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  • The Submissive Babysitter Pt. 02

The Submissive Babysitter Pt. 02

12

Mei-Lin did not consider herself to be naive. At only eighteen she had already had sex, although only with two boys. Mei-Lin's boyfriend was Asian, like her. They both had very strict parents, and really had nowhere to go that was private, so they had actually not had sex very often.

After dating for several months, Mei-Lin's boyfriend had persuaded her to give him a hand-job in the movies. May heart was beating fast when she felt Winston's cock for the first time. After that May (as she was called by most of her friends and family) found herself giving him handjobs with some frequency...at the movies, at a friend's party...and one time in a stairwell of a mall. She enjoyed the illicit nature of these occasions, but of course her boyfriend wanted more.

Although Winston was very skinny and not the coolest kid in school, he was a sweet boyfriend who always took good care of May, and she was happy to please him. After a lot of pleading from Winston, May had agreed that they could make love for the first time after their prom.

The plan was for Winston to get a hotel room, but he had found them to be very expensive, and he was worried his parents would somehow find out. Winston had got the agreement of his friend Harold to use a room in his house while he threw a prom after-party.

That night, May took off her prom dress then striped completely for a boy for the first time while they could hear the drunken cheers of many other boys and girls a few feet away. Winston also stripped and for the first time she got a good look at his cock. She thought it looked nice, although it was a bit skinny, like him.

Winston was gentle and rather unsure. They kissed with their bodies pressed together until he stopped then fumbled with the condom for some time. Finally he pushed inside May who cried at first in real pain. Soon after he was done and May stared at the ceiling while he held her. When Winston got hard again later May was not sure she wanted him inside again. She started to give him a handjob, but he clearly wanted to be inside her again. May then tried to lick his cock and found that this soothed him. She didn't really know what she was doing but she could tell when he was enjoying and kept trying that. He came quickly again and May moved away to try and not get any on her.

After that night, Winston always talked about her blowjob, and how amazing it had felt. May refused to give him one in the movies because it made her too nervous not to see if anyone was watching. One night when she was babysitting for the Taylors (or Brad and Shannon, they insisted she call them by their first names), Winston kept texting, begging to come over. May finally consented, but by the time he got there she was anxious about the Taylors returning. May had told him as soon as he arrived that he needed to leave quickly, then she got on her knees and unzipped his pants. Winston was very excited and came quickly. May kept his cum in her mouth, then went to the sink to spit it out. She couldn't risk making a mess. She sent Winston on his way, and it was two more hours until Brad and Shannon came back.

As if Pandora's Box had been opened, Winston now wanted to come over every time she babysat. She refused the next time she was there, but the time after that Winston's frantic texts and Snapchats had persuaded her. He came over soon after Brad and Shannon left and they fucked on the floor. Winston was a little better than the first time, but he came very quickly, apologizing and telling May it was just to exciting to be inside her.

The third time Winston came over while May was babysitting, Brad was out of town and Shannon had a dinner with a friend. Shannon was not supposed to be back until after 10, so May told Winston to come over before 8:30. He was a little late, arriving closer to 9, and May told him it would have to be quick. He suggested a blowjob would be ideal so May compliantly got on her knees for him.

As soon as she had his cock in her mouth they heard someone at the door. May pulled away quickly, running her teeth over Winston's cock. He yelped a little as he tried to do up his fly. They both turned around to see Shannon coming in. She turned to see them as Winston had tucked his cock away, but it was very clear what they had been doing. May was mortified and started to explain, tears welling in her eyes. Shannon was rather cool about it, sending Winston on his way, then sitting May down for a talk.

May apologized again and again, and assured Shannon that her daughter was fine up in her room. May started to cry a little and Shannon stroked her hair, telling her she understood that May was a good girl and had just made a mistake in not telling Shannon she was going to have a guest over. Shannon then surprised May by asking her directly, "Do you enjoy sucking cock May?"

May stammered and tried not to answer but Shannon patiently pushed her. Finally May admitted that she enjoyed making her boyfriend happy, but wasn't sure he was good at it. As they talked May told Shannon that she studied hard to get good grades, and had practiced many hours to become good at piano, but wasn't sure how to know if she was good at blowjobs.

