My Keyholder

We exchanged glances, I was wearing a harness and jeans and my black boots. At the time my hair was buzzed, clean shaven, my chest shaved. He smiled as he walked over to me. My heart raced. “What you drinking?” He asked. I asked for a Corona and he picked up the tab. He said he’d never seen me in there before, he would have noticed.

We struck up a great conversation before he leaned in to kiss me. His coarse goatee scraping against my smooth face made me feel like I was kissing a real man’s man. I swooned and lusted. We made our way to the back room after getting to know one another.

We continued snogging, and he reached into my jeans and realizing I was wearing a jock, he fished to finger my hole. I pushed down it, it’s thickness feeling wonderful inside as we continued making out. I opened up his vest to feel the curly hairs on his chest, and went down to chew on his nipples, his left one pierced with a barbell. I flicked at it with my tongue.

I reached down to feel his bulge, and I was pleased with that I felt. It was rather thick, straining against his boxers, I reached in and discovered I could barely fit my fist around it. It was probably a good 8”, cut. His cock throbbed in my fingers as his one finger in my chute became two. Mmmm that felt so good. We moved over to a dark corner, and I unzipped his fly, releasing his thick cock from his boxers, got down on my knees, and began to suck on him. He placed his hand on my head, feeling me move my mouth over his shaft, getting it all wet and shiny. I was moaning as I sucked him, a sign of the utter bliss I experienced feeling that throbbing thickness full on my mouth.

Jace pulled me up from the floor, and kissed me again. His lips overpowering mine, showing me his dominance to which I willingly succumbed. He reached for my zipper, pulled it down, spun me around, and his dick hard and wet in my crack as he rubbed it up and down. He whispered in my ear, “I want to fuck you sexy”, and I said, “yeah?”, and he said “oh yeah, I want that ass”, and I bent over slightly as he drooled saliva down on his dick, rubbing it to coat his massive hardon. The thickness of his cock head pushed open my sphincter, it burned, but I knew I was going to enjoy it in due time.

Jace reached into his jeans and fished out a small bottle of poppers and pushed it under my nose. He said “inhale baby”, and I did. And then the rest of his inches pushed through, and I let out a cooing moan. “Oh yes”, I felt so full of dick. Jace’s dick.

In the dark back room, we were lost amongst other guys getting it on. Cries of ecstasy and sounds of ducking around us, we mixed in without notice. Jace began to enjoy fucking my ass as I bent over holding my knees as he held onto my hips and piston fucked his load into me.

After loading me up, we went back to the bar and had another round of drinks before he invited me to his place for the night. I went willingly. We got naked and went to bed, Jace fucking me on my side as he held onto me, we swapped tongues, and he filled my ass with another burst of his cum. My face was burning from the scratchiness of his course goatee, but it felt good, it felt nice. Jace cuddled me in his strong arms as we drifted off to sleep.

Over the years, Jace and I stayed fuck buds, never anything more. I discovered he enjoyed exploring his dominant tendencies and I enjoyed exploring my sub side with him. Eventually, our dom/sub conversations brought him to ask me if I’d consider chastity, and if I’d let him be the key holder. The idea turned me on immensely. I had grown to trust Jace very much, and knew I could to explore this new road we’d be traveling.

After our next hookup, we went online to find a good chastity lock to start with. It was plastic, and contained a small padlock.  I bought it, and we shipped it to his address. A few days later when it arrived, Jace texted me to come for drinks after work. We did drink, but we also fucked, and I got off hard as Jace railed into me while on my back. After emptying his load, he began to chuckle. I asked him what was  so funny, and he said, “I’m glad you got off because you won’t be for awhile”.

I smiled, and excitedly asked, “is it here? Can I see it?”, and he said, in due time, let’s go finish our wine. So naked, we both walked into the living room and sat on the sofa, and finished our wine. I think I drank mine fast, I was so excited like a school boy.

