Jeff’s Office Adventure Ch. 02

Chapter 2 -- Jeff pursues his secretary after being encouraged by his wife.

Jeff got a sleepy kiss goodbye the next morning and Leanne's last words to him were "Good luck with Cindy. If you don't take control of her someone else will. Tell me how it goes."

His head was spinning as he drove to work. When he drifted off to sleep the night before he assumed their conversation was accidental dirty talk, a sex fantasy cranking them both up to a rare second round of orgasms. His wife's parting words implied she expected him to follow through.

At work, Cindy greeted him from her desk with her usual smile. "Morning Jeff."

"Good morning Cindy. You look nice again today." She did look nice, in a tight skirt just above the knee and a white blouse.

Cindy stood up a little too quickly, and Jeff watched as her full breasts strained to catch up with the rest of her and bounce slightly. Jeff wondered if she caused the bounce on purpose and realized he was still looking at the front of her blouse. She beamed at him brighter as he walked past her into his office. She followed, "Your morning is busy, I've put a few files on your desk to review before you make the calls."

"Thanks, Cindy."

"The afternoon is lighter, we'll have time to catch our breath after lunch."

"OK, perfect. I'll get started in a minute."

Cindy was right, the morning was busy and they barely had time to chat. Every time she came into Jeff's office to collect files or drop others off, he would look up and be reminded of what his wife suggested. As if that wasn't enough, partway through the morning Leanne texted him: "Any luck?"

Jeff had been losing resolve all morning. Leanne's text confirmed she wanted him to follow through, it wasn't just a dream and his resolve firmed. He texted back: "Nothing yet!"

After lunch, it did slow down. Midway through the afternoon Cindy came into the office and closed the door behind her. Jeff's office was in a quiet corner of the building, but people occasionally walk by to say hi. A closed door, however, meant sensitive conversations and no one ever interrupted. Jeff's mouth grew dry as he knew it was probably 'showtime'. He'd been thinking about what Leanne told him to do since she texted him, he wondered if he would get the chance. He recognized the chance was walking up to his desk now.

"Here are the contracts for your signature before we send them out," Cindy said.

He noticed she had freshened her make-up and, as usual, an extra button on her blouse was undone. She stood on the opposite side of the desk and bent over low as she carefully placed the folders in front of him. Jeff let his eyes drop from her face to the open top of her blouse. He forced himself to let his gaze linger, taking in the shape of her hanging breasts held up in a lacy, pale blue bra. Normally he would steal a furtive glance before lowering his eyes to his desk. Plenty of her full breasts were visible above the bra and he wondered if they might spill completely out into his view.

Jeff took a deep breath, "What a pretty blue bra you're wearing." His wife told him to say that. According to her, Cindy would now either hide, or not.

"Thanks! It's one of my favourites. It's comfortable but I feel sexy in it, too."

Jeff exhaled slowly as he signed contracts. His wife was right. He looked up, directly into her blouse, at the tops of her breasts and she shifted her weight to allow her blouse to gape open even more. He could see the shadow of her dark nipples through the lace and how they were standing up under his gaze. He could tell Cindy's breasts were larger than his wife's, almost too large for her frame. He could see all the way down to where her blouse was tucked into her skirt, including her cute belly button stretched taught by her core as she held her position bent over the desk for him. He risked a quick glance up to her face and she was looking directly at him, smiling.

"I can see why," Jeff replied, "your breasts look fantastic."

"The lace is soft and comfortable, have a feel." Cindy stretched forward a little more.

Jeff put down his pen and reached into her blouse with his right hand. He tentatively traced his fingertips around the scalloped lace edge of her bra, next to her areola. It was soft and inviting, both her skin and the lace. He ran his fingers over the lace cup around to the underside of her bra and cupped her breast. Her nipple had firmed even more. He gently touched her areola through the lace and ran his thumb all around her nipple. Cindy's eyes were closed now and he watched her face as he stroked her firm nipple directly with his thumb. Her mouth opened slightly and he could see the tip of her tongue.

