When I returned to the living room, Mistress had me stand in front of her.
Taking my body in her hands, she pulled my balls through the ring of my chastity cage, followed by sliding the cage onto my penis, and locking it in place.
“OK little man, I have a task for you.
Tomorrow at eleven am, you are to got to this address, and ask for Mr Green.
We are going to a party on Saturday evening, and you are going to be fitted for a proper tuxedo.
You are not to worry about the cost, it is all paid for.
Do not be late, Mr Green will report back to me on how the fitting went, along with your demeanor.
I want you to understand, your behavior is a reflection on me, do not disappoint me.
Now you need to get dressed, and head home, I will call you tomorrow afternoon, with details for the party.”
The next morning I stood in front of the shop I was asked to visit.
It was a nondescript shop front, the only indication of what type of business was conducted inside was a sign that read “Costumier”, below that a smaller sign read “Seville Rd England”.
Upon entering, a small brass bell above the door tinkled as the door hit it as I opened the door.
Once inside I was impressed as I observed row after row of fabrics on racks that lined the walls of the shop.
From behind a curtain came an elderly gentlemen, who bid me welcome.
When I informed him that I had an appointment set up for a fitting, his eyes lit up, along with a wide smile.
“Good morning young man, your Mistress has called ahead to inform me of her needs, and the style of tuxedo she desires you to be fitted for.
If you will follow me, we can begin by taking your measurements, if you will step behind that curtain, we can begin.
Miss Lisa, will you take the measurements, while I jot down the information.”
Miss Lisa entered, causing my mouth to hang open.
Miss Lisa was a middle aged woman whose very presence emitted class, along with an air of command.
She had long brunette hair, and the deepest blue eyes I had ever encountered.
“Alright young man, please remove your clothes and stand on the platform in front of that mirror.”
Looking over at Mr Green, he just nodded and told me to follow Miss Lisa’s directions.
Undressing was an experiment in embarrassment.
When I was down to my boxers, I stood upon the platform awaiting to have this done and over with.
“Young man, please remove your shorts, there is nothing to worry about, it’s necessary to accurately record your measurements.”
Sliding my boxers down, and away, I stood there holding my hands in front of my crotch.
“Young man, place your hands at your sides, and leave them there until told otherwise.
If you fail to cooperate, we have your Mistresses permission to correct your behavior.”
Dropping my hands, I stood there on display as Miss Lisa stepped forward.
Beginning with my neck size, Miss Lisa read off the measurements, while Mr Green made note of the sizes.
Working her way downward, Miss Lisa made enough measurements to blueprint a cruse ship.
Kneeling at my feet, she began to run the tape measure up the length of my inner leg, from the heel to my crotch.
When the tape reached my cage, Miss Lisa took hold of my balls, and cage while lifting them out of the way of her measuring tape.
The most obvious effect was my little penis trying to get hard, at least until the cage exerted it’s will.
Dropping my cage, Miss Lisa apologized for creating my discomfort.
“Mr Green, I think we have enough information to begin crafting this young mans tuxedo.”
turning towards me she told me to dress, and the tuxedo will be ready on Friday, and will be delivered to my apartment then.
Dressing, I made my way out of the shop, and headed home.
Once in my apartment, I changed into a pair of running shorts, and a tee-shirt.
Once I was comfortable, I set out to finish up most of the homework assignments I needed for the next days classes.
Shutting down my laptop, I sat there thinking about the strange twists, and turns my life has taken in the last week.
Sitting there, I was shaken out of my introspection, by a knock on my door.
When I opened the door, I found my lab partner Jill wanting to talk about the project we were working on for our engineering class.
“Jill, come in, I was just finishing up on some school work for my Psychology class.
I swear, if I have to research any more obscure psychology studies, I’m going to need a shrink myself, LOL.
Have a seat, we can go over the schematics for the project.
Would you like anything to drink?”
Jill said that a cold glass of water would be just the thing.
Returning from the kitchen, Jill was staring at me with an odd look, as I handed her the glass.
Sitting side by side, we went over the schematics, trying to figure out what had caused our breadboard to fail, and release the mysterious blue smoke from some of the components.
It took me a bit to notice that Jill kept looking at my crotch.
“Tom, I need to ask you a very personal question, and I don’t want this to seem weird, so here it goes,
Tom, are you wearing a cup, you know an athletic supporter?
