It was Christmas break and Harry was bored shitless. All of his friends had gone home for the holidays. Well that's a bit of an understatement. Truth is that all but six students in the entire school had gone home. There were two Ravenclaws, two Hufflepuffs, one Slytherin, and one Gryffendor. He of course was the one Gryffendor, he had no idea who either the Ravenclaws or the Hufflepuffs were, and the Slytherin was none other that Draco Malfoy. It's not that he honestly hated Draco, it's just that he would have preferred not to be in a situation where he was so completely bored that he would contemplate begging Draco to be his friend. But that's pretty much what Harry was set off to do after three days of staring into space.
Harry had checked his Marauders Map to see that Draco was down in the Slytherin commons room by himself. Harry wasn't sure if he could get into the Slytherin dorms, but he figured that it certainly couldn't hurt to try knocking. So there he stood, banging on the Slytherin Portrait.
"Malfoy! Open up will you!" Harry yelled repeatedly.
Eventually the portrait swung open just a crack, showing only Draco's face.
"What on Earth are you on about Potter?"
"And you wanted to come over and play? Is that it?"
"God Potter, you are so pathetic. What makes you think I'd want to hang out with you?"
"Well, I figured you might be bored too, since you're the only Slytherin staying. Aren't you bored?"
"Boredom, Potter, is self inflicted."
"What the fuck is that supposed to mean?"
"It means that I am fully entertained, thank you very much. And that I do not depend on others to stave away my boredom."
"What on Earth have you been doing then? 'Cause I haven't been able to think of anything to do."
"It's none of your business," Draco said with a faint blush rising across his cheeks.
"Aw, come on Malfoy, can't you just let me in, I'm sick of being along."
"Well, I on the other hand happen to value my alone time."
"But you can't possibly intend to sit by yourself in your room the whole time do you?"
"That was pretty much the extent of my plan, actually."
"Now that's pathetic. I don't care what you say, I'm coming in."
"NO!" Draco tried to pull the portrait shut, but it was too late, Harry had already managed to force his way into the Slytherin commons room.
At first Harry's eyes strayed over the room, but then he looked back at Draco.
"Holy fuck, Malfoy!" was all Harry could think to say at first.
Draco stood there with a scowl on his face, his hands on his hips, and a pretty blue dress over his rather nice figure.
"I told you, you can't come in here."
"Malfoy, you're wearing a dress!"
"I could get you into plenty of trouble for being in the Slytherin dorms."
"Malfoy, who gives a fuck, you're wearing a bloody dress!"
"I'm waiting for you to leave."
Harry was completely dumbstruck that Draco had not lost a single ounce of his commanding, patronizing presence, despite the fact that he was wearing a lovely little blue gingham dress, which Harry noticed, brought out a few flecks of blue in Draco's normally silver eyes.
"Malfoy, if you make me leave, or get me in trouble with Snape, I assure you everyone is going to know that you fancy wearing little girls dresses. I am very trustworthy, and I assure you no one would doubt my word over yours."
Draco's scowl intensified as he reached back and shut the portrait behind him before sulking over to sit in an armchair next to the fire. Harry himself, moved to sit across from him.
"So Malfoy," Harry began in a light conversational tome, "how long've you been wearing skirts?"
"None of your goddammed business."
"Okay then. Exactly whose dress is that then?"
"I dunno, I just went through the younger girls dorms until I found one that fit me."
Harry couldn't help but laugh and relish in Draco's discomfort that was truly only evident by that slight pink tint in his cheeks. Otherwise Draco was perfectly composed.
"So do you care to explain just why you were prancing about wearing a dress?"
"I was just trying to amuse myself. I was bored, so sue me."
The two boys sat a while in silence, staring each other down.
"So…" Harry began, "Are dresses comfortable?"
"I think so. I mean, don't you find trousers constrictive sometimes?"
"I honestly never thought about it."
"Well you really should try it sometime."
"Um… I think that's okay."
"Why? I think you'd like it! Come on!" Draco stood up and dragged Harry out of his seat, pulling him across the room.
"Where are you taking me?" Harry asked for the first time thinking that coming here may not have been a good idea.
"I saw a real cute little green dress that would look adorable on you!"
"Oh my god."
Before Harry knew what was happening to him, Draco had pulled his shirt off of him and was shoving a green dress over his head.
"I feel stupid," Harry complained as Draco buttoned him up from behind.
"Well of course you do. You're still wearing your trousers underneath. Go ahead and take them off."
"All right, then I will."
Harry was too shocked to do anything before Draco had unzipped his jeans and pulled them down to his ankles.
"Okay, Potter, step out of them."
Automatically Harry pulled his feet out of his jeans.
"Now doesn't that feel better?" Draco asked merrily as he tossed Harry's clothing aside.
Harry just stared in disbelief for a while before answering.
"You are absolutely demented!" Harry shouted.
"Hey, you're the one who begged to come over and play with me. If you want to go back to sitting in your dorm room alone, go ahead. Otherwise, we play my way."
"I can't believe I am wearing a dress."
"What's wrong with it? I think you look wicked!"
"It's just so…breezy down there. I mean, I feel so exposed."
"Yeah, well it wouldn't so much if you had pants on down there. You know I really never suspected you to be the type to go commando. I'm use to it, of course, I think it feels good."
"You're not wearing any pants either!?"
"No, but then neither are you, so what's the big deal?"
Harry didn't respond, but blushed deeply. His thoughts went from wondering why on Earth he thought it was a good idea to hang out with Malfoy in the first place, then he wondered if Malfoy was insane or perhaps drunk, then he thought that he really wished he were drunk at the moment. As Draco began playing with Harry's hair, parting it to one side and fastening it with a hair slide, Harry decided that he couldn't take it anymore.
