Webcam Mistakes

I guess I should've been more careful. But what can I say? I was a young man and I was stupid.

I had just passed my 18th birthday a month earlier and I had treated myself to my very first, brand new dildo. Nothing crazy, only 5 or 6 inches long and just 1.5 inches girth with a suction cup base, but it was perfect for a beginner.

Luckily, I had plenty of time to use it at home too. My mother, who worked the late shift 6 nights a week as a bartender, was a single mom to an only child. My father, a former cop, had been killed in a drug bust when I was only a child.

So, after High School ended each day, I would go to my job until 8, then I would have an entire night and an empty house to do whatever I pleased.

As a senior, taking only 4 classes, none of them assigning homework, this left me tons of time to get intimate with my new friend.

This started innocently enough; experimenting in different positions, pistoning in and out of myself, feeling myself gaped, but quickly I wanted more. Just after my first week, I bought a chastity cage and began denying myself orgasms from touching myself, relying solely on anal stimulation.

Soon I needed more though, and within a month I was tying my feet and legs apart in a standing position with some rope I found in my garage, using the police handcuffs my dad left behind to restrain my hands behind my back, wearing my chastity cage, and squatting over my dildo, bouncing up and down, tip to base every thrust, feeling my dildo explore every part of my insides it could reach. I even had one of those kitchen timers that I would put the handcuff key in and set for a few hours so I was helpless to escape.

While all this was going on, I would set my webcam in front of me and run one of those random webcam sites. You know the ones. The ones you scroll through to an endless stream of guys jerking off.

I had done this several nights in a row now, and I was loving every second of it. Between the amount of guys who had blown loads to me helplessly tied, fucking my tight hole to oblivion, to the ones who would laugh and call me disgusting, degrading names (something I love), I essentially had a constantly leaking locked little dicklet.

The first few nights doing this I would set the camera so you couldn't see my face, but tonight I was feeling risky. I figured with millions of people using the site at any given time, the odds of someone I knew seeing me were astronomical, so I shifted the camera up a bit and got started.

And that's where my trouble began.

I was coming up on an hour and a half of the two hours I set my timer for and I got matched with someone who had no camera on. This was nothing new, probably one in every five people didn't have one. They usually just moved on after 30 seconds or so. But no, whoever this was just sat there. Again, this is a bit strange but not unheard of.

So I did what I normally did in that situation. My camera had a built in microphone, so I put on my most seductive voice, and said, "Come on daddy. Turn on your camera and let this naughty little slut see you stroke that big cock."

It seemed like it had the desired effect, as my mystery partner almost immediately began typing. It said he was typing for at least 2 minutes until it was finally sent and appeared on my screen. As I started reading, I froze, my blood running cold. It read:

I don't think I will do that Mr. White. From here on out you are Chrissy to me. I've been very much enjoying your show here and plan on continuing to do so with my complete anonymity, at least for the time being. You are going to continue to bounce up and down like the naughty little slut you are for as long as I tell you to do so. If you do not, I have recorded this entire thing from the moment I recognized you're face on my screen. It would be a shame if your mother had to see her precious boy behave in such an unruly way, wouldn't it Chrissy? It would be even worse if it were to get out to some of your classmates. You would become the laughing stock of your entire class, your school most likely wouldn't let you even walk in your graduation ceremony if they saw something like this. So it is certainly in your best interest to do EXACTLY as I say, without hesitation little slut. So continue to bounce until I tell you otherwise. I want to hear you moan and pant like a bitch in heat, to see that pathetic little clitty drool cum. And when I am all done with you for tonight, I will send you a username so we may video chat in the future and then I will log off. If you do not obey, this video will be sent to every single person you know. I don't want to hear a single word out of your fucking mouth for the rest of the night, so to show you understand your new position in life you will continue to bounce and fuck yourself, unceasingly until I am gone. If you do not do this, I will assume that as retaliation and will begin preparing to share this. Get fucking Chrissy.

