Office Affair: Jill

Hank had been with the company a few years working with the same management staff when Jill was transferred. Jill was a hot shot out of another office and she was coming in to take over Hank's shipping department. When Jill was first introduced to the staff it was Hank's job to show her around being her most senior staff member.

"Hey," said Hank as he reached out to shake Jill's hand, "I'm Hank I'm going to show you around and introduce you to the staff."

"Thanks," said Jill, "I'm looking forward to get to know everyone better."

Hank took her down to the warehouse and introduced all of the guys and brought her through logistics and introduced her to the two girls he worked with most closely Mimi and Rachel.

"And this is your office," said Hank.

"Thanks," said Jill as she looked around, "I can't wait to work with you."

"You too," said Hank, "we're going to be working pretty closely together."

The next month went by as usual, Hank helped Jill pick up the slack as she got acclimated to the new office and she quickly made friends amongst the staff taking them out on her dime once a week. Jill always made an effort to stop by Hank's desk and talk about life and eventually they became very close. Jill would share stories about the men she went home with and Hank would tell her about whatever drama the women in his life were causing.

One day Jill came in wearing a purple top with a plunging neckline telling Hank it was for a date she had later. Hank had trouble taking his eyes away from her exposed skin but Jill didn't seem to notice as she said good morning and went to her office. He had never really thought about Jill like that before, she wasn't a knock out but she was cute, about his height and a little husky like him. She had long wavy brunette hair and sizable breasts. A moment later she paged him and told him to come into her office.

Hank entered the office and found her sitting at her desk with her hands folded in front of her.

"Close and lock the door," she said very seriously, "and take a seat."

Hank did as he was told.

"Is everything ok?" he asked.

"No," said Jill as she got to her feet and walked around her desk taking a seat on the edge of it.

"You're creating a hostile work environment," she said.

"I am?" said Hank taken aback by the accusation.

"Yes," said Jill as she leaned forward, her breasts practically spilling out of the top.

Hank tried to look away but struggled.

"See," said Jill, "that right there, how am I supposed to work when I know you're thinking about burying you face in my breasts."

"I'm sorry," said Hank, "it's just around here."

"Are you a virgin?" asked Jill.

"What?" asked Hank confused as she leaned in closer.

"Have you put your erect dick in a girl's pussy until you came?" she asked sternly, her breasts still on display in front of him.

"Um, well no but," Hank stammered.

"That's what I thought," said Jill as she sat up with a smile.

"Have you eaten pussy?" She asked a little bit calmer.

"Yea," said Hank still in disbelief that they were having this conversation.

"I'm fucking with you Hank," said Jill with a chuckle.

"What?"

"I was trying to see if this top was eye catching," she said running her fingers over her breasts, "turns out it is."

"Oh," said Hank as he breathed a sigh of relief, "Yes it's extremely eye catching."

"But you're really a virgin?" she asked with a seductive smile.

"Yea," he said a little ashamed.

"Aww," she said as she walked back around her desk and took a seat, "you just need to find a good girl."

Hank breathed a sigh of relief and stood up turning toward the door.

"I didn't say you could go," she snapped.

Hank froze in his tracks and turned back towards her. Jill motioned with one finger to come closer and Hank walked around the desk next to Jill. Jill swiveled her chair so she was facing him and reached up to grab Hank's shoulder and pushed him down onto his knees.

She hiked up the skirt she was wearing and spread her legs revealing her wet pussy. Jill reach up and put her hand on the back of his head.

"Get in there," she said with a smile as she pulled his face down between her legs.

Hank's nose was pushed into Jill's bush, and he ran his tongue up her pussy. Jill reached over and dialed the phone putting it on speaker as she dialed.

"Welcome to the weekly conference call," said the man on the phone.

"It's Jill from the Yonkers office," she said.

"Hey Jill," said the man as Hank licked small circles around her clit, "how are you liking it there?"

"Oh its ok," she said, "my team is just getting into a rhythm."

"That's great," said the man, "now to our topic for this week."

Hank tuned out the man as he grasped Jill's thighs and started to push his tongue into her pussy quickly as she closed her eyes, biting her lip as she leaned over and muted her line. Hank brought his mouth up to her clit and sucked on it for a bit before licking it quickly. Jill leaned her head back and let out a soft moan grasping the arms of her chair as Hank continued licking her wet pussy. Hank slid two of his fingers up into Jill who gasped as the man on the phone droned on.

"Jill," said the man, "Jill?"

"Yes," she stammered as she slammed the mute button.

"Everything ok?" he asked.

"Mhmm," she muttered, "Just getting laid into by a client."

"Well your numbers are good," he said, "keep up the good work."

"Thank you," she practically whispered.

"All right I think we'll call it at that," said the man as Hank finger fucked Jill and licked her as quickly as he could.

"Have a good week," said the man.

"Bye," squealed Jill as she slammed the phone down onto the receiver as she let out a series of loud moans.

Jill pushed Hank off of her and caught her breath for a moment.

"Stand up," she said her eyes still closed, "are you hard?"

"Yes," said Hank looking down at her milky white breasts pushing against the restraint of her top.

