Jeff’s Office Adventure Ch. 04

Chapter 4 - Jeff presses forward the next day.

When Jeff arrived at work the next morning, Cindy greeted him with her usual smile and "Morning Jeff!"

"Good morning Cindy." He took her cheerful greeting to mean there were no misgivings or regret over the previous day's activities. She was wearing a black dress today with black patterned stockings and her hair was back in a ponytail. She looked cute. "How's the day looking?"

"Pretty good. Some calls in the morning and paperwork to review in the afternoon."

"Good, bring in the files for the calls when you have them together." Jeff made sure no one was around. Cindy was standing in front of an open filing cabinet and when Jeff walked past, he put his palm over her ass and gave it a squeeze. Cindy jumped and giggled. Jeff thought he felt a garter belt strap but he wasn't sure, Leanne never wore them.

A few minutes later Cindy appeared in his door and said, "I have those files for you."

"Ok, please put them on my desk."

Cindy closed the door behind her as she came in, which was unusual but Jeff assumed it might become part of her routine if she was enjoying their extra activities.

"Here you go." She leaned forward as she placed the files on his desk and Jeff looked down her dress. Not a sneaky glance, he just stared. The dress was tighter on top than the blouse yesterday, and he could only see the tops of her breasts.

"I see you remembered the note I gave you yesterday afternoon, about the patterned stockings and a looser skirt, thank you."

Cindy was standing to the side of his desk and Jeff turned his chair to face her directly. "Do you remember the other notes I left you with?"

"While you were fondling me you said you liked my full breasts and nipples, and you liked having your hands on them and teasing them."

"Yes, anything else?"

"You said you might have to watch me undress for you every day. I thought that might be fun! It felt really naughty to be topless on your lap. Would you like me to strip for you now?"

"I think I need a pick me up to get motivated for my morning calls. Take off your dress please."

Cindy didn't need to be asked twice. She turned around and held up her ponytail, presenting the zipper on the back of her dress to him. Jeff gripped it and pulled it down slowly, enjoying her naked back as a sliver was revealed. To his surprise her bra strap was bright red under the black dress and as the zipper reached the bottom a black garter belt came into view. The top edge of her panties was the same red.

Cindy turned to face him, holding the dress up and suddenly looked shy. She lowered the dress to reveal a bright red lacy bra and hesitated before stepping out of the dress, one high heeled sandal at a time. She draped the dress over the back of a nearby chair and stood in front of him with her hip cocked to one side. The red lace bra covered her breasts more completely than the blue one from the day before, but Jeff thought she was an erotic vision in the black garter belt and straps with the patterned stockings. He loved how full her breasts were on her frame. The lace tops of her stockings especially caught his attention and the contrast between the black straps over her bright red panties kept him staring.

"I thought all black would be kind of boring, so I added some colour. Do you like it?" She asked hopefully.

"You're beautiful Cindy."

She blushed, but she smiled.

"Turn around for me." Cindy turned in front of him and he took in all of her curves. Her ponytail looked even more playful when she was half-naked. When she was facing him, Jeff held her hips and ran his thumbs over the garter straps. "Not very practical though, are they?"

"What do you mean? Oh, yes. Whenever I have to pee, the straps have to be undone. It's not convenient but girls are used to sacrificing function for fashion."

"I don't think you should be inconvenienced by your garter. Go ahead and take your panties off for me." Jeff's cocked stirred, it turned him on to give her orders.

Cindy undid the snaps on her garter belt. Standing directly in front of Jeff she put her thumbs in her panties at her hips and slowly pushed them down over her stockings until they fell around her ankles. She stepped out of them one sandal at a time.

Jeff's eyes were glued to her pussy as she put her panties on his desk and slowly redid the straps. Her pussy hair was dark, covering her mound. She made no attempt to hide from his view and even stepped to the side, opening her stance to give him a better view of her pussy almost at his eye level.

"Is that better?" She asked breathlessly.

"Yes, much better. You'll be more efficient this way. Hold still while I touch your pussy."

Jeff held one hand on her hip and used the other to run over her mound, almost petting it. Her pubic hair was darker than Leanne's. Of course, Leanne didn't have any at all anymore. Cindy was pushing her hips toward his hand and he ran his fingers through her pubic hair, teasing her mound. The hair was slightly thicker just above her clit and he brushed through it with his fingertips.

