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Document: My Awesome Baby-sitter

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Author: Ron

My Awesome Baby-sitter

Author: Ron

Summary: Ian is a fairly typical nine year old boy, even though he has a bit of a mischievous side that comes out sometimes. His baby-sitter Sandy, who is now in college, has been baby-sitting him since he was a baby. What looked to be another normal evening of baby-sitting for Ian turns out to be quite different due to Ian's sudden feelings toward wearing diapers again. Ian may just get the chance to revisit his past and go through an evening of "baby"-sitting.

“IAN, GET UP AND GET READY FOR SCHOOL!”

I woke up with a start. I had been having a dream in which I was an actual baby wearing a diaper and sleeping in a crib, but now, I was in neither a crib, a diaper, nor the body of a baby. Instead, I awoke in the same bed that I went to sleep in the night before, my pajamas and my normal nine year old body. It was another one of those stupid early school mornings, and my mom was yelling at me to get up.

Realizing that it was no use trying to avoid getting out of bed, I slowly rolled out of bed, grumbling at how I hated school. My dream had been kinda weird, but I couldn’t help but miss it now that it was over. I couldn’t even remember it that much, except that I was really small and that I was really happy during it, which could not be said for my state now that I was awake.

Well, at least this was Friday, so I’d get a couple of days to forget everything we would do during the school day. I groggily changed into a T-shirt and jeans before taking a quick look in the mirror. There I was, my somewhat skinny self, with my brown hair miraculously still in place after waking up (it came down past my ears all the way around my head except for my eyes since I wanted to be able to actually see during the day). After throwing on my socks and tennis shoes, I plodded down the stairs to the kitchen.

As my mom and dad ate their breakfast and drank their coffee, I put some Frosted Flakes and milk into a bowl and began eating, still having trouble keeping my eyes open. It was a rainy day out, and it was early enough that it still looked pretty dark outside. As I crunched my cereal, I remembered that it was Friday, and I tried to make the most of it.

“Hey mom,” I said. “Can I have Brian over tonight? It’s not a school night.” Brian and I had been best friends since I can remember, and we had gone over to each other’s houses so many times we both practically had two addresses.

“Have you forgotten already Ian?” my mom asked me. “I told you that your father and I are going out to a movie tonight, and Sandy is going to come over to baby-sit you tonight.”

“And taking care of one little monster is all we’re going to ask Sandy to do, I don’t want to double her stress level by making her watch both you and Brian,” my dad added.

‘Oh, that’s right,’ I thought, since (like always) I had forgotten what mom had told me. Hey, I’ve got other really, really important things to be remembering. Anyway, since dad was exaggerating me and Brian’s behavior I felt I had to say something.

“Hey, Sandy loves coming over. I’m her favorite kid!” I retorted.

“Mmm, right,” my dad said. “I personally don’t know how she puts up with you sometimes. Well, if you behave yourself tonight, then the next time we’ll see if Sandy will agree to watching both of you. But knowing your little actions as of late, I don’t know if that will happen.” He gave me this little “dad” look as he said the last part.

I don’t know what he was talking about. It had been like, two months since I had done something bad. Ok, maybe it was one week, but you get what I’m saying. Either way, I still felt pretty good. I always had a fun time when Sandy came over ‘cause unlike all the girls at school, Sandy was actually a girl who was cool.

Sandy had been taking care of me ever since I was a baby. I think she was around thirteen when she started baby-sitting me, and now she was like, in college, but since her college was really close to her house, she still lived there and still baby-sat me for some extra money. Anyway, she was kind of pretty, but she was really athletic, too. She always liked doing fun stuff, like playing soccer, going roller skating, and playing video games. She even took karate! The other girls that I knew (who all went to school with me) liked to do stupid things like play with dolls and you know, other girl stuff.

As I got my backpack and went to the bus stop, I felt better knowing that no matter how bad school was that day, I’d at least have a pretty good time that night.

Even though the day dragged, I did get to see Brian and a couple of the other boys who were in my class, and it was eventually over. I spent a couple of hours at home watching TV and playing on my PlayStation 2, and then around 5:30, I heard a car pull-up. I went downstairs to our door to go see Sandy as soon as she walked in.

As the person who dropped her off drove away, I saw her walking toward the house. She was wearing a white blouse and a pair of somewhat tight jeans, and her long brown hair blew a little bit in the soft breeze. But something was different about her; she was carrying something over her shoulder. As she got a little closer, I noticed it was one of those baby bags that people carry all the baby’s stuff in.

The thought that jumped into my mind immediately was that the baby bag was for me. I mean, why else would she have it? I started to get kinda panicked; I thought mom had told Sandy that since I had been bad recently that I should be treated like a baby. I really started to panic as she came closer and my heart began to pound in my chest as I got a picture in my head of my mom and dad holding me down while Sandy took out a baby diaper and taped it on me (although I will admit that for some reason I was kinda excited about the idea as well, even though I didn’t know why).

Without thinking I ran out to Sandy as I felt a lump starting to form in my throat. As I ran up she said “Hey kiddo, how are you? Ready to have some fun tonight?” (at the moment I was positive that she was referring to treating me like a baby).

Immediately my voice turned strangely whiny as I eyed the bag and begged her, “Sandy, please, please don’t dress me like a baby! I’ll be good, I swear. I won’t give you any trouble….”

I was cut off by Sandy bursting into a laugh. She had to cup one hand over her mouth to try to stop herself? What, did she find the idea of treating me like a little baby funny?

Before either of us could say anything, my mom came out the door and began to speak. “Hello, Sandy! Hey, what’s so funny?”

As Sandy finally stifled her laugh, she said “Ian, you silly kid! This diaper bag isn’t for you! I had to baby-sit another family’s baby before I came over here, silly!”

I felt myself go pink as my mom started to laugh too. As I took in what she said I realized how extremely stupid I had just been and I felt like hitting myself in the head very hard.

As my mom calmed herself, she asked Sandy, “What, the Thompsons’ boy? I didn’t know he was still in diapers.”

“Well, they wanted to potty train him, but he’s having trouble, so they decided not to push him. These are Pampers size 6 that I’ve got in the bag. I bought this bag since I baby-sit a few babies in the neighborhood anyway, and they just told me I can keep some of his diapers in here so I don’t have to hunt for them in their house.”

“Wow those are pretty big diapers!” my mom said. “I bet those might even be able to fit Ian!”

“Mom!” I said indignantly as Sandy laughed slightly. It was bad enough that she had to say things like that at all, but it was even worse in front of Sandy, especially after what I had just said earlier.

“Well, it’s not like we would have found out before, since little man here was potty trained real early,” Sandy said as she gestured towards me (Little man was a nickname that Sandy had called me since I could remember).

“That is true,” mom said. “But I know you yourself have changed plenty of Ian’s poopy diapers in the past, Sandy!” she added with a laugh.

“MOM!” I said again as I felt myself blush even more. “Do you have to say stuff like that?” I don’t know why she always felt she had to do that.

“Oh come on Ian,” Sandy said. “Your mom’s just kiddin’. Besides, you were such a cute little baby that I never minded changing your poopy diapers! In fact, I still think you’re kinda cute.” With the last line she got me in a headlock and gave me a soft noogie.

“Hey, cut it out!” I said, but this time I was smiling. What she said didn’t really comfort me, but I always liked it when Sandy played around with me like that.

Anyway, a few minutes later, mom and dad had gone, and Sandy and I went in the house, “diaper bag” (as mom and Sandy called the baby bag) included.

“Alright, Ian,” Sandy said. “Your parents want us to stay here tonight, so I’m gonna go order a pizza. Why don’t you head on into the living room and decide what you want to do tonight? Oh yeah, and take the diaper bag with you. If it’s in the living room I’ll be less likely to forget it.”

