Yeah Sure I'll Do It!

"Yeah, sure, I'll do it! I can take on a challenge," Is what I said when my friend Jack challenged me to Locktober. I had never heard of it before, but the idea sounded simple. Jack said he was doing it, so I figured I could do it, too. I didn't mind a new kind of challenge, and there were rumors that cum retention helped build muscle, or something like that, which is what I was trying to do. I didn't really understand it, but it couldn't hurt to try. Oh, I'm Alex, sorry, I forgot to tell you. I'm 27 and I'm a high school English teacher. I'm 5'11 with sandy brown hair. In my spare time I like to play video games and work out. I like to play on teams at my community center. Oh, and, I'm gay. But, not everyone knows that.

Anyway, Jack told me to meet at his friend Ethan's house that evening to get fitted for the chastity cage I would wear for the month. Jack was a bit shorter than me with cute blond hair. He works as a gymnastics instructor so he has a very fit build. We were roommates in college. He's gay, too. We both found out about each other by catfishing each other one time. That meetup was probably the most embarrassing moment of my life, but we've been best friends ever since (and, no, we've never dated. I don't think I would anymore, I love him in a special brotherly way! Seriously!!).

Ethan was someone we recently met while at a bar one night. Ethan was a performer, a drag performer even. I know they have another job, but I forgot what it is. They're about the same height as me, with dark brown hair and they are very outgoing, always making everyone around them laugh.

The two of them laid out quite a spread of cages. There were different sizes, different shapes, some were metal, and some were plastic. "

All right, drop your drawers." Ethan said.

I blushed. I'm demisexual as well, and I actually haven't lost my virginity so I still get shy in front of others. Don't tell the others! They don't know, I don't think.

"Why are you blushing like a virgin? Think I haven't seen a dick before?" they said.

"Knock it off! You're gonna scare him!" Jack interrupted.

"Oh...uh, ok. I kinda thought maybe I could do it alone?" I said.

"Hahahaha! No way, can't trust you. Come on, I've got a show tonight, we can't take forever!" I shyly dropped my draws and exposed my dick to both of them.

"Oh wow, I only have a few cages I think will be big enough for you, my friend. Didn't know you were hiding that from me!" Ethan said. Jack kicked him.

"OK ok! Fine! Here, let's try this one. It's pretty open so it's easy to clean," Ethan said, as they grabbed a long metal cage. Their hands were as cold as metal as they fumbled with my balls to get the ring on, and then came the cage. Suddenly realizing the predicament I was in my dick started to get hard.

"Oh no no no no no! I don't think so!" Ethan said right as he clicked the lock into place. "Did you really think you were gonna stop me at that point?"

"I....Didn't expect it! I said as my cock swelled up to fill the cage.

"How does it feel?" Jack asked

"Weird, and cold, and this ring around my balls is too tight I think, it hurts a bit." I replied.

"Hm, I don't have any other rings for that one, so I think we'll try another one. The cage is a bit shorter though, I think it will fit." Ethan said. "You're gonna have to work that out before I take the cage off."

"Huh?" I was confused.

"Your boner, dude, you have to get soft again before I'll take the cage off. You don't know what to do? I don't wear the cages, just put them on others. Jack, what do you do to get soft?"

"Well, playing video games or working out helps. Sometimes a cold shower works too." Jack said.

"That's it! Hop in a quick cold shower, that will help." Ethan told me. I didn't want to do it, but the boner was starting to hurt a bit in this cage. They took me to their bathroom and I stood in the shower and turned on the knob. It was like icicles driving into my skin. Within moments my dick started shrinking up, even smaller than it usually is due to the cold water.

"Alright, that's good," Ethan said after about 5 minutes of me standing in the water. "Let's make this swap." He unlocked the first cage and took it all off. Now his hands were a bit warm, it felt nice. I tried to ignore it so I wouldn't get hard again. I felt him put on another ring and suddenly applied a bit of lube which really started to wake up my soft cock that has been given so much attention tonight, but no action. I really started to feel teased. A moment later a lock was inserted and once again my cock was out of my control. This one was black and made out of plastic. Even though I wasn't fully hard my cock was busting out of it, it seemed.

