~Sleepover of a Lifetime~

[RussianRonaldo]

Thank you all for the wonderful reviews! I am sorry for not updating, I will try to do so more often. Enjoy and comment!

Chapter Ten- The "Game" Continues

I woke up to the sound of my alarm clock buzzing loudly and I got out of bed. I walked to my dresser and picked out my clothing for the day- a green Nike t-shirt and some black jeans. I got dressed and walked out of my room. As I was about to step into the bathroom my sister stopped me. "Hey James aren't you forgetting something?" she asked, as she threw a light pink thong at me face. I suddenly remembered my condition, and I just shook my head. I took the thong into the bathroom, took a piss, and put it on. I could feel the back of it running up my ass, and no matter how hard I tried, I couldn't get it to be comfortable. I went downstairs, ate some cereal, prepared my book bag, and walked to the bus stop with my sister.
I walked past the usual crowd to my friend Scottie, and I quietly asked him what he was going to do about his situation. He looked at me grimly and whispered, "I went on warpmymind and paid the $10 for a curse-breaker. I am officially free!"
"You are a lucky asshole!" I whispered back.
"Dude, just find a way to get out of your situation too. I have pictures of your sister and her friends, and as soon as you get out of your situation we can get them back!"
"Ok I will get it done by the end of the day, but can you promise me something? Delete any pictures you have of Marie."
"Bu... But.... Oh you and her... You guys are... Oh my God an tenth grader? Nice dude! Ok deal, just get it done".
The bus arrived and we all scurried to our seats and sat quietly for the duration of the ride to school. We got there and went to our homerooms. The day went fine until fifth period, when I had P.E., a mixed ninth and tenth grader class which I just happened to share with Marie and Jamie. I walked into the gym and sat on the bleachers to watch the presentation that was going on today. I got out my history book and began to read, until Marie and Jamie sat on both sides of me. "Hello James, show it to us." Jamie whispered.
"Wow I am good too, thanks for asking." I retorted as I pulled my pants of a little, just enough to show Jamie and Marie my Victoria's Secret thong.
"Very nice," laughed Jamie, "Alright, bye you two lovebirds." With that Jamie left leaving Marie and I alone.
"Hey sweetie how have you been so far?" I asked her. She told me she was fine and gave me a kiss. I explained Scottie's plan to her and she giggled, saying how she'd be happy to finally get my sister and Jamie back. We sat next to each other snuggling until the end of the period, and when the period ended we kissed goodbye and I moved onto my next class, band.
I walked in and it turned out we had a substitute teacher, meaning that band was going to be a free period. I took a seat and got cracking on that history book. Once again I was interrupted, but this time it was by a kid I barely ever talked to, Ivan Stupun, a 5'11 decently intelligent kid in my grade. He was decently good looking but kind of quiet. "Hey James so last period I was in gym and guess what I happened to catch a glimpse of?", he whispered to me. I immediately knew what he was talking about and turned bright red. He took out his phone and showed me about three pictures of me when I was showing my thong to the girls. "I don't know what you guys are up to, but if you let me in I will delete these photos right now. I have always wanted to play one of those hardcore truth or dare games. I said ok and he deleted the pictures and walked away, leaving me to read my book for the rest of the period. The rest of the day went by normally and when I got home I asked my sister if Ivan could join our game and she said sure. I texted everyone else involved, and they said ok. We all agreed to hang out again on Wednesday night (we had Thursday and Friday off).
As I was about to go to bed my sister came into the room and gave me my underwear for tomorrow- a black lacey thong and a matching bra. "You are to wear them in a bra-connection wedgie tomorrow, and don't complain about the extra bra and wedgie or I'll put those pictures of you on Facebook." I merely nodded, hid the items under my bed, and went to bed, waiting for what tomorrow would bring.

[dareman 1]

Wow great story! Looking forward to more

[MattInPanties]

Im so glad you're continuing this story! I love it

[knightgunner13]

love the story its just my cup of tea!

[RussianRonaldo]

Thank you everyone for the kind feedback... I am going to continue updating when I can... Please comment/thank.

