Done for the dn_kink meme over at LJ, prompt was "Mello/girl!Matt, Extremely awkward, uncomfortable sex. First time while at Wammy's, they're too busy working out where things should go and what to do to enjoy it that much because, damn it, books have always been so helpful before. Aka Mello attempting to follow a books description to the T about sex."

I took some liberties with the "book" part, and this is my first attempt at genderswap. It's been soo long since I've attempted smut, even awkward smut XD, be kind.

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Disclaimer: I don't own or make money off anything featured in this story. If only.

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Mello always did his homework.
This situation was no different.

He ran through his researched facts in his head as he placed the recommended items on the table beside his bed, and minimized the search window on his laptop while lowering the screen.
Everything was ready. He would NOT fail at this.

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As he waited he stared at the wall, still running through what he had learned. He almost wished he'd just let things happen spontaneously, but according to his sources, discussing the matter beforehand was Step 1, and he'd be damned if he wasn't going to follow the instructions to the letter. He was going to do this right.

It was 1am before he was snapped out of his reverie by the handle of his door turning. Matt's tousled auburn head poked inside before she entered fully and locked the door behind her. "Hey, I didn't see you at dinner. I thought you might have changed your mind." At the sound of his voice Matt came and flopped on the end of his bed in a graceless heap as she usually did. "Nah, wasn't hungry. I had other things to do, y'no? I'm here now though." Mello could only assume this meant she'd been absorbed in one of her games, and lost track of the time.

"Well I've, err, got everything ready," he said, gesturing at the bedside table. "If you still want to, that is." Matt's eyes widened at the assortment of colorful wrappers there. She choked back a laugh. "Uh, Mells, why do you need seven different kinds of condoms?" Mello frowned at her amusement. "Because that's what you're supposed to have. I know. I looked it up." Matt cocked an eyebrow. "Well if you're sure…" she trailed off. Crawling closer she leaned towards him.

Mello hesitated a moment before artlessly mashing their lips together. Matt's teeth collided with his lip, and he felt her wince. He would have liked to slow things down to their usual languid kissing, but sex was meant to be about passion, so he prodded her mouth open with his tongue. They persevered like that for a few minutes, until Matt broke away, breathless, but not panting like usual. Her hands twisted in her oversized striped shirt. "So, perhaps I should… ah…" she looked pointedly down at the shirt. Mello felt a shiver of excitement. Time to put his research into practice.

"Why don't you lie down?" Matt stared at him for a moment, shrugged her narrow shoulders and flopped backwards onto his pillow. Mello looked at her, sprawled out on his bed, and felt himself begin to get hard. He pulled her shirt off her and she shivered. Is she aroused already?, he wondered. He paused to take in the smooth whiteness of her stomach, and the shadows of her hip bones. He wanted to trail his hands down them, but snapped himself out of it. He needed to focus. That was not part of what he'd read about.

Mello could feel his hard on straining his pants now, and he hurried to undo the fly on Matt's loose jeans. She shivered more as he stripped them off her surprisingly shapely legs, and was about to take that as a sign of encouragement when… "Um, Mells, it's kinda cold in here. Do you have a heater or something?" Mello flushed, pride slightly stung at being wrong. Attempting to rally his flagging courage, he pulled his own shirt off and delivered a line he'd heard one of the older boys at the orphanage use before. "I know how to get you warm, baby."

Matt just rolled her eyes at the cheesy line, and allowed Mello to unsnap her bra and pull the cloth from her chest. She shifted self consciously as her best friend stared hungrily at her small breasts.

Mello noticed the sudden change. "You still want to keep going?" His voice had a new husky edge to it as he asked the question, and it pulled at something in Matt. She just nodded underneath him. The boy's hard on was starting to become uncomfortable, but from what he'd read he knew it was important to prepare Matt first, so he slid off her panties and hesitated with his hand between her legs. Her blush was burning as red as her hair now, but she hadn't told him to stop, so he experimentally slid a finger between her folds. Her hips shifted slightly, not closer but not away. Taking that as encouragement he slid a finger up into her. She should be wetter than this, shouldn't she? But she made no protests as he slid another finger up into her and began to draw them in and out.

His breathing was ragged and his erection was throbbing painfully now, and oh god he wanted to run his hands all over her, but he kept with his prescribed method, now searching for where the anatomy books had said her clitoris should be with his thumb.

