Before I tell my story, let me tell you a few things about myself first. I've always been the sort of guy who preferred to "wear the pants" in a relationship. I'm not a bossy jerk or anything like that, I just tended to be drawn to more pliant girls for much of my life. In my days as a High School basketball star, things came easily in that regard.
After so many years went by, though, things started to change. I grew up a bit, and I started to tire of the more demure women I was accustomed to. I began to crave more willful women, yet my "alpha dog" persona remained. It was a terrible dilemma. Perhaps all I really needed was a girl who I could hold a decent conversation with. Well, whatever the case, I made a series of decisions that lead me to my new life.
I don't remember how exactly I found out about chastity, and chastity devices. I guess it was a gradual discovery. However it happened, the idea fascinated me. Initially it was female chastity that I was drawn to, but I soon lost interest. A few years ago, I would have been all over that concept, but not anymore. I didn't need to trap a girl in a chastity belt to take charge in a relationship, anyway.
Chastity still held my attention, though. So I continued my research, and began to garner some interest in male chastity. At first the idea was lost on me. I kept reading stories of subservient men being trapped in chastity belts and tormented by cruel, vindictive women. For a guy like me, I figured that whole concept was the last thing I'd want to be a part of.
But soon, a thought occurred to me. I could get a device for myself, then the next girl I dated, and once I got to know her better, I would relinquish the key to her. It might be kind of fun to give that sort of power to a girl who was so unaccustomed to such authority.
It really seemed the perfect solution to my problem. A demure girlfriend, but with a bit of control over me that could be really fun and sexy. She would be my girl, but have this one thing that she could hold over me. I could have my cake and eat it too. After a bit more research, I discovered a male chastity device that seemed perfect for me. I ordered it and waited for my life to change.
The next day I was at work, perusing chastity subjects online. I was trying to learn a few more things, see if I could come up with some games to play with my key holder once I met her and things got started. I had to quickly close down my browser, however, when one of my co-workers walked by.
Sexy, sexy Christina. The tall, slender brunette who I could never resist taking a moment to gaze at whenever she passed by had appeared. With a confident stride, she strutted past my desk, dressed in black high heels, a pleated skirt, and a tight gray sweater. The whole outfit showed off her ample physique, and she wore her usual sly, fox-like expression that made her almost irresistible. Almost. See, I had asked her out once, but as luck would have it, Christina just happened to be one those more strong-willed types I just wasn't into. It was really quite a shame, since she was one of the hottest girls I had ever known. Life's full of little misfortunes, isn't it?
A few more days passed, and my new chastity device finally arrived. I hastily unpackaged it and took a look at my new toy. It was amazing. At first it seemed a bit complicated, but after following the instructions, I managed to figure the thing out. Now it was time to see what this thing could do. I retreated to my bedroom, and after making sure the windows were closed so no one could see me, I removed all my clothes. Then I began to find the right fit for the device.
I sat naked in my room, trying on the various parts on myself, seeing which setting felt best. The main parts fit over my cock and balls, encasing them securely. Once I got the right fit, I took the small padlock that was provided with the device and put it in place, holding the whole thing together. The lock rested atop the sheath that concealed my penis. My heart began to pound as I clicked the lock shut.
A rush of excitement came over me as I tested the device's security. I made a few attempts to pry the thing off, but it wouldn't budge. As long as the lock was in its place, there was no escaping. From there, I then made the next most important test: Trying to touch myself while wearing the device. It didn't take long to discover that was impossible. My balls enclosed behind a secure shield, while my cock was completely sealed within a solid sheath, forcing it in a downward angle. I ran my hand along my imprisoned parts, trying to get any kind of contact with them, but the device thwarted my every attempt. After so many tries at getting off, I started to get really horny. The whole concept turned out to be even kinkier than I had expected. Just the fact that I couldn't get any pleasure to myself made me want it even more.
I tried everything. I tried using my hands, I tried grinding against some pillows on my bed, but it was no use. As long as this device was fastened to my body, sexual satisfaction was impossible. Whether through sex or masturbation, relief was not to be had. I couldn't have wished for better. After wearing my new device for some time, my longing for an orgasm became impossible to ignore. Taking the only key to the lock I released myself. Once free, I quickly masturbated myself to a powerful orgasm. After being confined withing the chastity device, I was amazed at how good it felt to get myself off, even after only a few minutes. If it was this good after such a short time and while I still held my own key, I couldn't imagine how incredible it would be once I met a worthy key holder.
