Ashleigh's Christmas Break

Part 5 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 4: Ashleigh's Winter Ball. Ashleigh goes to her sorority semiformal.

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

Ashleigh Holton waved goodbye to the last of her sorority sisters as they pulled away in a cab. She had told everyone that her flight wasn't leaving until early evening, but the truth was that she wasn't even flying. Unlike all the other Kappa girls, Ashleigh couldn't afford to fly airplanes. Every cent she had earned during the semester went towards keeping up her lofty Kappa image - new clothes, new shoes, new jewelry, and new phones. As a matter of fact, after having spent the requisite $500 on her Secret Santa gift, she now had a total of $86 to her name - $25 in her bank account (the minimum balance) and $63 for the bus ticket home, leaving her ... fuck, she miscalculated, and hadn't left any money for lunch and dinner. Probably just dinner, she decided - she'd finish off a box of Cheerios left in the kitchen for lunch. She was going to have to drop below the minimum balance (which would cost her a monthly charge of $10) or find $2 worth of change in her pockets.

Ashleigh went upstairs and dug out the small, ratty suitcase that she had arrived on campus with. In it were still all her old clothes - a pair of non-designer jeans, a few shirts from Walmart. She sifted through her "new" clothes to see what she could use to augment her wardrobe - after all, her mom thought she had a job and expected her to have a few nice things. She finally settled on adding a few miniskirts and blouses, then changed her mind and decided to pack the jeans and wear a light blue bubble skirt. She was still 18 for a few more months, she had the rest of her life to dress like a grown-up.

Ashleigh was admiring her flowing blonde hair in the mirror when she noticed that Old Man Summer had his shades up and was walking around buck naked. He probably thought all the girls had left for the semester, and didn't need to heed their court injunction to keep his shades down (or put on some pants!). Earlier in the semester he had paid her $800 to fuck him, and she drooled at the prospect of earning some easy money again.

As Ashleigh crossed the alleyway to Mr. Summer's house, a dirty cavern of pornography and wadded up tissues, his door swung open, and he stood there with his semi-rigid dick hanging out and a big smile on his face.

"You need cash?" he sardonically stated. Ashleigh frowned at his accuracy, but nodded silently. "Well, all I have is $100 on me, but I'll let you jerk me off or something." Ashleigh frowned even more at his derision, but she really needed the money, so she reluctantly agreed.

She took a step towards entering his house, but he stopped her. "One last thing," he said, "I wanna do it on your bed."

"You've got a fucking restraining order against entering our house," Ashleigh protested. "It's against the law."

"So is jerking people off for money," countered Mr. Summers. Touche.

Mr. Summer grabbed the cash and the two went back into the Kappa house, up to Ashleigh's room. Mr. Summer was buck naked and touching himself as he snooped around Ashleigh's pictures. "Your little sister?" he asked, stroking his dick while he took a mental snapshot. Ashleigh grabbed the picture away from him and put it face down on her dresser.

Mr. Summer lay down on Ashleigh's bed, resting his head on her teddy bear and letting his raging boner sway in the early morning sun. Ashleigh knelt on the bed between his legs, pulling out a bottle of lube from her nightstand. She lubed up his warm dick and began stroking it up and down with one hand. As his dick got fully erect, she started using both hands, one hand holding the base firmly while she pumped with her other.

"How about you let me cum on your panties?" Mr. Summer asked. Ashleigh shrugged. Whatever got him off the fastest.

She straddled his hips and lifted up the front of her soft, plush skirt to expose a pair of plain, white panties. She aimed his dick at the entrance to her pussy as she kept stroking him. His precum dabbed onto her panties, wetting them and making the thin fabric slightly transparent. Mr. Summer could easily see the outline of her pussy lips as her slender fingers brought him closer to orgasm.

"How about you suck it a little?" Mr. Summer prodded. Ashleigh rolled her eyes. "No way," she said. But Mr. Summer was persistent. At first, he tried to convince her that it wasn't that different, that he'd let her know when he was cumming so he wouldn't cum in her mouth. But she still refused. Eventually, he convinced her to rub his dick with her covered pussy.

