Allison Sluts It Up Ch. 01

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Good Girl Starts her sexual awakening.
4.9k words
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1

Part 1 of the 4 part series

Updated 06/07/2023
Created 03/09/2016
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Allison Prentiss was the quintessential good girl. She came from a very Christian household, with very strict parents who forbad dating until Allison was no longer living under their roof. This included dates to proms, homecomings, winter formals, and any other traditional high school event. Six weeks after she turned eighteen, and seven weeks before she left for college a boy named Sam asked Allison if he would go on a date with her. Allison said that she would, but not until the day she moved into the dorms. Sam gave her quizzical look, but agreed. On move in day, they went on their first date.

For the rest of the semester Sam and Allison regularly dated, and shortly before Christmas became an official item. Allison informed her parents, who while upset, were understanding that officially, Allison did not live under their roof, even if she would be back for holidays, and summer vacation.

Sam was just as sheltered as Allison, his parents had forbade him from dating until he was eighteen, and it was on his eighteenth birthday that he asked Allison on a date. During their freshman year of college Sam and Allison never went farther than a quick peck on the lips at the end of a date. In April of that year Sam's roommate Jared asked him when he and Allison were going to fuck. Sam blushed and just shrugged. Jared explained to Sam how fantastic it was to hook up with a girl, and how easy it was to do.

Jared explained that if Sam told Allison he loved her, then within a few days Allison would sleep with him. Sam objected that he did not actually love Allison, and Jared told him that it really did not matter, that it was just something you had to do with prude girls like Allison. Jared also explained that Sam would have to be somewhat slow, and couldn't go too fast with her, or she'd be spooked off.

Sam wasn't sure what to do, but was certain that he was tired of masturbating in the shower, and he wanted more than his own hand to give him pleasure. So Sam did it. He told Allison he loved her in early April. Allison said it back, but she didn't mean it anymore than Sam had. A week later Sam suggested they get a hotel room together for a night and sleep together. Allison was unsure of this, she wanted to have sex more than anything¬-it was admittedly why she told Sam she loved him-Allison was reluctant to Sam's suggestion at first. But ultimately she agreed.

Until she had started college Allison had never masturbated. She had never even given it much thought; but a few weeks into her time in the dorms she walked in on her roommate watching porn, and slipping a dildo into her pussy. Allison immediately walked back out, but the image had stayed in her mind for weeks. In October she asked a friend about it. In November she tried her hand at making herself cum for the first time. Since that first time sliding her fingers into her wet cunt, Allison wanted nothing more than a cock inside of her. She had gone out the next day and gotten a birth control prescription, and was just waiting for Sam to initiate the act.

The day before the hotel room was booked Allison went and bought sexy lingerie. She practiced a sultry walk, and a sultry talk. Allison was ready for Sam, and wanted to make the night as sexy as possible, and she succeeded. When they went into the room Sam immediately started taking off his clothes, but Allison told him that she had a surprise for him, and went into the bathroom to change.

Allison walked out in a black teddy, a black thong, and three-inch high heels. Allison was already five foot seven, and the heels just accentuated her long legs. Allison's perky C cup tits were barely contained in the teddy, and the black fabric made the pink on her fingernails and toenails pop out. She looked like the innocent little eighteen year old that she was, but at the same time, she looked like the incredibly sexy college coed that she could be.

Allison straddled Sam who was sitting on the bed naked. His cock had become hard as a rock when he saw her, and when she straddled him he almost came instantly. Allison made out with Sam, and rocked on his cock. The feeling of his rock hard cock grinding against her clit was amazing to her. The sensations were far better than her fingers had ever been. Allison lowered one strap on her teddy and her left breast fell out. Sam grabbed it like a mad man and began squeezing and sucking at it. Allison was moderately aroused...but not really. It didn't feel how she hoped it would. It didn't feel as good as when she grabbed her own breast. Allison moved his head away from her tit and started kissing him again. She slowly moved her thong to the side, and with her tongue in his mouth moved his cock to the entrance of her pussy. Allison lowered herself more onto his dick, and felt it pop into her. For a moment Allison felt a twinge of pain. Nothing too serious, but a reminder of how virginal she was. Allison grabbed around Sam's neck and rocked herself on his cock. She told him to cum inside of her, that she was on the pill.