Over the next few days, I took the time to get more accustomed to the device. I would wear it for varying periods of time, see how long I could put up with it. It was difficult, as I would get really horny pretty quickly. It was a perfectly comfortable device, so there were no problems there, and it remained totally unnoticeable beneath my clothing. I even wore it out in public a few times and had no problems. In fact, it was during one of those times that I met Bree.
Boy, was she something. I saw her in the video store, where I usually like to hang out after work on Fridays. She was browsing near one of the sections of the store that I frequented often. Bree was one of the prettiest girls I had ever seen. She was a petite blond, with a pretty round face and large blue eyes, giving her an almost angelic appearance. She had a perfectly proportioned body, which her becoming outfit showed off nicely. Naturally, I started talking to her, and we really hit it off. As I chatted with her, I was rather taken by her wit and personality, yet she also seemed to possess that shy demeanor that I found so appealing. Could she be the one I was looking for? It sure seemed like it.
During my encounter with Bree, I was given a rather stark reminder of the device that I was wearing. Bree was a beautiful girl, and just looking at her was enough to get me fired up. I could feel my cock straining against its prison, nearly causing me to wince. I maintained my composure, though, and soon I had set a date with the sexy Bree for tomorrow night. As soon as I returned home, my first instinct was to remove my chastity device and get some relief. After being locked up for so long, then hitting it off with such a beautiful girl, I was incredibly horny.
But then I realized, I should try to keep myself encased until my night with Bree. That would make my eventual release all the more satisfying, for both of us. So, I resolved to stay in chastity until my date with Bree. If things went well, and she and I continued to see each other, I figured it would only be a matter of time before I could present her with my key, and the whole chastity concept I had discovered. I was sure she would like the idea. But, I had to make sure to take my time.
Sleeping with the device on was a little strange at first. Comfort wasn't an issue. I was just so horny that I could hardly keep my mind clear enough so that I could get to sleep. The next day, as I was getting ready for my date with Bree, I made extra sure that I had my key with me, in case things really took off. I picked up Bree from her place, and took her to one of my favorite restaurants in town. Once we were seated, we began chatting. As before, I was amazed at how well we got along. She really was one of the most charming girls I had ever met. The evening went on, and we had a terrific time together. We were about halfway through dessert, when Bree reached over and touched my hand. Our eyes met and she asked me if I would like to go back to her place for a while. Suddenly my chastity device felt very, very tight.
Back at Bree's place, we both headed toward her bedroom almost immediately. Trying to seem nonchalant about my situation, I excused myself to her bathroom so I could take a moment to prepare. Naturally I just needed a moment to unlock myself from my chastity device, as I couldn't let Bree know about it quite yet. After taking off all my clothes, I then went to remove my chastity device. Considering how turned on I was, I wasn't surprised at the slight struggle I had to go through to remove it. Afterward, I made sure to hide it in my pile of clothes well enough to make sure that Bree didn't happen upon it and discover my secret before it was time. After I finished everything I had to do, I returned to Bree's room, and found that my day in chastity was well worth it.
Bree lay naked on her bed, her gorgeous body on full display. Every part of her was perfect. Her legs, her stomach, her ample chest, she was just flawless. Climbing on top of her, I felt her breasts in my hands, causing her to moan with pleasure. My day of denial was coming to an end in the best way possible.
We made love all night and into the morning. Thanks to my day in chastity, I have to say I was in top form that night. I may have been a bit more intense than usual after being so horny for so long. The poor girl actually passed out briefly at one point. But I could tell she had a blast the whole time. I know I sure did.
Later in the day, after our marathon of love, Bree and I took to the shower together. Naturally that lead to another bout of lovemaking. After that, I had to take some special care upon dressing myself. I had to be cautious she didn't see my chastity device as I reattached it. I had a close call at one point, but I managed to keep my secret. I hastily threw the rest of my clothing back on, and had a small breakfast with her.
So after all this, Bree and I parted ways for the day, making plans to see each other again soon. I remember the tremendous feeling of satisfaction I felt after my night with Bree, which I largely credited to the use of my chastity device. I was eager to see her again and grow even closer to her, so I could sooner present her with my key. If it was this cool while I had control of the key, I couldn't wait to see what Bree could come up with.
