Friday Night Adventures [Archive] (Patreon)

I had been looking forward to Friday night all week. Finally, a night where I’d have some time and privacy to myself, which I fully intended on taking advantage of. All week, while toiling away at work, I’d daydream of all the naughty mischief I’d get myself into.

Of course, by the time we got to Friday, I found myself feeling a bit exhausted. My spirit had been broken by the long week, and I had surprisingly little motivation for anything, let alone feeling naughty. In anticipation for the night, I had even ordered new diapers, which had arrived that day,  though I couldn’t even bring myself to open the box.

My mood slowly begins to change as the night progresses, however. I have a beer or two, I find myself looking at pictures and watching videos, and by the time I start talking to her, I’m slowly building some motivation for myself. Ma’am. Madame. Mistress. She’s a friend - but she’s more than that. She’s the devil on my shoulder, an online presence that takes such delight in tormenting me.

Still, I have low expectations. At best, I figure, I’ll shove a plug in my ass or I’ll just wet a diaper. Truth be told, I had pissed myself in a pair of cotton panties earlier in the week, so a wet diaper doesn’t seem incredibly thrilling, but I’m not sure that I have the patience for much else.

I figure that I’ll offer her my two less-than-stellar ideas and see what she says. Last time I did this, she opted for the unspoken third option of “both,” and while I’m aware that this could happen again, I’m not entirely against it.

“Butt plug, or diaper?”

“Both. Obviously.”

I called that. But she almost immediately suggests suppositories as well - which would make for a much (much) more involved evening. I’m tempted to say no, but her interest and attention has a way of casting a spell on me and I find myself suddenly fully committed. So committed, in fact, that I find myself volunteering to run to the store to buy some, despite it being close to 11:00 at night.

She agrees that this is a good idea, though, adding: “...and that ass better be padded before you leave. I’m thinking one of your old cheap diapers as a stuffer and one of your new diapers on top.”

“But...that’s going to be pretty thick,” I whine.

“Of course it is. That’s the point, silly baby.”

Her words cause my cheeks to blush. The irony in her calling me a “baby” is that she’s much younger than I am, and there was a time when I had even played the “daddy” role for her. It was hard to say what changed, or when, but if I was to guess - it was moments like this; my pathetic aptitude for submissiveness, combined with her twisted delight in watching me humiliating herself.

“Chop chop,” she says. “You’re in for a night.”

I prove to her that I’ve been double diapered before I walk out the door, and it's in my walk to the car that I realize just how hard it is to walk with two relatively thick diapers on. I literally cannot touch my knees together.

At the store, I quickly waddle to the suppositories. I’m very self-conscious of the size of my ass, not to mention how my walk may look to others. Though, to what degree anyone else would be able to notice isn’t clear, but at least it's pretty late and there’s barely anyone around.

Per her request, I quickly send her a photo of my bottom while at the store, extra thick and round from my diapers. My pants could barely be pulled up over them - a fact that she is all too happy to point out herself.

I’ve only been home for a minute when she says “Let’s get a couple suppositories up that cute lil behind.”

I remind her that once they’re in, I don’t think I’m going to last very long before I have to go. This doesn’t seem to bother her at all. In fact, she adds: “And we better get that butt plug ready as well.”

I show her a picture of the suppository that I’m about to slide into my bottom, and she asks that I make it two. I’ve never done two suppositories at once before, and I’m a little nervous about it, but once again, I’m her toy for the evening, and I intend to follow the commands I’m given. With little hesitation, I manage to pull down my diapers and both suppositories are up my bottom. Followed by the well-lubed butt plug. I share with her a picture of my bottom, plug sticking out of it.

“Here’s the plan,” she advises me. “I want you to wet that cute little diaper and then I want you humping it. But I don’t want you climaxing in your diaper just yet. We’re going to see how long you can last with that cute little plug in.”

I’m a bundle of nerves. There’s a lot happening at once, and it's almost overwhelming. “I assume you want to know if...anything is going to happen?”

“I sure do,” she says. “Don’t you dare finish yourself off. And that butt plug better not come out until I say so.”