"Does the other one feel as nice?" He asked.

"I think so. You should check," she said softly.

Jeff used the same hand but switched breasts and gave it the same treatment. As he finished Cindy seemed to be pressing her breast towards his hand to feel a firmer touch, but after a final, firm stroke directly over her erect nipple, he withdrew his hand.

"Yes, the other one is just as lovely," Jeff said. "I might have to check again later."

"Anytime you want."

Cindy gathered the folders off his desk, making no attempt to hide her breasts from Jeff's view. When she stood up, she held the files low and arched her back, stretching out her blouse with the tits Jeff had just been fondling. Her firm nipples were clearly visible, tenting through her blouse before she turned to walk out of his office.

Moments later Jeff was alone in his office and feeling a little dazed. He wasn't sure how far he could push this new side of Cindy but he was determined to push a little. Based on how Leanne talked to him in bed the previous evening she would be disappointed if he came home and all he'd done was fondle Cindy's tits.

After another work phone call, Jeff called out his office door "Cindy, could you come here for a minute, please."

Cindy came in the door with a pad of paper and a pen, but before she could come too far Jeff spoke again.

"Please close the door and take off your blouse for me."

Jeff was nervous making this request. Maybe the earlier activity was some sort of one-off and she would be horrified and a sexual harassment suit would occur. Maybe he completely misunderstood.

Cindy smiled and turned to close the door. She put her pen and pad down on a console near the door and reached up to her buttons while still turned.

"Turn around Cindy, I want to watch."

"Of course."

Cindy turned. She had already undone two buttons and continued down the front of her blouse. Her cheeks were pink and she looked a little embarrassed, but she pulled the tails of the blouse from her skirt and undid the last button before opening it up to display her firm tits, held up by the lacy light blue bra. They jiggled in a pleasing way as she shrugged the blouse off her shoulders and let it slide off her arms. She turned and hung it on a coat rack by the door before picking up the pad and pen and proceeding to his desk.

She stood off the corner of his desk making no attempt to cover her partial nakedness.

"How do you want me?" She asked confidently.

"Come sit here," Jeff said and pushed his chair away from the desk and patted his lap. "I just want to dictate some notes from the phone call I was just on."

Cindy walked around the desk and perched comfortably on his lap, sitting sideways across his legs. She smiled and re-adjusted to tuck his erection between her legs.

He put one hand on her back, and one on her bare tummy as he began to dictate the notes from his phone call. Cindy dutifully wrote on the pad even as Jeff began to move his hands around her bare skin, on her front and back at the same time. He wasn't tentative this time, or even too gentle. Cindy held her arms well out in front of herself and Jeff freely ran his palms up and down, cupping her breasts, touching her neck both front and back. He touched her shoulders, but didn't want to affect her ability to continue taking notes. As he was finishing with his dictation, he held her sides and guided her torso slightly so her back turned toward him. Jeff undid her bra, pulling the straps apart and pushing them over her shoulders. Cindy turned back and calmly pulled each arm out of the straps swapping her pen and pad from hand to hand like she did this every day. Jeff picked up the bra, put it on his desk in front of them and returned his hands to her body.

Cindy sighed as his right hand went straight to her naked breasts. She sat up straight and arched her back to press them into his hand and make them stand up more for him. Jeff could feel his erection pushing hard into her thighs.

Cindy was still holding the pad and pen and Jeff said, "Start a new note." Jeff continued to feel her breasts and back and tummy and started paying more attention to her firm nipples and dark areola. His wife's nipples were lighter, almost pink. Cindy's were a light brown.

She sighed and turned the page on her pad, ready to take notes.

"I love how your breasts feel."

"Is that for the note?" Cindy asked.

"Yes. I love touching your breasts, I especially like how firm and brown your nipples are."

Cindy was writing and smiling. "Likes tits ... firm brown nipples. Anything else?"

"Yes, I liked watching you undress and I might have to inspect your outfit every day."