Sam only lasted three or four more minutes before he filled her with cum. Allison did not cum. She was disappointed, but knew that it was a possibility, and noted in her mind that next time she would just rub her clit while he was in her.

Over the few months Allison and Sam had boring and routine sex once, or twice a week. Sam wasn't into anything more. Sam didn't want to have his dick sucked. He didn't want to try different positions, and in fact, told her that he just wanted her on her back most of the time. Once in a blue moon she would ride him, but mostly it was just boring vanilla missionary sex. Sam also wouldn't go down on her, something that she had become absolutely obsessed with.

During their sophomore year Allison and Sam seemed on completely different courses in life. Allison was becoming less and less reserved, more free-spirited and open to adventures. Allison was dressing more provocatively, and loved the looks she got from guys around campus. Sam on the other hand had become more reserved. He went out with friends less, and even tried less with Allison.

That same year, Allison was given the chance to tutor for the various athletic teams on campus. Allison tutored three days a week, twice with football/basketball and once with volleyball. While tutoring a freshman volleyball player Allison struck up a really good friendship. The girl was named Janessa, and she was halfway across the country from her hometown, and knew no one other than the volleyball team and Allison.

Allison and Janessa started hanging out a lot. Allison actually saw Janessa more often than she saw Sam. One Friday night Allison was supposed to go out with Sam who called and cancelled because he wasn't feeling well...again. Allison was bummed, but called Janessa, who lived in the same dorm just two floors down, to see if she wanted to grab dinner. Janessa told her to come on down, that she just had to take a quick shower and they could go. Allison went down and hung out in Janessa's room while Janessa showered. When Janessa came back in she was just in her towel. Janessa let the towel drop and Allison was struck by just how sexy she was. Allison had always thought that Janessa was pretty, but never had been sexually attracted to her. But now she was. Allison was more turned on than she ever had been when Sam was naked. Janessa saw Allison starring and jokingly asked if she liked what she saw. Allison responded by getting up and kissing Janessa. Allison was easily six inches taller than the freshman, and she leaned in and drove her tongue into the unsuspecting girl's mouth. Janessa started to push Allison away, but as Allison firmly grabbed her ass cheeks and squeezed, Janessa's desire to resist faded away.

The two girls made out with Janessa pinned against the door for several minutes before Janessa started to remove Allison's clothes. First Janessa unbuttoned Allison's skintight jeans, and started to wiggle them off of her. Janessa then hooked her thumbs under Allison's thong, and yanked it off. Allison removed her own shirt, and while she did Janessa undid Allison's bra and tossed it across the room.

Janessa pushed Allison back enough to grab her tutor's breast and gently began to suck on it, and lick her perky pink nipples. Allison moaned, louder and more honestly than she had ever moaned before. Janessa was good. Janessa was so much better than Sam. As Janessa sucked on her tits alternating between them Allison groped at Janessa's.

Janessa finally broke the lock between them when she was barely able to stand anymore. Janessa led Allison to her bed and laid her down on it. Janessa then kneeled before Allison and for the first time ever Allison felt a tongue on her pussy. Janessa started by biting Allison's thighs, and sliding a finger around her clit. As Allison's head arched back Janessa's mouth latched onto Allison's very erect clit and began sucking. Allison grabbed Janessa's head as if to force more of herself into her mouth when her first orgasm hit her. Allison began bucking up and down on the bed and Janessa had to firmly hold Allison's hips down to keep sucking. After two more orgasms Allison was struggling to sit up and pull Janessa into her she wanted to kiss this girl. Allison tasted herself on Janessa's tongue, and far from being disgusted actually enjoyed it.

Allison then flipped Janessa onto her back and gave Janessa the same treatment. Janessa came just as hard as Allison had, and after two orgasms told Allison to lay on the floor. Allison did and Janessa straddled her in a sixty-nine position and the two spent another twenty minutes pleasuring one another. Finally they both lay exhausted on the floor and held each other.

They never actually got dinner. Janessa and Allison both dressed in Janessa's sweats and loose t-shirts, and ordered a pizza. Janessa asked Allison to stay the night and Allison agreed.

