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Views: 503 Created: 2 years ago Updated: 2 years ago

Cindy’s Adventures

Chapter 3 - Working for Tony

Cindy woke up early on Saturday, like she did every day. Lying in bed naked, she started thinking about her appointment with Tony. As she thought about him and working beside him, her fingers drifted down her stomach, through a small tuft of pubic hair, and nestled into that crease that felt so good. A little pressure, a little circular movement, a little roll of her hips. The warm energy started to grow and tingle inside her. As she rubbed herself she continued to think about Tony. She thought about him touching her, exploring her body, with just the right amount of gentle and rough. Cindy could feel her labia getting wet and slippery. She dipped her finger inside and brought it back to her clit, slipping and sliding it around and around. Cindy could easily reach an orgasm right now, but she decided to hold off and save it. She enjoyed carrying that kind of horny energy with her throughout the day. When she got home tonight she would reward herself with a deep, strongly brewed orgasm. She dipped inside one more time and then carefully brought it to her mouth, first licking, then sucking the sweet and tangy juices from her finger.

Cindy took a shower and got dressed. While she often relaxed in yoga pants on the weekend, she decided to be bold and wear a skirt today. It was a warm sunny day and the walk to Tony’s house was only about 3 km.

Her morning stroll took her through the village. Cindy walked past a park and a couple of street side coffee shops. There were many people out and about, enjoying the nice weather. Cindy waved to a few people that she knew along the way.

When she arrived at Tony’s house Cindy smoothed out her skirt, tucked her hair behind her ears, and knocked on the door. A few moments later Tony opened the door and welcomed her in.

Tony’s house was small, but comfortable. It was in better condition than Cindy had expected for a single guy. He had an eclectic style, with a surprising amount of art on the walls.

“It’s great to see you. Thanks so much for coming.” Tony said.

“I’m happy to help.” Cindy replied. “After all, you did win the auction. Or rather, co-won the auction.” She let out a small laugh, still not knowing what was in store for her.

Tony laughed with her. “Can I get you something to drink?” Tony offered. “A water, or… I just made some lemonade.” Tony put two glasses on the table and took a pitcher of lemonade out of the refrigerator.

“A lemonade sounds lovely. Thank you.” Cindy answered.

They sipped their lemonade and nibbled on some warm muffins Tony had picked up that morning from a local bakery. They exchanged some small talk for a while. He told her stories of where he had acquired some of the paintings and drawings he had hanging in the walls. Cindy admired the large windows in his living room that looked out on his backyard. Tony opened one of the windows to let the warm breeze in. They could hear neighbors on the other side of the garden wall having a luncheon outside.

Cindy was enjoying Tony’s company, and when the conversation paused for a moment Cindy worked up the courage and asked, “So, what did you need help with today?”

“Ah. Yes. Thanks for reminding me. You see, I started taking art classes a few years ago.” Tony explained. “At first I was painting, mostly landscapes.” He motioned to a couple paintings on the wall. “But recently I’ve moved more into figure drawing.”

“Oh.” Cindy said inquisitively.

“When I saw you standing on the stage at the club it reminded me of the models that would come to our studio and pose for us while we were drawing.”

“Oh. Wow.” Cindy said, a little surprised at the compliment. “Thank you.”

“I figured it would be easy work for you, and I would be able to get some practice.”

Tony removed a few items off the coffee table and turned to Cindy. “This little table here is just the right height.”

“Just the right height for what?” Cindy asked. She was a bit nervous that she didn’t fully understand the situation.

“You are going to stand up here and pose, while I draw you.”

“Oh, my.” Cindy uttered. She was flattered, and confused. She stepped towards the table. “You just want me to stand up here?”

“Yes. It's as easy as that.” Tony said cheerfully. “Now, I’ll get my sketchbook ready while you change. There is a robe over there behind the screen.” Tony pointed to a three panel folding screen in the corner of the room. Cindy looked at the screen and then back to Tony. The blank look on her face told him she was not familiar with this routine.

“You can change there, behind the screen, out of… this.” He gestured to her outfit, “and put on the robe I set out for you.”

Cindy was embarrassed that she did not fully understand the situation, but cautiously walked to the screen to avoid any further explanation from Tony.