“Alright,” I said, feeling very funny as I took the diaper bag turned and walked into the living room. After I put it down against the wall, I decided to plop down on the couch and flipping on the TV. As I watched, I couldn’t make myself think about what I wanted to do that night; my mind kept on drifting over what had just happened with mom and Sandy outside. As I eyed the diaper bag, various images kept on entering my mind; Sandy saying how she used to change my diapers, mom mentioning that those size 6 pampers could probably fit me, my imaginary image of me being forced into a diaper by Sandy again…

The more I thought about it, the more I began to fantasize about wearing a diaper again. I knew it was pretty silly; I was nine years old after all, and everyone knew that diapers were only for babies. I mean, everyone I knew would have died laughing if they saw anyone my age wearing a baby diaper. But despite this, I couldn’t help but be filled with a desire to see what it would feel like to wear a diaper again. Suddenly, I remembered parts of the dream that I had had that morning. Soon, I was picturing myself lying down on my back, Sandy leaning over me with a diaper in her hand. In my mind, she remarked how I was such a cute little baby, and then before I knew it, I had a diaper taped snugly around my waist.

But it wasn’t just wearing a diaper that was so intriguing to me. To make things even weirder, I had a desire to wet a diaper too. I just really wanted to know what it would feel like to just be able to let loose and feel the warm pee up against my legs and crotch. I could picture Sandy saying “Did my little baby Ian go pee pee in his diapy? Alright, kiddo, let’s get that diaper changed…”

Sandy suddenly entered the room, and she startled me a bit as I was shaken out of my fantasy. She asked me if I what I wanted to do as she sat down, and she seemed to be surprised that I didn’t have an answer.

“You’re sure acting funny tonight, Ian,” she said. “First you burst out and think I brought a diaper bag for you, then you jump when I enter the room, and now you can’t think of anything to do when normally your head is bursting with ideas.”

“Uh, well, it was kinda, uh, a hard day at school,” I said, forcing myself to keep my eyes away from the diaper bag leaning up against the wall.

This seemed to satisfy her, though. We started watching TV and after a while the pizza arrived and we ate while we watched. Things seemed to be finally getting back on a normal track again. That is, until something unexpected began a turn of events that would lead to a very interesting evening.

“My Awesome Babysitter” Part 2

After we finished our pizza and the drinks we had, we just continued to watch TV. Had we decided to turn off the TV right then, the evening probably would have just been normal. But this was not the case because during one of the commercial breaks, a diaper commercial just happened to appear on the screen.

Although the commercial was pretty simple, it had a pretty powerful affect on me. The mother in the commercial gave so much attention and love to the baby as she changed his diaper. In addition, the speaker in the commercial kept referring to how soft the diapers were, and they placed special emphasis as to how stretchy their diapers were. I myself had never actually been around babies, so I didn’t know much about what it was like to be around diapers. However, the commercial seemed to draw me back to the time when I was a baby, and the diapers still seemed somewhat familiar. As much as I tried to seem uninterested, I couldn’t keep myself from watching every second of the commercial very deeply and intently.

I don’t know if Sandy actually noticed this or not, but it may very well have been the reason that she decided to say something.

“Wow, it’s amazing how far products have come!” she said. “Those diapers look like they could hold a lot. The stretchiness of those diapers looks pretty incredible, too. The ones you used to wear weren’t nearly that flexible. I bet these new ones would not only fit a baby well, but they might fit you now, Ian!” She even gave a small chuckle with this line.

She then laughed again and said “I wouldn’t even be surprised if they fit me!”

I still don’t know exactly why I didn’t just laugh along with her and let the topic rest after that. I guess it was the affect the commercial had on me, the appeal of the statements she had just made, or that darn diaper back leaning up against the wall that I just couldn’t keep my eyes from drifting to. Whatever it was, I just couldn’t stop myself from pressing the topic even more; the desire to wear a diaper again just kept popping up in my mind.

“Yeah, I guess it would be pretty neat to be able to put on a diaper again!” I said with a laugh of my own.

Somehow I knew right after I said it that I may have gone too far. Although she was still smiling, Sandy stopped laughing when I said this. She raised an eyebrow as she looked at me and asked, “Uh, why do you say that, Ian? Wouldn’t it be kinda weird for a nine year old like you or a 21 year old like me to be seen with a diaper on?”

“Uh, right, of course,” I said as I nervously laughed. “It would be pretty stupid. I mean, uh, I haven’t wanted to wear diapers since I was a baby. I mean, uh, I haven’t worn diapers since I was a baby, and uh, I don’t want to now or anything. It’s stupid.” With this, I turned back toward the TV, trying not to look at Sandy. I felt myself start to go red again and I knew that she was still looking at me.

“Uh, right, whatever you say, Ian,” she said. I could tell she was still laughing a little and even though she turned back toward the TV, there was a bit of a weird tension between us as we started watching TV again.

A few minutes passed with neither of us saying a word, but then she began to speak again.

“Well, you know, Ian,” she said as she turned toward me again. I looked at her and she continued by saying “I do have some diapers with me tonight.” She nodded toward the diaper bag. “They’re pretty big, I bet they’d fit you no problem. No one would ever know, and you could see what it would be like to wear one again.”

Without thinking, I excitedly said “Really?!”

“Aha!” Sandy said. “I knew that’s what you wanted tonight!”

“No!” I responded. “No, I was just kidding. I mean, diapers, like, they’re for babies, right? Why would I wanna wear one?” However, I was very nervous as I said this, and my voice sounded kinda funny as my body tensed a little.

“Come on, Ian,” she said, obviously looking past what I had just told her. “You’ve been acting funny ever since you saw that diaper bag. You can’t fool me. I know you like to look like you’re a rambunctious little ball of boy energy, but you can’t help but get excited at the idea of being put into a diaper again.”

“No, really, I mean it!” I said, although I convinced neither her nor myself. “That’s crazy!”

“Well, maybe a closer look might make you reveal you’re true feelings.” With that, she strode over to the diaper bag, reached inside it, and pulled out one of the size 6 Pampers that she had told mom about. As she brought it over, I could tell she had been right; even though I knew nothing about diapers, I could tell that it would fit me no problem.

She sat down and unfolded it a little, making sure to keep it up close to by body. She even grabbed my hand and made me feel the plastic cover.

As this was happening, a new wave of excitement washed over me. I was pretty sure that the last time that I had actually touched a diaper was when I wore them as a toddler, and the sight, touch, and especially smell of it made my body tingle with excitement.

Sandy apparently noticed something in my reaction, because she looked me right in the eye and then said, “See? I knew it. Come on Ian, I won’t laugh, and I definitely won’t tell anyone. You can tell me. Truly, honestly, would you like to wear diapers again?”

There was something about the way she spoke that made me feel that I couldn’t help but trust her. I was really embarrassed about telling her that this is what I so badly wanted, but the look on her face was so sincere that I decided to just take the plunge and be honest.

“Well, I…..uh, well, yeah,” I said. “It’s just….I don’t know, I just think it would be really neat to put one on again.”

“Well, what are we waiting for?” she asked. She got up, still holding the diaper in one hand, and beckoned me over with her other hand. “Let’s go get you diapered right now!”

Somehow this isn’t quite what I had expected. “Wait a sec…don’t you find this the slightest bit weird? I mean, I’m assuming you haven’t had the experience of diapering many nine-year olds.”

“Well, I have to admit, I can’t say I know many people who want to wear diapers that don’t need them. But so what, you gotta try new things, right? I was scared to try bungee-jumping, but that was a great experience! I doubt putting a diaper on a nine-year old will be that big of a deal.”

