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?!?!?!?!”