Lollipop was a bubbly teen girl who had just celebrated her eighteenth birthday in early December and the best present her high school could give her was Christmas break. She couldn't wait for the two week vacation since school wasn't going very well for her. She wasn't too smart and was all ready held back twice so that she was still a junior. Her lack of academic skill didn't impede on her popularity one bit. She was a blue eyed beauty with golden blonde hair hanging down to her shoulders. She also had the biggest breasts in the school, her chest size in the double D's. She loved to wear tight t-shirts to tease all the boys. Her favorite t-shirt was a pink one with "cum lover" in glittered letters on the front and "90 degree angle" with an arrow pointing down to her perfect little shapely ass on the back.
Despite her enjoyment of dressing in sexy outfits and wearing nasty little t-shirts she was still a virgin. She however did love to tease, flirt and lead guys on. Often she pretended to be a little slut but wouldn't even allow guys to touch her. Leading guys on was an exciting practice for her, especially guys who might not take no for an answer. Her nickname came from one of the methods she would do this to the poor boys. She liked to carry a long, spiral lollipop into class and lick and suck on it in front of them. Sometimes even moaning as she did it. No one was the object of more masturbation fantasies than her.
So it was on the last day of school before Christmas break that she was strutting through the hall wearing her favorite t-shirt and a pair of tight, faded jeans. Her lips, in sparkling lip stick, curled up into a smile as she passed by a group of boys. She didn't have to look back, she could feel their eyes following her. Her strutting however came to an abrupt stop when Mr. Long the school principle appeared in front of her, seemingly out of thing air. He had a knack for doing that, something that led to speculation among students he may not have been from this world. He stood over her, his balding grey hair in a bad comb over and his thick brown rimmed glasses staring down at her.
"Little miss what did I tell you about wearing that t-shirt to school? It is obscene and I'll have none of it. You'll have to change in my office." Mr. Long said crossing his arms over chest.
Lollipop looked up at him with her best puppy dog eyes biting her bottom lip. "Oh, Mr. Long," she said in a cute little voice. "I know you said you'd suspend me, but can I help being a naughty 'wittle' girl?"
Mr. Long didn't seem to be effected, even when she puffed her chest out a bit. "We'll discuss your suspension later, but for now you will have to change that obscene shirt. Go to my office and change now. My secretary Miss Parker will give you a shirt to wear."
After stomping her foot Lollipop submitted to his authority and stormed off to the administration building as told. Inside the building sat the desk of Miss Parker, a forty five year old divorcee who still retained her lovely shape of body. Her brunette hair tied up and wearing glasses she was the only woman, student or faculty, that had breasts as plentiful as Lollipop. Like Lollipop, Miss Parker was the fan of attention from the boys as well, often wearing tight fitting long skirts and jackets and blouses that showed plenty of cleavage.
Miss Parker spoke with a soft and sexy voice, but didn't need to use it when she saw Lollipop walk in with her "cum lover" shirt on. Miss Parker opened a drawer in her desk and took out a plain white t-shirt, the last one left. She tossed it to Lollipop and pointed to the principals office door. Giving a defiant huff Lollipop stormed into the office and slammed the door shut as hard as she could and stood alone in the principals office.
She tossed the t-shirt onto the desk and looked about the office for a minute deciding this was a good excuse to be late for first period. Everything was neat, tidy and in perfect order. There didn't seem to be a spec of dust anywhere, and even the trash was sorted into several different little bins. She slid off her dirty t-shirt and stuffed it into her book bag. She then realized that she probably should have worn a bra that day. Taking the white t-shirt Miss Parker had given her she pulled it over her head stretching it past her chest, being too small it only came down to the top of her stomach.
Unexpectedly, the door opened and Miss Parker walked in. Lollipop turned around facing her, a look of confusion on her face. Miss Parker just smiled and closed the door behind her and then locked it. It was then that Lollipop noticed a leather paddle in her hand. A bit shocked she took a step back while Miss Parker gave her a sexy little smirk.
"Mr. Long may have forgotten, but one more suspension and you will be expelled. It's in your file you know." Miss Parker said. "You don't want that do you?"
"Oh no!" Lollipop exclaimed. "You see if I get expelled or flunked one more time, my parents are going to send me to live with my uncle in Nebraska. They don't know it, but he's a dirty pervert and would do dirty things to me!"
"Ooh," Miss Parker whispered. "The thought of a dirty old man doing dirty things to your young flesh sends a tingle up my thighs. However, I'm sure its complete dread for you little dear. Lets make a deal. If you do me a very special favor, I'll convince Mr. Long not to write you up."
Lollipop thought for a moment, but then agreed. "Oh yes Miss Parker" she said, "I'll do anything."