"How is this one?" Ethan asked.

"This one feels better, yeah.

"Alright, glad to hear it!" He said as he stood up and put the keys on a necklace he was wearing with several other keys.

"Aren't you gonna take it off?" I asked.

"Alex, we have to test the cage out for a few days before we know if it will work for the full month. I was SHOCKED. I hadn't planned on being locked now, I hadn't rubbed one out all day and I was feeling really pent up.

"What the hell? I didn't know that was part of the deal! It's already September 27th! There's only a few days left until October starts!" I cried out.

"I'd say if you come back Friday night for us to check we should be good." Ethan said. Jack was chuckling in the corner. I looked at him desperately for help.

"Hey, Alex, I actually agree with them on this one. I have some experience with this and if the cage isn't comfortable it's going to be a hell of a month, and a month is a long time." Jack told me. I was stunned, and hornier than I could ever remember.

"Come one, we know it works. Just take it off for tonight, I'll put it on tomorrow morning to start trying, I promise I'll make it work." I begged.

"That cage doesn't belong to you, or the keys. I don't think you get to decide what happens with them." Ethan winked and laughed.

"Come on, let's go watch a movie. That should help calm you down a bit." Jack suggested. I was a little angry at the moment, I didn't realize in my anger that my cock had softened up a bit and I even forgot I was wearing the cage for a moment. Then I realized it again and my cock started to get hard again. I whined a bit, stomped my food, and then followed the other two into Ethan's living room to watch a movie.

I could definitely sense the cage being there as we were watching the movie. I absolutely didn't help that Ethan would periodically reach over and pat my crotch to remind me. I'd look at him and he'd have what I guessed were the keys to the cage I was wearing in between his teeth. God, they really do have a cute smile.

It was getting late, so Jack decided we should head out (he was my ride for the night). We said our goodbyes to Ethan, who gave my crotch another squeeze as a reminder of what happened.

"Good luck this week, see you on Friday!" they said.

On our drive back to my place, it wasn't very far, Jack began to give me some advice.

"You'll want to lube up the base ring pretty often. Tonight is going to be rough. Men get several boners throughout the night and your body isn't used to wearing the cage. Find some way to distract yourself, and when you wake up with a boner, get out of bed and take a piss. It will help. It really is best for you to start this early to get used to it."

"Will it hurt?" I asked

"Yes, but not in a bad way. More in an achy way." He replied. He dropped me off, he gave me another wish of good luck, and he was off. I stood outside and watched him pull away for a moment, just thinking about how much I enjoy spending time with him. I walked into my apartment and went to my room.

I took out what I was wearing so I could stand in front of my mirror to get a really good look at the situation I was in. It was kind of difficult to behold. My cock was thoroughly secured inside the cage. I pulled at it a bit. Very secure. I realized just then I needed to piss. I went to the bathroom and held my dick out and as I released piss went everywhere.

"What the fuck!?" I was so confused. I clenched up quickly and squatted down in a very undignified way sitting to pee. As I sat there I got curious about what happened. I took a closer look and realized the tip of my dick wasn't in line with the end of the cage. I wiped myself off, washed my hands, and sent a text to Jack.

"Wtf? I just pissed everywhere??? Wth is going on?" A minute later he replied:

"lol!!! Dude, that's hilarious. I'm sorry, I forgot to tell you, sometimes you have to readjust the tip of your dick so that it's in line with the tip of the cage. I like to get in there and push it around with some q tips." Qtips? I took some out of the cabinet and tried my best at what Jack told me to do. After a few minutes of poking around and getting myself aroused again, I figured out what he was telling me to do. With a little more effort I was able to get the end of my dick in line with the cage. Hopefully no more messes. I looked at the clock, it was 11:33. Holy shit! That's late! I have to get up for work tomorrow!. I quickly took care of my nightly routine and crawled into bed about 10 minutes later. I set my alarm for the morning and rolled over, trying not to think about what Jack had said in the car might happen tonight. I sighed, and said out loud.

"I can do this, I like a challenge. This is nothing so far." I closed my eyes and began to fall asleep.