The only reason I ask is that there is an outline in your shorts that doesn’t look quite right.”
OK, so now I sat there with a stunned look upon my face.
I hadn’t realized that my cage was creating such a noticeable outline.
In my attempt to extricate myself from this situation, I did the only thing I could think of in the moment.
I stuttered like a damn fool, with my face turning every shade of red on the color chart, I attempted to redirect the conversation, which of course failed miserably.
“Tom, what’s wrong, I’m sorry if I upset you, it’s just that it didn’t look right.
When you stood up to get my glass of water from the kitchen, I thought I saw whatever it was swaying back and forth as you moved.”
As I sat there at a loss for the words I wanted to say, Jill reached over, and placed her hand atop my crotch.
It was there for only the briefest of seconds before she yanked it away, with a puzzled look on her face.
“Tom, what is that thing?
It feels like, well I don’t actually know what it feel like, but it’s certainly not a sports cup.
Tom, are you going to talk to me, or just brush this off?
Whatever it is, whatever the problem you can trust me to keep my mouth shut.”
Screwing up my courage, I began to sputter out my story.
Jill sat there taking in what I was telling her without saying a word until I finished my story.
As the last words left my lips, Jill sat back in the couch, with a smile on her face, followed by her releasing a little giggle.
“Tom, can I see it?
I’ve never seen one, and I think it’s so cool that you are in such a relationship.
To tell you the truth, I have always had this fantasy of being used like someones slave/sex toy.
Just hearing you tell me this story has my panties wet.”
Jill spent the next few minutes begging me to show her my cage.
The more I demurred, the more insistent she became.
Until I became so frustrated that I stood up in front of her and dropped my shorts.
“Holly shit Tom, that’s so cool, may I touch it?”
Unable, or unwilling to speak, I just nodded my head.
Reaching out, Jill took my cage in her hands, while inspecting the fit, and weight.
While this was happening, my cock began to harden, and press against the confines the cage imposed.
Pulling away for the moment, Jill looked surprised at my reaction.
“Jill, it’s the cage, when you began touching me I began to get a hard-on, the cage prevents that from happening by imposing an amount of pain to remind you of it’s presence.”
Standing there, Jill reached down, and began to rub herself under her skirt.
Watching this wanton display of sexuality, caused my cock to begin to expand again.
Forcing my eyes away, and my thought to think of anything other than sex, my cock began to settle down.
“Tom, I have a huge favor to ask you, will you introduce me to your Mistress?
I know that I’m asking a lot, especially on such short notice.
The truth is, I’ve hidden my kinky desires for so long, I don’t want to miss the opportunity to explore them with someone I trust.”
“Jill, I don’t know if she will meet with you.
That being said, all I can do is ask her.
I need to call her tonight, so I should know by tomorrow her decision.
She has us going to a party on Saturday, and I need to make sure that the tuxedo I’m wearing is properly fitted.”
The next couple of days were incredibly busy with my classes.
I did speak to Mistress about Jill’s request.
I was told to give Jill Mistresses phone number, and speak no more to Jill until I was allowed to.
The next afternoon, there was a knock on my door, opening the door, I was surprised to see Miss Lisa standing there with a garment bag in hand.
Bidding her entrance, Miss Lisa hung the garment bag on a coat hook by the door.
“Thomas, please undress so we may conclude the fitting.”
Standing naked in my living room with Miss Lisa fussing about in the bag, along with a couple of other bags she had brought, one of which had a beautiful pair of dress shoes.
Unzipping the garment bag, Miss Lisa first removed a pair of basic white boxers.
Placing my hand on her shoulder for support, she knelt down and slid first my right leg followed by the left into my new boxers.
Next came the starched white shirt, followed by the pants.
Shirt buttoned up, pants pulled up, she produced a pair of suspenders from the bag, and adjusted them to fit properly.
Strapping on the cummerbund, she reminded me that the proper way to wear this was with the pleats in the up position.
As a reminder she told me they were nicknamed “Crumb catchers” in order that you can remember it’s correct way to wear them.
Stepping over to the full length mirror attached to the back of the door, I was stunned at the transformation.
Hello, my name is “Bond James Bond”.
Fuck, I looked good, dressed in this classic English style tuxedo, I looked like a gentleman of royal decent.
Source: reddit.com/r/Erotica/comments/x7fnaj/mf_the_wager_part_5_chastity_bdsm_18