My Boyfriend's Chastity Ultimatum

I'm not much of a writer, but ive read literotica stories for years and thought I would submit this little vignette I wrote years ago. I hope some of you find it inspiring!

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"Happy birthday, baby," I told the boy. He turned 26 today, and it was our third birthday together. We met via a Craigslist post I made called "Dom looking for eager sub," and a one-time thing turned into a regular thing, and as the sex kept getting hotter, we discovered that we were connecting on multiple levels. He has been living with me for over two years now. He is the sweetest boy I've known, and also one of the most submissive.

On his birthdays, I usually give him free rein to do what he wants. Today he woke me up by sliding his wet hole down on my morning hardon, and riding me gently until I shot a load in him, and he jacked a load on my chest (and my chin a bit) as soon as I shot in him. Then he slid off me and licked his cum off me, and then took my cock in his mouth and nursed me for a good half hour until I was back at full mast and shot another load down his throat. After that, we cleaned up and got dressed and went out for a 10 mile hike through a forest that he'd loved since he was a kid, and then I took him to a nice dinner at his favorite sushi restaurant.

When we got back home, we each took a shower. "Baby, would you mind cleaning up your pubes today? It would turn me on so much," I asked. He always kept his pubes more of less shaved, but he had about a week's worth of stubble down there at the moment.

"Of course!" he said, and gave me a quick peck before bounding to the bathroom. He took about 20 minutes in there, and then came back out naked. His beautiful lithe body was totally smooth from the ears down. "Your turn!" I went into the steamy bathroom and took a quick hot rinse. When I came back, he was lying naked in bed, and then he grabbed his legs and pulled them back towards his head when he saw me. "Will you pound me hard tonight?" he asked.

"Of course, baby" I replied, and then I dove down and began licking and eating his sweet pussy. When he was totally relaxed and beginning to quiver, I slid my cock in and he threw his legs up over my shoulders. I loved pounding him in all kinds of positions, but I knew that this one was his favorite. I went straight for his P-spot, and he jacked himself off within a few minutes, us both knowing that he would still want more. I didn't slow down, and after about 10 more minutes, I pushed in to the hilt and filled him with cum again. After that, I kept stirring my cock in his guts while he jacked furiously, and then he blew another load all over himself, although this one was smaller and watery.

"I love you so much," he murmured, as his body relaxed completely under me.

"I love you too, baby," I said. "Now let me go get your present."

"Aw, you didn't have to do that! You're enough for me," he said, close to tears of joy after his birthday fucking. He really was the cutest boy.

"Be right back," I said, jumping off him and toweling myself off. I hopped over to the linen closet in the hallway and pulled out the small black box I had hidden there. I brought it back to him in bed and he gasped when he saw it.

"Oh my god..." he murmured, his eyes showing a mix of eagerness and shock.

I handed it to him. "I want you to be the one to open it."

He looked at me with a look I'd never seen before, and he came close to hyperventilating. He pulled off the lid and looked inside. "Oh.... my GOD!" he yelped. Inside was the custom metal chastity device I had had made for him at Mr. S.

"Happy birthday, baby. I know that you have been fantasizing about this for a long time now. It's time to make it real." His eyes grew huge. "Fantasizing" was definitely the right word for the situation. I knew from the sites he visited that he thought it was a hot idea to have his cock controlled like that in theory, but I knew he also had no intent of actually asking for it because of all of the practical aspects of it. (Let alone the fact that he loved to cum, of course. And whenever he looked at chastity porn... he always shot a huge load after. Hah.)

"Let's go ahead and get this on," I said. His cock was plumping up noticeably, but because he had just shot a couple of loads in the last few minutes, he didn't immediately get hard. I pulled out the cage and quickly pulled his balls through it and slipped his cock into the cage before he got any harder. I reached into the bottom of the cage and pulled out the custom padlock I had had made for him, a gold-plated heart shape engraved with "12-27-16," today's date, his 26th birthday. I slipped it on the device and locked it.

"Jonathan..." he said, with the wavering in his voice that he got when he started to get anxious. "I really don't think..."

"Shhh baby," I interjected. "Just relax. It's going to be OK, I promise. I know that you've been wanting this, and it's time.

"And don't worry," I continued. "It's not going to be that hard for you, I promise. Uh, no pun intended, actually. But I'm going to unlock you for an hour a week, every week, no tricks or surprises, I promise. Monday from 7PM to 8PM. I'll make sure I'm always home then. First you'll need to clean up, mostly just shave yourself clean again and anything else you think you need to do. And then for the rest of the hour, you can do absolutely anything you want. I'll fuck you if you want, and you can blast however you want. Who knows, you may even shoot off hands-free after being locked for a week and then having a raging hardon while getting fucked. Or you can just watch porn and jack out a few loads. Absolutely whatever you want."