She wrote something down while he continued to run his hands over her naked torso, and stopped to tease her nipples since they were so prominent. Cindy moaned and squirmed on his lap, still holding the pad and pen high to give his hands free reign over her body.

"Anything else?"

"Lots more. I liked those patterned stockings you wore last week, I couldn't take my eyes off your legs."

"I remember," Cindy continued to take notes while Jeff tugged gently on her nipples, and she continued to squirm on his firm cock through his pants and her skirt. She seemed to have gotten to a spot she liked.

"Also," Jeff continued "I'm looking forward to exploring how far your talents extend in this direction."

Cindy's squirming was becoming more rhythmic and she mewed, obviously she was enjoying the spot she found to rub. Jeff could feel his cock dripping pre-cum.

"I think you'll be surprised how far my talents will go," She said softly.

Jeff moved his hands to her hips and stopped her motion by holding her firmly. Cindy gave a disappointed moan.

"We should stop this for now or I'm going to have a wet spot to hide," he said.

He held Cindy's hips while she stood and turned to face him, her peaky brown nipples swayed invitingly close to his mouth. She stood facing him and picked up her bra from the desk, putting her arms through the straps. She took her time positioning the cups over her tits then turned around to show him her naked back and the undone bra strap.

"Help a girl out?" She asked as she swung her dark hair to the side.

Jeff let go of her hips and pulled the strap taught across her back and attached the ends. Cindy turned back to him and her dark hair fell forward as she looked down to adjust her bra.

"Will there be anything else right now, Jeff?" Her eyes flicked down to his lap then back into his eyes.

Jeff's erect cock pulsed again at the look, but he shook his head, "No, I think you have a letter to work on, don't you?"

"Yes, I'll get working on it."

Cindy picked up her pen and pad from the desk and made her way to the door. Jeff watched as she slid her blouse back on and button it back up. It looked good untucked and she left it that way as she opened the door and went back to her desk.

Jeff spent an hour doing more work, but his mind kept coming back to his activities with Cindy, and how his wife might react when he recounted what they'd done together. He heard the buzz of a text message on his cell phone and he picked it up. It was Leanne, "any luck? :)".

Jeff was about to reply when Cindy appeared in the door with some papers in her hand. "Do you have a minute to review this?"

"Sure, let's have a look." He put the cell phone down.

Cindy came around the desk and stood right next to his chair. He felt her hip press against his shoulder as she placed the papers in front of him. It wasn't necessary, she could have handed the papers to him, but he'd grown to enjoy the feeling of her warm body so close to his when she did this. She'd been doing it almost every day.

His right arm was trapped on the arm of his chair. If he tried to move his arm, it wouldn't just brush past her thigh, it would rub past inappropriately. Probably rub past her small bum as well, tightly encased in her skirt. Until today he probably would have kept his arm there motionless, enjoying the heat from her body and her delicate scent.

He felt like he was getting away with something, even though it was she who stood pressed so tightly up against him. She didn't seem to think it was inappropriate, she acted like it was a normal way to behave around her boss. Even after their earlier activities, he was nervous about moving his arm and what her reaction might be, but his wife's explicit instructions went through his head.

She leaned forward to turn the page for him and when she leaned back it seemed to Jeff she twisted a little bit to press her tight bottom toward his arm and drag it past him as she returned to her original position.

"I wanted you to review this page to make sure you're happy with everything before I send it," she said.

With his wife's instructions in his ears, he slowly pulled his right arm backwards past her hip. She didn't move. Obviously, she could feel the friction on her hip and her ass but she stayed pressed up tight against him.

"Sure, just hold it there and let me read it".

When his arm was pulled back and his hand was beside her hip he lifted his hand and ran his palm over her hip, over the smooth material tightly encasing her ass. He cupped her ass for a moment before sliding his hand partway down her thigh finally letting his arm hang by the side of the chair and behind her bare legs. She hadn't reacted. "What do you think so far?" She asked.

