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The bad news was that Grant’s family, for the first time in the twenty years that I’ve known him, decided to make use of their lakeside cabin for the entirety of the summer. It made sense, I supposed. They were retired now, and all their kids had moved out and moved on. Why not spend the summer out of the city and next to a lake?

Of course, this had an impact on Grant and I’s little summer tradition of taking a week off work to go hang out at the cabin. We’d load a car full of booze, pot, DVDs, and video games and proceed to spend seven days in a mildly incoherent fog as we further refined our in-jokes. It was a pretty devastating loss–though our brain cells were probably thankful that they’d be spared the abuse.

But there was good news too. My mother, having heard my despair over the loss of our week at the lakehouse, thought she had an alternative for us. The family of a good friend of hers owned a rather secluded cabin that had fallen into disuse over the last few years. All it took was a single phone call to get them to hand over the keys for a week–as they were just elated that someone would be using the old house again.

We’d be missing a few of the amenities we were afforded at the lakehouse we knew and loved–namely the lake itself–but the opportunity to get fucked up for a week at the low, low, cost of nothing still seemed like too good of a deal to pass up.

We loaded up the car, plugged the address into my phone’s GPS, cranked up some tunes on the radio and set out for another installment of our favorite week of the summer.

===

“This is the place?” Grant asked as I pulled off the dusty old road and into a long driveway.

“That’s what the app says. And there’s a house up there. Like…the only house we’ve seen in the last twenty minutes.”

“It’s not…pretty.”

No, it wasn’t. It was far from dilapidated, but the old house had still seen better days. The paint was faded and chipped. An area that looked like it had once been a lawn was now an overgrown jungle, with weeds and tall grass having swallowed old patio furniture.

The keys were under the doormat, as promised. And, considering the amount of dirt and dust I had to sweep off of the porch first, it was safe to assume that the keys had been here for quite some time–available to anyone who looked, though undisturbed. I found it strangely reassuring that there were no signs of recent human contact. This place really was all ours for the next week.

The inside of the house was nice enough, if not a bit antiquated. Were I to guess, the last time someone put any effort into redecorating was the late 80s. Under a layer of dust, were bold pinks, teals, and creams that were certainly reminiscent of a time before I was even born.

“Kinda ugly,” I said.

“But it’ll do,” Grant shrugged. “There’s electricity, right?”

“I think so.” I flipped a switch on the wall, and some lamps came to life–their amber light illuminating all the dust particles in the air. This boded well for the refrigerator we’d need for all the beer we brought with us.

“Look, as long the place isn’t on fire, I’ll take it,” he said. “All we need is a working kitchen and a couch.”

We had gotten a little older ourselves. In the first few years of our annual lakehouse pilgrimage, it would feel like we only got four hours of sleep in the whole week combined. Now, in advance of the week away, we fantasized about how many naps we’d be taking.

We had a little work to do before we could just relax. Considering how much unplanned time was ahead of us in the week, an hour or two of dusting, sweeping and light upkeep seemed like a small price to pay. And when we finally did get the chance to sit on the couch, cracking open our first beers, it felt earned. It might have even made the beer taste better.

“So whose place did this used to be?” Grant asked.

“A relative of a friend of my mom’s,” I said. “Some old lady, I guess.”

There was probably a story to follow if you studied all the photos hanging on the wall closely enough. Generations of people growing up and growing old, before disappearing. No doubt, there were plenty of memories here–just not ours. It almost felt blasphemous to defile that legacy with bongrips and drunken stumbling, but not enough to stop us.

“That lady over there is pretty hot,” Grant said, pointing up at a large framed portrait of a woman with long brown hair. He wasn’t wrong.

“There’s no way she’s alive anymore,” I responded. “Kind of sad.”

“Yeah, but she probably had kids who were hot. And then they had kids who were hot. You oughta look into that. I’d definitely date that lady’s granddaughter.”

I was tempted to poke holes in his fantasy. Like, how we’d need to consider the genetics of who her children had married. Or if she even had daughters. But, then again, this was the week for fantasy.

“I’ll drink to that,” I said, clanging my can against his.

===

We spent that first afternoon just catching up. That was another of the changes that had slowly worked its way into our annual sabbatical–chit-chatting about what we were up to these days. Time was, we already knew this stuff because we talked to each other everyday. But then we graduated college. Got jobs. Had relationships. In Grant’s case, he had a kid. Now, these weeks were just as much for the two of us to reconnect and review what we’ve been up to for the last year.

Grant’s kid turned two this year, which he found to be ‘the most exhausting thing he’s ever experienced.’ And between parenthood, his schedule at work, and his wife’s schedule at work, he’d never felt more burned out.

I almost felt guilty for telling him my current life story: Work was steady, but not too busy. I was working from home. There weren’t any children keeping me up at night or refusing to eat broccoli. Of course, it wasn’t all easy-breezy–my love life had taken a catastrophic plunge over the last year. After three years together, Christine had left me. I probably should’ve seen it coming–hindsight made all the growing concerns seem glaringly obvious–but her decision to leave had hit me like a ton of bricks.

