“A Bedwetter’s Diaper Story” is my favorite one, so I thought I’d write a spin-off. (Please keep in mind--this is my first story.)
Overview: Leah meets Bobby, the boy she’ll be babysitting for a week. She originally has fun humiliating him, but then that darn conscience of hers starts to change her mind.
The poor kid was wearing at least two or three thick cloth diapers, frilly white plastic panties, and a pale purple dress with more lace than a Victoria’s Secret warehouse. This was my aunt Jennifer’s best friend’s son, Bobby. I couldn’t stop laughing; I almost felt sorry for him, but then auntie explained why he was dressed that way.
It was a result of what had become known as the “panty incident.” Last summer, he sneaked into her room and started masturbating in her panties. Although it’s hilarious and sad at the same time, I thought full-time baby punishment was a little harsh. I mean, he’s fifteen now! He’s bound to masturbate at least once in a while. I expressed these sympathetic thoughts to my aunt, and she informed me that he faces a paddling any time he “plays” with his diapers.
I sat in the living room while aunt Jennifer and Bobby’s mom went over the rules. (The two were going on a cruise and I was asked to baby-sit the little brat; you’d think I’d have something better to do than change a sissy’s diapers, but the pay is great! I guess the nanny got fired or something.)
“Okay Leah, we’ll be gone for about a week. I left you enough money for pizza or something, but my baby boy is only allowed to eat baby food. Bobby can be a little rambunctious sometimes, but I’m sure you’ll keep him in line. Now remember, your aunt and I trust your judgment. If you think he needs a spanking, you can give him the paddling of his life. I just ask that you change his diapers often; my little sissy has very sensitive skin and diaper rash will make him very cranky!” Bobby lowered his head in shame as his mom stood over him, ridiculing her son like nobody’s business.
“You are to do exactly as Leah says. Do you understand me, sissy?” my aunt said. Bobby meekly nodded as the two women left. The second they pulled out of the driveway, I pushed the boy down and made him land flat on the seat of his diaper.
“What are you doing?!” he demanded, angrily. I smacked his thigh; there would be no confusion about who’s in charge. I slipped two fingers in the leg opening of his plastic panties and explained to him that I was checking his diapers.
“Can’t I just tell you if I’m wet?”
“Sorry, sweetie. If a fifteen-year-old boy isn’t responsible enough to use the potty, he’s not responsible enough to tell nanny when he needs his diapers changed. And I should probably warn you… I have free reign over you. If you piss me off enough, I will take you out in public whenever I feel like it, and be assured that you will wear your most humiliating attire.” I said with a sly smile. Bobby again lowered his head, a position all too familiar.
I didn’t really mean what I said—sure, I’d take him out in public, but I'd just be following orders. He subjects himself to enough humiliation, and I didn’t see a point to furthering it. I also didn’t see a point to a daily enema. I found enemas to be far more work than changing the occasional messy diaper.
“All right, my boy. Let’s get you ready for dinner.” I yanked him up off the couch and ordered him into his highchair. (I’m trying to empathize—but this is just too much fun! I have a mixed relationship with him, I guess. I’ll slap him around like other people do, but I want to be a little nicer about it.) After strapping him in and securing his arms with baby reigns, I tied a plain pink bib around his neck.
“Tonight we have mashed peas and carrots. And if you’re a good boy, you can have strained peaches for dessert.” I saw Bobby cringe, and when I looked at the substance I was about to feed him, I couldn’t help but cringe, too. I was ordered to slip diuretics in his food every now and then, and I followed said orders. Yeah, it’d be more diapers for me, but I thought I shouldn’t defy too many expectations.
“Open up, baby boy!” I said, enthusiastically. I fed him that nutritious slop as fast as I could and let it get all over his face. The poor kid looked really ashamed, to which I responded, “Don’t worry, sweetie. All babies are messy eaters.” After wiping his face clean and letting him out of his highchair, he asked me if he could watch TV.
