Ashleigh's Winter Ball

Part 4 of 8. Each part is self-contained and reading previous parts is not essential to the continuity of the story, but several recurring characters are only described in detail on their first appearance.

Part 1: Ashleigh's Ride Home. Ashleigh misses her ride home after cheerleading practice.

Part 2: Ashleigh's Game Day. Ashleigh and the other cheerleaders help their football team in any way they can.

Part 3: Ashleigh's Research Project. Ashleigh has waited until the last day to finish her research project.

Part 5: Ashleigh's Christmas Break. Ashleigh goes home for Christmas.

Part 6: Ashleigh's Spring Break. Ashleigh goes to Cancun for spring break.

Part 7: Ashleigh's Summer Internship. Ashleigh gets a pretigious summer internship.

Part 8: Ashleigh Plays I've Never. Ashleigh plays a game with her sorority sisters and recounts her sexual past.

*****

Chapter 1

"You ready to pay for that now?" asked the store manager, Jim. He already had his dick out and was playing with himself. Having watched pretty Ashleigh Holton try on semiformal dresses for the past hour had made him incredibly horny, and since the leggy blonde had offered to pay for her dress with her pussy, he had shut down his little boutique store for privacy.

Ashleigh took one last look at herself, holding up her long, wavy blonde hair to double check how she'd look with it up. Her blue dress sparkled brilliantly as the spotlight reflected off of the sequins. She'd actually have preferred a strapless dress, but this sphagetti-strap dress was the only one that was in her "price" range. The boutique was a favorite of the Kappas, who knew they could always "trade" their way to a discount, but the man was smart enough to charge a premium for the designer stuff.

Besides, Ashleigh didn't have much time - the Kappa sorority's Winter Ball was tonight and if it had been anyone besides her big sister Brenda who had picked the same dress she had, she would have gone ahead and worn it anyway. But she couldn't show up her big sis like that. So here she was, on the day of the ball, trying to find a last-minute dress. Plus, her hair and makeup appointment was in an hour.

"Yeah," Ashleigh finally replied. This dress was at least a 7. Maybe an 8. She carefully took the dress off and stepped out of the heels, but Jim told her to put the heels back on. Ashleigh teased him a bit by first wiggling into her red plaid miniskirt and putting on the black belt before bending over to put her heels back on. She stood upright, naked boobs glowing in the spotlight, and beckoned the balding, 40-something man over. At some point in the past few minutes he had slipped on a condom, and Ashleigh giggled as she grabbed his throbbing dick. He bent down to suck on her nipples, and Ashleigh enjoyed it.

Eventually, Ashleigh led him over to the glass table they had cleared off for this exact purpose, bending over and lifting one of her legs to give him unfettered access to her pussy. She felt the dry latex press insistently against her twat, gradually lubricated by her juices as he slid deeper and deeper into her. Jim stood behind Ashleigh, casually stroking her back and flipping up the back of Ashleigh's skirt to get a better view of himself plowing the innocent college coed.

Ashleigh whimpered as Jim fucked her. She felt a surge of energy as her body responded to the dick buried inside of her, and Jim's balls slapped against her clit with each thrust. She wanted to reach down and rub herself a little, but he was precariously balanced on a small glass table as it was and she had to brace herself with her hands to make sure she didn't fall over and break the table - or worse yet, her heels.

Even with the condom, Jim knew he couldn't last very long, and he knew the Kappa girls were well enough acquainted with dicks so that he couldn't pretend he hadn't cum. Pushing as far as he could inside of her, he slammed as fast as he could without breaking the glass. In time, his restraint faltered, and he filled the condom with warm jizz.

Ashleigh, like she did last time, lay prone on the table for a few minutes to allow him the pleasure of finishing himself off. That was one of the reasons he brought out some of the better shit for her - as well as one of the reasons he had encouraged that Brenda girl to buy the same dress as Ashleigh had purchased a month ago. Ashleigh was a natural.

After they were done fucking, Ashleigh wiped up a little and put the rest of her clothes back on while Jim wrapped up the dress for her. Ashleigh thought she actually had 15 minutes to spare before her boyfriend Jason picked her up, but when Jim re-opened the store, Jason was already waiting outside ...

Chapter 2

"The guy closed the store for you like you're Angelina fuckin' Jolie or something?" inquired a suspicious Jason.

