CHAPTER ONE: BEGINNINGS
How had all of this happened? How did I get here? And who even was I anymore. I guess to figure that all out, we need to start at the beginning.
My name was Jameson, but all my friends and family called me Jay. I'm currently 31 years old. Nothing special in appearance, I had short-ish brown hair, blue-green eyes, and just a little more padding than I liked, that some might call a Dad-bod. I was the usual, average guy. I played video games, I liked music, was decent at sports, and liked to hike and explore the outdoors. My friends and I would often have house parties, game nights, and go camping when things got too hot in the lower parts of Arizona where I lived.
I also had my private life. I identified as gay, and my friends all knew and supported this, and found fun in browsing online sites and subreddits. This slowly led me down some interesting rabbit holes. It started with BDSM porn and pictures. Pictures of strong men tying up other men and using them. Hoods, gags, harnesses, all of it. It was the gateway drug. Eventually, this led me to my next obsession, and the one that would eventually lead to where I am today: Chastity.
In the scenes where I would see men locked in these devices, I would always stare and dream about that being me locked up. Something about giving away that power made me excited. This led to me purchasing my first cage. Though the first one was a bit too ambitious in size. I'm not packing much down there, even before all of this. At the height of it all, I was roughly 5 inches hard, and half that soft. This was never a concern for me, because I always identified with being a bottom when it came to anal and oral sex. However, the first cage I bought, with little research, turned out to be much too big. And made me look even smaller.
A few year of purchase, and I had finally accepted and found the cage sizes for me. Small cages, and metal ones, were the ones that fit best, and kept everything locked in place nicely. Now while chastity was a big hit for me, I still lacked the willpower to keep it on for too long. Over the years of playing with it, I would on average keep it on for 5 days or so before I got so horny that I needed to take it off and jerk off. This is where it all changed.
Chastity porn and pictures eventually led me to what's called Sissy porn, or Femboi porn, or trans porn. Any of those variations really. The captions and pictures of men, locked in chastity, wearing stockings, garters, and corsets. Some were dressed as maids, others in lingerie, some even in large frilly dresses. My obsession grew as did my want for more chastity time. I found videos and pictures of sissies mastubating with a dildo and cumming with just their ass in what was called a sissygasm'. It turned me on so much that I wanted to try getting there. I eventually found myself on sissy exclusive sites, watching hypno' videos and trainers. I was hooked. But I was also scared to try any of it. All the sex i had up to this point was simply gay sex. Grindr hookups and what not, and while that was fun and I enjoyed it, I had yet to explore my kinky side outside my bedroom.
This is when I started looking around for `personals'. I wanted some online fun. Maybe if I start with something online it will encourage me to move into something in person. I began posting ads on sites like Reddit and Fetlife and stuff. Most of which were the same: Looking for Master/Dom/Keyholder.
I would write how I was interested in sissy stuff, and chastity, and being `owned'. This led to some of my first encounters online and eventually to some sissy purchases. Stockings, lingerie, nail polish, and various panties and thongs mostly.
While these online masters were fun, and some even used sites to help hold my keys to my chastity, claiming they would keep me locked for months, years, or even forever, I always found a way out of it when I reached my limit. I would cheat, and keep a key to myself, or write down the combination code to the lockbox. I always seemed to find a way. Part of me always sabotaged the arrangement. Then, after I was out and jerked off, the kink was on the back burner for the next few months and I carried on with my life.
That was until I met Master Liam. I was in a horny mood, I had seen some chastity pictures and decided to throw it back on the small metal cage that had become my go to. It was the perfect size where there wasn't room to grow or shrink, so it was always perfectly filled in the cage. As usual by this point, I posted online that I was looking for a Master/Keyholder, and by this point I was even posting pictures of my cage and myself, from the neck down at least, in stockings and lingerie. I was also posting the city and state I was in, but still looking for online mostly'. I got a few usual dick pics, which I didn't mind as they were usually big and nice to look at, and a few Mistress' responses, which never interested me because I was 100% gay.