As the week went on, I was in and out of my device for varying periods. It was kind of tough to keep it on for long periods now that I had Bree on my mind so much. I could probably have an easier time with it once I gave her the key, but at this stage, I found it hard to trust myself. I decided I had to find a way to discipline myself. That week, I resolved to leave my key in my desk drawer at work overnight, and that way I'd have to wear the device, whether I liked it or not. It was a Wednesday night that I made myself endure this, and boy was it tough. I tossed and turned all night, not sure I could get a decent night's sleep so I could get up in the morning.
I made it to work on time the following day, and I was horny as hell. I snatched my key from my desk, and hid myself in one of the stalls in the men's room. I plucked the device off hastily, and masturbated to another strong orgasm. My head finally clear, I reattached the device and went back to work. I started to question my chastity idea. It was obviously incredibly difficult for me to stay in this thing for long periods of time. How would Bree approach all this? Would I really be able to put up with her calling the shots to this sort of thing?
Eventually Friday came, and I went to work with my device on. My lingering doubts had been circling my mind for the past few days, keeping me a bit unfocused. That was probably what lead to the issue I had. Around lunchtime, I felt a sharp pain in my crotch. I realized I must have put my device on incorrectly in the morning, because it felt as if one of my balls was being crushed. I nearly yelled out loud when it first hit me, it was that painful. I kept quiet as best I could, and hurried to the men's room to fix myself. I was in such pain, I guess that was why I made my first real mistake.
I didn't bother retreating to the privacy of one of the stalls, instead standing out in the open, my pants down and the malfunctioning device in plain view. I unlocked the device, finally relieving the terrible pain stabbing into me. I sighed with relief, rubbing my parts for a moment and soothing the pain that had beset me. After that, I set to reattaching my device. Not a moment after I clicked the lock shut, I heard a dull thud from behind me. I spun around, realizing that the noise I heard was the men's room door closing. My heart skipped a beat. There was no one there, nor had there been anyone in the room with me at the beginning. Had someone been watching me the whole time? Had they seen standing there, wearing my device? Who could it have been?
Now my mind was really racing. I returned to my desk, expecting someone to approach me about my device, but it never happened. Dropping my key into my desk drawer, I tried to remain calm about the close call I just had. The possibility that one of my coworkers caught a glimpse of me in a chastity device had me pretty freaked. How embarrassing would that be? I spent all day dwelling on it, which is probably why I made my next big mistake.
At the end of the day, no sooner had I returned home when I realized that I left my key at work! There was no chance I could just go back and get it, it was too late in the day. The place was locked down as much as I was. On top of that, it was a Friday, so I was going to to be stuck for the entire weekend. After struggling with just one night, I couldn't imagine how hard this was going to be. What a nightmare.
Sure enough, my weekend was a living hell. I was horny day and night, and couldn't get the slightest relief from it. Two long, long days of this torment was more than I could bear. I was actually starting to regret every buying this thing. I tried to stay positive, maybe see it as more training to the inevitable role of chaste male with a female key holder, but it was not easy. A key holder was one thing, but having the key simply hidden away where I couldn't access it all because of myself was not quite the kind of fun I was looking for.
After what seemed like ages, the weekend finally came to an end. I never thought I'd be so glad for it to be Monday. I rushed to my workplace, and hurried to the office and my desk. I was so horny I could hardly see straight. That was probably why I couldn't believe what I saw once I got to my desk. I don't know when it happened, and I probably never will, but sometime between when I left work last Friday and when I arrived that morning, someone jostled my desk drawer open! In a daze, I quickly dove into my desk and began sifting through my things, hoping intensely that the worst hadn't happened.
Everything else was in its place. A few flash drives, some papers, various sundry items, even the wad of cash I kept there all remained. But not my key. My worst fear had come to life. I searched frantically for it, in my desk, under it, all around my work station, but it was nowhere to be found. Now I was really trapped. I wave of anger and panic rushed over me as I finally gave up my search and slumped in my chair. What a disaster. Resigned to my fate, I tried to go about my work as best I could, but the combination of my head full of thoughts on how to get myself out of this mess, how and what could have happened to my key, and the sheer horniness I was struggling to endure made the day unbearable.