I was nearly ready to cry. Clearly this guy knew who I was and I didn't doubt for a second he wouldn't hesitate to do exactly what he threatened. What choice did I have then, besides putting on a show for him?

So that's what I did. I began to bounce up and down, erotically gyrating my hips while I violated myself for this mystery man. After only a minute or two I realized, while absolutely terrified, the message I had been sent had made me hornier than anything I've ever done or seen before and I spewed the biggest load yet of my young life.

I proceeded to bounce, up and down, up and down, nonstop for nearly two more hours. My legs were like jelly and I thought I was going to collapse any minute. Finally, after what felt like an eternity, and countless orgasms, I received the username and my new blackmailer left.

In exhaustion and relief, my legs gave out and my full body weight impaled itself on my dildo, giving me yet another mind numbing, explosive orgasm that rocked every limb of my body. I weakly fumbled for the key to the handcuffs, unlocked myself, untied my legs and passed out on my floor in a puddle of my own cum, the dildo still fully inserted into my ravaged asshole.

I awoke about an hour later in a heap on the floor, covered in cum, the dildo still shoved in my ass. Luckily my mom wouldn't be home for at least two more hours so that gave me plenty of time to clean up the mess.

After it was all cleaned up, I returned to my computer and checked the username. I added him as a new friend, hoping to find some more info on my blackmailer, but the username was MasterAnonymous and his name was first name Nunya, last name Business. The account was made two hours earlier. Clearly I wasn't getting information on my blackmailer this way. So I set an alarm and got to bed.

*************************************************************************************************************

When I woke up in the morning, I had a new message from my Master, which read:

Online. Tonight. 9:30 pm. If you're so much as a one second late, this video goes public.

Attached was a link to a private video. I opened it and there I was, eagerly bouncing up and down. The video was only 2 minutes long out of the hours I spent humping myself raw for his pleasure, but it was enough to ruin me.

I was absolutely baffled who could be blackmailing me. I know I wasn't very popular in school, in fact I had no close friends at all, but I didn't have any enemies either. And I was well liked by everyone at work, at least I thought so. So who could be doing this?

Luckily it was a Sunday so I didn't need to go out anywhere. My mom's shift that night started at 9 and after a rather uneventful day, she left and I prepared for my session with my mystery blackmailer. The second the clock hit 9:30, I saw my new master appear online and begin typing a message to me.

You're on time. Good. I don't need to punish you yet. Lay on your back, feet in the air, legs spread apart, and start fingering your asshole. Start with one finger and slowly add more. I wanna watch you continually gape yourself more more and more slut.

Yes Sir, I replied.

I immediately opened a video chat, stripped naked and laid back. Lubing up my fingers, I slowly inserted one, starting with my pointer. Having been fucking my ass with the dildo so much recently this was easy enough, and I felt my cock instantly begin to stir in its cage. I continued this for several minutes, switching between fingers, until I needed more.

I switched back to my pointer, but this time added my middle as well, and could feel my anus beginning to stretch. I worked these in and out for another several minutes, slowly opening myself more and more, before adding another, then repeated that process again and again until I had 8 fingers in my asshole, 4 from each hand, only my thumbs left twiddling outside. How stretched I now felt was unreal. I didn't think my ass could have stretched any larger, not realizing how silly this would sound in just a few short moments.

This whole time my blackmailer had been sending me little encouraging messages, things like good slut and stretch that tight little hole for daddy but now he sent his first real order since we began. I thought I would switch to my dildo now that I had eight of my fingers pulling my asshole further apart every second but I was wrong.

You've done well so far bitch but I've seen better. Remove the fingers of one hand from that pussy and I want to see the other hand disappear to the wrist. You have 10 minutes or I send these out.

Attached was a folder of hundreds of pictures, all of them showing me with various fingers shoved in my asshole, my face clearly visible in each one.