Chapter 11- Wetness, A Wedgie, and Maybe a Diaper

Buzz buzz buzz. I woke up feeling drowsy and got up to take my morning piss when suddenly I felt wetness on my crotch. Did I really... no way... oh my god I did! I actually wet the bed, after 12+ dry years. I got my thoughts in order and quickly replaced my sheets, putting my old ones and my PJs in my closet, deciding to deal with them later. I took a quick shower and went back into my room to get dressed. I got on my thong and bra and quickly put them into my wedgie. It hurt so badly I could barely think, but I figured that it would eventually get better. I choose some black sweatpants and a green shirt and brushed my teeth. I went downstairs, ate breakfast, got my backpack, and went outside to the bus stop with my sister.
I walked to Scottie nodding a hello. "Hey bud you out of those panties yet?"
"Nope," I whispered, "In fact today I got a special treat- a thong and bra in a bra-connection wedgie."
"Dude you really have to get out of those panties, and quickly."
"I know, I know. I'm working on it buddy. It will be done by tomorrow I promise."
The bus came and we all piled on for the somewhat silent ride to school. We arrived and once again everything went normally until P.E. I walked in and saw the sign I was dreading on the billboard-
"Everyone will be getting changed today for P.E."
My mind and heart began to race. I eventually decided that if I was careful, I might be able to pull this off without anyone noticing my "situation". I walked into the locker room to my locker and slowly opened it. I looked around and saw that no one was really looking, so I quickly pulled off my pants and replaced them with some short. Next was the hard part- I took out my gym shirt and within three seconds of taking off my normal shirt I had my gym one on. After being mostly sure that no one saw my bra-connection wedgie, I walked back outside and lined up for class.
The rest of class went normally and I got changed just as quickly as I did before. The rest of the school day went perfectly fine, and at home things went normally (with the exception of me having to wash my sheets quickly) until around 8, when I got a text from an unknown number. I opened it and it contained a picture... OF ME FROM WHEN I WAS CHANGING IN GYM! Under the picture it said, "I know... wear a diaper to school tomorrow or this is going on Facebook".
All I could do was should my sister, and she handed me a diaper from her "secret stash" and nodded "good luck". I ate dinner, took a shower, and went to bed... waiting for what tomorrow would bring this time.

[dareman 1]

Great new chapter

[knightgunner13]

nice! i love it!

[knightgunner13]

come on wheres the next day!?

[RussianRonaldo]

Well sorry I took so long, but I am back now. I just sat down and wrote this all (it is the longest one so far!), hope you like it. And people, if you are reading, please comment/thank. Thank you, and enjoy.

Chapter 12- Losing Control, and a New "Friend"