Shannon smiled and stroked May's hair again. She then gently asked May to show her how she did it. May was confused, then watched Shannon hold out a finger in front of her face. May hesitated a moment, but decided she trusted Shannon and didn't want to let her down again. Besides, she genuinely would appreciate any advice. May sucked on Shannon's finger tentatively at first, then with more enthusiasm. She imagined it was Winston's cock and jerked her head up and down.

Shannon waited, then finally pulled her finger away.

"You are obviously eager," Shannon stated, "but you need a bit more finesse."

Shannon patiently showed May how she suggested a cock should be sucked by sucking on two of May's fingers. May felt the softness of Shannon's tongue and how it slowly explored her fingers. She felt a warm tingle across her body and thought to herself that if it felt this good on her hand it must feel great for a guy on his cock. She then emulated Shannon the best she could until Shannon told her she had the right idea. May felt proud to have improved and was thinking how pleased Winston would be.

Shannon put and hand on May's chin and softly lifted her head so May was looking up into Shannon's eyes. May thought for a moment that Shannon was going to kiss her and wondered how it would feel to have soft lips on hers. Instead Shannon gently scolded May again for having a guest over without letting her know first. May started to look down in shame, but Shannon jerked her head back up so May was looking her in the eyes.

"If you are going to have a boy over you need to let me know. I need to trust that you will always do as I tell you to May."

May nodded, a little uncertain as to what she was agreeing to but genuinely wanting to please. "I promise Shannon."

It was over a week until Shannon called May to have her babysit again. When May saw Shannon's name come up on her phone her heartbeat accelerated. May had been thinking of Shannon a lot since she had been caught that night. Alone and looking at her phone she blushed as she remembered she had actually masturbated thinking at first about Winston, but then about Shannon and her tongue...how she had stared May directly in the eyes as she had licked May's fingers. When May answered Shannon told May she needed her to babysit that Saturday for them. May agreed without even thinking. She was clearly anxious to please. Shannon told her the time to be there then asked if she had seen her boyfriend since they had talked.

May remembered she had in fact seen Winston the night after they were caught. She was anxious to show her boyfriend what she had learned so she shocked him by going down on him that night in the movie theater. Unfortunately, Winston was so excited by the surprise and May's new technique that he came after less than 60 seconds. May was proud, but also disappointed. She tried to swallow, as Shannon had told her to do, but couldn't bring herself to do so, instead spitting it out on the theater floor.

"Yes..." May stammered. "It...umm...worked very well, thank you."

Shannon laughed and told May it would only get better, she just needed more experience. She left May with an unexpected instruction, "Wear that yellow sundress you have, you look very pretty in it." That night May, who masturbated very rarely, told Winston she had to study, but instead took a bath where she fingered herself to an orgasm thinking about sucking a big cock...but mostly about Shannon.

When May came to babysit, Shannon gave her a warm hung and kissed her on the lips. It wasn't the kiss that May had imagined though, just a friendly, flirty one. May did notice that it was very different to kiss soft lips. Shannon remarked how pretty May looked in her sundress and when Brad came out she had him confirm how pretty May looked. Shannon gave the normal directions about caring for their daughter, who was already in bed, holding May's hand while she talked. She also asked May to take care of the dishes they had left from lunch. When they were ready to leave Brad said goodnight and Shannon gave May another quick kiss, then whispered "No boys tonight May."

When May was alone in the house she let out a deep sigh. She wondered why she was having all these thoughts about Shannon. She knew she was not a lesbian. She had never thought about women like that...until Shannon. But even then, it wasn't like she wanted to go down on Shannon, and she didn't want Shannon to lick her pussy...although she had to admit she had wondered what that would feel like. May felt a little dizzy, but got to work on the dishes. She saw a beef jerky snack box on the counter and thought about Brad. She had always thought Brad was handsome. He was so different than her boyfriend. Obviously they were different races, but Brad was fit, even muscular, while Winston was very skinny. Brad had hairy arms and chest, where Winston had almost no hair at all. May thought of the few hairs Winston had around his penis and wondered what Brad's looked like. Brad also had a sort of...stature that Winston lacked. After all, May thought, Brad is a man and Winston is still a boy.

