[Fiction] Kyle: My First Taste of Online Nudity and Humiliation - Part 1 [FICTION]

[Kylevan]

This is a work of fiction. All the events depicted here is a result of my imagination.

If you find this story offending, please accept my apologies and I advise that you discontinue reading.

This is my first story here on getDare but was deleted because my first account was banned. The reason for banning was because the administrator thought I was a minor (I'm 23 by the way).

I decided to post again the story hoping that this account will never be banned like my first one.

To anyone who will read this post, you are welcome to post your comments. Any form of comments are welcome.

Enjoy.

Part 1. It Began with a Simple Dare

This story is comprised of several parts (though I'm still undecided if how many parts). And every part will be composed of several sections. This particular part of the story is dissected into 12 sections which you may read at the comments section following this post.

Section 1. How It All Started
Section 2. And Then I Was Blackmailed
Section 3. I Was His Unwilling Boytoy
Section 4. I Was Forced To Do More
Section 5. I Feel Like a Cheap Whore
Section 6. I’m a Slave at My Own Home... and at School
Section 7. My Dignity was Lost
Section 8. Library Exploits
Section 9. Another Day of Humiliation
Section 10. A New Unknown Audience
Section 11. Illegal School Sleepover
Section 12. I Was Forced To Act Like a Wild Animal

Hope you like it...

[Kylevan]

My name is Kyle.

Everything here happened during high school.

It all started when I was sixteen years old, when someone sent me a private message on Facebook. The sender's name was Jack, at least that was his Facebook name. He was friendly. We have had exchanges on chat and soon I accepted his friend request and thought no more about it.

After a few weeks, he sent me another message asking if I wanted to play truth or dare with him online. I got curious. I was alone that time because my parents were on a trip with friends for ten days. Alone and bored, I finally replied yes. Then he replied asking if me if we can make the game more interesting so I said sure why not.

After waiting some time, he replied with a long message about what was going to happen. The message said that we can play truth or dare, or he can give me dares that I need to perform in exchange for rewards if I successfully did all the tasks.

I asked Jack what will be the rewards and he replied saying it could be in a form of electronic cash via PayPal or items from Amazon. I told him that I can't afford that kind of payment for him. It got me kind of disappointed because I admit that I liked the idea of getting items from Amazon or some extra cash from making the dares but I have no money to reward Jack if he successfully perform the dares that I'll give him if we play.

Jack then proposed that he will be the one to give me all the dares and all I have to do is perform them. But there's a catch, all dares must be performed within a certain time limit depending on the dare and I have to film or record everything on video or photo as a proof.

I thought about this for a minute. I asked him if all he has to do is to give the dares and I will have to do them all just to clarify if I understood him clearly and he said yes. I told him that I am getting the worse end of the deal and he said that I will be rewarded for every dare accomplished successfully so it's not really a bad deal. Then I agreed.

He then asked me if what type of reward I prefer. I told him that I don't have a PayPal account but I do have an Amazon wishlist. He told me to give him the link to this and I did.

Then he asked me if I'm ready for the first dare and I told him yes. Then he told me to choose an item from my wishlist and the dare will depend on the value of the item. I carefully scanned through my wishlist and opted for a pair of high end rubber shoes. I told Jack my selection and he told me to wait as he formulate my first dare.

After about three minutes, he sent the first dare via private message:
For your first dare:
“Video yourself and slowly strip on your underwear. Take a full body picture of yourself outside in the front door while (a) on your boxers and (b) fully naked, no article of clothing must be visible in the photo including footwear and accessories such as wristwatch, chokers, etc. and your hands must be on the back of your head. Take a full body picture of yourself naked to every part of your house. You must be fully naked and your full body and face must be visible in the photo. You must also have an erection on all the photo. All the parts of the house must be photographed with you in it including the basement if you have one, same if you have a balcony, attic, garage, and every bedroom you have in the house. You must be sitting in a couch or sofa in the living room picture. As for the dining room, you must lie facing up and spread-eagled on top of the dining room table. Lie on the bed facing up with your hands on the back of your head on all the bedroom pictures. Also you must have an erection on all the photos. You have one hour to finish the task. Send me the video and photos as proof.”

Suddenly I was scared. Should I do the dare or not? After all Jack was a stranger I just met online. I didn't know any information about him. Right, so I decided to check his profile page. Nothing much says about him on his page. Only one photo is present, his profile picture which is a picture of an ocean. No information either about his age or location. But he has 296 friends listed. I checked them all and noticed something. All his friends, including me, were all Caucasian male in high school.

I thought maybe this Jack guy is a perv. But nothing on his posts says so. In the end, I decided to do the dare. I admit that being a 16 year old teenager with raging hormones, it kind of turned me on thinking that a stranger will see me naked.

So I picked up my phone and set it on video mode. Propping it on a tripod, I proceeded to strip infront of it until I was just down on my boxers. By this time, I was starting to feel my dick having an erection. I stopped the video filming and took the tripod with me downstairs to do the next task.

I was home alone that Wednesday afternoon so I didn't have to worry about my parents catching me about to be naked later.

As I reached the front door, I hesitated for a moment. My heart was beating fast because I was scared that someone passing on the road might see me. But then I just said to myself that whatever happens happens.

I opened the door and peered outside. The road was deserted. I can't see anyone also apart from occasional passing of cars. I didn't worry about the cars because our house has a front lawn with a large tree infront so I was partly obscured if viewed by drivers from cars on the road. But from a person walking, it's a different story.

I propped the tripod on the pavement facing the front door. I attached the phone on it and adjusted to make sure that it will take a full body photo of me. After making sure that it will take a full body shot, I set it on timer and continuous shot to take a series of consecutive photos. Then I ran towards the front door, faced the camera, placed my hands on the back of my head and waited for the camera to do its job.

