Lollipop Under the Christmas Tree

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."

"Good girl. I'll need you on Christmas Day, and you can do my favor. However that doesn't mean you shouldn't be punished. Be a good girl and drop your jeans and panties and bend over the desk."

Lollipop gasped unsure of what she should do. But the thought of living in Nebraska bent her will to obey. She unbuttoned her jeans and slid them down slowly. She felt the eyes of Miss Parker, staring at her creamy thighs. Turning around, her face red with embarrassment, Lollipop then pulled down her panties exposing herself to the secretary. She leaned over the desk, resting on her elbows and forearms and waited.

Bent over and vulnerable, Lollipop felt Miss Parker's slender hand run along the curve of her ass. Miss Parker was stroking it with a gentle caress before taking away her hand, and delivering the first spank across her milky backside. Lollipop cried out looking back over her shoulder at Miss Parker's orgasmic delight as she spanked her little ass again. Not being able to watch any long Lollipop looked ahead as she felt the third smack of the leather paddle on her rear end, now a rosy red coloration.

"Now about that favor," Miss Parker said before the fourth spank. "There is a boy about your age named Lewis. Poor Lewis is a bit of geek I'm afraid and none of his classmates like him. Since he was going to be alone on Christmas I told him I was going to give him a very special present. I was going to give myself but you'll be much better. Meet me on the corner of Elk and Oak street at six in the morning, Christmas day. If you don't show up or are late, consider yourself expelled. Understood?"

"Yes Miss Parker." Lollipop answered.

"Oh please dear, call me Mistress."

Once again Lollipop found herself confused, but soon enough told Miss Parker "yes Mistress."

Miss Parker smiled and gave Lollipop the fifth and hardest spank yet. Deciding that was enough Miss Parker leaned down and rubbed her nose softly against Lollipop's virgin pussy. After inhaling the scent Miss Parker bent over the girl and whispered in her ear, "I love the smell of cherry in the morning. See you Christmas morning dear."

~

A fresh snow had fallen over Christmas Eve and now laid sparkling in the rising morning sun. Lollipop dressed warmly stood by a stop sign on the corner of Elm and Oak street where she was supposed to meet Miss Parker. She hadn't been waiting long when Miss Parker's car drove and stopped next to her. Lollipop quickly got into the passenger's side relishing the warmth coming from the heating system. Miss Parker drove down Oak Street for a while before turning into the driveway of a mid-sized blue house.

Both of them getting out of the car Miss Parker fumbled through a large bag finding a set of keys. She unlocked the front door and let herself in, motioning for Lollipop to follow, which she did. The house was small and could have used a bit of cleaning but the heat was on and that was all that mattered to Lollipop after standing in the cold for a while. Miss Parker led her into the living room, a small room with a television and a couch. In the corner was an artificial Christmas tree, poorly put together and poorer still was how it was decorated. There were no presents under it.

"Now" Miss Parker whispered. "Remember to keep quiet. We don't want Lewis to wake up before Mrs. Claus can deliver his present now do we?"

Lollipop shook her head no.

"Good," Miss Parker continued. "Now strip down naked. Take all your clothes off and put them in this bag." Miss Parker reached into the bag pulling out a nightie and a red ribbon. "Hurry up now, Lewis is an early waker."

Lollipop did as she was told quickly stripping down in front of the groping eyes of the Mistress. She put all her clothes in the bag as instructed and when handed the nightie she slipped it on. It was white with a cherry design on it. Miss Parker set the bag aside and fixed up Lollipop's hair into pigtails. She then guided Lollipop to the Christmas tree who promptly laid down under it. Miss Parker then tied the ribbon around the waist of Lollipop into a big bow and laid a little card on her.

"Now don't move from this spot until Lewis comes in and sees you. You're going to do whatever he wants, and if he isn't the happiest young man in the world before noon, you're in trouble." Miss Parker smiled and walked away. She picked up the bag and then left the house and drove away. Lollipop laid there perfectly still waiting for Lewis to show up. She was nervous, she actually had her hymen broken in a bicycle accident when she was younger but was this the first time she had ever done anything. She knew the Lewis Miss Parker was doing this for and what a painfully shy person he was. She wanted to think of something good to say to entice him.

Amazed by how turned on she was by all of this Lollipop's nervousness turned to anticipation. She bit her bottom lip, waiting ever so patiently careful not to move. Her heart started to race when in walked into the room Lewis. He skinny but tall young man, his dark hair was in a mess and he was still in his white undershorts and boxers when he came in and saw Lollipop laying under his tree. Lewis nearly panicked, not sure of what to make what he saw. He slowly made his way over to the tree and picked up the card laying on Lollipop.