“Sorry, Bobby. Your mommy and aunt Jennifer specifically told me no TV for you. I know! It’s a nice night. How about after I change your diapers, we go outside for a little while?” I saw his eyes widen and well up with tears.
I grabbed him by the wrist and dragged him Aunt Jennifer’s room and told him to lie down on the changing pad. He meekly abided and held still while I pulled his plastic panties down. I unpinned all three diapers, each one way more wet than the previous. After cleaning him with a baby wipe and applying lots of baby powder, I tightly pinned two thick diapers on him. I selected white nursery print plastic panties and with some wrestling, I fit them over the diapers and tucked in any protruding material. After throwing his wet diapers into the makeshift diaper pail, I yanked Bobby up off the floor and asked him to wait for me in the living room.
I gathered some of that Gerber cereal stuff, a few bottles of warm milk, extra diapers, and other paraphernalia and put them into the sissy’s diaper bag. As I was looking in the mirror, re-tying my bandana/headband, I heard plastic crinkling. I crept over to the door and saw Bobby on the couch, stroking the front of his diapers. I heard him letting out pathetic little whimpers, and I struggled to keep from laughing. I know he was forbidden to masturbate, but this was really, really funny. I went back into aunt Jennifer’s room and continued packing, waiting for the little brat to climax.
“Are we ready?” Bobby was terrified, and I assured him that no one would care. We were in a relatively unfamiliar neighborhood; he hadn’t been there since last summer. Even if I did care, there wasn’t much I could do about it. I opened the door and dragged him outside. The neighbors were out enjoying the day, and when they saw Bobby, they enjoyed it even more. Some tried not to laugh, and others howled with no restraint. The boy was about to cry, and I told him not to worry. We walked down the street, and I walked with a little hop in my step; I figured I’d have enough confidence for the both of us. We walked to the local ice cream parlor and I ordered a hot fudge sundae and asked Bobby to save a seat. He hurried over to a spot in the corner and tried to shield his face and embarrassing diapers at the same time. When my sundae was ready, I joined him at the table.
“How did you end up like this anyway?” I asked, even though I already knew the answer.
“…I got caught…masturbating…in aunt Jennifer’s pink panties,” he stammered out.
“Why would you want to wear women’s panties?”
“They looked comfortable. I was curious.” He said, shyly.
“Okay, so you wanted to wear women’s panties. I’ve seen worse. But why diapers?
“I was a bedwetter when I was younger. I stopped for a while, and then I started again. My mom was really mean about it, and she sent me to aunt Jennifer’s over the summer. That’s when… well, you know. She wanted to punish me and I wet that night and I guess it just stuck,” he said, trying not to cry.
“That’s pretty harsh.” Bobby looked at me strangely. I guess that was the first time anyone even came close to empathizing with him. I pretty much inhaled my sundae and, while maturely yelling “Kobe!” I threw the plastic cup into the trash without getting up. I got up and sat back down next to the sissy and checked his diapers. They were pretty damp, so I knew I had to get him home to change him soon. (I wasn’t about to use a public restroom—gross.)
On our way home, we passed through the park. We encountered a few good-looking girls sitting on the bench. As fate would have it, I went to high school with them. Let’s just say we weren’t friends.
“Leah! I haven’t seen you since graduation! Who’s this charming little boy?”
“Hey, Alyssa. This is Bobby. I’m babysitting.”
“Isn’t he just darling?” The baby cringed as Alyssa’s friend pinched his cheek.
“Hey, knock it off,” I said as I saw one of the girls purposely displaying her cleavage. She smirked at me.
“It’s pretty sad that skanks like you get their kicks from trying to seduce fifteen-year-old boys. Must be a real confidence-booster.” I couldn’t believe what was pouring out of my mouth. Was I really defending that sissy?
