in pain and pleasure too. He tried to rub his engorged dick on the desk, but a few more strokes prevented this from happening again. 
Finally, he gave me his safe word, and I uncuffed his hands. Within seconds desperate Reggie was wanking himself like mad. He had pulled off his knickers and was using them to pleasure himself. Of course he came in seconds. Shouting an angry name as he did so. “Fuck you headmistress,” he screamed. I whipped him with a my trusty Strap. 
Reggie was spent. Exhausted and exhilarated. 
“You are the best,” crawled the now relaxed Reggie. Then the dirty sod asked to buy some of my used knickers. Of course I’m only to happy too oblige. I had a couple of particularly stained pairs that I keep for my best customers. His eyes bulged as he sniffed them. Worth £30 of anyone’s money I reckon!

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