Hello my friends!
This one is rated M if you didn't catch the rating. So if adult sexual themes aren't your thing, you won't be into this one-just a fair warning. These chapters will be in canon (as much as possible) sexy moments from season 1-4 before our dynamic duo got together.
There will be multiple chapters-I'm not sure how many, but I am going to navigate between their relationships on the show (with Janice, or Richard, or Kathy...). I think I've written them so you kind of know what episode I'm around, so I'm not going to put that at the beginning. If I didn't make it obvious enough and you want to know, please reach out and I'll reply. :)
I hope you enjoy! Please let me know your thoughts!
"Alright, I'm off to bed," Rachel announced, yawning loudly. The movie had just finished and Monica's roommate wasted no time and heading for her bedroom. She stood from the couch and gave the only two friends left a wave, "Night guys."
"Night," Monica said, and Chandler returned the wave as the door closed behind Rachel. "God, I'm tired," she yawned a little, "work was insane today."
"Yeah?" Chandler asked, leaning his head on his hand, resting them both on the arm of the couch.
"I don't think I sat down once."
"Well, here," Chandler lifted his head and moved both of his hands to lay on her legs that were on his lap, "Will a leg massage help?"
"Yes, oh, God, thank you," she moaned softly.
He didn't even remember when she'd switched from the sitting position next to him to laying down, her head in the middle of the couch and her legs stretched across his, but he didn't care. "So, did you like the movie?"
Monica turned her head to look at him, smiling a little, "Eh, it was okay."
Joey left in the middle of the movie for a date, Phoebe fell asleep during the movie, so she excused herself to head home, and Ross offered to walk her there, not having much interest in the romantic comedy, so the three of them were the only ones to make it through.
Chandler chuckled at her and tapped her knee with his knuckle, "Just okay?"
She shrugged one of her shoulders, "I just think it's really, really unrealistic."
He turned his head a little, "What is?"
She rolled her eyes dramatically and sat up, but didn't move her legs from his lap, "Falling in love like that."
He chuckled again, picked up his beer, and finished the last sip of it, then sat the empty bottle back down on the table next to him. He squeezed the space just above her kneecap gently, "I think it's true for most people that it doesn't happen until it happens, right? And then when it does, it probably seems like that."
Her eyebrows went up further on her head, "What?"
He didn't know what she was confused about, "What what?"
"I didn't think you, Chandler Bing, would ever say something," she poked his arm and chuckled at him.
He licked his lips, "What are you saying?"
She smiled at him, "Just, you know, your whole fear of commitment thing."
"Ah, that," he cleared his throat a little and shook his head. It was the reputation he had, and he knew that he earned it honestly over the years. He'd shut down a lot of relationships just when things started to get serious, but it wasn't because he didn't want to be committed to them, it was because he didn't like her enough to continue the relationship. But he thought that no one really understood how he really felt about finding someone to spend the rest of his life with, because he wanted it. A lot.
"Actually, I would classify it more of a phobia of failed marriage rather than a fear of commitment," he scratched the side of his nose, "because I do believe in love."
Her mouth fell open a little, "You do?"
He nodded at her, "Yeah, I do," he confirmed, "but that doesn't mean that I want to marry the first girl I seriously date. I just would like, you know, to have the romance part of it."
"And the sex?" She asked, her eyebrows raised. He smirked at her and both chuckled softly.
"Well, of course the sex," he squeezed her leg again.
That brought her memories back to the last sex she'd had with Paul the Wine Guy. The man only cared about himself, and she really didn't even enjoy it, and now regretted any time spent with him at all, not just in her bedroom.
"What's on your mind?" He broke the silence between them, and she lifted her eyes to his.
"Just thinking about how my last three dates have been not even worth my time."
He nodded at her, then began to knead her leg a little, "Yeah, I know how you feel."
She shifted in her seat and smiled at him, "That feels good."
"Yeah?" He asked and pressed harder into the fabric of her jeans as he continued to knead her legs. "You really liked Paul, didn't you?"
She looked up at him, then shook her head, "I thought I did, until I learned that he told me some sob story to get me to feel bad for him. He tricked me into sex, and I'm an idiot for allowing that to happen."
