Friends: A Little Office Sex

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Rachel finds Chandler handcuffed in her boss' office.
3.6k words
4.52
165.1k
39

Part 2 of the 36 part series

Updated 08/30/2017
Created 10/10/2004
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Dudeman85
Dudeman85
294 Followers

Chandler had been fooling around with Rachel's boss, Joanna, in her office. When she was called away to a meeting, she teasingly locked him to her desk chair, sans pants, to wait for her return. Unfortunately for him, she called later to tell him that she would be delayed for quite a while.

Thinking they were going to sneak a peek at the Christmas bonus list, Rachel and Sophie used a hidden spare key to get into the office, and found Chandler in this compromising position. They left, with Sophie freaked out and Rachel mad. Despite Rachel's anger with him, Chandler convinced her to unlock the handcuffs and let him leave.

But no sooner had she done so, than she realized that Joanna would come back, find Chandler gone, and know that Rachel was involved. In the frantic rush of activity, Chandler became handcuffed to the filing cabinet beside the door.

"Chandler! Chandler, please, I have to get you locked up back the way you were, I am sooo gonna lose my job, she's very private about her office. Now I know why," Rachel pleaded.

"Hey, look, you're in trouble either way! Okay? If she comes back and sees me locked to this instead of the chair, she's gonna know you were in here. So you might as well just let me go," Chandler knew that he had Rachel in a no-win situation.

"What if I clean your bathroom for a month?" she suggested.

"It still wouldn't be clean," he replied, eliciting a look of disgust from Rachel. "All I want is my freedom."

"Foot rubs for a month!" she offered.

"Freedom!" he insisted.

"I'll take all of your photos and put them into photo albums!"

"Freedom! I want my freedom! Why won't you hear me?!" Chandler opened the door and called to Rachel's coworker, "Sophie, help me! Help me!!" Sophie stood up to help.

"Sophie, sit!!" Rachel ordered. Like a little dog, Sophie obeyed.

Rachel quickly closed the door and stuffed Chandler's tie in his mouth, as a gag.

"No! Would you just calm down!" she said to Chandler, her own calmness completely gone.

Chandler tried to scream a little bit, then realized that he could simply spit out his gag. It left his mouth with a 'pouf'.

"I'm gonna say this for the last time," Chandler began with measured tones. "Would you please just…"

As he was speaking, he moved his arm and the upper file drawer rolled out. It hit him in the back of the head, enhancing his irritation with Rachel. Undeterred, she continued the negotiations.

"I uh... will buy and wrap all of your Christmas gifts."

"No!"

"I, ah… Oh! I'll squeeze you fresh orange juice every morning!"

"With extra pulp?" he asked, with false brightness.

"Yeah!!" Rachel said happily, thinking she'd finally found a deal.

"No!"

"D'oh!!" she exclaimed, frustrated. She paused, then a little smile crept across her face. "I've got it!"

"You don't have it," he said suspiciously.

"I have so got it." She cleared her throat. "Well, you said that Joanna would be gone for a couple of hours." She moved in close to him. "So, I'm thinking... a little touchy... a little licky... a little sucky..."

Rachel's eyes matched the seductive tone of her voice. Her tight body was invitingly close.

"Well, oral IS good..." Chandler said, with feigned contemplation. "But won't Sophie wonder why you're in here for so long?"

"No, she's really not that smart..." she said matter-of-factly.

"Oh. Okay. In that case, I'm thinking of something... that rhymes with oral..."

Rachel thought for a moment. Then she took a quick step back.

"NO! No deal!" she said, pointing her finger at him.

"Oh, come on. What's the big deal?"

"Look, I didn't even let Ross do that when we were dating... and I was in love with him. There's no way I'm gonna let you put YOUR thing..."

"All right, all right... calm down. How about just some good old fashioned sex on the desk?"

Rachel looked at him with suspicion.

"Okay, but only if I get some oral too. I need to get something out of this, too, ya know. Deal?"

She extended her hand, except instead of offering to shake his, she did a more appropriate thing, and placed it on his crotch. Chandler looked down.

"Deal!" he said putting his free hand on her breast. They each gently squeezed their handful.

"Now, unlock me."

Rachel retrieved the key from her pocket.

"So can I pretend that you're my secretary? 'Miss Green, can you come in her and take some DICK-tation?'"

He laughed, but received only a testy look from Rachel.

"Look. Don't push it," she warned.

Rachel reached up to unlock the handcuffs that held him to the filing cabinet. But she paused, and looked at him with a nasty smile.

"Hmmm... you can't really move until I unlock you..."

"Yes, that's kind of how handcuffs are designed to work," Chandler snapped back. Rachel was undaunted.