In other words, I needed this week more than I had ever needed it before.

“Fuck women,” Grant said. It was easy for him to say, considering he was in a relationship that was more committed now than it had ever been.

Still, I laughed and appreciated the support. “Here, here.” Another clank of our cans.

“I promise you, Kyle. This week is going to make you forget all about that shit. This week is going to be killer. It’s going to be legendary. When it’s said and done, it’s going to rank up there with the likes of 2014 and 2017.”

Ah, 2017. The year we met the cute redhead at the seedy bar and proceeded to have her over at the lakehouse for a wild night of illicit pleasures.

“We’re probably twenty miles from the closest bar,” I chuckled.

He shrugged. “We’ll figure something out. Actually, you know what I’m thinking about?”

“Hmm?”

“That chick up there,” he said–pointing up at the portrait of the woman on the wall again. “Just look at her eyes, man. You just know she was a handful.”

Looking at her again, I could see that.

“Look, if you were going to take naughty pictures of yourself, where would you stash them? At home? Or would you hide them at your remote vacation house in the middle of nowhere?”

I couldn’t help but laugh. “You honestly think there’s some homegrown porn stashed away in this house?”

He shrugged. “If I was a hot woman, this is exactly where I’d keep my nudes.”

As ridiculous as the idea was, it was at least amusingly ridiculous. “I think you’re reaching.”

“Over there,” he said, pointing to the drawstring hanging from the ceiling. “That’s the attic. I think we should go up there and take a look. Best case scenario–we find a box of secret porn.”

“Worst case scenario,” I said, “we find dusty old antiques that mean nothing to us. And we get bit by spiders.”

“What else do we have to do? C’mon. Let’s go be nosy.”

===

For a while, it seemed like a complete waste of time. Nobody was bit by a spider, but we certainly weren’t striking pornographic gold either. So far, all we had uncovered were old pieces of furniture, bins of childrens toys and the occasional box of tacky decorations.

“I’m calling it,” I said, tossing aside an old doll with matted hair. “There’s nothing up here that’s worth our time. I brought my Switch, though, and we could be getting stoned and playing Mario Kart right now.”

“Hold up,” Grant said, dragging a box out from behind an old dresser. “I think I’ve got something here.”

It was another box that looked exactly like all the other boxes. “Okay? What makes you think this one is any different?”

“Well, there’s only two boxes left,” he shrugged. “So if there is anything exciting up here, it’s got to be in one of these.”

“Alright,” I said, shaking my head. “Why don’t you do the honors, then. Open it up and see what sorts of treasures you’ve found.”

Flipping open the cardboard flaps, I watched Grant’s hands disappear into the box. They reemerged holding clumps of fabric.

“Ooh,” I said, rolling my eyes. “Clothes!”

“No, no, look!” He held out the garment and let it unfurl, revealing a rather elegant looking blue dress. “Come on, Kyle. You’ve got to admit that if you saw a woman wearing this, you’d think she was pretty cute.”

“Sure. But note the lack of a woman inside of that dress.”

“Shit,” he said, ignoring me as he pulled out another garment–a rather short-looking skirt. “Grandma was a little slut.”

It was a funny thought, even if it was just speculation. We could only guess as to who owned these clothes before. I probably wouldn’t have thought twice if I saw a woman my age wearing these clothes today.

“Dude, there’s all kinds of stuff in here. Panties. Bras. Tops.”

I laughed again. “Man, you can’t be rifling through some stranger’s underpants. That’s just weird.”

“They’re clean,” he said, holding up a pair of black lace panties. “Maybe?”

“Put down the panties.”

“They’re cute, right?”

“Maybe we can set aside some time this week for a seance? We could summon the pretty lady’s ghost and get her to model her panties for us?”

“You’re a dick,” he laughed.

“Go on,” I teased. “Open up that second box. Maybe you’ll find the lady’s hemorrhoid cream.”

He turned his attention to the other box, opening it up and rifling through its contents. “You’ll feel stupid when I find a stack of…” He let out a deflating sigh at whatever he was seeing.

“What did you find?” I asked. “It was hemorrhoid cream, wasn’t it?”

“Maybe even worse than hemorrhoid cream,” he said, holding up some white squarish object.

“What the hell is that?”

“I think it’s a…uh…” He unfolded the object, revealing to both of us what it actually was. “Yeah. That’s a diaper.”

“An adult diaper.”

“Shit. You don’t think that the same person who wore those clothes also wore these, do you?”

“Probably not at the same time,” I shrugged. “People get older. Grandma probably started having accidents or something. Someday, you’ll probably need them too.”

“And hopefully I’m senile enough at that point that it’s my kid’s problem, and not mine,” Grant chuckled.

