Webcam Mistakes

At 5 sharp, Mr. Williams arrived to unlock the door. He was a tall, handsome, and extremely fit man. He was originally a tight end in the NFL but after a serious injury early in his career he turned to coaching high school sports for our school, leading the football, basketball and baseball teams to numerous state titles each.

Always friendly, he asked what I was doing here so early and I told him my ordered excuse. A look of doubt crossed his face as he clearly didn't believe that scrawny, feminine little Chrissy White was using the gym, but thankfully he didn't question it.

Our interaction over with, I hurried to my locker. Inside was a large brown box. Pinned to the top was a printed note.

Good morning Chrissy, my precious little whore. I hope you made it on time as you won't have much time to spare. Mr. Williams will be in his office for some time going over game tape, but the first players for the football team arrive at 6:30. Get down to the men's locker room and get to work quickly. Any instructions or items you'll need are in the box.

I didn't want to waste any time, so I hurried downstairs and got the box opened. On top was another note.

In this box you will find a women's razor, shaving cream, and some feminine smelling body lotion. Go into the shower, set up your webcam so I may watch you and shave every inch of your body, then apply the lotion. I want you smooth and smelling like the little sissy whore I know you are. You will then put on the outfit in the box and apply the makeup exactly as seen in the photo. Lastly, in the box you will find a backpack with a locked padlock on it and a sealed letter. You will open the letter in front of the camera only after all other tasks have been completed. It will give you your next instructions and how to open the backpack. Get going you sissy little bitch. Clocks ticking.

I didn't even want to begin to imagine what this outfit would be so I grabbed the shaving cream and lotion and got started with that first. Luckily, I was never very hairy to begin with so it only took one go over and just a quick touch up in a few spots until I was hairless. By the time I had finished applying the lotion only twenty minutes had passed. I still had an hour until the football team arrived.

Next I looked at the outfit. I was thanking every god I could think of that I had been quick with the shaving, cause this outfit and the makeup was going to take some time. It had been hidden under a piece of cardboard when I first opened the box so I was just catching my first glimpse of it. I had never seen so much pink in my entire life. Ok maybe that's an exaggeration but it was still a lot. Inside were pink stockings, a pink garter belt, pink boyshorts that said slut across the back, a pink babydoll with a glittery unicorn on the front, a long, straight, pink wig, and a pair of the tallest pink stiletto heels I'd ever seen.

I put on the stockings, garter and panties which all fit perfectly, but when I got to the babydoll I realized it was for a woman with an enormous bust. I was momentarily at a loss until I rechecked the box. In it I found a set of fake, skin toned tits and a bottle of glue to attach them, and realized my master had me going all out this morning. I quickly scanned the instructions and then applied them. They needed to be held in place for 20 minutes to dry and then they'd stick on their own. I didn't have time to hold them up and still get the makeup on so I decided the babydoll would have to do that for me. When I put it on I realized it was more than capable of the task, as I was now about three sizes too big for the babydoll, which was being pulled up by my now enormous cleavage and ended about 6 inches above my belly button.

Before I put on my heels or wig, I decided to do my makeup. This was by far the most painstakingly tedious task. I had never done any makeup before and I wanted to get it perfect. By the time I finished, with new pink eyeshadow, pink mascara, pink lipstick and overall a basically pink face, I had to admit I looked really fucking hot. It wasn't too overdone with the pink, but rather just enough that it almost looked natural but at the same time made me look like a docile and horny little slut.

With my wig in place and heels strapped on my feet, I had to take a moment to admire myself in the mirror. I looked incredible, and if it weren't for the bulge my chastity cage was making in the panties (I had left the key at home unfortunately), you never would have guessed I was a guy. I didn't even recognize myself, so I knew no one else would. When I checked the clock however I panicked. It was 6:24 and I still had to read the letter. I grabbed it from the box, jumped in front of the camera and tore it open.

Hope you got ready in time slut. It would be very embarrassing if you got caught in the boy's locker room looking like this. Your next task is to place everything into locker 149. It is not used by anyone on the team. The only thing you will keep with you is the backpack in the box and your cell phone. The rest will go into the locker. It is already unlocked for you. You will then close it and since you do not have the key it will be mine until I decide you can have it back. You will then take the backpack and phone and make your way to Ms. Howard's classroom, room 148. You can sneak through the custodians hallways beneath the school. They let out right next to her classroom. In her classroom is a large supply closet. In that closet is the key to the front pocket of your backpack, and in that pocket is more instructions as well as the key to the main pocket. Get moving slut. If you took as long as I think you did the first football players will show up any second now.

He was right, it was now 6:28. I threw everything into the locker and as I was closing the lock I heard a few groggy voices at the door.

I didn't have time to think about following the orders or disobeying them, I just ran/hobbled in my heels to the back exit from the locker room and dove through the door into the custodians hallway just as I heard the other door open.

I heard a curious voice call from the doorway, having heard me slam through the door, but another voice responded saying it was probably just the custodian.