It’s not much longer after this that I feel the need to wet. I don’t bother holding it, and I flood the inner diaper almost immediately. As promised, I proceed to hump my wet diaper, being sure to both tell her about it and show her.

It’s 12:15 at this point, and I can feel the suppositories taking hold. I’ve used them before and I know...once these feelings start, it gets worse very quickly.

“It’s...getting stronger.”

“Let’s see if you can last until half past.”

“But that’s so long!”

“Oh, it's only fifteen minutes, baby boy. I know that’s a super big number to count to for tiny babies, but don’t worry, I’m here to take care of it.”

“Yes...ma’am. But...what happens if I don’t make it?”

“I guess if you don’t make it, a little boy will have to go and smack himself on his messy little diaper bum, hmm? And you won’t be allowed to touch yourself either. So I suggest you try.”

But no amount of concentration is helping. I’m losing focus. I’m pacing. My bottom is getting loud and gassy. I feel like I’m going to explode and that I’m not going to make it. It’s 12:26, and while I know it’s only 4 more minutes, it might as well be another hour.

“If you can’t make it,” she says, sensing my plight, “I want you to beg me to let you mess your diaper.”

“But…”

“You better be fast if you want permission.”

“Ma’am, please. Please. Let me…”

“Let you what?”

“Please let me go poopy in my diaper for you, ma’am.”

“Ahh, such a good baby for me. Get that diaper all mushy.”

I jam my hand into the back of my diaper and extract the plug, throwing it aside. I debate on how I want to do this, and I decide that maybe I should share this experience the best I can. I squat down on the ground, my phone positioned up at my bottom, and I record the exact moment when I erupt into the diaper. With a loud sticky noise, I can feel my thick diapers bulge out as a moan escapes my mouth. It comes in a wave or two.

“I...I did it. I made a really big mess.”

“Good boy. But you know what messing before the time means, yes?”

“But! But I messed after 12:30,” I say, looking at 12:32 on my phone.

“But you begged and got permission before, yes?”

“Yes…”

“I want 20 spanks on that messy bottom. And video of some of it, if not all of it.”

I send her the video of me messing my diaper while I grab a large wooden spoon from the kitchen. I make a new video of me giving myself 20 firm swats on the back of my messy diaper. Admittedly, I didn’t think I’d feel much through two diapers...but I had vastly underestimated how much worse the spoon’s strikes would make the mess.  I feel it spread across my cheeks, and filling in every crevice that it can.

“Are you going to do humpies and make a sticky in your diaper for me now?”

“Yes,” I say, deciding to add: “Please? May I? I want to make stickies in my messy diaper for you.”

That was the moment, of course, that I reached peak little space. She always manages to help me find it.

“Such a smart boy, begging for stickies. Yes, baby. Go ahead.”

I do as she asks, rolling over and humping the floor in my filthy diaper. My thumb is in my mouth. I’m moaning. Somehow, I find the right rhythm and position on the ground, and I manage to explode into my diaper.

“It’s done…”

“Oh good. Why don’t you go again?”

“Oh...I couldn’t...as much as I wish I could…”

“Oh no? Why not? Hm. I think you should try for me.”

“I...Ok. If it would please you.”

“Good boy. You might surprise yourself. Afterwards, you can change. But I want you padded for bed, stinky boy.”

“Yes, ma’am.”

And, despite my apprehensions, it's actually easier than I thought it would be to reach climax again. And as my senses slowly come back to me, I find myself sitting on the floor in my messy, wet, sticky diaper. My hands shoved down the front of it. I’m a humiliated mess, and happy for it.

I change into a fresh diaper for bed, and we continue chatting, the conversation turning to more benign things before she admits that she’s been watching and re-watching the video of me messing the diaper. I blush again, though I’m happy that I wasn’t the only one pleased with how the night ended up going.

Later, I’ll tell her that it's her turn next. She doesn’t seem to believe it. And maybe she’s right; I’m far from an intimidating Daddy figure, and she seems to have lost any respect for my authority since she’s learned how easy it is to convince me to fill up some diapers for her. Our conversation ends with her asking me if I own an enema bag. I tell her no, and she asks if I want one.

I sigh, already anticipating next Friday night.

This is a heavily edited and revised version of a story published elsewhere on the web a few years ago.