Over the next two weeks Allison and Janessa kept fooling around, and during fall break for the first time discussed it. Both agreed they did not want to date one another. But they also agreed that they wanted to devour each other whenever they got the chance. So they did. While Allison acknowledged that she was cheating on Sam she really did not care. She wanted to dump him, but she was his only social contact anymore and it was just too sad.

Allison finally had her breaking point after the football team won a conference championship. All of the tutors, and other students involved in the team were invited to a party to celebrate the day after the team got home. Allison asked Sam, who promised he would go, and at the last minute bailed. The volleyball team was away on a retreat so Allison couldn't go with Janessa either.

The problem with going single to a football party was that it was basically a giant orgy. If you went by yourself, you would not leave by yourself. Allison still retained some of her prudish ways, and was worried about this. But, she went anyway. Allison arrived an hour after the festivities began. She was in a short red dress, representing the school colors. When she got in she was immediately handed a beer, and within two minutes had bumped into Jamie Crouch, the starting quarterback who Allison tutored once a week.

Jamie was loaded. He told Allison this whole team owed her big time because without her he would have flunked history, and would not have been able to play most of the season. Jamie then picked up Allison hoisted her onto his shoulders and led the whole party in a cheer for her. He then immediately dropped her. Allison got up and made it clear that it was no big deal...but was mortified to know that she had flashed the entire party on the way down, and while she laid on the ground stunned after being dropped.

The party continued on for another couple of hours, and everyone drank too much. One of the program's biggest boosters showed up at half past two and told everyone that there were cabs waiting for them, and not one fucking player was getting a DUI with the national playoffs looming. Jamie was in no shape to walk, so Allison helped him to a cab, and he inadvertently pulled him in with her. The cab took them to Jamie's apartment off campus. Allison helped him to his couch, and he told her to stay the night, and that he'd take her home in the morning. As the words left his mouth Jamie fell asleep on the couch. Allison went into his closet and found a large t-shirt to sleep in. She fell asleep on his bed. When she awoke, a naked Jamie was laying next to her, apparently at some point having stumbled into the room, after stripping himself down.

Allison saw his cock and was horrified by how large it was. Sam was, as she had come to learn from talking to other girls about their exploits, small. He barely clocked in at four inches hard. Jamie on the other hand was easily seven while soft. Allison knew she shouldn't but couldn't help herself. She grabbed Jamie's cock and stroked it till it grew hard. As he began to awake Allison climbed down the bed, and swallowed he cock into her mouth as best she could. This brought Jamie to complete attention.

Jamie's large black cock, and muscular frame made Allison insanely wet. Not as wet as Janessa made her, but pretty close, which was good, because she fully anticipated having Jamie buried inside of her within the hour, and needed to be as slick as possible for the monster that was currently filling her mouth.

Jamie reached down and grabbed a fistful Allison's long blonde hair, and began urging her a bit farther down on his dick, and then pulling her back up. Allison had both hands wrapped around the base of his cock and was stroking up and down as her head moved around the first four or five inches. This continued for nearly twenty minutes with Allison occasionally lifting off of the head of his cock, and moving down to lick the entire shaft, and suck on Jamie's huge balls. At one point Allison removed the shirt of Jamie's that she was wearing, and let him play with her perky tits. Jamie was rougher than Janessa, and less awkward than Sam. His huge hands rolled Allison's nipples around, and without even trying he was able to squeeze the entire breast at once. Allison loved it. Jamie's cock started to pulse hard in Allison's mouth and she was reasonably certain that she knew what was coming...Jamie.

Allison wanted to taste his cum. She kept the same motion she had been going on that was bringing this giant of a man so close to an orgasm, and before she knew what was coming Jamie shot a huge load into her mouth. There was no way for Allison to prepare for the load. She started gagging and sputtering, and as she did Jamie kept cumming. Eventually Allison had to remove her mouth from his cock, and as she did a huge was of cum burst out of him, and across her face. Allison was mortified, but she did not show it. She just casually wiped as much off of her and onto the discarded t-shirt as she could.