This made me feel much better about the whole idea. If Sandy didn’t think I was crazy for wanting this, then it wouldn’t be so bad. As a grin spread across my face, I excitedly said “Alright, let’s do it!” I then bolted past her and raced up the stairs to my room.

Although this caught Sandy off guard, she quickly chased after me. I heard her yell, “Whoa, slow down little man! Wait for me!”

I stopped once I got into my room so I could catch my breath, but right after I got there, Sandy appeared in the doorway. She dropped the diaper on the floor, ran over to me, and playfully threw me down onto my bed. I smiled as she continued to wrestle with me, holding me down while I tried to escape her hold on me. She then smiled and said “Calm down, little man! You gotta lie still if I’m gonna get you into a diaper!”

As I my laughter calmed down, Sandy went over to get the diaper and threw it onto my bed next to me. “I’m tellin’ you,” she said. “This reminds me of when you were a toddler. It was quite a job wrestling you into your diapers every time I had to change you!”

This statement made me turn a little pink, but I had to admit that the image of Sandy struggling to put a hold my toddler self down in order to change my diaper was kinda funny.

“Alright, I just want you to relax and let me handle everything,” she told me. I tried to do this despite my sheer excitement of being put into a diaper again. Sandy left my shirt on but rolled it up so that my stomach and chest were visible. She then undid my jeans and slid them down my legs and off of my ankles. I felt pretty awkward, but I forced myself to stay relaxed. As she was doing this, it seemed as though Sandy was somewhat pleased to be doing this whole thing.

“Hey Sandy,” I said. “It seems like you’re enjoying this as much as I am!”

“Well,” she responded. “Like I said, even if you don’t wanna hear it, you are a pretty cute kid. And I just think you’d look even cuter wearing a diaper! Besides, it’s like a bit of nostalgia for me; I’ve seen you grow from a baby to a kid these past years, and it’s kind of nice to see you looking, well, like a baby again.”

She then grabbed my underwear and proceeded to pull them off as well. As she did this, I automatically covered up my privates with my hands, feeling myself go completely red at the same time.

Sandy giggled when she saw this and just calmly said “Oh Ian, relax, it’s nothing that I haven’t seen before. Remember, this isn’t the first time that I’ve put a diaper on you!”

This was pretty much just cold comfort to me, but realizing that I would have to be naked before Sandy could put a diaper on me, I slowly let my arms relax at my sides while Sandy finished taking off my underwear.

Sandy then reached for the diaper next to me. As she unfolded it in front of my face, she said “Alright, little man, one diapered bottom coming right up!”

“My Awesome Babysitter” Part 3

I was still relaxing my body, but I have to admit that it felt pretty funny because Sandy then grabbed both of my ankles in one of her hands and lifted my legs up. I expected her to comment on getting a clear view of my naked butt in her face, but she said nothing as she slid the diaper underneath my raised butt. She lowered me down, and before I knew it, she was already pulling the diaper up over my waist.

Although I still felt somewhat embarrassed about the whole thing, I couldn’t keep myself from watching what Sandy was doing. Sandy obviously knew how to change diapers well, because it took her no time at all to pull the sides of the diaper around my hips and tape up both sides so that it fit me perfectly. The feeling of the diaper around my waist was interesting; I have to admit that it felt funny, but it felt oddly familiar and very pleasing at the same time. The soft and snug feel of the diaper was very comforting, and somehow feeling the soft material up against my skin made me feel…safe.

Once I felt it was on, I sat up and looked down at my diapered self to get a better feel for it. It fit perfectly; in fact, from my viewpoint, my lower half looked just like the babies that I had seen in those diaper commercials. The idea excited me greatly, especially since it was combined with the soft and secure feeling of the diaper up against my skin. I couldn’t help but simply look at Sandy, smile and say “These feel…well, really nice!”

“I knew you’d like it!” she said. “Here, get a better look!” she added as she grabbed me by the wrist and led me over to the mirror in my room.

As I looked at my reflection, I was somewhat awestruck. I lifted up my shirt so that I could get the full view. The upper half of my body looked just like it always did, with my brown hair coming down around the sides of my head and my light blue Myrtle Beach shirt looking just as normal as ever. But from my belly button down, I looked just like a toddler. My diaper had a slight bulge in the back, and the cartoon designs on the front of it clearly made me feel little. Despite the fact that I still felt a little silly and embarrassed, I still found my reflection somewhat cute.

Anyway, I still loved the feeling and look of the diaper, and I felt like I never wanted to take it off. Before I could take in more about my diaper, Sandy picked me up, placed an arm around me, and walked out the room carrying me on her hip (I was pretty light, I guess, plus like I said, Sandy was pretty athletic).

“Come on, little man, let’s go back downstairs.” Although I was caught off guard when she did this, I didn’t object. I had no desire to put my pants back on, I was happy in only my diaper and shirt. Besides, it had been a while since Sandy had picked me up and carried me like this, and to be honest, I kinda missed it.

Sandy put me back down on the couch downstairs, and then said, “How ‘bout a little music, little man? You like rock music, right?”

“You bet I do!” I said.

She went over and flipped the radio on to the most popular rock station in our town. I had recently really gotten into listening to music, and I liked rock the best. I didn’t really know the bands, but I liked a lot of the songs that I heard on the radio. Immediately I listened up, and they were playing one of my favorite songs. I got up from the couch and got into the song. Before we knew it, both me and Sandy were singing along with the music. We even danced and did a little air guitar. I was having a blast and the fact that I was wearing a diaper even slipped from my mind.

Well, until Sandy suddenly stopped in the middle of another song, that is. She apparently got a case of the giggles and couldn’t stop laughing.

“What?” I asked giving her a puzzling look.

“I’m sorry, Ian, but I just realized, you used look just like you did when you were a toddler. You used to do the exact same thing; you’d get up and dance to music in just your shirt and your diaper with a big smile on your face. And everyone watching would always say how adorable you looked and laugh. And it is true, you do look just adorable dancing around in your diaper.”

I felt myself really start to blush when she said this. For some reason, I didn’t want to be wearing a diaper anymore. I just felt like a little baby and was very embarrassed at the idea of everyone laughing at me dance around in a diaper. I went over to the couch and sat down, a big frown spread across my face.

“Hey, Ian…” Sandy began, but I didn’t want to hear it. I was nine years old, I wasn’t a baby anymore, and I didn’t want to have anyone remarking about how cute I looked in diapers. The more I thought about how I had these desires to wear diapers, the more I was bothered by it.

“Come on, little man,” she said. “I didn’t mean anything by it…”

I felt tears beginning to form in my eyes. “I’m not a baby!” I told her. “I don’t need diapers! I don’t wanna be the cute little baby that everyone thinks is helpless and needs diapers! I’m nine years old, and…”

Sandy put her arms around me and began to hug me. “Oh Ian, I know that,” she said. “I know you’re not two anymore. I know you’re a big boy now, and I don’t have to change you diapers anymore.”

“So why do I like this?” I asked her. “Why did I want to put on a diaper tonight?”

“Well, I don’t know exactly, Ian,” she said. “But you know what? It doesn’t matter. I know, I know I keep telling you how cute you look, but you’re still nine, even if you do like the idea of wearing diapers. But so what? I don’t think it’s a bad thing. I mean, I know tons of old people who forget what it’s like to be young anymore, and let me tell you, they’re no fun at all, they’re just completely boring. You’re still really young, but at least you can find happiness in remembering what it was like when you were younger. Most people just forget all of the things about them when they were toddlers, and you haven’t yet. And I think that’s pretty darn cool, personally.”

“Really?” I asked.

