~Sleepover of a Lifetime~

[RussianRonaldo]

Okay well this is my first attempt at a story, so I would like brutal honesty from you all. I will honestly try my best as far as grammer and spelling go, and I am writing this story in a first-person point of view, so don;t get angry when you get bombarded with suprises about the non-protagionist. Thank you, and enjoy.
P.S. - I will post the first two chapters (the to shortest) up here without question, if you guys want me to post more I will need to know that someone if reading.

Chapter One- How it Began...

I was sitting in my room quietly, waiting for my sister and her friends to go to bed. I was 15, only one year younger than all of them, but for some reason they all seemed to enjoy bothering me. My sister had three friends over for this sleepover, and even though my mom said I could have friends over, I didn't. To be completely honest, I didn't have many friends. I was really smart, and a sarcastic a**. I was about 5'3, short for a 15 year old, and my dick was an average 6'3 erected. I was an odd half-way through puberty, hairy (black hair to be specific), but with a moderately high-pitched voice. Now no one knows this about me, but I have a diaper fetish. I am kind of a poor 15 year old, what 15 year old isn't poor? My lack of money often caused me to be unable to obtain the diapers to fulfill my fetish, so it often went unnoticed.
So anyway, I was quietly playing some Grand Theft Auto Four in my room, and my sister's hottest friend, Marie de Lamenoni, just walked into my room and sat down next to me. She looked at me and quietly, almost nervously asked ,"Hey J.C., want to play some truth or dare with your me and the rest of the lovely ladies in your sister's room?"
I was shocked, the hottest girl I have ever met had just asked me to play truth or dare, so I guess I had no choice, "Of course I will play", I answered, at which I turned off my game, and followed Marie into my sister's room. When I walked in, my sister immediately ushered me down to a spot in between her and Marie, and began to introduce me to her other two friends, Jamie Pan and Alana Ponce . Now, Marie and my sister had the biggest tits of the group, both with massive double D's. My sister, Alana, and Jamie, just like me, all had black hair, making Marie the only one with a set of blonde hair. Everyone here except for Alana and Marie were A students, both of them being merely C students, nothing too bad or good.
After the introductions were done, Marie looked at me, and with an almost sinister smile on her face asked, "So J.C., truth or dare?"
"First of all, his name is James Copper, don't call him by that dumb nickname", barked my sister, "and secondly, first we all must agree that if someone does not complete a dare, or if they answer a truth incorrectly, they are the other people's dare slave for the night, and since mom and dad are gone for the night, we have the whole house to run or mischief."
Everyone agreed and we re-began the game with me, and, I chose truth, which I later found out was a horrible idea...