“Come on, man,” I said, waving him towards me. “Let’s get out of here. We got this out of our system and now we can go and get our week of blissful nothingness started.”

“Yeah,” he sighed, tossing the diaper back into the open box. “That’s probably for the best. That beer isn’t going to drink itself.”

===

I thought that I’d have an advantage. Unlike Grant, I have free time–free time that I often spend playing video games. But he was holding his own in Mario Kart–managing to best me in at least half of our races.

“Looks like you underestimated me,” Grant said, a cocky smile on his face as he tipped a new can of beer into his mouth.

“What the fuck, man. You’re a dad now. You shouldn’t be this good.”

He laughed. “Here’s a little something I didn’t tell you: Emma bought me a Switch for my birthday last year. I’ve been practicing.”

The deceitful son of a bitch. Time was, we’d tell each other every single video game we bought and played. Every new CD or record we were spinning. Every new film we saw in a theater.

“I guess I’m going to have to try harder,” I said, stretching my arms out in front of me to crack my fingers. “I can take out an old man like you.”

“You’re not so young and spry yourself,” he laughed. “Want me to just go and grab you one of those diapers from the attic?”

Some classic shit-talk. It felt like we were 18 again–a feeling only exacerbated by the three beers we had each pounded since coming back down from the attic.

“I’ll show you who needs diapers,” I said, gripping my controller in my hand.

“Yeah? Are we, uh, making a bet?”

Another standard of our week away–the video game bet. My loss in Tekken back in 2017 caused me to spend a night outside without any clothes. Grant’s inability to best me in Forza in 2020 resulted in him having to shave his pubic hair and sending a photo to an unamused Emma.

“Sounds like it,” I said. “Loser of the next race has to wear a diaper.”

“But you can’t just, like, put on a diaper and wear it under your shorts. You’re going to sit here on the couch–no pants and in just a diaper.”

“Obviously.”

My fingers felt a little sweaty as I gripped the controller, and a quick glance in Grant’s direction showed me that he was looking a little nervous himself. There was a lot on the line here. To be humiliated like this on the first day of our week away together? It was going to be next-to-impossible to recover from that. There was a lot on the line here.

Right out of the gate, he’s in the lead. I’m maintaining the position behind him, but it’s hard to find opportunities to pull ahead of him. Some good luck finds its way to me on the second lap, however, when Grant takes way too wide of a turn in an effort to avoid a banana peel, sending his kart careening over the edge of a cliff. Not only does this get me into first place, but it puts a sizable gap between me and him. As we enter the third and final lap, he’s gaining on me, but not fast enough to pass me before the finish line.

I’m feeling good. Maybe even a little cocky. “Enjoy your diaper, bitch.”

But as the words leave my mouth, my eyes catch an incoming projectile. The dreaded blue shell. I have nothing in my inventory. And there’s just enough space before the finish line that I know it’s going to hit me. And, once it does, there’s no hope of recovering my lead.

It goes down exactly as I saw that it would. Grant clinches the win in the final second as the shell connects with me.

“I’m sorry,” he says, his smile twice as cocky as mine was. “What was that you said? Something about me being a bitch?”

“Goddammit.”

“Do you want to go grab your diaper, or should I?”

My diaper. It stings.

“I’ll go get it,” I said.

“While you’re up, you might as well go and put it on, too.”

“Fine.”

“Remember,” he sneered, “don’t try to hide it with pants or anything.”

“I know what the terms were, don’t worry.”

Nothing is forcing me to go fetch an old, possibly deceased, woman’s diapers and put it on. But there are rules to these games. There’s our own personal honor to consider. If Grant had lost, I’d have expected him to wear a diaper too.

Back up in the attic, I grabbed the adult diaper that Grant had previously unfolded and cast back into the box. I still couldn’t believe how big it was. How thick it was. I couldn’t imagine someone walking around in public with these things on under their pants, but maybe these were intended for more severe cases. ‘Medical grade?’ I looked through the box, wondering if there was any additional packaging, but all I found were stacks and stacks of disposable white adult diapers like the one I was holding in my hand.

I felt sad again, thinking about who these might have belonged to. Someone once thought all these would be needed–only to have them relegated to a forgotten attic. Who knew how long it’d be before someone finally came along and did something with the rest of these.

Diaper in hand, I went back down to the main floor.

“Get your diapy?” Grant asked from the couch, his voice steeped in condescension.

“Yeah,” I muttered.

“Do you need help?” he asked. I thought he was joking, but there was a hint of sincerity in his voice. But it was such an absurd question that it had to be a joke. I wasn’t about to ask my best friend to diaper me like an infant.

“I think I’ll manage.”

“I’m just saying, Kyle. I have a two-year-old. Do you know how many diapers I’ve changed? I’m a goddamn diapering expert.”

I still wasn’t about to take him up on the offer, but I was curious as to how serious he was being. “You’re really going to come over here and put a grown man in a diaper?”

“I dunno. Do you really want another grown man to put you in a diaper?”