Behind the screen she found a white bathrobe. Did he really expect her to change out of her clothes and wear a white robe? This was not at all what she had envisioned, but she did not want to let him down, so Cindy took off her blouse and skirt, hung them on the hook, and put on the robe. There was no belt to tie around her waist. She closed the robe tightly around herself, held the flap in place with her arm, and cautiously stepped out from behind the screen.

Tony had set himself on the sofa with a large sketch pad and a bag of art supplies. He looked at her like this was a completely normal situation, and motioned her to the coffee table. Just as she was about to step up Tony interrupted her.

“Shoes.” He said. “You can leave them right there, next to the table.”

Cindy awkwardly bent over to unbuckle her sandals while trying to hold the robe closed. Once she was barefoot, she looked back to Tony for approval, and then stepped up onto the table.

She was uncomfortable being up so high, while he was seated, looking up at her.

“How about we start with a simple pose.” Tony instructed. “Reach out like you are picking an apple from a tree.”

“Ok.” Cindy answered quietly. With one hand she held the robe closed and with the other she reached out to pick an imaginary apple.

“Uhh… Ok” Tony said slowly. “We’ll keep the robe for now.”

Tony began sketching. His hand was fast, the strokes were long. Cindy could tell he was not working out details, but rather full curves of her arm and body. She didn’t know what to look at. She tried to keep her head still, but her eyes darted back and forth between her hand, the window, and Tony on the sofa. His eyes were focused on Cindy. He barely looked at his paper. He looked her up and down, from the tip of her fingers all the way down to her feet. Cindy could feel herself becoming very self conscious about her body, particularly her forearms and calves which were not hidden behind the robe. Tony was an attractive guy and all, but this was too much too fast. This is not the sort of casual contact she had hoped for.

“Ok, let’s try another pose.” Tony broke into her thoughts. “This time let’s try your feet apart a little bit, hands on your hips, strong chin up, like you are standing guard at a doorway.”

Cindy lowered her arm and tried to figure out how to put her hands on her hips and still manage the robe.

“And this time.” Tony added, “You can drop the robe.”

What? thought Cindy, drop the robe? I couldn't possibly. I already took my clothes off. Does he want me to take off the robe I just put on?

Tony could sense her hesitation. “I understand. You're not used to doing this. The models do this all the time in class. I promise to keep this very professional.”

He looked Cindy directly in the eyes. She could tell he was serious, and expected her to comply. She took a deep breath, resigned herself to accept the impending indignity, removed the robe and dropped it to the floor. Her arms instinctively tried to hide her bra and knickers. If she had known this was going to happen she would have picked out a better looking set of undergarments. Of course, if she had really known this was going to happen she would have canceled.

Tony looked at her and sighed. It was a mix of disappointment and mild frustration. This made Cindy more uncomfortable.

“Hands on hips.” he repeated. “Chin up.”

Cindy moved her arms to her side, placed her hands on her hips, and lifted her chin. She was standing in front of Tony, barefoot, and almost naked. She did not like this one bit. She did not like how exposed she was, and how he was looking so closely at her body. She did not like guarding this imaginary door.

Tony started out sketching quickly, but then slowed down, spending more time focused on certain spots. He leaned his head to the side while he studied Cindy’s form. He followed the muscles and the bones, through her shoulders, arms, and hips. At least she still had her bra on, Cindy thought. The last guy who had seen her in just a bra and knickers was a bartender she shagged on a vacation last summer. Maybe a bra and knickers was not that different from a bikini. Still, she was in an almost-bikini and he was fully clothed. This did not make her comfortable. It didn’t look like she was going to be hooking up with Tony, although the possibility did keep running through her mind.

“Alright, let’s try another.” Tony picked up a metal tray and handed it to Cindy. “Hold this with two hands, like you are offering a drink to someone.” He put his glass of lemonade on the tray. Cindy carefully held the tray, balancing the glass. Tony walked to the side of the coffee table. He gently touched Cindy’s elbow, guiding her arm a little more forward. The contact of his hand on her bare skin gave her a brief shiver. It felt good. It felt good to have him position her the way he wanted. He touched her back slightly, straightening her posture. She felt an exciting energy from him being so close to her. Then suddenly she froze. Before she could even blink he had unclipped her bra and dropped it down the length of her arms. With her bra straps still around her wrists, he flipped the bra cups onto the tray and returned to the sofa. Her breasts were bare.