Then his message came through:
Good Evening Sissy,
I saw your post online and checked out some of your past
pictures. You seem cute and I'm interested in getting to know
you more. I'm what you can call a trainer of sissies. I teach
them to please cock in every way, condition their minds, and even
help with purchasing clothes and makeup.
I'm in town this weekend and would love to meet you for a drink
and see if you have what it takes to be one of my sissies. Let me
know.
Sincerly,
Master Liam.
Now it wasn't anything above or beyond what I had received in the past, but it did make me really think. He wanted to meet me right away. It was Thursday, so in the next day or two at least. And he wanted to see if I `had what it takes' to be his sissy. Normally, I might just ignore it, or tell him I don't do it in person, just online, but I was locked and horny, so I played with the idea. He was in town this weekend, so it was almost like it was meant to be. But he didn't live here likely so this training would be online anyways, with a chance at real dick if he came into town regularly.
In the heat of the moment, I responded:
Hello Master Liam,
I don't normally do sissy things in person, and I don't dress
outside my bedroom as I don't feel I'm passable or anything.
However, I would be open to meeting for drinks this weekend to
meet you and get to know what type of trainer you are. If we have
a connection, I would love to have an online master who can come
and use me on occasion.
Jay
It wasn't moments later I got a short response:
Okay Jay, meet me at this address (He posted an address) on
Saturday at 6pm. Make sure you keep that cage on until then and
wear what you think is your cutest pair of panties.
Was I really gonna do this? I thought for a moment, but then once again, as my dick twitched in my cage, I let me horniess take over. Why the hell not?
I'll see you there. :)
This was happening. And worst case scenario, I could always ghost him and not show up if I wanted. I looked up the address and saw it was a house, though I was expecting a hotel or restaurant or coffee shop. I wondered if he was a snow bird or something that had two homes. If that was the case, he was probably some old guy and this whole thing wouldn't work out. Some guys were into older men, but it wasn't my thing. I started thinking of every possibility now. Who was this guy, what would he look like, what did he want with me in person?
I let myself wonder for the rest of the day and on Friday, then finally Saturday came around. Keeping the cage on continuent to fuel my drive to see this through, even though I was tempted and almost removed it the night before and jerked off. That would have ended it all right there. But I made it through and now I was showering and getting ready. I was gonna wear a simple graphic tee and slim jean shorts, but I had to pick which panties I thought were my cutest. I had a couple plain cotton women's Calvin Klein ones, a few basic solid color thongs, and then a set of lacy thongs too. When it came to cute, the lace was always my go to. I grabbed a pink lace thong and pulled it over my cage, leaving the nice little cage and balls bulge.
I pulled on my shorts and shirt, and walked out the door and to my car. I left one key at home on my nightstand, but tucked the other in my pocket in case he wanted me to take it off or something. I had no clue what was in store for me. I was shocked I was even going through with this.
The house was about a forty minute drive from mine, and as I pulled into the neighborhood I realized how nice all the houses were. This was the rich part of town for sure, not what I expected, but if he was a snowbird or something, that made sense as usually only the middle-upper classes could afford that anyways. Maybe he would be my sugar daddy?
I pulled into the long driveway of the house, which was on a hill overlooking most of the other houses around it, and turned my car off. The lights were on inside. My heart began to race. I could just turn around and drive away right now. I could just chicken out and carry on with my online existence if I wanted, and for a moment, I almost did. But then there was a ding on my phone, and another message from Master Liam.
The door is open. Come on in, sissy.
He knew I was here. I mean, I should have guessed. He probably has cameras outside and saw me pull up. Everyone has cameras these days. With a deep breath, I stepped out and walked up to the large double doors. This was a multi-million dollar house no doubt. I was about to knock, but then I remember he told me to just come in, so I grabbed the handle and walked into the house.
The house was massive. But luckily the man waiting for me was in the large great room right inside the door. He was nothing like I was expecting. For one, he was younger. Maybe mid to late thirties. He had black hair, he was taller than me, an inch or two over six feet opposed to my 5 foot 9, and he was in good shape from what I could tell. Better than I was.
