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Friends: More Sex-Ed for Chandler

Chandler walked into Rachel and Monica’s apartment one morning, with a look of obvious frustration on his face. Monica was sitting at the kitchen table eating toast and orange juice.

“Hey there, lover boy. How are things going with Kathy?” she teased.

The week before, the roommates had given Chandler some “tips” on pleasing Kathy, with Monica coaching as Chandler practiced on Rachel.

“Oh fine,” he said disgusted.

“Is Rachel here?”

“No, she’s already at work at Bloomingdales. What’s up?”

“Well, it’s just that… okay… Kathy’s been… agreeing with me… A LOT during sex… you know, since you guys helped me out last week. “

Monica smiled, pleased with herself. “Yeah, yeah, you should have seen her running in here the next morning to thank me… well, and Rachel too. “

“Yeah well, things have been pretty good for the last seven days…”

“You’ve done it every night since then? I’d say you’d doing REALLY good, stud!”

“Yeah, until last night… she, she wanted me to do something… different.

“Like what?” Monica asked, confused.

“Like… rear-u-lar… things. “

Monica tried to hide her giggle.

“Ohhh, I understand. Kathy wanted anal sex. “

“Yes, she wanted ‘anal sex’,” he responded sassily, irritated at himself more than anything.

“So what’d you do?”

“I, I froze. I didn’t know what to do. So I just went into her ‘the normal way’. It was fine and all.

And she agreed with me as much as ever. But, but I just wanted to do that for her, you know? So I was hoping that maybe you and Rachel could help me again… like, like before… with you telling me what to do and Rachel letting me practice on her. “

“Well, as much as I like telling people what to do…” Monica paused, then laughed knowingly, “yeah, I don’t think Rach would do that.

She’s still a virgin… in that area, at least… and I’m pretty sure she wouldn’t change her mind just for you. “

“Great… and now… and now my girlfriend’s gonna break up with me because I won’t do her in the ass. “

Frustrated, Chandler got up and started to go.

“Wait, Chandler,” Monica said, brushing the crumbs from her fingertips. She took a sip of juice.

“C’mon,” she said getting up and walking to her bedroom.

Chandler followed her, and she closed the door behind him.

“Okay. Take off your clothes,” Monica said, as she started to disrobe.

Chandler looked at her. “Wait a minute. You mean, you… you’ve done… ‘that’… before?”

Her high heel boots were already kicked to the side, and her pants were quickly coming off. She stood there in a thong and tight long sleeve shirt that clung to her arms and chest.

Monica smiled coyly, “I have some experience…”

She pulled her shirt off, over her head and shook out her short bobbed hair. Then she continued, conversationally.

“One guy told me that I had ‘an ass, made for fucking’…” she smiled, “but whatever. “

“Well, all right then,” he said, cheerfully. “Thanks, Mon. “

As they stripped naked, it never seemed strange to them that the subject was anal sex.

It was as if Monica was going to be teaching him how to bake a cake.

“Okay. Get into bed,” Monica said, pulling back the covers and climbing in. Her nude friend joined her. “Now, in the drawer beside you there are condoms, a towel, and a tube of lubricant. Why don’t you grab all that now. “

“Condoms, huh? I didn’t think girls could get pregnant that way,” Chandler said, laughing at his very bad joke.

Monica smiled, tolerantly.

“Well, it’s up to Kathy if she wants you to use one. But for me, if I’m gonna give the guy a little ‘oral action’ to finish him off, I don’t want it in my mouth after it’s been up there. “

“So I’m gonna get some oral action too, huh?” Chandler said, intrigued.

Monica gave him a sultry look, “Depends on how well you do.

Let’s just call it… your incentive plan. “

As Chandler pulled the items out of her nightstand drawer, he questioned, “So you always keep this stuff nearby?”

“Like the Boy Scouts say, ‘Always Be Prepared. ‘”

“Well if you were in the Boy Scouts, you would have been the most popular Scout in my troop… and you probably would have gotten some interesting Merit Badges. “

Monica laughed, “No, silly, I wasn’t in the Boy Scouts.