Seeing this I panicked, curled my left hand into a fist, and shoved it so hard that it popped in immediately. At first I didn't feel a thing, but after a moment I felt the pain of my sphincter being torn wide. I thought my fingers gaped me, but they had absolutely nothing on the width of my knuckles. I let out a roar of anguish as the pain set in on my sphincter and I was completely paralyzed for a moment, my full fist fully inserted inside me. I heard my computer ding with a new message. After a moment I feebly lifted my head up to read it.

That was impressive bitch. I've never seen a slut do that so quickly. For being such a good and pathetic little whore for me I will reward you. You have one minute to make yourself cum without removing your hand, and without using your other hand at all. Then, while you are orgasming, you're to remove your hand while remaining with a fist. If you can do this completely you are free for the night. If not you will be punished as I see fit. Your minute starts now.

No problem, I thought. I was just about ready to explode anyway. I pumped my hand several times inside my rectum, basically punching my prostate and in less than thirty seconds I felt my cock explode in its cage, leaving a river of cum running down my asscrack and over my wrist.

I started to pull my fist out and I realized why I was required to orgasm first. With my orgasm, my asshole muscles began clenching tighter around my wrist in short spasms. When I tried to pull out, the pain was multiplied tenfold. I froze for a second, thinking there was no way I could pull it out in a closed fist, but I was afraid my asshole couldn't take anymore of this abuse and I wanted the reward of being able to relax my anus. So I followed the old band aid motto and just ripped it off. This time the pain was immediate, although it was mixed with another orgasm, and I let out part scream, part moan that came out like a hoarse gasp as my body was rocked with pain and pleasure simultaneously.

I looked at the time and saw it had only been about 50 seconds. I was elated that I had done it! I could rest my asshole and got to sleep! Then I received his message.

1 minute and 3 seconds sissy. Too bad for you. Should've just ripped it out right away like a good whore would've instead of hesitating.

But it was 50 seconds!! I messaged him and said as much!!

Listen here you little fucking slut! Do not ever talk back to me! When I say you fucked up, you fucked up, or everyone you know is gonna find out what a pathetic little cunt you are! It was 51 seconds from when I saw you finish reading the message but you decided to lay around in your whorish little daze for 12 seconds before hand! The clock starts when I say it does, not when you decide to stop being a worthless fucking sack of skank! Now go to this address, make an account, and I don't want to hear another word from you unless it is "Done Master"! Now go!

I was furious, humiliated and dejected. This was so unfair but I clearly was in no position to bargain. Every bit of power was in his hands. So I swallowed my pride and clicked the link.

I found myself on one of those cam model websites. I had a pretty good general idea of what my punishment was gonna be but I was terrified. Unlike the website where he found me, this was an extremely popular website where viewers could choose which models they viewed so it was a lot easier for another person who knows me to find me, and one person knowing was more than enough for me.

But again, decision making was not a luxury I had right now, so I made an account, coming up with a seductive and slutty username I thought my master would like and let him know.

Ok slut. You're gonna be putting on a little show for the internet. Since that his how I came across you last night, I know you'll probably enjoy this anyway, but I'm feeling kind and will consider this your punishment. You will start a live show, and proceed to alternate hand to hand, fisting your asshole with each, until you can insert them and remove them without hesitation. You may then sign off for the night and get some rest. I will not be watching the entirety of your show as I have more important things to do but I have informed some friends about your situation and they will be keeping an eye on you for me. I have not told them who you are exactly, and since they all know you personally as well, you are to cover your face in some way. I want you to remain exclusively my pet for the time being. Get going slut.

Well that put my biggest fear to rest. I found an old halloween mask from when I was a younger, a plastic charmander mask that looked ridiculous on me, but it did the job. I went back to the site, logged into my account and started a new broadcast.

It was less terrifying than I thought it would be, and an hour in I was actually enjoying it. I had gathered over 200 viewers at this point, pretty good for my first show, and I was in a state of bliss, having orgasmed at least a dozen times.

