Cindy's Playtime - Cover

Cindy's Playtime

Copyright© 2021 by Tony Sorrentino

Chapter 2

Coming of Age Sex Story: Chapter 2 - Cindy just wanted to have fun. She knew her grandmother wanted her to be a good girl but it was so much fun being bad and she liked the way it made her tingle down there where it felt so nice. Her new friend Betty showed her how to be bad and they were soon best friends forever. Now she was learning all about sex and it seemed to her that she had to be quite bad in order to be a good little girl.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/ft   ft/ft   Teenagers   Consensual   BiSexual   Heterosexual   Fiction   Anal Sex   Cream Pie   Exhibitionism   First   Masturbation   Oral Sex   Petting   Squirting   Voyeurism   Nudism  

Cindy waited under the awning outside the movie theater hoping that her skirt was not too short because all the males were staring at her like she was a Japanese play doll looking for action.

Unfortunately, Betty was not with her today despite her promise to be there no matter what.

She had counted on having Betty as her wing-woman to keep things interesting with her older man date. Their previous encounter was clear in her memory, and she used her visual thoughts to spur her masturbation efforts each and every night like clockwork to get her juices flowing hot and spicy between her teenaged legs under the covers masking her frenzied humping of her favorite teddy bear called “Mark” which just so happened to be the older gentleman’s name as well.

They had taken Mark home to her grandmother’s house where he had anally satisfied them both with his oversexed cock spanking them nicely at the same time. He had told them that he was happily married but was obsessed with young girls and he was anally fixated on teenaged bottoms above all else.

Cindy knew she had started the whole sordid affair with her ass-teasing ways using her cherry red thong to excite the male glances up her skirt. It made her feel super bad to tempt the men that way and she liked it when they spanked her for her naughty actions. She had her best friend forever Betty to push her into sexy situations and they had formed a close relationship that would have shocked her grandmother if she ever suspected what they did during their sleepovers.

She remembered how Betty had used her pointed pink tongue to lick away Mark’s spunk from her fully stretched brown eye as the older, married man pounded her buttocks mercilessly from behind like a person possessed by a demon inside him.

The very thought was enough to prompt her feminine folds to leak sticky teardrops of pleasure juices into her clean white panties. She hoped they would not stain them with telltale evidence before Mark had a chance to excite her clitoris with his playful tongue in the darkened theater.

Betty had informed her only late this afternoon that she had the “Flu” and would be unable to go to the movie with her. Cindy knew Betty was telling the truth because she knew the girl well enough to know she wanted Mark’s cock inside her with the desperation of a lonely teenaged girl in need of male hardness between her legs. She hoped that she had not caught anything from her best friend Betty because they had a sleepover only two days ago doing endless “sixty-nine” with loving tongues and busy fingers. It was not as nice as sharing a willing cock like Mark’s, but it was enough to keep them both fit for loving and sated with the spending of their juices throughout the nocturnal hours. The taste of Betty’s pussy juices was exactly the thing she needed to keep her fires of lust motivated to seek out cock, cock and more cock with her pandora’s box of female pleasure ready and willing to dispense her sexual favors to any male with enough nerve to act on his impulse to penetrate her sexy body.

Today, at school, she had been sent to the vice principal’s office for leaving her chewing gum all over her desk in homeroom and she had to explain that she was addicted to the stuff because she loved the feeling of the bubble gum inside her mouth. The female vice principal was called Mrs. Robinson and she was quite chunky with an ass that overflowed over the edge of her wide chair. Cindy knew Mrs. Robinson was in the process of a divorce with a cheating husband caught with underaged girls.

Mrs. Robinson whose Christian name was Dolly had become downright nasty toward the young female students under her control and she was becoming much stricter with her discipline with them even for minor infractions of the rules and regulations of the school.

“Cindy, you must stop this silly business of the chewing gum!”

Cindy knew the woman was agitated and she felt nervous because she had done many things far worse than the chewing gum and she was fearful that Mrs. Robinson would discover her hidden secrets when it came to attracting male attentions.

“I promise to be a good girl in future, Mrs. Robinson” she replied uncrossing her legs and showing the older woman her pretty, white panties beneath her short uniform skirt. She saw that the older woman was incensed at her display, and she played with her strands of loose hair pretending to be totally clueless about her sexy display.

“I must punish you for your carelessness, Cindy. Stand up and bend over my desk with your skirt up high around your waist.”

Cindy jumped up quickly knowing that the woman was intent on spanking her bottom pretending she was one of the girls her husband had been humping behind her back. It surprised her when the older woman yanked down her white panties exposing her not so innocent buttocks to full view. She felt the woman pass her palms across her cheeks with the intent of making her humiliated at the touch.

Then, the spanking started.

It was a lot more intense then ever before. Cindy knew Mrs. Robinson imagined her to be one of her husband’s many teenaged lovers.

“Oh, please, Mrs. Robinson, not so hard. I promise to be a good girl. I will not bend over for any man until I get married.”

The older woman just hit her buttocks harder and caused them to be reddened with the mark of the punishment.

Eventually, Cindy’s tears flowed copiously down to the desk below wetting the teacher’s papers with her salty tears. The teacher even mounted the young girl’s buttocks and shoved her thick blunt marking pen up between her cheeks and inside her tightly clenched sphincter.

“Oh, Mrs. Robinson, whatever are you doing to me back there? I like it even though it hurts a little. Please don’t stop, it makes me feel good to be so bad and I will do whatever you want no matter how humiliating.”

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