We were in a strange stand-off, where neither one of us seemed willing to admit that we were the one bluffing. How far could it go? Would I be on my back, legs kicked up in the air with pants off, before one of us finally admitted that we were just joking?

I decided not to find out. “I’ll be back in a few minutes,” I said, taking my diaper to the bedroom I had thrown my stuff in earlier and closing the door behind me.

===

When asked, Grant and I would both claim to be straight. And that would be, mostly, true. He was married to a woman. I had only ever dated women. When I finally decided to put myself out there to date again–and I was probably a little overdue for that–I’d be looking for another woman to have a relationship with.

But we were both curious. And I knew that because we had both been curious…together.

In the summer of 2016, we gave each other handjobs while tripping on shrooms.

In the summer of 2018, Grant had sucked my cock. As tempting as it is to say that we were in some state of inebriation, I don’t think that’s what happened. It was late at night, the fire pit was roaring, and we got to talking about what sexual curiosities we had. Grant said he wanted to know what a cock tasted like, and I, jokingly, offered him a taste–not thinking he’d actually take me up on that. Soon after, his head was between my legs.

To this day, it was one of the best climaxes I had ever experienced.

Last summer, as I climbed out of the lake on the last day of our week away, his hand stroked the front of my swimsuit, causing a tent to form. Soon after, my hand was on his pants too, and then our lips were on each other’s. It was messy and fumbling. Kind of awkward too. But it didn’t feel wrong.

We never talked about these incidents after the fact. I wouldn’t say that we were in denial about them–we just didn’t have anything to say. Speaking for myself, I never felt any sort of guilt or regret. It was just another part of our friendship.

I wondered if there was a small part of us that kept setting up these weeks away with each other, summer after summer, because we were just hoping something like that would happen again.

I thought about that as I lay on the bed, naked below the waist, with a diaper in my hands. The hell if I knew what to do with this thing. What side were the tapes expected to go? How tight was it supposed to be if I even got it on?

It was tempting to just power through and figure it out. Surely, there were plenty of adults who needed diapers that were capable of handling this themselves. But, then again, if these thick things were actually ‘medical grade,’ it implied that there’d be someone like a nurse involved in helping to apply it.

Fuck it. If this was just the start of our week, there was no doubt that there’d be some escalation in our antics before the end of it. I figured I might as well swallow my pride and see what happens.

“Hey, uhm…Grant?”

“Yo.”

To my surprise, his response came immediately–and from the other side of the door. He was already there. Waiting.

“Were you being serious about…helping?” I felt so pathetic for asking. I felt small.

His answer was simple, and his tone devoid of any teasing: “Yeah.”

“Why don’t you come in, then. I have no idea what I’m doing.”

I thought, too late, that I should make an effort to cover myself up. Because, as it was, my half-naked body was splayed out on the bed–facing the door and leaving nothing to the imagination. But then the opened, and Grant was looking down at me. And I was pretty sure that he was seeing more of me than he had ever seen before.

“Hello there,” he said, his eyes fixed on my cock as if to say ‘Remember me?’

“We don’t have to make a big deal about this,” I said.

“About what? Me walking in on you with your pants down so that I can put you into a diaper? I feel like it’s kind of a big deal.”

“C’mon,” I sigh. “Are you gonna do this or not?”

To my surprise, and relief, Grant just nodded and went to work without any further quips. My hand extended towards him, giving him the shameful garment. He took it and placed it on the bed between my legs, smoothing and flattening it out.

Regardless of how many diapers he may have had to change for his own baby, I didn’t think that experience would directly translate to having to put a grown man in a diaper. However, he seemed to have no trouble with it. He lifted my legs into the air to raise my ass up for a moment so that he could slide it under me. Having a man–Grant, in particular–effortlessly move my body around was rather…stimulating. Moreso than I could’ve predicted.

“What’s this?” he asked, poking at my stiffening cock.

“I, uhm…”

“I can’t put you in a diaper when you’re like this, Kyle.”

“Maybe… Just give me a few minutes.”

“Does this turn you on, Kyle? Getting diapered by your best friend?”

I considered lying, or at least downplaying the truth a little bit. But there didn’t seem much point in that. If I couldn’t be honest with Grant, who could I be honest with? Besides, I didn’t think he’d mind the truth.

“I don’t hate it,” I finally said. “And it’s not the diaper itself, I think. It’s, you know, the act of being…manhandled a little.”

His hand wrapped itself around my cock, getting a good grip on it. “So if I get a handle on your dick, is that considered manhandling?”

We both laughed, even if my laugh was a little more distracted sounding than his. I was breathing heavy. I felt a moan being summoned up from my throat, ready to be uttered if he moved his hand even the slightest bit.

It moved–he gave me a playful little tug. “Uhhhfff…”

“Do you like that?” he asked.

All I could do was nod.

“Let’s do it again, then.”