Ashleigh lied. "The guy's wife was a Kappa, he gives us all the 'star treatment' while we're there." Jason bought the explanation, figuring all the rich bitch Kappas just charged up their daddy's credit cards. The Kappa he had dated last year, Katrina, routinely referred to anything less than $100s as "small bills." Ashleigh's secret was that she was actually on scholarship, and most of the nice stuff she had - clothes, shoes, purses - were actually paid for with sex. Even her getting Jason to drive her around was as much of a business arrangement as it was dating.

As part of the "business arrangement" (and to take his mind off of any lingering suspicions), Ashleigh snaked her hand into Jason's pants as he drove her to her hair and makeup appointment, grasping the base of the shaft and tugging it until she felt the veins bulge beneath her fingers. She was careful not to jerk him too hard - a few months ago they got into a minor accident when he came in his pants and didn't notice a red light.

"You know, my appointment's not for another half hour ..." Ashleigh pointed out as they exited the freeway. Her stylist was just a few blocks from the freeway, so they were really early. She could probably show up anyway and see if they could take her early, but she kind of wanted Jason to finish the job that Jim had started, both for business and pleasure.

Jason banged a left off the freeway and headed towards the resevoir. Even though this place was a good 15 miles from campus, everyone came up here to fuck, even the upperclassmen who had their own rooms. Speeding through the parking lot and up an unmarked access road, Jason pulled into their favorite spot - a secluded picnic area overlooking the resevoir. Jason put on some music before joining Ashleigh in the back seat.

Ashleigh had already opened up her blouse and taken off her bra and panties, in the interest of time of course. Jason made a half-hearted attempt at foreplay by sucking on her nipples and kissing her neck, which Ashleigh gladly faked pleasure at to cover up the fact that she had been dripping wet since she had paid for her dress.

After a few minutes of pretending she wasn't a total slut, Ashleigh pushed Jason back against the far wall and pulled his aching dick out of its confines. She sucked on the tip a little, swirling her tongue against the head, then, leaving a little wad of spit balanced on top of his erect dick, pressed it up against her nipple and rubbed her nipple with his slimy dick. She repeated the procedure with her other nipple, letting his prick tip bring her nipples to full erectness.

Ashleigh looked up at Jason, and in a lusty voice breathed, "I want you inside of me." That wasn't a request that she needed to make twice! Ashleigh leaned back, letting her blonde hair splash across the seat, and leaving her breasts flanked by her opened white cotton blouse. Jason kneeled on the seat between her legs, guiding his stiff cock towards her drooling pussy. Leaning forward, he sank into her. In response, Ashleigh wrapped her legs around him, pulling him deep inside.

Even though the angle was a little awkward due to the cramped space, the two developed a consistent rhythm. Jason's slimy cock pumped in and out of Ashleigh as she cried out in pleasure and pulled him in. Ashleigh felt the surge of pleasure as her body welcomed the robust cock. Ashleigh couldn't think of anything besides the growing inevitability of orgasm. She could feel Jason getting ready to cum, too, but she was going to be right behind him, riding his throbbing cock to her own orgasm. She felt Jason pushing more and more deliberately into her as his cock began to twitch and unload a giant jet of semen into her ...

*KNOCK KNOCK* The loud rap of a wooden baton against the side window scared the shit out of Ashleigh. Her eyes snapped open to see the disapproving glare of a police officer gesturing to the two lovers to step out of the car. Jason also froze, his cock quickly shrinking as the last pumps of cum oozed slowly out of his dick.

Ashleigh and Jason quietly put on their clothes and stepped out of the car. The officers got their IDs and gave them each a ticket for public lewdness, and then sent them on their way.

"I'll take care of you when we get back," Jason promised. But she knew he wouldn't.

At least he paid for her ticket like a gentleman.

Chapter 3

Ashleigh was still horny as hell, but temporarily forgot about it as she got dolled up. Hair and makeup, mani/pedi, and a short backrub by a fat Korean lady, and it only cost her $150. Jason picked her up with his usual stupid joke of rolling down the passenger window and asking her how much for a blowjob.

After Jason dropped her off at the Kappa house, Ashleigh ran upstairs with the intention of masturbating with her vibrator, but the whole Kappa house was a huge fucking wreck with everyone rushing around to get ready and Ashleigh couldn't bring herself to sexile her roommates for a solo session (although almost any other day would have been fine).

