Cheerleaders and Diaper Changes

„Hi, can I ask you a question?“

It was the slightly taller girl-next-door speaking.

„Sure, go ahead“, Mom replied.

„What is your son wearing?“, she asked, and the blond busty cheerleader seemed curious for the answer as well.

„It‘s just a diaper“, Mom said.

„Why though?“, she wanted to know, moving in a little closer.

Mom explained that I was „having trouble with my ejaculation“ and until I could better control myself, she’d just keep me in diapers.

„Oh my god, it’s the same with my boyfriend“, the cheerleader said, „He always cums so quickly! Maybe he should be in diapers as well.“

„Yeah, why not“, Mom said smiling. The cheerleader looked over to me.

„You probably come quickly too, right?“, she asked me, „I mean how old are you, 15, 16? So like after two, three minutes or what?“

I was caught of guard.

„I, uhhh-“, I stammered through my pacifier.

„Oh, stop it“, the girl-next-door intervened, „You’re embarrassing him. She’s embarrassing you, right?“

I didn’t know what to say, so I just shrugged. I felt my face getting warm again while she was leaning in closer, as if she herself was emitting heat.

„Her name is Jess, by the way, and I‘m Rachel“, she introduced the cheerleader and herself and just started chitchatting a little, twirling her pigtails and saying whatever was on her mind. Mostly diapers, but some other stuff too. Her eyes lit up when Mom mentioned she had a psychology degree.

„Oh no way“, Rachel said, „I’ve been trying to get into hypnotherapy for a couple of weeks. But also more, like, sex… related.“

„Oh, interesting“, Mom said, „Quite a topic, right? I remember writing a paper on erotic hypnosis back in my day and being hooked by the topic. I even thought about getting certified for a while, but ended up sticking to normal therapy.“

„Oh yeah, I was thinking about doing that eventually too“, Rachel answered, „I mean, like, getting certified, you know? But first want to be sure it’s really my thing before I decide to do that for a living. For now I just think it‘d be like such a cool and kinky hobby. I mean who wouldn’t want to have their boy- or girlfriend do all the perverted stuff you want them to and not even remember afterwards? Or have someone get like super wet or cum in their pants by saying a single word or something.“

She was chuckling, then biting her lip and glancing over to me.

„Yeah, exciting stuff, sweetie“, Mom said, „If I was as young as you again, I‘d really take the time dive into this I think. While I still had the brain capacity to get really good at something, you know? I mean I could for sure picture you as a cute, passionate hypnotherapist, which this country needs more of by the way. I‘d say go for it.“

Rachel smiled.

„Well thank you!“, she said, „You know, I’ve actually been talking to a friend about this, how social media-“

While they were talking, Jess was checking me out a little. Her mouth was open and her eyes were wandering over my chest, belly and crotch and down my legs. She either didn’t think or care about the fact that I could see her doing this. At least that somehow made it a little less awkward.

„Soo, like, your diaper’s pretty cute“, she said, „Is that like your thing?“

„I, uhh, not really“, I answered through my pacifier, „It’s only because my Mom put me in them.“

„Hm, kinda hot“, she said, „Wearing what Mommy tells you, huh? She always been like that?“

„Well, uhm, I only knew her from the age of 11“, I explained, „Technically she’s my Step Mom, I don’t really know my real Mom.“

„Oh, cool, so you guys are like free to fuck and do whatever?“, she asked.

„I- I guess so“, I answered, „But we don’t really do that type of stuff. Like at all.“

„Huh“, she said, „I don’t think I could live with someone that long without fucking them, honestly. Rachel’s my roommate and my dick‘s inside her pretty much everyday.“

Huh, dick?

„Wait“, I asked, „Are you… both trans?“

„Oh, no“, she said, „We’re both 100% female but I had surgery to get a dick a couple of years back.“

She pulled up her dress a little, revealing a bulging thong with pink and white stripes.

„Works like a real one though“, she said and proudly smiled. Her un-embarrassment embarrassed me somehow.

„Sooo you’re in an open relationship kinda situation?“, I asked.

„Oh, no, I‘m with my boyfriend“, she said.

