It was the end of a very long month that you'd spent self-locked in chastity trying to push yourself. Previously you'd only lasted a week but now, after 31 days in the cage you were satisfied with your record and looked forward to the mind blowing orgasm waiting once you got home from work.
Then she sat down opposite you. You looked at her in stunned silence, that dress... those boots, she was like something out of your fantasies.
"This might sound strange but... are you in chastity? I'm usually great at spotting locked up boys and the way you squirm from the train vibrations is undeniable."
"I, uh, I..."
"Let's take that as a yes. From your age you can't have much experience, I bet you carry the keys with you don't you? Just say yes Miss if I'm right"
"Yes Miss..." You just about managed.
"I thought as much. I bet you'd like to give them to me, wouldn't you?"
"I...", she frowned at me, "Yes Miss"
I wasn't sure what possessed me, but from my wallet I quickly retrieved the keys and placed them in her open palm, before she slid them into her purse and took out a slim piece of paper.
"Good boy, I can already tell you're going to be a special one. This is my number," she handed me the paper, "wait a month, and then call me. A day sooner, or later, and I'll toss the keys away and you can stay in the cage forever."
Again I was all but speechless and could only think to say "Yes Miss" and without another word she stood up and rejoined her friends at the end of the carriage before getting off at the next stop. It looked as if my orgasm tonight, and for the foreseeable future, was cancelled...
Squirmy worm
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Cute and strict…
Don't be silly, honey. Of course I won't unlock your chastity cage today. You have to stay locked for at least another month. Technically now two, as punishment for release begging. Why? Because, I say so, silly boy.
Here was your chance, stud. The Madam was offering herself on a plate as you stood over her. The sluttiest red boots, squeaking as she adopted her submissive pose…….wiggling her tight ass in those killer shiny leggings.
All you had to do was unzip her pants, unlock your chastity cage, unbuckle your straitjacket, ungag yourself and then get to work. Oh, and somehow take that fat butt plug out too.
Perhaps she was setting you up to fail…..I guess that pathetic whine from behind that dildo gag buckled down your throat confirmed your failure. But don’t worry, I’m sure that she’ll roll over on to her back, unzip those pants and let you watch her finger fuck herself as you stay locked and loaded. A stray little gloop of precum might escape your cage and you know what means?
You get fuck all.
An important lesson i always teach to my pupils is:
"If you’re not getting any enjoyment out of the torturing and the suffering of the slaves, then the whole thing would just be a lot of noise and a big mess to clean up after."
Raw || March 07 - 2022
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