After about six seconds, a series of blinding flashes went off and I hurriedly took off my boxers and exposed my erection and positioned my hands once again at the back of my head for the next photo. The flash continued for three more seconds before it stopped.

Then I picked up the tripod where the camera was still attached and positioned it to face the front lawn where the large tree is. I set it again on timer but this time, only one photo. As the timer counts down, I ran towards the tree and stood infront of it while my hands are resting at the back of my head.

Another photo taken, I picked up the tripod and my boxers and ran inside. As I was closing the door, I saw a boy walking infront our house looking in my direction. I was convinced that I was seen, although I wasn't sure.

I checked the clock and noticed that I have 28 minutes more before the deadline so I continued performing the tasks. I took a photo of myself naked in the living room, the kitchen, basement, garage and the backyard. I also lay on top of the dining table spread-eagled. Then I went upstairs to photograph myself in the bedrooms (my own and my parents). I also went to the attic and made another photograph. I also added another on the hallway for good measure. And lastly, on the balconies. First on my parents' bedroom balcony. I stood outside with my butt naked facing the street. I didn't bothered to check if anyone might be on the street.

Then I remembered the bathroom from my parents' bedroom and took one photograph there. Then I ran to my bedroom and went to the balcony and took another photograph. The large tree infront was blocking the view from the street to my balcony so no problem there. Then I took the last photo on the bathroom in my bedroom.

With eight minutes left until the deadline, I sent the video and all the photos to Jack and I took my clothes and put them on.

[Kylevan]

Fifteen minutes passed and Jack replied. "Well done. First dare completed successfully. I have purchased the shoes from your wishlist and will be delivered to you tomorrow. Choose another item from your wishlist in exchange for your next dare."

Wow, I thought. That wasn't too bad. All I have to do is complete the dares and I get the things I want.

I chose another item from my wishlist and told Jack. He told me to wait for the next dare for the next two days. He told me to keep my inbox open for further instructions. I told him that I have school tomorrow and we don't have WiFi connection at school and I don't have data plan so I have no way of keeping in constant contact via Facebook. In the end he asked for my mobile number for faster contact so I gave it to him.

It was dinnertime so I logged out on Facebook and checked the fridge for any food. I saw Mac n Cheese so I heat it on the oven. I was alone for ten days because my parents were on a trip with some friends. I have school so I didn't joined them on the trip. But I asked if I can have some friends on the weekend for sleepover and they agreed. I am an only child but they trust me enough to be left alone on my own.

After eating dinner and washing the dishes and mess in the kitchen, I went to my bed and watched TV. At 10, I went to bed and slept.

I woke up at 6 and made myself breakfast. I dressed up for school then walked.

Nothing much happened but during the last period before lunch, I felt my phone on my right pocket vibrating. We are allowed to bring phones to class as long as it was on silent mode. I checked the new message, it read:
“Kyle, it's me Jack. I knew you'd be at school today so I thought it would be the perfect time to do your next dare. For your next dare, go to the bathroom. Once inside, strip all your clothes including your underwear. Photograph yourself fully naked and with erection. Then get dressed excluding your underwear which you need to hide in your pocket. Then, go to an open field, whatever your school have. Stand in the middle of the field, video yourself and strip naked again. Dig a hole in the field and bury in it your underwear along with the key to your house and a spare key of your locker. Once you finished burying these items, you can wear your clothes again, minus your underwear of course. Then go back to the bathroom and go to one stall and video yourself jacking off until you cum. Massage the cum on your chest and stomach until dried. Do not wash your hand and get out and go to the cafeteria to eat lunch. Send me the photos and videos using a computer from your school before your first period after lunch.”

I was shocked at this. I decided not to do it because I thought it was wrong. So I texted him that I won't do the task or any more dares from him.

His reply made me more scared. It read:
“Fine, don't do the task. But remember, if I don't receive any photo or video of the task by the end of the deadline, you will see the video and photos of you naked from the last dare online. And I will make sure that your whole school will see it.”

That's when I realized my mistake. I trusted a stranger with my naked photos. And he was using it to blackmail me. I have no choice but to do his bidding. I have 30 minutes left until lunch and an hour lunch break so I have a total of 90 minutes to do the whole task and send the photos and videos.

I raised my hand to get my teacher's attention.

"Yes, Kyle?"

"Can I go out? I think I'm gonna throw up."

She said OK.

I hurriedly walked outside and went for the boy's bathroom. I locked the door in case someone might enter. I removed my shoes and socks, then my shirt, jeans, and lastly, my boxers. I jacked my dick a little to get an erection. Without a tripod, I propped the phone on the vanity and set the timer. Using the front camera to get a good view of myself on the screen, I took three photos with different positions.

Then I dressed again but pocketed the boxers on my jeans. My erection doesn't seem to subside easily. All the excitement rushing to me seems to make it impossible to let my dick cool down. I wore a tight fitting jeans so my erection is noticeable. Without a boxer, the feeling of my dick touching the jeans is weird. I have difficulty deciding to whether let my dick go sideways or upward. In the end, I decided to let it go upward because letting it rest sideways will make a weird bulge in my jeans towards one of the front pockets. But letting it go upward will make it seem more balanced.

But the head of my dick was poking just above the jeans waistline. And the sensational that I felt while the jeans waistband touches my dick was enough to make me horny and finish the dare.

[Kylevan]

I went outside and ran towards the athletics field. Our school's sports field was at the very back of the campus. Beyong that was thick woods which was off limits and separated by a 3 meter fence.