Chandler pressed his lips together. He remembered Joey teasing her about not knowing that Paul's weak story about how he couldn't perform sexually for two years was a line. Chandler didn't comment, but he hated the fact that Paul used her like that.
"You're not an idiot, Mon," he responded, shaking his head.
"I am," she argued softly, "I should've known better."
"Well, the sex was good, at least, right?" He looked up from her legs, an eyebrow raised as he waited on her response.
She chuckled softly, "Why would you think that?"
"I saw the smile on your face the next morning," he pointed out, "so I concluded that you must have had some great sex."
She scrunched her nose up at him and shook her head, "No, it wasn't great at all."
He lifted an eyebrow at her, surprised, "Really?"
She shook her head, "I was smiling because I was excited about the possibility of things going somewhere with him, I guess. But he was actually very bad in bed."
Chandler looked down at his hands as he kneaded her right leg, "Gotta be honest," he started, "I'm surprised at that."
Monica chuckled at him, shaking her head. It surprised her a bit when she learned that it wasn't awkward or weird talking with Chandler about sex.
But he was her best friend, so she wasn't sure why. She knew she could tell him anything.
"He only cared about himself," she continued, and he brought his eyes up to hers. She stared into the beautiful blue, then moved closer to him so she could whisper, "I didn't even have an orgasm."
His hands that were massaging her legs paused, and the look on his face made a chill go through her. Again, she wasn't sure why. It was an intense, disbelieving look as he studied her, and she didn't know how to feel about it.
"Seriously?"
She bit her bottom lip for a moment and kept her eyes on him, "Yeah, seriously."
"Well, that's just…" He trailed off, then squeezed her leg, "That's really, just…"
She chuckled at him, "Just what?"
He looked away for half a second and eventually brought his eyes up to hers again, "I don't know why any man wouldn't want to make sure you're…" he looked down at her body, "…taken care of."
"I guess he didn't care for me like you do," she pointed out, then waved a hand, "It doesn't happen all the time anyway."
He lifted an eyebrow, "What?"
She shrugged a shoulder, "Not every time."
He stared at her in disbelief, "That's ridiculous."
She chuckled lowly, "Oh, so you would make sure every time?"
"Without a doubt," he answered quickly, not looking up from his task.
She lifted her eyebrows at that, then shook her head, "Paul the wine guy didn't have such beliefs. He did nothing but leave me sexually frustrated," she sighed softly.
"Frustrated, huh?"
She nodded at him, "I just feel like I'm…bottled up."
He turned his head a little, "Bottled up?"
"I think the cure would be a good, toe-curling orgasm to feel better."
"Yeah?" He looked up at her with a smirk on his face, "I could help you out with that." She smirked back at him and blushed as she looked away.
"Then after the horrible sex with Paul, Joey begged me to go on that awkward double date and dealing with my mom a couple of weeks ago," she groaned, her fists balled up tightly, "it's all just swirling around inside."
Chandler nodded, "Mon, Paul is a jackass, don't let him get to you, try to get him out of your head. He just used you, and I don't like that. he said, "I never liked him."
She didn't point out that he barely knew the man, because she guessed that she didn't either, but she could tell by Chandler's demeanor when Paul was around that he really didn't like him.
"Yeah," she agreed softly, "you're right." He held her stare for another second, then looked down as hands resumed kneading her legs, and she shifted again so that she was more comfortable. "You're good at this, Chandler," she said, "I think you could give Phoebe a run for her money."
He smiled, "Thank you, but don't tell her that."
"She'd never let you live it down," Monica replied, and both chuckled. Silence fell over them for a few long seconds until he looked up at her.
"So, I guess you're owed one orgasm, huh?" She looked down at his hands as he kneaded her leg, then looked at the side of his face. There was a small smirk there as he concentrated on his task, but when he looked at her, she saw a seriousness in his eyes that wasn't there before.
She giggled a little, and he smiled again, breaking the slight tension between them, "We can't do this," she said, "you're my friend."
"You're my friend," he responded, then lifted and dropped his eyebrows, "you're probably right," he conceded, then resumed kneading her legs, "it's not a good idea."