But I dated a former Boy Scout. “

“Who?” Chandler inquired.

“Richard,” she replied nonchalantly.

“Ohhh, Richard,” Chandler said flatly, remembering who Monica’s last boyfriend was. He immediately imagined how Monica would be comparing him to “that mustached bastard”. She sensed this and comforted him.

“Chandler, trust me. You won’t disappoint me. And I KNOW you won’t disappoint Kathy. “

Monica’s hand went under the covers to Chandler’s soft penis.

“So first, let’s get you good and hard,” she said as she began to fondle him.

Chandler lay there for a few moments, letting Monica stroke his dick. She was watching the bump in the covers move back and forth. He looked at her beautiful face. Perfectly formed mouth. Her red lips.

He kissed Monica. This almost surprised her, but in a split-second, she was happy to join in.

They made out in bed, as Chandler cupped her medium-sized breast. His rod quickly got hard in her hand; yet with her objective reached, she still kept stroking it, enjoying his attention.

“Rachel was right. He is a good kisser,” she thought.

Monica could feel herself getting “hot and bothered” as Chandler’s kisses became more passionate, and his hand roamed her breast, neck, cheek, and through her hair. She cleared her throat as she pulled away slightly, discretely licking her lips.

“This is, um… good. Very… good. Because… you’d be having, uh, foreplay with Kathy before you… you know… so we should, um…”

She fell back into his kisses, returning them with equal passion. Chandler’s lips soon drifted away from her mouth, to her neck. Monica settled onto her back. A lusty sigh escaped from her. Then she giggled as he began nibbling on her earlobe.

Monica took his face in her hands and breathed deeply as she tasted his mouth, once again.

Then she moaned softly as his tongue left her own and traveled to her shapely breast. A louder moan came as he sucked on her pretty pink nipple.

His hand glided the length of her body, from breast to ankle. She curled her leg up, responding to his touch, and wanting him to caress her.

His fingertips traced little circles on her abdomen, scant inches above “Number Seven”.

“Mmmm… he’s learned his counting lesson well,” she thought, with a little grin.

Chandler’s fingers were teasing her into wanting more intimate touching.

“Do it,” she whispered.

Chandler barely brushed his fingers on Monica’s clit. She gasped and her body shivered. Then the flesh of his finger met the flesh of her clit. He slowly pushed it across her button.

“OHHHHHhhhhh,” she moaned.

As Chandler rubbed Monica’s clitoris, his tongue explored her breasts, neck, and mouth. She was getting VERY aroused by all his actions.

Without a word, Monica tossed the covers back, reached between her thighs and pushed Chandler’s middle finger into herself, as her head went into the pillows and she groaned her pleasure.


Monica began panting as his hand settled into a slow rhythm.

“Finger me, Chandler… oh, god… finger my pussy. “

Her lips were sealed tight as she watched his digit travel in and out of her.

“Mmmmmhhhph… mmmmhhhppphhh…”

Right then, Monica didn’t give a fuck about anything but being masturbated. She had abandoned Chandler’s cock, and her fingertips roamed the insides of her thighs, bringing little tickles and tingles to her body.

Chandler, for his part, wasn’t content only to frig Monica, especially once she had stopped stroking him. He pressed his hard prick against her thigh and slowly rubbed himself up and down her leg.

Her soft skin felt good against his rod, and it easily kept him quite firm.

Chandler leaned in and kissed her. Monica’s hungry tongue probed his mouth, moaning into it. She looked into his eyes. What the hell, she’d say it…

“You know… since, uh, you and Kathy would be… um…” Monica swallowed as she paused. “…then maybe we should… y’know, just for Kathy’s sake. “

In his mind, Chandler instantly filled in the blanks.

“Oh… sure… absolutely… I, I need to make sure I can do all this right… I mean… for, for Kathy. “

“Yes, yes, anything for Kathy…” At the end, her words were smothered by Chandler’s mouth.

Their mouths remained locked as Chandler laid on top of Monica. She felt her heart flutter as she anticipated what would come next.