The field was not well kept, what with the low budget provided by the school. I ran on the center of the field and set the phone on video mode. I propped the phone on the ground supported only by a rock to stand and I took off all my clothes including the shoes and socks. I pulled my jeans last and now I am fully naked, sweating because of the sweltering hot brought by the sunny weather. I kneeled on the ground and started to dig using my hands which was hard because the ground was not wet. After about ten minutes and I was convinced that it was deep enough, I pulled out my boxers from my jeans pocket and wrapped in it the keys to my house which I was keeping in the other pocket and the spare key to my gym locker.

I placed the items on the hole and covered it with the same earth I dug from it.

Then I quickly put on my clothes, jeans first, then the shirt, socks, and lastly the shoes. I stopped the phone from filming and picked up the rock and placed it on top of the burial mound.

Halfway to the bathroom, the lunch bell rang and soon the hallways were full of students coming and going in every direction.

I made my way to the bathroom only to be alarmed when all the five stalls were occupied apart from the ten urinals outside the stalls. I decided to go wash my hands first in the sink. After all, Jack didn't told me that I couldn't wash my hands after the digging part. He only told me not to wash after the cumming and massaging part.

Ten more minutes passed and one occupant left the stall so I went in immediately. I placed the toilet seat and cover down and started the phone on filming. While holding the phone with my left hand and directed at myself, I unzipped my jeans using my right hand and jacked fast. I need to finish this task because I only have a quarter an hour left to send the proof to Jack.

After three minutes, I was able to cum a huge load on my chest. Some even managed to land on my neck and shirt which was curled up my chest. Still using my right hand, I spread the cum on my chest and whole front of my upper body but there were still more so I massaged them on my dick, pubic and crotch area. The cum on my neck, I scraped it and applied on my chest area where my shirt was curled up.

My upper body was now wet with cum and the smell was overwhelming. I continued to rub my chest until the cum dried up. By this time, I was the only one left in the bathroom. I quickly zipped my jeans and stopped the phone from filming. As I walked out the bathroom, a wet stain was noticeable on my shirt and crotch area of my jeans but I didn't care. I went to my locker and took my lunch which consists of a sandwich and energy drink. I finished eating in four minutes then grabbed my phone connectivity cord and ran for the library to send the videos and photos.

The connection at school was not very promising because of the very limited budget but I have to make do and send the videos or else, my naked photos from yesterday will be sent to the school if I failed to deliver.

Thankfully there are unoccupied computer terminals so I chose the one at the back, facing the wall so no one might look over my shoulder without my knowledge. I hooked my phone using the connectivity cable and logged on to my Facebook account. I sent first the photos to show that I did the challenge. This way, Jack will be informed that I did the task even if the videos were delayed because of the connection situation.

Jack replied, "Incomplete. You have 26 minutes left before I will post your naked photos. I expect to receive the rest of the task in 26 minutes or else."

I told him that connection at school was very poor so the video upload will take some time.

He replied, "I don't care. That is your problem, not mine. A dare is a dare."

I was really scared and sweating really hard even though the library is well ventilated. My heart was beating fast and I thought I was gonna faint. The first video from the field which is the larger file was now halfway on its upload. Time check: 18 minutes left.

By this time, my shirt was now fully soaked in my sweat as well as the upper part of my jeans. Six minutes more passed and the first video uploaded completely. Then, the smaller sized video started uploading. With twelve minutes left, I thought my breathing stopped and the world around me stopped. I was wishing that this was all over. Then, the screen prompted me that video upload was complete. I checked the time and was relieved that I completed the task with three minutes to spare.

I waited for Jack's reply and he said that he will review the videos first before he can give me his decision if I completed the dare successfully. I logged out of Facebook and cleared the browsing history and head back to the classroom to get my backpack which I left during the last period.

I went to my teacher for the next period and asked if I can skip the rest of the class because I am not feeling well. She gave me her permission and issued an excuse slip to be given to the teacher for the next and last period. I took the slip and went to look for my teacher for the last period. After giving him the slip, I walked home.

[Kylevan]

Upon reaching the house and my front door, I instinctively reached for the key in my jeans pocket and suddenly remembered that I buried it earlier at school field along with my boxers and key to my gym locker. Good thing we keep a spare under the planters by the front porch. I went to pick it up and opened the door.

I went straight to the bathroom to shower. I wanted badly to clean myself because the combined scent of dried cum and sweat was not very nice. I washed myself twice before finally dried myself with a towel.

As I was rummaging my cabinet for clothes, the doorbell rang. I wondered who might that because I was not expecting any visitors and my parents were not due home for nine days. Besides, they have their own keys so they won't rang the doorbell.

I quickly wrapped my lower body with the towel because I wasn't wearing anything including underwear. I ran downstairs and opened the front door.

It was a delivery guy holding several boxes. He was looking for the consignee which was me. He gave me the delivery papers and told me to sign my name as an acknowledgment of the receipt of the deliveries. I checked the item description and one of them was the rubber shoes. But I was surprised that other items were also included in the delivery. And it wasn't on my wishlist, but I signed my name anyway because the items were already paid.

The delivery guy handed me the boxes and left.

I closed the door and went to my bedroom. I set the boxes on my bed and opened them one at a time. First, I opened the box containing the shoes and tried them on. I was glad that they fit and they were comfortable. Next, I opened the smaller box than the shoe box. It was a digital camera. And it was the good kind. High resolution and can also take video in high definition.

Then, I went for the last box. It was unmarked and by far the biggest of the three. As I opened it, I was surprised by what it contains. There was a small box of some sort medicine, I think. In it were blister packs containing blue pills. There was also a dildo/vibrator. Some sort of circular leather with metal spikes and rings attached. There were five of them, one big and four smaller of the same sizes.

There was also a leather blindfold and a plastic ball attached to an elastic band. The last item on the box, I have no idea what it was. But it has a lock and key.

As I was pondering on why these items ended up being delivered to me, my phone's screen lit up and vibrated on top of my PC table. I checked and sure enough, a message from Jack was on my inbox.