„But you’re having sex with Rachel?“

„Yeah.“

„Wouldn’t that be… uhm, cheating, kinda?“

„What?“, she asked, „You mean me and Rachel fucking? Oh no, that doesn’t count. That’s just girls having fun, you know?“

Oh yeah. No that made sense.

„I uhh“, I struggled to find words, because neither agreeing nor disagreeing so openly felt right. So I just said something like „M-hm“, nodded and stood there, sucking my paci a little.

She didn’t seem to mind me not talking though. Her bored looking eyes just started wondering around the mall a little, while her right hand slipped unter her skirt, pointer finger gently running up and down her bulge.

„My gosh. So freakin hard right now.“

We both just kinda started listening to Mom and Rachel‘s conversation again. They seemed to really hit it off.

„That stuff can go in a lot of directions, I just kinda know the basics“, Mom said, „So don’t expect too much, darling.“

„Oh, anything would be a big help“, she said and before I knew it, they had agreed to spend an afternoon at our house, to help her with the whole hypnosis thing.

After a quick hug Rachel thanked her, waving us goodbye, before just quickly reaching for my pacifier and running her finger around the ring part.

„Oh and this is just so cute, you should definitely keep it in“, she said, „Like, all the time, you know?“

And with that, they walked off, merging back into the girl group they had come from.

"See, it's not that bad. People are not judging you, they're just curious," Mom said.

„Mom that was super embarrassing“, I said through the pacifier.

„Nonsense, you were all very cute", she said, „And they were into you, did you notice?“

„Hmm not sure“, I replied. Maybe they were just friendly, I thought. But that was always the thing with talking to girls.

Anyway, I was probably going to die if I had to speak to another person, so I couldn’t wait to finally get out of there. I also really needed to pee, which I told Mom. She looked at her watch and was thinking for a moment.

„Oh, you know what“, she said, „I know we had another stop planned, but I really lost track of time talking to that nice young girl. And I don’t want to rush through this, because that’s never fun. Maybe it’s better to do it properly next time.“

My god, thank you, I wanted to say, but I just nodded approvingly. I didn’t want to break this and make Mom change her mind by accidentally saying the wrong thing. So after grabbing all our stuff and working our way through some more flocks of people, we walked silently toward the holy entrance of the mall, through which we had come in. Grand, golden gates of ornamented beams, shining bright in the late afternoon sun. (Okay, I admit, that was not quite the truth, but that’s how it felt.)

As we were getting closer and the doors were slowly getting bigger, I was only crossing my legs a little, since I actually like really, really needed to go, as I just now noticed.

„Oh, we‘ll be home in no time“, Mom assured me, who had noticed me walking strangely, „20, 25 minutes max. And besides…“

She smiled at me.

„What do you mean?“

„Well, honey“, she said, „Do I really have to spell it out for you? You’re diapered, darling. So don’t worry about holding it, okay?“

I was embarrassed that I thought about it for a moment. It would actually be really comfortable right now or even on the way home. I mean I was wearing a diaper anyway and the rules said I wouldn’t get out of it until later. Plus, it was pretty thick too. So there would be no way that it would leak or anything. But no. Even if I did it without Mom noticing, she would see later when changing me. Then she’d probably make me wear them more often or whatever and that wouldn’t be worth it. But no problem.

I could for sure wait until we were home.

The sun was already low enough to nicely shine into the parking garage, while we were walking to the car. Mom and I got in and were finally on the way back home.

„Did you notice she wasn’t wearing any panties under that skirt? That was the cutest thing, wasn't it?", Mom was telling me, her eyes on the road. Trees were swooshing by left and right, but I had my head down going through the bag from the bookstore earlier.

„Hm? Who?“, I asked through my pacifier, which I was sucking on a little comfortably now. Sure, Mom and people passing us could still see me do it, which was a little embarrassing, but that I could get used to.

„That girl Rachel I talked to“, she said, „The taller one with the brown hair and white tennis skirt. With the big round glasses.“

„Yeah, yeah“, I said, „No I didn’t notice.“

I put all my new books onto my lap into a nice little pile, so I could look at them one by one. I had gotten the first and second edition of „Aphrodite Assassin“, another one called „Girl Roommates Vol. 1“, which apparently was about a couple of college girls sharing an apartment and… well, a couple of other things too, „Twin Pervs Next Door“, which I just thought had such a hot cover, then also „Learn the Alphabet with Hentai“, which I still had to finish, „Learn Numbers 1 to 10 with Hentai“ and „My First Hentai Coloring Book“, the last three all being from the same series that looked like baby books. They even had the same girl in that kindergarden teacher outfit.