"Everything seems perfect," he replied. Without looking, Jeff moved his hand forward until his fingertips touched the back of her outside calf. Her leg was bare and cool to his touch. She didn't react. He gently traced his fingertips up the back of her calf and the back of her knee until he reached the hem of her skirt. His fingertips lingered there for a moment then lightly traced back down the back of her leg. Still no reaction.

He moved his hand to the leg closer to him. More boldly this time, he ran his fingers up the back of her calf curling his hand between her legs. As his hand was slowed by her un-parted legs she spread them apart as much as her skirt would allow, and maybe just a little bit more. Jeff smiled to himself.

She was still leaning forward over his desk and he risked a sideways glance at her. She was facing the paper but her eyes were closed and her lips were slightly parted. He could see her arched back and full breasts hanging down and pressing tightly against her blouse. In his glance, he noticed a hint of a firm nipple through her blouse. She spoke softly, "How are you finding this part?"

"I love it, you've done a really good job here."

"Well don't stop, you're just getting to the good part." Her eyes were still closed.

More boldly now, his hand continued up the inside of her knee and to her soft thigh. He didn't stop there and took advantage of her open legs to trace his hand up under her skirt between her legs, slowing as he came closer to her pussy. She shifted her weight as she turned a page on the desk. The result was her skirt rode up her smooth thighs a little more and he felt her legs part a little wider, encouraging him to continue. As the side of his hand came in gentle contact with the gusset of her panties she sighed and shivered. He gently stroked the inside of each of her thighs, each time coming in contact with her panty covered pussy.

He wasn't sure if he should speak and possibly break the spell but his wife's instructions were clear: take control.

Jeff began to gently stroke the lace edges on the gusset of her panties. He could tell they matched the lace edges he saw, and felt, on her bra. He imagined they were the same colour. When he stroked her lips, through the thin fabric, he could feel them become more prominent and he could stroke her private lips individually, or gently down the centre, tracing the path of her slit. "This is excellent work you've done. I'm going to expect this calibre from now on".

"Of course Jeff. I've had this in me all along, you just had to ask. Or tell."

He felt his cock stiffen at those words. Her pussy lips were definitely getting engorged and he was enjoying stroking each of them in turn through her panties, but he didn't want to push his luck too much. As he teased her pussy he wondered what would happen if he abruptly told her to kneel down and suck his cock. He imagined ordering her to strip off her clothes and bend over the desk. A split second later he imagined handing her a sharpie marker and telling her to spread her legs and fuck her pussy with it. As each of these images flew through his head his cock grew more engorged. Jeff wondered if he would tell his wife about those thoughts.

He withdrew his hand from her skirt and patted her bum, "truly excellent work, Cindy. I look forward to more of it."

She stood up, flipped her dark hair, and smiled as she brought her legs back together. "I enjoy doing it for you, Jeff." She looked at his obvious erection and asked, "is there anything else you want me for? I'm all yours for another fifteen minutes."

Again, several lewd images flew through his head. Tying her hands behind her back with her pretty bra, and sucking her dark nipples. Pulling her skirt up and her panties down and spanking her bare bottom over his knee before fucking her with his fingers. Having her fashion nipple clamps and a chain out of paper clips and telling her to wear it home. Cindy stood in front of him, still smiling broadly, like she could read his mind.

The broad smile confirmed his wife was right. Cindy wanted someone to take control of her sexually and tell her what to do. If Jeff didn't, she might get in a situation where she could be hurt. Jeff's mind was reeling about what it would mean if he continued this kinky dalliance. For now, though, he had to regroup and report to his wife. If she put a stop to it, that would be the end.

"No, we've done enough for today. We'll do more work tomorrow."

She looked a little disappointed but she was still smiling. "Ok, see you tomorrow then."

"Oh, and Cindy."

She half-turned and tossed her dark hair to look at him, "Yes?"

"Wear a looser skirt tomorrow please."

Her smiled beamed again. "Sure!" She flipped her hair back and walked to the door with a bounce in her step.