After exchanging some words that were far too inappropriate for a sissy to hear, I stormed off, dragging Bobby behind me. On our way home, a lot of people saw him and laughed hysterically. He started to cry, and I slipped a pacifier in his mouth to shut him up. I told him that I had my orders and I really couldn’t do anything about it. He meekly nodded and we got home. I unlocked the door and told him to wait in aunt Jennifer’s room.
Perhaps that was a stupid request. I heard drawers opening, and I looked through the door and saw Bobby ogling my aunt’s lingerie. I really wanted to laugh, but I stopped just to see what he’d do. He picked up a pair of pink panties and started furiously rubbing his diapers. When he was about to climax, I burst in.
“What do you think you’re doing, little boy?” He looked at me in horror, unable to speak. Although I was pretty vexed with him, just looking at panties is better than trying them on. “You know you’re forbidden to masturbate in your diapers! I don’t have much of a choice, boyo. I have to listen to your mommy and Aunt Jennifer. I have to spank you.” I ripped his plastic panties and diapers off and tossed his skinny frame over my knee. I reached for the paddle sitting on Aunt Jennifer’s nightstand and started swinging with no mercy. I ignored his pleas as I spanked and spanked and spanked. After less than two minutes, he was sobbing and begging me to stop. I did and cradled him in my arms in an attempt to soothe him.
“Come on, sweetie. Leah needs to get you back into some nice, fluffy diapers.” I led him over to the changing mat and he lied down right away. I told him to flip onto his stomach. After cleaning him, I applied an ample amount of diaper rash cream and baby powder. I flipped him back over with ease and pinned three thick diapers on him. I selected his plain white oversized plastic panties to accommodate the mass of fabric around his legs.
“It’s 7:00, my boy. It’s time for bed, but first I want you to wash your diapers. Just put them in the washer and we’ll dry them tomorrow.” Bobby stood up and went to tend to his laundry, wearing only diapers and plastic panties. I thought I’d skip on the nightie—it was pretty warm. After showing him how to use the washer, I watched him put his wet diapers into the machine one by one. Since I wasn’t sure how to clean the plastic panties, I just let him leave those in his diaper pail; he had plenty to last for the week. I led him over to his playpen that would serve as his crib.
“Good night, baby boy.” I popped a bottle of warm milk between his lips and he drifted off to sleep.
The rest of the week was pretty uneventful. I took him out in public a few more times, just to follow orders. However, I didn’t continue the daily enemas. He soiled his diapers and was almost grateful for a normal bowel movement. He was pretty uncomfortable afterwards, but since I changed him often, it wasn’t a big deal. He wet every night, and I was glad that I pinned him in three diapers instead of the usual two. Then came the fateful night….
It was about four in the afternoon and Bobby and I were in the living room, playing Chutes and Ladders. I mistakenly leaned too far forward and he got more than a glimpse of my cleavage. I could tell that he wanted to “play,” and I didn’t want to deny him. I knew my orders. He wasn’t allowed to masturbate. But for some strange reason, I just felt so sorry for him. I yanked his little body onto my lap, his back to me. I started slowly rubbing the front of his diapers. He was almost in complete ecstasy when his mom and Jennifer burst in the door, returning early from their cruise.
“WHAT THE HELL IS GOING ON HERE?!?!?!?!”
Overview: Bobby’s mom, Aunt Jennifer, and eventually Bobby get their revenge.
I looked at the two infuriated women in sheer horror. Before I could react, Bobby’s mom pulled her son off my lap and told him to stand in the corner so she and Aunt Jennifer could “talk” to me.
“What were you doing, dear?” Aunt Jennifer asked me, very sternly.
“I felt sorry for him, okay?”
“No. Not okay. You blatantly disobeyed us, and—What do we have here?” Bobby’s mom looked in the laundry room and saw a stack of her son’s diapers with slight brown stains.
“You didn’t give him enemas this week?” she asked.
“No. They gross me out! What’s the big deal?”
“We’re very disappointed in you, baby girl. We thought you could be mature and watch Bobby this week, but you’re no better than he is.” Now I was pissed. Less mature than a little bratty sissy?
