The Day My Sister Tricked Me Ch. 01-02

PART ONE

Saturday morning. No plans for the day. Taking a nice warm shower. Super relaxed. Super happy too; my friend Jack and I are planning on going to a gig Monday night. The thing is, I'm only 18 and it's a 21's show, but since Jack's uncle owns the bar, he was able to pull a few strings. He's willing to let it slide just this once. But strictly no drinking, which is fine by me. I'm not going for the alcohol anyway, I'm going for the music and more importantly, the girls. It was an ordeal convincing my parents though, believe me. I had to beg, especially since it will be on a school night. It kinda sucks that I even had to plead - I'm an adult for God's sake! But whatever, I'm just grateful I've been on their good side for the last couple of weeks, so they had no reason to say no. Which is good, since it'll be another 3 years before I get this opportunity again. And it's not like I can fuck this up now, my parents have already said yes before they went off for the weekend. They'll be back Monday evening, and I'll be heading to the bar a few hours later - I wouldn't have time to get on their bad side if I wanted!

I turn off the shower and pull back the curtain, sighing with satisfaction. I absentmindedly reach for my towel, still thinking of Monday night. My hands don't grab on to anything. What? I look down. Surely enough, no towel. "I could have sworn I threw it there" I mutter, before turning to have a look around the bathroom. Then I stop. There's a small sheet of paper, right where I was sure I left my towel. I can see there's something written on it. I grab it with intrigue, and read what it says:

Hey bro,

Your sister Sarah here. Just letting you know, I learned about your dirty habit. Good to know you smoke behind the bike racks after school. You know how unhealthy that is? Is this every day?

Look, I'm gonna ditch the false concern and just gonna cut to it - I know how much you want to go to that gig. So, I suggest you start listening to what I have to say, or Mom and Dad find out you smoke. Makes sense? Good. Oh, and by the way, it won't be a case of my word against yours - Jessica Snapchatted me videos of you and the guys. I don't think your secret spot is as secret as you think :)

Anyway, you're probably wondering "where's my towel?". Well, I was thinking... I'd be a pretty damn boring Saturday if you were able to happily stroll to your bedroom and throw on your own clothes. Your sense of fashion was never great anyway. So, there's a new outfit in the laundry basket next to the sink. I'll say no more about it, other than this:

You will where it, or no gig Monday.

Have fun princess! :) xxx

What. The. Fuck. I am screwed if my parents find out I smoke. I'd never hear the end of it. They'd never let me go places or do me any favors again. They won't care what excuses I throw at them, and it won't matter than I'm an adult and have every right to smoke if I want. Their house their rules, as they always say. And I knew some girls hung out near the bike racks but I didn't know they were fucking spies, God damn! How the hell was I supposed to know they'd Snapchat videos of me smoking? And now I gotta play dress up because of it? This is bad. And why the hell did she call me princess!?

But wait a minute, my sister might know I smoke, but what if she's bluffing about the vids? Nah, I can't risk that. Plus, it's not like she needs solid evidence, she could just tell my parents when they return, and they'd probably cancel all my plans until they find out the truth. And as I said, I'll have to wait until I'm 21 before I get another chance to set foot in a bar. My mind is racing... I hate that my sister has this dirt on me. What am I gonna do? I glance over at the laundry basket. I guess I should check it out. Not saying I'm giving into her! But there's no harm in seeing what's inside...

I open up the basket, to see a pile of clothing. The top item is something I instantly recognize as a bra. What the hell? I pull it out and hold it up on front of me. It's black and unfortunately, lacy. Not lingerie levels, but lacier than anything I've ever worn! I can tell it's Sarah's, as the straps are very close to one another to accommodate her petite frame, while the cups are quite large. She's always had that ideal physique... as my friends often remind me. It looks like the straps will be tight on me, and the cups are just gonna get in the way - wait a minute, am I actually considering this? This is insane, but realistically I don't have much choice. If I ignore her commands, she'll definitely rat me out, and that means no gig Monday night, plus a whole lot more trouble. But if I do exactly as I'm told, she won't tell my parents that I smoke. She has blackmailed me before (though not to this level, by a long shot) and she has always kept her word. She knows that if she broke a promise her word would mean nothing and she'd never be able to manipulate me again. That's not something she wants, so oddly enough she can be trusted. And this is my one shot at going out Monday, so the least I can do is check out the rest of the outfit, and hope there's no more goddamn lacy stuff.

