“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.