She swallowed hard, watching his hands, his long fingers on her legs, "It's not."
"I should probably head home," he mentioned softly.
She nodded slowly, but her insides were screaming. She didn't want him to go. She wanted his hands to stay on her. But not over her clothes.
She swallowed hard and broke the silence, her voice soft and slightly shaky, "Were you offering?"
He lifted his head to look at her, "Hm?"
She kept his darkening gaze for a second, swallowed hard, and licked her lips. She felt her heartbeat speed up as she placed her hand on his and slowly moved it toward her inner thigh. She knew he could feel the hotness of her skin through her jeans.
He cleared his throat as he chuckled, but she knew it was because he was suddenly nervous, "I um…"
"You were offering to give me one, right?"
He nodded once, "Yeah," he managed, but barely. He stared into her eyes again, shaking his head slowly, "But, we're friends, and we shouldn't, right?"
"Probably not," she answered, and he nodded and looked away from her again. A few seconds passed and she cleared her throat, causing him to look up at her. She smirked at him, "You know, friends help each other out," she said with a slight shrug of her shoulder, "and you'd be doing me a favor."
"A favor?" He questioned, his pulse quickened at the look on her face and the tongue that darted out to moisten her lips.
"Yeah," she said softly, "I'm uh…" she bit her bottom lip for a second, "…bottled up."
He let his eyes rake over her body and swallowed hard.
He was used to having hot female friends, he had three to be precise. Rachel and Phoebe were both gorgeous too.
There was something different about this one, though. Monica was exactly his type, with her beautiful blue eyes, her dark hair, perfect smile, and smoking hot body that he'd honestly love to get his hands on.
"Can't have you…bottled up," he told her.
"It's not good to be that way."
He met her eyes and studied them carefully. He didn't see the teasing grin she aimed at him when she was trying to make him laugh, and he didn't aim one at her either.
There was a seriousness to the moment that he couldn't figure out, and he swallowed hard at the thought of touching her body.
He looked down at their hands and slid his up a little, "No, wouldn't want that," he murmured lowly. He met her eyes again, "Are you sure?"
Truthfully, the gentle kneading and rubbing he was doing on her legs already had her a little on the hot and bothered side, not that she'd ever tell him that.
And for some reason that she was choosing to ignore, it didn't feel weird to her for her to ask him to help her out with this particular favor.
"I'm sure," she answered, and he moved his hand closer to her hips.
Her breath caught in her throat as she felt her whole body react to him. He moved his hands from her and turned himself so that he was facing her completely. She bent her knees and he placed his hands on them, then gently maneuvered her right leg so that it was sandwiched between him and the couch.
He leaned slightly closer to her and rested his hands on her hips at the top of her jeans.
"Lay back," he instructed, and the sound of his lower, huskier voice sent a wildfire through her. She leaned back slowly on the couch, and her breathing sped up as she felt his fingertips graze her skin.
What in the hell were they doing? She didn't know.
Chandler was definitely her best friend. Sure, she had Rachel too, but her friendship with Chandler was different. He was the one guy she could count on, no matter what she asked, so she supposed now shouldn't be that shocking.
Of course he wanted to help her out.
Now that she thought about it, she was actually in disbelief that they had never done anything like this before.
She watched him carefully as he looked down at her chest, then rested his hands on her rib cage. She arched her back into his hands, encouraging him to move things along.
"Touch me, Chandler," she whispered, "I trust you."
He looked into her eyes, licked his lips, and nodded once as he ran his hands over her breasts. There were two layers of fabric still between his hands and her breasts, but she felt her nipples harden anyway under the weight.
With shaky fingers, he began to unbutton her white shirt, but he wasn't having much success. She was becoming so eager to move things along that she lifted her arms to help him.
Once the last button was finally undone, the look on his face as he studied her now mostly exposed top half sent more chills through her.
He returned his hands to her breasts and massaged them over the fabric for a few seconds before glancing over at Rachel's door.
They didn't talk about it, but he was sure that she, like him, didn't want their friends to know anything about what he was doing to her. It was none of their business, and frankly, he thought the thrill of doing it in secret was more appealing than if everyone knew.