"Let me see your dick," she said pulling her top open so her breasts spilled out.

Hank undid his pants and Jill reached over taking his hard dick out.

"Anyone ever told you that you have a big dick?" asked Jill.

"No," said Hank as Jill started to stroke him.

Jill took him in her mouth and gagged a bit when she had him almost all the way in. She grabbed Hank's hands and put them on her breasts. Hanks squeezed her large breasts as she grasped his waist and started to bob her head back and forth on his dick each time trying to take him as far into her mouth as she could. Jill took him out of her mouth and stroked him with both hands as she looked up at him.

"Don't cum in my mouth," said Jill.

"Ok," stammered Hank.

"Do Not Cum In My Mouth," said Jill, "If you ever want to see these titties again. If you want to shove this into my pussy."

"Yes," said Hank, "I won't".

Jill took him back in her mouth again and bobbed back and forth until she finally took him all the way in her mouth and held it there for a while before taking his saliva soaked dick out of her mouth.

"You ready to cum on these tits?" she asked stroking Hank.

"Yes," he moaned.

Jill squeezed her breasts together presenting a large target for Hank as he started to stroke himself furiously.

"Do it," she said and Hank did busting all over her breasts.

Jill stroked Hank through every last drop before letting go of him and reaching for some tissues to clean herself off with.

"I suppose I don't have to tell you not to tell the others about this?" she said as she put her breasts away.

"I won't tell," said Hank.

"Good," said Jill, "now get back to work."

Hank zipped himself up and went back to his desk. Where Mimi was waiting.

"Hey," she said, "I need signatures for these."

Hank took the papers from her and started to sign them one by one.

"Everything ok with boss lady?" asked Mimi,

"she had you in there for a while."

"Yea she wanted me in on her call with corporate," he said handing her back the documents.

"Are we all getting fired?" she asked leaning on the edge of his desk.

"No," he said, "they said our numbers are good and to keep up the good work."

"Oh good," said Mimi, "I hate looking for a job."

Mimi left Hank's desk and he breathed a sigh of relief taking a moment to absorb what had happened in Jill's office before turning his mind back to work.

As Mimi and Rachel left Hank shut down his computer and got ready to leave. He went to Jill's office to tell her he was leaving for the day. He opened the door to find Jill waiting just on the other side.

"Heading out?" she asked.

"Yea," said Hank making every effort not to look at her breasts.

"I'll walk out with you," she said shutting the lights before following him out.

Hank and Jill walked out of the building and Hank turned to lock the door. The two then walked to their cars.

"What a gentleman," said Jill, "making sure I get to my car."

"Your welcome," said Hank, "Have fun on your date tonight."

"You're so naïve," said Jill, "You think I would have pulled you into my office today if I had a date tonight? I'm not a slut."

"Oh, no I didn't mean," stammered Hank.

"You're so much fun to toy with," said Jill with a smile, "why don't we go out then? I'm all dressed up and ready to go."

Hank followed Jill to a nearby restaurant and they walked in together. The couple was seated in the mostly empty Italian restaurant and Jill ordered a bottle of wine for them.

"So," said Jill taking a sip of her wine, "did you enjoy our little office tryst?'

"Yea," said Hank with a grin, "but it was a little unexpected."

"I find surprise makes it even sexier," said Jill.

"So you had this all planned," said Hank.

"Mhmm," she says through another sip, "that's what makes me management material, I know how to get what I want."

"That you do," said Hank, as he finally took a sip of his, "so I assume you still want something."

"I do," she said finishing her glass and allowing Hank to refill it, "I've never taken someone's virginity before. Don't worry, I'm not expecting to have my world rocked your first time."

Hank nervously drained his glass.

"Oh take it easy," said Jill, "I'll be gentle."

Hank and Jill ate as she teased him throughout. Once the bill was paid Hank walked Jill to her car before following her to her apartment. When they got to the door Hank grabbed Jill and pulled her in for a long kiss.

"That's the spirit," said Jill, "now save some for inside."

Jill unlocked the door and turned on the lights in her living room before leading Hank to her bedroom.

"This is where the magic happens," she says turning on the lights.

Jill turns to Hank and pulls him in for another long kiss before pulling down her blouse freeing her large breasts to Hank who grasps her breasts and buries his face in them. Hank squeezes her breasts which spill out of his hands and Jill smiles.

"Go to town on them," she coos, "I love it when I guy gets his hands on them for the first time."

Hank does as he's told alternating between her nipples sucking on them and licking them.

"Now now," says Jill as she finally pulls him off of her before pulling her blouse up over her head and undoing her bra.

Jill pulls Hank's shirt up over his head and undoes his pants. She smiles as him as she slowly slides her pants and panties off standing naked in front of him. She has long wavy brunette hair that comes down past her shoulders, large breasts that Hank guessed were at least D cups and wide hips, and she was husky like Hank.

"There are condoms in that drawer," she said motioning to one of the nightstands near her queen-sized bed.

Hank opened the drawer and found it full to the brim with condoms, he pulled one out of the pile and slipped it on. Jill sat on the edge of her bed and motioned with her finger for Hank to come closer. Once he was close enough she pushed him to his knees and pulled his face in between her legs again.

