Once a Slut Ch. 01

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.

Friday night was excruciating, then Bret had a depressing thought, what if this was some kind of horrible joke she was playing on him? She wouldn't do that to him, would she? He didn't think so, but the thought worried him, to calm himself he rubbed out 2 loads Friday night. Saturday morning after his parents left, he called Tippy and asked her if she would like to come over in the afternoon so they could have dinner on the BBQ.

She said yes, I will be there at 3, what can I bring? "Just your beautiful self, we have plenty of food and drinks here."

Saturday afternoon, Tippy showered and dressed in a tiny blue jean shorts her Daisy Dukes, cute white panties, white tank top and scandals and walked over to Bret's house. She had her purse with her condoms and a bag with a mason jar of her moonshine, cut down to about 90 proof. Bret greeted her at the door with a huge smile and a hug and a kiss on the cheek. As she pulled him close, she could feel his erection against her belly and his clean masculine smell began to excite her. This would normally have her dropping to her knees for a blowjob but she wanted to break that conditioning.

So, she kissed him on the lips and pulled him deeper into her. She asked, "Are you in any hurry to eat?"

Bret replied, "Not if you have a better idea."

"I do, I would like to do a little research in your bedroom." Bret led her by the hand to his room. On the way they stopped in the kitchen for a couple of cokes, ice and two glasses.

Bret's room was nice, not too messy since he had cleaned up wanting to make a good impression. He had a desk to do homework at and a computer with a decent sized flatscreen monitor. Much nicer than her family's 10-year-old used PC with a tiny screen.

She asked, "may I?", indicating the computer.

"Sure". Bret said as he started it up.

She went to the site where she had done her initial research and loaded up an instructional video on Cunnilingus. "OK, let's have a drink first, so we don't get too excited." She opened the bag and poured about a finger of spirits in the bottom of each glass and topped both off with coke and ice.

Bret had questions, "Where did you get that?"

She said with a little smile, "I distill it at home in the garage. You know about my mom? This keeps her from drinking up all the food money."

Tippy made him promise never to tell a soul anything she was going to tell him, and then explained the entire operation. "I'm impressed, I knew you were smart, but I am still impressed. As they chatted, they drank their drinks and the alcohol helped lessen the tension Bret had been feeling.

They started making out on Bret's bed and Tippy said, "Time for the video." The video showed a woman in her late 20s early 30s lying on her back with her pussy facing the camera legs spread wide. Tippy thought that Bret would get a lot more out of this if he had the real thing to follow along on. She paused the video and stripped slowly for him. Bret almost couldn't resist the desire to grab her in his arms. Reading his body language, she stepped into him pulled him to her and kissed him deeply. Before he got too besotted, she gently pushed him away. She laid down on his bed legs spread and told him to restart the video and join her on the bed with his face between her legs.

Bret was in a state of near ecstasy, she is here, this is really happening my dreams are coming true for a change.

The instructor started by pointing out the various elements to her anatomy. Labia, both inner and outer, vaginal canal and the location of her clitoris under its hood, she explained about various levels of sensitivity to stimulation and how to build anticipation. Bret followed along on his live artists model, her smell was making his heart race and his normally 6-inch cock felt like it had grown an extra inch or two.

While the model was shaved bare Tippy had a very well-tended patch of blonde pubic hair. As the video progressed Bret was eager to put what he had been seeing into action. He nuzzled her inner thighs then kissed her outer lips then dragged his tongue lightly over her inner lips. Through all this Tippy guided him with soft encouragements.

"That's right, that feels really nice, I want more of that."

Next per the video, Bret flattened his tongue out and starting at her taint spot licked all the way up her slit just barely licking the hood of her clit.

Tippy shivered, "Baby, you are going to get one hell of a blowjob for this." She reached down and pulled back her clitoral hood exposing the little love button and said lick me right there. As he moved in, she used her other hand to grab the back of his head pulling him to her. As he had learned in the video he circled her clit with the tip of his tongue, she squirmed on his tongue. He thought he might be doing it wrong or too rough but since she maintained a vice grip on his head, he thought it was Ok.

"Flick it with your tongue, oh yes!", she moaned. "Now stick your tongue into my hole as far as you can", now back to my clit. Through all of this she was squirming under his face, arching her back and panting. "Now suck my clit as hard as you can! Grab my nipples and pinch them That's right only harder, I. Am. Cumming!"

Bret was amazed at her reaction to his attentions. She wreathed under him and panted out her waves of orgasm. When she calmed down, he went back to licking her slit, it had been wet and tasty before but now she was dripping on his bed spread. He knew what a male orgasm felt like and what happened, but the female orgasm was more subtle and mysterious. He hoped it felt just as good. He wanted this to be as perfect for her as it was for him.

"More, I want more", she demanded. She put her right ankle behind his head and pulled his head back into her and wiggled her hips to rub his face with her wetness. Bret kept going but at one point he needed to turn his head to get some air. He loved every second of licking her to a second screaming orgasm. Between her smell, taste, and texture he was spellbound. Even the little whimpers and moans she made sent shivers up his spine. He was pussydrunk for lack of a better word.