I was reading the messages some people were sending and that made it even better. Nearly all of them were positive, albeit quite dirty, and some said they would have even sent tips if they could. Unfortunately my account wasn't officially verified yet so that wasn't possible but I would totally be cool making money doing this.

Another 20 minutes went by and I could nearly go in and out with both fists no problem. I figured maybe 5 or so more minutes and I'd be free. Then I saw a message that certainly caught my attention.

Damn I used to know someone with that mask. I always got a sissy vibe from him but I was never totally sure. Anyway, fucking hot man. Pound the fuck out of yourself.

It wasn't the message that got my attention, but the username. BBCGodMarcus. That was the name of my neighbor two houses down, Marcus. I hadn't talked to him in years. After elementary school we grew apart. With me being only 5'2" and 100 lbs with the muscle mass of a 9 year old girl, even at 18, I got more into my books and my education. Him, being a 6'5" black man with the build of an NFL running back at 18, headed more in the sports direction. He was the super star of our high school football team and there was already even talks about him playing well through college and into an NFL career.

I could see my face beneath my mask begin to turn beat red after reading this. Could this be the same Marcus that I grew up with? I had no clue and as I pondered this I realized how easily I was now fisting myself. I decided that I met Master's expectations and jumped up to sign off.

Only immediately after did I realize my mistake. If that really was Marcus he may have realized how quickly I reacted after his message. If that was him he would have immediately noticed my panicked reaction to his message. One thing I remembered about our friendship when he was younger was that he was extremely intelligent, extremely observant, and he always got whatever he wanted. If that was him I was screwed, my best bet being that it wasn't. Then I started to realize, what if it was him that was blackmailing me in the first place? That could've just been him trying to scare his new "pet". Or if he was one of my blackmailers friend's. He did say they all knew me personally. Maybe he recognized me and made the connection.

As I cleaned myself up and got into bed, these scenarios twisted around in my head growing and growing my fears as I drifted into a restless and fitful sleep.

*************************************************************************************************************

I woke up several hours later and checked my phone. I still had 2 hours until my alarm but I had a message from my Master. I considered ignoring it and waiting until I needed to get up to read it but realized if it was anything important that would take any sort of time at all I should check it out now. I didn't want to risk another punishment knowing that next time it surely wouldn't be as enjoyable as last night. I'm so glad I did check.

I heard good things about your show last night slut. My friends were very pleased. While you were busy whoring around, I went to your high school and left you a gift in your hall locker. The door to the school is unlocked at 5 am. You are to be there at that time as well. If you are asked any questions, say you want to use the student athletic facilities. Bring your camera with you. All further instructions are with your gift slut.

It was 3:45 am. That gave me about 20 minutes to get ready and still be able to make it to school for 5. While I got ready I went back to thinking of new possibilities.

This ruled out Marcus as my blackmailer. We both went to a highly prestigious private school nearly an hour away. There was no way he could have made it all the way there and back in that time

Normally it would cost tens of thousands per year to go there, but due to my stellar academics and Marcus' stellar academics as well as being absolutely phenomenal at any sport he felt like trying that day, we both received full scholarships to go. Otherwise, being from the poorest town for miles around, we never would have been able to attend.

But what if it was him? Maybe he knew someone that lived close to the school and had them put the stuff in my locker? But then he would have to tell them who I was, and my blackmailer said he wants to keep me to himself for now.

Could he have given one of his friends a log in to his account and told them to send that exact message and when to send it? Then he could be my blackmailer and still have gone to the school and back.

Or was Marcus even involved? Did he just happen to come across my web show? If that was the case, he may not have actually known it was me, but I doubted that would slip by him. He knows what I look like well enough.

For all I know that wasn't even him, just some random guy named Marcus that knew someone that owned a Charmander mask.

I finished getting ready and left for school. As I drove, I continued to go through everything in my mind to make sense of it all, trying to figure out who was doing all of this to me. I was no closer to an answer when I arrived to the school. It was 4:55 so I waited by the door for someone to unlock it.