At Her Service - Chapter Two (Commission)

Thanks so much to our Platinum-Tier patron Matt for commissioning this one!

***

Okay, maybe this is getting a bit out of hand.

It's been a week now, I guess - one entire week since that day when Abby first let me start touching her. And yes, since the humiliating day when I'd ended up pissing my pants in front of the biggest crush of my life. There are moments from that day that I don't think I'll ever, ever in a thousand years be able to forget...

I can still see it: that curious expression on her face as she glanced up at me, then down at the rapidly growing dark stain trickling down my jeans. "Matt - what the hell? Are you actually- are you pissing yourself? Eww, what the hell's wrong with you?!" And yet in her eyes there had been something else, too - something that I only now am beginning to understand.

I'm pretty sure now that it was a gleam of interest. A gleam that showed just how much she actually liked having a guy like me losing control in front of her. Honestly, there's no other explanation I can find for what happened afterward.

It was like some bad porno, really. Not that I know what those are like, of course. But, you know, a guy hears stories... I'd emerged from the bathroom in my towel and fled to my bedroom - only to discover her, still wearing nothing more than her skimpy halter top and shorts, leaning casually against my closet door.

"Hey, Matt. You really are something, huh?" Abby drawled, glancing over at me with a wry smile on her lips. "Who'd ever have expected to see a guy so excited to give little ol' me a back rub that he pisses his pants?" She chuckled and tossed her blonde hair lightly. "Honestly, boy. Whatever am I gonna do with you if you're gonna have accidents every time you're near me? I don't suppose I need to find diapers big enough for a great big boy like you, do I?"

My face felt like it was on fire. Here was the girl I wanted to impress more than anything, laughing at me and joking about putting me in diapers like a baby. "N-no," I remember stammering hastily. "It was just- You know, I just had too much to drink, and-" "Sure you did, Matt. Sure you did," she grinned with a wink. "But you're sure you don't need a diaper? I mean, jerking off over my underwear... pissing your pants... What else can I do with a guy who keeps making his pants wet, anyway?"

"Anything," I'd blurted, tugging fitfully at my toweled waist. She was disgusted with me, clearly. I had to smooth it over somehow - show her I liked her - let her see I wanted to please her- "Oho?" She'd asked, her eyebrows raised in surprise. "Anything?"

Yeah. I guess now that I shouldn't have been quite so enthusiastic in saying yes.

You see, it was only a few days later that I discovered what Abby had in mind. I didn't think too much of the boxes that arrived in the mail room for our dorm; after all, Abby was constantly buying shoes and lots of other crap online. But it wasn't more than half an hour after she got back that evening that she called me away from my readings and into her room.

"Look, Matt," Abby enthused. She was seated on the bed, wearing nothing but one of her incredible bras and her gym shorts - and yes, she looked hot as hell. "I got a few things for you the other day! You know, after your silly accident? I know you said you'd do anything for me, and, well..." She giggled softly. "Maybe I went a little bit overboard. But since you were so sweet, I thought I'd take you up on that offer..." She got up and bent close to my ear. "...See, I want you to help me live out one of my deepest, darkest fantasies. I bet you'd like that, Matt, wouldn't you?"

My trousers were straining, my stiff cock already twitching with excitement to see and hear and feel Abby so close. I hadn't the slightest idea what she meant, of course - but with pounding heart, I nodded. "Yes, Abby," I whispered, a fluttering nervousness in my chest. "Sure, I- I'd like that..." I mean, who wouldn't want to help a bombshell like her with some sexy fantasy?

Not that I was remotely prepared for what she pulled out of that box on her bed.

"It's perfect for you," she purred, holding the black-and-white garment up to the light with a sexy grin. "You know, I love how much work you do around the apartment, Matt! So I thought, why don't we give you the sort of outfit that shows everyone what a good worker you are? How hard you work to take care of me?"

Well, what the hell could I say to that? "I-I dunno... J-just around the apartment, right?" I stammered as she began undoing my shirt buttons with those satiny soft fingertips of hers. "Of course, baby," she breathed - and I nearly fainted. "Just think of it as our own private Halloween party, okay? You're going to be my adorable little housekeeper, just like I've always fantasized..."

I may be an idiot sometimes - but even I know enough not to interrupt a sexy girl when she starts undressing you.

And so, I was way too far gone to do anything more than whimper at her addition of thickly padded, flowered cloth training pants beneath the outfit's puffy skirt. "Come on, get that thing in there!" she teased - and I bit back a moan as those fingers of hers firmly forced my rigid cock down and into the padded panties she was tugging up between my legs. "There! Now if you have an accident or get too excited while you're near me, at least you won't make a naughty little puddle on the floor..."

Yup, you're reading that correctly. I, Matt Goodrich, actually let my sexy-ass roommate put me in a freaking dress and girly panties.

