I’ve been trying my best to look for a new job, but it seems that nobody is interested in hiring. Cooks, servers, cashiers, and various other dead end jobs all seem to be filled despite all of the ads that they’re hiring, as well as the fact that such places are always understaffed.

Thankfully, my best friend Kelsey is letting me stay at her place for now. She’s out often, as she does a lot of traveling as a social media influencer. As such, I often have the place to myself. Today is one such day.

Just like many other days, I sneak into her room, and open up her step-in closet. She has probably hundreds of dresses, skirts, blouses, and other clothes in here, not to mention the ones in her drawers. I grab a cutesy pink dress with the pattern of some cartoon character, then walk over to her dresser, and rummage around carefully. I can’t let her know that I do this, of course.

Ever since I was in elementary school, I wore my sister’s clothes. My parents didn’t like that. They said that I was a man, and that this wasn’t something that men did. Thankfully, I’m a lot more careful nowadays.

Today, I choose a pair of white panties with some kittens on them, and matching bra, as well as some white thigh high socks with pink ribbons at the end. I put the ensemble together, and stare at myself in the mirror.

It’s hard to deny the fact that I look absolutely adorable. Kelsey really loves cutesy clothes like this, and often does cosplay. Her fans also love it. In her private time, she also wears cutesy stuff, including stuff that she would never show her fans. Namely, diapers. I’ve been unsure about wearing them myself, but as she’ll be gone for a few days, I’ve brought the same kind she uses, and stashed them in my room.

I head back to my room, and stare at the package. I’m still hesitant, but they look really cute, and there’s nothing I love more than wearing cute stuff. Slowly, I take off the panties, and slip the pull-up diapers up my legs. They’re pink with strawberries on them. It feels a bit weird, but they seem to fit alright.

I return back downstairs to eat, then spend an hour or two masturbating before sending out some applications online, then playing some games. Before I know it, night falls.

I change into a sleeping dress, one that is super frilly and barely covers the diaper that I’m wearing. These diapers are meant for being worn overnight, so I keep them on, and assess myself in the mirror. I do a little spin, watching as the dress easily reveals the diaper. I blush a bit, then crawl into bed. I’m slow to fall asleep with the strange sensation and knowing that I’m wearing a diaper, but eventually, I do fall asleep.

I don’t notice the door open in the morning. Kelsey has come home early, and the house is a mess. The drawers in her room are open, the door to her room and the closet are open, laundry hasn’t been done yet…

“Sky?” I hear her call out. I bolt straight up in bed, and turn to my bedroom door just as it opens.

“Don't come in!” I scream.

Too late. She steps in, looking confused. Then an understanding dawns on her face.

“Oh my gosh! I didn’t know I had a little sister!” she exclaims.

“I’m sorry! I can explain!” I tell her.

She giggles. “No, there’s no need for that. I can see that you’re wearing my clothes, as well as some diapers under that dress. I can’t exactly judge you, seeing as I do the same.”

I look at her, my face flush with embarrassment. “I thought you would be out for several days.”

“Hmm? Oh. No. I was just sleeping with a girlfriend on the other side of the city. I was planning to come back today.”

“I’m sorry,” I mutter.

“No, no! Don’t be! You look totally cute! Your slender face and long hair make you look like a girl, anyhow, so those clothes really suit you!”

I stay quiet for a moment.

“Is it okay if I ask something?” she asks.

“What?”

“Did you use those diapers?”

“What? No! Of course not! I don’t wet the bed!”

“Aww, but that’s part of the fun! Do you need to pee right now? If so, just use the diapers.”

“I - I can’t do that!”

“Please, you’re already wearing them,” she rolls her eyes.

I gulp, and try to focus on peeing, but I can’t.

“I can’t do it,” I tell her.

“Most people can’t just do that, so don’t worry. For now, squat on the ground, and try to pee. That should be good enough to work.”

I slowly step out of bed, then crouch down on the ground, and focus on peeing. After a second or too, pee does begin to come out, and I wet my diaper.

“I… I did it,” I tell her in a hushed tone.

“Aww, what a good little girl!” she hugs me. “Now, I’m sorry for waking you up, baby. Are you still tired? Do you want to go back to bed?”

I nod my head.

“Alright. Did you want to sleep with your big sister since I’m here? We can even wear matching diapers!”

My face is deep red, and part of me wants to scream no. but the other part of me wins over.

“If you want to…”

She pulls me over to her room, and starts changing. I advert my eyes, but she laughs.

“Come on! I’m your best friend! Don’t be embarrassed!”

Admittedly, there isn’t much to look at. Even though she’s an adult, she isn’t exactly stacked. Still, a naked woman’s body is a bit too much for me. I can feel something stirring in my wet diaper.

Kelsey changes into the same type of pull on diaper as me, and a onesie, then we crawl into bed and cuddle together. I’m too excited to sleep, though. My mind rushes for well over an hour.

“Can’t sleep?” Kelsey asks.

“No.”

“Me either. This is just too exciting! I’m so glad I have a little sister just like me!”