Tony picked up his sketch pad and resumed drawing while Cindy stood there, stunned, unable to move or talk. Not only was she up on the table with her tits out, but the tray in front of her now held a glass of lemonade and her bra. Although her heart was racing, her mind was giving in, giving up, and accepting her situation. She was not the one in control here. Her job was to stand on this coffee table, and do whatever Tony asked her to do.

As a defensive mechanism, Cindy tried to remain very still. Don’t move, she thought to herself. Don’t think about it, just do as Tony says and it will all be over soon. Then Cindy felt one of her nipples start to harden. It was a completely involuntary reaction, as she was not touching them or even the slightest bit turned on. Nevertheless, first one nipple then the other scrunched up. This was so embarrassing. Tony was sitting right in front of her, staring at her mostly naked body, and now he was watching her nipples harden and push forward. Why me, she thought. Why is this happening?

Then Cindy noticed an even more horrifying development. There was a new wetness between her legs. She could feel the slipperiness of her labia touching together, and her damp skin touching her knickers. She didn’t think she was turned on, but her body was giving all signs to the contrary. Cindy couldn’t imagine this being any more uncomfortable than it already was.

When Cindy was able to calm her thoughts she focused back on Tony. He was staring at her. He had been waiting for her to come back from her day dream.

“You OK? Tony asked.

“Yes.” Cindy replied quietly, not daring to share any of the many feelings that were swirling through her mind.

“Let's try a sitting pose, shall we?” Tony said. He stood up and took the tray from Cindy. With his carefully placed thumbs, Tony ensured that the bra came with it. Cindy stood before him, thankful that at least she still had her knickers.

Tony lifted a simple straight back wood chair onto the coffee table. He placed it facing away from the sofa. Cindy wondered if he wanted to draw her from the back.

“There you go.” Tony said. “How about you sit here, straddle the chair, and rest your arms on top of the chair back.”

Cindy did as she was told. Her legs were spread wide, her arms crossed on top of the chair back. She leaned forward and rested on the chair.

Tony sat back on the sofa and looked at Cindy. Her crotch was almost at Tony’s eye level. The chair back stretched her pale thighs wide, showing the muscles and tendons of her groin. There was a small concave zone at the inside of each thigh, where her delicate skin disappeared under that little strip of cloth. Then Tony saw it. In the center of the fabric gusset there was a little dark spot, not much bigger than a freckle. Cindy’s knickers were a light gray, probably cotton. The spot was dark gray, and it looked wet.

Tony had been planning to sketch her crossed arms on the chair back, her thighs pointing out, and her bent knees. Now he switched gears and focused on her inner thighs, the fabric pulled snugly in between, and the subtle shading of this small damp patch. The chair back slats framed this little scene nicely. Tony was captivated.

Cindy was not aware that her wetness was visible. She was much more concerned with the way her breasts were hanging down from her hunched posture. She was certain this position was causing her nipples to point more down than forward. Why was Tony so cruel? Why do men never understand the difference between a flattering position and an absolutely most horrible wretched pose?

Tony was thoroughly enjoying this pose. The curves of her thighs, the taught fabric, the hint of what was hidden beneath. Each time he worked his way back to the dark spot he swore it was larger. No longer the size of a freckle, it had certainly grown to the size of a finger tip. He stroked the tip of his pencil over the sketch of her gusset, adding a little shading to edges. He imagined his finger tip sliding over her gusset, gently pressing on the tender bits hidden inside.

Cindy could feel his focus. He was not looking at her face, he was not looking at her outstretched knees. Tony was concentrating on the intersection of thigh, fabric, and chair. There was nothing she could do to hide it. She was forced open for him, spread wide, exposed and helpless.

Cindy felt a growing need for contact between her legs. It was a dull ache that needed to be rubbed. She needed some pressure applied. Normally a subtle squeezing of her crossed legs would calm this feeling, but the chair back was preventing this. She very slowly rocked her pelvis on the chair, trying to make contact with the seat, but it couldn’t reach. All she could feel was the growing wetness between her legs. Tony was aware of it too. The wet spot was now larger than a coin.