"Your pussy feels lovely. Just the motivation I need this morning. Leave your panties here for now, but you should get dressed so we can get to work."

Cindy looked disappointed but she stepped into her dress and Jeff zipped it back up. His fingers lingered on her neck for a moment and she shivered. As she left his office Jeff spread her bright red panties on the corner of his desk where he couldn't help but see them during his calls.

As lunchtime approached, and his calls were winding down Cindy came into the office with a folder and closed the door behind her.

"I have something here and I want your input." She said as she walked up to his desk. As she approached she glanced down at her panties, still spread out on the corner. "Weren't you worried someone might come in?"

"I was ready to hide them, but I liked looking at them. It reminded me you didn't have them on. What do you have for me?"

Cindy opened the folder and spread out five photos, obviously printed on the office colour printer. Each was a photo of a pussy with spread open thighs, so the model's labia was visible. Jeff didn't think any of them was Cindy.

"I have an appointment over my lunch break to get some, um, personal grooming done. I was hoping for your input on what I should choose."

Jeff looked at the photos again and realized they were in a progressive order. The first one showed a pussy trimmed to a bikini line but everything else seemed untouched. The second was similar but all of the hair on the labia was removed. The third photo had a triangle patch on her mound, but the rest of her was bare and smooth. The fourth had a tiny and sparse patch of hair left on her mound, just above her clit. Predictably the fifth photo showed a completely bare mound and labia. Jeff thought of Leanne.

"Hmmm." Jeff contemplated.

Cindy stepped around the desk and stood with her hip pressed against him. As usual, he enjoyed feeling her warmth but today he didn't hesitate. His hand went between her calves and slid straight up to cup her bare pussy in his palm as she stepped to the side, spreading her legs. The loose skirt on her dress allowed her legs to spread much wider than the day before.

"I was going to surprise you, but I thought it would be fun to let you choose since you'll be seeing it so often," Cindy said as she smiled and tilted her hips back to give him better access.

Jeff pressed his thumb between the cleft of her lips and spread them to each side. He gently pushed the pad of his thumb directly on the opening of her cunt and spread the cream leaking from her opening.

"Ohhh, your thumb feels good." She remarked. "Push it in, please? Just a bit?"

"Not yet."

Cindy mewed and pushed her hips back, trying to capture his thumb. Jeff took his hand away and spanked her bottom gently. He held her bare bum with his palm and indicated the fourth photo with his other hand.

"I think this one." As he said this, he ran his fingers up the cleft of her ass and back down to her cunt lips.

"Oh, your fingers are distracting. Not this one?" She pointed at the fifth photo.

"No, my wife just did that. I want you to look a little different."

He felt Cindy stiffen for a second when he mentioned his wife. She started gathering the photos back together.

"But," Jeff continued.

"But what?" Cindy asked and looked at him.

"I think we should take some before and after photos. You know, for comparison."

"Mmm, good idea." Cindy smiled. "Then you can look at them when I'm not around. I hope you stroke your cock while you're looking at them. How do you want me to pose?" Cindy lifted both sides of her dress high enough to display her stocking tops again. Jeff's cock was getting hard.

"Let's take off your dress again and pose you on my desk."

Cindy turned and Jeff reached to pull down her zipper for the second time this morning. He stayed seated while she neatly stepped out of the dress. Jeff patted the desk right in front of him.

"Sit here and lay back."

Cindy perched on the desk in front of him and he held her hands as she laid back. He lifted her feet onto his lap then gently pushed her knees apart. She let them fall open as wide as they would go.

"How's this?"

"You look spectacular."

Jeff pulled out his phone and snapped a photo. Her hips and her pussy were prominent, framed by her garter and stockings but it also showed her bare tummy and bra covered breasts. You could see her chin and mouth but the way her face was tilted back you couldn't see any more.

"Show me."

Jeff handed his phone to her as she laid in this position. He watched as her pussy lips slowly spread apart. The delicate pink of her slit and pussy opening came into view.