“Yeah,” she said. “You did beat me in soccer last week, remember? And you’re a pretty tough fighter, even if you are wearing a diaper,” she added with a grin.

“Yeah!” I said. I then felt something; I had to pee. Automatically, I got up to go the bathroom.

“Hey, where are you going?” Sandy asked.

“To the bathroom,” I replied, not giving it a second thought.

“Now wait a minute,” she said, as she grabbed my arm. “What exactly do you think that thing around your waist is for?”

I suddenly remembered my diaper and felt kinda funny. “Wait, you don’t expect me to uh, you know…uh, in my, in my…”

“Yes, your diaper,” she said. “Come on Ian, put up your dukes!” she said and she lunged at me and playfully tackled me to the ground.

My automatic response was to fight back. “Oh, you’re on now!” I said as I began to smile and pummel her with my fists.

But then she started to tickle me, and I’ve always been real ticklish. I was helpless to stop her, no matter how fast I tried to move my hands. Even worse, the pressure on my bladder had increased greatly, and I didn’t know how much longer I could hold it in.

“S..Sandy!” I said between giggles. “You…you’re gonna m…make me, p..p..pee myself!”

“That’s the idea, silly!” she remarked. “Come on, little man, I wanna see you go pee pee in your diapy!”

I was laughing so hard that I didn’t even get embarrassed by this comment. Instead, my body just gave way; before I knew it, I started peeing without any ability to stop it.

But the diaper did it’s job; instead of me feeling my pee trickle down my legs, I felt my private area and my thighs get warm and moist as my bladder emptied. To my surprise, it was the best feeling in the world; my laughter combined with the warm feeling made me feel extremely happy, and even any embarrassment I had about wetting myself didn’t make me feel bad at all.

Somehow Sandy could tell that I had done it, because she stopped tickling me. “There, that wasn’t so bad now, was it?” she asked as my laughter died down.

Even though I was a little embarrassed to admit it, I told her that it actually felt pretty good. She apparently didn’t think this was weird because she just gave a small laugh and then changed the subject.

“Well, you know what, little man, it’s gettin’ pretty late, and your parents will be home soon. And they’ll kill me if they see that you’re still up. So back upstairs you go!”

She picked me up again and carried me back up to my room. She again told me to just lay down on the bed and relax. She then left and came back with a damp washcloth.

Although I didn’t really want to take off my wet diaper, I knew I had no choice, so I gave no objection as Sandy un-taped it and took it off. She then began to wash my private area with the washcloth, and yet again, my natural reaction made me pull away from her.

“Oh, come on now, Ian,” she said with a smile. “I can’t send you to bed dirty like this, and I know I can clean you off faster than you can.”

“Oh, all right then,” I said resentfully. However, even though I wouldn’t admit it to her, it felt amazingly good to have her wash me down there.

She gave me my underwear and pajamas. She then told me to put them on, brush my teeth, and get in bed. Although I would normally protest to these commands given my mischievous nature, I was tired out from our activities and didn’t feel like arguing. As I did this, I saw Sandy put my wet diaper into the diaper bag, and she carried it downstairs. By the time that she was back, I had already dressed and brushed my teeth. She decided to tuck me in, and she kissed me on the forehead as she whispered “I had fun tonight. And no matter how big you get, you’ll always me my ‘little man’. And I know you’ll never forget I’m still the one who can change your diapers.”

I thought maybe I would have been embarrassed by this, but I wasn’t; I actually just felt so special that I couldn’t think of anything to say back. I laid there thinking about the evening as Sandy went turned off the light and left the room.

“My Awesome Babysitter” Part 4

Throughout the rest of the weekend I thought a lot about what had happened when Sandy had come over. I could hardly believe that Sandy had actually diapered me, and on top of that, I actually wet it. It was so amazing that I couldn’t help but get excited when Mom told me that Sandy would be baby-sitting for me again the next Friday. And for the first time ever, when Mom asked if I wanted to have Brian over that night (I had been good for Sandy, and that was the deal, right?), I told her no. As much as I liked Brian, the thought of being diapered again was too exciting.

The week dragged on even more than it normally did, and by the time Friday rolled around I was bursting with excitement. I was not let down, because there Sandy was again with the diaper bag around her shoulder. Sandy even explained to Mom that she would probably have the diaper bag with her for the next few weeks because she was still baby-sitting the kid being potty trained (good cover story on her part).

It actually was kinda awkward when my parents left that night. I hadn’t seen Sandy for the first time in a week, so there was a weird tension between our normal routine and the fact that last week had been very different, what with me being diapered and all. As much as I wanted to jump right back into where we left off the week before, I had trouble telling Sandy that I wanted her to diaper me again.

“So, little man,” she said. “What’s up?” (it was weird, she said this almost as if the previous week had never happened).

“Uh, not much,” I responded. “It’s been kind of a boring week.”

“I wish I was you,” she said. “Not only have I had a ton of schoolwork, but me and Chad have been having some issues.” (Chad was her boyfriend).

Even though my mind kept thinking about diapers, I listened to what she had to say. However, at the end, I couldn’t contain myself any longer, so I took the plunge.

“Uh, Sandy?” I asked. “Do you think, you know, if you don’t mind, could you, uh, I mean…”

“Let me guess,” she said with a small laugh. “You want me to put you in another diaper, right?”

“Well, yeah,” I admitted with a shy sort of smile.

“Ok then kiddo,” she said with a smile of her own. “I thought that would be what you wanted. Luckily, I came prepared, and I might just have some surprises for you. Well, if you don’t mind the floor, why don’t we just take care of business right here in the living room?”

“Oh! Yeah, that’d be great!” I said.

“Alright, since I don’t want to make a mess on the carpet, take off your pants and lie down on this changing pad.”

She took out this little mat thing and put it on the ground. I felt kinda weird getting naked again, but not as weird as the week before. As I took off my pants and underwear, I saw Sandy take out a diaper and a couple of other things.

I lay down on the pad feeling weird but also very excited. Sandy didn’t unfold the size 6 Pamper right away; instead, she first took this small bottle that said “Baby Lotion” on it.

“Ok, now this might feel a little weird, but babies should have lotion on them before they’re diapered.”

Noticing the look on my face, she then said, “Oh come on Ian, I know you’re not really a baby. But if I’m gonna diaper you, we’re gonna have to do it MY way, ok?

I nodded my head even though I wasn’t crazy about the idea. I was beginning to feel more and more like a baby again. On the other hand, part of me liked this idea.

It was definitely pretty weird having Sandy put the baby lotion in her hand and massage it into my private area as well as my butt. But I knew that this is what she did to the babies whose diapers she changed, and plus it felt pretty good.

She then took out a little canister of baby powder. “I don’t want my little man to get a diaper rash, now do I?” she said with a sly little grin. As she lifted my legs up and shook the baby powder on my butt I felt a great sense of joy; the baby powder smelled wonderful and I got another little jolt of excitement as I was reminded even more of when I was a baby.

Sandy then took the diaper and slid it underneath my butt. She lowered me onto it, sprinkled some more baby powder onto my front, and before I knew it, had fastened the diaper around my waist snugly. As I got up, I felt extremely happy and well, cute, just like a baby.

As Sandy put away the baby supplies, she beckoned me over to the couch and patted it, telling me to sit down.

After I did so, Sandy looked at me seriously and began to speak. “Ok, Ian, listen up, because this is serious. Last week gave me a few ideas, and to be honest, I find you absolutely adorable in your diapers. But since I’ll probably never get this chance again, and because I like you, I want your full cooperation tonight. The deal is, you do what I say, no questions asked. If you refuse, I’ll tell your parents all about you wearing diapers again, and I’ll act like you took them and wore them on your own.”