He slid his hand up and then down my shaft, my back arching into the air to thrust my cock a little closer to him as I moaned aloud.

The situation we found ourselves in almost seemed to have come out of nowhere, but just the slightest bit of reflection would remind me that this probably wasn’t the case. For the last few years, it always felt like we were just a moment or two away from ‘experimenting’ again. That’s what we called it, in those rare moments when we were both sober and willing to talk about the things we had done with each other–’experimentation.’

The tension had been there in the car on the way to the house. Occasionally our eyes would meet as we talked, and I could see him looking at me in a very particular way. Like he was calculating what the first opportunity would be where we could take our clothes off without it being awkward. And I knew this because I had been trying to calculate the same thing.

In the past, our experimentation had just been limited to short, isolated, moments. Late night trysts that came after hours and hours of subtle poking and finger-crossing. But this moment, in the broad daylight and our very first day away with each other, suggested that this might end up being a very different kind of trip.

“Do you like that?” he asked, his hand continuing to slide up and down my cock.

“Wh-why would you, uhff, even ask that?”

“Maybe I want to hear you say it.”

I let out another long moan as I felt his hand increase its pace a little.

“Go on,” he said. “Tell me you like it, baby.” But ‘baby’ was broken down into two hyper-exaggerated syllables: bayyyyy-beeee.

It almost made me mad that this was working for me. I had spent an entire year daydreaming of what sort of trouble we might get into when left to our own devices–only to find myself getting pleasured in the middle of having him put a diaper on me.

“I…I, uhm… I like this.”

“Thought so,” he said as he stared down at me with a smug smile on his face. It was evident that he was enjoying this as much as I was.

It wasn’t much longer after that when I erupted–spurts of white lazily spilling out of my cock and coating his hand. Were I in a different state of mind, I’d have apologized for making a mess. Instead, I was paralyzed by pleasure, and I just remained still on my back as I felt all my nerves firing at once.

“Impressive,” he said, lifting his hand up to his mouth to taste the dripping white cream. “I, uh, missed that taste.”

It was good to see his cheeks turn red. It made me feel like I wasn’t the only one trying to wrap my head around how naughty all of this felt.

“This is going to be an interesting week, isn’t it?” I finally asked.

“Oh, for sure,” he said, grabbing tissues from a nearby box so that he could wipe clean his hand and my wet cock.

“Y-you’re still going to, uh, put that diaper on me, right?”

He smiled. “That was my plan. You still want that, yeah?”

I nodded.

“Good. Yeah, let’s do that. You’re looking a little limper now. I think this’ll work just fine.”

A man of his word, Grant finished what he started. He pulled the front of the diaper through my open legs, smoothing it out over my shrinking cock before pulling the taped sides of the back of the diaper forward so he could fasten it all together. Ah, so this is how it’s supposed to work. He carefully and deliberately pulled each tape tight before applying it, leaving me sealed in the thick plastic undergarment.

“What do you think?” he asked.

I sat up, immediately taking note of the crinkly nature of the diaper’s outer plastic shell–not to mention the new thick bulk between my legs.

“This thing is really big,” I replied, my hands pawing at the padding.

He reached down to feel for himself. I usually needed a bit of time to recover after having climaxed, but feeling his hand press against my cock–the padding of the diaper between the two–almost got me going again.

“It actually looks good on you,” he smiled.

“Good?”

“Cute?” he shrugged. “It definitely looks cute on you.”

“There’s a lot of them up there,” I said, pointing up to the attic above us. “If you walk me through it, I could probably get you in one too.”

“Tempting. But, you’re the one who lost the bet, not me.”

“There’ll be other bets,” I said. “Sooner or later, you know I’m going to get you into one too.”

“Sure,” he shrugged. “I could see that happening. But…don’t you think the little baby needs someone to take care of him?”

I felt my cheeks warm considerably. I must’ve looked as red as a tomato. “I know I’m wearing a diaper, but I’m not a…”

“You’re a baby,” he said. “And I think you need to admit that you like that.”

“Look, I…”

“Tell me you’re a baby, Kyle.”

It felt like part of a proposed deal. “And if I do? What do I get?”

“You get me taking care of you.”

I wasn’t entirely sure what that meant, nor could I guess how far this game would go, but I did like the sound of it. He had just shown me with his hand, moments before, that he was very capable of ‘taking care of me.’

“I’m a baby.”

“That’s a good boy.”

Fuck. That just about took my breath away.

He took me by the hand and helped me out of the bed. Instinctively, my first thought was to reach for my discarded pants.

“Leave ‘em,” he said.

“You want me walking around in just a diaper and t-shirt?”

He smiled. “C’mon, baby. Let’s go grab another drink.”

It was wild how quickly the feeling of walking around in a diaper started to feel normal. Sure, I wasn’t sure that I was going to get used to the feeling of the mass between my legs, or the way that it crinkled and rustled whenever I moved, anytime soon. But it felt surprisingly natural to just waddle about in the thick padding. And…kind of nice.

