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.”