Chapter Two- My Horrible Idea

"Okay good we got him early," smiled my sister, "okay James, what would you say your number one fetish is?" Now I have to be completely honest here, I did not know what they meant about getting me early, I thought they were just referring to how it was only 7:45, so I got me to play relatively early in the night. I had absolutely no idea that they knew about my little diaper secret, so I looked at my sister, straight in the face, and lied.
"I have no idea what a fetish is." I answered. My sister looked at Jamie and nodded, and which point Jamie got up and went over to my sister's computer. We all waited in absolute silence as Jamie pulled up a computer program that I did not recognize.
"James, me and Jamie took computer programming together last year, as you know. We developed a program that allows us to monitor another computer's actions without alerting the firewall. After close monitoring of your computer, and all the little diaper fetish sites you go to, I have to say we learned quite a lot about my little brother," my sister looked at me and my heart just stopped. They knew about my fetish I thought, they are going to go right to mom, and I will be screwed. My sister began to speak again, "Now we are not going to go to mom and dad, unless you stop playing with us. Next time you lie or disobey a dare, mom and dad will see all of the actions of your computer in the last couple of months. For right now though, your lie will only be punished with two dares. I dare to strip off all of your clothing, and put only this one," at which point she threw me a diaper that she appeared to pull out of nowhere. I looked at my sister for some show of sympathy, which there was absolutely none of, and I immediately stripped off my clothing, doing it as quickly as possible. It seemed like as soon as my underwear was off, the diaper was one, as to avoid showing the girls my dick, which I knew would not last forever. My sister once again continued to talk, "Okay now our second dare for you: since we know you love diapers so much no more bathroom for you until noon tomorrow. Too east you say? Okay then after I am done explaining this dare, we will give you a 12 pack of soda to drink within the next hour. Now what happens if your diaper begins to leak? Well Marie here happens to have a interest with being a pretend mommy, so she will change you." My sister finished and I just stood there quietly. I had no choice but to agree, which I reluctantly did, and they handed me a 12 pack. It seemed to me like they had planned this out all from the beginning, so I used my turn wisely.
"Amy, truth or dare?" I asked. My sister looked at me, and answered truth, just like I wanted her to. I quickly asked her, "Did you and your friends have this whole thing planned out when you came to get me?".
My sister looked at me, and answer, "Well, since I cannot lie, yes we did, but so what? You are already stuck playing for the night, so that question was almost completely useless. Now Alana, truth or dare?" I was already on my second can of soda as she asked the question, for not only did I love soda but I also was an extremely quick drinker. I felt the diaper ruffling between my legs, and I absolutely love it. My fetish was finally fulfilled. I absolutely, 100% was loving this game so far. It felt so good being in a diaper after all of these years without them.

[Kewai]

It isn't my cup of tea But I am loving it so far I think you should continue, it is reeeaaalllyyy good for a first, you have talent dont waste it

[Difficulty_10]

Fine start. Let's see where it goes.

[RussianRonaldo]

Hey thanks for the replys, but like I said... please, be brutally hponest with me. I want none of that "be nice to the noob" bullcrap. Also, I made an edit to my first ypost, I accidently wrote the wrong point of view... this story is in a first-person point of view. Also, this is entirely fiction, although I do have both a sister and a diaper fetish, and when I was younger I was unable to fufill my fetish.

[RussianRonaldo]

Chapter Three- New Feelings?