“You're doing great.” Tony said. “But I think the standing poses work better.” He turned the page of his sketch pad, set it down, and reached out to remove the chair. Cindy slid back, awkwardly dismounted, and stood up. She was finally able to close her legs and give herself a secret squeeze. Ahhh, it felt good. It took the edge off her ache, but did not completely relieve it. The craving for attention had now spread to her clit. Cindy was very aware that she was practically naked and Tony was completely clothed. While the whole setup was awkward and unfair, it was all making her a bit horny.

“How about you turn around.” Tony instructed. “And face the window.”

Cindy did as she was told and turned to face the window.

“Try placing your hands behind your head. Feet slightly apart.” Tony asked.

Cindy complied.

“Oh, Yes. This is good. Your shoulders, neck, and back. Wonderful curves, all the way down to your waist and your…” He paused.

Cindy assumed he was looking at her ass, or at least her clothed ass. It wasn’t much cloth, but it provided her with a little remaining dignity.

Then Cindy felt Tony’s hands on her hips. She held her breath, both excited and nervous by the touch of his skin to hers. He turned her slightly and held her still to fix her in place. The firmness of his grip made it clear to Cindy she was not to move.

“We really should lower these.” Tony said. He hooked his thumbs into the waistband of Cindy’s knickers and pulled them down to her knees. Cindy didn’t dare look down. She could feel that her last line of defense had been taken. Her knickers were now stretched between her knees like a hammock.

Tony saw it first. The wet spot he had studied on the outside of her gusset was only a small portion of what had soaked through. The inside of her gusset was much wetter, with a large patch that was long from front to back. The shape of the wetness clearly explained where all this moisture has come from, like a fingerprint left by a finger. Cindy had left quite a significant print in the center of her knickers.

Tony sat back down at the sofa and stared at Cindy. With her up on the table he could look down slightly at that wet gusset, or look up slightly at her wet labia. He was glad she was facing away and could not see him as he reached into his pants and adjusted his swelling manhood.

Tony started sketching every little detail he could see. The roundness of her cheeks, the dark crease of her butt crack, the way her generous labia protruded and were visible between her legs. The bright light from the window showed between her thighs, highlighting and glistening on all her wet folds of skin. It also highlighted the condition of that gusset between her knees. Not only was it damp with wetness, but there was a thick creamy look to some of it. Tony imagined it being slippery, warm, and sweet.

Cindy stood still, looking straight out the window. She hoped and prayed that nobody from the luncheon next door walked over into Tony’s backyard. This was humiliating enough with an audience of one. It would be unbearable for an audience of more. Cindy remembered standing on that stage at the club last week, with her back to the audience and everyone staring at her. The embarrassment, the anxiety, and the racing heartbeat of excitement. Why did her body give her so many mixed signals? Why was she almost on the verge of tears, while her pussy was as wet as could be? With her knickers down she didn’t dare roll her hips or squeeze her legs. She just had to endure this growing ache deep inside her. She was desperate to be touched.

As Tony sketched he stayed focused on Cindy’s labia. The slight separation between them, the puffiness, the folds, and the shine of the moisture clinging to the sides of her inner thighs. He so desperately wanted to reach out and slide his finger between them, to curl it up and rub her clit. He wanted to feel that slipperiness on his fingers, and then he wanted to taste it. He now regretted telling Cindy that he would keep this activity completely professional. Right now he wanted to be very unprofessional with her.

“Alright, you should probably step out of these.” Tony said, taking hold of Cindy’s knickers and lowering them further. He held them in such a way that Cindy could step out of them. As she did she looked down and saw for the first time the damp patch, the wet mess she had left on the gusset. OH. MY. GOD. She thought. Tony knows how thoroughly wet I am. He should never have seen the inside of my knickers.

Tony turned and placed Cindy’s knickers in his art supply bag. He looked forward to revisiting them later when he was alone.

“Ok, time for another.” Tony said. “Is there a pose you would like to try?”

Cindy thought for a moment, but had no experience in figure drawing and didn’t know what to do. She didn’t want to disappoint Tony, so she fumbled and settled into something easy. Her legs were together, one hand on her hip, other hand up and out, like she was

pointing at something. She turned to Tony, looking for his approval.

“Well,.. Ok.” He said. “It’s the classic teapot position.” He smiled at her and began sketching.