"Well, what if I'm not ready to unlock you?"

She slid the key in her pocket and pushed down the front of Chandler's boxers.

"What if I want to do some stuff to you while you're cuffed to that filing cabinet?"

She began to stroke his now-hard rod. She could tell that he liked her idea, even if he could only stammer a response.

"I'm beginning to see why Joanna wanted to have you as a boy-toy. Except as MY boy-toy, I'm going to treat you real nice," she moved in and kissed him with her last words.

Rachel squatted in front of Chandler, slowly stroking his rod, and looking up at him.

"I think I want to play with my toy... a little touchy..." she whispered, "a little licky..." She licked the length of his cock.

"A little sucky..." She placed her mouth over his head and gently suckled on the end.

"A little more sucky..." she purred. The head went back in, and she sucked long and hard.

"AAAWWWWWWW!" Chandler groaned.

"SHHH!" Rachel shushed him, "Sophie's still at her desk. We can't let her hear us. She's dense, but she's not deaf."

"Okay, I'm sorry, I'm sorry," he whispered back, " but it's really hard not to..."

"Well do I have to stop?"

"No no, let's not get hasty. I'll be quiet. I promise."

"Okay," she smiled seductively, "because I want to keep sucking on my toy."

Rachel was jacking his dick as she held the front of his underwear down.

"Y'know, these are just in the way. I don't think I want them on you anymore," she decided.

With that, she pulled down Chandler's boxers and gently slapped his feet to get him to step out of them. Her hands glided back up. She slowly stroked his rod and fondled his balls.

"There. Isn't that much better? Just think of it as a different kind of freedom," she said as she put Chandler back in her mouth.

Rachel held his thighs as she rocked her body back and forth, sliding her lips up and down his shaft. Chandler watched his beautiful friend sucking his cock, and tried for all he was worth not to make a sound.

Her movements gradually transferred from her whole body to just her head, allowing a faster blowjob as it moved back and forth. Chandler rested his head on the file drawer behind him, breathing hard.

Rachel's mouth left his cock, and her hand took over, stroking him in time with her previous sucking.

"Does my boy like the way I suck his toy?"

Her lips were instantly on his sack, sucking on one of his balls.

"Oh yeah!" he said in a low tone.

"Good, because I wouldn't want him to re-neg on our deal," she said, then slowly licked the bottom of his shaft as she watched him.

"Oh, I won't," he promised.

With one last series of licks and sucks, Rachel stood, and moved in close to him.

"You actually thought I might let you do me in the ass, huh? So, do you like my ass, Chandler?" she teased.

"Oh yes, it's very very nice," he said nervously.

Rachel was wearing a dark grey pantsuit. She turned around and pulled the jacket up to reveal her butt. It filled the cut of her pants nicely; tight enough to be a little provocative, yet still very professional for the office.

"I think I have a nice ass, too. I work very hard at it, you know..."

She backed into his hard rod, and rubbed the shaft with her butt cheeks.

"... making sure that it's firm... and tight... and sexy... I want guys to want to fuck it... but you know that they can't..."

A small drop of precum beaded out onto the fabric.

"Uh, Rach... if you keep that up... I'm probably going to blow my load all over your suit."

She laughed sexily and turned around.

"Well, we can't have that, now can we," she said as she reached up and unlocked the handcuff from the drawer handle. "Why don't you go sit in Joanna's chair."

Chandler went and sat down. Rachel strolled around the end of the desk and came up behind him. She ran her fingers through his hair, then teasingly jerked his head back so he was looking up at her. She leaned over and kissed his mouth, upside down. A long wet kiss.

"Time for your part of the bargain."

Rachel spun him around to face her. She undid the single button on her jacket, and allowed it to fall open. Removing it, Rachel tossed it across the desk. She was wearing a white long-sleeve shirt under it. Rachel looked at Chandler sitting there in only a blue dress shirt.

"I don't think you should leave that unattended," she smiled.

Chandler caught her meaning and gladly stroked his rod as he watched his sexy friend strip.

Rachel unzipped her slacks, stepped out of them, and draped them over her jacket. Beneath her v-neck top, her obviously erect nipples told Chandler that her only underwear was the lacy yellow thong that hung loosely in front of her trimmed snatch of hair. It was held on only by simple strings as straps. She stepped toward him.

"Take this off me."

Chandler gently pulled on the front and saw the pussy hair that was veiled by the lace. His hands eased her thong down her thighs, and it fell the rest of the way to her ankles. Rachel lifted her high heels, one by one, to step out of it.

His hand traveled upward, and he brushed his fingers across her pussy. She was already quite wet. Rachel read his mind.

