Cindy, The Babysitter


HI Guys, this is my first attempt at writing and my first submission for Literotica. Hope you will enjoy reading the same. I would love to hear your comments and any feedback you have. I would like to thank Literotica user ‘Laurielou’ for their help with the editing of this story.


As Cindy looked into the mirror, she thought she had one of the most beautiful smiles ever. Other girls her age might be insecure about their looks, but not Cindy. She loved every aspect of her body, her features and all her curves. She stood naked after a shower and was about to get ready to go to college. In the mirror she saw a beautiful pair of green eyes stare back at her below a perfect pair of eyebrows which matched her wavy black hair. She had a heart-shaped face and amazing red lips.

She ran a hand over her skin, touching her fresh, smooth body that she was proud of. She had a thin, petite body and stood at a 5’4″. She had all the right curves and a rack to die for. She cupped her titties and let them jiggle a bit, smiling mischievously. At a C cup, they were firm and quite a handful. She also had amazingly sensitive nipples which would get aroused with the slightest touch. She passed her hand over her flat stomach, pinching here and there, checking for hair. The skin on her hands and legs was smooth, taut and hairless – just like her pussy. She spread open her pussy lips with two fingers and thoroughly checked for any hair. Once convinced, she rubbed the pink bud of her clit. She bit her lip as a current passed through her body at the touch of her own fingers. She turned around and bent over to see if any stray hair was near her hole. She had an amazing ass, big, round and perfect for smacking. She smacked her ass cheeks and giggled as they bounced. She was feeling like a teenager; why shouldn’t she? She checked the calendar instinctively. It was only a month since she had celebrated her nineteenth birthday. She was still a teenager.

Cindy was quite rich and though in college she had her own apartment and a car. She lived alone. People thought, and she encouraged the rumour that her parents were wealthy and took care of all her needs. Her eyes strayed to a family photo on the dresser and she snorted. They were rich and almost always too busy for her. She didn’t hate her parents but a lot of her choices in life were to rebel against them for never being there for her. With time, Cindy had gotten used to being away from them and a monthly call with her mother was all she had to bear to ensure she got her substantial monthly allowance.

She worked as a babysitter part-time with a slightly different kind of agency. This agency worked only with the very rich clients and the money was amazing. That more than anything was the source of her real income which helped her maintain her exuberant lifestyle.

She was thinking about her day ahead. She had been called by one of her professors for a one-on-one meeting for not submitting her assignments thrice in a row. It wasn’t that Cindy was a bad student, but in this particular case she had been purposely not submitting her work. The professor was a very good-looking, middle-aged bachelor. She had had the hots for him throughout the year. She had teased him during class through the year, sometimes even making him uncomfortable. She looked forward to meeting him alone to see if she could take the teasing a little further. Cindy had a real fetish for older men. She preferred them over the college idiots who were hopeless at being able to satisfy their women. She liked her men to have experience, to know their way around and, most of all, take control over her. She felt wet thinking about what she could do for the professor.

As she was pulling her T-shirt over her head, she heard her phone beep. It was her babysitting agency. When she was approached the first time she was a little sceptical about their means of communication, but now she was used to their cryptic style. She had never talked with anyone at the agency. They only ever conversed over messages and these were short and curt. Usually they sent her only the location and the job. Once the job was done, her account was credited with the money. Of late, Cindy got a lot of work. She had made quite a name for herself. She wasn’t too picky about the clients and usually agreed to work with everyone. For the right amount she took up the toughest jobs and unruliest of people that the other babysitters would not touch. She read the message.

Agency: Would you be interested in a job today?

Usually if the job was a simple one, they wouldn’t really ask her but send only the instructions and time. Since they asked if she was interested, she knew it would not be a regular job.

Cindy: What is the job?

Agency: Multiple clients to be taken care of from 8 PM till past midnight.

The lateness of the hour did not bother her; usually the clients or their drivers dropped her home. If not, then someone at the agency would send her a car with a driver. Something was nagging her though.

Cindy: Maltepe Escort How many exactly?

Agency: Five and they might be quite a handful from our understanding. However, the payment will be of the highest grade.

No kidding. Five? She had handled only two together and only twice before.

Cindy: Any other babysitter accompanying me?