Monica saw the glance to her roommate's door and placed a hand on Chandler's arm reassuringly, "She's a heavy sleeper," she whispered.
He smirked at her, then leaned down closer to her face, "What about when you scream?"
She shivered at his words but tried to keep a cool exterior. He wasn't going to win this.
Okay, he might win, but she was the one that was getting the prize.
"I've got pillows," she responded as confidently as she could, but gasped when he pulled her left breast over her bra cup and pinched her nipple.
He felt his mouth water as he did the other the same way, but he supposed he didn't have time for such things, not right now, anyway.
He spent some time with her gorgeous breasts and slid his hands down her body, resting them on her waist.
He pressed his thumb into the center seam of her jeans, and she let out a moan that sounded so good to his ears. He slowly unbuttoned her jeans and let down the zipper, and she began to squirm.
"Chandler," she said breathlessly, and he grinned at her. He took another second and ran a hand through his brown hair before he placed his hands on her hips, then gripped her jeans and pressed his fingertips into her hips before he pulled them down.
She planted her feet on the couch and lifted her butt into the air so he could get them down easily. He slowly took the jeans off her legs and discarded them on the floor next to the couch, "You should look into more skirts," he said softly.
She chuckled lightly but it turned into a moan when he slowly ran his hands over her body again.
He sat up straight and admired her for a moment, just her undergarments left on her body.
"You're so goddamn hot, Mon," he murmured lowly.
She smirked up at him and lifted her hips, again urging him to move things along. He smiled at her again, and adjusted himself on the couch, mostly because his own pants were feeling tighter by the second.
But this wasn't about him. It was about her.
He slid his hands to her inner thighs, his fingers dangerously close to where she wanted them most.
He finally moved them up and bushed his fingers across her panties, and she gasped as her hips lifted off the couch again.
"You really are bottled up, huh?"
She groaned, her impatience getting the best of her. She usually didn't mind being teased, but now was not the time for it. She wanted more, and now.
But before she could muster up the energy to put on a mad face and be angry about how tantalizing slow he was moving, she felt his hands touch her again, his fingers feeling the fabric of her underwear, dipping beneath to touch her skin just briefly.
He eventually put his hands on her hips, then pulled the garment away from the main prize, down her legs and onto the pile of jeans next to them.
"My God," he whispered as he slid his hands along her perfectly smooth legs, admiring her fully as her legs fell open in front of him.
His mouth watered again, oh, how he'd love to taste it.
Normally, doing this in front of someone who'd never seen her before made Monica incredibly nervous, but she wasn't. Not even a little.
She was…excited. Ready. Willing. Impatient.
She supposed that was because she was completely comfortable around him, her best friend, and she trusted him with this, what he was about to do to her.
He brushed her clit with the softest feather touch he could get away with, then smiled as her breathing sped up to a pant and she jolted as if she'd been shocked.
"You're soaking wet," he whispered, then dragged his fingers up her folds to gather some of the wetness onto them.
"God, Chandler please," she begged softly, almost at a breaking point.
He nodded at her, wanting to tease her more, but thought better of it. He could tell he'd done enough.
He slowly inserted one finger and she moaned again and grabbed at the couch. He began to move his finger in and out, then moved his other hand to her clit to give that some attention too.
"Oh God," she moaned, stretching her hands above her head as she pushed her entire body into the couch.
He curled his finger inside her just a bit and she gasped and gripped whatever she was holding tighter.
He bit his bottom lip as he concentrated on what she liked best. Touching her one place made her moan like that, curling his finger made her gasp and cry God's name, rubbing her here made her arch her back; he wanted to commit them all to memory.
He felt like her orgasm was beginning to build and he didn't want it to be over so soon, so she whimpered softly when he pulled his finger out of her just as she began to feel a release build in the pit of her belly. He dragged it up her labia and pressed against her clit and she almost screamed to the ceiling.
"Damn it," she said softly, and it only made her angrier when he smirked at her.
"I'm gonna let you get there," he promised, and suddenly he was completely forgiven when he put pressure exactly where she wanted it.
She decided that she should get that pillow she mentioned earlier, because if this man kept teasing her and producing pleasure, she was going to need it.