We cracked open some more beers before settling back down on the couch again. And, ignoring the diaper for a few minutes, we fell into the old routines like we were 18 years old again. I showed him some of the other games I had been playing. He told me about some of the games he wished he had time to play. We shared a few more anecdotes about our recent lives. We played a quick round of ‘Do you remember that guy we used to know who…?’

And then I felt that all-too-familiar call of nature. I was a little surprised it hadn’t happened sooner. Between the deluge of beer we had consumed since setting foot in the cabin, and my recent handjob in the bedroom, I’d have thought I'd have been bursting at the seams a lot sooner.

“...and now, of course, you have to factor in the extra costs you didn’t have to think about before,” he was saying. I was pretty sure he was talking about family vacations now.

I was torn about what to do next. Did Grant actually expect me to use the diaper? More importantly–did I want to use the diaper? Just how much of a commitment were we making to this bit? Would he have been offended if I just walked to the bathroom?

I could almost imagine how that conversation would play out, too. “Kyle, why are you going to the bathroom?” he’d ask. “Did you forget that you’re wearing a diaper?”

Or maybe that was just what I wanted him to ask.

“...but, I dunno, I think it all ends up being worth it,” Grant continued. “Like, he’s barely two and I can still look back at photos of him a year ago and it feels like a completely different world.”

There was some hemming and hawing taking place in the back of my head as we talked. And the longer this went on, the harder it got to maintain both the conversation and the inner debate.

The solution seemed rather obvious. Fuck it. Let’s just do it and see what happens.

I’ve always been kind of pee shy. The type who would sooner zip up my pants and leave the restroom without having done anything because another man was at the urinal next to mine. And so I thought this would be a struggle. I thought I’d be groaning and grunting as I tried to force myself to piss. But no. I didn’t really have to do anything–I just stopped doing what I already had been. Holding my bladder. My body did the rest for me.

Grant shrugged as he seemed to be wrapping up his little monologue. “They just grow up so fast.”

I wasn’t entirely sure if it was just because I was in a place I wasn’t supposed to be–wearing a garment I wasn’t supposed to be wearing–or if I just really had to go. But it was one of the most incredible pisses I had ever taken in my life. The relief seemed to wash over my body as I emptied myself into the diaper–which grew warm and swollen between my legs.

For a brief moment, I thought I had gotten away with something. Like I was going to be allowed to just keep having my normal conversation with Grant like I hadn’t just pissed myself in a diaper.

But I should’ve known better. The second I finished wetting myself, I felt Grant’s eyes on my crotch, studying the color and texture of my padding.

“You pissed yourself,” he stated, rather matter-of-factly.

“N-no…” I had no idea why I lied about it. Why did toddlers lie about having gone to the bathroom in their pants? Was there some inherent need to protect ourselves from our caregiver’s disapproval?

“Kyle. That diaper is soaked.”

I sighed. “S-sorry, I…”

“I can’t believe you did that.”

Was he…upset? I really couldn’t tell. “Look, I’ll clean up after myself. I just thought that…”

“No,” he chuckled. “I was hoping you’d do that, but I didn’t think you were going to. Hell, I thought I was going to have to end up begging you.”

“Really?”

He reached between my legs, stroking the warm bulge. “You are such a naughty baby boy, aren’t you?”

“Nuh uh,” I said, so softly that I almost wondered if I was actually shrinking for a moment. “You told me I was a ‘good boy.’ Remember?”

He laughed, squeezing my diaper again. It forced a little pathetic noise out from my lips: “Muhh…”

“I suppose you’re a good boy for using your diaper like a baby.”

“That means you have to change me now, doesn’t it?”

“Kyle, I just put you in that diaper.” The cadence of his tone suggested that this was something he had probably said a million times in his life–though, probably, to an actual toddler.

“I know, but…”

“Is it mushy?” he asked.

“Mmmhmm.”

“I bet you like the way it feels,” he said, his hand squeezing my diaper again. I could feel some of the warm liquid that had been trapped in the padding squeezing out and trickling down my cock again. “Don’t you?”

“M-maybe.”

He bit his lip, and I could almost see the conflict in his eyes. Sit here on the couch and enjoy this moment a little longer? Or go back to the bedroom with a fresh diaper–ready to start a new moment?

“Let’s get that diaper changed,” he said. “Again.”

We slid off the couch and began to make our way back to the bedroom again, though our paths diverged just as I reached the door.

“Where are you going?” I asked.

“Back up to the attic,” he said. “I’m assuming you didn’t bring down extra diapers when you were up there?”

“Uh, no.” It was surreal–I hadn’t even considered this possibility when I had gone up there to grab one earlier.

“No worries. Why don’t you just go and lie down on the bed. I’ll be down in a minute and we can get that sopping-wet thing off of you.”

