Thanks for the feedback. There's a lot more to this story. Stay kinky, stay sane, stay safe out there! ---------------------------------------------------
I could hardly sleep. For at least an hour after I laid back down, I couldn't stop touching myself all over, enjoying the sensations of the large plug in my ass, my locked Holy Trainer, and the horny frustration that I couldn't jerk off. My balls felt like they were on fire - that was usually the point when I'd take off my device. In the middle of the night, I got up to check on the key in the freezer, but it was already encased in the block of ice. I moaned as my dick twitched, knowing I couldn't unlock for at least a little bit.
I retrieved my phone and sent Sir Scott a pic of the frozen key. I had only chatted with him an hour earlier, but I already felt such a strong sense of lust toward the leather-clad hunk. I wanted to please him. Maybe this was what I was missing in my life, having a sense of direction and someone to guide me?
Still full of energy, and my balls aching, I went to the bathroom, remembering a trick I read on the LockedMen chastity forum, that peeing would help relieve the pressure. I pulled my pants down and stood over the bowl, but looking down at my freshly shaved cock, I kept getting harder. I sat down and held my cage inside the toilet seat, feeling my dick pulse along with my humming prostate, with the Squarepeg plug still in my ass. I counted the tiles on the bathroom floor to distract myself, and eventually peed a bit, which helped relieve the pressure on my balls.
Somehow, I managed to get some sleep, and I awoke some hours later in the daylight. I reached for my phone, but I had forgotten to charge it, and it was already dead. I was eager to check back if Sir Scott had replied. Enjoying my horny frustration again, and proud that I made it through the night locked up, I put on my under armour leggings, a mesh shirt, a track jacket, a knit hit, and some sneakers, and went for a short jog, feeling full of horny energy.
Despite being January, it was a pleasant day out, so I enjoyed my short run through my neighborhood. I normally hated running due to the pressure on my knees and my balls slapping against each other, but the Holy Trainer acted a bit as a jockstrap. With my dick and balls held up tight next to my body and the plug still in my ass, I felt a rush of horny energy, glad that no one would be able to tell how horny I was.
By the time I got back to my house, I felt a very pleasant buzzing from my ass. I didn't want to take the plug out, but it had been quite a few hours by this point, so I took it out and cleaned myself in the shower. I lathered up my fingers with body wash and put my middle finger in my ass, enjoying how loose and perky it felt. It reminded me of my college days when I first discovered playing with my ass. I held my other hand against the shower wall for support. Soon, one finger became two, then two became three. As I finger fucked my ass, I imagined the leather-clad hunk who messaged me last night.
And then I got the familiar sense of doubt in my stomach, that it was too good to be true, that he was horny then and there and has probably already forgotten about me. Cursing at my pessimistic mind, I turned the shower off and dried myself. I decided that if Sir Scott had replied, I would stay locked, but if not, I would unlock. This was all good fun, but I couldn't go around staying horny all the time like some mindless himbo, could I?
I nervously opened up my phone, now halfway charged, and opened up Grindr. I was glad to see I had a few new visitors and a new message. To my disappointment, Sir Scott had not replied, but I did get a message from a cute Latino guy, Miguel, who said "I bet you look good in chastity. May I see?"
Part of me was deflated that my dream Sir hadn't replied, but this guy was cute too - his curly hair, brown eyes, light scruff, boyish charm, and bright smile made my ass twitch. I sent Miguel the same pics I took in the bathroom that I had sent Sir Scott. I enjoyed this feeling, sending my hairless body with a locked cock to a complete stranger. Still riding my wave of horniess, I lubed up my plug and moaned as my ass hungrily swallowed the toy.
My phone buzzed - it was a reply from Miguel. "Beautiful boy! Now show me your hole so I can decide if I want that too."
I stared at the last word for a moment, wondering what he meant. In my confusion, I texted back - "I have a plug in Sir. Do you want a pic of it in or out?" I fingered the plug, not wanting to take it back out yet.
"Take a video of it going in and out," Miguel replied.
I shuddered a bit in pleasure, enjoying taking the direction. I held out my phone and started recording as I lifted up my legs. With my other hand, I held onto the plug as I pushed it out, moaning in the process. I then pushed it in and out a few times, letting my hole pucker when it was empty. With one last push back in, I stopped recording and sat my legs down as I sent the video. Breathing heavily, I knew I was going to have to work out more if I wanted to do this sort of thing often!
In a moment, Miguel wrote back - "Good pig, Daddy likes."
I felt odd at what he wrote. I was never much of a "Daddy" guy, and I certainly never saw myself as a "pig", but both turned me on for some reason.
"Thank you Daddy," I wrote back, feeling slightly unsure about the wording.
"You don't have to call me that yet. I don't want you doing anything you're uncomfortable with. This is all virtual fun for now, but I'm not looking for chat and pics. My partner and I are looking for an eager sub to train. We're both tops, so you'll be staying in chastity as long as you're with us. Does that interest you?" wrote back Miguel.
I stared at the message and got a pit of excitement in my stomach. I went back to my messages with Sir Scott so I could look at his profile. Both Miguel and Sir Scott were the same distance away. I couldn't believe my luck, it was as if I was in some erotic fiction came true!
"Yes Sir, very much so! I'm just a hole for cock. I've been looking for someone to guide me and help me enjoy the pleasures of submission," I typed back eagerly. Part of me was worried I was too blunt, or said too much. My ass was twitching and my cock was throbbing, hoping beyond hope that these two beautiful Sirs wanted to take me under their wing.
"Good boy. We were hoping you would say that," wrote back Miguel. He then sent a series of pictures of him and Sir Scott, making out with each other, sucking each other's cocks, and one where Miguel was sitting around Sir Scott's shoulders. Each picture was more beautiful than the last, and I wanted so badly to jerk off at each of those pics.
Miguel then sent me a location via the app. "When you are ready, drop off your key at the mailbox at this address. I know Holy Trainers come with two keys. You can keep your frozen key for now."
I sat in my bed, even hornier than I was last night, thinking about how these men offered everything I ever wanted. I also worried that I could lose out on the opportunity of a lifetime. With a pit of excitement in my stomach, and my prostate humming with every breath, I wrote back: "Thank you, I will drop the spare key today. In a way, I've always been ready for this kind of situation. It seems too good to be true, and I am worried I'm going to be catfished. Can I at least meet you when I drop the key off?"
"Sure thing boy. We're not having guests in our houses yet. You will get tested for STDs and Covid as soon as possible, is that clear?" Miguel texted.
"Yes Sir!" I typed back right away.
"Have you had sex with anyone in the last two weeks?" Miguel asked.
"No Sir, not in two months," I admitted.
"Good boy. Then what are you waiting for? Give us your spare key before you decide to use it and jerk off that tiny worthless cock of yours."
The tone of Miguel's voice just from his words alone made me shudder in horniness. "Yes Sir!" I typed back.
I just had to find where my spare key was!