„She didn't seem to care that much. Or at all, actually. I didn’t really get a sense of shame from her in any way, huh? Not even in the slightest.“

She chuckled.

"That's just my kind of girl, you know?"

„Hmm“, I just hummed through my paci.

„Well anyway, I'm pretty beat, so we'll order some food when we get home, alright? Or maybe in an hour so it’s not super early“, she said, „What do you say, Indian?“

I nodded, flipping through ‚Aphrodite Assassin‘, „Sounds good. Can we get the garlic naan this time?“

„Uhmm, alright, sweetie“, she agreed, „Guess you deserve a little treat after all that, right?“

She smiled.

„Thanks, Mom“, I said.

„Okay so Haley should be back from university by six, so I‘ll get the chicken tikka masala for her, because I know she always likes that“, she thought out loud, „Aaand a lamb rogan josh for myself I think. Yeah. And you're gonna want your usual, right? Butter chicken?“

„M-hm“, I said, turning the page.

„Alright, perfect“, she said, „If we order in an hour it should be there by like seven thirty. If you guys want to we could make a nice movie evening out of this, huh? Get comfy, relax a little?“

„Yeah maybe.“

I was crossing my legs even more and shifting around in my seat, my diaper crinkling while I did so.

„Honey, if you need to go so bad, just pee“, she said, „That's what diapers are for, sweetie.“

I told her it was fine and that I‘d wait until we were home.

„You don’t have to make it so hard on yourself and squirm around like that, you know? You know I don’t mind.“

Well, I did.

„Mom, don’t worry, I can hold it“, I assured her.

„Okay, honey“, she said, „But you know you‘ll first have to cum in your diaper before I can take it off. Those are the rules.“

I sighed. I told her I knew that and that I would just read a little now to distract myself.

And right as I said that, I felt the car slowing down. I looked ahead and saw rows of break lights, stretched over the road, coming closer.

„Ah, should’ve expected something like this on a Saturday evening“, Mom said, „Makes sense that everyone’s going home right now.“

She reached over and patted my thigh.

„I don’t know how long this will take, but by the looks of it I‘d say at least 30, 40 minutes more“, she said, „Sweetie, I know you can’t hold it for that long. So don’t worry and just pee your diaper. It’s okay, I promise.“

I sighed again.

„Do I really have to?“, I asked.

„Oh, yes, sweetheart, the rules kinda make it so“, she said, „And you’re stuck in this car anyway, honey, so what else do you want to do? I‘ll turn on the radio, so I won’t even hear you peeing your diaper, okay?“

„Mom, I think I-“, I began.

„Shh, it’s okay, darling“, she said.

With that, she turned on some local radio station and started humming to some pop song that was on, not paying much attention to me anymore.

I didn’t even try to argue, since I knew there wasn’t really any other option. Instead I just kept on reading and looking out the window, sucking on my pacifier. I don’t know why, but I put one hand in between my legs, feeling the bulge of the thick diaper. Maybe because I wanted to make sure that I was really wearing one and wouldn’t be peeing my pants in a minute. And for some reason that, combined with me sucking my pacifier, made me a little calmer.

But I didn’t feel like I could just pee my diaper right now. Even after a couple more minutes of trying to just gradually relax, there still was a kind of mental block, keeping me from letting go. Made sense, since I had been out of diapers for like 18 years. It took a good one or two more minutes, but I just kept my hand in between my legs, assuring my mind that I was really wearing a diaper, tried my best to relax, calmly breathing out as deeply as I could and slowly but surely felt the front of my diaper getting wet, growing a bit heavier and thicker. After a couple of seconds the mental block was gone and the warm feeling was spreading all throughout the front and eventually all the way to the back part and my butt cheeks. I even felt the warmth on my hand between my legs.

It spread out a little further and the material expanded some more, but even though it had been a lot, the diaper didn’t really feel full. Mom must have put me in a night time diaper or something.

