By boyryan54

I pull off his rubber isolation hood, looking into his watery and bloodshot eyes. His eyes are pleading with me, and I can barely hear the muffled begging coming from his tightly tape gagged mouth. But I will not sway. He knows what the deal was, and how much I compromised to take him on.

Back when we met seven years ago, he was so cocky and full of himself, 25 years old and convinced the world was at his feet. He was constantly playing with other “doms” and tops, getting very pushy and getting his way when it came to play. After all, he viewed it as an honor for others to enjoy his body. Things changed a bit when he met me. He knew I was different and wouldn’t cater to him. In fact, I never approached the topic of play with him. I knew that if I withheld my passion for the bdsm lifestyle from him, it would drive him crazy. In his eyes, no man would ever refuse him.

He knew I was not one for random play. I was always very clear about what type of submissive that I play with: objects. And I was always clear about what I wanted long term. My hand and mind would give me more pleasure than a random one-night stand. We would meet regularly, grab a drink, dinner, and talk about life, or the lifestyle, and some of his unfulfilling sessions. He would fidget a bit when I would explain why he would sometimes find them unfulfilling; he wasn’t experiencing the type of submission he secretly desired. Occasionally I would entertain him, going into detail about what I would do to my subs. At times, his hand would travel down to his crotch to adjust himself while I discussed a flogging scene with a past slave or tattoo ideas for a future slave. It was fun watching his squirm.

Little did he know I was setting a trap. I knew what I saw in him, while he was in denial. He was going be my slave and he was going to come willingly, he just didn’t know it yet. After a few months, I learned how to play him like a fiddle. Luckily we had some common interests in bondage and gear that I used to my advantage. Occasionally he would get distracted by a quick fling or dom who might give him a slight taste of deeper submission and go quiet, but all I would have to do is send a photo I knew he would like and he would come back. He viewed me as a prize to claim but in time, it would be I that would claim him. Eventually he started reaching out very regularly. Sending me photos of himself in various gear, trying to get more of my attention and perhaps even my approval.

He took the bait sooner than I expected. During one of our coffee hangouts, he expressed some disappointment that I had gone silent for a weekend. I explained that I had gone out of town to a fellow Master’s home and we had enjoyed that Master’s slave. I could tell from his expression there was a pang of jealously but his hormones and desires took over. “What happened, Sir?” he asked. I figured I would tease him and I knew the truth would blow his mind. I explained during that weekend we had pushed the slave. Heavy flogging, piss training, heavy use. As it was the anniversary of its collaring, guests came over to celebrate. After a long night of boot worship and ash service, the slave received a tattoo and a PA. I enjoyed watching him squirm in his seat as I went into detail about how the slave was stored away at night, how the slave was fed his meals from bowls on the floor, how we would keep him in a box while we toasted the slave’s many years of service. At the end of my recap of the weekend, I made a passing comment, but one that would prove too much for the hungry thing seated across from me: “it was nice to have a sub in bondage at my boots again.”

“I could be that sub, Sir!” He exclaimed.

Bingo. Hooked. He was mine. But now to make him work for it.

I feigned interest. Questioned his motivation and tried blaming it on his horniness. Tried to explain to him that it wasn’t a sincere comment, that he wasn’t truly interested in such a deep level of commitment and submission. The more I pushed away his comment, the more insistent he became. I decided to leave him wanting more, and made up an excuse to leave the coffee shop quickly just as he was so desperate to get his way.

Oh the texts that followed were beautiful. Part horny sub fantasizing, part sub truly wanting that reality. He would do anything. And he went into detail. Explained how perfect of a slave he would be. Things he would do to please me. Ways he envisioned being stored away. Constant begging to sub to me. While the texts were focused on him and what he wanted, I was so turned on because I knew my plan worked and what lay in store for us both. In fact, I still have the texts he sent me after that conversation; screen shots of them still play on repeat on a tv in the playroom, displayed like trophies. I like to keep those on a slideshow in the basement playroom, and sometimes I will read them to him while he sucks on my dick after a heavy flogging. I use them to remind him two things: how badly he wanted to be my slave when things get rough for him, and to remind him of how selfish he once was.

After those messages, I decided to “give in,” as he would think of it. We arranged for some quick sessions: sleepsack storage, other times a quick flogging and edging, or a boot worship and oral service of me, etc. Sessions mostly focused on what he wanted to experience. Over the course of a few months, our play got a bit heavier. I took a bit more control over him outside of our scenes. Sometimes I would lock him up in chastity for a week or so and enjoy how much more he would take after being denied. Slowly I would start to expose him to play I wanted in addition to play he wanted at the moment. But I always knew how focusing on his pleasure would slowly erode his free will. As I pushed the element of chastity heavier and heavier in our play, I noticed a bit more resistance from him that I had not anticipated. While he loves being stimulated and kept excited, he was still so motivated by the reward of an orgasm. This had to be stopped. But I was unsure how to do it. I didn’t want to scare him away. So I kept gently pushing the topic.