Cindy immediately felt ridiculous. How could she have picked something as silly as a teapot? Now she had to stand like this while Tony sketched away. She looked at him, fully clothed and working with a smile, while his gaze floated all over her. She felt so very naked. She wondered if her labia were showing. She kept a little tuft of pubic hair up high, but usually shaved everything down below. She hoped her clit was not peaking out, but she couldn’t tell without reaching down and touching herself. Tony could probably tell. He was looking right at her crotch. Cindy gently squeezed her thighs and applied a little pressure to that ache growing inside her. At least this position allowed her to clench her muscles without making a big scene. With each squeeze she could feel how wet she had become. No matter how uncomfortable she felt, it was clear that from her shoulders down her body was tremendously turned on.

“Ok, now sideways to me.” Tony asked.

Cindy lowered her arms and turned to the side.

“Can you touch your toes?” He asked.

“Almost.” Cindy replied.

She bent over and brought her fingers almost to her toes.

“Can you hold that pose?” Tony asked.

“For a little bit, I guess.” Cindy answered. Thankfully she had her side to him. It was a little awkward, but she felt slightly protected.

Tony turned the page and began drawing. The curve of her calves, the roundness of her ass, the arch of her back, and the undulating muscles of her upper and lower arms. Cindy wrapped her fingers around her ankles and held herself still. It reminded her that she should stretch more often. She always wished she was just a bit more limber.

Tony turned the page in his sketchbook and stood up. Cindy stood up too.

“Oh, I’m not done.” He said with a hint of authority.

Cindy obediently bent back over and returned her hands to her ankles. It was embarrassing to be caught doing the wrong thing.

Tony walked over to another chair in the living room, sat down, and resumed sketching. Cindy could not see him any more and she wondered where he was. She turned her head and looked between her knees. There was Tony sitting directly behind her. With her head upside down she could not tell if he was looking at her eyes or not, but it didn’t matter. Cindy‘s only thought was how much of her private place was now visible to him. She could feel her face flush from embarrassment, and from being upside down. She could also feel the wetness growing between her folds. Oh God, she thought. Please don’t let him be able to see my wet little hole. I can’t take much more of this.

Tony could see all of her. When he changed chairs he had also been able to discreetly reach into his pants and adjust himself in a more upward direction, giving room for his growing erection to extend and swell. Cindy’s wet folds of skin were protruding out from between her upper thighs. The separation of her ass cheeks was giving him a perfect view of her tight little ass pucker. He wanted so much to bury his face in her warm crevasses. He was no longer drawing, but just studying the inner pink regions of her most personal places.

“Oh, my.” Tony said suddenly. “It’s already 4 o’clock.” Time sure has gone fast.

“Oh, no. 4 o’clock?” Cindy asked. “I really must be going.” She had so much to do before her dinner date. She waited for Tony to say something. She didn’t want to move again unless he said he was done.

“Almost done.” Tony said “Just another moment.” Tony was not drawing, but wanted to stare into Cindy’s bent over body just a while longer. After scanning her up and down a few more times he said. “Ok. All done. You may get up.”

Cindy worked herself back up to vertical, stretched her back and turned to face Tony.

“I’m sorry, but I really must be going.” She apologized.

“Not a problem.” Tony replied. “You were a wonderful model today. This worked out even better than I had hoped.”

Tony held out his hand and helped her step off the coffee table. Cindy walked quickly to the folding screen in the corner to get dressed. Reaching for her blouse she realized Tony had taken off her bra. It was probably on the sofa, with her knickers. Her soaking wet, creamy knickers. She couldn’t bear to face him again over the sight of her messy gusset. She hastily decided to ignore them and go without. The sooner she could put this whole ordeal behind her the better. She'd rather leave them behind than discuss them with him. She pulled her blouse on and then her skirt. Her breast hung freely without her bra. And the air around her nipples and her crotch make her feel very naked under her clothes. It was a funny feeling, being both clothed and exposed at the same time.

Cindy stepped out from behind the folding screen, slipped on her shoes, and headed for the front door. Tony was there to open it and say goodbye.

“Thank you again.” Tony said as Cindy was leaving. “It was a great drawing session, and well worth the donation I paid to the club.”

“Thank you.” Cindy replied. “Sorry I have to run. I’ll see you soon. Goodbye.”

Cindy turned and headed down the street, eager to get home and forget about this whole embarrassing ordeal.

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