Agency: No, you will be alone, and they have specifically asked for you as you have been highly recommended.

This made her nervous, but it also made her excited. This was something new and interesting.

Agency: You can of course decline. It is completely your discretion. However, we have credited half the payment as an advance for your consideration.

She got a message from her bank and when she saw the amount she whistled softly. Anyways, not for nothing was she one of their top babysitters. Screw it, there is always a first time, she thought. She would take up the job.

Cindy: Special instructions from the clients?

Agency: None whatsoever. You are to make yourself available at the below address at 8 PM sharp and the client has agreed to drop you home after the job. We will be available on the hotline and on standby in case you need us.

Cindy: Ok. Thanks.

She saw the address and grinned. The neighbourhood was one of the richest in that city.

At a sharp 8 PM she rang the bell of one of the biggest houses in the neighbourhood. She was shown into the sitting room by the butler. As she was looking around and taking in the surroundings, a group of five ladies entered the room. They were all slightly drunk. All of them wore expensive clothes and jewellery but not all of them looked classy. They were all middle-aged or older. One of them who had a business-like expression on her face addressed her.

“Thank you for taking them off our hands for the night. We all have been looking forward to having a girls’ night out. Hope you will be able to manage all of them?” she asked.

One of the other ladies giggled. Cindy was irritated but kept her composure and replied, “I am certain I will be able to manage. My services are always…satisfying…You will have no cause for complaint, Mrs…”

The lady smiled but did not reply. She looked directly into the girl’s eyes and said, “I thought the service was a discreet one.”

“Of course, it is. I am sorry, you needn’t reply. If that is all?” Cindy replied raising her eyebrows.

“How old are you?” asked another one of the ladies who seemed to be the eldest of the lot. Cindy smiled not wanting to be drawn into it.

“Well, as Madam said, this is a discreet service. You have your secrets and I can keep mine. I assure you though, I am old enough to complete the job to… satisfaction,” Cindy answered, grinning.

The lady blushed, and the others laughed at her discomfort. The lady, who had first addressed her and seemed to be the owner of the house had not laughed, she simply smiled icily at Cindy.

“Don’t get too cocky,” she said. Pointing at the butler she added, “Adam here will take you to change your clothes first and then show you the way to the card room. They are waiting for you there. He will also arrange the transportation tonight for you. Or for what’s left of you.”

She got up, and led the ladies, who were still eyeing Cindy and giggling, out.

The butler didn’t speak much. He led her to one of the rooms on the first floor and silently waited for her to enter. She went in and saw a black and white maid’s uniform with frilly ends lying on the bed. She picked it up and saw it was small – even for a petite girl like her. The was a note with it: Wear only what is on the bed and use the makeup from the dressing table.

She wore the tiny black thong which was lying on the bed that fit her snugly. The uniform was a tight fit, but she managed to finally pull it over herself. There was no bra, but the dress pushed her breasts up and the deep neck of the frock showed ample cleavage. The dress enhanced her curves beautifully. She wore a red hairband, white gloves, netted stockings and black pointy heeled shoes to complete her look. The skirt ended high and left little to imagination. In case she bent over, the skirt went all the way up and exposed her thong-covered ass. She put on some makeup, ending with a luscious red lipstick. Once she was ready with her outfit she stepped out of the room. Adam turned on his heels and led her to the doorway of the cards room, then left. She ran her hand through her hair, took a deep breath, and entered the room.

The first thing she noticed was how chilly the room was. On the table sat five fully grown men whom she was supposed to babysit for the night. They were older men, and she immediately realised the women she met before were their wives. They were playing poker and had drinks in their hands. They had peppery grey hair and two of them were also balding. The smell of alcohol was strong in the room. Cindy had no qualms about why she had been called here. Kartal Escort As she stepped in, one of the guys stood up and came to her, smiling. He was easily old enough to be her father. She smiled seductively at him.

He hugged her tightly and planted a kiss on her cheeks. Then putting a hand on her butt, he squeezed it and pushed her forward to the table. Four pairs of hungry eyes stared at her. Other girls would have been nervous or even terrified of the looks she was getting. Not her, she was calm and, in her element, anticipating what was going to come.