"The red bra looks good with the panties, but without them it looks out of place. I think I should take it off." Cindy said as she passed the phone back. Jeff wondered if she could feel her lips slowly opening. He could definitely feel his cock stiffening. Cindy's high heeled sandals were on either side of it.

"Good idea. Pass it to me and I'll get it out of the shot."

Cindy sat up but kept her knees apart. As she undid her bra behind her back she looked at Jeff's lap and smiled. Jeff felt her feet press together, trapping his cock between them. He couldn't help it, he thrust and it felt good.

"Here you go." Cindy was smiling at him as he took the dangling bra from her hands. He was able to drink in the lovely shape of her nude torso and large bare breasts as he continued to press his cock between her sandals. Cindy's brown nipples crinkled and firmed up under his gaze.

"Let's try again," Cindy said as she reclined to her previous position. Jeff examined her pussy again and saw her slit had opened up, all the way to her pink hooded clit. His cock throbbed as he took another few photos.

"What should I do with my hands?" Cindy asked.

"I don't know, I'm not looking at your hands. Try different things."

Cindy giggled and Jeff's cock throbbed even more between her feet. If he wasn't careful he was going to come.

He continued to snap photos and Cindy moved her hands around to pose in different positions. She covered her breasts, pressing on her firm nipples, then held one on her hip to contrast her bright nail polish against her skin and garters. She pinched one nipple and lifted her breast with it, and finally stretched her pussy lips wider with her fingers. Jeff could see some pussy cream dribbling out of her pink opening.

"Anything else?" She asked breathlessly.

"Yes," Jeff said spontaneously. "Use this for me." Jeff picked up a bright blue highlighter from his desk and handed it to her. One end had a cap, but the other end was smooth and rounded.

Cindy took it from him and said "You want me to push this into my cunt for you? Use it to fuck my tight, wet pussy while you watch and take photos? Only a really naughty girl would do something so improper. Only a dirty, slutty girl would enjoy it. I'll be your filthy, slutty girl because I need something in my cunt." As she was talking she was running the smooth end of the highlighter around her opening collecting her cream and making the highlighter wet. As she finished speaking she pressed the end on her tight opening and Jeff watched it slide in. He took photos. When it was mostly in her pussy she took her hand away and Jeff couldn't believe how lewd it looked, poking out of her cunt. He held her thigh and took more photos. Cindy was trembling slightly.

Her hand came back and she gently rested her fingertip on her exposed clit and started rolling it under the pad of her finger.

"Should I masturbate for you now? Would you like to watch while I stroke my clit in front of you, and come on your desk? Because I will. I'll do whatever you want, and I'll enjoy it." She panted. "Tell me, Jeff. Tell me to do it."

Jeff cleared his throat. His phone was forgotten for the moment in his hand as he watched her. "Do it. Be my dirty little slut, Cindy. Stroke your clit while I watch." Cindy moaned and Jeff continued. "If you want my fingers, or my tongue, or my cock in your cunt, you'll do this for me now. Play with your clit so I can watch your pussy come."

Cindy stroked her wet clit up and down with her finger. Jeff saw it firm up and respond to her own touch. She stroked faster. Jeff remembered his phone and hit the button to begin recording a video.

"I want all of those things. I want you to use my cunt whenever and wherever you want. All you have to do is ask and I'll strip and open my legs for you. Use my mouth and my cunt and my tits however you want. I'm yours to play with." Cindy panted these last words out. Her fingers were strumming her clit in a blur and her large breasts were moving with her rhythm.

"Will you greet me in the morning naked and bent over my desk?"

"Yesss!"

"Can I tie you to a bed and fuck you all night?"

"Yes, I'll bring the rope."

"Will you suck my cock and let me come in your pretty mouth, while I talk to my wife on the phone?"

"Yesss pleassse! Uhhhh!" Cindy panted and moaned out.

With those words, he watched Cindy come hard, letting out a small scream as her pussy rhythmically clamped down on the highlighter, still lewdly protruding from her cunt. It was being pushed out of her pussy by her pulsing squeezes and he pushed it back in with his hand. She gasped and her orgasm continued. As her orgasm calmed, he hit stop on the video recording.

Cindy looked up at the phone in his hand. "Did you take more photos?"

"I took a video of you coming. Do you mind?"

"Of course not. Can I watch it?"