The next item looks like a shirt, but it's much too small, surely. I unfold it and hold it up on front of myself. It's a top alright, it's just cut super short - a crop top. It's pastel pink, with a big white heart and the word "selfie" written on it. So dumb. But also so damn girly, and therefore so damn embarrassing. I begin to wonder why she left a bra, if she just wants me to cover it up with a top anyway. I guess the under layer is for discomfort, and the outer layer is for embarrassment. What a vengeful bitch.

I move on. Another item of the same pastel pink. For fuck's sake. It's underwear, and Jesus Christ are they small. Not lacy though, thank God. Very simple, in a sort of bikini bottom shape. They look like they'd be tight even for a girl. I look down between my legs and wonder how the hell I'm gonna pull that off. This confirms my theory, the under layer is definitely for discomfort! It also doesn't help that "Princess" is written across the front in white. That explains the note though. Fucking Hilarious. God damn, I really need to just power through this...

It shouldn't be all bad anyway. I start thinking of a plan to counter hers. She never said how long I'd have to wear the outfit for. I could literally throw it on, open the bathroom door and sprint to my bedroom. She'll probably be standing in the hall with a big smile on her face, maybe even trying to snap a picture. But I don't care, I can barge right past her - I'd like to see her try and stop me! Once I make it to my room, I get changed. Easy.

I look over the note again to confirm that she only said I have to wear it, and didn't specify a length of time. Nice. This could actually work. And she can't be mad at me, all I did was outsmart her. Once I get to the safety of my room, I'll be happy. Then, I just have to keep my wits about me until Monday to avoid anymore stunts like these. Mom and Dad will be back, I'll go to the gig, and that will be the end of this crap. Hopefully.

I turn my attention to the clothes I have yet to examine. A black ball of material has me confused, until I unfurl it and it separates into two. Two bunched up black balls - a pair of nylon stockings. I stretch them out. They look like thigh-highs. Not cool. And the next item isn't even clothes. It's a thin black choker. That's just pushing it. I used to find those kinda cute on girls, but this experience will surely ruin that for me. Finally at the bottom of the basket, there's a pair of open-toe heels, pastel pink yet again. They must be 6 inches. I think they're my mom's. It'll be hard to sprint in them, that's for sure. Damn, Sarah put a lot of work into this.

But I'm sticking to my plan. My sister is probably patiently waiting beyond the door for the glorious moment, but little does she know I won't be wearing this crap for long. I reckon she'll get about 10 seconds of entertainment before I'm in my room again. Feeling a lot more relieved about the ordeal now, I grab the clothes together and see what I'll put on first. It's only then that something terrible dawns on me. How the fuck didn't I realize this before - there's no fucking pants!

*****

Aaaaaand panic ensues once more. I find myself sitting naked on the side of the bath, beginning to tear at my hair which is still sopping wet. I could deal with enduring the discomfort of the pink little prison that is her underwear, especially since I planned on removing it ASAP. I had come to terms with that, but... not covering it up? Walking out in something that tight? Not to mention, something that feminine? And shit, what about the back? I grab the underwear again and turn them around. They look like they'd cover less than half my butt cheeks. What the hell am I gonna do?

Fine, let's ignore the underwear issue for the time being and continue with the plan. The other items don't seem half as bad now. I can't believe I am really doing this, but it truly is the best option. I decide to take the plunge, and grab the pair of stockings. They're not that bad anyway, or so I try to convince myself. I attempt to stretch one out and fit my leg into it, but it's a struggle. I quickly realize it's easier to bunch it up and put it over my foot, then pull. It covers my leg with ease, coming right up my thighs. They are tight, but soft. Really soft actually. Honestly, things could be worse. Although, I feel weird wearing nothing but long black socks, (especially because, looking down at my legs, it's impossible to tell they are not a women's...) so I quickly grab the top to put it on, before remembering the bra comes first.

I hold up the bra. For a second I forget who the owner is, and become a little distracted by the slight sexiness of it. Fuck, I'd love to be holding literally anyone else's bra other than hers. But I can't deny it is an attractive piece of clothing. I tear my eyes away and awkwardly put it on. I am surprised by how easy it was to slip on, and it was not as uncomfortable as I would have expected. "Hey, maybe I should dress up like a girl more often?" I sarcastically tell myself. Yeah right. At least I am capable of making jokes in a situation like this. I can't bare to look at myself once I have it on, so I quickly throw the crop top on over it. It successfully covers the bra, but not much else.

