Diaper Rules

The next day was a Saturday. I was up pretty early, but Haley had already gone to the gym. I never knew how she managed to work out this early.

Mom didn't have to work Sundays, so she just went shopping in the morning.

When I saw her leaving, she wasn't wearing much, as it was a rather warm summer day.

As Mom left the apartment in a blue summer dress, Haley came back from the gym. She was wearing a grey tank top and tight black yoga pants. Her boobs were jumping around and her nipples were poking through the fabric.

„Hey baby bro“, she greeted me and winked, „Gonna put stuff in the laundry and take a shower, alright?“

„Didn’t a-ask“, I replied singing in my rough morning voice and shuffled to the living room, going for the sofa. I was still in my Pyjamas and a little drowsy. I sat down.

She went into the washing room, returning about 5 Minutes later, already naked and blowing me a kiss on her way to the shower.

„See ya.“

And boobs and ass jiggling, she danced into the bathroom. My god. I sighed and sunk into the couch, running my fingers through my hair and stretching a bit.

The social media addict that I am, I instinctively took out my phone, scrolling a little through Instagram, texting friends and so on. Passing time.

About 20 minutes later Haley came out of the shower, put on the minimum amount of clothes required to not be considered naked and joined me on the couch, waiting for Mom to return.

She took out her phone as well, both of us mindlessly scrolling through whatever our poison of choice was. About 5 minutes passed, then I looked up at her.

„Aren’t we bad siblings?“, I asked.

„Hm?“, she turned her head but her eyes took a few seconds unstick from the screen.

„Shouldn’t we be talking or something?“, I said, „You know? Bonding?“

„Huh“, she said, „Guess that’s true.“

She paused for a second.

„You did suck on my tits yesterday though, I‘d say we did a good deal of bonding there.“

„Alright“, I explained myself to no longer partake in this conversation and Haley smiled victoriously.

Mom’s keys jingled some time later when the apartment door opened and she stepped inside with two bags. She took off her shoes with her feet and on the way to the living room and kitchen she put a pack of diapers next to my door.

„Go set the table“, she told us.

„What is that?“, Haley asked and pointed.

„Oh that“, Mom said, „Matt‘s getting some diapers.“

Haley smiled.

„Huh, that’s new. What for?“

Mom explained everything and Haley laughed.

„Cool!“, she said, „But why don't you just have him use a condom? I can lend you some if you want.“

Mom put down the bags on the kitchen floor and sorted cheese into the fridge.

„Oh, that’s kind of you, darling, but no“, she said.

„Okay, but why though?“, Haley wanted to know.

„Well two reasons. Firstly, I want to make sure he really ejaculates into whatever he‘s wearing. And a condom is really easy to take off, whereas a nice, snug diaper will probably stay on. And secondly - well, picture this. Matt‘s jerking off on the couch. Then you walk in with a short skirt or fishnets and probably no panties as usual and tease him by bending over, flashing him or whatever. I know what kinda stuff you do to him. And now imagine him rock hard, with a condom already on his dick, ready to fuck. What do you think will happen?“

She looked at us both, while her hands continued sorting.

„I don’t want you guys to make decisions you‘ll regret later on“, she continued, „And believe me, that happens. Now with the diapers on the other hand, you can tease him to no end and he can blow his big load nice and safely. Alright? So diapers it is.“

Haley shrugged.

"Alright then, guess it's not a bad idea", she replied.

I was kinda shocked by how they both just decided that I‘d jerk off in a diaper from now on. As if I wasn’t even there to hear them talk about this.

„Hey“, I drew the attention to me, „How about I just don’t do it on the living room couch?“

„Well, honey, I think you should, actually“, Mom said.

„What?“

„Sweetie, I have to be able to watch over you every now and then to check that you’re really wearing your diaper“, she explained, „You‘d probably just take it off in your room.“

„Yeah you totally would“, Haley nodded and smiled.

„Yes because that’s how normal teens beat their meat“, I said, „What, am I crazy here? And couldn’t I just jerk off in my room normally? Without fucking diapers?“

Mom came closer. As always, she had this aura of de-escalation. I just then noticed I had never experienced her stressed out or tensed.

„Honey, firstly, you’re not crazy at all“, she said calmingly, „And secondly, I totally understand your embarrassment. Masturbation is a sensitive topic for kids your age. Especially when stuff like diapers is involved. But we won’t judge, right?“

She looked over to Haley.

„Yes, of course“, she said, trying not to smile.

„Haley“, Mom said, „I think we can both remember what kind of stuff you did when you were his age. So please.“

Haley nodded. I sighed.

„Alright, maybe just drop this whole discussion about jerking off and diapers“, I said, „This is pretty embarrassing.“

Mom nodded understandingly.