“For today you can address us as Hardy, Henry, Jerry, Jack and myself as John,” he said, pointing his glass at each one of his companions. Henry seemed to be the oldest of the lot and the fattest. The others seemed well maintained for their age as if they worked out regularly. John seemed to be the leader and the host for the night. Jerry was gaping at her with his mouth open.

“Get yourself a drink, sweetheart, and join us at the table,” added John and smacked her ass. Cindy went and got herself a beer. She was already feeling wet with anticipation at what was to follow. She stood at the table sipping her beer and watching their game. Jerry won the hand.

“Come here sweetheart, sit on my lap,” Jerry called out. She smiled, cat-walked to Jerry and sat on his lap. Jerry immediately put an arm around her neck and pulled her into an embrace. Cindy kissed him on his lips as John dealt the next hand. She kept the kiss on and even put her tongue in his mouth. Someone wolf-whistled. Jerry’s hand moved to her ass and squeezed her. She felt his cock harden in his pants and she began to move her hips on his crotch seductively.

“Pass her on Jerry, don’t hog her all to yourself,” Jack said and pulled Cindy onto his lap. He grabbed her hand and put on his already hard cock. Cindy did not even flinch. She began stroking the cock and kissed Jack at the same time while he cupped her breast. Even inside the dress she felt her nipples respond immediately. They got harder and stood up. She was feeling wetter by the minute. John smiled at his horny friends. He had something special in mind for the night.

“Well, whoever wins will get to remove a piece of clothing from Cindy’s body and she has to sit on his lap,” John said authoritatively. “Whoever is the first to fold has to lose a piece of clothing, too, and we will let Cindy do the honours.”

The round was won by John, and Henry was the first to fold. Cindy stepped in front of Henry, spread her legs and bent down from the waist. Her skirt went up to show the small black thong on her ass that Jerry smacked. She shook her booty seductively as she removed both of Henry’s shoes and his belt. She gave him a long, wet kiss as she felt his face reddening. Then as she broke it she climbed into John’s lap, facing him, and began gyrating. She allowed him to remove her hairband. There was a lot of jeering and catcalling on the table. She kissed him long and deep. The next round was won by Hardy and Jack was the first to fold.

This went on for a couple of beers at least. Cindy also made drinks for the men and served them perfectly like a maid. She didn’t mind the roleplay. As she moved around between them serving the drinks, there was a lot of incessant grabbing and cupping. They smacked her ass hard repeatedly whenever she was near enough. The guys became rowdier as they got drunk and Cindy enjoyed the attention she was getting. Being servile and obedient turned her on further. As the game went on, Cindy lost piece after piece of clothing. After her hairband, her left shoe was removed and then the right joined it on the floor. Then one after the other her gloves were removed. Cindy was already high by the time it was time to remove her stockings and she laid on the floor, lifting her legs to let Jack remove the second one and suck her toes.

Soon all Cindy had left was the frock and the tiny thong below it. Hardy won another round had the honour of disrobing Cindy. The others cheered as Hardy moved behind Cindy and planted kisses on her neck. Then he grabbed the uniform and pulled it up and over her body slowly. The dress went over her neck and then her head. Cindy now stood only in a black thong which was wet as hell. She felt cold without her clothes. The cool air gave her goose bumps and made her sensitive nipples hard. She lifted her hands and twirled around like a ballerina seductively. This was enough to set off the audience, who jeered and banged the table. She could see everyone staring hungrily at her body and she felt a surge of pleasure in her pussy. Jerry and Jack even stood up to touch her. It had been a long time since they had seen such a young and tender female body. Henry could hardly take his eyes off her completely shaven pink pussy. Jerry cupped her breasts while Jack ran a finger over her naked torso. His finger found its way down to the thong. He rubbed her pussy over the fabric, raised his wet finger to his nose and said, “This cunt is wet and ready to Kurtköy Escort be fucked!”

Cindy blushed hard. Most of the men in the room were in various stages of undressing. They had lost their shirts and some even their pants. Henry, who was the best player of the lot, was still fully dressed, except for his shoes and belt.