Ashleigh scooted forward, resting her vagina squarely on the base of Mr. Summer's dick. She felt the warm lube soaking into the fabric, making it fully transparent. She realized there wasn't a whole lot of difference between this and actually fucking him, considering how thin her panties were, but she wasn't going to give it up to him for just $100. She used one hand to press his dick against her cunt, and then gently moved her hips back and forth to stimulate him.

The stimulation worked both ways - Ashleigh realized her wet, sloppy panties were tricking her nether regions into thinking she was the wet, sloppy one. Soon enough, Ashleigh's clit was poking out from its hiding place and Ashleigh was moaning with as much pleasure as Mr. Summers. She could feel the veins on Mr. Summer's rigid dick rubbing her clit up and down. She was nearing orgasm herself when Mr. Summers announced that he was cumming, and Ashleigh reluctantly backed off a little to guide his spasming dick towards her panties. Stream after stream of warm, sticky jizz poured out of his dick and splashed onto Ashleigh's panties, turning them into a huge, sticky mess.

After he was done cumming, Ashleigh took her cummy panties off and, on Mr. Summer's request, gave them to him as a souvenir. She locked the door behind him before returning to packing.

Chapter 2

One of the hardest parts of going to college for Ashleigh was having to return to the way she once was. She had to transform herself from President-to-be of the hottest sorority on campus to a quiet, small-town babysitter. Sure, she had lost her virginity in high school which made her a rabid slut by town standards, but her ex-boyfriend had the good sense to keep his mouths shut, and all of the adults still thought of her as if she were 8 years old and selling Girl Scout cookies at church.

Church! Ashleigh suddenly remembered to pack her church outfit. Her stepfather was one of these super-religious nutjobs and Ashleigh actually had to buy a church outfit and take a picture with some "church friends" at a local church to pretend she still gave a shit. Her mother had always been a little religious, but after her dad left them, her mom had become a lot more serious. Ashleigh stuffed a knee-length floral dress and a cardigan into her bag and decided it was good enough. After all, she was only going to be home for two Sundays.

With her newfound money, Ashleigh ordered delivery from a local cafe, and then watched a Jersey Shore marathon for a few hours before heading out to the bus station for the 7pm overnight to Lakeville. The bus station was only a few blocks from the Kappa house, but Ashleigh still hated walking there. She still remembered arriving there on her first day, rolling the same suitcase behind her, cringing at the homeless people who had camped out on the lawn.

Actually, she still cringed at them. It was probably the same two guys, having lived there for years with their makeshift tents and shopping carts full of random shit. She tried not to look at them as she walked by, even when they tried to get her attention.

Ashleigh bought her ticket and sat down on the benches inside the station. Having 15 minutes before the bus left, she pulled out an issue of Cosmo that she had been saving for the trip, and began reading about the 7 sex tricks that men would cheat on their wives for. There were actually two that she hadn't heard of before, and she became so engrossed in the article that she missed the part where the homeless guy walked by and swiped her suitcase. Fortunately for her, someone's dog yelped, and she looked up in time to see the man dragging her suitcase out the front door.

"Hey! What the fuck! Stop!" shouted Ashleigh, running after the homeless man. The other passengers ignored her plight as she ran across the station and outside. By the time she found their encampment, the two homeless men had already dumped her suitcase onto the muddy ground and started rummaging through her stuff. "Stop it! That's my bag!" yelled Ashleigh. They didn't pay attention.

Ashleigh grabbed her suitcase and started stuffing things back in, trying to keep track of the things they had already pocketed - one guy put her hair curler in his cart, another pocketed her glasses case. Ashleigh's big mistake came when she pushed one of the guys to keep his hands off of her blouses; he didn't take to that very well. As a matter of fact, they both stood up and glared at her.

"This is my stuff," Ashleigh started explaining, but the one she had pushed sneered and responded, "No, this WAS your stuff. It's our stuff now." Ashleigh stood up as well - she was a few inches shorter than either of them, but she thought they'd back down. They didn't. Sensing the threatening tone of her voice, the two homeless men did as their instincts had taught them to do over the years - they pulled out their shivs and prepared to defend their territory.

Ashleigh tried to run off, but the two men grabbed her arm and pulled her back. Terrified, