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@BndgGabe
As of July 20th, I've been locked in chastity for 127 days. I can perform "tasks" to reduce my time, or or get permission to cum, but my cock won't see freedom until well after the COVID-19 lock down is over. I'm Gabe, and this is the story of how I got here.
-- Sunday, March 22nd, 2020 -- Day 0 -- I've been playing with Sir every Sunday for the last six weeks. It's not anything formal, I call him Sir, he calls me boy, and until today, it never extended beyond his apartment. Even before our first meeting, the sexual connection between us was instant and electric. We share a ton of common kinky interests, but most importantly, I love being used and servicing him, and he loves using me.
I was supposed to meet Sir today, but all that went out the window when NYC went into COVID quarantine earlier this week. Instead of meeting, Sir called me and we spent some time catching up on our week. Beyond the bedroom, we share a lot of other common interests too.
But eventually our conversation got into the fun dirty stuff we both like. He told me what he'd planned to do to me today, but because we couldn't meet, he had another idea. We had talked about chastity many times before, and he knew chastity is one of my turn ons. And since I wouldn't really be seeing or hooking up with anyone during the lockdown, laid out his plan.
Starting today, I would be locked in my Holy Trainer. It would remain locked on me for the full duration of the lock down, plus an equal number of days afterwards the lockdown was over. He called the extra days after the lockdown was over my bonus days. My cock was already hard, and I knew I wanted to do it.
"Sir, that sounds hot, though the longest I've ever been locked up is 1 week, I'm not sure I can last that long..."
He wasn't done describing his plan though. While I was locked, he'd assign a daily activity, and offer regular challenges I could use to shorten the bonus days. Each one would be worth time off my chastity sentence, but only AFTER the lockdown was over. If I agreed to his plan, being locked during the lockdown wasn't negotiable. My cock was already at attention, but the idea of having to perform tasks made me even hornier. He offered a few examples.
"For every hour wearing a butt plug, I'll take 20 minutes off your bonus time. For every hour wearing a gag, 10 minutes off your bonus time. You get the picture. I'll send you the list of regular challenges tomorrow. But for now, what do you think?"
I fucking loved it. I was scared as hell, like I said, my longest period was one week, but it's not like I had anything else going on. "Yes, Sir, I'm in, Sir." I didn't know if I could do it, but figured I'd have the key, so if I needed to get out, it would be easy enough. Little did I know.
"Good boy. We're going to switch to FaceTime for the rest of this call so I can see you getting ready and locking yourself up. You know what to do, call me back." He said, and ended the call.
It took me a minute to set my iPad up so that I could switch to FaceTime. I knew he'd want me to be naked, and kneeling when I got on with him. I laid out my play sheet on the ground, closed the blinds so my neighbours couldn't see me, set up my iPad, stripped off my clothes, settled down into a kneeling position, checked to make sure the camera was properly lined up, and then called him.
"Hello Sir, I'm here to serve you" I said when the call connected.
"Good boy, you've learned well. I'm glad to see you're naked and ready. This is the last time you'll truly be naked for some time. That cock of yours will be covered up soon enough." He said. "When was the last time you shot a load?" He asked.
"Three days ago, I had a friend over who throat-fucked me for 20 minutes, then fucked me." I replied. We didn't have a formal Sir/boy relationship, and I could play with anyone I wanted, or cum whenever I wanted, but he always thought it was hot hearing about me being used.
"Nice, well. Then. I figure you should get one last opportunity to cum before I lock you up. Go get your XL, and 2XL egg plug, your nipple clamps, ball gag, and some lube."
I got up and went into my bedroom to grab what he instructed, and came back. I laid everything out on the floor in front of me, knowing better than to put anything on or in, then said "I have what you requested, Sir."
"Good boy. Start with the ball gag, put it on, and I want it fairly tight. I want to see you drooling today. You know how I like a good drooling boy. After that, apply the nipple clamps, and assume the formal kneeling position." He said.
I knew that me not talking was part of his plan, and it was hot, I could only grunt in agreement. I put the ball gag in my mouth, and pulled it tight, not so tight it hurt, but tight enough that I couldn't push it out with my tongue. I grabbed one nipple clamp and started working it on to my left nipple. Pulling it out, pinching the nipple a bit and sliding the clamp on, then tightening it down. He didn't say how tight to go, and I wasn't sure how long we'd be like this, so I didn't go too tight. I then moved on to my right nipple and did the same thing.
I double checked the camera was still lined up, and assumed the formal kneeling position. Kneeling on my feet, knees spread apart with my balls hanging down, and my cock sticking straight up at attention. Fuck, I wanted to rub my cock. But I knew better. I put my hands behind my lower back, so my elbows were pointed out, looking almost like a military stance, but on my knees. Finally, I dropped my head down to look at the ground and grunted that I was ready.
"Good boy, but I bet those nipple clamps aren't tight enough. Tighten them each by 1 full turn." He said.
I grunted in acknowledgement, and started tightening the left clamp. I got about a half a turn before I started to moan. Getting a full turn was going to be difficult. I pushed the clamps closer together and moaned my way through the full turn on the left. The right clamp was the same. I could now really feel the clamps on my nipples, squeezing them, causing pain and pleasure at the same time. I put my hands back behind my back, and continued to look down.
"Nice job boy. I wish I could be there to stroke your cock and play with those clamps. You'd like that wouldn't you?" He asked, all I could do was moan and nod my head in return. "Next, I want the 2XL plug in your hole. Lie on your back and work it in. You can start with the XL plug if you want. Imagine it's me working the plug into your hole while you do that. I can't be there to do it for you, but I can do it for you virtually." He said.
I laid down on my back, and looked between my legs to see if the camera. I had to adjust it a little to make sure he could see my hole, then grabbed the lube and started working on my hole with my fingers. After a minute or so, I grabbed the XL egg plug and started working it in.
I slowly worked the XL plug in, going in ¼, then out, then â..." and out, and ½ and out, slowly fucking myself with the plug, stretching my hole, getting it ready. Sir was awesome, offering encouragement and telling me to go further. Once the XL plug was in, he had me work it in and out several times until it would just slip in and out.
"Almost time to go to the 2XL, boy. Before we do, I want you to put the XL plug in, then push it out - 10 times. Only use your hands for putting it back in. " He said.
Fuck - I love doing that, I love the feel on my prostate, and he knew it. During some of our play sessions he'd milk my prostate that way, in and out, and in and out. I put the plug in, put my hands behind my head, and then pushed the plug out.
"One. Again." He said.
And I did it again, pushed the plug in, put my hands behind my head, and then pushed it out, and again, and again, and again.
"Nine, almost done boy. Those lips are starting to look really nice and swollen. Very good. One more, it's time for the 2XL plug."
My hole was feeling used, but it felt AWESOME. I put the plug in once more, and put my hands behind my head and pushed it out once more.
"Ten, perfect, good boy. Now, put the 2XL plug in, go slowly, I don't want you to hurt yourself, then resume the formal kneeling position."
When I left his place last week, he sent me home with the 2XL plug in. It was a 45 minute train ride, plus a 15 minute walk on both sides, and damn, could I feel it when I got home. I took my time working the 2XL plug in, and finally got it in. It felt good, my hole was stretched open, and it felt full. Pushing on everything. I just wanted to bare down and push it out, but knew I couldn't.
I got back on my knees, put my hands behind my back, checked the camera was still positioned OK, and lowered my head into its proper submissive position.
"Good boy, stay like that for the next 5 minutes. I want to see that drool really start to run down your chin and on to your cock and floor. I want you to imagine my hand running across your body, caressing you, feeling you, inspecting every aspect of your body." He said.
"While we're in lockdown, your cock is mine. You are not permitted to cum without permission. Your hole is mine, it can be plugged whenever you want, but you must text me when you put your plug in, and when you take it out. Expect to spend at least an hour a day plugged, and likely more."
GRUNT. Loss of my cock, and plugged frequently. This was going to be fun. And maybe a little bit of a challenge?
"It's a good thing you're uncut, otherwise cleaning would be difficult. But you will still need to pay extra attention to cleaning. While you're locked up, you must sit down to piss. Only men with real cocks can stand while pissing. Is that clear?" He asked.
GRUNT. Fuck that was hot. Locked, plugged, and can't stand like a real man to piss? It's a good thing I wasn't going to work any time soon. At this point, the ball gag was doing its job, and I was starting to drool on myself.
"You look very hot boy, you've been hard this whole time, and now you're drooling on yourself. I'm really going to enjoy teasing you over the next few weeks. For your sake, I hope this lockdown doesn't last too long, but for my sake, I hope it goes on a long time!"
"But now it's time. Those clamps have been on about 45 minutes at this point, and have loosened up a bit. Tighten them down one full turn again, then go get a damp towel to clean yourself up, and your Holy Trainer. Lay the Holy Trainer out in front of you when you get back."
I did as asked, moaning like a little fucker as they applied more pressure to each of my nipples. I just pictured him doing it. I stood up, walked to the bedroom, and brought my Holy Trainer out and laid it out for him to see. I have the 40mm ring, and the nano cage. It fits me really well, I'm more a grower than a shower, so I don't need anything big, until I do. But hey.
"Good boy. Tighten the nipple clamps another ¼ turn, then you have 3 minutes to jerk off. If you don't finish in 3 minutes, you don't get to cum. Once you've shot your load, wipe it on your ball gag, and clean your cock up with the wet towel."