Just to be safe I checked my pants in all the spots I could while sitting and was relieved that it didn’t leak anywhere. Generally I was pretty relaxed all of a sudden. I mean of course I no langer had such a full bladder, but there was more to it than that. I felt like finally the whole stress and embarrassment of the whole diapered mall adventure finally subsided, which was a great sensation. I kinda just sank back into my seat and exhaled, closing my eyes for a second. I then noticed that Mom would probably be able to tell that I‘d peed my diaper through that, so I just nonchalantly looked out the window a bit more, watching the landscape fly by.

The rest of the drive I spent with flipping through the comic book a little more, listening to the radio, but mostly enjoying the nice feeling of the diaper. I‘ll admit, it did turn me on in a way. Especially while simultaneously looking at pictures of a half naked femme fatale assassin, it made dick grow in my diaper a little.

A good 30 minutes later we pulled up into our driveway and went inside. Mom was taking off her shoes and putting the keys on the counter, before she started rummaging around the kitchen, probably looking for the Indian food takeout menus, since she could never remember their number.

Our bags we just left in the living room to be unpacked later or tomorrow or something. I told Mom that I was gonna take a shower, but she reminded me, that I had to cum first, before taking off the diaper.

I had almost forgot and tried to think of an excuse or loophole to get out of it. But I couldn't think of any.

„Just unbutton your pants and go sit on the couch“, she instructed me, so that’s what I did. She came over.

„Alright honey, go ahead“, she said, „I'll watch.“

„Hm?“, I said with the pacifier still in my mouth.

„I said, I'll watch you“, she repeated.

I was surprised and a bit embarrassed.

„Can't you wait until I'm finished?“, I asked.

"No, sweetie. This is not a private activity. As long as you wear a diaper, you will masturbate with me or Haley watching“, she explained.

My gosh, Haley as well? No way I‘d ever recover from that.

„This is so embarrassing“, I said.

„It'll be fine“, Mom said, smiling, „Come on, honey. You got this.“

„Uhh, okay“, I said pulling the waist band down a bit and slipping my other hand into my diaper.

„What are you doing?“, Mom asked.

I blushed and replied: „Well, I need to take my dick out so I can masturbate. I can't jerk off while it's still in the diaper.“

„Nonsense, you can do it just fine with the diaper on,“ she said.

I didn't quite understand, so I asked, „How am I supposed to do that?“

„Well, glad you’re asking“, she said, smiling, and took a big long pillow from the other couch.

„Just hump this“, she said, „If you want you’re even allowed to close your eyes and imagine you’re having sex with your crush or whatever girl or boy you like, honey.“

„Mom, I‘m already feeling like a pervert“, I said, „Do I really have to?“

„No, honey“, she said, „We could also get you one of your hentai books for inspiration instead if you don’t want to imagine something.“

„I mean, like, grinding on this pillow“, I said, „Do I really have to do that, Mom?“

„Oh yes, darling, of course“, she said, „I‘m sure there are lots of boys and girls doing that if they’re not getting laid. Plus, I can't let you use your hands and make a mess.“

„Mom, I-“, I began, but she laid her hand over my pacifier.

„It’s okay, sweetie“, she comforted me while guiding me to sit down on the pillow, „Just back and forth a little. Just like that.“

I‘ll admit, I probably wouldn’t have done all that, hadn’t I already been pretty horny from the visit to the book store earlier, the pretty girls who had talked to me and so on. But like that, I just started rocking back and forth shyly.

My diaper made some crinkling and squishing sounds while I was gently humping the pillow. I‘ll admit, my dick was still a bit hard from before in the car and the sensation of it rubbing against the wet insides of the diaper felt really good.

I was sucking on my pacifier and closing my eyes to save myself some embarrassment, while thinking about a cute girl I had a crush on in high school. I remembered her soft looking lips and how nice and friendly her smile was. That thought alone kept me going for a while. My cock was already so hard, even going slow nearly made me really horny.

„Don’t be afraid to go a little faster“, Mom said, „You want to cum after all, right? And don’t be shy to moan as well, sweetie.“

So I sped up a little and sure enough, I did make some moaning sounds and felt myself getting closer to the edge. But I wasn’t quite there yet. I grabbed the pillow with both hands and humped a little harder, focusing on sucking my paci and not letting the embarrassment distract me. But when closing my eyes again, instead of the girl, I saw Jess and Rachel. Both of them were watching me grind my diapered boner and giggling to themselves, but smiling at me.