I opened my mouth to say ‘thank you,’ but he was already ascending up the ladder into the attic. What else was there to do but go to the bed and await his return? I did as he had asked me, lowering myself atop the bed. I remembered how his hands had positioned my legs earlier when he was putting the diaper on me, and I tried to mimic it myself–spreading my legs a little and lifting them into the air.

Well damn. Just having my legs kicked up like that, and hearing the wet diaper rustle as I moved about, made me feel incredibly small.

I wondered if it was the beer talking, or if there really was something about this pissy diaper that was driving me wild. It was just so thrilling. So naughty. Immature. And just the concept of this role–being so pathetic and helpless that I needed my best friend to help me. My heart pounded as I reached between my legs and grabbed at my squishy padding. He better fucking hurry up, or else I’m going to end up creaming my diaper.

But as my one hand clumsily rubbed at the front of my diaper, the other felt restless, tapping on my thigh. The longer it took for Grant to come back, the more I began to wonder if this wasn’t actually all that good of an idea. I needed to do something with this nervous energy. I needed to center myself.

Think like a baby, I told myself. I wasn’t entirely sure what that meant, but…

Wait. Babies don’t think. Now that made sense to me. I just needed to stop thinking so much.

I took a deep breath, held it, and released it. And then the answer seemed incredibly obvious. I stuck my thumb in my mouth, and I began suckling on it.

I had a problem with sucking my thumb when I was younger. I remember my mother pleading with me to stop sucking my thumb because the other little boys in second grade weren’t sucking theirs anymore. I couldn’t say when I actually gave it up–maybe it was that conversation, or one like it, that finally convinced me to move on. But the feeling of the thumb in my mouth now reawoke whatever pleasures I felt when I was younger and doing this. It was so soothing. So…blissfully perfect. I just wanted to do it all day.

Grant did seem to be taking a while. But whatever. He could take all the time he wanted, because now I was good and pacified.

“Sorry it took so long,” I could hear Grant say as he approached the bedroom. “But I wanted to play dress-up too.”

I quickly glanced towards the door, expecting to see him glide through the threshold in a thick diaper of his own. But no. He had gone through the other box it seemed.

He was wearing a dress–a little summer dress, I think–that might have been a little too small for him. It seemed a little too tight in all the wrong places, and the bottom did almost nothing to hide the rather obvious lacey panties he was wearing.

My thumb slowly slid out of my mouth. I wanted to say something more meaningful, but all I could muster was: “Oh. Wow.”

“Do you like?”

I didn’t hate it at all. If the dress fit a little better, and if he was missing the stubble on his face, I could see him making a rather pretty woman.

“I…I do,” I nodded.

I loved it. Our freak flags had officially been flown, and we were jumping right into the deep end.

“I’ve been thinking about these clothes ever since we saw them up there,” he said.

I tried to stifle a little laughter. “A-are you wearing…some dead lady’s panties?”

He laughed and shook his head. “Do you like these panties? Honestly?”

I nodded. “They are cute.”

“They’re Emma’s,” he said. “I brought them from home.”

“Oh. So…you’ve done this before?”

He shrugged. “Maybe a little.”

“You brought them? W-were you going to show me?”

“I don’t know,” he said. “Maybe. Depending on where the week took us.”

“Well, apparently it took us right here. Diapers and panties.”

“It’s not weird?” he asked.

“Oh, it’s very weird. But in a good way.”

He stepped towards me, the bottom of the dress billowing as he moved. From my angle, I could see the edge of his panties beneath the hem.

“Now then,” he said. “Some little boy has a dirty diaper?”

“Maybe…”

“Maybe? Little boy, if that diaper were any wetter, I’d need a lifejacket to get closer to you.”

We both cracked up. It felt good to laugh about it, really–there really wasn’t a way to take any of this too seriously. This was already the weirdest thing we had ever done together before, and I had no doubt that it was going to get weirder by the week’s end.

“Uh, so… Earlier when we were on the couch? And you were, like, feeling my diaper.”

“Mmhmm?”

“I… Well, I was going to call you ‘Daddy.’”

Grant’s eyebrows raised a little. “Oh yeah?”

“But, uhm, given this little outfit change, I’m wondering if…”

“Do you want to call me ‘Mommy?’” he asked, a look of eager anticipation on his face.

“Would you mind if I did?”

“I’d love that.”

My voice got softer again, as I felt my heart beating incredibly fast. “Change my diaper, Mommy.”

“We’re missing some of the things we need to take care of a baby properly,” he said as he began to peel back the diaper’s tapes. “We need wipes. Baby powder.”

“Baby powder?”

“You don’t want to get a diaper rash, do you?”

“Oh.”

“And you’ll need a baby bottle. And a pacifier–don’t think I didn’t see you there sucking on your thumb.”

My cheeks blushed as he pulled open the front of the diaper, revealing the yellow-stained padding within.

“There’s that little town we passed on our way here this morning,” Grant said. “I think I saw a grocery store there. How about tomorrow morning we make a little trip over there and see what we can find?”