Ashleigh put on her dress and heels, and then loaded up her purse with just the essentials - her fake ID, her last two $100s for the semester, some extra makeup, and a 3-pack of condoms. She rushed downstairs just in time. All the Kappas gathered in the living room for a pre-ball toast, starting with Andrea, the Vice President and cheerleader co-captain, and then Amy, the President. After each toast, Ashleigh felt the warm tingle of champagne sliding into her stomach, and the warmth reminded her how badly she could use a good reaming.

The Kappas exited their sorority house in single file in pledge order, their dates lining up likewise outside to escort them to the waiting limos. Jason placed a corsage on Ashleigh's wrist and a small kiss on her cheek as he guided her towards the 4th of 5 limos, which carried the last two sophomore pledges and the first four freshman pledges, the latter of which included Ashleigh.

The Kappas had rented out the entirety of The Rose Garden, an upscale restaurant in the city. With the remaining daylight hours, the Kappas took pictures in the garden - as a group, by pledge class, by family tree, etc. Hors d'oeurves and more champagne were served. (Didn't anyone at the restaurant think it suspicious that everyone in the sorority was 21?) By the time dinner was served, Ashleigh was slightly tipsy and very horny.

Ashleigh made small talk with her pledge sisters over salad, but her mind was mostly elsewhere. "Wanna sneak out and fuck?" whispered Ashleigh to Jason as the servers picked up their salad plates. Jason nodded, and Ashleigh excused herself to go to the restroom without inviting anyone else. "I'll text you," she whispered as she pretended to kiss him.

The restaurant itself was pretty huge, although the main hall had been transformed into a dance floor, so all the tables were in a side hall. Ashleigh headed towards the restrooms, but saw a staircase, one heading up and one heading down. She went up to some kind of storage room. The room had a lockable door and it didn't seem like anyone would walk by, so Ashleigh cleared out some space so Jason could fuck her against the wall, and then texted him her location.

On a whim, Ashleigh turned off the lights and shut the door, waiting by the wall. A few minutes passed, although it was hard to tell since the room had no windows and everything was pitch black. Ashleigh started to get impatient when there was a timid knock on the door and it cracked open. At first, Jason tried to turn on the lights, but Ashleigh called out for him to stop.

"Don't turn on the light, just come over here and fuck me," she said.

Jason started to say something, but Ashleigh cut him off, "Oh, for fuck's sake, just shut the fuck up for once in your life and just fuck me!"

Jason walked into the room and closed the door behind him, putting his hands out to feel his way across the room. Ashleigh led him to her by talking about how her pussy was dripping wet and how she wanted his hot cum. Soon enough, Jason's hands found her heaving breasts and played with them through the fabric of her dress. Ashleigh reached down to undo his belt and zipper, pulling his hardening dick free from his boxers.

Jason slide the straps of Ashleigh's dress off of her shoulders, folding the front down to expose her boobs. Then he bent down and sucked on her nipples. Ashleigh was ecstatic - Jason rarely gave her tits this much attention. She could feel his hot tongue dance around her hardened nipples as he alternated back and forth. Meanwhile, Jason's hands gradually lifted up the front of Ashleigh's dress until he could reach underneath. He tried to pull Ashleigh's panties down, to which Ashleigh giggled - she never wore panties when dressing up, and couldn't believe Jason didn't remember.

Eventually, Jason straightened up and positioned his dick at the entrance of Ashleigh's pussy. She didn't think her heels were that tall, but she was surprisingly as tall as he was, and she had to squat down a little bit to let him slide in. She wrapped her arms around his neck and let him pick up her weight as he began fucking her, and then she wrapped her legs around him and let him press her up against the wall for balance.

Jason's dick was huge and throbbing, and he fucked her deeper than he had ever done so before. He fucked her with urgency and intensity, pulling as far as he could out of her before slamming it all the way back in. Ashleigh moaned with pleasure as she was pinned against the wall by his hard cock, repeatedly. Her concentration broke a little as she heard her phone receive a text, and then ring. Who the fuck would be calling her? Jason slowed down a little, but Ashleigh commanded him, "Don't stop, keep going."

The two lovers continued fucking in complete darkness, aside from the sliver of light from under the door. Ashleigh could feel Jason straining to keep his cum from blasting out as her sopping juices dribbled down his cock and off his balls. His thrusts turned more into bucking than anything, and Ashleigh reached down in a futile attempt to get herself off before he came. Ashleigh rubbed her clit furiously as Jason pumped her full of his gooey jizz. It was quite a bit considering he had just fucked her 3-4 hours ago. Check that - it was an amazing amount to have accumulated. Jason just kept cumming and cumming, unleashing what seemed like months of pent-up semen inside of her. Her phone buzzed with a text again, but she ignored it.

