Get Caged

It's been two months. The holidays came and went and nothing out of the ordinary happened.

Really, it should have been a nice break. On paper, it was perfect. Nothing but free time, presents, and a lot of great food.

But something felt wrong. Even though life was great, it didn't satisfy you like it did before.

You're playing video games when you get a text from Megan informing you that she's coming over, and not to be doing anything weird or gross when she gets there. She opens the door without knocking.

"Sissy," she says, acknowledging you as she kicks her heels off and sits on your bed. You're on the floor leaning back against the foot of the bed playing games on your Xbox. "Where's your mom? I didn't see her car."

"Work, I think. She's been back at meetings like every day now that her PTO is used up." You shrug, glancing back over your shoulder at your friend.

Megan is wearing a red sweater and tight black pencil skirt with silky black tights. You blush, seeing a little thigh peek out in the slightly sheer space between stocking and skirt. Her legs look so long and smooth.

Megan smirks when she catches you looking. "Like what you see, sissy boy? Or wish you were wearing it?"

Your blush grows hotter and you know your ears must be bright red. "I- I was just wondering what you were all dressed up for. You normally just wear leggings and a T shirt when you come over."

"Hmm, true. I don't care how you see me, sissy. But I had a date this morning. You know, with a real man." She giggles, sliding over on the bed to sit with her legs dangling over the edge on either side of you. She starts playing with your hair, petting it like she's thinking about giving you braids. "And I wanted to look cute for him."

"How'd that go?" you grumble, unsure what else to say. It wasn't the first time she'd talked about her romantic ventures with you. You knew you had no chance with her, but it still made you self-conscious hearing about how suave and cool and manly her dates were. It was like she was comparing you to them and you always lost.

She shrugs. "It was okay. He was hot - a total gym-body. I was totally looking forward to the hookup later. But he was checking out other girls while he grabbed my ass. Like - what the hell? I don't mind being pawed at a little on the first date, but at least keep your eyes on my goods while you do it. At least pretend you're only undressing me with your eyes while you cop a feel."

"Er, sorry to hear that..." you squirm as she twirls some of your hair around her finger over and over. You feel an uncomfortable bulge grow in your pants thinking about someone feeling Megan up. You know you shouldn't but you can't help it. Your body reacts on its own.

"Yeah..." Megan sighs dramatically and leans on the top of your head. "I just wish I had like, a hot guy friend to fuck and feel me up from time to time, you know? Like is it so hard to ask for someone to dick me down when I get hot and bothered?"

You stiffen - in more ways than one. "I- um... no. Not too much to ask for. I mean, uh... You know, I'm sure there's someone out there like that for you. You're like the hottest girl in school, so anyone would be lucky to have you."

Megan cracks a little grin and strokes your hair. "Hehe, good boy, Aiken. You certainly know how to flatter a girl."

Fuck! Your body tingles all over like you just got an electric shock. You squirm even more and swallow hard. Why was that phrase affecting you so much? You weren't into that kind of thing. It just caught you off guard. But...

"Ew! Are you getting a boner, sissy boy?" Megan sneers and leans back, taking her hands out of your hair.

"N-no! No way! It's not like that, I just..." You stammer and lean over, curling your knees up and together and laying your arm across your lap to hide the embarrassing bulge.

Megan scoffs and gets off your bed. "And here I thought you were finally learning how to treat a girl right."

"S-sorry, Miss..." you stammer. You didn't like that you got caught with a boner, but you felt a little guilty that it had come from the mental image of her getting felt up. At least, most of it had.

"Tch, sorry won't cut it, sissy. You know the rules - no perving on me or my friends. In exchange, I help you become a better more-girly sissy. Jeez, you've been doing so well lately I had started to forget you were a little perv. Now stand."

You groan but do as you're told. You wouldn't dare talk back to her. Not when she has folders of embarrassing materials of you that she could share at any time. Not that she ever would, but their existence alone rendered you pretty much helpless.

She starts digging through your closet.

"Um... may I ask what you're looking for, Miss?" you sheepishly inquire.

Your classmate glances back at you. "Oh, just something to change into. We're going to trade clothes, you see. And I want something clean that hasn't touched gross sissy skin."

"Ch-change clothes? You mean..."

"You'll be putting on the outfit I'm wearing right now. The one I wore on my date - as punishment for being a little pervert. We'll see how hard you get when you're in my shoes - literally."

"B-but, we can't!" you gasp out. "What if we get caught?" It had been weeks since you'd crossdressed. With mom back and no assistance from Jeff, you didn't have many options besides begging Megan. And you had been to scared to do that after the last time.

She shrugs, tossing out some old shorts of yours. "You said your mom was gone today, right? Daddy too? So we're alone. No one to catch us. Besides - you want to wear girly clothes again. I can tell."

"Wh- no I don't! I mean... maybe just a little. But that's because I got so used to it. I don't need a whole sexy outfit!"

She laughs derisively. "Oh- you think it's sexy now, sissy? Well how abou-"

A small box thumps out of the closet and onto the floor by Megan's feet. She bends over and picks it up. "What's this?"

You scrunch your brow together. What was it? You couldn't remember hiding anything back there. Unless...

You gasp and lunge towards the box, frantically trying to snatch it out of her hands.

But it's too late. Megan opens the box and grins ear-to-ear at her discovery. It's the cock cage you got from the mall. The one 'Mistress' Jenny had slipped into your bags.

"Oh. My. God. Aiken, is this what I think it is?" She can't keep the giggles out of her voice.

"I-it's not what you think, I-"

She holds up a hand. "Actually, I don't care. This is perfect! Strip, sissy. Now."

"Wait, Miss, please..." you start, but she quickly cuts you off. You can see her pull out a key and smile even wider, licking her lips like a predator eyeing its next kill.

"Uh-uh-uh, sissy," she tuts, "Do as your Miss commands. I don't want to hear any begging from you except 'Please cage my little cock, Miss.' Got it?"

You nod and shiver, closing your eyes and wishing you didn't have such terrible luck. Wishing you could at least explain why you have a cock cage in your closet. "Yes Miss..."

You pull your shirt off and toss it aside, slipping your shorts off next.

"P-please... Please cage my little cock, Miss..." you whimper.

Megan beams and steps closer to you. She puts one hand on the back of your head and leans in, whispering in your ear.

"Good boy, Aiken."

And with her free hand, she yanks your boxers down.