“Yeah,” I nodded.

“Do you think anyone at the store would suspect that the baby supplies are for you?”

I felt my cheeks growing warmer. “I…I doubt it.”

He shrugged. “Maybe I’ll let them know. Maybe, while we’re checking out, I’ll make sure to tell the clerk that I need these things so that I can change your dirty diapers.”

That was simultaneously the most embarrassing thing I could think of, and the most exciting thing I could think of. “I hope you do say that. And I’ll be sure to thank Mommy for taking good care of me.”

He sighed and shook his head. “We are fucking insane.”

I reached down to my open diaper, grabbing at my rock-hard cock. “Yeah, but…”

“Yeah, I’m pretty fucking hard too.”

I swallowed hard, feeling vulnerable as I prepared to lob out a question that I wasn’t sure how he’d react to: “H-have you ever wanted to, uhm…”

He tilted his head. “Wanted to…?”

“Like…the two of us? If we just, uhm, were…together and we…”

A smile grew across his face. “Kyle, are you asking if I’ve ever wanted to fuck you?”

I nodded, my cheeks so incredibly hot.

“I’ve thought about it a lot,” he said. “There are days where it’s all I think about.”

“Good. I think we’re on the same page then.”

“Do you want me to fuck you, Kyle? On top of your wet diaper?”

“I really do.”

He unzipped his pants so quickly that I almost didn’t realize he was doing it until his erect manhood was suddenly dangling between his legs. I wanted it so badly. I didn’t care what he did with it, or where he put it…I just wanted it.

“I, uhm, have lube,” I said, pointing to my bag.

He chuckled. “You saw this coming?”

I shrugged. “Wishful thinking?”

“I brought lube too.”

We were cracking up again. Tears were welling in my eyes and slowly rolling down my cheeks as I felt his hands on my thighs. This sobered me right up. I felt my back arching, and I seemed to be thrusting my ass up into the air hungrily. Take me, it seemed to say. Fill me up.

When we were finally ready, it started extremely slow. His lubed-up shaft poked at my backdoor a few times before finally sliding in. I took it little by little. Every millimeter felt like he was pushing me to my limit. He’d remain still, and I’d acclimate–the tightness becoming pleasurable. And then he’d get a little deeper. Repeat.

He wasn’t completely in when he lost control of himself. The combination of being inside of my ass, and looking down at me while he grabbed my cock, had proven to be too stimulating. He was suddenly spurting, filling my asshole with his gift. It was such an extraordinarily amazing feeling that I was soon braying and moaning myself as I dripped and oozed onto his hand for the second time that afternoon.

Soon after, he collapsed beside me on the bed. We were on our sides, and he spooned me. I felt a slow and wet trickle from my bottom as I leaked his sperm onto the bed. I didn’t care.

Sure, we had just fucked–the culmination of years of escalating sexual tension–but this was still the most intimate I had ever felt with my best friend. Feeling his strong arms holding me close to him, the warmth of his body on my back–it felt perfect.

“Tomorrow we go to the store,” he said.

“Right.”

“You’re going to wear diapers there, right?”

“I’m going to wear diapers for the rest of the week.”

“I hope you mean that.”

“If you see me go near a toilet, I want you to pull me over your knees and spank me.”

“I might just do that anyway.”

“I won’t complain.”

He moaned, slowly stroking my arm. “That’s a big commitment, baby. Using diapers all week? You know what that entails, right?”

I shrugged. “I think.”

“Are you going to make stinky diapers? Push some big loads into the seat of your pants?”

“Are you going to change me?” I asked.

“Absolutely.”

“Then I’m going to completely load some diapers for you.”

“That’s a good boy,” he said, leaning forward and kissing the back of my head.

We had an entire week ahead of us, and it felt like we had already fulfilled more of our sexual fantasies in one afternoon together than we had in all the other summer trips combined. Things were going to escalate this week, no doubt about it. Out here, in the middle of nowhere and with nobody to hold us accountable, things were only going to get crazier. By the end of the week, I wondered who we’d be. Because a week like this–I could see it changing us.

“What are you going to tell your wife when we go back home?” I asked. “Like, if she asks what we did this week?”

He laughed. “You know, she rarely asks. I think she just assumes we do, like, boy stuff. Boys being boys.”

“Is that what this was?” I asked. “Boy stuff?”

“Well, you’ve got boy stuff leaking out of your bottom now, don’t you?”

I snickered and slid backwards a little, further closing the gap between our bodies. There was no point in daydreaming about what life would be like after this week–not while I still had to experience this week. So instead, I started daydreaming about the next few days. Sitting on Grant’s lap. Him changing my diaper while wearing a dress. Touching his cock through a pair of silky panties. The feeling of him pushing a baby bottle nipple into my mouth. The feeling of pushing a smelly load into the back of my diaper as Grant watched me.

It was just boy stuff. Perfectly normal boy stuff.