May smiled as she remembered how Brad had looked her up and down when Shannon had asked him to tell May how pretty she was. May knew when men found her attractive, and as polite as Brad was, he clearly noticed her when she wore something nice. She giggled to herself thinking of how lucky Brad must be to get blowjobs from Shannon who is so pretty and seemed to good at it. She felt a tingle in her body and tried to think about something else.

May went on the clean the entire kitchen, then fold some laundry she found in the dryer. She knew Shannon would be impressed when they got back. When they did return May brightened as Shannon told her what a good babysitter she was for doing all the chores. Brad ordered a car for her and while they waited Shannon sat close to May, their legs touching as they talked about her plans for college. May found herself a little flustered by Shannon's proximity and wondered again why Shannon has such an effect on her. She was a beautiful woman with such smooth white skin and bright red lips...but May had seen other women just as beautiful. When Shannon reached over for May's hand, May squeezed back, gratefully.

Brad came in, saying the May's car had arrived. Shannon said goodbye and kissed May on the lips. May closed her eyes as Shannon's lips met hers, but it was too quick again. Shannon told May to come back next Friday, as Brad and her had a party to go to. Brad saw her to the Uber he had ordered and before she got in May surprised herself by kissing him on the cheek, something she had never done before. On the ride back, May did something else she had never done, putting a finger inside herself in public. She stopped quickly when she realized how inappropriate it was, and looked up to confirm the driver had not seen anything. She told herself she needed to get it together.

By the time the following Friday came along, May had found herself daydreaming about Shannon and Brad more and more. When she kissed Winston, she thought about how much softer and gentler Shannon's kisses were. When she gave Winston a handjob at the movies she imagined how much bigger Brad's cock must be. Brad's hands were huge, she thought as Winston spurted on to the seat ahead of him and the floor.

When the Friday finally came, May put on a couple of outfits and looked at herself in the mirror. She knew Shannon noticed what she wore and wanted to look her best. She settled on a pair of jeans she always got compliments in (they hugged her ass nicely), and a white shirt that complimented her small breasts. Before leaving she unbuttoned one more button than she usually did, and smiled.

When she arrived at the Taylors, Brad and Shannon were a little rushed. Brad had written down the wrong time for the party and they were already late. Shannon seemed full of energy but did not spend time with May. Instead May watched as she rushed about. She noticed Shannon was showing off her legs in a skirt that was shorter than any May owned.

Brad and Shannon rushed out the door and May did not even get a kiss. May took their daughter Nancy up for a bath and got her to sleep, then did a few chores. While she was making their bed she stopped and smelled the sheets. Shannon's scent was in them and May thought again about how feminine Shannon was. She hoped she would develop into a woman like Shannon. She received another text from Winston and texted back telling him again that he could not come over. As she wrote back she received a text from Shannon,

'May, having fun time out, need you to stay later. We'll spend some time when we get back."

May smiled and read the text again. She liked that Shannon had become a friend and texted back assuring Shannon that she would stay as late as needed.

When Shannon and Brad finally did return, it was immediately apparent both had had a lot to drink. May started to tell them about the baby but Shannon interrupted, giving May a long hug and kissing her again on the lips. May enjoyed feeling Shannon's embrace and felt a strange combination of ease and excitement.

Brad seemed a little out of it. He gave May cash with a nice tip, and said he would call her a car, but he never made a move to do so. Shannon then suggested they have another round of drinks and invited May to join them. May hesitated. She had only drank alcohol one other time, at a party. May had learned that she got drunk easily, and found that her judgement became impaired. In fact it was at that party that she was fucked by the only boy other than Winston she had ever had sex with. It was actually at WInston's friend's Harold's house a few weeks after the prom party. They had all been drinking early and Winston passed out on a couch. Harold had a fight with his girlfriend who had left in a huff so May and Harold were hanging out. Harold took May up to his room to show her his collection of anime t-shirts, but when they got to his room Harold told May how beautiful she was and kissed her. They made out a while and eventually Harold had unbuttoned May's short and was sucking on her nipples. May lost herself in the sensation. Winston did not pay a lot of attention to her tits and it felt so good. Soon she found her pants being pulled down and Harold's tongue licking her pussy. May had never experienced this and even though she knew she should tell Harold to stop she couldn't bring herself to do so. May closed her eyes and let the sensations run through her. When Harold positioned her on all fours, May felt she had gone too far to stop things. Harold pushed into her from behind and fucked her harder than Winston had, slapping her ass cheeks with each thrust. The next day Harold and May agreed never to tell anyone about this and May still felt bad about the indiscretion.

