All characters depicted as participating i sexual activity are over 18.
Part 1
Pretty but smart?
Tiffany went by Tippy, she decided this because it was classier than Tiffany or Tiff or Tiffy (shudder). When she was little she saw the movie 'The Birds" and while it terrified her she thought Tippy Hedren was the most beautiful Blonde woman she had ever seen and through all the drama her hair was always beautiful and in place, she hoped that People would respect a Tippy more than they would a Tiffy.
She had been contemplating her life choices and future, after turning 18 over the summer, and had made a decision in the first couple of weeks of her senior year. She needed to up her game and be more discriminating in her choice of male companionship. She vowed to stop being the school slut, no matter how horny she got. She was in the library doing further research on fermentation, and as she had hoped, Bret was there. He was online looking at the progress on his college scholarships for next year.
Tippy wanted to talk to him because he was smart and a bit of a nerd. Furthermore, he had always been kind to her and a gentleman, he had never used their times together as lab partners as an opportunity to cop a feel or grab her ass. She had run out of suitable partners in the male population at their small high school and was only interested in a repeat if the subject had particularly tasty spunk and was not an ass.
She sat down at the table next to Bret and asked how he was. Quietly they carried on a conversation. "Any luck with money?", she asked. In their small rather poor community, money for continuing education was a big deal.
.
Bret said, "I have a few things in the works", he had always liked Tippy and welcomed any opportunity to interact with the cute blonde, he knew that Tippy was a brilliant student, even if she did have a reputation, and that she had gotten a full ride to a small Technology arts school in the next state.
Tippy said, "Can I ask you a personal question?"
"I suppose."
Tippy smiled and asked, "Are you any good at cunnilingus?" Bret made a startled sound and got a disapproving look from Ms. Taylor, the librarian.
Regaining his composure Bret took off his glasses and whispered, "I wouldn't know, I have never had an opportunity to try it."
Bret's pupils were as big as saucers as Tippy asked. "Would you like to try it with me? You could even fuck me."
Bret was completely tongue tied and could only nod yes. He had always wanted to be with her but was intimidated by the Jocks she usually dated. Bret's parents were going to be out of town on the weekend, so they planned to have a private party at his house on Saturday evening. Tippy knew she had picked the right boy when by Thursday there were no more leers or stares or snickering than usual. True to form Bret had played the gentleman.
She started to think about Saturday, a sexual interlude with a romantic component was new to her. She wanted to be prepared. When she was supposed to be doing homework on the family computer, she read up on cunnilingus technique and watched some lesbian porn on the internet reasoning that lesbians would know how to eat pussy, she even found a couple of instructional videos. Since she had been fucking and sucking less, she had used porn to get her in the proper mood to masturbate so she knew her way around the major free porn sites.
There was lots of eating pussy porn that really got her going and increased her desire to try the real thing, but due to the close quarter's nature of the activity the videos left much to the imagination and she didn't have the real world experience to fill in the gaps. The women all seemed to enjoy it and she was pretty sure she would to. She had sucked so many dicks in her young life that she felt Karma owed her this experience. Bret seemed to be the perfect person to balance the scales. She was determined to make it worth his time.
She was distracted all week, so was Bret. He had been having masturbatory fantasies about Tippy since freshman year. It bothered him a little that she was the school slut, but she had always been nice to him, nicer than the stuck-up bitches in the bitch club, and besides, nobody is perfect. He did what research he could but as a virgin he didn't have a frame of reference for the information.
Tippy was the product of a broken home in their small community. Her father left her alcoholic mother when she was five, so it was her and her younger brother, Matthew. She cried a lot as a kid. Her mother drank and drank. She developed coping mechanisms to keep her and her family alive. At home she tried to be the responsible parent that her father had never shown any aptitude for, and she succeeded. They didn't have much, but they got by.
She inventoried her assets. Pretty face, Natural blonde hair, blue eyes, shapely and fit legs, ass and torso and a perfectly symmetrical and perky set of C cup tits. And a great memory and keen mind, she was good at math. Planning ahead, if they could sell half of the jars of moonshine she distilled in the still she built from junk yard scrap and some copper tube they might even survive next winter without Child and Family services breaking up her family. Mom would be better off without 2 kids to raise but without them to live for she would soon drink herself to death. Her going away to college would be hard on her Mom and on Matt, but she needed a degree so she could get a good job if any of them were to have a real future. Some nights she cried herself to sleep from the stress.
Socially and at school was another issue altogether. Being from the 'wrong side of the tracks" as it where, she was the brunt of teasing, cold stares, and all sorts of abuse. Her freshman year Tippy made an interesting discovery at the first of the season's football games. Even the boys who teased her were still very interested in touching her tits. She also discovered that the feel and taste of a cock in her mouth was nice, it excited her and made her tingle between her legs. In that freshman year she lost her virginity to some asshole who told everyone she was a tramp. The second time was better, she even had an orgasm. A couple more of those on her own and with a dick and she was hooked.
After the first time she never went anywhere without a pack of condoms. If a guy wanted to cum in her he had to do it in her throat, or they could pull the condom off and cum on her tits. She became the school slut and embarked on a study of as much spunk as she could taste. Her inquisitive mind forced her to ask, "What did you have for dinner last night?" She also put out the rumor that she heard that pineapple juice was the thing. The cafeteria couldn't keep it in stock. The guys and girls all knew she was a slut but guys didn't care. She was a great piece of ass.
Her promiscuous behavior became her best coping mechanism, when she had a cock in her mouth or her pussy, she could forget all the problems at home and the misery of her teenage life. Unfortunately, these liaisons never translated into any permanent loving relationships and no guy, except Bret was interested in going down on the school slut. As she became a connoisseur of sperm, she kept a mental checklist of her activities. If any of her female contemporaries had asked, she could have told them who tasted the best, who was gentle, who was rough. Who 'might' be worth investing time into, inventory on every guy at school who she had been with, she was a walking Wikipedia of slutish knowledge.