"I thought I saw a chick though!" I heard the reply.

"You always think you see a chick asshole." The friend replied.

"Eh, fuck you man."

"Fuck you too Buck."

Shit, it was Buck Thompson that saw me. I had managed to avoid him for the past four years, but he was a pig headed, moronic asshole whose only reason for being in this school was for being so muscular that he could block anyone on any defensive line from any other high school. He was regularly bullying whoever was nearest him, but as I said I had managed to be spared for four years and wasn't looking to start with him now, especially not looking like this.

I snuck through the halls as quickly as I could, getting lost a few times, but I finally managed to make it to the right exit. I poked my head out into the hallway and saw the coast was clear, however my blackmailer lied about the proximity to the classroom. It was five whole doors down and I had to speed walk down the hallway to make it there unseen.

Thankfully, I had gotten used to walking in heels a little over the past few minutes and was able to make the trip rather quickly, but I was afraid someone would have heard my heels clicking and peeked out of a classroom. I made it up to the door and just as I was pushing the door open I heard Mrs. Davis, our school's secretary, and Mr. Harrison, our school's principal turn into the hallway having a conversation.

I took another dive into the classroom and rushed to the closet, hoping they wouldn't pass the classroom and see me in here, dressed in next to nothing. My luck, as it turns out, was even worse. I made it to the closet in time, but as the closet door closed I heard the classroom door open, and Mrs. Davis and Mr. Harrison enter. They were making small talk about Ms. Howard.

"I hope she's feeling better soon." Mrs. Davis said.

"Yea, thankfully it's only the flu and nothing more serious, although it's a bad strain this year. She probably won't be back until next week." Mr. Harrison responded.

"But it's only Monday! You really think it will be all week!?" replied Mrs. Davis.

"Yes I'm afraid so. She asked me to lock up her closet so that students don't try to steal any materials. Apparently some expensive paints went missing just a few weeks ago when she was on jury duty."

"Then we'd better lock up."

By this point the two voices were at the door. My heart was in my throat, thinking they would open it to make sure everything was in order before locking it, finding this scantily clad slut gawking back like a deer in the headlights. But that would have been better than what actually happened. Instead, I heard the lock click and the principal and secretary walked away, continuing their conversation, having no clue the fate they unwittingly doomed me to.

I figured I may as well follow through the rest of my instructions while I was trapped. I found a light switch and flicked it on, then saw the key hanging on a hook on the wall. I took it and opened the front pocket, finding yet another note.

The rest of your day and your week will be taken up by the following instructions. First, you will call the school, tell them you are sick with the flu and will not be in for the remainder of the week. You will also call your job and inform them of the same. After that, you will text your mother and tell her you will be staying at a friend's house this week. You have a very important project due friday and don't want to have to take up so much time driving back and forth from home. After that is all done you will leave your phone on the floor and I will retrieve it when I make my first visit this afternoon. In the meantime, you may then open the main pocket of the backpack. In it you will find two sets of handcuffs, a blindfold, a ball gag, a bottle of lubricant and your new friend for the week. You will only remove your panties, then lube up your friend, position him beneath you, put on the blindfold and gag, then handcuff each wrist to each ankle. You will proceed to bounce on your friend until I arrive at your snack time. There is a camera in the closet, so I will be watching. Get bouncing whore.

One stupid mistake led to all of this. I went from a just barely 18 year old boy with a fetish for anal to being dressed like a slut, locked in a closet in my high school, restrained and forced to fuck myself for the sadistic pleasure of a person whose identity was still as much of a mystery to me as ever. No one I thought it could've been made any sense.

Rather than dwell on any of this though, I chose the simple route. Submission. I made the necessary calls and texts, opened the backpack and froze.

How on earth was I expected to fit this goliath of a black dildo in my ass? This thing made my fist look like child's play. It wasn't quite as wide, but still easily 2 inches plus in diameter, and it had to have at least 10 inches of length insertable. That made it nearly twice the length of my first dildo and almost twice the girth, its total volume probably three times that of my first one.

Again, I didn't want to spend all my time overthinking, so I chose to act. This was for two reasons. The first was that the more I thought about any of this, the crazier and crazier my thoughts became, and I was likely to drive myself right off the deep end.

The second reason was more simple, more carnal. As much as I hated being controlled like this, I loved it at the same time. Something about giving the total control of my life away to someone, anyone, was so erotic, and my situation has had me constantly aroused since it began. As much as I hated to admit it, this was the greatest thing to ever happen to me.

So I followed my instructions and set up my toy with the lube, blindfolded and gagged myself, and set up my restraints. Then, hovering over the dildo, I slowly lowered myself down onto it, trying to inch just a little past my too tight sphincter. I struggled at it for a minute, pulling my ass cheeks wide with what little wiggle room I had in my handcuffs, but before I made any real progress I was interrupted by the sound of the closet doors lock being undone.