"Giving head always gets me VERY horny," she explained.

Chandler slowly rubbed her pussy lips as Rachel ran her fingers through his hair.

"Mmmm, yeah," she said softly.

His other hand moved up and under her shirt, and groped her breast.

"Oh, yeah," Rachel moaned, brushing her long hair from her face. "Oh, Chandler, sweetie, I like this and all... but I REALLY need you to lick me."

"Well, that was part of the deal..." he agreed, trying to hide his excitement.

Rachel moved between Chandler and the desk. She leaned back against it, giving him the slightest peek at her pussy. He leaned in and gave her a little lick. She gasped at the tingling in her clit.

"You need to be up on the desk," he suggested.

She hopped up on her boss' desk and put her high heels up on the arms of the chair. Chandler sat between them, and had a wonderful view of her slim thighs, shaved pussy, and little clit. He ran his hand up her leg, caressing it from ankle to puss.

Chandler rolled the chair toward her, bringing her feet much closer to her butt. He placed the flat of his tongue against Rachel's pussy and slowly licked it. Rachel let out a little moan.

"Remember... no noise," he whispered.

Rachel replied, a bit annoyed, though not at him, "I know... I know!"

Chandler enjoyed the tables being turned, and he resolved to make it good. He traced the outside of Rachel's labia with his tongue. He wanted to tease her. Make her want more than she was getting.

He flicked the tip of this tongue gently across her clit, barely brushing it. He softly blew cold air onto it, making her shiver.

"Oh god, you're killing me," she whispered in frustration. "Just lick me, dammit."

Chandler smiled at her. She returned a glare of irritation, mixed with desire, though she tried to hide a little grin.

He leaned in and placed his whole mouth over her pussy and licked her lips up and down.

"Oh yeah... that's it," she moaned, finally getting some relief. "Just like that... oh... yeah, lick it good."

She squeezed her breast, then realizing that it wasn't enough, she slid her hand under her shirt and rubbed her nipple.

Chandler's tongue weaved in and out of her folds, as though it were searching for something. Licking and licking and licking. Persistently taking Rachel higher.

"Yes," she whispered, "oh Chandler, yes... lick it... lick it..."

She put her hands behind her, resting them on the desk, and rotated her hips up, so he could service her more completely.

Chandler's tongue probed deeper and deeper into Rachel. She was whimpering with each new feeling. It was as if her flesh knew exactly where his tongue would go next, and began tingling a moment before it received its wet touch.

Rachel was trying very hard to keep her sounds quiet. But it was so difficult for her with what she was feeling between her legs.

"Ahhh... ahhh... ahhh...ahhh..." she whined, softly.

She felt Chandler's tongue move up to her clit, his lips close around it, and then the most amazing jolt as it was given a good, long suck. Her lips were firmly closed, trying to hold in the moans that longed to escape.

"Mmmmm... mmmmm... mmmmm..."

Then she whispered, "Chandler, I can't take much more. I need you to go in me... please."

Chandler left her pussy with a gentle kiss, then helped bring her legs down to the ground.

"Turn around," he suggested.

Rachel had given up the whole 'boy-toy' game, and simply wanted him in her. She followed his lead.

"Bend over the desk," he whispered as he gently pushed her onto the surface.

Chandler looked down at Rachel. Long light brown hair. Slim, athletic body. Gorgeous round ass. Her feet were just over a shoulder width apart. Rachel was in the perfect fucking position. For just pure sex, Chandler liked this best.

Rachel's cheek rested on the glossy wood and her eyes were closed, as she waited for the sensation that she knew would come. There was the first of it; a soft cockhead rubbing on her wet pussy.

"More, more," she thought.

Then pressure began to build at the entrance to her cunt.

"Yes," she mouthed.

Rachel could feel her pussy lips slowly parting as Chandler tantalizingly started to fill her.

"More, more," this time, whispering.

Little by little, in a teasingly slow fashion, Rachel felt herself being filled with a warm hard cock. She groaned as loudly as she dared.

Chandler began drawing his dick out of Rachel, then he pushed it back in. Drawing and pushing, over and over. Rachel dwelt on every increment of motion inside her.

"OH!" she whimpered quietly, "oh, yes... please..."

Chandler looked around the room as he fucked Rachel. Office furnishings... filing cabinets... professional-looking decorations.

"Hell, if Rachel worked for me..." he thought.

Then his mind went to his own office...

Rachel bent over his desk. Fucking him for her raise.

"Well, Rachel, you've learned some excellent skills this year. And you'll get an extra 5% if you let me do you in the ass, tomorrow. So, what should I tell payroll, Miss Green?"

Another scene entered his mind...

