How I Wrecked My Hole

[pervinmt]

My palms were sweaty as I sat in my car. I had driven 8 hours to get there, but it wasn't too late to turn back. It wasn't too late to stop myself from doing something incredibly stupid and dangerous. 

 

It wasn't too late. 

 

But while my head was telling me the smart thing to do, my cock, that had been locked up for a month, and my ass, that had a plug up it, were telling me otherwise. Before common sense took over, I grabbed my bag and opened the car door.

 

I had met him two months ago, online. I say him, because I didn't even know his name. This was the first of several stupid decisions. But that was part of the fantasy, anonymity. Not only did I not know his name, but I didn't know what he looked like, how old he was, or anything a sane person would know about someone they were going to relinquish every ounce of control to. 

 

And that made my dick hard.

 

We had met in a fetish chatroom, and all I knew about him was his screen name, ControlingTop10. I had seen him in this room multiple times, but it wasn't until I said my darkest fantasy out loud that he sent me a message.

 

"Are you serious boy?"

 

I knew the game. Chat rooms are mostly there for people to jerk off. So I messaged him back.

 

"Yes Sir, I am."

 

"I can make it happen. How old?"

 

"35 Sir."

 

"Pics?" 

 

I sent him two pics. One of my torso, and one of my ass. I looked pretty good for 35. I wasn't a gym bunny, but I liked to run and bike, so my body was lean and tight. I had a nice lite covering of brown chest hair,  but my ass was nice and smooth.

 

"Looks good boy, Face?"

 

Now, I don't normally send out face pics, but I was feeling frisky, so I sent him one. I'm not bad to look at. I have nice brown eyes and a beard that I keep trimmed short and brown hair that I also keep short. 

 

"Very nice. I have to go but I will Message you soon."

 

And he was gone. I didn't think too much more about him, and didn't see him in the chat for a few days, so I figured he was a game player.

 

Then I got another message.

 

"You got a cam, boy?"

 

"Yes Sir."

 

"Turn it on and jerk off for me."

 

We got connected and I stripped off my clothes. I was already hard. I liked to show off for guys. I had a pretty 6 inch cock, not that big, but on my 5' 9" frame it looked just right. I jerked myself while he watched. At least I think he was watching, he didn't say a word. I liked that. It felt like he was using me. After I shot a healthy load all over my chest and stomach he finally messaged.

 

"Good boy. Be here same time next week, and wear a jockstrap."

 

"Yes Sir."

 

I thought about him all week, even though he was probably just someone getting his rocks off. But there I was, one week later in my jockstrap.

 

"Good boy. You poz?"

 

"No Sir, neg."

 

"Does it matter?"

 

"I won't have a choice, will I Sir?"

 

"No, you won't."

 

As he said those words, my hard cock throbbed and leaked precum.

 

"Good boy. So, are you still serious?"

 

"100% Sir."

 

"Good boy. If this happens, you will come down here on Friday, so I can make sure you're here, and real, and it will take place Saturday night, but you won't leave until Monday morning. Can you do that?"

 

"Yes Sir."

 

"Good boy. Once you get here, you will stay in a cage until it's time. And you will be hooded and blindfolded. Do you agree to that?"

 

I could very well be handing myself over to a murderer. But the danger of the unknown was part of the fantasy. 

 

"Yes Sir."

 

My hard dick was soaking my jock in precum.

 

"Good boy, now jerk off. And make it good."

 

I put on a good show, playing with my nips, sucking on the wet jock, and shooting a bigger load than last time.

 

"Good boy. Same time next week. Wear your jock and have a dildo."

 

And he was gone.

 

All week long my thoughts were about this man, this stranger I knew nothing about that I was going to give myself over to.

 

And I jerked off every night, imagining what was going to happen to me and shooting huge loads.

 

The next week, there I was in my jockstrap, dildo in hand.

 

"Good boy. Now, give me your address. I am going to send you a package with instructions. You will follow these instructions, and if you fail, it's over. Do you agree to this?"

 

I hesitated for a moment before I typed,

 

"Yes Sir."

 

"Good boy. Now, give me your address and give me a show."

 

My heart was pounding in my chest as I gave this stranger my address, but my dick was drooling.

 

Then I put on a show. I fucked myself with the dildo, on my back, facing the camera so that he could watch my face as I pounded my hole.

 

I shot a load that hit me in the face.

 

"Good boy. You will get a package tomorrow from FedEx. Be here next week."

 

My mind was a blur the next day and I eagerly opened the package as soon as it arrived. Inside it were three dildos, each one increasing in size with various textures, a fat butt plug, three bottles of poppers, and a plastic cock cage. I grabbed the enclosed letter and read it.

 

"Hello boy. 

 

First you will shave your cock and balls, then put on the cock cage and lock it with the plastic lock. Next you will send me two pics of it clearly showing the lock number. I had better recieve the pics before 8:00. If at any time over the next month you try to remove it, it will be over.

 

When you meet me on the camera next, you will have taken your phone and set the alarm so that it goes off every five minutes in the infinity mode. The alarm will go off exactly five minutes after you appear on the cam, which will be 8:00 sharp. The reason for this is, you will hit a fresh bottle of poppers twice in each nostril, deep and long every time the alarm goes off. I will know it's a fresh bottle, because I sent three different kinds, and you will open them on cam.

 

After you show me your locked up cock, so I know it wasn't tampered with, you will take the smallest of the three dildos and insert it in your ass. How long it takes is up to you. If you want to stretch yourself before hand, that's your choice, but the next part won't begin until the dildo is fully in you. So how many hits you've taken before its buried in you will be entirely in your hands.

 

Once it is buried in you, you will face the camera and the next timer will start. For 30 minutes, you will ride the dildo. And by ride it I mean I want to see at least 4 inches of it come out of your ass before you slam yourself back down on it. Any time you stop riding it, even for a second, it's over. And you will be facing the camera so that I can be assured you're hitting the poppers as instructed.

 

After 30 minutes, you will remove the dildo and display your hole for me.

 

As far as the plug goes, you can wear it as much as you want, and I would suggest you do, but you WILL wear it on the entire ride down here. I will know you have it in because you will send me a short video every hour, on the hour. This video will pan from your plugged hole to the odometer in your car as proof. Oh, and I've marked it so I'll know it's the correct one the entire time.

 

If you fail at anything, then it's over and your darkest fantasy will never come true.

 

Sir"

 

I looked at the dildos. The first one was probably 8 inches long and made to look like a man's cock, with thick veins running up and down it. The second one was probably 10 inches long with fat little nubs all over it.

 

The third one scared me. It was at least 12 inches long, fat, and had a thick line that wrapped around it like a corkscrew. As much as could stretch my hole, I knew I would be having to stretch it out extra good in preparation for that.

 

But that's what I wanted, to have my hole wrecked.

 

My hands were trembling as I locked the cage.

[Aces]

Hot!

Can't wait to see how that hole is wrecked

[Guest cabaretvoltaire]

Quente

[shinelover]

Fuck, this is awesome! Can't wait for the next part!!

[pozpopperpig]

Fucking HOT!  Can't wait for more!

[Bttm2go]

Excellent start. Definitely got my attention.

[wondering]

Great start!  I can't wait to see what direction the story goes in.  Hopefully a raunchy, depraved direction. 

[Rosebud69]

I realize it’s been several months since you wrote the first chapter of how you got your hole wrecked, please don’t let it be the last chapter. Your story is hot as hell,  well written and just begs for at least one more chapter to finish it.