Despite her misgivings, May could not say no to Shannon, and soon enough they were drinking vodka tonics as they chatted in the living room. After nervously downing her first drink May could already feel her cheeks flush. She knew she was staring at Shannon's legs too much, but felt like she couldn't stop herself. When Shannon asked her to rub her feet, May was actually excited to do so. She finished her second drink and knelt before Shannon, who was cuddling her husband on the couch.

Shannon seemed to tease May a little, wiggling her foot while May tried to take in it her hand, but when May did start to rub Shannon laid back and moaned softly. May was happy to see her so pleased.

May could feel both Shannon and Brad looking at her as she rubbed Shannon's feet and the tension made her a little wet. May tried to focus on Shannon's foot even while she heard the shuffling on the couple's hands exploring each other. She tried to be cool, but feeling the warmth of Shannon against her, seeing her bare long legs inches away, and hearing the two of them touch each other all made her take shallow breaths. She hoped they wouldn't notice but Shannon suddenly said, "Mmm...somebody is excited."

May started to blush then she heard Shannon say, "May, look at how excited Mr. Taylor is."

May looked up to see Shannon holding her husband's hard cock through his pants.. May blushed and looked back down at Shannon's feet but squirmed from the excitement and uncertainty around what was happening.

"Don't be shy May...feel it" Shannon instructed. "I bet it's bigger than your boyfriend's."

May was mortified to have Shannon talk like this in front of Brad, but she was also intrigued. She looked up again and Shannon grabbed May's hand and placed it on her husband's cock. May felt paralyzed, holding Brad's cock through his pants with May's hand around hers. Shannon squeezed and May felt Brad's cock pulse.

"Is it bigger than your boyfriend's" Shannon asked teasingly. May could not find words but nodded as she continued to stare at the tent in Brad's pants.

"Show her you cock honey." Shannon coaxed her husband. "May should see for herself."

May's heart pounded as she watched Brad unzip his pants clumsily, and pull out a big, hard cock. May watched Shannon stroke it, noting her technique. Shannon then took May's hand, placed it on her husband's exposed cock and together they stroked Brad up and down. May saw Shannon smirk down at her and she nervously giggled. When Shannon took her hand away to stroke May's hair May continued to stroke Brad's cock slowly, the way Shannon had been doing.

"That's a good girl." Shannon purred. May's young face brightened as she continued to stroke. She was amazed at how big and white it was, and by how much hair he had around it.

"Why don't you suck his cock May?", Shannon asked.

May pulled her hand away from Brad's cock suddenly and stammered, "I...I can't Mrs. Taylor." She wasn't sure why she addressed Shannon so formally, feeling like a little kid. "I mean I..."

Shannon became firm, "May, remember when I came home a few weeks ago and you had your boyfriend here?"

May was ashamed to be called out in front of Brad and nodded slowly.

"Did you suck his cock in this house May? Tell the truth."

May bit her lip, then nodded slowly, her eyes down as she remained kneeling.

"Don't you think it's disrespectful to suck another boy's cock in a man's house, then refuse to suck his when it's right in front of you?"

May knew she was drunk, but struggled to follow Shannon's logic. She looked again at Brad's hard cock, which looked sad just lying there.

"Go on May, you can do it." Shannon instructed soothingly, stroking May's hair.

May felt a sense of comfort when Shannon stroked her hair and realized that she didn't want to disappoint her. She actually wanted to show Shannon she had learned well, and wanted to see for herself how good she was with a man who would not cum as quickly. She moved between Brad's legs took his cock in her hand, and slowly took it in her mouth. She was shy at first, and a little intimidate by its' size, so she licked around his cock. Finally she started to take him deeper and deeper into her mouth using her tongue as Shannon had taught her. May looked up at Shannon as she bobbed her head up and down along his cock and basked in her approval.

12
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