Chastity check up

Miss Sandra and Miss Susan enter the room. I’ve been told to take off my clothes, except for my pink lacy panties and of course the cock cage (which I can’t remove - Susan has the keys).  Sandra is my boss. She is around 30, half my age, and likes to wear professional but sexy clothes around the office. Tight short skirts, fearsome heels and tops that push her breasts right up into your eye line. She wears her raven hair bobbed and her wonderful blue eyes have a playful expression today.  

Susan is my office intern and is a nightmare. She is only 19, but is posh as hell and a mean, difficult princess, an impossible task Master.  She has long blonde hair - all hitched up in a swishy pony tail today, freckles and slate grey eyes. Since she took charge of me, her clothing has got ridiculous- entirely inappropriate for the office in my view. Her skirts are bloody tiny, completely showing off her amazing legs. I don’t know how she manages to stand on the bloody heels! You can hear them clacking down the corridor from miles off.  

The two ladies come in and sit on the chairs in front of me. I know that I have to look down, but that still allows me to see Susan’s thighs, as her tiny skirt rides right up. She dangles her heel in front of me. My willy tries to unfurl in its cage with no success.   Susan has decided that my “winky” must be shrunk until it can squeeze into a 1 inch cock cage. I think she’s got a thing about hating older male managers - she certainly seems to want to vent some serious frustration on me.

My willy used to be pretty much normally sized, but Susan is a determined young woman and she will get what she wants. I’ve been made to wear a permanent chastity for 3 months now and have already moved down two sizes. These fittings are interspersed with Susan paddling my bottom frequently, bloody hard and in the most humiliating ways. Today is chastity check up day and the ladies are determined to fit me into a Locked in Lust One Inch Pin Dick model. 

Sandra takes the new chastity out of its wrapping. She crosses her legs as she does so, and I can see a glimpse of garter strap between the top of gorgeous thighs and the hem of her skirt. She sees me look and says tetchily that I need to put the Pindick chastity on, handing it to me. The bloody thing is pink and tiny. I have got smaller under Miss Susan’s relentless supervision, but not that small!  I plead with the ladies, saying I’m happy to go down a size but that the Pindick device is way way too small.

Susan hands me the key and I try to push my dick into the new contraption. Absolutely no way - I can’t even get the top in. This isn’t helped by having a growing erection - it’s been weeks since I’ve been free and Miss Susan is bending over to pick something up, her gym sculpted buttocks almost touching my nose. “This is no good“, she says, “we need him to focus”. When she turns round, to my dismay, she’s holding the wooden kitchen spoon.  

Miss Susan delights in hurting me and is very imaginative in thinking of humiliating ways to do it. One of her paddles is lettered and leaves the word “bitch” clearly imprinted wherever it lands. She loves to show me what a beta I am, making me lift my bottom right up so that the whacks land bloody hard. She makes me say thank you and giggles as I do it.   I’m told to sit on the chair and open my legs. The kitchen spoon is the absolute worst. Miss Susan leans over until her face is close to mine. It’s hard to look in her eyes because this position means her breasts are almost in my face, in a push up bra which her boy friend made me buy for her.

“Ew, I’m going to whack your balls until that tiny thing goes down”, she says. I’m hypnotised, looking at her skirt which is the size of a belt and her pony tail swishing about as she takes a couple of steps back, spoon in hand, to get a run in at my plums. Lift your hips up, she shouts, jerking me from my reverie.   I know the drill. I’m to push up, widen my legs and raise my hips as far up as I can so that the whacks have maximum impact on my plums. This is impossible to keep up for any length of time. Miss Susan once did this to me in front of her boyfriend, who I was made to call Sir - some arrogant bloody student who thought the whole thing hilarious.

I raise my hips. Miss Susan is a keen tennis player and has a strong action. She takes a little skip, making her breasts jiggle, and brings the spoon down hard right onto my ballsack with a loud slap.   The pain is indescribable. I plead and beg but Miss Susan carries right on. After a while I begin to swivel my hips to avoid the blows - you have to - and Miss Susan gets cross telling me to bloody stay still. Sandra says I must help steady for Miss Susan because it’s a very small target and they both laugh. This goes on until Susan’s arm gets tired. She is panting, flushed, fiery eyed, standing with her hands on her hips. My stomach and balls hurt so so much. “This wouldn’t be necessary if you’d squeezed it in first time“, says Sandra, “rather than perving at us“. Her legs are still crossed, with her stocking tops on full display now.  

I’m told to try on the Pindick cock cage again. This time, with a lot of pressing, groaning and discomfort I just about manage it. My wink looks ridiculous, desperately trying to escape the cage from all sides. There is some ironic clapping from the girls and I’m told to fuck off. As I leave, I hear Sandra saying to Susan she never thought I’d get into a cage that’s two sizes too small. They both burst into laughter.