"OK..." he said, tentatively. "Maybe... that might be OK. We can try it, I guess."

"We're definitely trying it, baby," I replied, injecting an authoritarian edge in my voice for the first time today. "There's a little bit of a condition, but it shouldn't be too bad, and I think you'll enjoy it. You just have to blow one other guy and swallow his load. And just get him to take a pic or two of you doing it and send it to me. You just need to get his dick in the frame and show his cum in your mouth."

"OK...." he said, with a bit more trepidation. "That doesn't sound too bad, I guess." He didn't really like getting filmed or having pics taken, but he was open to it if I really wanted it. He was quite a bright boy actually, and already had a promising professional career as a junior consultant at a business process optimization firm. He trusted me but he always made it clear that he didn't want pics of him "out there," as he said.

"Just show me that, and the hour is all yours. And then next week, two cocks. And so on."

"Wait... what do you mean, 'and so on?'" he said, suddenly looking vaguely alarmed.

"One more cock each week," I replied, calmly. "Three the week after that, then four the next week. And so on."

"Wait..." he said.

"You'll still get your hour out of the cage either way. But if you don't meet your goal, I'll be there watching you in the shower while you clean yourself up, and you're not going to touch your cock with anything besides the razor. You get 5 minutes for that. And then the rest of the time, your hands will be cuffed over towel rack, and I'm going to beat your cock with the riding crop for the rest of the hour. If you somehow manage to cum from that, that's fine, but I know you've never been much of a pain pig. Although who knows what a week of denial will do to you."

"I mean... are you saying that I'm going to have to start sucking like 30 or 40 cocks a week or whatever to get that hour to cum??" he asked frantically.

"Yeah," I replied, coolly. "But it shouldn't really be that hard. I mean, think about the first few months. You'll probably meet some guys who want it a couple or even like 3 or 4 times a week. And then if you do a good job--which I know you will--you'll start getting guys who want to come back for more week after week, so you shouldn't have to spend too much time looking for new cock. So like on week 12, let's say you have two guys that want to blow in your mouth two times each. And then you have like 5 or 6 other guys who come back from other times you've blown them. So then you only need to find like 2 or 3 new cocks to suck that week. That shouldn't be hard at all."

"I mean... I guess that sounds possible or whatever... but what about... later?"

"Well, I know it will start being a challenge at some point, but there's still plenty of flexibility. It's not like you have to suck 10 cocks a day or something. Like imagine a year from now. You still have seven days in the week to do this. If you spend a few hours at a the big glory hole downtown on Saturday and Sunday, you can probably knock out a good 20 cocks just like that. And then a few more at home or out and about the rest of the weekend, and then it's only a few cocks a day during the week. Not that bad."

"Umm... that's going to be basically impossible to keep up with forever. Like... this is going to get insane."

"I know there will probably be a few weeks here and there that you miss the goal, but that will just motivate you to try harder the following week. I have faith in you." He looked pale. "And after all, this is still voluntary."

"Wait, what? Voluntary?" he asked, looking utterly confused at this point.

"Yeah," I replied coolly. "You can stop anytime you want. Just let me know and I'll hand over the key to you. Then after that, I'll give you 72 hours to move out, and you never contact me again. And if you do contact me again, all of those pics you sent me start getting uploaded to Tumblr, one pic a day. Until they're all up."

"Daddy..." he said meekly, defeatedly. He burst into tears.

"Shhh..." I stroked his hair gently. "You know that this is going to be good for you. You know that it's time. I still love you and I'm going to love you more than over."

He curled up in my arms and sobbed harder and harder. "Daddy... I love you so much... I can't... I can't leave you. I can't lose you!" I stroked his hair tenderly while he cried. Eventually the sobs turned to sniffles as I comforted him.

"I know you're going to make me proud boy. This is our next step, and I'm going to love you more than ever."

He sniffled and hugged me tighter than ever. "Daddy... I just love you so much... O... OK."

"Good boy," I said, as I continued to stroke his hair. I knew it was going to be hard on him, both the chastity itself and the increasing challenge of getting his free hour, but the idea of controlling his cock and orgasms turned me on so much that I didn't care. He would have 52 weeks like this, and then his day of birthday freedom again. After that I had some ideas for modifications I was going to make in his weekly regimen. It would give him some more options for meeting his weekly freedom target, but he would have to work harder for it. And it would definitely make his blackmail hole even deeper. One thing was for sure--it was going to be hot as hell for me no matter what.