His text was:
“I reviewed the videos and was satisfied. You have completed the second dare. Keep this up and we won't have any problem.”

I thought maybe for him, but for me this is all a big problem.

I texted him back telling him that I already received the shoes "along with some other items".

He replied that he added the digital camera because the photos and videos I sent him were not in high definition. From that moment, all the dares must be photographed or filmed using the digital camera.

I asked him what were the third box for. He told me that the third box were to be used in the succeeding tasks. But first I must charge the camera's battery and keep it ready for the next dare. I plugged the battery to its charging slot and hooked it on the electrical outlet.

[Kylevan]

While the battery was charging, Jack told me to get the chastity lock and put them on. I told him that I didn't know what a chastity lock was and he sent me a photo of it along with the instruction on how to put it on. So that was the name of the thing with the lock and key. He told me to connect via Skype and give him my Skype ID so that he can see me while I put the chastity lock on my dick.

I did what he told me and after we were connected, I looked at the screen to see what Jack looks like. But the video from the other end was disabled as well as the audio so I was the one broadcasting a live feed to the other end. But Jack relayed the instructions to me via the chat.

First he told me to strip naked. Since I was wearing only a towel, I just simply removed it while facing the webcam. Next, he told me to wear the chastity and lock it on my dick. I unlocked first the chastity because it was locked, then wrapped it on my penis without difficulty because I didn't have an erection this time. Then, I locked the contraption in place. I flashed my dick to the camera to show Jack that I'm finished.

He then told me to wear the collars on my neck, wrists, and feet. I was sure that he was referring to the round leather hoops because that was the only items left which I didn't know the name was.

I unstrapped the bigger hoop and wrapped it around my neck and strapped it back on. Next, I strapped the rest of the hoops on my wrists and feet. After that, I faced the camera and showed Jack that I'm done. He told me to kept them on until he says otherwise and that I am not allowed to get dressed. He also told me that he also added other items along with the hoodie that I told him on my wishlist. I asked him what were the additional items but he only said that it was a surprise for me the next day.

He then told me to lie on my bed spread-eagled and wait for the next instruction. He also insisted that I leave the Skype chat on and direct the webcam so that it will capture a live feed of me lying naked on my bed.

I tilted the camera to face my bed. As I was about to lie on my bed, my phone vibrated on top of the PC table. A text from Jack:
“Oh, and by the way, take one of the pills from the box and swallow it. Then, lie spread eagled and don't move no matter what.”

I hastily put the pill on my mouth and have second thoughts if I will swallow it or not. First of all, I have no idea what the pill was for and second, I have no idea what it will do to me. But I have to do what Jack says because he have enough videos to blackmail me. I swallowed the pill and lay on my bed above the sheets. I spread my legs apart and my hands.

About twenty minutes passed when I felt that I was having a semi erection. A little more time and that semi will be a full erection. The chastity cage was wrapped around my dick and a full erection will not be contained by it and sure enough after two more minutes, my hard dick was crumpled inside the chastity cage. And it hurts so much I can't bear it. I feel the urge to jack off and release my load but I was forbidden to move. All I can do was moan and groan as the mixture of ecstasy and pain was evading me.

Then I heard a laugh. It was from Jack, who apparently decided to activate thr audio from his end but not the video. His voice was not too deep which I guess is from someone who was in early twenties.

He told me that the blue pill was viagra and it is for sexual arousal. That explains why I was having a hard on and urging to release my load.

I continued to groan while Jack was laughing on the background. After a while, he told me that I can only unlock the cage after I completed his next dare for me but this time, he told me that I can choose three items from my wishlist. I told him what I wanted then he said that I could stand up now and eat dinner but warned me not to remove the cage from my cock.

I disconnected the Skype chat. But as I was about to go to the kitchen, another text from Jack came:
“Hey Kyle, I changed my mind about the dinner. Because you chose three items from your wishlist, you have to do three tasks as part of the dare. First, you must order pizza for your dinner and have it delivered to you. Once the delivery arrive, you have to accept the delivery in your present state. Meaning, you have to be naked and wearing only the collars and the chastity cage. Also, turn on the front porch light and the lights from the living room. Film the whole thing and send the video to me as proof.”

[Kylevan]

Fuck! That was insane. But I knew that I have to obey or the consequence will be severe. I picked up the phone and ordered a large pepperoni pizza. Then I set up the brand new digital camera on a tripod and positioned it so that it is pointing towards the main door.

After twenty minutes, the doorbell rang. I switched on the front porch light and the main light by the living room and opened the door. The delivery guy was dumbstruck by my sight. Here I was standing naked with only leather collar and cuffs and cage on my dick. I think he might be 19 or 20 but I can't tell. I grabbed the pizza from him and handed the money to him. He wasn't talking the whole time. It was maybe twenty or thirty seconds had passed before he finally moved and left. I guess he was shocked by the events.

I set the pizza on the table and stopped the camera from filming. I went to my room and hooked the camera to my computer and uploaded the video and sent it to Jack. I didn't wait for his reply and went downstairs to eat dinner. After I satisfied my stomach hunger, I went upstairs hoping that I could also satisfy my sexual hunger. I checked the computer and still no reply. Maybe he was still watching the whole video.

I couldn't resist the urge anymore so I ended up humping my pillow. I wasn't satisfied enough by this but it'll have to do for now. Stupid pills, was everything I was thinking about.

After about three minutes of humping, another text came from Jack. He said that the first task was completed successfully although he was expecting to see me and the delivery guy having sexual intercourse. I thought no thanks but I'm straight. He went on saying what will be the next task. He told me to go out tonight naked and lock the house. Bring the key to the chastity cage but do not bring your front door’s spare key.