Alana looked back at my sister and replied, "Well, I guess I choose dare." With that my sister grinned, and she picked a piece of paper. She wrote something on each side, and then ripped it in half and put the two sheets on either side of her, both face down.
"Well Alana, just so that you don't blame me entirely for which dare you get, I will let you pick one of the two I have written down." Alana looked confused, but in a way confident. She quickly and quietly reached over and picked up the one to the right of my sister.
She began to read, "Strip James of his diaper, then strip yourself of everything and put the diaper on. Once done, you must give James a blowjob until he cums." She stopped reading, "Oh come on Amy you know I hate giving blowjobs!"
"Yeah well don't you think it is time for you to start sometime?" my sister laughed back, "And besides, look how excited it made James." Right when she finished that sentence I realized that my erection was clearly visible through the diaper, it was almost popping out. I turned bright red, and Alana walked over to me and began to take off my diaper. She pulled it off and my cock kind of bounced up. She then stripped off her clothing, which did not help my throbbing erection, and she put on the diaper. Now with the diaper secured on herself, she lowered her head to my penis and began to suck it. Because of the fact that I was already within seconds of cuming, I jizzed almost immediately into her mouth, and after swallowing it, Alana's dare was over. When she stood back up, she saw the soda cans next to me and turned towards my sister, "Amy, where is James going to relieve himself now that I'm wearing his diaper?"
Amy's eyes lit up as she realized the same thing. She looked at me, and smiling, said "Well, I guess our little baby will just have to hold it for the rest of the night, until noon, and if he can't he will just have to take his punishment." Now I knew I was in trouble, I had already drank four cans of soda, and my bladder was close to exploding. The erection only put off the inevitable, but I put this problem out of my mind for now, and just focused on the present.
Alana looked towards Jamie and asked, "Jamie, truth or dare?" Jamie quietly choose truth, and so Alana began to think. "Hmm well Jamie, I guess I want to know what your biggest fantasy is?"
Jamie looked troubled, and after about a minute quietly answered, "I have always wanted to watch a guy get cross dressed, I think it might turn me on or something." Everyone in the room, including me, looked at Jamie completely shocked. I saw my sister and Alana look at each other, and Marie whisper something into Jamie's ear. Jamie, after another minute of silence, looked at Marie and asked, "Truth or Dare?" Marie choose dare and Jamie spared absolutely no time in coming up with her dare, "I dare you to get completely naked until I say otherwise!" Jamie almost shouted. Marie merely shrugged, and got to work. She quickly stripped, and when she was done, did not try to cover anything. Here was the hottest girl I have ever met in my life, and now she was naked sitting next to me, and I was also naked. Before now my erection was about to calm down, but when Marie stripped it popped right back up again, however no one noticed.
Marie, trying probably to divert attention from her naked body, looked at me and asked, "Truth or dare J.C.?" I thought about my situation, and decided that I was having a pretty good time, so I answered dare. She smiled at Jamie and said, "Okay J.C., I dare you to put on all of the clothing I just took off, but go first put on a diaper, so if your bladder does explode, it doesn't do so on my clothing." I just stood up, bladder heavy with urine, and walked over to my sister who handed me a diaper. I put it on, horniness filling up inside of me, and began to put on Marie's clothing. I put on the thong first, which did not really matter because of the diaper I was wearing, and then I hooked on her bra. My sister handed me some toilet paper, and I immediately stuffed the cups of the bra. I looked around and saw that Jamie was definitely getting turned on by this. I lifted up Marie's floral patterned skirt and put it on, and for some reason became aroused. As I put on the matching tight shirt that was supplied, I began to wonder if I enjoyed being cross dressed. I had always been a diaper lover, I knew that, but when did the prospect of wearing women's clothing begin to cross me as sexually arousing? I had no idea, all I knew was that I was now in a diaper and a full set of women's clothing, extremely turned on. Alana was in only a diaper, and Marie was fully naked. I looked back at me sister and began to think how to turn the game in my favor...

[Kewai]

I really like it, It isnt exactly what I am into but it is okay, a bit more description in some parts could be nice, but overall good work.

[italia13calcio]

i honestly love this story. please dont stop!

[MattInPanties]

I love it, mostly since its about my likes/fantasy. Thanks for writing this.

[RussianRonaldo]

Thanks so much for the replys guys! I was going to give up until I saw that you guys liked, or pretended to like, my story! Thank you so much! Well here goes nothing ~