"Malfoy, stop. This is getting too weird. What's wrong with you? Are you drunk?"
"You're the one who was determined to know what I did in my free time, so what are you complaining about?"
"Look, I just had no idea you would go crazy and start dressing me in girls clothes."
"Hey, we all have our own ways of relieving stress, this is mine."
"Can't you just go and get drunk like everyone else?"
"I guess we can do that too, come on." Draco once again grabbed hold of Harry's arm and dragged him off.
"That's not really what I meant…" Harry complained ineffectually. Before he knew it, he was back in the commons room and Draco was shoving a bottle of alcohol in his hand.
"Spiked Pumpkin Juice?" Harry asked, reading the label.
"Yeah, it's good, go ahead, try it." Draco lifted his own bottle to his lips and took a deep swig.
Harry hesitantly took a sip, but finding it to be quite good, began downing it quickly. If he was going to be stuck wearing a dress, he might as well be drunk. It didn't take too long for both of them to become increasingly tipsy as Draco kept pulling out more and more bottles. Soon they both found themselves very easy with each others company, and Harry eventually came to think it the most natural thing in the world for he and Draco to both be wearing dresses.
"Ya know, Draccy-Baby," Harry said, now completely pissed, "you are the most beautiful girl I've ever seen."
"That's Draco-Baby to you, Potty-Baby, and I'm not a girl." Draco was equally drunk as Harry.
"Harry-Baby to you then. And of course you're a girl. You're too pretty to be a boy." Harry was now leaning over Draco and playing with his hair.
"But that would mean that you're a girl too, 'cause you're definitely too pretty to be a boy."
"Hmmmm…tha's funny, 'cause I…I really thought I was a boy!" Harry looked thoroughly confused now.
"I don't think it matters, though. Does it?"
"I guess it doesn't!" Harry smiled, apparently relieved,
"Say, you know what we need? Music."
Draco got up and went to the other side of the commons room where he began fumbling with a strange magical box which soon began playing music.
"Come on Harry-Baby, le's dance."
Draco pulled Harry to his feet and wrapped Harry's arms around his shoulders, placing his own arms around Harry's waist. Slowly they began rocking back and forth, not necessarily in time with the music. Harry leaned his head close to Draco's, noticing that he smelled of roses.
"You even smell like a girl, Draco! Are you sure you're not a girl?"
"You know what I think…" Draco paused as if he were about to divulge one on the great secrets of the world. "It depends on what you've got under you're skirt!"
"Under your skirt?" Harry repeated, unsure.
In order to test Draco's theory, Harry moved his hands off of Draco's shoulders and down his back towards his skirt. He began pulling it up to his waist, exposing Draco's naked backside.
"All I see is you're ass," Harry said, peering over Draco's shoulder.
"I have an ass?"
"Yeah, it's a nice ass, too." Harry moved one hand on each cheek and grabbed them firmly.
"Do you think you have an ass too?" Draco asked as he began pulling up Harry's skirt. "OH! You have the most beautiful ass I've ever seen!" Draco said with misty eyed wonder.
Draco leaned around Harry's body to get an up close and personal look at Harry's beautiful ass, lightly trailing his fingers down the middle, full of awe.
"You know, Harry, I never knew you had an ass. Was this always there?"
"Um… I think so. I never thought about it." Harry tried ineffectually to look at his own ass. "Is it really that beautiful?"
"It is! I mean just look at the way it…OOHHH!" Draco just then found the entrance of Harry's ass and was rather excited to learn that he could slip a finger inside. "Harry, tha's so cool! Did you see what I jus' did? I've never seen anything like it! Does my ass do tha' too?"
"I dunno, lemme see…Holy Crap it does!" Harry shoved his index finger deep into Draco's ass and started wiggling it around.
"Oh shit Harry! That felt good!"
"Um…Draco, I'm not sure, but I think you're…hard. Does that make any sense?"
"I mean, like you were once soft against my front, but now you're…hard."
"Oh, you know, I think I noticed the same thing about you, but I didn't want to mention it. What do you think it is?"
Both boys broke their embrace and mutual ass exploration and proceeded to lift the front of each other's skirt.
"Hey Draco, you are a boy, look!"
"Yeah, you too!"
The boys stared a while at each other's impressive erections.
"So, uh, Draco, if we're both boys, then why are we wearing dressed?"
"Well…maybe we're gay!"
"Ooohh, that makes sense, then. But if were both gay, are you sure it makes sense for us both to be wearing skirts? I mean who goes where?"
"Well, I mean, the one wearing the skirt is supposed to be on the bottom…I think…but we're both wearing skirts."
"Oh, tha's a tricky one tha' is. I don' really know. Perhaps, one of us should take off our skirt."
"Oh yeah, tha's a brilliant idea! Shall I take off my skirt then?"
"Um…okay. I think tha' sounds right."
With some assistance from Draco, Harry's pretty green dress eventually came off.
"Oh!" Draco exclaimed, trying not to cry. "You're the mos' beautiful thing I've ever seen!"
"No, Draco, I'm not supposed ta be beautiful, you are. You're still wearing the dress, remember?"
"Am I beautiful then?"
"Draco, you are the most beautiful girl, um, I mean boy in the whole world!"
Harry moved closer to Draco and placed a big kiss on his lips. For a long time the two of them kissed wildly and passionately. It was Draco who finally broke the kiss by speaking.
"Fuck me Harry," he whispered breathlessly. "Please."
"Okay. How, though?"
"Um… I think…" long pause. "You put that," he pointed to Harry's hard cock, "there, where your finger was," he pointed to his own ass.
"Tha's brilliant!" Harry said as he threw Draco down on the couch, landing on top of him.