He stood next to the table, where a tray with a bottle of whiskey and a glass sat. A second glass was in his hand and he was already sipping at it.
"Come in and have a seat." He gestured to the table.
I walked to the table and sat in the chair next to him as he poured me a glass.
"I'm glad you decided to come," he handed me the glass, "I hope you followed my instructions?"
I nodded, "I did."
"Let me see?" He sat down at the head of the table, watching me with a smirk.
I stood up. There was no backing out now, and he was good looking and I wanted him to fuck me. I pulled my shorts down just enough and showed the panties with the clear outline of the cage underneath.
"Good girl," He smiled. Hearing a man call me a girl was strange in person. I had only heard it online up until this point, "Take off your shorts and shirt and put them on the table."
I hesitated for a second, but then pulled them down all the way and folded my short, setting them on the table, then my shirt, which made me a bit more self conscious. I was a bit more chubby than I liked, and didn't have a six pack or major muscle definition.
"Good Girl, now have a seat and we can talk," he smiled as I sat, taking a drink as I did. I needed a little liquid courage. "So we both know why you're here. You are a sissy who needs to be trained and used, yes? You need someone to keep your clit locked and teach you how to serve and please, yes?"
I nodded
"Good," he smiled then took another sip, "Well I'm liking what I'm seeing. You have a soft body, which is cute on a sissy girl, and you know how to follow basic directions. And you obviously wanted this because you showed up here tonight in cute panties and a chastity cage."
I nodded again. I was too shocked and nervous to do much more.
"So here is my one time offer," he said, downing the rest of his drink, "I will train you. I will use you. I will pay for clothes and makeup and any upgrades and toys. I will help you be the sissy you were meant to be. I will let you suck my cock, take my cock in your pussy, and let you serve me as my personal property. I will hold your keys completely. All you have to do is accept my offer. I won't force it on you. However, once you accept, there is no backing out. I own you and you will do as I say, understood?"
I bit my lip, my dick straining in my cage. Own me... and there was no backing out. That was terrifying. But how would he enforce that? I could ghost when I've had too much. He didn't know where I lived, he didn't know my real name. And I had a key at home in case he took the other right now. I was horny enough to wanna say yes now, then I can figure it out later.
I nodded.
"So you accept this offer?" He reached in the breast pocket of his jacket that was draped around the chair to his right and pulled out an envelope and a pen, "If you accept, sign this."
"What is it?" I take the envelop from him and pull out a single folded paper that says `Contract' at the top.
"Just a sissy contract," he smiled, "I like making my sissies feel like they're owned because they signed away their lives on their own. That they made the choice to be owned and trained and used."
I looked down at the paper and began to read some of the lines. More of a skim than read. I saw him stand and unzip his pants, making me look up at him and away from the paper.
From his pants, he pulled out a large, semi hard dick. Larger than any I had taken before. It was glistening on the end with precum and made me instinctually lick my lips.
"You sign that, and this is yours to play with," he smiled, waving it in front of me.
I wanted his cock. The inner bottom slut in me needed that cock. And the locked dick between my legs was raging against the cage. And all that stood between me and his cock was a piece of paper, that wouldn't be legal in court anyways, so what was the harm. I picked up the pen without a moment of thinking, and signed my name and date.
"Good girl," he smiled, grabbing the paper and tucking it back in the envelope, then sealing it closed. He tucked his dick back into his pants and walked to the giant kitchen. I couldn't help but feel sad that his dick was gone. I wanted to suck it.
He walked back with two glasses of champagne, one in a normal glass, the other in a pink tinted one. He handed me the pink one and took the other for himself.
"A toast to your bright future," he raised his glass to mine and we clinked them, before we both downed the champagne... My head was spinning that this was all happening. I couldn't believe I was here, and he was excited to train me. I glanced at his crotch again as he stood in front of me, seeing the large bulge in his pants.
Then, my vision began to fade. All I could see was his crotch, then his legs, then his shoes... then... nothing.