“What? Come on, I may not be all that wise, but I am certainly more mature than that sniveling child!”
“Really? Let’s test that theory.” Said Aunt Jennifer. Bobby’s mom went into her best friend’s room and returned with her heavy wooden paddle. It took both of them to get my large frame over my aunt’s knee, but they did. She pulled down my pants and panties and started swinging away. My ass was on fire and I begged them to stop. Within minutes, I was sobbing my head off.
“That’s what we thought,” said Bobby’s mom, decisively. The two women dragged me into my aunt’s room and ordered me to lie down on the changing pad, to which I responded, “Hell no!” (Not a smart choice.) My aunt hit me in the face, which temporarily stunned me, and held me down while she asked the sissy’s mom to get her a few diapers. “Don’t forget the other supplies, Anne.” While I continued to struggle, my aunt rubbed diaper rash cream all over my personal region. I tried not to cry when I felt her pin one, two, three diapers on me very tightly. She wrestled a pair of lilac plastic panties on me while Anne went to the closet and brought back a frilly dress of a similar color. The two women somehow got the dress on me, along with a pair of babyish anklets and shiny black Mary Janes. To add insult to injury, Aunt Jennifer tied a frilly baby bonnet on my head.
“Anne, why don’t you stay here with Bobby while Leah and I do some shopping?”
“Sure thing.” I started to cry, and since my vision was blurry, I couldn’t see which woman shoved a bottle between my lips.
“Awwww, it’s okay, baby. Just drink your bottle like a good girl and we’ll be on our way.” I always hated warm milk. It was disgusting, but I decided do drink it anyway. More protest wouldn’t be wise. I saw Anne go over to her son. “Don’t cry, Bobby. For once in your life, this isn’t your fault.” I couldn’t believe my ears. This was the same woman who mercilessly made fun of the boy just a few days before?
My aunt dragged me outside, and I immediately heard the neighbors snicker. I waited for her to unlock the doors and then clumsily tumbled inside. “Let’s see how mature you are, you irresponsible little brat.” I didn’t know what she meant, but I knew Jennifer could be cruel and utterly ruthless if you were unlucky enough to be on her bad side. She drove to Babies R Us, and it took everything in me to keep from crying again. We went inside, and my aunt looked at the cart, knowing my 5’10” body would not fit in the front. To my horror, she took out a kiddie leash and strapped me in it. “We don’t want baby wandering off!” That was the last straw. I started crying again. She then stuck a purple pacifier in my mouth and told me to shut it. We must have walked around the whole store at least three times, up and down every aisle. She threw things like diaper rash cream, baby powder, toys, bottles, pacifiers, diaper pins, and the thickest cloth diapers I’d ever seen in the cart. I knew they were all for me, but I didn’t want to believe it. She bought everything without a word of protest from me. I just tried to tune out all of the demeaning remarks I heard from her and other customers.
Afterwards, we had to stop at Target. I wasn’t too sure why, but that didn’t matter. I started to hear a deep grumbling in my stomach. “I put a bunch of laxatives in your bottle,” she said with a sly smile. “You’ll see why enemas are important.” We walked through the baby aisle where she picked up a few boxes of boys’ Pull-ups. She also picked up a pair of jeans and a plain white t-shirt. When we were checking out, I couldn’t hold it any more. Within a few seconds, I messed myself. I started crying again. “You told me you were mature, yet you just messed your diapers in public. You know, I almost believed you, which is why I didn’t bring any extra diapers to change you into. It just shows that you can’t be trusted,” my aunt said, loud enough for quite a few people to here. She swatted me on my soiled bottom and dragged me out of the store.