She saw the shocked look on my face, and then said, “I know Ian, but I really don’t want to have to do that. All I ask is your full and total cooperation. If you don’t want to do this, tell me now, and I’ll take that diaper off of you and we’ll have a ‘normal’ evening. Otherwise, the deal is on. So what do you say?”

I have to admit I was kinda confused about all of this. What did Sandy have in store, and why was it so serious to her? I was definitely a little surprised as well, so I needed a chance to think about it. As cool as Sandy was, I didn’t doubt for one second that she’d tell my parents I had taken the diapers on my own, and they’d no doubt believe her given my past actions. I was kinda nervous about giving Sandy complete control of me. But my diaper felt so good that I didn’t want to take it off. And besides, it was Sandy, and I trusted her.

“Ok,” I said. “I’ll do it. You have full control.”

“Excellent!” she said. “Alright Ian, remember, full cooperation, no ‘buts’. But don’t worry, if it really gets to be too much for you, just yell ‘Stop!’, and the diaper goes off and the evening will be normal. Got it?”

“Got it,” I said, feeling good that I had a way out, but feeling nervous that things could get so bad I’d need to yell stop.

“Alright then, let’s start by changing your clothes. Don’t worry,” she said seeing the look on my face. “That diaper isn’t going anywhere until it needs to be changed into a new one. However, I want you to take off your shirt.”

As I did this, I saw her pull an article of clothing out of the diaper bag: it was one of those one-piece set of pajamas for babies, which I later learned was called a footed sleeper. However, it was bigger than one for a baby; in fact, it looked just the right size for me.

This definitely surprised me. I mean, diapers were one thing, but now Sandy wanted me to wear baby clothes as well? Why was she so intent on this, and what was the point?

I didn’t have much more time to ponder it, however, since Sandy then told me to lay down again and relax. As I laid down in just my diaper, she told me to let her do all of the work, so I continued to relax as she began to put me in the sleeper. I felt kind of silly and even more like an actual baby, but our deal was still fresh in my mind, so I made no objection. And after Sandy zipped it up, I had to admit, I actually liked the feel of it. It made me feel warm on both the outside and the inside. I felt a smile go across my face as I imagined being little again, especially since I could feel the padding on my feet as well.

Before I knew it, Sandy had scooped me up in her arms and carried me, well, like a baby across to the couch. My legs were across one of her arms and my back over the other. As she sat down, she used one arm to support my head and I felt my body resting in her lap. I still felt a little funny but I was very comfortable as well.

While still holding me, I saw her reach into the diaper bag and pull out a baby bottle full of milk. She was still supporting my head with one arm and used the other hand to move the nipple of the bottle toward my mouth. As it came close, I pushed it away and said, “Hey! I don’t wanna drink from a bottle like a little baby!”

“Ah ah ah, Ian,” she responded. “Don’t forget our deal. I’m in control here. And stop talking. Remember, babies don’t talk.”

“Wha…” I began to say, but I was cut off as she pushed the nipple into my mouth. But I remembered our deal and just began to quietly suck from it. It was just normal milk, and even though it was hard to get out at first, I actually began to enjoy it. It was very relaxing, and I began to feel very warm and cozy as I felt the warm cloth over my body, Sandy’s soft body that I was lying in, and the soft padding of my diaper on my butt.

I closed my eyes as I continued to nurse from the bottle, and I began to imagine myself as a real baby again. The feelings that I felt were so real and before I knew it I felt joy wash over my body. This was enhanced even more because Sandy begin to talk baby talk to me, saying things like “Now that’s a good wittle baby. Drink da whole bottle like a good boy!” This was wonderful, and at that moment I didn’t want to be anywhere else.

Eventually, the bottle ran out, and Sandy took it out of my mouth. I opened my eyes and saw her reach down and pinch my cheek saying, “Oh, little Ian, you’re just adorable.” I felt a smile go across my face as she said this.

My stomach felt a little funny, but before I could say anything, Sandy already knew what to do. Before I knew it, she stood up, put me over her shoulder and began to pat my back. Soon after, I felt the taste of milk in my mouth as I let out a burp. Sandy had just burped me!

She then shifted me over to her hip. She reached into the diaper bag once again and this time she pulled out a pacifier. She popped it into my mouth, which for some reason I didn’t object to at all and began to suck happily. She laid me down on the couch and I felt myself relax, allowing all of my baby feelings to just soak in.

Sandy then pulled out a little stuffed teddy bear and told me to hold it. I did so, and instead of feeling embarrassed or weird, I was just reminded of when I was little and used to carry around stuffed animals all of the time.

As I lay there, Sandy sat down next to me and began to softly run her fingers through my hair. This soothed me even more, and by the look on her face, Sandy was enjoying it as well.

I then realized that I needed to pee. Remembering that I was diapered and how good it felt last time, with only a little effort I managed to get a little trickle going. Soon, I had completely let myself go and felt the warm moisture up against my legs and waist as my diaper filled.

Sandy must have been an expert baby-sitter, because she already began to notice. “Uh-oh,” she said in a babyish voice. “Looks like someone has a wet dydee! We better get him changed!”

With that she lifted me off of the couch and back onto the changing mat. I was still sucking my pacifier and clutching my bear. I simply continued to relax as I felt Sandy undo my sleeper and remove my wet diaper. I got a little shock as I felt something cold touch my private area; Sandy had begun to clean me with a baby wipe! Within a short period of time Sandy had cleaned my entire butt and private area, and after quickly applying some more powder, she taped a new diaper on me and fastened my sleeper back up.

Afterwards, she told me to sit up and take out my pacifier. She then began to speak.

“So, what do you think?”

“Wow!” I told her. “This is amazing! Kinda weird at first. And I do feel a little silly to be sucking a pacifier and drinking from a bottle, but it feels….well…nice.”

“I thought you’d like it,” she said. “But you see, I don’t think it would be as good if I didn’t have control of you like that. It wouldn’t be as real.”

As I began to think about it, what she said was true. With Sandy in control of me, I didn’t have a care in the world, just like a real baby.

“Well,” she said. “Our time’s just about up, little man. Time for you to go to bed.”

Sandy then helped me out of my sleeper and my diaper, and she put up all of the baby stuff as I changed back into my normal clothes. As the evening ended, I began to think about mom’s offer of having Brian over. My mischevious mind began to work, and suddenly my head was filled with an idea for my good buddy.

“Hey Sandy,” I said. “How’s about next week you baby-sitting me AND Brian…

“My Awesome Babysitter” Part 5

Turns out things would be even more interesting than I had originally thought. Mom told me that the next Friday night that she and dad would actually be spending the night away, and Sandy had agreed to sleep at our house and watch me until Saturday evening. When I asked mom if it would be all right if Brian came over too, she gave in and said that it would fine as long as it was fine with Sandy (hey, for two weeks in a row I had been good for Sandy, right?) I offered to call Sandy and ask her, and mom agreed. I thought a bit more about what Sandy and I could do with Brian, I called Sandy and let her know about my plans. I was a little surprised; not only was Sandy fine with all of my ideas, she was actually pretty excited about them. I don’t know, maybe Sandy had found a new love for diapering nine year olds or something.

Anyway, I talked to Brian about him coming over and spending the night that Friday, and like usual, he was happy to come over.

“Yeah, that sounds cool,” he said. “Sandy’s always been cool when I’ve gone over there in the past, even when we weren’t really good for her. Oh yeah, are you up for maybe pulling another trick on her? It would be all in fun, she wouldn’t get mad.”

“Oh, I think a trick this weekend would be a great idea,” I said. I never said who the trick would be played on, however.