I was to walk to school naked. Once inside the school, I have to make three full body shots to every classroom and any other rooms in the school, even the faculty rooms and principal's office. One shot must be full frontal, one of my back and at least one more shot in each room. If a room is locked, I have to use the vent as access. Then I have to use the computer in the library to send the photos and the video of my walk from home to school. All the photos and the video must be sent before midnight tonight.

The time was 8:00 so I have four hours to do the task. Even if I didn't want to do the task, I have no choice but to do it because I don't want my naked photos to be published online. Plus, I was very horny and really needed to release my load so I decided to do it immediately, knowing that the time to send the video will take up most of the time since the video is expected to be larger in size this time because of the new camera.

[Kylevan]

I picked up my phone and the camera and went out the house, locking the door behind me. I was locked out of my house stark naked. I have no other choice but to continue. I started the camera filming and pointed it at me. I have to be very careful not to attract any attention.

Good thing that my neighborhood kept themselves at home after dark so I don't have to worry for now. That is until I reach the end of the street and towards a road with occasional cars passing in both directions. Street lamps were spaced at fifty meters in this point so I will be exposed once I am under the lamp's bright light. I timed myself so that once a car was passing, I am well away from the bright lights of the street lamps.

The school was two kilometers away so it will take some time before I reach it. The lit road comprised the first kilometer until an intersection where I need to cross the street and take the path on the other side. By this time, more and more cars were passing but I took my chances and crossed the road running to the other side. I didn't stopped until I was well away from the occasional flashes of headlights from the passing cars. Ten more minutes and I finally reached the school.

Good thing about this is that we have no guards on duty round the clock. The school funds were not sufficient to afford one so the school was left only to secure itself with padlocks.

Of course my job tonight won't be easy. I need to figure out a way to get in. After circling the building, I noticed an open window, a bathroom window. It was two meters high and I wasn't sure if I could fit in. But I have to take my chances. I circled back and took the garbage bins I saw earlier and propped them on the wall below the window. This will serve as my foothold.

I stood above the bins and swung the window to open wider but to my dismay, it won't budge. It was the type that opens only about a quarter, the kind that was for bathrooms. The good news was that there were no railings so I can squeeze in.

I poked my head inside with little difficulty. I tipped my head sideways and managed to get my neck in. Then I slowly inched my way inside until my upper body made it in. The most difficult part was to get my lower half which was made difficult by the chastity which was still locked on my dick.

Pulling my hips then I finally made it inside and I dropped on top of the vanity sink. Good thing I didn't broke any bones and thankfully I was still holding my phone and the camera. I was afraid I dropped them and broke.

I checked the phone and there was a message. It was from Jack, again. It says:
“One more thing, all the photos must be bright and crystal clear. Good luck...”

That bastard. Now I have to turn the lights on. I don't want to attract attention. I may be alone inside the school but I can't guarantee that no one will see the lights inside the school from outside. A passerby might notice and report to the police.

Then I remembered that flashes from camera is enough to take a bright photo so I tested it. I propped the camera on top of the vanity then walked backwards to where I will be seen full body. The timer counted down and the camera flashed. I checked the photo and was satisfied by the result. The photo was bright and clear so I continued to take the second and third photo.

Then I walked out of the bathroom and went for the stairs and walked until the topmost storey, the third floor. I went to the farthest room and decided to start there and work my way down. I turned the doorknob, it was unlocked. It was a classroom. I decided to be photographed standing in front so I positioned the camera on top a desk facing the whiteboard and I stood infront of it as the timer goes. After the first flash, I turned so that my backside was facing the camera and waited for the second flash, then I gave a sideward position for the camera.

I repeated the procedure for all the classrooms on the third and second storey which was all unlocked. On the first floor were two more classrooms, chemistry and biology labs, faculty rooms, principal's office, the library and cafeteria, and some supply closet and bathrooms separate for boys and girls.

Luckily, everything was unlocked so I have no trouble taking the pictures. Finally, I went to the library to send the video and photos. I used the same terminal as last time. The time is already 11:06 so I have less than an hour to send. After 26 classrooms plus various other rooms, I have over a hundred photos to send and a large file sized video waiting to be uploaded.

As last time, I sent the pictures first then the video after that. I decided to compressed the photos in one archive to lessen it's size and sent it. While the photo archive was sending, I compressed also the video in a single archive and queued it to the upload list after the photos.

The upload process seems to went forever. I'm really growing impatient owing to the fact that I was sexually aroused, thanks to the blue pill, and I really needed to cum badly. Eleven minutes to midnight when the photos and video was sent. Jack sent a reply to wait and do not log out just yet.

Ten past midnight when Jack finally replied:
“I saw all the photos and the video. Second task completed successfully. Now, for your third and last task. You have to choose a hardbound book in your library and bring it to me.”

[Kylevan]

I went to the rows of bookshelves and took a thick book in leather bound at the back of the library. I showed it to Jack via the phone Skype chat. He then told me to leave the computer on, do not log out. Take my phone, and the camera and go to the field where I buried my boxers, key to my house, and spare key to my gym locker.

I went out the school building through the library window which I unlocked inside and left it open. I made my way until I reached another school building which is the gym just behind the main building. Then I circled it until I reached the field behind it.

Once I found the rock which is my marker where I buried my boxers, I texted Jack that I was on the field now. He texted me to get the camera to film and I have to dig out my boxers. After that, I have to walk until I reached the fence separaring the school grounds and the woods. Then, I have to throw the spare key to my gym locker towards the woods.

The woods were not that thick and not so much weeds and wild bushes were growing but it was off limits for all students so it was fenced.

I started the camera filming and for the second time today, dig through the ground until I found my boxers. Then I unrolled it and found the two keys. I picked up the smaller key and walked towards the direction of the woods making sure that I was still visible by the camera (in night mode). Upon reaching the fence, I threw the key towards the woods and walked back to pick up the camera.