“Do I even need to say how high the stakes are for the next game? Raising them further, the next person will not only get to remove darling Cindy’s underwear, but will also be the lucky recipient of a blow job from Cindy,” John said. Cindy smiled, bowed low and went over to sit on Hardy’s lap. It was a tense game, and no one folded, everyone wanted to win. Cindy batted her eyelashes at everyone and cheered the players. Finally, it was between Henry and John. John had a full house and seemed like he had Henry beat, but as Henry laid down his cards, they saw he had a straight. For a second everyone was stunned and then they began banging their hands on the table and shouting.

“Henry gets to bell the cat! The sly old dog,” John said as he banged the table. He looked only a tad bit disappointed.

Cindy stood up and went over to Henry, who was blushing and nervous. She was sure of herself, though. She reached him and gave him a deep, sensuous kiss, which Henry returned tentatively at first. Soon his hands were roaming over her naked body, touching and grabbing her naked titties. His hands finally reached her thong and he put two thumbs inside on either side. Cindy grabbed his hands and removed them, then put one of hers on his head and pushed him into a kneeling position.

The guys went berserk. This girl knew how to play. They were shouting and jeering. Henry had been confused when she pulled his hands but now knew what she wanted. He bent forward, taking in a musty scent of her magical pussy. His cock was stirring in his pants. Slowly he bit into the thong and pulled it down. Ever so slowly the thong went down, exposing her ass and her pussy. Henry took it all the way down and she lightly stepped out of it. Henry could hardly believe his eyes, seeing the naked, tender and shaven pussy in front of his face. He kissed on the clit. Cindy bit her lips and rubbed her nipples, enjoying every second of it. Someone got up from the table behind her and came over. He put his hand on her naked ass and cupped it. Cindy realized it was Hardy. Then without warning he smacked her naked ass hard.

“Umm,” moaned Cindy.

The blow was hard, and it stung. Hardy who was in no mood to stop, simply raised his hand again and slapped her ass again and again. Cindy whimpered and squirmed. Hardy stopped and saw her ass turned red hot. He touched it to feel the warmth, then bent down to lick it.

“Nothing like a freshly beaten hot ass of a naughty bitch!” Hardy exclaimed.

The others joined and soon were touching her naked body wherever they could reach. Jerry began playing with her nipples.

“Fuck! This one is a real slut! She is so wet!” Jack exclaimed.

She felt many hands grabbing and pinching her titties and even more fingers rubbing her wet pussy. John put two fingers in her pussy and began stroking her soaking cunt. She was so wet they slid in and out quite easily.

“Umm… Umm… Umm… yes… yes… need more,” moaned Cindy.

He put in one more and with his thumb began rubbing her clit. With his free hand took her nipple in his mouth and began sucking on it.

“Yes sir… please… faster… faster… your slut needs to cum!”

John increased his pace and soon had Cindy humping his hand and responded with gusto.

“I’m going to cum… don’t stop… please, faster… I’m cumming!” screamed Cindy as she got her first orgasm of the night. John felt her juices flow over his hand as she fell forward, her body rocking with the pleasure of her orgasm.

She didn’t get too much rest, though. John lifted her roughly and made her kneel in front of Henry who had removed his clothes. She saw his cock in front of her face and smiled mischievously. She stared at Henry with her round eyes, holding his gaze. In front of her eyes was a large cock, fully erect. It wasn’t very long but quite thick. She licked her lips and grabbed it with her hands. She began stroking it and pressed her thumb on his tip. Henry felt amazing pleasure as the young girl stroked his cock with her soft hands. As pre-cum flowed from his cock, she slowly brought her mouth forward and stretched out her tongue to lick it. Henry shuddered with pleasure. In thirty years of marriage, his wife had never given him a blowjob and he was in bliss now. Soon Cindy slobbered over his cock and swallowed it. Though the cock was very thick, Cindy knew her job well and it was evident how good she was with it. She soon had her lips around his entire cock and bobbed her head while sucking it. She used her tongue well and soon had him squirming. Her hands found his balls and began playing with them, squeezing them and cupping them. Henry closed his eyes and felt, for the first time, a young girl’s mouth on his cock. He had no idea how amazing it could feel. Cindy was going at it as if nothing else mattered. Her tongue moved all over his cock when she took it in and then she sucked deeply as she bobbed back to give Henry a feeling of heightened ecstasy.