After a few minutes Jamie caught his breath, and picked Allison up, and moved her onto the bed. He leaned over her and started to kiss her. As they made out Allison was amazed at how perfectly Jamie was able to play with her tits, and was hoping that he would be impaling her with his cock soon. As she thought this Jamie slid one finger inside of her pussy. Allison moaned as he did it. His fingers were just as long as Sam's cock, and she loved the way it felt moving inside of her. She moved her hips up and down grinding the long finger against her G-spot.

Jamie moved and she could feel his cock pressed against her. She told him to stop, that he could fuck her but that she wanted it doggy style. Jamie grinned and told her that he like how much of a freak she was. She giggled, knowing that Jamie would do things to her that Sam never could .

Allison got on all fours, and as she did Jamie slipped his tongue inside of her. Allison thought that she couldn't get much wetter, and was glad that his saliva would hopefully make his cock less intimidating. After a few minutes Jamie got behind her, and she could feel his dick's head pressed against her pussy. When he first thrust in Allison was ripped apart by pain and screamed out. Jamie immediately removed himself and checked on her. Allison told her she was, but that she had only been fucked by a guy that was half his size, and wasn't aware just how much stretching and tearing her pussy was about to be subjected to.

Allison hated to admitted, but the pain had actually made her even hornier. She liked the small amount of pain with certain orgasms. Like when Janessa would pinch and twist her nipples, or bite her clit. Not enough to really hurt, but enough to associate that much pain with an incredible amount of pleasure. Allison told Jamie to fuck her without concern for pain, that she would get used to it, and that she very greedily wanted that giant cock inside of her.

Allison wiggled her ass at Jamie, and he returned to the position he had been in. His cock pressed against Allison's slit, and instead of waiting for him, she pushed herself back onto his cock. She screamed again, but this time pushed through the pain, and pushed his entire cock into her cunt. She moaned at him to be rough, and to fuck her as hard as he wanted to. Allison was loving the feeling of his cock all the way inside of her. When Allison had first been eaten out by Janessa it was a mini-sexual awakening, a realization that she was attracted to women, a realization that another human could bring her to an orgasm, and a realization that she really truly loved sex. With Jamie it was even larger than that as she road his cock Allison was become obsessed with having it inside of her. When Jamie would pull most of the way out and then replunge into her Allison was rocked by the sensations. Allison had three orgasms around his dick, before screaming at him to cum inside of her. As the fourth orgasm was building Allison dropped her head and shoulders into the pillows on his bed and started moaning deeply into them. Jamie grabbed her by the hair and pulled her up. He loved the noises she was making.

Allison was trembling as Jamie fucked her. In addition to the hold on her hair Jamie was randomly smacking her on her large toned ass, and making it jiggle. After nearly twenty minutes of fucking her his hand pulled back hard on Allison's hair and her head was jerked upward, Jamie filled her with cum as he did this, and Allison was rocked by her fourth orgasm. After he came he stayed put for a minute or two before pulling out. As he pulled out Allison fought the tears off.

She turned and kissed him on the lips. He politely returned the gesture, but it was clear that he wasn't interested anymore. He had an orgasm, and did not need more than that from her. She wasn't sure she needed more either than the orgasms either. But she knew she wanted more of his dick.

Allison showered, put her red dress back on, and had Jamie take her back to the dorm. When she walked into her dorm room, Sam was waiting for her, he had been let in by her roommate Dawn. Sam asked where she was all night, and this morning. Allison told him about the party. He was concerned about what had happened after the party. She was unsure what to tell him. After a few very awkward, and very quiet minutes she decided to be honest.

Allison told Sam first about Janessa, that how the two had been fooling around most of the semester. She told Sam that she liked him still, but that she needed so much more sex than he was willing to give, and that she needed better sex. Sam pointed out that last night, the volleyball team was on retreat, so that she couldn't have been with Janessa then. Allison slowly started to speak, but Sam cut her off and bluntly asked if she was screwing another person on the side too.

Allison told Sam about Jamie. That she had helped him home to be nice; that she had not intended to have sex with him, but that it had happened. Sam slapped her. Allison recoiled more in shock than in pain. The slap hadn't really hurt, Jamie had hit her ass harder than that earlier in the morning. But the betrayal broke Allison's heart. She had never meant to hurt Sam, and had in fact been trying to do the exact opposite all semester.

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