A tender kiss. I love you Marie. I love you too James. Under a waterfall. The rushing water plummeting to the ground.
I suddenly wake up from my dream and stand up to get ready for school. Suddenly I realize that my crotch is soaking wet, I wet the bed AGAIN! I calmed myself down and repeated the procedure from yesterday morning, putting my sheets and pajamas in my closet. I showered and checked the weather forecast for the day- 78 degrees. I picked out some black shorts, red boxers, and a white t-shirt, and began to get dressed. I then remembered about the diaper and my mystery blackmailer, and removed my boxers, replacing them with the diaper. I got redressed and thought about my situation.
The only bright side of this entire situation was that today was Wednesday, and I have a four day weekend ahead of me. I ate breakfast and went outside to the stop and went next to Scottie. Once again he asked me if I was out of my panties, and once again I slightly revealed my diaper. "Aw dude that really sucks. I have no idea how you're going to hide that during gym." I got onto the bus and sat down alone like I do every day. Suddenly, a hot blonde girl sat next to me. I figured out I knew her- she was a 12th grader from down the block. She had a nice C rack with a giant, juicy ass. She was honestly one of the only girls I thought was more hot than Marie.
Suddenly, the hot girl grabbed my crotch, squishing the diaper . "Oh, are you wondering how I know? Yeah I am the anonymous texter, and because I have those photos you are going to become my little diapered sissy boy, for however long I decide. My name is Shannon Pit, but you will only refer to me as Mommy Shannon. Now for the rest of the day, you will only use your diaper for the bathroom. On the way home, we will sit together and I will check, don't try to fucking trick me. We arrived at school, stepped off the bus, she smacked my diapered ass, and we went our separate ways.
*At Gym that Day*
I got to Gym and happily saw the sign that we were having another assembly, so I went inside and took a seat. Scottie ran in, jumped on the seat next to me, and immediately asked me about why a hot 12th grader (Shannon) was sitting next to me this morning. I quickly made the choice that lying would be my best option for now, and opted that she just needed a seat. He then asked me what time everyone was meeting at my house tomorrow for Truth or Dare, and I told him that everyone should be there at 7pm, and that my parents would be out Thursday and Friday, so they all could sleep over and go as wild as they want. We talked about random things with our other friends for the rest of the period and I got up to go to band, and face Ivan.
I walked into band and signaled for Ivan to come to me. "Ivan are you sure you want to join the game, you could end up like me?"
"I'm sure James, honestly, I enjoy wearing women's clothing. It turns me on."
"Ok, be at my house at 7pm tomorrow. See you there."
*Back on the Bus*
I walked onto the bus, tired after a long day, and I saw "Mommy Shannon" walk on after me. Of course she sat next to me, and immeditly stuck her hand in my diaper to feel for wetness.
"You dumb little sissy bitch, why aren't you wet!?" She grabbed my balls in a tight grasp as she said that.
"Oh shit, I am s... so sorry... aw... I forgot. I... didn't have to go to the bathroom all... day. I have to pee... kind of... now if... if you want. "
She grasped my balls even harder. "Why is the fucking baby girl speaking like a big boy!?"
"Sworry Momma, I frogot. Can I does it nows?"
She eased her grip. "Better baby, you have until the end of the bus ride." I knew the bus ride was ten minutes. I relaxed my bladder as much as I could, and after about four minutes I was urinating smoothly.
"I dids it Momma, baby do goods?"
She again stuck her hand in my diaper and felt. "Yes you dirty little girl, you did it. Now listen, my parents are out of town tonight. I want you, at my house, tonight at 8pm, wearing this diaper and a pretty little pink dress. You can wear something over them if you want on the way there, only because I don't want people thinking oddly of me." We sat in silence a minute, when suddenly Shannon began to jerk me off. I felt myself getting harder and harder when suddenly she whispered, "You better not ejaculate on my hand you little sissy bitch." I knew there was no playing with this girl, so I put in all my efforts to stop myself from getting aroused. It was five minutes of pure agony, but I managed to do it. "Good baby slut, remember to be at my house, and don't be fucking late. Oh, bring extra diapers, you're sleeping over." We got off the bus and I went into my house, into my room. I snuck my sheets and pjs down to the washer, washed them, and texted my parents, asking if I could sleep over at Scottie's house. They said yes and now I had the hard part of my job.
I didn't want to tell me sister about all of this, so I had to secretly steal both a pink babyish dress and a couple of diapers. I waited for my sister to go downstairs, I snuck into her room and I took six diapers. I snuck out, put them into a diaper bag along with $40, and sat down to watch House for awhile. When 6:20 hit I turned off the TV and got my bike. I rode to the adult store about three miles from my house, and realized this was going to be the most awkward thing I have ever done.
"Um, hello, can I help you", asked the man behind the counter as soon as I walked in.
"Yes, don't ask why, but I need a pink baby dress, like right now."
"Okay." Him and I spent the next 10 minutes finding a pink baby dress in my size, and eventually found one with ruffles that went to my mid-thighs. I paid the man and went into the changing room when I put on a diaper, the dress, a sweatshirt, and some sweatpants. I put my old clothes into my bag, and checked the clock. It was 6:45, I had 15 minutes to get to Shannon's house.
*6:56, Shannon's House*
I rang the doorbell and waited for around 2 minutes for her to answer. She pulled me in and led my into her room, a bright pink average teenage girl's room. Her laptop was sitting on her bed, with a website called "GetDare.com" open on it. "Now you little baby take off your coverings and let mommy see how pretty you look." I removed my sweatshirt and pants to reveal the pink ruffled dress and the diaper sticking out from underneath. "Aw did little baby have an accident?" asked Shannon, just as she lifted the bottom of my sagging diaper."
"What are you talking about mommy, I was dry..." I stopped dead in my tracks. Holy shit, I pissed myself without realizing. First the bedwetting and now this, what was going on?
My thought process stopped right there as Shannon told me to remove my dress and diaper, and I did as commanded. She laid me onto the floor and got a new diaper from my bag, and put it on me with a little too much skill. She commanded me to put the dress back on, and as soon as I did I saw that her webcam was on! She was getting video of all of this!
Shannon saw that I noticed and began to explain, "Okay so you know how I am 18 right? Well I second I turned 18 I registered for this site called GetDare.com, where all of my kinkiest fantasies lay. It is a sight where people give each other dares online, ask each other truths, tell stories, or even just converse. I am right now in a dare called, Control My Screen or something, and right now eight people from that website are watching us, and whoever wants to watch us shall do so, until I get bored of this". For some reason that turned me on, a lot, and just then a chat message popped up and Shannon's screen.
"What is the Sissy Bitch's name?"
She typed back, "James Cooper".
She suddenly turned off her laptop, giggling with joy. "Hah, hope no one there knew you. Know sissy bitch, drink this." She handed me a weird orange drink and I drank it.
***
I came to two hours later, in my dress and... WET diaper!? Once again, I pissed myself in my sleep. Again my thought train was interrupted by Shannon, "Hello baby, mommy tied you up, oh and she might and stuck a couple of marshmallows up your butt and gave around three liters of coke while you were asleep. Well bitch babies go to bed at 9, so night night wittle baby!" With that she turned off the lights, and although I tried to scream, she had gagged me. I eventually fell back asleep.