I texted Jack that I finished the task. He replied to me that I was only halfway through the third task. I thought this night will never end for me. It was already nearing 1 AM.

Jack told me to bring the boxers back to the library so I retraced my steps back until I reached the open library window. I felt like a thief breaking inside but I have to finish this task so I climbed the window until I am finally inside.

After informing Jack that I was inside the library, he told me to flip the book open halfway and I have to place my boxer in between. Then I can unlock my chastity cage and jerk off until I cum. I have to make sure that my cum will land on the boxers. If a cum landed outside the book or made a mess outside the book, I have to leave it there and was not allowed to clean it. Then after that, I have to close the book with my cum and boxets between its pages and return the book to its original position. I also need to film the whole thing and send the video in immediately and then I can go home.

It was already half past one so I needed to finish this whole thing immediately. I needed to get home immediately, get some sleep because I still have school comes morning. After all, it was still Friday.

I flipped the book open about halfway its pages, then lay the boxers on top of it and flatten it. Next, I detached the key to the chastity cage which I attached to the ringlets in my collar so as not to lose it. After my dick came free, it stood to full erection. Finally, I can do my business. I started to jack furiously, wanting so bad to release. After thirty seconds, huge load, even bigger from yesterday, came shooting out my throbbing dick. Most of the cum landed on the boxers, but still a good amount of cum managed to land on the computer terminal which was still on.

I left the mess untouched but closed the book with my cum-dripping boxers sandwiched between its pages and returned it to where it was originally kept.

I stopped the camera from filming, hooked it on the computer and began the upload process. The uploading took longer than yesterday because I didn’t bothered to compress the files. But at 18 minutes past two in the morning, the files were sent. Jack replied that I can go home now and that he will give me his comments on the last task later. Then, I logged out of Facebook, cleared the browsing history and turned off the computer terminal.

I picked up my camera and phone and exited the building via the library window which I closed behind me but still unlocked because it can only be locked from the inside.

I started the long walk back home.

The walk wasn’t as creepy as earlier because no cars was visible on the lit road. I reached home at 3 am. I opened the front door using the key which I buried at school yesterday. I decided to take a shower first before going to sleep because I was covered in sweat. As I came out of shower, another message was waiting for me. It was from Jack, again.

The message says:
“I watched the videos and I am satisfied. Task three completed successfully. Now, before you sleep, I want to ask you three things: [1] Do you have school in the morning? [2] What are your class schedules for the whole day? [3] What time does your school closes on Friday?”

I was intrigued by the questions. Maybe it was for my next dare. I have had a thought to feed him wrong information about my class schedule. But then I realized that if I gave him the wrong schedule might backfire on me. It might end up me getting into trouble, so I gave him the truthful answers.

I replied:
“Yes, I have school in the morning. First period will be Chemistry, followed by Literature, then Geometry, and lastly History. After that, lunch period. Then we have PhysEd for the afternoon. School closes at 4 PM.”

I waited for several minutes before he replied. His reply was:
“Good. For school in the morning, you have to bring the following: your gym clothes but do not bring extra, shaving cream and a razor, bring also the camera. And for your school tomorrow, you are forbidden to wear underwear. That means, you have to wear only a shirt and jeans and shoes. You can sleep now.”

[Kylevan]

I fell asleep pondering on what will happen at school comes morning. I was woken up by the alarm clock. Fuck! I was asleep for three hours. I still feel sleepy but no point missing school today. If I failed to do Jack’s tasks for me, I’m getting into serious trouble.

I went downstairs to grab a quick breakfast then prepared what will I bring to school. I packed everything in my gym bag. Everything Jack required. Then, I dressed up, except boxers of course.

Everything ready including me, I walked to school. Arriving at twenty minutes before the first period, I deposited my gym bag to my gym locker and proceeded to the chemistry lab.

Nothing much happened during the first two periods, but before the second period was over, Jack texted me again, with the next task of course.

For the next task, I have to go to the library and go to the spot where I hid my boxers. Then I have to strip naked and open the book and jack off at least five minutes while sniffing the boxers. I wasn’t allowed to stop or hide if someone catches me. I am only allowed to get dressed again after I cum on the book again. But this time, I have to wear the boxers for the rest of the day. I have to film the whole thing of course and send the video via the computer in the library before the third period.

As the bell rang signalling the end of the second period, I quickly made my way to the library at the ground floor (Literature class was at the third floor). Good thing we had a fifteen-minute break between the second and third period.

As I reached the library, I went directly for the back shelf where the book was hidden. I was relieved that the book was well away at the back. The tables for reading were at the front. But I was still scared because the library has at least twenty students, most of them at the table reading or doing homework. But a good number were scanning the shelves for books.

After setting up the camera to sit on the shelf at the end so as to capture the spot where I will do the next task, I proceeded to remove my shoes first, then the socks. After that came also my shirt. I was there standing with only my jeans. I peeked to the front and saw that no one was heading my way so I unzipped my jeans and undressed completely.

Then, I retrieved the book, opened it to where my boxers was sandwiched. The cum had dried alright, but the smell was still very strong. I started jacking while sniffing the boxers still on the book. The job was not easy because the book was dusty. Apparently, no one reads it anymore. I was a minute into jacking when I feel my nose tingling. I was about to sneeze. I fought the urge because I was scared to get attention and someone might walk in and saw what I was doing.

But the urge was strong and after another minute, I sneezed. It was loud but thankfully no one noticed, not to my knowledge. Five minutes passed and I finally release another load, but not before I removed the boxers first from the book.

Satisfied that no more cum is going to drip from my cock, I closed the book and replaced it on the shelf. Then I redressed, with the boxers first and the rest of the clothes. I took the camera and went straight for the same computer terminal inside the library.