“Yeah. Except I can only assume that your diaper is dry right now.”

“Do you wanna feel?”

My face is beet red. “I don’t know about that…”

She takes my hand, and brings it down to her crotch. I go in through the side of the onesie and diaper, and feel that her diaper is, in fact, wet.

“How do you feel knowing that your sister peed in bed right next to you? I’m pretty embarrassed.”

“You shouldn’t be, I peed in my diapers first.”

She giggles. “Yeah, you did! Can I feel?”

“Huh?”

She doesn’t wait for an answer. She puts her hand over my diaper, and laughs.

“Yeah, that’s pretty full, alright! Don’t go peeing any more, cuz it probably can’t hold more than that!”

“I’ll be sure to keep that in mind.”

“Since we can’t sleep, do you wanna play a bit?”

“Play what?” I ask.

She winks. “Well, that depends what you’re interested in. it could be a video game, or with plushies or dolls, or…”

“Or?”

“Something a bit more naughty?”

“... Like what?”

Kelsey gets up on her knees, and kneels over me, holding my shoulders down, and slowly lowering her body onto mine. Her wet diaper sits on my chest.

“Maybe a bit of baby wrestling?”

I try to wiggle away from her, but she holds her grip tight. Every time I thrust my body up, her wet diaper squishes down on me, and I’m also reminded of my full diaper as my body comes back down. As I do, Kelsey basically rides the thrusts, giving my a bit of give before forcing herself back down onto me.

“Aww, is the little baby too weak?”

“You’re wearing a diaper too, baby!”

“Ha! Maybe! But I’m still the older one!”

I groan as I continue to struggle.

“Do you give up?” she asks.

“No!”

She lets go of my shoulders, and lifts herself up a bit. At first, I think she’s done, but she just pulls my dress up, and starts tickling me.

“Hey! Stop it!” I complain through fits of laughter.

“Not until you give up! Do you give up!”

“No! Never– oh.” I try to stop as I realize that I just peed myself more. But she doesn’t let up. “Wait! Wait! I’m pee- ah! Stop! I quit!”

Kelsey laughs, and then finally gets off of me. My diaper has burst, and her sheets are now drenched in pee. Thankfully, she has a plastic sheet under the blankets to protect the mattress, but the blanket will have to be washed.

“We’ll worry about that later,” Kelsey says as she pushes me back down.

“Hey! Wait! Now what?”

“Now what? More fun, of course!”

“No! No more tickling!”

Kelsey lies right on top of me, her small breasts pushing up against my nonexistent chest, her legs ending below mine, and her lips a mere inch from my face.

“Maybe we can do something else, then?” she asks.

“Like what?” I ask, gulping.

“Like this,” she says, as she closes the gap between us. As her tongue enters my mouth, her fingers reach their way into my diaper, and wrap around my penis. I gasp in surprise, but certainly don’t try to stop her.

Slowly, I reach my hand down, and unsnap her onesie. I then reach my hand into her wet diaper, and start to finger her. She moans in pleasure, and lightly humps at my arm, thrusting my fingers deeper into her. The whole time, her hand rubs around my dick and balls, and her tongue mingles with mine.

Finally, I can’t take it any more. I ejaculate, and slump down. But Kelsey doesn’t stop. She continues to hump me and shove her tongue in my mouth, and I make sure to try and keep up, even if I am exhausted. I twitch my fingers in her diaper, but it seems like she wants more.

“Hold on,” she says, getting up in the first time in what seems like forever. She jogs over to a nearby cabinet, and pulls out a dildo. She then tells me to turn around.

“Uh, what are we doing?” I ask, even though I’m already obeying.

“Oh, you already know, baby.”

This is a double ended dildo, which she attaches to a strap, and lubes up. She then pulls my wet diaper down, and kneels over me. Slowly at first, making sure not to hurt me, she begins thrusting the dildo up my butt. Thankfully, it’s pretty small, so even though I don’t do a lot of butt stuff, it doesn’t hurt. It actually feels pretty good, and the fact that I know that it’s best friend of over 10 years doing it makes it even more hot. My dick is a bit limp, but it revives a bit as she goes at it.

Eventually, she does orgasm, and as she gets exhausted from the thrusting, she calms down, and then lies down next to me.

“Did you like that as much as I did?” she asks, giggling.

“I think so,” I nod my head. My head feels like it might explode right now.

She rolls over, and hugs me tight. “We don’t have to do this every day, but if you wanted to, we definitely could. But regardless of if we have sex or not, Sky, you’re my little baby sister, and I love you, okay? You don’t need to get a job. Just stay here and be my little baby.”

“Are you sure?”

“There’s nothing in the world I would want more than that.”

“Then ok,” i say, taking her hands in mine, and kissing them.

“You’re such a sweet little baby,” she whispers. “Still, that doesn’t mean that you don’t have to do any cleanup. Come on, we can’t let these sheets just smell like piss forever! Laundry time!”

I sigh. “For you? Anything. Even laundry…”