Jace said, “before we put it on, we’ve got some housekeeping to do. Come with me”. And I followed him to the bathroom, where he shaved off my pubes and cleaned off my balls, I was completely smooth, and my wet balls were hanging nicely under my 7”. Jace walked out of the bathroom, and brought back a small box. He sat on the closed toilet seat, as I stood up. He applied some lotion to my balls and dick. Then he secured the ring around my balls, and shoved my slick cock into the plastic sheath, pushing down until it all clicked in place, and applied the padlock. He showed me the key and said, “I’ll be keeping this”.

My cock began to throb in its new covering, I was so excited. Then it hit me, I couldn’t get hard, and it ached. Jace knew by then that my nips are hot wired to my cock, and he began torturing me, tweaking them, pulling on them, biting down on them. I did enjoy the attention, but it was killing my cock. Jace laughed and kissed me. He said, “that looks so hot on you. Very hot”. And he licked his lips.

It was getting late for a weeknight as we both had work in the morning. He stood up and said, “we should probably cal it a night then, yeah?”, and I agreed. Getting dressed was interesting. Tucking the cage into my briefs kept it all in place, but when I pulled on my tight jeans, there was an insane bulge. I was worried how it would look going to work like that in the morning? I asked Jace when he’d unlock me, and he again laughed and said, “you just have it on for a few minutes, and you’re worried about when it’s coming off? Let me worry about that”. He was always good for never answering a question directly.

I left and walked home. Feeling the cage in my jeans while walking was something I’d have to get used to. I went home and stripped down to my briefs and tried to fall asleep. The throbbing of my cock made it almost impossible. I’d been jacking myself off nightly for 20 years, it seemed impossible not to cum before falling asleep. It was a fitful night, and I was barely functional the next day.

Jace texted me every day a few times a day to check on me. I thought I was going to lose my mind. It was a Friday night and I went to the gay bar. Jace wasn’t around that weekend, I was flying solo. Long story short, that was the night I learned that by getting other guys off, I threw the attention off of my own dick. I became a more attentive and focused cocksucker, and a better bottom.

Three weeks after my first chastity experience, Jace invited me over. Over beer, he asked me questions about what I had been feeling, what it had been like, did I have any regrets, etc. he admitted to me that having that power, that control over me, even when not in his presence, gave him a sense of confidence, like his male hormones went into overdrive knowing that I was struggling and he was the cause. He eventually released me, and we agreed that in 3 days (it was Tuesday, we’d meet again Friday), I would be locked up again, this time for 4-weeks.

It was about a year into this when one night I had returned from the bar, had been fucked, and I was going insane. In my state of frustration, I pulled on the lock, just wanting the chance to relieve myself. I needed to cum so badly. The pressure I applied on the lock broke the plastic, and just like that, I was free! I stroked myself to wild orgasm, but felt extremely ashamed and guilty afterwards. This was not sanctioned activity.

In the morning, I confessed what had happened to Jace. He wasn’t pleased, and said that I had violated his trust, and that I was a two-bit whore who couldn’t follow rules. He was rightfully upset. About a week later, I was invited back to his place for drinks, and we sat and talked, and from under the sofa, Jace had a shit-eating grin and jiggled a box. He asked, “you know what this is?”, I said, “no Sir”, (he liked that when I called him Sir sometimes). He said, “it what bad boys deserve when they can’t behave”. I looked at him intently. He opened the box, and a shiny metal cocktail cage emerged.

He said, “we’re gonna trim you down and then we’re gonna lock you up”. No getting out this time”. And that’s exactly what we did. And here we are about 6 years removed from our initial meeting at the bar, about 4 years into chastity, and Jace still gets off on holding the key, and I love that he has it. I’ve also learned how to bring myself off without touching myself. Can’t do it often, but when it happens, it’s spectacular!  Now you know a little bit about how I needed up in chastity, and a little bit more about the man who put me in it.