Rachel walking in, wearing a business suit with a short skirt and high heels. He was looking at her shapely legs. Running his hand up her thigh to her stocking-top.

"Time for your daily blowjob, Mr. Bing," she'd say.

Then she would dutifully drop to her knees and blow him until he came in her mouth.

Suddenly, in his mind, he was behind the counter at Central Perk. The place was full of customers. Joey, Phoebe, and Monica sitting on the couch. Ross in the big chair.

No one even aware that Rachel was crouched behind the counter with his cock in her mouth. She was wearing one of the cute outfits from her waitress days. Little apron. Short skirt. Black hose. Sleeveless denim shirt. Hair up. Just sucking away.

"Say, Monica," he'd call across the room, "You're a chef. Could you come here a minute? Rachel needs your help with a taste-test."

Monica would walk across the room and disappear behind the counter, as everyone went about their business...

Chandler caressed Rachel's ass and ran his hand under her shirt to rub her back. She felt the cold steel of the handcuff, still around his wrist, dragging up and down her skin.

"Fuck me, my boy-toy," she thought, indulging again in her fantasy.

She imagined Chandler handcuffed to their radiator, naked. She'd come home and kiss him passionately. Just the kiss would get him hard. She'd lift her skirt and pull his face to her pussy. He'd gratefully lap away, driving her to an orgasm that would wash away the day's stress.

Sometimes she would let Monica play with her little boy-toy. In her mind, her roomie was sliding up and down on Chandler's dick as he sat, leaning against the wall.

Rachel would walk over, caress Monica's body, then put her breast in her dark-haired roommate's mouth. Monica would suck Rachel's tit, while Chandler fingered her pussy.

After Monica was done with him, Rachel would take her place on Chandler. Monica would lick her nipple and rub her clit, as she rode him...

Neither realized that they were making far more noise than intended.

Suddenly they both snapped back to reality. Their faces turned up, and they froze, staring at the door as it opened.

"Rachel, is everything all r-"

Sophie's look was even more panicked than theirs. In one glance, she took in the sight of men's pants on the back of a chair, Rachel's pantsuit draped over Joanna's desk, and her coworker bent over her boss' desk with her friend laying across her back.

"Yes, yes, everything's fine. Bye-bye, now," Chandler said, rushed.

"Sophie, I can explain everything," Rachel said without moving. "Just... just let us finish and I'll be right out."

Sophie only nodded, the frightened look never leaving her face as she closed the door behind her.

"Well, so much for being quiet," Chandler said.

"Oh thank god," Rachel sighed, relieved. "Now fuck me."

Chandler resumed his thrusts, and immediately realized that Rachel had given up on holding back her moans.

"Ohhhh yeah... oh Chandler... yeah... do it... do it..."

Rachel felt the weight of his body pushing her into the table. So erotic to her.

"Deeper... go deeper," she panted.

He stood, and wrapped his fingers around her waist slightly pulling her to himself as he reached the bottom of each thrust.

"AAWWWHHH..." she moaned, feeling his head press against the top of her vagina. "Now harder... fuck me harder."

Chandler slowly withdrew his rod, then rammed it into her.

"FUCK, yes," she screamed.

He did this again and again, feeling her ass slap against his stomach, each time.

Rachel was tightly gripping the curved front edge of the desk with her outstretched hands. Her beautiful face contorted in pleasure. She groaned through clenched teeth.

"Fuck me, Chandler... nail me good and hard... UHN... UHN... now faster... UHN... bang me faster, boy-TOY!"

Chandler was completely aroused by hearing his friend talk like this. He was determined to make her cum. He pounded her as hard and deep and fast as he could.

"UHnnUHNnnUHNnnUHnnUHNnUHNnn..." Rachel gave out a long groan, punctuated by his thrusts.

Chandler's face was flushed and his breathing sounded like an old steam train. He was so close, but he was holding back as long as he could, hoping that Rachel would cum first.

Soon, her body surrendered to her orgasm.

"AAAAAAHHHHHHH!!!!" she screamed. Then she felt hot cum shooting into her. "OHHHHhhh... ohhhhh... mmmmm... yeah... yeahhh... cum... in me... cum..."

Chandler's thrusting abated as they both felt the climax ease away.

A few minutes later, with Chandler re-secured to the chair, Rachel walked out of Joanna's office. Sophie's back was to the door, and she discretely pulled her hand out from under her skirt.

As Rachel tossed a bundle of soiled Kleenex in the wastebasket, she said, "Um, look, Sophie... about what you saw before..." she laughed nervously as she went on, "and I guess what you heard..."

Dudeman85
Dudeman85
294 Followers
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