„Alright.“

„I agree“, Haley intercepted, „Let’s not argue and please eat something. I‘m starving.“

„You’re right“, Mom said, „Let’s eat something.“

So we went and got plates, cutlery, toasted some toast, fried some eggs and poured ourselves some orange juice. We sat down and had a nice breakfast, watched the news on TV and talked about what we were gonna do today.

Mom had a pottery class every Saturday afternoon. It was a group with just „her girls“ on the outskirts of town. But she told us she cancelled that today.

„I‘ve got a little trip to the mall planned“, she said.

„Weren’t you just shopping?“, I asked while taking a sip of orange juice.

„Well that was groceries“, Mom explained, „I‘m talking about going shopping, you know? Shopping shopping.“

„What do boys even do for fun?“, Haley sighed.

„Well anyway“, Mom continued, „I was hoping you‘d join me, Matt.“

„Uhm, ok, sure“, I agreed, assuming she needed a strong young man to carry her bags.

Mom seemed happy that I agreed and she told me we‘d go about an hour after breakfast.

After we ate, Haley went to her room, doing god knows what while I helped Mom cleaning up and packing the dishwasher.

After we were done, Mom shut it and the machine started its soft familiar humming. I leaned against the counter and felt its vibrations as she began folding the table cloth. There was silence for about half a minute. We could both tell that something was in the air. So I just spoke my mind.

„Diapers, Mom? Really?“, I asked calmly, as to show my friendly intent, „I know I agreed, but I‘m pretty embarrassed.“

She put away the table cloth and looked at me. Her blue eyes were soft and warm.

„Sweetie, you really shouldn't be“, she said, „It’s just diapers, honey. You wear boxers, briefs and swimming trunks in public, don’t you? It's just underwear.“

I sighed.

"No, it's not", I said.

She smiled and came over to me.

„Yes, it is. Trust me. It's just a cute, innocent diaper and that's all. Nothing weird about it.“

„See, why are you calling it cute and innocent?“, I asked, „Because diapers are for babies, not teens and grownups.“

„Honey, it says ‚teens‘ on the packaging“, she explained, „That’s really just social norms you got stuck in your head.“

I had to think about that for a second. Was it really? Maybe she did have a point with that.

„I guess so, but I don’t know“, I said, „It’s still a diaper.“

„Sweetie, as I said, just another piece of underwear. Think of it as a thick pair briefs or something“, she replied, „Sure, most of society has made up its mind about diapers being for babies, but as you see, they’re made for all ages, so why shouldn’t everyone get to wear them, hm?“

„I don’t know“, I said, „Guess it just doesn’t feel right to me. I feel like a teenager in diapers is automatically a weirdo. Maybe because of that society thing, I‘m not sure.“

She looked at me sympathetically.

„Honey, you seem kinda confused to be frank with you here“, she said, putting her hands on my shoulders, „I think you‘ll understand when you just put one on. You know, I‘m expecting of you to at least try diapers once anyway. So why not get it over with today? Maybe you won’t have such strong feelings concerning diapers anymore when you had one on, hm?“

Her tone was so reassuring that I felt a little disarmed and didn’t say anything. For a moment there was only the quit rumbling of the dishwasher. I looked up at her.

„Does it really have to be in the living room though?“, I asked.

„Well, darling, I think it’s important for you to learn that this isn’t something to be ashamed of, that you have to do secretly“, she explained, „This might be awkward at first, but you’ll thank me later.“

She did have a point. I nodded slowly, then turned to her.

„If I still really hate it afterwards, we can just quit the whole thing, right?“, I asked.

„Well, I‘d really appreciate if we could follow through with this“, she began, „But I also don’t want to **** you to do something you really, really don’t want to.“

I sighed.

„Thanks, Mom.“

„But only if it’s really bad, like causing-you-physical-pain-bad“, she said, „And I expect to hear your honest opinion, alright?“

„Sounds fair“, I agreed and nodded. That was good enough news, I thought. She smiled.

„Alright, let’s get you diapered then“, she cheered, „You can get naked in my room and lay on my bed. I‘ll be there in a minute.“

„Wait right now?“, I asked.

„Yes, why not“, she said.

„Uh, do I have to be like completely naked?“, I asked.

She laughed.

"Yes, sweetie. Unless you wanna keep your socks on or something. Socks are fine.“

I rolled my eyes and sighed.

"Whatever", I said, going to her bedroom.

I took off my clothes and folded them. I put my socks and underwear on top of the pile and sat down on her bed. My bare cheeks felt good against her soff, fresh bed sheets.

It took her a few minutes until she came in. With her, she had the pack of diapers, wipes and powder in her arms which she threw onto the bed.

"Ready?", she asked and opened the pack.

"I guess so", I said.

She gave me a smile, took out one of the neatly folded diapers and held it between her knees.

"Legs up", she said and helped me raise my legs, so they were straight in the air.