Chapter Four- Point of No Return

"Okay sis truth or dare?" I asked. My sister looked at me, with not even the slightest idea of what I was imagining. I had an idea that would probably turn this game into my favor, and within a couple of rounds cause all of the girls to be naked. My sister chose dare and I replied, "Good, I dare you to turn Marie on using only your tongue. She must have her juices flowing within one minute or there will be a punishment." Right about then is when I started to pee. The worst part was the fact that when I felt my diaper getting full, I had to pull off Marie's skirt and thong. My sister looked at me, about to ask me what the hell I was doing when she realized. Her and her friends broke out laughing.
"Aw the little baby is having an accident isn't he?" my sister mocked, "Well Marie I will do my dare as soon as you change him." She handed Marie a diaper and she walked over to me. She pulled of the diaper, and threw it into the trash can. She then, after wiping me down and applying baby powder, just so that I would smell like a baby and not only look like one, put the new diaper on. I put back on the skirt and thong and she sat back down and my sister walked over to her and got to work with her tongue. Wasting no time, she started the stopwatch and started licking the inside of Marie's vagina. My sister did not even waste time tickling her clit, or trying to get her just to the edge of releasing her juices, she just went right in to get the dare over with. 30 seconds in and Marie was already moaning, meaning that I knew I was going to lose this dare. 12 seconds left and Marie still did not release her juices, and my sister looked like she was getting frustrated. The time limit ended and, against all odds, my sister was unable to get Marie to release her juices.
I looked at my sister, smiling, and said, "Well I guess you lose don't you? Well as your punishment, you must strip Jamie completely, using only your teeth." My sister merely shrugged, and Jamie turned a little bit red. My sister walked over to her friend, and almost like they were in a porno, began to strip Jamie down as sexually as possible using only her teeth. When Jamie only had her bra and thong on, my sister began to moan sexually, and then continued. When Jamie was naked, and I got a view of her sexy body, I knew I was winning this game. Sure I was in a diaper and full set of women's clothing, but I had two of my sister's friends naked, and one of them in only a diaper.
My sister wasted no time after stripping down Jamie, she sat back down asked Alana, "Truth or Dare? Wait... actually guys why don't we make this game more fun. Why don't we get rid of the truth part and just do dares? I honestly don't think anyone who won't do dare should be allowed to play with us. Is this okay with you guys?" After everyone agreed, me more by peer-pressure than by anything else, she went back to Alana and said, "Okay Alana, I dare you to, mostly as revenge for James' dare to me, allow James to suck on your tits until he ejaculates, and if he doesn't within one minute, you must take an enema!" Upon hearing this, both me and Alana turned beet red. Right when my sister said this, I knew Alana would be taking the enema, for as both me and my sister know, it takes me a while to ejaculate when I get hard unless I have been hard for a while, and since I had been hard the whole night, my erection had faded and I knew there was no way she would be able to get me hard. Alana, not knowing this, went right over to me, and started sucking my dick. Even though the blowjob felt extremely good, my dick was barely hard, and I hadn't jizzed by the end of the minute. My sister smiled and led Alana into the bathroom by the shower, slid down her diaper, and poured the enema into her ass. She then, as an extra touch put a butt plug in. "Oh by the way, you will wear this butt plug for about five minutes, just to make sure you have fun with your enema." my sister laughed. She slid the diaper back up and walked her back into the room. They both sat down, and we decided to put the game on hold until Alana's enema was done. My sister played some music for us, and when the five minutes were over, she pulled out the plug. About 30 seconds after the plug was out and the diaper was pulled back on, Alana began to involuntarily crap herself. Although I usually did not find this kind of stuff funny, I did laugh hysterically at this. When Alana's bowels were done empting, she went into my bathroom to clean up and put on a new diaper.
Alana walked back in with a clean diaper, and sat back down. She looked at Jamie and told her the dare, "I dare you to have sex with James!" The whole room went absolutely silent as everyone thought about the dare. My mind, and I am sure Jamie's, was racing. I was a full-fledged virgin, but I knew that my sister and her friends weren't. I of course wanted to finally have the chance to lose my virginity, but I did not know if Jamie would do it or not. I only knew one thing at this point, this night was never going to be forgotten, and that this was the point of no return...

[italia13calcio]

i still love it! interesting to see wheter jamie will do it or not

[Kewai]

I love this story, it isnt exactly what I would expect myself to read but I still like it.

I can't wait for the next chapter!

[RussianRonaldo]

Thank you so much for the replys once again! I decided to do my next update to the story today, just because I had some time to kill. So everyone, let's say hello to Scotty-