Between the plug in my ass, the nipple clamps on my nipples, the ball gag in my mouth, and Sir gently encouraging me to shoot my load for him, it didn't take me long to cum. Up and down, and up and down, on my cock. After about a minute and a half, I shot. It was near a full body orgasm, and it felt great.
"Good boy, once you've cleaned off your cock, lube up the inside of the cage, then slip your cock and balls through the ring. It's time to start your lock up."
I followed his directions and wiped my cock snot off my softening cock, and into my mouth, then used the towel to wipe up my cock. I was spent.
Fuck. Right. Oof. I grabbed the ring and got my balls through, but my cock was still a bit too hard to fit through.
I think he saw the trouble I was having, because he said "OK, take a break for a moment, I want you to slowly take the clamps off your nipples. Think of how I do it to you boy, slowly unscrew the clamp, then once it's off, push your thumb into it, imagine it's me who's standing there taking them off you. For now, the gag and plug stays in though."
I knew this was going to hurt, but the longer I left it on, eep. I slowly unscrewed the left clamp and tried to apply pressure as quickly as I could, but DAMN if I didn't let out a little scream. I held the left nipple down for about 30 seconds before feeling started to come back, and I could start on the right one. Again, another little scream popped out.
"Good boy, I know those are tender, and they'll be tender tomorrow, but just think of me when you feel them tomorrow." He said. "Let's try to get your cock through now."
This time my cock slipped through the ring without too much trouble.
"Time to put the cage on, and lock it away. Say goodbye to your cock boy!" He said.
I grabbed the cage, and slipped my cock in, lined up the locking mechanism, put the lock in and locked the cage on.
"Good boy, keep the gag in and the plug in, we're going to go over some rules now. Grunt once to acknowledge each item, got it boy?"
Grunt.
"Every morning, you'll send me a message with a photo of your locked cock."
Grunt
"I will reply with a task for the day, and how much time it will shorten your bonus time. If you don't complete the task by 9pm that evening, it will add one full day to your bonus days."
Grunt. Shit, so I could shorten my time, or if I fail, add more time?!
"Every task requires photo or video evidence. You're a good boy, and I trust you, but I still want to see, and since I can't use you, I'll use you as porn." He said.
Grunt.
"Good boy, you can remove the plug,then, you can take off the ball gag."
My hole was exhausted and stretched! I slowly started gently pulling on the plug, working it out of my hole. It felt good to have it out, but my hole felt empty after. I put the plug aside and unbuckled the ball gag, sucking the saliva off of it as I pulled it out of my mouth.
"Thank you Sir, that was hot, and it feels awesome to have my cock locked up now!" I said.
"How does your hole feel boy? I loved seeing it stretched open with that huge plug!" He asked.
"Thank you Sir, it feels exhausted, but kind of empty actually Sir. It's hungry."
"Awe, poor boy needs something in his hole does he? Well, then put the XL plug back in, let's keep it plugged for the rest of the day."
"Yes, Sir!" I responded enthusiastically, as I easily slipped the XL plug into my hungry hole.
"Are you ready for your first task boy?" He asked.
"Fuck yah, Sir!"
"Now, for your first task. As I understand it, the USPS is still operating, when we get off this call, you will put ONE key in an envelope and mail it to me. Once I get it, you'll do the same for the other key. When I get the first key, I will put it in a combination lock box I have, and send it back to you. That way, you have the key in an emergency, but otherwise, I hold the key."
"What? Oh fuck, that's brilliant Sir. Even if the USPS loses one, or it takes forever, there's a good way to do this. Damn!" I replied.
"It's 2pm now, go clean yourself up, put the key in an envelope and send it to me. You can take the plug out whenever you want, but you must text me when you do."
"Yes, Sir." I replied.
"I will expect a text from you tomorrow morning, and will send you your second task. I will also send a longer set of rules and expectations to you tonight. Talk to you tomorrow boy." And with that he ended the call.
Fuck. I was spent, locked up and still horny as fuck. While I still had both keys, I knew if I didn't follow his instructions, there'd be trouble next time I saw him, and I didn't want to cause that. I decided I'd better clean up and do as instructed.
After cleaning up, it was time to send him the key. I pulled out an envelope, put his name and address on it, then put one key into the envelope. Just as I was about to seal the envelope, I decided fuck it, and put both keys in. It might take a few extra days, but the USPS would get my keys to him. I sealed the envelope, went down to the mail room in the lobby of my building, and dropped the keys and envelope into the outgoing mail. It was done.
It wasn't until I got back upstairs to my apartment that reality had sunk in. My cock was locked up for an indeterminate amount of time. Hopefully this lockdown won't last too long!
-- To be continued --
Got ideas for tasks Gabe should be made to do? Send them to recyclerboy@gmail.com or @bndggabe on Twitter