“Go in me, Chandler,” she whispered.

He pushed into Monica’s tight cunt.

Chandler groaned as she whimpered, “Oh god…”

Sure, she enjoyed her dildo collection, and Rachel’s fingers and tongue were fulfilling, in their own way. But right then, she needed a hard, warm, fleshy cock.

Chandler’s butt started humping up and down as he slowly began fucking his “teacher”.

“Fuck me, Chandler,” Monica said with a seriousness that divulged complete need.

Chandler felt her breasts and nipples pushed against him.

Her flat, toned stomach heaved against his. He swam in her ocean-blue eyes.

Their mouths met again, as Monica’s hands caressed his shoulders, arms, and back.

Chandler did her slowly, letting her luxuriate in every moment of his cock rubbing her pussy. Fists formed in the blankets, as Monica pulled them tightly around their joined bodies. She was moaning deeply as he fucked her.

“Yes, Chandler… oh, yes… ohhhh… uuuhhhh… omigod… omigod… mmmm….

Monica brought Chandler’s mouth to hers and gave him a long torrid kiss. Then realizing that she was getting lost in the passion, Monica tried to re-focus on the “educational purpose” of their endeavor, as he continued sliding slowly in and out of her.

“Right, right about now… um… the, the girl’s probably ready for you to… oh god… to, um, go in her… ohhh… her ass…”

“How, how do you know that?” Chandler panted, wanting to learn.

Monica looked at him, lustily, “Because I want you to fuck my ass, Chandler. “

Chandler pulled out and knelt beside Monica as she tore open a condom. He enjoyed the attention of her fingers as she rolled it onto him.

Once it was in place, Monica jacked him and fondled his balls, though not for his sake. But rather, she simply wanted her hands on a guy’s genitals again.

Monica enjoyed being a woman, but truly, she loved fucking a man.

“Lay behind me,” she directed as she reclined on her side.

Chandler moved into place. “Aren’t you forgetting that lubricant? Wouldn’t it be easier with that?”

She didn’t even look at him, “Just put it back in my pussy. That’ll be enough for me. “

Chandler lifted her upper leg and hooked it back over his own.

He placed his cockhead against Monica, and rubbed it along the her pussy lips. Then he quickly shoved his dick into her wet pussy.

Monica gasped and clutched the mattress. He slowly pumped her a couple times, as her gasp turned to moans.

“Mmm, yeah… now tease my ass with it. “

Chandler withdrew and ran the tip of his cock slowly between her cheeks, from her pussy to the small of her back.

Then he pushed his hips forward to let it settle it’s full length in the crevice of Monica’s small ass. He slowly humped her like this, tantalizing her asshole.

“MMMMmmmm, that’s all very good,” she moaned. “Now, now hold it and let me push back onto it, to get you in me. That way, the girl can control how slow or fast it happens. “

Chandler held his cock, so the little pucker of latex was resting at her entrance.

Monica took his hand, holding onto his thumb, as she pushed back onto him.

At first, nothing budged. Then Monica rotated her pelvis back slightly, spreading her cheeks a bit more. She started a gentle pulsing with her pressure, and felt the cock begin to penetrate her ass.

“Yeah, that’s it… hold it right there… mmm… yeah… let me, let me do it… slowly… omigod… yes… oh, yessss…”

Inch by inch, Monica screwed herself onto Chandler’s dick.

Her grip tightened around his hand. Her eyes were closed as she concentrated on the carnal sensation. She groaned as she slid the last couple inches, and her cheeks touched Chandler’s abdomen.

Chandler caressed her arm and thigh as she paused, enjoying the feeling of a hard cock filling her.

“Okay… okay,” she said, trying to gather her thoughts, “Now, you can start… but gently at first. “

Chandler was already surprised that Monica wasn’t in pain with all this.

So, not wanting to hurt her and being a little uncertain about what might be painful, he carefully began sliding his cock in her ass. Just a couple inches, back and forth.