[knightgunner13]

thanks for posting and I love the including of th share my screan thread it adds realisaim to it.

[RussianRonaldo]

Thank you I'll post again whenever I get the chance.

[gekostar1]

coool story bro keep it going

[RussianRonaldo]

Okay so here is another update, i had some free time on my hands so I figured why not. This one is about 700 words, shorter than usual, but longer then the last 2 (not counting 12). So thank/comment, and if you have any ideas for the story please feel free to let me know! PS- This chapter was mainly a transition chapter, the next one should be very long and interesting.

Chapter 13- Fun with Mommy Shannon

I came to sometime the next morning. I tried to get up, but then remember what I had gotten myself into. "Hello baby," said Shannon sweetly, "Hope you had a good night's sleep. Right now it's 9am and oh boy did baby have a messy night." It was just then that I noticed the rancid order coming from my diaper, along with the unmistakable feel of shit and piss in my diaper. It felt like it was on the verge of leaking.
"Mommy Shannon..." I started, "can wittle baby James have a diapy change?"
"Of course the baby can, but only if the baby uses HER real name, Jamie."
"Sworry mommy, can Jamie have a dwiaper change?"
"Of course, after you give me a nice organism!" With that Shannon took off her jeans and thong and stuck her pussy into my face. I took the nice tender pussy as a gift from god, and I began to pleasure her. After around five minutes of her moaning and my tongue doing more work than it has ever done before, Shannon put her thong and pants back on and untied me. Shannon continued speaking as she removed my dress and change my diaper, "Okay little Jamie I am your new Mommy, I added my number to your phone under Mommy Shannon, and if I ever tell you that you are coming over, you will do so. I will always give you a 48 hours notice, so it is fair. Now if you ever fail in your duties, I will post the original pictures, and the ones from last night, onto Facebook. When you are around me, you will always use your diaper, refer to me as Mommy Shannon, and speak like the fucking baby you are. Now you are staying here until noon, after that you may leave, but you have to walk home in your baby dress." Shannon stopped speaking, received a roll of duct tape, and taped my penis and balls down. "Sorry baby, but wittle girls don't have penises silly! There, I'm done, now get up, and put these on." With that Shannon threw me a pink push-up bra, a miniskirt, and a very tight shirt. I put them on and followed her downstairs where two plates of food where set up, one of waffles and one of babyish cereal. I sat down and began to eat the cereal and Shannon ate her waffles, and when we were done we went back upstairs into her room, and Shannon got back out her laptop.
"Okay baby now we are going to have some fun on Omeagle! You are going to stand on there, you don't need to show your face if you don't want to, just do whatever they want you to do." She turned on Omeagle and typed 'Do whatever you want to me' to every person we encountered. After 15 minutes of people jerking off, we got to two hot girls who looked to be about 13.
"Oh my god, is that a diaper, you little baby," said one of them
"Wait you'll do whatever we want?" said the other, "Okay take off your skirt so we can get a nice view!"
I complied and stuck my diaper in front of my webcam.
"Okay now why don't get get back a little so we can get a nice view of your face."
I looked to Shannon for support but she merely nodded a yes, so I once again complied.
"Holy shit it's a guy!" They laughed. "Ok let's see your junk."
I hung my diaper low and showed them my package, with them giggling like little schoolgirls. Suddenly they both began to take pictures with their phones, and when I tried to cover my junk I received a disapproving look from Shannon. It went on like that for another minute before Shannon turned off the laptop, and made me take off her clothes and replace them with my dress. She then sent me on my way. I took my bag and sprinted through the neighborhood, luck fully without anyone seeing me. I got home and prepared for the game waiting for later in the day.

[knightgunner13]

loved it even if it was short and i hope that the girls did not know him from anywere.

[Dareman99]

Awesome story, when is the next part?