Set during The One with Ross's Wedding Part 2 (4.24) and The One After Ross Says Rachel (5.01), with references to The One with Phoebe's Uterus (4.11), The One with The Sonogram at the End (1.02), and The One With the Truth About London (7.16).

One

Chandler didn't usually have sex when he was drunk. Well, he didn't usually have sex at all, but on the occasions that he did, he was painfully sober and painfully awkward.

And of course, he still was. Both. But the thing about having sex when sober is that the other person usually is too. But she…definitely wasn't.

And that was a concern. Because, well, their whole group dynamic would be a more than a little sullied if he and Monica had a one night stand that she was destined to regret. But…if she wasn't going to regret it, then this could be quite the boon for him.

Because of the sex, duh. But also, if she was drunk and he was sober, well, that put him at an advantage, right? He could make this very good. For her. It was always going to be good for him. The most action he'd gotten since his break-up with Kathy had been when they'd gotten the free porn on the TV, and that hadn't even been great, since the porn had been in the living room and Joey was always home. He hadn't exactly been able to make good use of it.

So, basically, even the most mediocre of hookups could have gotten him where he needed to go. Probably embarrassingly quickly. But this was Monica. He'd have to face her after this. It had to be good.

They were naked. And they were definitely doing this, because the opportunity to bow out with any degree of grace or dignity had come and gone when Joey had.

And because she was kissing him again.

"Wow, I can't believe he didn't see my shoes," Monica said with a drunken giggle.

"Eh, he probably thought they were mine," Chandler said, putting a hand in her hair as he moved on top of her.

It was still in that fancy updo she'd had for the rehearsal dinner, but it had fallen just enough in the night that he could thread his fingers through it, tousling it slightly. Sex hair, and they hadn't even had sex yet. He closed his fist to give just the slightest tug to her hair without actively pulling. She moaned and he instantly knew he was doing something right.

Little did she know, he was just warming up. He remembered everything she liked from that little erogenous zone diagram she'd drawn up for him, and he planned to deliver. She wanted variety and sensation, intentionality and surprise. He pulled away from her lips to give her earlobe a little nip and she gasped. Yes, he could take his time…

Or not.

Chandler stopped his playful nibbling suddenly and pulled back an inch or two, eyes wide.

She'd jumped right to seven.

Her hand was clasped around his cock, giving it gentle pumps as she breathed heavily in his ear.

"Um, now I'd say our friendship is ruined."

Monica only giggled more, moving her fingers down to the base and giving his pubes a slight tug like he'd been doing to her hair and he hissed. A little bit out of pain and surprise, but mostly from pleasure. This woman was good with her hands.

"W-What are you doing?" he asked.

He'd thought him being the sober one and her being the drunk one would put him in control of the situation. It seemed Monica—ever-controlling Monica; he should have known—had a different idea.

"Making you feel good," Monica replied, her voice low and husky in a way he'd never heard from her before. The sound went right to his dick and he swore he felt a twitch before she began pumping her hand again.

"I thought I was going to do that," he said, his voice still sounding normal. Uncertain and unconfident. He moved his hand to start caressing the outside of her breast. "Seven erogenous zones? Have to hit them all and mix them up?"

"Well, there are exceptions to that rule," Monica said, her hand never stopping. "Like, for instance, if the girl really wants sex. And I, Chandler, really want to have sex. Right. Now."

She punctuated the last two words with firm squeezes to his cock and he gasped again. "Well, right now you're trying to make no sex happen. Or not for another ten minutes or so, anyway."

Getting the hint, despite her inebriated state, Monica took her hand away and brought it up to his chest, pinching his nipple. That might have elicited a gasp too, but he didn't want her to think that she had the upper hand. Which she absolutely, completely did.

"What about now?"

"Um, truth be told, I need to settle down a little bit if we want to be able to call what we're about to do sex," Chandler said with a wry smile on his face. Despite what he'd just said to her about 'speed' he didn't want to make good on that promise. He just wanted to set expectations low. "Just give me two minutes to, uh, try my hand at this."

Monica smiled. "Is try your hand a pun?"