Then again, Abby seems to love it. And believe me - I can put up with a lot as long as it means I can be close to her.

***

Like, OMG. This is so much more fun than I ever imagined!

It's been two weeks now since that loser ended up pissing himself in front of me. Ten days since I first got him into that maid outfit and sissy training pants. Fuck, I almost laughed my ass off that night when I first tucked that pathetic little wiener of his into those panties. The sissy look really does suit him, doesn't it?

Of course I'm pushing him further. Because what's the point of being able to control a pathetic guy like him if you can't see how far you can take it?

Like just a few days ago. I made sure to blow up his phone when I knew he'd be in class. I'm no slut, of course - but I do at least know how to take hot selfies. I must've sent half a dozen throughout the day, each with its own little caption. "Damn, wish I had someone to help me out of this bra!" "Do these shorts make my ass look juicy?" "Bet you'd like to take a peek up there, wouldn't ya? Ya perv!"

That way, once Matt finally made it back, I was sure he'd be worked up and desperate to agree to just about anything I proposed. "Mattie boy," I sang out. "I've got something to ask you..." And so it was that, as soon as the blushing little nerd came in, I laid it all out for him. In exchange for getting to help me dress and undress every day - because honestly, who the fuck likes to dig through their closet themselves? - all he'd have to do is tuck two little additions under that maid outfit of his...

Yeah. You should have seen his face when I helped him strap those fake boobs on for the first time. Honestly, I don't think I've ever seen such a pathetic, horny, humiliated guy before in my life! Especially when I told him how cute he looked with them, and how I ought to get him some real ones someday...

But yeah - even that's not quite all. See, I'm fucking horny these days, too. Had a few flings earlier this year, but nothing really lasting, ya know? So might as well see what this loser can do while I've got him around. Didn't some famous dude say something once about necessity being the mother of invention?

Oh, not a chance that he'll get anywhere close to me with that loser dick of his - if you can call it that! No, I'd much rather have him needy and focused on pleasing me. Only problem is that right now I bet the little nerd is going off and jizzing in his shorts half a dozen times a day just thinking about how he wants to fuck me. Idiot's going to wear himself out just on his own time...

So I'm gonna see if I can't find a way to stop that.

Hey, don't look at me like I'm some monster! Of course I'm not forcing him to do any of this; it's not like I'm tying the guy up and making him my slave or anything. It'll still be his choice: get to spend some quality time with me on my conditions... or not. See? Completely up to him!

***

"Wha- what the hell is that?"

My voice is quavering with anxiety as I stare at the odd metallic device in Abby's hand. She just told me she had a special surprise for me this evening - and since she just had me help her strip down to her bra and panties, I'm sure it's gonna be good. But right now, I'm more than a little nervous. Might be another of her crazy ideas...

"Aww, don't you know, honey?" She's laughing at me again - but then again, she usually is. Strangely enough, though, I find my belly doing all kinds of flops and my dick getting hard every time she does. It's almost like some stupid part of me actually likes it when she's making fun of me... which is just flat-out weird. "It's just a cage, Mattie! A pretty new cage to keep that little dick of yours under control! It's been making it tough to get those panties of yours on, you know."

Oh, it has. "But- but won't it hurt-" I begin. But she's already tugging down my outfit's flowered training panties, pushing me firmly onto her bed. "Of course not, silly! At least, not if you hold still for me..." And then, I'm shuddering at the touch of cold steel on my stiff dick, wincing as I feel her soft fingers tugging, pulling...

Within seconds I hear a click, and Abby is grinning down at me. "Such a good, good maid!" she giggles. "I'm proud of you, Mattie - or should I say, Maddie? Now for your reward for being such a good sissy." And before my eyes, she slides languidly down onto the bed beside me, her fingers sliding provocatively over her beautiful ass. "I'm so fucking horny tonight, baby. I don't suppose you'd be a dear and... you know... help a girl out with that tongue of yours?"

Holy shit. She wants me to- to do what, exactly- "Aww, haven't you ever eaten anyone out before?" she giggles, seeing the questioning look on my face. "Don't worry - I'll walk you through it! Now, panties stay on tonight. Just bend down here and put that tongue to work... on my ass."

I'm quivering, repulsed and yet drawn on by the erotic sight before me. "Go on, Maddie," she urges. "Do it. It's your reward for being such a good maid for me, for putting on your cage..."

And as I squat down obediently, eyes slipping shut as I approach that glorious ass of hers, I shiver with nervousness. I'm so far gone: dressed in this frilly outfit, wearing thick pink panties and fake breasts, and now with what can only be described as a metal cage over my cock. But I'm closer than ever to my goal. Abby is letting me do- do this with her- Things I've never gotten to do with anyone else-

My wet dreams are finally coming true... though maybe not precisely as I expected. Still, there's no way I can possibly complain, is there? Even if I am dressed up like some freaky, sissy maid?

(To be continued!)