“Mmmmm, yeah,” Monica softly encouraged. “That feels really good, Chandler. “

Emboldened, Chandler lengthened his thrusts; yet still slowly, still gently.

“Oh… yeah…” She was reveling in this. “With… with you and Kathy… in this position…” Monica began.

“Focus, Monica, focus,” she thought, then she went on.

“…there’s a lot you can do for her while you fuck me… I mean, her… while you fuck her… um… oh, Chandler, that feels so good… mmm… you can, um… caress her whole body and um… rub… um… breasts, her breasts… and clit… and… mmmm… you can, you can finger my pussy…”

It was clear what she was wanting. For the girl, it wasn’t just about having a dick in her butt.

It was about the total package of sensations.

Chandler gripped her pert breast, and gently massaged it as he continued fucking Monica’s ass.

“OOoo, yeah… rub my tits… rub ’em… mmm, yeah…”

He snaked his lower arm underneath her, and brought both hands up so he could run his fingers through her short hair. She slowly moved her head from side to side, like a pet relishing her master’s touch.

Then one arm wrapped around to her breast, as the other slid down between her legs. This whole time, the slow thrusts never ceased. In… and out… in… and out.

Monica was moaning loudly now. Chandler hoped that no one would enter the apartment and hear her. But in truth, he didn’t really care at that point.

He nuzzled the back of her head and softly kissed the nape of her neck.

His fingers gently rubbed Monica’s clitoris as his hard cock continued pleasuring her ass.

She was panting, “yes… yes… oh, Chandler… I love this… you’re doing everything right… don’t stop… keep going…”

Chandler’s other hand made its way to Monica’s crotch. She whimpered as he slid a finger into her pussy.

Monica’s lower body felt like it was on fire. Clit… pussy… ass… all three were sending tantalizing signals through her frame.

a****listic groans passed her lips.

Chandler held her petite body against his, as he pleasured her in every way he could think of. His lips brushed on her shoulder. They moved to the nape of her neck. He kissed her there. Hot breath created little goosebumps on her skin. He could sense that a small smile had formed on Monica’s lips.

Without removing his mouth, he opened it and gently pressed his teeth into the back of her neck, then closed his lips into a seductive kiss.

It was certainly not enough to be painful, but was very much enough to be quite erotic for them both.

Monica groaned a soft “Yes!”

He ran his tongue across her shoulder and back up to her neck. He gently bit, and gradually turned the soft nibble into a kiss. He sensually grazed her porcelain skin with his teeth, before covering it with soft wet kisses.

Monica couldn’t believe how good this felt, how good everything felt.

“You’re gonna make me cum, Chandler,” she moaned, “oh, you’re gonna make me cum. “

Chandler picked up the pace of his thrusts, making sure that his hips bumped against Monica’s ass each time.

“UUUuuhhhhn, yes… like that… do it like that…”

She was getting so close… so close.

“Oh, fuck my ass, Chandler. “

Never in a million years had he thought he’d hear those impassioned words from Monica.

But he was more than willing to comply.

“Oh, fuck,” she groaned, “oh fuck… oh, fuUUUUUGGHHHHNNNNN…”

Monica didn’t know if her orgasm started with her pussy, clit, or ass, for it rapidly spread through her entire body.

Chandler continued everything he was doing. Fucking her ass. Fingering her pussy. Rubbing her clit.


Monica held her head in both hands as she kept cumming and cumming.

Then the crest of the long wave passed and she started to come down.

“Uuuuhhnnn… mmmmm… uuuhhh… ooooo…. ohhhhh… ohh…”

Chandler slowed his motions with her, until they simply lay together, with his cock still in her.

“Omigod, Chandler. I can’t believe how incredible that was!”

“So is that zone, ‘number eight’? he smiled, referring to the previous lesson.

Monica laughed, “Well, for me it certainly is! And the way you do it, I’m sure it will be for Kathy too.

Chandler smiled and kissed her neck softly.

“Gee, Mon, thanks. But I think I had the best teacher in the whole wide world to help me. “

Monica gave a little laugh, still basking in her afterglow. Then she remembered her promise.