Naturally I theorized that the culprit must have been who may have spied on me in the men's room last week. Why else would anyone just take a small key from my desk and leave everything else? But even at that I had no solid clues. Well, whoever that was, the ball was in their court. All I could do was wait for them to make their move. Until then, I was struck in my own personal hell.
I considered simply breaking the lock to get out, but then I'd have to pay for a new one to replace it. As it turned out, they were almost as expensive as the device itself. I really didn't feel like shelling out so much money all over again. I emailed the place I had ordered it from, to see if there could be a replacement key sent to me, but that was no good. Each lock was custom made. It was impossible to replace. What the hell was I going to do now? I suffered all day and night, both at work and at home. And poor Bree, I kept having to avoid her all week, because there was no way I could pleasure her stuck like this.
After a week of misery and frustration, Friday came again, but the thief never revealed themselves. After work, I found myself at the video store again. Maybe renting the right movie would help get my mind off my situation. Naturally every single movie that I saw seemed to have some sexy subtext to it. It was maddening. I was in such a daze after my week of unwanted celibacy, that was probably why I hadn't realized it when someone approached me.
"Hey Tony!" a familiar voice said in a cheerful tone. I jumped slightly and turned. It was Christina. I blinked with mild surprise, and my cock twanged in its prison at the sight of her. The device was becoming a bigger problem than ever before.
"Christina, hey," I said somewhat flatly, trying not to give any hint of the distress I was in. I'm not sure if it was the fact that I had been stuck in a chastity device for over a week or not, but for some reason, Christina looked sexier than ever to me.
She stood before me, wearing a tight pink t-shirt that clung to her torso, showing off her assets and leaving a small sliver of her midriff bare. Her tight bootcut jeans were low around her hips, and had tattered holes worn in the knees. Her feet were clad in thin white flip-flops. She looked fantastic. Smiling at me in an unusually chipper manner that I have never seen her in, she hooked her thumbs on the front-most belt loops of her pants. She moved her feet a little wider than shoulder width apart, and bobbed up on tip-toe for a second as she spoke.
"So I was thinking, remember when you asked me out? Well, I actually think that might be pretty fun. How about tonight?"
I couldn't believe it. Of all the times for this gorgeous girl to approach me, why did it have to be now? My cock struggled and strained as I tried to remain calm. I swore in my head as I stammered an excuse.
"Oh, geez, y'know tonight isn't so good. I have... stuff to do." I felt like the most colossal idiot in the world. No one in their right mind would have turned her down, but here I was doing just that. I wasn't sure if that was worse, or the fact that Christina kept pressing.
"Oh don't give me that," she said with a giggle. Using her thumbs she pushed her jeans down ever so slightly, giving me a glimpse of the very top of her panties. By now my cock was practically screaming and I was almost at the end of my rope. Again I tried to turn her down, but she wasn't having it.
"No, Christina, I really can't."
She ran a hand through her hair as she replied, "C'mon, I really want to."
"Look, I swear I'd love to at any other time, but now is really not good for me."
"Well I think it is."
Oh God, why was she doing this? The hand she ran through her hair moved down to her stomach. She rubbed it for a moment, lifting her shirt slightly and giving me a brief glimpse of her sexy midriff. I turned away from her for a moment, trying to hide my grimacing as my encased member continued raging. I cursed my bad luck as I tried to muster another weak excuse. "Listen, if it were any other time, I would. Honest. But it's just-" I went silent mid-sentence and froze once my eyes turned back to her.
She drew her hand down lower, guiding my gaze to her crotch. Dangling from the pull tab of her fly on a small ring was my key. Christina stroked it with a finger slowly, then gave it a few playful tugs.
"Yeah. You know what that is," she said. The sunny tone to her voice was gone. I looked back up to her face, and saw that her usual sly grin had returned. I remained motionless and she slowly stepped closer to me. She ran her fingers along the collar of my shirt, her smile broadening. "You can pick me up at seven." With that, she twirled away from me, giving me a gloating smirk over her shoulder as she did so, then strutted away, the snap-snap-snap of her sandals fading as she went.
I stood there, stunned at my new situation. So the thief had revealed herself, and she was one of the hottest girls I had ever known. She was also the commanding type of woman I wasn't interested in, but now she had me. My mind raced. It was only a few hours to seven. What should I do? What could I do?