Ashleigh started cumming just as he was finishing off, and for whatever reason Jason just dropped her on the ground and ran off. Ashleigh didn't really care as she came in a heap on the ground, her pussy spasming and leaking jizz onto the ground at the same time. Ashleigh just lay on the ground, breathing heavily, when her phone rang - AGAIN! She told it to fuck off and turned it off without seeing who had called. After a few blissful seconds, Ashleigh picked herself up and turned on the lights. She tried her best to erase the just-fucked look before sneaking back down the stairs to the bathroom, where she wiped her pussy off and smoothed out her makeup.

As she was walking back, curiosity got the better of her and she turned her phone back on to check which asshole was calling her repeatedly. It was Jason.

Jason (7:15 pm): im in the basement storage room, where u at??

Jason (7:23 pm): come on its not funny lets fukk

Uh, oh.

Chapter 4

Ashleigh played it off like it was all a big joke when she got back to the table. Jason was pissed as hell, but she just pretended it was payback for him giving her "blue ovaries" earlier in the day, which kept him on the defensive. Tensions defused during the main course, Jason copping feels under the table and Ashleigh sucking on a string bean suggestively.

Jason kept pestering Ashleigh to let him continue the Kappa tradition of crawling under the table and eating her out during the dinner, but Ashleigh didn't want him to taste another man's cum on her pussy. Instead, she assured him, they were going to fuck like rabbits later. The other members of her pledge class were not so demure, and at some point, every other guy disappeared underneath the table until his corresponding date let out a satisfied yelp.

After the main course, Amy got up to give a toast. Most of the Kappas were outright drunk by this point, and the profanity-laden toast was topped only by the outbursts of "Cunt!" that the sisters were brazenly shouting back at her. Ashleigh and the rest of the freshmen were more muted in their revelry, as the Winter Ball was the night that they started their initiation ceremony, formally changing from pledges to sisters. Ashleigh, as the first of her pledge class, was invited to come up to the stage, which she did, apprehensively. Brenda, her big sister, came alongside her, holding her hand.

"Ladies and gentlemen, Ashleigh Holton received a bid in record time - just 26 hours after rush officially began. And she accepted in record time - just 2 hours after receiving the bid. As the first of her class, she has seniority in every respect, and in time, I'm sure she will be brown-nosed by aspiring Kappas," Amy stated with an air of formality. "But not yet. She's still a pledge, and to remind her that nobody is to be brown-nosing her yet, we've got a little device to remind her." Amy handed a little black jewelry box to Brenda, who presented it to Ashleigh. When Ashleigh opened it, it was not jewelry - instead, it was a small butt plug.

"Between now and the end of initiation, you are expected to wear it at all times. Any sister is allowed to make a spot check, at any time, at any place. Do you understand?" Ashleigh nodded, and waited for Amy to dismiss her, but she didn't.

"Aren't you going to obey directions?" Amy asked. Ashleigh didn't understand what Amy meant at first, until Brenda whispered, "Between NOW and the end of initiation ..." Ashleigh felt her face turn beet red as she realized she was expected to put it in, right now, on stage in front of everyone. She slowly took the plug out of its box, which generated a fresh round of laughter as those who were unfamiliar with the Kappa initiation suddenly realized what Ashleigh was expected to do.

Ashleigh gulped and lifted up the front of her dress to mid-thigh, afraid of flashing the front few rows because she wasn't wearing any panties. She carefully pressed the butt plug at the entrance of her ass, then slowly pressed it in. She opened up her legs a little to allow better penetration, and with a plop, she slid it past the widest point and let her asshole readjust to its new equilibrium. A round of thunderous applause echoed as Ashleigh let her dress back down. Brenda hugged Ashleigh and they took their seats (Ashleigh a little more gently than Brenda) while the other pledges were asked to come on stage and repeat the process.

Jason kept begging Ashleigh to let him see it and eventually she agreed. He ducked under the table with a small keychain flashlight and peeked up Ashleigh's dress. Ashleigh crossed her fingers and hoped he didn't see any cum down there. Whether he did or not, when he resurfaced, all he commented was, "Cool." He had dated Katrina when she was a freshman last year, but they didn't start until second semester so he had no idea what Winter Ball was like.