Chapter Five- A Cop, a Friend, and Some Photos

"Oh okay if you insist. Prepare for a good time little baby girl James." smirked Jamie, "Someone's about to lose her virginity" Obviously taunting the fact that I was both cross dressed and in a diaper, I didn't know if I wanted to lose my virginity to her. I mean, I knew that I had no choice, but I always thought that this moment would be different, I thought it would be with someone I had actually felt something towards. I looked and Jamie and merely nodded, and since she was already naked she didn't need to strip. I began to take off Marie's old clothes and the diaper, and I walked over to Jamie. My sister took a condom out of her purse (why did she have one in there!?) and threw it over to me. I quickly put it on, and laid down next to Jamie on the floor.
She immediately grabbed me by my shoulders, pulled me over, and began to make out with me. She put her tongue into my mouth, and with one her hands she began to stroke my dick. My dick, even though it had been through extreme torture the past hour or so, immediately prang up from all of these stimulations. Not knowing what to do, I began to feel her up, and I turned onto my back. I put her on top of me and began to poorly hump her. Probably feeling like my virgin instincts were not good enough, Jamie began to guide me into the right direction, and after about 10 minutes she threw me off of her and laughed, "Well I hope during his next time he won't perform as badly." I walked back to my seat and quietly put on my diaper and Marie's old clothing. I sat down and looked back over at Jamie right as she looked over at Marie. "Marie, your dare is a rather public one. Alana broke the barrier with the sex dare, so I dare you to walk around this block as you are right now, naked" Marie looked shocked and began to blush.
"Bu... but..." Marie started, "What is I get in trouble? You have to know about the public nudity laws!?"
Jamie merely laughed, "Well isn't that too bad for you?" Marie looked to all of us for support, but no one spoke out. We all got dressed in normal clothing except for me and Marie, and walked outside. We started to walk around the two mile long block, with everyone about 20 feet behind Marie. We all were talking loudly trying to get people to look at us, except for me and Marie, and since it was only about 10 some people were still outside. People would turn to look at us, realize what they were seeing, and turn back quickly. One lady was so offended she went immediately inside. About half way through the walk we heard a siren, and that's when we realized that the lady had called the cops! Public nudity is strictly prohibited in our town, and Marie was breaking that law! We started to sprint back towards the house, but soon the siren was right behind us. WE stopped running and soon the cop car pulled up next to us. The police officer got out and looked at us, especially naked Marie and obviously cross dressed me.
"Um what is going here?" asked the cop. We all looked at each other, until I quickly answered him, explaining all about our game of Truth or Dare, and that this was merely a dare. "Oh, well I can't deny that I did crazy things like this when I was your age, just from now on please try to stay inside with your dares." the cop said. He then got back into his car and drove away.
Everyone started to thank me for my quick reaction time, keeping us out of trouble. We walked back to the house, and everyone took off their clothing, except my sister we lost none of it in the game so far, and we sat back down. Marie was still beet red as she looked at me and explained the dare, "Okay J.C., I dare you to invite Scotty over to play with us, and you must answer the door the way you are dressed right now!" I looked at her and merely groaned. I knew that there was so escaping this, and I just called up Scotty, my best friend since 1st grade. He was about my height, also smart, with blonde hair. I one time saw his dick accidently, so I knew that it was around the same size as mine. I asked him to come over, and after some convincing he said he would be over in a minute or two. I heard my doorbell ring and I went over to it, ready to be embarrassed.
"Hey Scotty" I said, "Please don't ask about my outfit, my sister, her friends, and I are playing Truth or Dare, and this is all part of one elaborate dare."
Scotty looked back at me, and answered, "Oh cool, I'll play, just promise me that you got at least one of them naked." I love Scotty for this reason, he was open to almost anything. We walked back into my sister's room, Scotty's jaw dropping at the sight of everyone. He sat down in between me and my sister, and after a couple introductions, the game continued.
"Okay Scotty," I said, "I dare you to let my sister and her friends give you a full makeover!" Once again, Scotty merely shrugged while my sister and her friends got right to work. They stripped him of all his clothing, and began to put makeup on him. They applied pink lip gloss, pink nail polish, eye shadow, and some mascara. They then got to work with his clothing, putting him into a bright pink thong, a stuffed pink D-bra, and, instead of the skirt/shirt combo I got, an ankle-length pink, puffy dress. I had to say that at this point, my friend actually looked, except for his hair, like a complete women. They all sat back down, when I had an idea. I quickly, while no one was looking, took out my phone and began to snap photos of all of them. I put my phone away and waited for the game to resume...

[Kewai]

I like it, Keep up the awsome work!

[italia13calcio]

amazing... very few grammar error and a great plot. do u have any previous stories?

[RussianRonaldo]

No and thanks so much for the feedback! I just which other people besides you two would comment on it 0_0