Friday night came, and Brian just rode the school bus and got off on my stop. We actually had some fun before Sandy got there, playing around on the computer and my PlayStation 2. And even when Sandy got there, the evening played out normally. My plans for Brian would take place the next morning, and even we were having so much fun with her that he never even brought up wanting to play a joke on her.

When it was time to go to bed, after we got in bed, Sandy got the ball rolling for what we were going to do.

“Ok Brian,” she said. “I just want to make sure. You’re not a bed-wetter, are you?” (she had never watched him overnight, so it was a fair question).

He looked a little embarrassed to be asked this, and immediately responded by saying, “What? No! Of course not!”

“It’s ok,” she said. “If you are, it’s nothing to be embarrassed about. I just want to know.”

“No, really, I’m not!” he said, looking even more uncomfortable. I knew he didn’t wet the bed, but if someone asked me, I would have felt weird too.

“Ok, that’s fine. But I’m not washing wet sheets, so if I find out in the morning that you’re lying, there’s gonna be a big problem, ok?”

“Honestly,” he said. “I’m not a bed-wetter. It’s not gonna happen.”

“Ok. Well, good night, boys.”

With that, she left the room. Me and Brian started talking, and he asked, “What’s with her?”

“Well,” I said. “She just wants to make sure. She asked me the same thing the first night she watched me. And since you don’t wet the bed, you don’t need to think anything else about it.”

Ok, before I go into what we actually did to Brian, you might read it and think it’s pretty mean. But hey, he had embarrassed me at school a few weeks ago, claiming he didn’t mean anything by it and that it was all in good fun. Well, this was just my way of getting him back, and it was also all in good fun.

Anyway, after we talked a bit more, we got tired and fell asleep. However, about 8 o’clock the next morning, I felt Sandy wake me up. She had used an alarm clock to get up, and she told me to keep quiet so I wouldn’t wake Brian up. She had with her a bowl of warm water.

We didn’t bother with the whole dipping the hand in warm water gag. Instead, being very careful, Sandy lifted up Brian’s blanket and lightly poured the water over Brian’s crotch. Luckily he didn’t wake up. As we both giggled, she told me to pretend I was asleep and get ready because she would be coming in to wake us up.

As I lay back down and closed my eyes, I heard Sandy leave and then come back in and yell “Alright, boys, I know it’s Saturday, but you gotta get up!”

As I acted like I had just gotten up, I felt Sandy yank my blanket off of me (I had slept on the floor and given Brian my bed). I gave a fake yawn as I looked over at Brian, who still held his own blanket tightly so that he didn’t have to get up.

“Ok, Brian, you too,” she said. She continued to speak as she pulled his blanket off to. “Come on, if we have to get up…” she paused as she looked down at the wet spot around his crotch and on the sheets. I looked at her face and saw a look of puzzlement, almost disgust.

Brian then looked down at the wet spot and a look of complete shock crossed over his face. He opened his mouth but no sound came out, and he looked at Sandy, then me, and then back at the wet spot.

“BRIAN!” Sandy yelled. “You TOLD me you were not a bed wetter!” I began to see some anger in her face.

“But…but…I’m not!” Brian said. His voice was shaky and I could tell he was embarrassed.

“I can’t believe it!” she said. “Well, I have washed too many wet sheets in the past, and if you’re going to lie to me, I’m just going to have to punish you for it!”

“No, really,” he started to say. He actually sounded like he was about to cry. “I didn’t mean to…”

But Sandy would not have it. “I told you there would be a big problem if I found a wet bed. So you’re just going to have to face the consequences, Brian. Ian, you come with me, and if you don’t do as I say, you’ll face the same punishment as Brian.”

Her voice was dead serious, and then she turned and left. I gave Brian a nervous glance and said “Dude, you never told me you were a bed wetter.”

Brian looked really upset and said “But I’m not! I’m telling you, I don’t wet the bed!”

“Well,” I said. “This is the one thing Sandy is really, really serious about. I’m sorry, but I’m can’t disobey her, she’s too mad. I’ll have to do what she tells me.”

Brian looked a little scared now as he realized even I wasn’t on his side. I then left the room and talked with Sandy.

Even though we knew we were being mean, we laughed a little about what had just happened. She asked me if I was ok with going on with it, and even though I felt bad for making Brian upset like this, I remembered very well how badly he had embarrassed me before, so I decided that I still wanted to mess with him some more. What I still couldn’t believe is that Brian actually believed that he had wet the bed; I guess it had happened so fast that he didn’t realized that it was water and not pee on his crotch.

Anyway, as Sandy got ready, I went back into the room where Brian was. Looking nervous, I said, “I’m sorry, Brian, but I’ve got to help Sandy punish you. If I don’t she’ll punish me, too. So, I just have to say…sorry”

Brian looked even more nervous, and I think he wanted to try and leave the room. But at that moment Sandy entered. She closed the door, and then said, “Well, considering the clothes you’re wearing now are a mess, we’ll have to take them off. So take off all of your clothes right now unless you want ME to take them off.”

Brian just merely said “No way! I don’t have any other ones, and I’m not getting naked here!”

But Sandy said, “Don’t worry about your other ‘clothes’. But if you won’t take your clothes off, I guess I’ll have to. Ian, get over here and help me.”

With that, Brian tried to make a break for it, but Sandy simply caught hold of his wrist and pulled him towards her. While she held him in place, I first removed his shirt, then his wet pants. As Sandy held him in his underwear, she remarked, “Well, since you’re not cooperating, I’ll just have to have Ian tie you down.”

Brian struggled as hard as he could, with a look of mixed anger, fear, and helplessness on his face. But Sandy held him still, and I took a piece of rope that I had had in my room and tied one of his wrists to the head of my bed. I did the same with his other wrist. I tried to make it look like I didn’t really want to do it. Sandy then let go of him, and we both looked at him trapped on my bed.

Realizing how he could now do nothing, Brian looked like he was about to cry. “What are you going to do to me?” he asked weakly.

“Don’t worry, little Brian,” Sandy said as she took off his underwear. “Your punishment will simply be fitting. If you’re going to wet the bed, we’ll just have to make it so that this will not be a problem anymore. Come on Ian, let’s get ready.”

As we walked out of the room, Sandy and I just smiled at each other. Call me a horrible friend, but I kind of enjoyed taking control of Brian. I knew at the end of it all we’d just tell him it was a joke, and for now, payback was all I wanted.

“Ok, Ian, last chance to back out,” Sandy said. I told her that I still wanted to go on with it, so she picked the diaper bag that had our supplies in it.

Sandy and I went back into my room. Brian didn’t really have any response to the diaper bag; well, until Sandy pulled out a size 6 Pampers diaper, that is. It took a few seconds for Brian to register what it was, but once he did, a new look of fear crossed his face.

“NO!” he yelled. “I’m not going to wear a diaper! No, no, no, no! Someone help! She’s going to put a diaper on me!”

“Geez, Brian, calm down,” Sandy said as she began to unfold the diaper. “It’s not like anyone can hear you anyway, and I’d rather not have to gag you.”

When Brain heard the word “gag” he seemed to calm down. However, as Sandy unfolded the diaper completely and started to walk towards him, his reaction went from anger to pleading.

“Please,” he said, tears now in his eyes. “Please, please, please don’t put that diaper on me. I’m not a baby!”

“Well, you did go pee pee on yourself last night, and since babies do too, they need diapers. So, since you acted like a baby, I’m going to treat you like one. I am a “baby” sitter, after all.”

Brian then began to kick his legs furiously, but Sandy grabbed both of his ankles in one hand (admittedly, Brian wasn’t the biggest kid). She asked me for a towel, and after I handed it to her, she put it underneath him. She then asked me for the baby powder, and I gave it to her, again trying to look like I was sorry for Brian.