I wonder what it would be like to taste her. He shook the thought out of his head. Never had he seen anything about that anywhere. No way did he want to do something weird that would freak her out. Thin arms wound around his neck. "Just do it, Mello." Matt said quietly, and Mello was too far gone already to argue.

Quickly shedding his pants and boxers, he rolled on a condom (his source had told him to practice, and practised he had) and positioned himself between her thighs. Kissing her quickly, he began to slowly push in to her still so dry entrance, and he felt Matt's arms tighten almost painfully around him. Around halfway in Matt started to shift her hips under him and he began to draw back out and thrust in again when a loud 'snap' was heard. Mello froze, wide eyed, and looked down at Matt. "W-was that, ahhh, you?" he stammered awkwardly, as Matt began to push at his shoulder. "No, you idiot, that was the fucking condom, get off, this stings."

Hurriedly, Mello withdrew, and Matt hissed in pain and rolled on to her side. Positively shaking with embarrassment Mello sat on the edge of the bed. A nasty voice in his head whispered 'Step 5 failed.'

"Screw this." He muttered, and turned to Matt, who was lying on her back staring at the ceiling now. Sliding on to his knees, he kissed above her navel and ran his hands down her bare sides. He dipped his tongue in the indentation and continued to trail kisses lower as a breathy voice above him stammered "What are y-you doing Mells?" Nudging her legs apart with his knees and sliding lower, he had a moment of trepidation about how she might react, but ignored it. Gently, he dragged his tongue from her slit up to the clitoris that he'd had so much trouble finding before.

Matt's reaction was the complete opposite of what he might have expected. He felt her back arch underneath his still wandering hands, and a low delicious moan came from her lips as fingers wound through his golden hair. Mello repeated the action, and then on a stroke of courage, pressed his tongue in to her entrance. Matt's fingers tightened in his hair as she moaned his name, and emboldened even further, Mello began to rhythmically thrust his tongue into her now hot and throbbing passage.

Matt's cries were becoming more desperate, and she pulled Mello up for a kiss, tasting her own saltiness in his mouth. They were both breathing heavily as Matt asked "Do you want to try again?" Mello rested his face in the crook of her neck, panting. "You sure?" If she backed out again this time, man was he going to have a serious case of blue balls. Not that he'd ever actually tell her that. His train of thought was completely de-railed as Matt ground her hips up against his hard on, causing him to give a shuddery gasp. He felt the crinkly foil of a condom wrapper being pressed into his hand. "I'm sure." Finally his source had been right about something. All those condoms were handy. He slipped it on and felt the redhead underneath him grind up against him once more. Face still buried in her neck, he held her hips as he pushed into her for the second time that night.

Matt let out her loudest cry yet, half pleasure and half pain, and Mello nearly came right there from the feeling of that tight throbbing heat enveloping him for the first time. He held still for a moment, trying to control himself, but Matt impatiently began to rock her hips up against his, and then something in Mello snapped, and he pushed himself into her as deep and fast as he could, and Matt was yelling, but it was all pleasure now, and then he sunk his teeth into her neck and oh god she was coming, squeezing around him, and Mello came harder than he ever had before, back arching and calling out her name like he sometimes did when it was just him and his own perverted thoughts of her, and then he collapsed onto her panting chest, and his last thoughts before falling solidly asleep were "I win."

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Mello was vaguely aware of two things: one was the thin ankle that was digging into his neck, and the other was the sound of the Windows start-up music. Neither of these things were uncommon with Matt around, but the two defining characteristics of this situation that were causing Mello to struggle awake were that it was Matt's naked lap he was sleeping on, and that he'd only minimized the window from before…

He heard an indignant gasp from somewhere above him, and knew it was too late. The next thing he felt was a smarting smack across the back of his head, and a ringing shriek that could be loosely translated into "YOU LOOKED UP HOW TO HAVE SEX ON FUCKING EHOW!?!"

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*sweatdrop* I'm still terrified this is awful. Yes, there actually is a "How to" for this on eHow: http://www ehow com/how_4788237_sexual-intercourse-first-time html (just fill in the spaces with . ) Gotta love the internet.

Feel free to point out any spelling mistakes/grammatical errors, and costructive critisism is welcome, as always.