We settled into a routine, but one I was uneasy about. Sure he was reaching and breaking new limits. He could start to handle periods of time in gear or stored away (under supervision). He could even begin to take a good flogging. At the end of the day, he was getting his needs met, but I wasn’t sure how to take the next step. He would even broach the topic of being a slave to me, about how he wants to be property, be marked, pierced, etc., but he could never imagine being locked away in chastity forever. At this point, he knew I had invested a lot of time and energy into him and I wouldn’t just walk away. I didn’t like how this power dynamic had switched.

It wasn’t until after a year had passed since we started playing that I found a way. His cockiness around chastity and denial. He had demonstrated to me many times how long he could hold off from a cock orgasm while edging himself, and he would always warn me while I was edging him. He would brag about how he didn’t need chastity. We had even gone a few months with him not releasing without my permission. Hell, he even liked going that long as he felt so much more submissive and started to enjoy focusing on me. But at the end of day, he knew he would get off at some point; that if he did a good enough of a job, I would let him cum. But again, I knew I had to be patient. I knew how addictive chastity and denial can be and how it warps the mind. I knew in time he would get more and more submissive and ask for a contract. And then what I knew my patience would pay off, and that’s when I would make my move. And with my plan back in action, I continued our little power play game.

After another year, he was pretty well trained during our longer sessions. Could swallow my piss without spilling a drop. Spent hours nursing on my dick under the desk while I worked. My boots were fairly well polished, and my home spotless. He had done a good job working out after his work and staying toned for the rubber suit he so often wore fit nicely. He had even impressed my fellow dominant friends with how much cigar ash he could swallow without complaint. Then one night, after I released him from a long night in a rubber hog sack, he asked about making it official and signing a contract, for life. He had a taste, but wanted something more. He was craving more. He needed more. He had thought about it for a long time and really wanted it. He thought he understood what he would be giving up. But I reminded him about what that meant chastity and orgasm wise. “Are you really willing to give up ever having a cock orgasm again?” I asked him knowing his answer.

Then our dance started. His cockiness came back. He didn’t understand why he would have to give them up. Can’t I understand? Why can’t I compromise. Blah blah blah. This is what I was waiting for. I knew if I stuck to my plan, I would win. That was the last time we played for a bit. I knew I would have to withhold what he wanted so badly for him to cave.

After a week, he came back and ask, “how about 100? I will sign if I will be allowed 100 orgasms in the future”. I said no.

A few days later: 80 orgasms. I said no.

A few weeks later: 50 orgasms. Again I said no.

A few days after that: begging to be tied up in rubber, and “please 40 orgasms. For the rest of his life”. So I said, “ten cock orgasms”. He said no.

A week later: he showed up at my door in the rain, hammering on the door. Begging to be let in to sleep in the cage. I opened and just said “ten orgasms.” He looked at me with pleading eyes, then shook his head no. I closed the door in his face.

Then a month went by. I was strong but I was worried I went too far and that his desire for orgasms were too strong. I knew in no way was I to reach out to him. A few times I doubted my plan would work. I admit my home felt empty without his visits. Then on a quiet Friday night, I was reading while enjoying a cigar, trying to distract myself my a gnawing feeling in my gut that I had lost, a knock on my door.

I opened it, and there he was kneeling. Head down. I was pleased to see he had cut and styled his hair in a Mohawk, a style he knew I liked on others.  My dick twitched in my pants. God I missed him.

“Ten?” I asked sternly.

“Yes Sir. Ten orgasms, please Sir.”

Bingo. It worked.

I took him inside. I pulled up a contract on my iPad. One night, when I was feeling low and felt I overplayed my hand, I wrote the contract to distract myself. Almost envisioned it like a vision board, willing it to manifest itself and become true. Though I left the chastity portion blank. I wasn’t sure how to write that portion at the time. But now I did.

“The slave is given ten cock orgasms, which he must choose wisely. Please note that cock stimulated releases, either intended or unintended, will count toward the 10. Slave may choose to be unlocked to be edged or edge himself, but once the tenth orgasm is achieved, permanent chastity will be enforced. In time, the slave might achieve the ability to cum anally, which will be allowed. If the slave is observed trying to stimulate the cage after the tenth orgasm, measures will be taken to ensure no possibility of cage stimulation. Please note some of these measures might be drastic and extreme to ensure compliance.”

He signed without really looking. I locked a chain on his neck. We kissed. I stripped him, had him take care of my boots, and then put him away in his cage. There would be plenty of time to celebrate later, and even more once he moved in to be property full time.

The slave was quick to blow through his first two orgasms. Since he didn’t read the contract when he signed, when he did a thorough reading while locked in a cage a few weeks later, he begged to be unlocked and jerked off. An hour later, he begged again to reread the contract and jerked off again.

Number three was when he was suspended upside down in full rubber. He had asked to be unlocked and edged, and then he asked for electro bands on his dick. I was happy to apply them and decided a gas mask with rebreather bag would be a nice addition. He came hands free with the electro while begging for air. I am not sure if this counts as an intended or unintended orgasm, but doesn’t matter in the long run. Seven left.