"Get me ready for your cock," she says.

Hank licks her like he had earlier in the day and slides two of his fingers into Jill who moans and lays back on the bed. Hank reaches up with his free hand and squeezes one of her breasts. She reaches down and grabs the back of his head holding it tight against her pussy as he licks it while still quickly fingering her.

"I'm ready," she moans, "I want your cock, I need it."

Hank gets to his feet and positioned himself so his tip is pressed against Jill's wet pussy.

"Go slowly," she says.

Hank slowly presses his tip into Jill who moans and rubs her clit. He continues and pushes himself halfway in as Jill lets out another moan.

"All the way," she says, "fill me up."

Hank slides himself all the way in, Jill's pussy tight around his cock and slowly pulls out before thrusting himself all the way back in. Jill starts to rub her pussy furiously.

"Harder," she moans.

Hank slams himself into her and Jill squeals, he does it again, and again to moans and squeals.

"I'm close," she pleads, "don't cum."

Hank struggles to hold back, his pace quickening. He reached down with both hands and squeezed Jill's breasts. Jill shivered in response and her moans sent Hank over the edge as he busted.

"Not bad," said Jill with a smile, "go clean yourself up," she says pointing to the bathroom.

Hank does as he's told and finds Jill laying on the bed waiting for him. He climbs into the bed and cuddles up with Jill who kisses him.

"You can stay the night," she says.

The two drifted off to sleep in a little while.

Hank awoke in the morning and found Jill climbing out of bed.

"Hey," she said seeing him awake.

Hank sat up and threw the blankets off as he went to climb out of the bed. Jill caught sight of his morning wood and came back to the bed.

"For me," she said giving it a few strokes.

Jill reached to the nightstand procuring a condom which she slides onto Hank. Jill leans over the bed, her breasts resting on the sheets as Hank comes up behind her and presses himself slowly into her. Jill moans and grasps the sheets as Hank pushes himself the rest of the way in. Hank grasps her hips and thrusts himself forcefully into her followed by a few hard thrusts which are mean by moans from Jill.

"Yes," she moans in response to his hard thrusts, "just like that."

Hank continues to give Jill what she wants enjoying the moans she's letting out with every thrust and reaches around grasping her breasts.

He decides to go faster while still pushing himself in as far as he can.

"Oh my fucking God!" she screams as she orgasms.

Hank doesn't slow down even as Jill's juices run down her thighs. Jill reaches back and grabs Hank's waist stopping his thrusts. Jill rolls onto her back and grabs Hank's cock pulling the condom off.

"Fuck my titties," she moans.

Hank climbs on top of her and positions himself between her breasts. Jill pressed her breasts together almost covering the length of Hank's dick before her began humping them.

"Big tits for a big cock," she says looking up at Hank who is getting close.

Hank gives a few more thrusts before busting, his strings of cum hitting her neck and cheeks.

Hank and Jill continued their workplace affair in the coming weeks, at first they were cautious but then their romance spilled over into every corner of the office. Then the word came that she was getting transferred again.

Jill called Hank into her office for the last time after everyone had left for the day.

"So," says Jill as Hank takes a seat, "I guess this is the end of our affair."

"Does it have to be?" asked Hank.

"Yes," she said, "I mean this was only ever sex to me. And there is good news, you're to be my replacement."

"I mean I'm glad for the promotion," said Hank, "but is that all this was?"

"I'm sorry," said Jill, "but yes."

Hank got to his feet and walked around to Jill's side of the desk as she rose to her feet.

"Then one last time," said Hank, "take off your shirt."

Jill starts to unbutton her shirt as quickly as she can. Once it is open Hank undoes the front clasp on her bra letting her breasts spill out. He bends her over the desk, her breasts pressed against the wood before Hank grabs her skirt and pulls it and her panties down over her ass. Hank gets to his knees and presses his face to her pussy running his tongue along it. She was already getting wet and Hank only gave her a few quick licks before getting to his feet and undoing his pants.

Hank grabs Jill's waist and thrusts himself into her relishing the feeling of her pussy, this being his first time inside her without a condom on. Hank got into the rhythm of hard thrusts he knew she loved pushing her close to orgasm. As Jill began to cum Hank reached up and grabbed a handful of her hair giving it a tug as he fucked her to her climax. Hank stopped waiting for her to catch her breath and let go of her hair as she melted against the desk.

Hank took a seat and Jill finally stood up and sat on his lap with her back to him before sliding down onto him. He reached up and grabbed both of her breasts as she started to grind on his cock. Hank lets grind for a while before grabbing her waist and beginning to hump her quickly. Jill grasps the arms of the chair as Hank reaches down with one hand to rub her clit. Jill rides him to orgasm before finally pulling his hand off of her and collapsing back onto him. Jill climbs down onto her knees and takes Hank into her mouth. She begins to bob her head up and down on him while stroking him with one hand.

"Jill," stammers Hank as he approaches orgasm.

Jill disregards him and continue to stroke him holding her lips around him tip until he cums into her mouth.