As she came down from the waves of pleasure she said. "I am an awful person. I have only been thinking about myself. Your turn." As much as he wanted a turn Bret was thoroughly enjoying making her cum and was a little afraid that if he stopped, he would wake up from the best dream he ever had. He told Tippy as much.

"Oh no! Don't worry about it I am yours for the weekend." She told him to stand next to the bed. She sat facing him at the edge of the bed and proceeded to undo his pants. Pants that showed a big wet spot at the top of his bulge. Pulling his pants down to the floor and peeling his briefs down she found a load of spunk inside.

She said, "Oh my, did you?"

"I did. You taste and smell so good that when you had your first orgasm, I had one too. It's OK though, I should be good for 3 or 4 more".

She smiled and sucked up some of his semen, "Yummy", Was all she said as she licked his cock clean. Discarding his soiled underwear, she proceeded to lick him from base to tip, she swirled his glans with her tongue popped it fully into her mouth then started working down his shaft while cupping his balls and sucking him. She looked up into his eyes and winked. He had never seen such a beautiful face. She went deeper and deeper. As he could feel some resistance at the back of her throat, she gaged a little and he got worried and pulled it out a little bit.

She withdrew him from her mouth and explained, "Don't be worried if I gag a little, I like it. Gagging makes me cum. Grab the back of my head and push into my mouth, Fuck my mouth. If I want you to stop, I will pinch your leg."

He proceeded to face fuck her which she really enjoyed while he panted, she fondled his balls with one hand while she diddled her clit with the other. On one particularly deep thrust she cried out, arched her back and thrashed on his cock while she came. Again, he got in his rhythm. She looked up into his eyes and winked again, dove onto him for another deep thrust and he could feel her throat working his cock again. After the third deep thrust his legs started to tremble and his scrotum tightened preparing for his release, with one last deep thrust Tippy's throat spasmed milking him, she came, he came and shot a load of ejaculate down into her stomach.

She sucked the last spurts coming out of him onto her tongue swallowed with satisfaction and stood up to lean against him. He held her close and went to kiss her. She put her hand over her mouth and mumbled, wait until I grab a drink. He pushed her hand aside and kissed her deeply and sighed. He didn't seem to mind the taste of himself on her lips. She smiled and collapsed into him pulling him as close as she could. No other guy had treated her like this like someone they cared about and respected, like a real lover.

"So, was that the best blowjob you ever had?", she asked with a pixie like grin.

"Definitely the best, since it was my first."

"A day of firsts for me too. No one wants to eat out the town slut, which is kind of unfair because I never let anyone cum in my pussy without a condom and no one has ever kissed me after I sucked their dick. You are my prince charming. Bret took off his shirt and they laid down on the bed and kissed and fondled each other for an hour as the sun moved toward the horizon.

Looking at his long-fingered hands she said, "Baby there is one more thing I need to show you, how to find my g-spot. Lick me a little to get me wet and I will guide you." He was more than happy and enthusiastic to honor her request. As she panted, she said, "Wet your longest finger in your mouth. Hold your palm up and put your finger in me. On the front part of my sleeve toward my hair patch feel for a rough spot, not sandpaper rough, it has some soft ridges. Yes, that's it! You have it. Now stroke the ridges with your fingertip and press down on the spot.

Bret thought this would be a good time to start sucking on her clit again. He carefully worked the spot while he sucked her magic button into his mouth. Tippy started moaning and panting she squirmed on his finger and pulled his mouth hard into her pussy, her juices were running down his hand and pooling in his palm. Tippy arched her back hard and let out a low moan, all she could say was "Cumming! Cumming!"

Her body spasmed and she started to buck wildly bucking off his finger and out of his mouth. She laid there twitching for at least 2 minutes before coming back to him. She looked down at his smiling face and said, "Thank you, thank you so much."

Bret looked down at his hand brought it too his mouth tasted it with his tongue and finding it delirious slurped it all down. Tippy beamed as he crawled up to her head and pulled her tits against his chest and kissed her passionately. "OK." He said, "We have one thing left to do."

"Fuck?" she said.

He replied, "Like I said we have 2 things to do. Eat some food and then fuck!"

"You are right", she said rubbing her hand on her belly. "All I have had to eat today was that great load you shot down my throat. I am famished."

While they dressed, they had trouble keeping their hands off each other.

Bret's Mom had left him some hamburgers and a couple of steaks. Tippy thought steaks were a better choice for their day of firsts, so Bret fired up the grill and cooked them up. They had a couple more shine and cokes with their meal and were both feeling good, really good.

Tippy asked questioningly, "You took to eating my pussy like a duck to water. You don't have to answer this question but who else have you been with?" His proud glow at her praise faded to a frown as he contemplated whether he should lie to her or tell her the truth.

Looking like a deer in the headlights Bret stammered, "No one, you are my first. I have liked you since freshman year. I never found anyone else who I really wanted to be with.

Tippy' s eyes started to well with tears, she sobbed out. "That is the nicest thing anyone has ever said to me." and moved close to kiss him. She kissed him but then backed off and getting nervous stammered, "I have to leave!"

Bret bewildered and panicky said, "But you said you were mine for the weekend!"