She reached above her head and grabbed the throw pillow from the end of the couch just as he repeated the action, causing her head to swim.
She suddenly felt a bit of wetness on her nipple as he returned his hands to them, pinching and teasing them before slowly dragging them down her body, past her hips and inner thighs, and right back to her center.
He returned his hands to their previous position, "God yes," she moaned, arching her back again, trying to force more pressure that she so desperately craved, "just like that," she pleaded.
"Yeah," he said in response, then moved his hands and fingers a little faster.
Chandler thought for a second of dropping to the floor on his knees to taste it, because dear God, the smell of her was so tantalizing. But he didn't know if he could get away with that. This was already a giant leap in their friendship, and he did not want to push it any further if she didn't want such things.
What a pity, because if she tasted as good as she felt and smelled, he was missing out.
He shifted again at the thought, because the sounds she was making as she tried to control her screaming, the way she looked as she panted and tried to regulate her breathing, the way she felt in his hands had his bottom half extremely uncomfortable by this point.
He slipped a second finger inside of her and she gasped, then moaned loudly, "Yes, Chandler!" She whined, begging him for more, "Harder! Please, harder."
"Shhh," he chastised, then looked over at Rachel's door worriedly, but didn't stop with his fingers, so she didn't complain too much.
She lifted her arms and rested her hands on his forearms, just below his sleeve. Her nails dug into his skin, "More, please," she panted, "please."
He groaned softly, a little worried that much more pressure against her would hurt her, but he wanted to give her what she wanted. He curled his fingers inside her and pressed against her harder.
"Yes, just like that," she said breathlessly, her head burying into the couch behind her again, her back arching.
He knew she was getting close, not only because he could feel the delicious contractions around his fingers, but her breathing was rapid, and she was moaning with nearly every move now.
"Come on," he encouraged softly, then pumped in and out of her at a faster, rapid rate.
She let go of his forearms and grabbed the pillow, pushing it in her face as she came, her body shaking as her orgasm rippled through her.
He slowly removed his fingers, and he heard a muffled noise leave her mouth as he did so. He ran his hands down her legs, resting them just below her knees.
She didn't move the pillow until she felt her breathing return to semi normal. When she did moments later, she looked up at him and grinned at him.
She felt his hands move to the back of her legs, behind her knees. She slowly sat up on her still shaky arms to look at him, "That was incredible," she said softly.
She expected a confident 'I told you so' look on his face, but it wasn't there. She found a look of curiosity instead as she took more deep breaths.
"Yeah?" He asked, and she smiled and felt a blush come to her cheeks.
"Amazing," she confirmed, "and just what I needed."
He grinned bigger, "Good," he ran his hands up to her thighs, "I'm always happy to help you out." He watched her as she lay there, her chest heaving slowly as she recovered.
Good God, she looked so good. He licked his lips and bit the bottom one as he slowly slid his hands back onto her thighs. He wanted to do that again, under one condition.
"You should get another," he voiced.
She shifted her hips and moaned softly, "You think so?"
He hummed a little, "I do," he agreed, "but I need you to do something this time."
She lifted an eyebrow at him, "And what's that?"
He smirked at her and leaned forward just a bit, "I want to watch you," he murmured softly, "so if you could please keep the pillow away, I'd be so grateful."
She felt her face burn with blush, her heart rate increase, and her breathing speed up at the look on his face. She smiled back at him, "I think I could make that happen," she responded coyly.
He smiled at her fully and pressed his thumbs against her inner thighs, "I really want to taste it," he mentioned.
The excitement that grew within her would've been embarrassing if he could see it. But in their current position on the couch in the living room, Rachel's proximity to them, and how he made her feel just by touching her, she knew she couldn't keep her voice down enough to let him do such things.
"That's probably not a good idea if I'm to keep quiet," she said, a slight whimper in her voice.
He nodded understandingly, although he was super disappointed. Maybe, by some miracle, he'd get the chance to do it one day.
He thought that just once wouldn't be enough with her.
He pressed his thumbs into her skin again and shifted in his seat at the thought. He looked up at her, ran his hands over her torso when she laid back again, and then back down to her core.