Chandler brought his hand up to her face and wiggled his fingers. "Maybe."

Then he kissed her. He remembered faint recollections of years ago, back when Rachel had first come into their lives, when they'd had a conversation about kissing. How men just wanted sex and girls wanted to keep kissing. Well, if she let him, he had no plans to stop kissing her.

Except to make some detours. He moved his lips down to her neck—he'd never noticed what a long neck Monica had before—as he slid his hand up her thigh. He caressed her hip and then brought his hand in to the flesh of her inner thigh.

He kept moving his lips down, capturing one of her nipples in his mouth as he rubbed leg, both of them opening for him naturally as he lay in between. Just like he'd done to her earlobe, he gave her nipple a couple light bites before swirling his tongue, and then repeating.

His hand, meanwhile, crept a little higher. He'd seen from his peek under the covers that she wasn't bare down there—that had always crept him out, though, so he was fine with that—but now he could feel that she definitely kept things trim and tidy. He shouldn't have expected less from Monica.

He started rubbing her, feeling how slick her core already was. That was a blessing because, while he'd thought ahead with the condoms, he hadn't seriously though he was going to get laid, so he hadn't brought any lube with him to London. All they had was what was on the condom and what was between her legs.

So he wanted to make sure she was properly warmed up. He brought his hand just a little higher and began rubbing her clit—something he'd only found out about embarrassingly recently. Monica began to moan and he moved back up to capture her lips again, capturing the sound in his mouth.

"Chandler," Monica whined. Her throaty bedroom voice was gone and in its place was that of a desperate woman, falling apart at his hand. "Please."

"Please what?" he asked coyly, pleased, although a bit unsettled, to be back in control. He sped up his movements.

"Please fuck me."

Chandler's eyebrows raised and he almost stopped what he was doing with his hand. Monica never spoke like that, and the sound of the expletive brought him immediately to where she was. This was going to happen. And it had to happen now.

"Well, when the lady says please…"

Chandler felt around for the condom, panicking a little in the ten seconds it took to find it in the folds of the hotel comforter. Then, without grace, he struggled to tear the wrapper, wanting to make sure he didn't damage the condom. This was their only one; it had to count. It was all he could do not to talk it through its duties as he rolled it on himself, still painfully erect, despite having been on the bench for the last few minutes of activity.

Once the condom was ready to go, he moved back over top of Monica and captured her cheek in his hand, a gesture that felt inappropriately intimate for both a friend and a one night stand. Really, all he wanted to do was make sure that her eyes met his.

"Are you still sure?"

"Yes."

"You're not too drunk?"

"No."

"You're not going to regret this?"

"Chandler," Monica said, a bit of bite in her tone. "I want you to fuck me so hard I can't walk down the aisle."

At that evocative image, Chandler paused, looking at her with wide eyes as he saw whatever patience she had gradually leaving hers.

"Well, alright then."

And he plunged right into her. He didn't usually do that when he had sex—although, again, there was no usual when it came to sex for him. Partnered sex, anyway—but if she wanted him inside of her, by God, he'd be inside of her.

Monica groaned, the sound almost more that of relief than pleasure, and her eyes were already rolling back. He decided to see that as a good sign.

It always took him a minute to find his rhythm. He felt like perhaps there was a different set of muscles one had for sex that helped you thrust and stay upright and do everything all at once that he just hadn't used enough to properly develop. But, eventually, he found something of a stride.

It wasn't enough for Monica, though.

"C'mon, Chandler," she said, meeting his thrusts as hard as she could, the sound of their skin slapping together loud and filthy, even from under the heavy comforter. "Give it to me."

He wanted to say something back, but his breath was already leaving him and all he could do was give a grunt as he tried to put a little more force into his motions.

"That's it," she said, the throaty bedroom voice back for a moment. "Fuck me, Chandler. Fuck my pussy."

Chandler never would have pegged Monica as being one for dirty talk, but, as it was happening, all he could think was that those words were so hot coming out of Monica's mouth. She put one hand on his ass to propel him harder so that every thrust slammed into her full force. Maybe she really didn't want to be able to walk tomorrow.