"Merry Christmas to a sweet young man named Lewis, Miss Parker." It read.

Lewis took a few steps back lost in wonder. After taking a deep breath and collecting himself he leaned over and pulled loose the ribbon. With a playful smirk Lollipop got up onto her knees slowly spreading her thighs apart. She lifted the nightie up ever so slowly, revealing herself to the watchful eyes of the young man. Her fingers then ran down her stomach to her snatch and opened up her pussy for his viewing pleasure.

"Lewis," Lollipop groaned out. "I have a cherry that needs popping, can you help?"

Lewis was unable to speak, he just stared at her in a daze and nodded his head yes. Lollipop pulled the nightie off revealing the rest of her perfect body to him. Licking her lips she crawled to him on all fours and purred like a kitten as she rubbed her cheek against his thigh. She ran her hands up his legs and grabbed at the waistband of his boxer shorts.

"I want to see the cock you're going to shove into me." She groaned out pulling his boxers down. Startled she fell back and gasped. Her eyes widened, a tint of fear in them as she stared at the giant swinging between Lewis' legs. She had no idea they could be that big. It was even bigger than in that porn movie she once watched with her friend Mandy. She got back up to her knees unable to take her eyes off it. She reached up and grabbed it, unable to get her fingers all the way around. As she touched the giant, it grew hard and stood up and grew a bit bigger. Her jaw dropped unsure of how she was going to be able to fit it into her. While her mouth was open Lewis had grabbed the back of her head and stuffed it into her mouth.

Only the head and a bit of the shaft was able to fit in. Who knew a geek would have such a monster in his pants? Lollipop pulled her head away coughing and gagging but Lewis pulled her head right back to him. Only able to oblige Lollipop opened her mouth and took as much of him into her mouth as she possibly could. Her head bobbed back and forth as she sucked away furiously. Her saliva slobbered all over the head and dripped down her chin and she had to use both hands to stroke his shaft. She prayed he didn't cum right away as it would no doubt be like turning on a fire hose in her mouth.

She managed to pull her face back a bit and then gasped out, "sit on the couch."

Lewis went over and sat on the couch while Lollipop crawled over to him. Squeezing her breasts around his cock she began to work his shaft with her tits. Lewis leaned his head back and closed his eyes as she bounced her tits up and down on his spire of flesh. She let out heavy gasped moving her chest up and down on him just like how she saw in the movie. Lewis opened his eyes and looked down at her. From his look, Lollipop knew what was coming next.

Lollipop turned around and got down on her hands and knees. Looking over her shoulder she watched Lewis get off the couch and move behind her. She whimpered a bit and then took a deep breath waiting for it. Lewis grabbed her hips and slowly pushed that monster cock into her pussy. Lollipop screamed as she felt herself stretched open. Tears welled up in her eyes while Lewis pushed himself deep into her. "Oh God! It's so big!" she screamed out as Lewis slid it back and forth slowly in her.

Lewis grabbed her pigtails pulling her head up back. Lollipop's poor defenseless pussy was being assaulted. He drilled it into her hard pounding his hips into her and Lollipop loved every moment of it. Each thrust was met with a scream of ecstasy from her. Her arms gone weak she fell to the floor on her face her ass in the air while she was getting the fucking of a lifetime. Her face was red from all of her screaming and howling as well as the heat from her body.

Getting winded Lewis pulled out and sat back against the couch. Lollipop however, wanted more. She turned and pounced on top of the young man and impaled her self on him. Her tits rubbing in his face Lollipop bounced on his cock, her dripping pussy wetting the stiff meat so it slid up and down easier. Lewis was groping and sucking at her breasts while Lollipop rode him, grinding herself into him as fast as she could. Her eyes rolled up and she turned into a fucking machine, wanting nothing but to continue getting stuffed like a Thanksgiving turkey.

Lewis got up lifting Lollipop who was still driving her hips into him. He moved to a wall, wanting to pin her and fuck her against it. After slipping though, they both fell into the tree. That didn't bother Lollipop at all as she put her hands over head and grabbed hold of the tree. Her legs over both of Lewis' shoulders and him holding her by the back of her thighs. Lollipop now a tree ornament continued to get nailed by Lewis' monster. She had lost her voice and breath long ago and just floated in her senses. She felt Lewis pull out of her again. Lollipop looked down just in time to see the cum shoot out of his dick like a geyser spraying it all over her stomach and breasts. Lollipop just sort of crumbled to the floor in exhaustion looking like wrapping paper torn from a present. Lewis pretty much did the same. Lying under the Christmas tree Lollipop managed to hear Lewis, through his wheezing, say the words:

"Best. Christmas. Ever."