"Sure, let's sit on the couch and you can see the photos too."

Jeff helped Cindy up from the desk. All she was wearing now was her black stockings with the garter belt and her high heel sandals. He led her to the couch. As they sat, she reached into his lap and held his firm cock through his pants with both hands. Cindy gave it a gentle squeeze and started stroking it with her hands and smiled.

"OK, show me the photos."

Jeff opened the photos on his phone while Cindy undid his belt and pants. She looked down and her dark ponytail swung forward over her shoulder. He lifted his hips so she could pull his pants and boxers down his thighs. As her hands returned to his erect cock, now bobbing in the open, she looked up into his eyes with a hopeful expression.

"Do you mind if I stroke your cock while we look at the photos of me?" Her hands were lightly running up and down his shaft, then one hand cupped his balls and stroked his scrotum while the other played with his head.

Cindy was sitting slightly sideways so she could have both hands on his shaft. Her breasts were hanging forward and her arms pushed then together. Jeff liked how her breasts moved with her stroking. "No, I don't mind, your delicate hands feel great on my cock. If you keep it up, I'm going to come all over you."

I think I'd like to have your cum on me. Now show me the photos."

Jeff held the phone where they could both see it and tried to concentrate on the photos instead of what her hands were doing. One hand was pumping his shaft slightly while the other was spreading his pre-cum around the crown of his cock.

"Here's the first one." Jeff left it on the screen for a few seconds before flipping to the second photo.

"I'm glad I took off the bra," Cindy said, "it didn't look right without the panties." Jeff continued to flip through the photos of her spread pussy, covered in pubic hair. "Oh, I could feel my pussy lips opening up before you took those. When I stretched them open with my fingers it felt wonderful."

Cindy was stroking his cock more vigorously, Jeff's pre-cum had coated the hand on his cock head, her other hand was sliding the skin on his shaft up and down slightly. On each downstroke, it pulled gently on his sensitive frenulum. Jeff wondered if the feeling was similar when Cindy pulled her slit open with her fingers.

"Here's where I gave you the highlighter." He watched Cindy looking at photos flick by, her attention caught by each one as it showed her tease her own pussy opening with the blue object, and then push it into her.

"Ohh, that's a good one," Cindy remarked. Jeff stopped on the photo where she had let the highlighter go and it was protruding from her spread cunt. He thought it was a good photo too. His cock was throbbing, and he could feel his balls churning but Cindy was doing a good job of controlling his orgasm, her touch getting lighter as he got too close to coming.

"I like this one." He said. The photo on the screen showed her finger just resting on her pink clit. Before she could respond he said, "I like this one too." In the next photo, her finger had pulled away from her clit, but a wet strand of her cream connected the tip of her finger to her aroused, firm clit.

When he flipped to the next photo, it was a video, with the large 'play' button in the center.

"Play it for me, I want to watch," Cindy said and looked up at him hopefully. She was continuing to stroke his cock and doing an excellent job of keeping him on the edge of an orgasm.

"Ok, let's both watch you come."

He hit play.

"I want all of those things. I want you to use my cunt whenever and wherever you want. All you have to do is ask and I'll strip and open my legs for you. Use my mouth and my cunt and my tits however you want. I'm yours to play with."

Jeff was looking at Cindy as the video played. She was mesmerized as she watched herself on the video, but her hands never stopped on his cock.

"Will you greet me in the morning naked and bent over my desk?"

"Yesss!"

"Can I tie you to a bed and fuck you all night?"

"Yes, I'll bring the rope."

"Will you suck my cock and let me come in your pretty mouth, while I talk to my wife on the phone?"

"Yesss pleassse! Uhhhh!"

Jeff felt Cindy clench her thighs together beside him and heard her moan when they watched him push the highlighter back into her pussy on the screen. She looked up at him.

"Oh my god, I loved watching myself come!" She said with her eyes wide. Cindy leaned forward and the tips of her breasts rubbed against his shirt as she continued to stroke his cock. "What will you do with those naughty photos when you get home Jeff?". Her face was close to his and she almost whispered the question, smiling.

Jeff wondered if he should be truthful, and decided things would get complicated fast if he wasn't. He was enjoying being this close to her, feeling her warmth and softness. He didn't want to lie.