“Pull out of me, sweetie,” she said patting his thigh. Chandler did this. “On your back,” she directed.

Monica turned over and removed the condom from his rod, tossing it into the garbage beside the bed.

She knelt beside him on the bed, hunched over his body.

“I think you DEFINITELY earned your incentive reward,” she smiled.

Chandler smiled back, “My oral action?”

“Uh huh,” Monica answered as his cockhead disappeared within Monica’s lips. She moved her head up and down, gently sucking on his rod.

“Oh, Monica, that feels… Ohhhhh!”

She glanced to the side at him, and their eyes met.

Hers held a mischievous glint. Monica made little noises as she sucked him off, stroking his shaft.

Chandler was moaning at everything she did. He ran his hand through her hair and down her naked back. His hand slowly rubbed her tiny rear.

Monica pulled her lips off with a pop.

“Can you cum for me, Chandler? Are you close?” she purred, as she stroked his full length.

“Uh huh,” he moaned, with his head back and eyes closed.

Monica sucked the end of his cock as she continued masturbating him.

“Does it feel good?” she asked, pausing from her oral services. “Does it feel good when I suck on you?”

His groan answered her questions.

“I want it to feel so good for you, Chandler. I want you to cum while I rub you.

Monica’s hand gradually sped up as she closely cupped his balls in her other hand.

“Cum, Chandler… I want you to cum… I want you to cum on my face… and maybe even get some in my mouth…”

She took a quick suck on the head of his cock.

“Would you like that? Would you like me to taste your cum?”

Chandler’s body was tensing up, as his climax grew closer.

“Yeah, baby… just let it come… let it come…”

Another quick suck on his knob.

“Think about Kathy… think about how much she’s gonna enjoy it tonight… having your big… hard… cock up her ass… rubbing her body… fondling her pussy…”

Chandler tried thinking about his girlfriend, but hearing the way his friend was talking, only made him want Monica more.

“I’m getting closer, Mon… closer…”

She gently pulsed her grip on his balls.

By now, her stroking hand was working overtime, moving fast and hard, up and down.

“MMMmmm… so close,” he grunted through clenched teeth, his body arched in tension.

“Watch me,” Monica intoned, and Chandler obeyed.

Her face was hovering a few inches above Chandler’s upright dick. She opened her mouth wide, waiting for his cum. Seeing her like this was more than he could handle.

“AAAAAHHHHHH!!!” he groaned as he came, his body still rigid.

A large wad of cum hit her right below her eye. She moved her head slightly, and was able to catch the second shot in her mouth, closing her lips to savor it on her tongue. His cock kept cumming, spreading more jizz onto Monica’s lips and chin and nose.

Chandler collapsed back into the bed.

Monica massaged his cock and balls, coaxing out several more weak spurts.

A drop of cum fell from her cheek to join what was oozing down her hand. She slowed her jacking, and smeared his softening cock with the jizz.

“Oh, wow!” was all he could say.

Monica smiled, “I take it that you liked it. “

“Oh wow,” he repeated.

“Good,” she said, as she licked her lips, drawing in what her tongue could find. Then she grabbed the towel, wiped her face and hand, then his rod.

“Believe me, compared to the orgasm you gave me… I probably owe you two of these. “

“Okay,” he said. Monica giggled. Chandler went on, “I’ll take a raincheck. “

She laughed again. “All right, I’ll owe you one. “

“I’m afraid I’m going to need something in writing,” Chandler teased.

Monica gave him a look of good-natured suspicion. Then she went to her desk, pulled out a piece of flowered stationary, and scribbled something on it.

She folded it once and returned to the bed to give it to Chandler. He opened it.

At the top, in large letters was, “I. O. U. ” with words below it.

“This entitles Chandler Bing to one (1) blowjob/facial from Monica Geller. Good for one year from today’s date. “

It was dated and signed, “Monica”.

“Well, I won’t need a year to use this,” he smiled.

She flopped down next to him and cuddled in close.

“No, Chandler Bing, I bet you won’t. “.

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