A minute or so later and I am standing in the bathroom in thigh-highs, a bra, a crop top, heels and a choker. It is the strangest thing ever, because with only a few items of clothing, I suddenly look like a girl from the majority of angles. I never had much body hair, and I have always been quite slim. They only thing that disrupts the feminine facade is the dick dangling between my legs. Wow, Jack would get some kick out of this if he saw me. And no doubt Sarah would too. But I keep reminding myself that it will last at most 10 seconds. My bedroom is so close to the bathroom. It will all be over before I know it, and I would have followed Sarah's orders precisely, so there'd be no reason for her to rat me out. I know how she is, if I outsmart her she'll respectfully take the loss and move on to another evil trick. Or so I hope. Regardless, following her rules is definitely my best bet. But, there's still one problem with that - the last thing I have yet to put on, the underwear.

I'm holding them up on front of me again. I am almost completely dry now, the clothes absorbing a lot of the water and becoming a bit wet. I keep looking from the underwear to down between my legs, trying to figure out how the hell this will work. I'm not exactly the biggest down there, but these are not exactly the biggest underwear either. Plus they're not designed to accommodate for much room in that area. How am I gonna do this exactly? Well, only one way to find out, I guess.

I sit back down on the edge of the bath, and reluctantly raise my right leg. I step a pink heel into a hole of the panties, and then do the other leg. OK, let's man the fuck up and just pull these things up! I stand, grab the tiny pink excuse of clothing, and yank them up like they were my own underwear. I am not even near my crotch when I feel them tighten and I have to bring my legs a little closer together. I pull them further up, more slowly this time. They are just under my crotch now, and unfortunately enough, I am slightly erect. Which of course has nothing to do with my current situation! It must have been a random hard-on. It happens. But it doesn't help my situation, because now I am bigger than usual and these panties look smaller than ever.

I stretch them up and over my now moderately-sized cock in an attempt to cover it. I instantly feel constriction from the back - these things are already riding up my butt - and by the time they are completely on, they barely cover my manhood. I mean, this looks laughable. My bulge pushes and stretches the panties down way further than they were meant to go. It's already so tight and I can't even pull them up fully - my pubes and the base of my cock are completely visible. How and why is my sister so small, and yet she's a year older than me?!

Besides looking ridiculous, they are also pretty painful to keep on. And, twisting around to look at the back, I am shocked to see the panties have been so stretched to their limit from the front that they don't cover my ass even remotely. Anything that could cover my ass is bunched up... between my cheeks. I pinch a corner of the panties - the part that should cover one's left butt cheek - and try to pull it down so it can do its job. But there's no leeway. It's even tighter than I thought, and the tension causes it to slip from my hand and snap forcefully back into position, whipping my ass with a sharp *SMACK*

I felt my face go red and out of nowhere I found my heart beat increase momentarily. I stood there for a few seconds, holding my breath. Before I knew it I was calm again. But that rush I felt, what was that about? I am probably nervous that something will go wrong and someone will end up seeing my like this, that's all. But that's not gonna happen! I am ready to step out of this bathroom and run to safety.

This will work. Well, that's what I thought until I looked down again. I guess that little rush I got may have influenced a little blood flow. Or a lot. I was fully erect now, and the panties looked like they could bloody burst. Half my shaft was visible. It didn't even look like I was wearing underwear anymore, it was more like something designed to cover the head of my cock and not much more. And since it had grown bigger, it tugged and tightened the back even more. The panties resembled a thong from the back they were so far up my ass. And don't get me started on the pain. Screw this.

I pull the underwear down until they hang around my knees. I stand there for a moment and appreciate the comfort of being free. This isn't going to work. Letting my dick show when my sister could be out there? No way. Plus the discomfort, plus the zero coverage on the back? Nope, I gotta rethink this.

I think I'm going to have to wait until I am soft again. But of course now that it's vital that I don't think any sexual thoughts, what do you think I suddenly can't get off my mind? It's like tasking yourself with trying not to think of a pink elephant. It becomes the only thing you can think off. Suddenly all sorts of sexual thoughts flood my mind, and I remain as hard as ever. And all I can see is lacy, skimpy clothing, and I hate to admit it but it's just adding fuel to the fire. I will calm down eventually though, right? Well, it doesn't seem like it will be any time soon. Maybe... Maybe I have to get rid of my erection the other way...?