„You wanna cum in your diaper for us?“, they asked and giggled again, „Come on, we’re waiting…“

I felt the pleasure building and kept on humping, moaning through my paci.

„Hmm, that’s a good boy“, Jess and Rachel smiled, both of them with their hand under their skirt, Rachel rubbing her clit through her panties and Jess with her dick out, „Want to make your cute little cock shoot a nice big load in your diaper for us? We‘d be so proud of you, cutie.“

I kept going and felt my hard cock tingling and feeling really good, my balls and butthole clenching, moaning and finally spurting hot wave after hot wave of cum into my diaper, while continuing to hump the pillow. I didn’t stop humping until my balls were completely empty, finally slowing down little by little and letting myself fall on the pillow. Gradually I caught my breath.

„Wow, that was really cute, sweetie. So adorable how you were grinding on the pillow in your diaper and sucking your pacifier. I wish you could see yourself.“

I felt a little embarrassed that Mom was watching, but also in the moment to exhausted to care.

„That’s how you’re gonna cum from now on, sweetie. And you already did really well, so be proud, okay?“, she said, „What do you say, we give you a nice change, huh?“

„M-hm“, I nodded, still with the pacifier in my mouth.

We were in Moms‘s bedroom and I was lying on my back on her bed, with all the pillows and the duvet pushed to the side. Underneath me was a blue changing mat covered in fluffy clouds, that Mom had probably bought at that store in the mall earlier. Next to me were baby wipes and Mom’s new diaper bag with a couple of other supplies. But right now, she was still busy opening the tapes on the sides and opening the front part of the diaper, exposing my private parts. Cold air was hitting my soft dick and balls and whole crotch area, which was still wet with pee and cum.

„Wow, sweetie, that’s a really good amount of cum“, Mom said, „Really proud of you, honey.“

She smiled and began wiping it off.

„Must have felt really good in a nice warm and wet diapy, huh?“, she added, „You really peed a lot, sweetheart. Your diaper’s nice and full, hm?“

She smiled and threw the wipe away.

Next was my butt area, for which I had to lift my hips and spread my legs, so Mom could reach all the places she needed to.

It probably goes without saying that I felt really **** and exposed like that, but Mom didn’t seem to mind at all. I guess that was just something about Moms in general, that they just weren't easily grossed out or affected by awkward situations. Still, I didn’t say anything and just stared at the ceiling, listening to her talk and letting her clean my butthole and do whatever.

It had something about it though, being taken care of and not having to do or think of anything. I just had to lie there and let her do all the work. And while she was carefully wiping me down and cleaning every little corner of my crotch and butt, she started humming a little tune. A slow and pretty melody, and somehow familiar. But I couldn’t remember where it came from.

„Okay, all done“, she said, „Want me to put you in some pyjamas or do you wanna take a shower?“

„A shower sounds really good right now“, I said.

„Alright, go and relax, okay?“, she said, „Just remember to use some baby oil afterwards, especially in your diaper area, you really need some moisture, sweetie. If you want I can do it for you.“

I told her it was fine and after helping her put all the stuff back into the diaper bag, went to take what probably was one of the best showers of my life. I felt like the warm water was melting all of the stress inside my body after a day like that. And finally being by myself made it all the better. You bet I took my sweet ass time in there.

After that I used some baby oil as instructed, which my skin absorbed really well, slipped into some cozy and comfortable pyjamas and made my way to the living room, where I was already greeted by the delicious smell of Indian food, and by Haley as well. She was sitting at the kitchen counter and was chatting with Mom, both already with some red wine in their glasses.

As it was getting dark outside, Mom lit a few candles and turned off the main light. Strangely, picking a movie went smoothly, in under 15 minutes and without a single fight. We settled on the original 1980s ‚Karate Kid‘.

After we had finished our food, we moved to the couch, getting out blankets and later snacks.

I faintly remember struggling to keep my eyes open and kinda dosing off toward the end of the movie, before I mustered up the energy to half-assedly brush my teeth and fall into bed.