She moaned softly and took in a deep breath, trying to calm down her excitement of what was about to happen to her for a second wonderful time tonight.
He began to touch her, his fingertips dancing wonderfully exactly where she wanted, "You're so good at this," she breathed, grabbing at the couch because she already felt herself building.
"I'm glad you think so," he responded huskily.
She was impressed that he already knew what she liked, because he was repeating the same actions that sent explosions through her earlier. She looked up at his face, his eyes focused on her as pushed one, then a second finger inside her again.
"That's it," she confirmed, and her eyes shut against her will as her head burrowed in the couch behind her once again, "God, yes, just like that."
Chandler contorted his wrist and stroked her like that repeatedly, "You're close," he whispered.
"God yes," she said loudly, then grabbed at his forearms again.
He was about to remind her that she needed to be quiet, but the look on her face, the way her back was arched, and her nails dug into his skin, he didn't think that he much cared if Rachel or anyone else heard her anymore.
"Give me another one," he encouraged, curling his fingers to hit that spot that he found before. He made sure to keep his eyes on her face, because he knew she was about to fall over the edge, and like he told her, he wanted to watch.
A few more seconds of well-placed pressure and angling of his fingers was all it took for her to do just that. Her toes curled, her nails dug painfully into his flesh, she began to shake just a little, and good grief, the way her face looked turned him on more than just about anything else.
He kept working her, stroking her slowly, trying to get every bit of what was bottled up out of her. It was the main goal, after all.
Once her entire world stopped spinning and she returned to planet earth, she opened her eyes to gaze at him, just as he removed his fingers from her.
He looked at her at smiled just a little, resting his hands just on the back of her legs again.
"Oh my God," Monica managed, attempting to return her breathing to normal. She smiled back at him as she lifted herself to sit up, "Thank you," she said.
"There is absolutely no reason to thank me," he responded with a shake of his head.
She lifted an eyebrow, "But you did me a favor," she reminded him.
He chuckled just a little, "I hope this doesn't come across as me sounding like a total jerk, but I will do this kind of favor every single day if you want," he leaned toward her a little, "as long as I get to watch your face."
She laughed softly and shook her head, then met his eyes again, "I'll keep that in mind," she teased, her voice lower.
He squeezed her calves as she lifted her hands and put her breasts back into her bra, "I'm gonna miss those," he mumbled, and she smiled at him again and chuckled.
"Shut up Bing," she replied, making him laugh too.
She reached down for her panties and moved her legs from his grasp, then slipped them on as she maneuvered her legs from the couch. He turned to sit correctly too, just how they were sitting when the movie started three hours ago.
After she put her jeans on again, she turned to him and smiled, then tucked a piece of hair behind her ear. After a moment, she pulled him into a tight hug, and he returned it, tightening his arms around her.
She finally pulled back just a little, but kept her arms locked behind his neck. She looked down at his lips, and he looked down at hers.
He licked his lips but shook his head slowly.
She nodded back at him, understanding what he was trying to say. They had an ability to have a conversation with no words, and now was no exception.
"You don't want to kiss me," she said, her words not a question.
"Of course I do," he answered quickly, and she wondered if he was going to lean forward and do just that. But he only shook his head again, "But if I kiss you," he began, then swallowed hard, "I probably won't want to stop."
She smirked at him, "You think I'm just that good of a kisser?"
He met her eyes again, then leaned forward, his lips tantalizing close to hers, "I have no doubts that you are," he responded, "but we're friends."
She nodded in response, "Yeah," she said softly.
"I'm not sure friends make out with each other after favors." He raised an eyebrow at her.
She studied his eyes, his gorgeous, sparkling blue eyes for a moment, wondering what was running through his head.
She supposed he was right, although kissing him was exactly what she wanted to do. His lips looked so soft, his hair at the perfect length to run her fingers through.
"Probably not," she whispered softly, then released her hands that were around his neck, but she still leaned forward and pressed a kiss to his cheek.
He smiled at her and squeezed her arm as he backed away, "I'm going to head home."
She nodded slowly, swallowed hard, and smiled back at him, "Thank you, again, Chandler," she whispered.
He winked at her and squeezed her hands, "No, Mon, thank you."