After logging into my Facebook account, I hooked the camera to it and started uploading today’s video. I have only eight minutes before the next period. But I didn’t mind because this time, I was to send only one video.

[Kylevan]

About three minutes into uploading, a chat box popped out. I didn’t recognize the sender because he/she was not on my friends’ list. The message was simple: “I saw what you did.”

I had no idea what he/she was talking about so I replied: “Saw what? And who are you?”

I waited for the reply but was shocked when it finally came. It was a photo. A photo of me jacking at the back shelves. The photo was full body shot and my face was visible. There I was, jacking my dick with my right hand while my left hand was holding a large book with my boxers on it and sniffing it.

There were no captions, just the photo. But it was enough to get me scared. I replied: “who are you and what do you want?”

The reply came. It was another photo, the same scene but different angle. It looks like the person who took the photos were behind the shelves next to where I was doing the task. But I didn’t see anyone there as I passed the shelf. Maybe that person came when I was stripping naked so I didn’t noticed.

Instead of answering my question, the reply that came was a link. Above the link where two words: click here.

As I clicked the link, the site redirected to another site. A video started to load. I was shocked when the video started playing. It was a three minute video of me jacking and sniffing the boxers. It captured until the time I was about to get dressed. While it was lower in resolution compared to my camera’s video, it still captured my whole body and my face was visible and recognizable.

Then, that person sent me another message: “Don’t worry. Lots of porn videos are uploaded online. Chances are few people might see your video and recognize you. But I can’t pass up the time to take a video of you jacking when the chance is right there staring at me. Your loss is my gain.”

I was dumbstruck. I ask him what he wants from me but he logged out and when I searched for that user’s page, it was deleted. Apparently, it was a temporary dummy account.

The video uploaded completely and sent to Jack. He replied immediately: “I will review the video later. For the meantime, you can go to your classes. Your next task will be given to you during your gym class.”

I logged out of my Facebook account, cleared the browsing history and went directly to my next class.

Lunch came but I found no appetite to eat. My mind was filled with thoughts about what happened in the library earlier. I was scared because a pornographic video of me was finally leaked online for people to see. And worst of it all, the person who uploaded the video was a student of the same school as I was, and I have no idea who that person might be.

As the bell rang for the next period, I went to the next building for the PhysEd class. I changed to my PhysEd uniform still using the boxers instead of the usual jockstrap. Today, we were on basketball but I didn’t play. I just sat on the bench thinking of what might happen to me because of the recent developments brought about my naked dares.

Halfway through the class, I went back to my locker. My instructor didn’t seem to notice because he was busy throwing commands as the game went on. As I checked my phone, another long message was waiting for me:
“For your next task, wait for your PhysEd class to end. Then, as the rest of your classmates take a shower, hide in a place where no one will see you. At 4PM when your school closes like you mentioned, go back to your locker and take the bag with you on the locker. Strip naked and take a shower. Halfway through the shower, shave your pubes. After the shower, dry yourself but don’t get dressed. Lock everything except your phone and camera inside your locker, including the keys. When it gets dark, go out to the woods where you threw the spare key to your locker. After you find it, go deeper into the woods and find a water source, make a mud on the ground and cover your whole body with it, including your hair. When your whole body is covered in mud, jack off until you cum in your hand. Lick it all up until it is clean, including the mud in your hand. Then run ten laps around the field. After that, stand on your hands and knees and walk like a dog on the field and eat the grass. Continue eating the grass for five minutes. After eating, you need to drink your piss. After pissing, go back inside and take a shower. After cleaning yourself, send the video to me and sleep inside the Biology Lab on top of the lab table spread-eagled. Set your alarm to 4AM and you can go home naked. Once at home, send me the video of you sleeping inside the Biology Lab up to your walking home naked.”

[Kylevan]

I was still debating whether to do this or not. After all, a porn video starring me was already online. But I was still lucky because the video was not made public so my school doesn’t know about it except for the person who uploaded it. But the task was very extreme and I was scared.

I decided to just wait for the school to end. If I ended up wanting to do it, then I will do it. If I didn’t then I won’t.

The rest of the gym class passed as a blur. I didn’t knew that the class was over until I heard the banging of the lockers from the next room. Then, I noticed that I am the only one left on the gym. I decided to hide outside but decided against it. My next task requires me to be inside the gym shower room. If I hide outside and the instructor lock the gym when school was closed, I will be locked outside with no way of getting in.

I looked around and noticed the grilles to the vent in one of the gym walls. This one is situated below eye level so I have no difficulty opening it. Then I slowly slid inside and closed the grille behind me, I moved deeper into the vent so as not to make myself noticeable because I was still wearing the yellow shirt and blue shorts comprising my gym uniform. I had my phone with me so I can keep track of time. I don’t wear wristwatch, for reasons that I don’t know.

It seems to go on forever but at three minutes past four, the instructor flipped the lights off and walked out the gym, locking the door behind him. I waited for another thirty minutes before finally getting out just to make sure.

I slowly made my way to the locker room and switched the lights on. This part of the gym was at the back of the building so I have no worries of someone seeing the lights because the window to this part is a small one situated above head level. Besides, I was sure that no one will be at school grounds after it closes on Friday. Most students went to shopping centers to relax and unwind. The cleaning staff comes to school Saturdays from 9AM to 5PM to do general cleaning, weekly.

I unlocked my locker and took the bag, carried it to the shower room. Boys’ shower room is a one huge room with a series of showers on two sides. No privacy stalls were installed due to low budget.

I switched the lights on and set up the camera. After pressing the record button, I undressed until I was naked and proceeded to shower. I put shampoo on my hand and massaged it on my hair then soaped my whole body. After washing, I took the shaving cream in my bag and covered my pubic area. Then, at the full view of the camera, I shaved my pubes until my dick was totally smooth. Then, I soaped and washed myself again before finally drying myself with a towel.