Number four, five, and six were about six months after number three. A friend had shown up with a Venus milking machine. The slave had exceeded my expectations and didn’t beg for an unlocking once. My friend was staying with us for the weekend and I wanted to hurry this process along. On the last day of his visit, we stripped the slave of his gear and suspended him standing in a tight “X” position. We then took turns lightly flogging, touching, caressing his naked body. Little hot wax here and there. Light ball flogging. Slowly getting the slave more and more worked up from the slight stimulation. After a little more than an hour, he was begging into the gag, which when I unlocked, he was begging for the milker. He needed release and he didn’t care how many, and please if we could have mercy. If only he knew what would be store once the chastity is permanent, but we were happy to cater to his wishes.

Number seven was about five months after the milker. The slave had gone a long time being unlocked and edging. I had thought he would have had an accident by then. The slave and I were enjoying a quiet night. Earlier that day, we had just gotten his nipples pierced and a slave tattoo added to the back of his neck, as well my initials surround by a chain and padlock on his pec. The slave was just a puddle of mush and just needed some Master time. The slave had surprised me in asking for something fairly vanilla: he wanted to be jacked off and have an orgasm while being fucked in the sling. While on paper it seems simple, gazing upon his fresh piercings and marks of my ownership, all while his eyes taking in the glory of his Master, the raw connection of total ownership basking over us both while I took us both or orgasm was one of the more memorable moments of our time together. This one was a special release for us both.

Number eight came about from the slave’s ego. While at a leather bar, a friend of mine was making comments about how much weight his slave balls could handle. I politely acknowledged my friends bragging, knowing very well at this point my slave could handle a lot more than his inexperienced slave. But my playing along seemed to bruise the ego of my slave and he rudely spoke out of turn that he could handle more. Before I could shut my slave up, my friend suggested a contest to prove it, winning slave fucks the loser. Word spread through the bar rather quickly, the slaves were tied to the racks, boots tied to their balls, and then pool balls loaded into the boots. The other slave caved at a pathetic weight. My slave realized the empty victory, but the other patrons were expecting a show. What choice did my slave have? He had to deliver and took the other slave on the pool table. My slave tried being smart, tried to fake an orgasm, and as he was pulling out, my friend slapped my slave hard on the ass with his gloved hand, making my slave jump and thrust back into the loser slave, pushing my slave over the brink to actual orgasm. The look of shock and horror on my slave’s face will live on in my memories forever.

Number nine was a surprise to me. I had to leave town for work for a week, and had a kinky friend stay with the slave. My friend had an interest in long term storage and asked me if he could use this time to push my slave. One day, my friend messaged and asked if I was somewhere private and could I facetime. I said sure, and he showed me my laying bondage box I had built for my slave. He opened the lid, and there was the slave locked away, strapped to the bottom. I noticed a number of electro wires running over the slave’s rubbered body, bands on the slave’s cock and balls, and an internal catheter running into the slave. My friend closed the lid and explained the slave had been there for a full thirty-six hours, having been fully prepped prior, fed liquids, and piss being removed. The slave had headphones going, and would I like to take control for a bit? Next thing I know, I open a link, a night view camera shows my slave in the box squirming, and another link that controls the electro. Upon hearing my voice, the slave gets excited at having some human contact; and I start playing with the electro. After an hour or so, the slave is sobbing through the gag and I have just jacked off twice while playing. I decide to take advantage of my broken down slave and change the electro settings to a pleasure setting I know he can’t resist. As I creep up the power, I watch the slave shake his head no. Higher and higher I go, very slowly, one power level a minute. After 30 more mins, and another orgasm by myself, my slave’s head start nodding yes. I push the power higher and higher, while the slave starts moaning and nodding yes. Not long after I see the slave tremble, a muffled long drawn out yell is heard and I watch the slave’s dick twitches wildly as number nine is pulled out of his balls.

Which brings us to this evening. Number ten. I almost feel a little bad for my slave, but then again, I have finally won. I have gotten my way. Moving forward, I will have a fully chaste object. I know once the lock pins of the internal lock are damaged, that will flip a switch in his mind. And I can’t wait. But the poor slave. Such a sad last cock orgasm. Even I am not sadistic enough to have wished such a pathetic ruined last orgasm on a slave. I look down at the poor slave. Body so shiny, sealed away in that amazing tight black latex sleepsack. Can almost see a little cum oozing through the crotch zipper. I look at my slave’s watery and bloodshot eyes, his muffled pleas falling on deaf ears. The poor slave has been so good the past year. Staying away from anything that could cause an accident. Rarely asking to be unlocked. He had a moment of weakness today and asked to be edged while strapped in the sleepsack. Who would have guessed he would have made it through the whole hour edging, only to have an accidentally release caused by the vibration of the crotch zipper being closed over his cock? Or maybe it was the sensation of the latex tightening over it? Or maybe both? Doesn’t matter. Think I will leave him to stew in his mess overnight while I go to bed. Start tomorrow off by sealing away his cock forever, and enjoy his defeated mind tapping into the level of submission I know he craves, one where his own pleasure is finding pleasure though serving me. I can’t help but smile though, while I look into my slave’s pleading eyes as I say goodnight. I tell myself my smile is to reassure him it will be okay, but deep down I know I am smiling because I won.