When we got to the parking lot, she the box of Pull-ups on the edge of her trunk while she took out her cell phone to call Anne. Purposely, she knocked the box over and ordered me to pick it up. I started to kneel down, and she smacked my thigh. I let out a wimpy little yelp, and she said, “No. Bend over.” I looked at her in disbelief, but there’s no messing with Aunt Jennifer. I bent over, exposing my diapers for the world to see. Everyone who saw me started laughing, and I continued to cry. “What do we have here?” I heard a guy ask. As soon as I heard that familiar voice, I knew the town was too damn small. I went to high school with him, too; I also had a massive crush on him. We liked each other for a while, but went our separate ways before anything went down. He looked at me and started laughing his ass off. I lowered my head in shame, to which he responded, “Oh come on, babe. You look so…cute?” Needless to say, that didn’t help me at all.
“Excuse me, could you do me a favor?” Aunt Jennifer asked the guy.
“Would you mind checking my baby’s diapers while I get the car started?” I was horrified and infuriated. Was this guy really going to touch me in a most personal and disgusting way? I knew the answer as soon as I felt his hand.
“Hey, she’s w—“ The dick didn’t get a chance to finish. I kneed him in the crotch as hard as I could. When he was down, I punched him in the jaw. Aunt Jennifer was really freakin mad. She got out of the car and made be bend over against the trunk while she helped the guy up. She then pulled her heavy paddle out of her purse and handed it to him and invited him to spank me. She kept my diapers on, knowing I’d be much more miserable sitting in squishy waste. The boy was swinging away, having a great time, and forgetting that I was the same girl who just gave him a low blow. When I was crying my face off, Aunt Jennifer decided that was enough fun. She thanked the guy for “teaching her baby girl a lesson.”
After a most unpleasant and humiliating spanking, Aunt Jennifer put my pacifier back in my mouth, patted my bum, and ordered me back into the car. I looked out the side mirror and saw her talking to the guy, whose name is Davy. After a few minutes, she ended the conversation and got in the car and drove us home.
The whole time, I was completely miserable. I was so ashamed, sitting in a mass of gooey waste. To add to that shame, I also found myself having to piss like a racehorse. I desperately tried to hold it in, but after a long ride and several demeaning remarks, I couldn’t anymore. So I flooded my diapers and was even more embarrassed than before. Aunt Jennifer looked at me through the rearview mirror and chuckled to herself.
When we arrived home, she made me carry everything inside one at a time so the neighbors could see me as often as possible. Jerks. When I got everything inside, my aunt told me to go to her room and lie on the changing pad, to which I complied. She looked at me with a smirk and slowly peeled off my plastic panties. After that, she took off one, two, three diapers. I was a complete mess. My whole diaper area was coated with shit, and she cleaned me in a most humiliating way. After swatting me several times for no apparent reason, she sprinkled baby powder over me and pinned three diapers around my wide hips. After that, she shook out some pink plastic panties and slid them over the thick white mass. She then dressed me in a ruffled white nightgown, cut short enough to see my diapers. After half-dragging me out of her room and placing me in the playpen, she gave me a bottle and ordered me to chug it. I tried to ignore the nasty taste of the tepid milk, but to no avail. It was disgusting. A few minutes after finishing it, I passed right out.
I woke up the next morning looking at someone I didn’t recognize. He was a skinny little thing, wearing jeans and a white shirt—oh wait! That was Bobby! I’d never seen him in anything but sissy attire. “Good morning, sleepyhead,” he said, trying to fake confidence. A few seconds later, I felt someone slipping her fingers through the leg hole of my plastic panties. Sure enough, it was Anne.
“Jen, she’s soaking wet. Want me to change her?”
“Hang on. Leah, baby?”
“What?” I said, grudgingly.
“Can you get the mail for us, please?” I looked at her in disbelief, but she was dead serious. When I didn’t respond right away, I felt Anne yanking me up by the nightgown, which was no easy task. Aunt Jennifer grabbed my by the ear and shoved me out the door. I was so humiliated. I ran as fast as I could, to the mailbox and back. There were just a few bills and a Sephora catalogue for Jennifer. I returned and handed the mail to my aunt. “Get your diapered ass in my room so I can change you.”