No. There's no need for that, c'mon! It's weird enough I am dressed like a girl, do I have to make it weirder by jerking off while dressed like this? I was ready to run just a moment ago, now I want to touch myself? But realistically, it would solve the problem. I'd get soft and actually be able to conceal my bulge, and it will give the panties some slack to cover my ass.

I look down at my crotch. My cock is actually throbbing. And just beyond my cock and out of my direct focus, is a pair of slim legs in heels and thigh-highs. Shit, that's weird but it is so easy to imagine a women's body right now. I slowly reach down and grab my cock. I start tugging on the shaft, moving slowly up and down. I close my eyes and completely forget about my situation. Wow, I guess jacking off really does relieve stress. I laugh at the thought and continue stroking, building up speed as my thoughts jump from slim legs in heels to sexy lingerie and fit female bodies.

I fall deeper into my fantasy and imagine getting intimate with a beautiful babe in a lacy black bra. I'm kissing her passionately and grabbing her breasts. It feels so real. I reach down and begin to toy with her underwear. I turn her around in an authoritative manner, and bend her over slightly. She loves it. I grab her panties and pull them to the side. They're pink and quite tight. I run my hand under them, my palm placed firmly on her ass, and grip. My other hand is still firmly holding her breast. I lift my hand from her ass, then land it back down with a loud slap.

Eyes open, back in the bathroom. I'm awkwardly bent over, legs slightly spread. Did I hear that slap for real? I look around me, and of course I'm still alone. I then study myself. I can't believe it... one hand is firmly gripping the cup of my sister's bra, while the other rests on my right ass cheek. Neither hand is on my cock anymore, but it is nonetheless still hard as hell and incredibly close to cumming. I lift my hand from my ass and unsurprisingly, there is a huge red mark in the shape of my hand.

What the hell am I doing? I suddenly come to my senses a little, realizing I am just making things worse for myself. The longer I screw around in here, the longer my sister has to prepare outside. I can just picture her now, sitting silently in a director's chair, with a whole camera crew crammed into the hallway, waiting to capture her feminized brother in high definition...

Jokes aside, I need to get a move on. I haven't heard a word from beyond the bathroom. I wonder if she got impatient and left? I wish. But she put too much effort into this, so I know she's there. I am still unsure of whether she'd be cruel enough to try to capture all this on her phone. But if she is, it's all the more reason to sprint to my bedroom, and all the more reason to cover my body as much as possible.

I stare back down at my throbbing cock. A small amount of pre-cum is dripping from the tip. God damn, I am too stressed out to even finish jacking off. And I'm honestly a little too weirded out to finish off anyway. I slapped myself. Hard. That's not something I've ever done before. The girl I pictured... I can't ignore that she was wearing the exact underwear I was. "Great" I think sarcastically, "I make such a hot girl I can even jerk it to myself. Maybe I should be a cross-dresser!". And although that was a complete joke, it actually solved my main problem.

I'm a guy, and I'm wearing panties. A lot of guys do that. Cross-dressers, drag queens, etc. And what do they do to hide any evidence they're a guy? They tuck.

I would simply have to push my dick down and back, between my legs, then pull the panties up. It will look flat on front (better than a bulging dick ready to escape) and it wouldn't stretch the front, so the panties could be pulled down more over my ass! I was back on my game now, continuing to counteract my sister's plans! Granted she has my dressed like a stripper, but I'm making the most of it! At least my cock won't be visible.

Tucking is more easily said than done though, especially while still pretty erect. It kinda hurts to bend my erection way back like that, but it honestly sat pretty nicely between my legs. I held my legs together to keep it in place, and it kinda looked like I was trying to hold my pee. My balls were a little uncomfortable, but it was better than being squeezed to death by panties. Speaking of, I pulled the little death-trap up to my groin again to see would they fit better this time, and they fit like a glove! I stared in disbelief for a few seconds, wondering how they could be the same panties that could barely stay on me a while ago. It looked super flat from the front; it was like my dick wasn't there. And it wasn't even that tight of a fit, even with a hard-on. I moved my hips back and forth and moved my legs a little, but the panties kept my cock comfortably in place, and well hidden all the while. Ha! Check mate, Sarah!