I could see him sobbing now as Sandy began to powder his butt and crotch area. The smell of the baby powder filled the room, and funnily enough, the twitching of Brian’s struggling body made him look even more like a real baby. I even began to feel genuinely sorry for him, but I had decided that I wouldn’t back down now.

Next, Sandy placed the diaper underneath Brian. She pulled down his legs over it, pulled it between his legs, and tightly taped both the sides around his waist.

“There,” she said, dusting her hands off. “That diaper will make sure that the baby doesn’t make any more messes on the sheets. But we don’t want ‘baby’ Bwian to be hungry, now do we? You just wait, sweetie, Sandy will get you all fixed up.”

Sandy then left me in the room with Brian. There he was, lying on the bed with tears running down his cheeks, diapered just as much as he was when he was a baby.

Through his tears he said, “Ian, please, I’m begging you, make her stop! I don’t want to wear a diaper…I’m not a baby!”

But I just sadly shook my head and told him that I had no choice. Soon after, Sandy came back in, now with a baby bottle full of milk in one hand. This made matters even worse for Brian, and he then begged her not to make him drink it.

Sandy, however, would have none of it, and before either me or Brian knew it, she had shoved the bottle into his mouth. As he was forced to drink it, the tears continued to pour down his face, and Sandy just made it worse for him by condescendingly cooing him and saying things like “Good baby, drink your whole bottle.”

Once he had finished the whole thing, she took it out of his mouth and put it aside. Then, to my surprise, she just busted out laughing. Realizing that the joke was now over, I myself began to giggle. I mean, Brian really had looked kind of funny wearing a diaper and being bottle-fed.

As we laughed, Brian look confused, but still embarrassed and as he sobbed, he asked, “What, you guys think this is funny? Putting a…a diaper on me, and…”

“No, no, Brian, you don’t get it,” Sandy said between laughs. “This whole thing was a joke that Ian and I came up with!”

“That’s right,” I said as I began to untie him from the bed. “You didn’t really wet the bed, we just poured some water on you. And I just wanted to get you back from when you embarrassed me so bad a while back. I was trying to think of the best way, and I remembered that Sandy always had some diapers…”

I suddenly remembered that I couldn’t tell Brian about me wearing diapers. “…for one of the babies that she takes care of. We came up with the idea of Sandy being really angry with you for wetting the bed and forcing you into a diaper.”

As I finished untying Brian, he took all of this in. Relief spread over his face as he realized that Sandy didn’t really think she needed to baby him. Once he fully took it in, he then got mad at me.

“You jerk!” he said. “How could you do this to me?! To your best friend?”

“Hey man,” I replied. “Don’t forget how horrible I felt after you embarrassed me last time!”

Unfortunately, this didn’t solve the problem, and he was still very angry at me. I didn’t know what to do; I hadn’t expected him to be this mad, and I began to feel bad about what we had done.

Sandy sensed the tension between the two of us, but thankfully, she had an idea. Without warning and to my great surprise (and Brian’s), she grabbed me and pinned me to the floor.

“Ok Ian,” she said, her face about an inch away from mine. “Your turn! Brian, get me another diaper!”

I saw an evil grin spread over Brian’s face as he now realized it was my turn to be diapered. After the extreme humiliation he had gone through, this would be sweet revenge for him. As he turned away, Sandy smiled at me and whispered, “Come on, Ian, play along, this is your chance to be diapered while Brian is over, and it will make him feel a lot better. He’ll never know you like it if you act like you don’t!”

Realizing her logic, I calmed down a bit. Even though I was kind of embarrassed to be diapered in front of Brian, I was also really excited because I didn’t think that I would get the chance to wear a diaper this weekend. Plus I couldn’t think of any other way to make him calm down. However, I knew that I couldn’t let Brian realize that I liked it, so I tried to look horrified as I saw him come over with the diaper.

Sandy instructed Brian to take my clothes off. I kind of put up a fake struggle, and I even falsely begged Sandy and Brian not to do it. But then the inevitable happened…Sandy powdered my butt and before I knew it I was in a diaper again. Brian was clearly enjoying himself and even joined Sandy in baby-talking me while she did her work.

Sandy even went the extra mile with me; not only was did I have to drink from the bottle, but Sandy carried me like a baby while I sucked on a pacifier. They even tickled me and “forced” me to wet my diaper. Even though this surprised Brian, he loved it and used it as a great opportunity to say things like “Aww, wittle Ian wet his diapy and needs a change!”

The logic behind all of this was beautiful. Although I admit it was hard to act like I was humiliated (because I was so happy), I loved every second of my baby treatment. I even think the fact that Brian joined in treating me like a baby made it even better. But he was having a ball making fun of me, too. Funnily enough, even though he thought he and Sandy were playing a joke on me, in reality, we were playing a joke on him, considering only the two of us knew that I was loving my babyish state.

However, the joke could only last so long. Sandy put the game to an end, and after I got out of my diaper, I could tell Brian was much happier. He had forgiven me for what Sandy and I had done. We then both just laughed at ourselves and how funny we had looked in diapers.

Soon it was about time for my parents to be back. Sandy made us swear that we wouldn’t tell anyone about what had happened this weekend (not that we wanted to anyway). She then said “Bye bye my cute little baby boys,” as she left us. Right after my parents walked in and had a brief talk with Sandy. She then left, and it was time for Brian to go too. After they had both gone, I just relaxed and thought about everything that had happened that day.

Oh yeah, just in case you’re wondering what Brian had done to embarrass me so badly, there’s no way I’m telling you. If you think being forced into a diaper is bad, you have no idea the humiliation I suffered from Brian’s previous stunt.

“My Awesome Babysitter” Part 6

After Brian and I had our crazy baby-sitting experience, the week-end was soon over and I was off to school again for the week. I couldn’t bring myself to mention anything about it to Brian, and he must have felt the same way because he carried on as if the whole thing had never happened.

I was fine with this at first; we still were “normal” friends, and we continued to have a good time with each other and our other friends at school.

The problem was that Sandy wouldn’t be coming over again for a long time; she was really busy with her schoolwork among other things, and the few times my parents decided to go out over the next six weeks, they just had me stay over at Brian’s or another friend’s house.

This wasn’t a big deal at first, but after the first couple of weeks, I started going through diaper withdrawal. I couldn’t stop thinking about how happy I had been wearing and wetting diapers, and I even liked the thought of seeing Brian in one. My desire became continually strong, and it got to the point that I had trouble concentrating in school (which led to a couple of occasions of me looking completely stupid because our teacher would ask a question and I would be completely clueless as to what she was talking about). I began to feel like I was going crazy.

What made it that much worse is that I had no one to talk to about it. I wasn’t able to get a hold of Sandy, and other than her, no one knew that I had worn a diaper since I was a baby.

Except…Brian. But the fact that he never mentioned anything about it clearly showed that he was not interested at all. He might have even forgotten that the whole thing even happened. The idea of me even mentioning diapers again was weird, and for me to tell him that I actually enjoyed wearing them was simply preposterous.

On the other hand, I felt that if I didn’t tell anyone about it, I would explode. I began to picture in my mind how I would tell him and how he would respond. I wondered if he would think I was really weird or stupid. I wondered if he would tell anyone else. Most importantly I wondered if he would still be my friend.

After giving it much thought, I finally decided that I would tell him. We had been best friends for so long that I felt I could tell him anything, and I trusted him enough not to tell anyone.

Since I would be going over to his house again the upcoming week-end, I decided that would be the best time to tell him. I thought about it a lot that week, and I was very nervous and afraid that he’d laugh at me or think I was really weird. Still, I stayed resolved to it, and realized that I couldn’t back out.