I resented the unnecessary hostility, but I don’t think that mattered. She changed me like she had before, making it unbearably humiliating. After pinning a few diapers on me and fitting nursery print plastic panties snugly over them, she went to her closet and brought back a short pink dress and some babyish white knee socks. I meekly complied since I didn’t want to be spanked again. She zipped the dress and put the socks on me, followed by the Mary Janes from yesterday. She then tied my hair into high pigtails and tied matching pink ribbon around them. After leading me to the mirror and taunting me mercilessly, she dragged me into the living room and made me sit on the floor. When I did, she carefully lifted back the hem of my dress, as if my diapers weren’t already exposed enough.
“Okay, baby girl. The reason you’re sitting here is to get the lowdown. We’re going to tell you all about your punishment. Want to start, Anne?”
“As you know, we are extremely disappointed in you. We thought you could be trusted, but you’ve made it painfully obvious that you are immature and irresponsible,” she said, while holding up something I at first didn’t recognize. (After looking at it a little closer, I realized that they were my panties I had worn to bed one night while Aunt Jennifer and Anne were away—and they were still damp with urine from when I wet myself.) She went on. “We found these in your bag. Why didn’t you tell us you were a bedwetter? We never would’ve left you alone.” Aunt Jennifer nodded in agreement.
“Leah, from now on, things will be very different. As you can see, Bobby will no longer be a sissy. We’re going to re-potty-train him, which is why I bought the Pull-ups last night. You will take his place. You are going to wear thick diapers all the time since you certainly can’t be trusted without them. You will be treated like the baby girl you are—this includes absolutely no privacy of any kind. I will take you out in public whenever I please, dress you in whatever I please, feed you whatever I please, and change you whenever and however I please. Your bedtime will be 7:30 every night, unless of course you’re cranky—then I’ll send you to bed whenever I see fit. If you behave badly or disobey me, I have various methods of punishing you. You’ll be spanked, sometimes bare-bottomed, sometimes diapered. If you start crying, I will give you a pacifier. If you try to take it out, I will tie it around your bratty little head. You cannot watch TV by yourself, and you will watch only baby shows like Barney and Sesame Street. I will give you suppositories and diuretics constantly until you have no control left. I won’t give you enemas like I did Bobby. You’re right. Enemas are more work than the occasional messy diaper, and I find those to be much more humiliating than just wet ones. This will go on for at least a year. Any infractions will result in my adding another day onto your punishment. At the rate you’re going right now, you will be in diapers for the rest of your life.” I couldn’t take it any more and burst into tears. My aunt then put a pacifier in my mouth, and we heard a knock at the door.
A man in a UPS uniform stood on the front porch. “Leah, sweetie, answer the door.” I did, and the guy started laughing. He asked me to sign for a few packages. I signed it, and he left, still chuckling to himself. Anne ordered me to bring in the three big boxes that sat on the front porch.
After they were all in, the two women opened them. They pulled out the most babyish clothes I’d ever seen in my life. There were onesies, rompers, party dresses, all of which were designed to show my diapers as much as possible. I spat my pacifier out and said, “I’m not wearing any of this shit!” My aunt and Anne looked at me, infuriated. They went to Jennifer’s room and returned with a pink ribbon and the paddle. Anne tied the pacifier around me so I had no choice but to keep it in. They then threw me over Jennifer’s knee and to my surprise, invited Bobby to spank me. He was delighted. They decided to keep my diapers on since they were just put on me, and the former sissy started swinging away as hard as he could. Although one would think the thick padding around my ass would absorb the blows, it didn’t. It still hurt, and I still cried. During the spanking, I lost control of my bladder and started slowly wetting my diapers. When the spanking was done, my aunt cradled me on her lap in an embarrassing way, gently rubbing my diapers and encouraging me to keep peeing. “Let it out, baby girl. Babies like you have no control. That’s what diapers are for.”