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Jessica claims she was a wallflower in high school but has blossomed into a congenial beauty. ?I?m a down to earth prairie girl?warm-hearted and sweet,? she says, ?but I also have a very spicy side when the time is r?

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When Billy oversleeps and arrives to class in his pjs, he gets scolded by his bossy and busty school teacher Mrs. Stacie Starr who forces him to cum twice

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Maddy is awaiting Bill to to take her to the airport when she finally hears a knock at the door. Bill asks why his sister wasn\'t the one to see her off since they are best friends. Maddy tells Bill that his sister has her finals for school and couldn\'t make it. Maddy is ready to go but, Bill tells her she has loads of time and that they should just relax in the house. Bill has had a crush on Maddy for a while, he realizes that she won\'t be coming back for some time and this is his last chance to let her know how he feels! When he tells her she lets him know that she had a crush on him too though, she never did anything about it because she didn\'t want it to be a weird situation around his sister. Well, his sister isn\'t around, and she\'s leaving for the semester! They skip to the courtship and get straight down to business!

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I am a huge fan of Kennedy Leigh\'s work. So when I found out we were both in the same city at the same time I had her agency send her over to my room. I\'ve always had this fantasy where I get to be the Principal of a school and I get to punish a naughty schoolgirl for acting up in class. Today I get to live out that fantasy with Kennedy.

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"""I\'m pretty darn competitive and love a good challenge,"" says courtney. An All-State track star in high school, she\'s now a nursing student and goes for athletic guys with manners?"

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?It wasn?t until my senior year in high school that I started to blossom into a woman,? Anna admits. ?Now it?s so funny, because all the boys who made fun of me for being flat-chested are lining up to date me or just?

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India Summer went back to school after not attending for years. I guess you could say that makes her the cougar of the classroom and she\'s definitely on the prowl. She invites the teacher\'s aide, Bill, over to her place because she needs help studying. She just gets so distracted in class. School is hard for India, but only because she\'s too busy thinking about taking Bill\'s hard cock in her pussy. Once she has Bill alone in her bedroom this cougar pounces on him. Bill will never forget his first time seduced by a cougar.

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"""They call me \'Star,\'"" says Pamela Zinszer. ""Why?"" we ask her. ""Have you ever starred in anything?"" ""Oh, I acted a lot in high school."" ""In what roles?"" ""Mostly in trying to stay out of trouble."" We try another tack.?"

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I don\'t normally do these kinds of things, but I just made tons of extra cash on sports and decided to celebrate. I\'ve always been a fan of Tasha Reign and scenes with her hot school girl outfit so I decided the best way to spend some of my winnings is by having her drop by my hotel in that outfit. She looked so hot in it and even better with my cum all over her face. Money well spent.

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"""I once had to write an essay titled \'Why I Love Lenin More Than My Mother,\'"" Victoria Nika Zdrok says, recalling one of her grade school assignments in the Ukraine. ""In kindergarten we learned little poems about Len?"

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Sara Jay can\'t wait until her son leaves for school in the morning so she can have some alone time. The first thing she does once he leaves is pops out her trusty vibrator and starts going to town on herself in the living room. Unbeknownst to her, her son\'s friend, Tyler, was spending the night and is still lurking around the house. Tyler walks in on Sara playing with herself. Sara decides the real thing is far better than her vibrator and strips Tyler down so she can take his hot cock in her wet pussy.

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Alura Jenson & Ava Addams have had enough of Johnny\'s shenanigans, but they made a promise to his parents that they would help Johnny out at school. They have finally had enough and think Johnny should repay them for all they put up with, so they have him repay them with his cock.

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"When the Los Gatos High School newspaper asked students where they wanted to be in ten years, Carrie Jean Yazel, class of \'88, answered, ""In the pages of Playboy."" Seven years ahead of schedule, Miss May comes to u?"

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When Debbie Davis was graduated from Burbank\'s John Burroughs High School, she wasn\'t sure what she wanted to do. She toyed with a couple of fairly promising choices: going to college or becoming a stewardess. But wh?

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"Smart, artistic and beautiful, Alina Novozilova is the definition of a digital age renaissance woman. Born in Estonia, she attended art school there (""I love to draw""), got her degree and then decided to emigrate to?"

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"Our Cyber Girl for July 9, Samantha Speer, told us she\'s not only a ""killer horseback rider,"" but she\'s also attending culinary school. ""One day my Dad and I are going to run a restaurant together"" She added, ""I\'m ar?"

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"Think your school library is boring? Transfer to Mizzou, where babes like Lauren Albrecht hang out in the stacks. ""All of my time is spent there studying and reading novels,"" Lauren told Playboy.com. Her favorite aut?"

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A couple of years ago, Marilyn Lange (it rhymes with tang) was back in her native New Jersey and going to secretarial school. Pretty blah. Then, on a whim, she went to Hawaii - via a tour - and stopped at Waikiki, wh?

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Jessy is up to to no good. He got the urge to fap while at school and had the smart idea of doing it in the teacher\'s bathroom. His hot teacher, Romi Rain, catches him and has him report to her classroom immediately. Well, the only reason Jessy was fapping is because he can\'t stop thinking about how hot Romi is! That doesn\'t get Jessy out of hot water though. You see, Jessy is on a student visa and if word of his bathroom escapades got out he would easily be sent back. Romi doesn\'t want him to get kicked out, so she\'s willing to work with him. She wants him to show her exactly what he was doing in the bathroom. Jessy drops trou and begins masturbating for Romi, but Romi thinks she can do better. She takes a hold of his cock and doesn\'t let go until he fucks her pussy good and comes all over her pretty face.

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Check out the delicious repercusions of violating school policy.

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When Alex\'s parents won\'t pay for college, he goes to Financial Aid to see if Ms. Lisa DeMarco can help him pay his way through art school. She knows they can figure something out about a scholarship, especially after she sees his skills and the size of his paintbrush.

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Ofelya is just your typical 18-year-old parochial school girl. Her current fuck buddy Bobby begged her to put on her jumper for some extra naughty and plaid staining fun. Ofelya took it up a notch and pulled her hair into pigtails and really plays up the fantasy for her very lucky stud.

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A former student, a stewardess and a Sunday-school teacher?imagine these three girls next door. From the February 1981 issue of Playboy magazine.?

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SCHOOLMATE PLAYMATE Miss January is a bouncy teenager Reading and writing and \'rithmetic are the subjects that occupy button-bright Elizabeth Ann Roberts -- a student in her teens -- even though most other girls h?

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I used to be a real nerd in high school, but I\'ve changed a lot since then. I\'m also worth a lot more money after I sold the company I helped start. Now, I can afford anything I want, and after I found out that one of my old teachers was a porn star I knew I had to have her. I always had a crush on her and would day dream about the things I wanted to do to her. So I have her agent send her to my hotel room. Of course, she doesn\'t recognize me at first, but soon remembers once I put on my old glasses. Tonight, I get to be a bad boy, and my old teacher gets to punish me the way I always wanted her to.

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Johnny has been working really hard to get his Master\'s degree. His hot girlfriend has always been supportive and proud of him. To show him how proud she is, she gets him an early graduation gift. Another hot girl for him to fuck. Looks like it really does pay to stay in school.

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