Once that Friday evening came, I waited until after we had finished having dinner with his family to tell him. As we walked up the stairs to his room, I started feeling slightly sick to my stomach as I began building up my courage to tell him.

As we got into his room and threw ourselves down on the floor, he noticed that I looked kinda funny.

“Ian, are you ok? You look a little sick or something.”

I took a deep breathe in and said, “Look, Brian, I got something I have to tell you.”

Not thinking it was a big deal, he said, “Ok…go ahead.”

“No, it’s really really serious,” I told him. “You have to swear that you won’t EVER tell ONE single person about it.”

He paused for a second and looked very interested in what I had to say. A couple of seconds later he said, “All right, I swear, I won’t tell anybody. We’re best friends, remember?”

As I remembered that he was indeed my best friend, I took another deep breathe, and said, “Ok, here goes. Remember about a month ago when you came over to my house, and Sandy was baby-sitting us…”

As he recalled what happened, he smiled a little and said, “Oh yeah…ha ha, wow, that crazy girl actually put diapers on us! Pretty embarrassing, huh? I tried to make myself forget about it, but I still remember how scared I was and how funny it felt to wear a diaper again.”

Feeling a knot beginning to form in my throat, I nervously continued. “That’s the thing,” I said. “You know when she put the diaper on me? Well, that wasn’t the first time that I had worn a diaper.”

“Of course it wasn’t, doofus,” Brian said to me with a smile. “You wore them when you were a baby. I did too. Everyone does. I think I even slightly remember back when we were in diapers.”

“No, no, that’s not what I mean,” I said, feeling my nerves reach a peak. “I actually wore one a few weeks before you came over. Sandy put one on me.”

“Wow, I never knew you wet the bed, Ian.”

“No, you still don’t understand. I don’t NEED them, for bedwetting or anything. I, well, I…LIKE wearing them.”

As I saw his mouth drop, I felt it would be easier if I just kept talking. Before I knew it, I began blurting out all my feelings about diapers and being treated like a baby. Brian simply didn’t say anything and looked like he was having trouble breathing as his jaw dropped and I launched into the story of how I had seen Sandy’s diaper bag, how she had offered to diaper me, how I had loved it so much, and how the next week she had proceeded to treat me like a baby. As I continued, the knot in my throat became tighter and tighter and I felt more and more queasy. Brian’s look of shock did not wear off, and I noticed my voice was very strained and nervous. By the end, I even noticed that I had tears in my eyes.

“…and that’s where we got the idea to pull a joke on you and put a diaper on you. Sandy surprised me when she decided to diaper me, but I was faking when I acted like I didn’t like it. I simply LOVED it, even though I still don’t get why.”

As I finished, Brian just continued to look at me in disbelief. He opened his mouth to say something, but then closed it again.

Not knowing what else to say, I just blurted out, “Yeah, I know, it’s really stupid and weird and you probably think I’m a freak, but you don’t understand, I’ve been thinking about this for weeks and weeks and I just had to tell some…”

But Brian then cut me off, and to my great surprise I noticed that he had tears in his eyes. “Ian, I just simply don’t believe it.”

‘Here it comes,’ I thought. ‘He’s going to lay it on me and say he doesn’t want to be friends any more.

But I soon realized that they were tears of joy, because he said, “I never expected this. IAN, I FEEL THE EXACT SAME WAY! When Sandy powdered and diapered me, I was embarrassed, but a part of me just loved the whole experience. I loved the smell of the baby powder and the soft feel of the diaper. I even loved the helplessness of being tied down. But I didn’t want you guys to know, so I acted really mad about the whole thing. But ever since then, it’s all that I’ve been able to think about. But I could never tell you. You’d just think that I was dumb.”

Not believing my ears, the nervousness simply drained from my body and a wide smile went across my face. It was at that point that I knew that Brian and I would be best friends for life. But it got even better, because Brian then said,

“My desires got so bad that I couldn’t take it anymore. I rode my bike to the grocery store and bought a pack of Pampers Size 6. I was really nervous about it, but I was able to sneak them home without my parents noticing. I’ve been wearing them every night and I’ve even wet them! And getting rid of them isn’t a problem; I just put them in the garbage can outside and the garbage man takes them away every morning. It’s the best thing ever!”

With that, he got up and locked his door. He then went over to his closet. After he rummaged through it for a few seconds, he emerged with an opened pack of size 6 Pampers diapers.

Excitedly I jumped up and said, “Well what are we waiting for?”

A broad smile spread across his face and he said, “Ok, but me first!”

He quickly took off all of his clothes while I got a diaper out of the pack and unfolded it. We had seen each other naked before, so it wasn’t really that weird to see him naked. It was weird, however, for me to diaper my best friend. Being an only child, I had never diapered anyone, so it was new to me. But I soon figured out how, and just like that I had taped up Brian’s diaper and said, “There! All done, mister!”

It was quite a sight. Brian always did look kind of young, what with his straight blond hair, skinny body, and blue eyes. To be honest, he actually looked a lot like a real toddler as he lay there in his diaper.

“Ok, now let me do you,” he said with a smile. Within minutes I had stripped as well and he diapered me. He even gave me a playful pat on my diapered butt and said “There you go kiddo!” (hey, it’s not that weird, football players do it all the time, right?)

We continued to play around in our diapers. We first acted like babies for a bit, and when that got old, we watched a movie in his room. His parents came up to check on us at one point, but we simply put our other clothes on over our diapers and his parents never knew. Part way through the movie, I had to pee, so I naturally decided to go in my diaper (Wow, I even thought peeing in my diaper was natural). After I let go, I told Brian about it.

He looked at me and said, “Well, I guess we better change baby Ian into a new didee!”

I just laughed, put on a babyish voice and said, “Uncle Bwian, will you pwease change me?” I then smiled at him and put my thumb in my mouth.

“Sure thing!” he said. I kept my thumb in mouth as he changed me into a fresh diaper, hiding the wet one in his closet.

After I was changed, I noticed that he was wet as well, and I said, “Uh-oh, looks like someone else had an accident in his diapy, too!”

He just sheepishly smiled and said, “Me go pee pee! Need a new diapy! Waaaaaa!”

As I laughed I had him lie down and changed him into a new diaper too. Unfortunately, we heard his mom coming, and after putting our clothes back on over our diapers, she came in and told us that it was time for bed. As we got ready for bed, we decided to keep our diapers on. As I fell asleep that night, I couldn’t think of a time in my life where I had been happier.

I didn’t get much of a chance to talk to Brian the next morning before I had to go, and since we didn’t want to arouse any suspicion, we decided not to mention anything else about the diapers.

Over the next few weeks Brian and I were extremely careful about talking about our new common interest. Thankfully we got another chance to have fun in our diapers, and I even gave Brian some money to buy a couple of baby things like a baby bottle and a pacifier. I found an old teddy bear and baby blanket to take over to his house, too. We had a very good time.

Thankfully (and somewhat surprisingly), no one ever found out about all of this. And once Sandy’s schedule lightened up, we convinced our parents to let her baby-sit both of us again on many occasions. She was shocked but delighted when she learned about how Brian liked diapers and being treated like a baby, and we had many fun evenings being babied by her.

And the greatest thing about it was that Sandy always gave a good report about our behavior, which meant that our parents trusted us more, and we got even more opportunities for Sandy to baby-sit us (hey, it gave them more opportunities to get away from us little monsters). But they were always surprised to hear that two kids who usually were the most troublesome ones on the block actually behaved and were “as peaceful as good little babies” when ever Sandy took care of us.

The end.