He watched as she used the other one to grope her breast, no tenderness whatsoever in the motion. She clenched it, her pale skin suddenly bright red when she pulled away. Then she moved the hand down to her clit and began rubbing back and forth so quickly that the motion looked perfectly practiced. Of course it would be, but Chandler was suddenly hit by the image of her touching herself alone in her bedroom, just meters away from his bedroom in his apartment and found himself even more aroused by her.

Suddenly, he was compelled to take a hand and slap her ass. It was a little anticlimactic when it connected, his hand hitting the bed a little too much to make a good smack sound, but Monica still gasped and groaned, "Uhn, yes."

He squeezed her ass cheek in his hand, knowing he would leave a hand print there just like she had on her chest. She ground into it and her head fell to the side, her face looking euphoric with pleasure. He released his grip, putting his arm back in a better position for his balance.

With her head to the side, her neck was suddenly fully available to him, and he began nuzzling her, giving little kisses. He couldn't focus on much there, but her neck was too beautiful to resist.

"No…hickeys," Monica breathed.

For a moment, Chandler was shocked back into reality. Ross's wedding was tomorrow. He was having sex with Ross's sister. Ross and Monica's parents were staying in this very hotel as well. This was…wow, this was a really bad idea.

"What's wrong?"

Chandler was brought back to reality by Monica's voice. She was looking up at him, and he hadn't even realized that he'd pulled away from her neck. He'd been on autopilot for the last few seconds. But as he looked at Monica's face, cheeks flushed, beautiful blue eyes dilated, lips swollen from being kissed, he remembered who he was here for.

He was here for her.

He gave her one really hard thrust and they were back on track. He reached for her breast and pinched one nipple hard, making her arch her back. Monica moaned, head lolling back as he felt her speeding up her movements on her clit again. "Uhn, I'm close, Chandler."

"Me…too…" he grit out, struggling to keep his composure. But, despite his mind wandering, he'd already held on longer than he might have predicted, and everything Monica was doing to him was proving to unravel him quite quickly.

"Well then, come on. Fuck my little pussy."

And that did him in. Of course, he'd been fated to finish first. He gave it all that he had for those last couple thrusts, but her words quickly and totally pushed him over the edge, and he came hard into his condom. Luckily, Monica only needed a couple more passes of her fingers and then, just as he'd slowed to a stop, he felt her fluttering around him, letting out an ecstatic moan that could certainly be heard in the rooms on either side of his.

It was all he could do to keep from groaning, "Thank God," into her shoulder as he collapsed onto her. It would be embarrassing for her to hear that his first post-orgasmic thought was: "Thank God she finished." It wasn't like Monica wasn't aware of his less than illustrious reputation as a lover, but he hoped not to bring that into this room at least.

"That was amazing," he said instead, a statement that definitely did outrank that other one.

After a moment of crushing silence—save for the heaving breaths between the two of them—Chandler heard Monica whisper, "It was."

Then he lifted to find her eyes closed and her breathing evening out as she fell asleep. Chandler smiled a little, smoothing her hair and adjusting the pillow just a little bit. Then, with the slight discomfort of sneaking around, he pulled out of her, already beginning to soften. He carefully rolled out of bed, trying not to disturb Monica even though he doubted much would wake her up right now. He withheld commending the condom for its valiant service and dropped it in the wastebasket.

He padded over to the bathroom and took a couple of seconds to wash up before he was struck by how exhausted he suddenly was. It still wasn't even 10pm, but he did have jetlag working against him after all. Without taking the effort his pajamas back on, he slipped back into bed, waffling over how close he should get to Monica. She was taking her half out of the middle, though, so out of fear of falling out of bed more than anything else, he scooted up to her and took the opportunity to run a hand down her side.

She really was the most beautiful woman he knew in real life. She had such a stunning figure with a beautiful curve he could feel under his hand as he wrapped his arm around her waist. He wasn't much of a cuddler, so he knew he would roll away from her naturally before she ever woke up to find him like this.

He fell asleep long before he could ever make good on that.

One of three.