I switched off the camera and the shower room lights and locked my bag and keys inside the locker. Then, I sat on the bench and waited until it gets dark. I can’t do anything much at this point. I can’t send the video yet because I don’t have a data plan. The school doesn’t have WiFi so I can’t connect on the web. All I can do now was to wait and think about the video of myself posted by my schoolmate on the web.

The inside of the gym was hot because the aircondition unit was shut off as soon as the instructor left. But I can’t go out because it wasn’t dark yet. After an hour, I decided to take another shower to wash the sweat off. But this time, I won’t be able to dry myself because the towel was locked inside the locker so I stood inside the shower room and let the water drip off of me until I was dry.

I checked the window and saw that it was starting to get dark. Soon, I will need to get out and do the next part of my task. Thirty more minutes passed and it was finally dark. So, I switched off the locker room lights, took my phone and camera and started it filming. Then, I went out the gym building via the front door.

The gym’s front door is locked by a doorknob which can be unlocked from the inside without a key. As I walked out the gym, I closed the door behind me but left it unlocked for me to get back. I made my way to the back field until I reached the perimeter fence separating the school from the neighboring woods.

[Kylevan]

It was dark the last time I threw the key so I have the faintest idea where it might be. But luckily, the key was attached to a keychain which I might be able to spot easily. I threw my phone to the other side. Still holding the camera, I climbed the fence and jumped to the other side.

I started to search for the key, fumbling through the fallen leaves and under large tree roots. I was a good five meters away from the fence through the woods, when I spotted the key dangling in a branch. It was after 23 minutes. It took me this long because I was searching on the ground the whole time when in fact it was above the ground and caught on the branch.

Then I checked the phone for the next part of the task because I forgot. Right, find a water source.

I walked deeper into the woods, only walking in one direction so as to make it easier to make my way back. Ten minutes later and I found myself approaching a river running perpendicular to my path. I set the camera on a rock on the side to film the next part of the task, the phone next to it. Then, I went to the riverbank where it was muddy. Scooping mud, I proceeded to massage it on my hair just like when I shampoo. Then I took another scoop and rub it on my feet, legs and butt until it was covered in mud. I did the same for the rest of my body until I was fully covered.

Then, I went nearer the camera and jacked off infront of it until I came. I cupped my left hand to catch the dripping cum from my dick. Then, for the part that I didn’t look forward to do. I licked the cum from my hand, slowly at first. I licked repeatedly until my left hand was clean from cum and mud. The taste was awful.

I picked up the camera, still filming, and made my way back. The walk back took fifteen minutes. As soon as I jumped back to the school grounds, I walked to the bleachers to set up the camera so as to film the next part of the task. Then I walked to the other side of the field, started to run around the field to complete the ten laps required. The field was large, the size of a football field so after the ten laps, I was very tired. But I was only halfway until I complete the whole task.

Next, I stood on four and walked on the field like a dog while eating and chewing the grass on my way. The taste wasn’t good but I had to do it. I continued to chew grass and swallow because I felt hungry. It was dinnertime after all. I continued to eat grass not caring anymore that in this grass, several students, especially the members of the varsity team have pissed and spat countless times. Eurgh… I counted to three hundred to mark the five minute requirement. It felt so long but when I counted three hundred, I stood up and released the piss I was holding on earlier. I stick my dick upward so as to catch the piss pouring out of it.

My hunger and thirst satisfied, I took the camera and walked back to the gym. I went straight to the shower room and took one final shower. I went to get my house key first from the locker, went out of the gym, finally locking the door behind me.

As I neared the rear of the first building, I went straight for the ground floor classrooms and tried the windows if one was unlocked. Lucky for me, I found an unlocked window so I eased it open and went through it, then close it behind me.

The classroom was dark but I didn’t opened any lights. I just groped my way around until I found the door and made it to the hallway. Biology Lab was directly facing the classroom where I came from. All I had to do was cross the hallway. But as I turned the doorknob, I was disappointed to see that it was locked. Right, the labs were locked during after Friday classes to be opened only on Monday.

I knew that the keys were kept inside the principal’s office but it was locked too. So, I decided to enter the lab by going through the vent. All I have to do is climb on top of the rows of locker in the hallway and ease up through the vent on the ceiling.

I managed to do it and crawled into the confined space of the vent. I was sweating because it was very hot inside. Ten minutes later, I dropped myself inside the lab. Perfect. The last part of the task.

It was Friday so all the equipment and specimens were kept away and all the tables were cleared. I positioned the camera again and pressed the record button. Then, I chose a table infront and lay on top of it while still fully naked and spread eagled. My dick was starting to get an erection but I simply just ignored it. I was very tired, but I made sure to set my phone’s alarm to wake me up at 4AM before finally getting to sleep.

I was woken up by a buzzing sound. As I opened my eyes, I was wondering why I wasn’t in my bedroom. The, I remembered that I was still in school for a dare. I checked my phone and was surprised that the time was 4:30 AM. The alarm went off 30 minutes ago, but as stupid as I am, I forgot to disable the silent mode. That is why it was 30 minutes later when I woke up due to the vibrating sound made by the phone on the cold table where I was sleeping.

My back aches because of the hard table and the cold.

Then, I remembered that I need to get home before 5 AM because the neighbors mostly wakes up during this time, sometimes even earlier. I didn’t wasted another minute and instinctively grabbed the camera on the side and went out the building through a window (which I closed behind me, of course).

I walk/jog throughout the journey back home. Thankfully, no vehicle was passing on the road and I made it home safely. I sent the videos to Jack as soon as I reached the bedroom and went to sleep again.

[assassin]

I read both of your stories and they are absolutely amazing!!

Still waiting for the next part of both of them.

Keep up the good work!

[Crossdresser5]

Please keep this going I love this story