She folded the diaper open, slid it under my butt and put a bit of powder onto my skin.

I felt a little funny about being naked on her bed, but not too embarrassed.

She put the front of the diaper over my dick and fastened the sides, first the left ones, then the right ones. She double checked that everything was snug. Pretty thick too.

"There we go", she said, "Nice and diapered."

I moved around a bit and felt the diaper under me. It was pretty well fitting and didn't feel all that bad. At least not causes-me-physical-pain-bad.

She stuck on finger in the waistband and pulled a bit, letting it snap back.

„Hm, feels good“, she said, „I was worried that I‘d bought them too big, since I kinda had to guess your size and had to consider that your boner had to fit in there without peeking over the edge.“

She took a look from all sides.

„Buuut, I‘d said these look just about perfect! Feel good?“

My fingers ran over the soft fabric.

„I guess it’s not too bad“, I said, honestly.

She smiled.

"Great. Now, why don’t we lay down a few ground rules to follow here“, she said and I listened, „Firstly, no cumming into anything but your diaper, alright? Not the sheets, the sofa, the toilet or any of our mouths, alright? Just into the diaper.

Secondly, you can jerk off as much as you want. However, you’re not allowed to diaper yourself, okay? Either I or Haley do it, depending on who’s home. Same going for taking the diaper off.

Thirdly, once you’re diapered, you have to keep em on until you‘ve used them. I bought the ones with non-reusable tapes on the side, so I‘d know if you had taken them off. Therefore, once they’re on, they can’t be used again and I will not waste any diapers, okay?

Lastly, as you already know, masturbating has to take place in the living room, alright?

Everything clear? Do you think you can handle all that?“

I stood there and thought about it for a moment.

„Hm, sure“, I said, „Still a little weird, but not too bad. Sounds pretty fair, I think.“

She clapped her hands and smiled.

„I‘m proud of you, trying something new“, she said and hugged me, her big boobs pressing against my nude chest. This was all pretty weird, even for my family.

Just then Haley walked in. She immediately smiled widely and started giggling.

„My my!“, she said in her best British accent, „What a beautiful sight to behold, a mother and her son! May I ask where you acquired these odd undergarments, young gentleman?“

I couldn’t help but blush.

„Shush“, Mom said, but couldn’t help but smile as well, „Don’t make him regret this. Or else you’ll get diapered as well.“

Haley came closer. She was wearing an oversized pastel pink crop top, a bright pink high waist thong and black fishnets up to her thighs.

„Hmm, is your diapee nice and comfy?“, she asked me.

„Uhm, yeah sure“, I said.

„Might just be worth it“, Haley pondered and Mom laughed, „I‘ll have to think about that.“

„Well“, Mom said, „I know you love teasing him, but you don’t have to do that to try some diapers.“

Haley looked a little surprised.

„Really? Me in diapers? I was gonna go out right now.“

„Honey, people can wear diapers going out“, Mom said, „It’s good for a girl’s self-esteem.“

Haley didn’t look all too convinced.

„I think I‘m good“, she said, „Maybe someday.“

Mom proudly inspected her outfit.

„Just saying, you're a hot, young girl who can get away with wearing practically anything in public and you should try taking advantage of that.“

Haley looked herself up and down.

„Am I not?“, she asked.

Mom chuckled and shrugged.

„I don't know“, she said, „I was your age once, so I‘ll tell you, the only things you‘ll regret are the ones you didn’t try. You'll understand when you’re older. So, what's the plan for today? Are you going out with friends?“

Haley nodded.

„Yeah, a few girls and I are gonna grab lunch and do some shopping downtown“, she said, „Should be fun. Maybe a little gay, who knows. Maybe afterwards we’ll just gonna chill and smoke weed.“

„And I didn’t even hear that“, Mom said, „Just have fun, darling. Matt and I are gonna go shopping a little at the mall in 20 minutes or so.“

"Okay", she said, „You have fun too!“

With that, she was off and we could hear her leaving the apartment.

„So what now?“, I asked.

„Enjoy your diaper, honey“, Mom said, „Play some video games, go sit on the couch and read a book, see how it feels. You still got 20 minutes before we go shopping, so jerk off if you want.“

I wasn’t really horny so I probably wouldn’t do that.

„Uhm, how about I put on my normal clothes and underwear and get ready for the mall?“, I suggested.

„Oh, but you know the rules“, Mom said, „No taking it off until you used it.“

I remember and sighed.

„Oh, seriously?“, I said, „So what now?“

„Well, your choice, honey“, Mom explained, „Either you jerk off right now or you use it sometime later and it stays on for our shopping trip.“

Neither option was something I wanted to do.

„Do I really have to?“, I asked, „Can’t we please make an exception for the first day?“

She shook her head.

„Sorry, honey“, she replied, „I‘ll make sure you give diapers a proper try.“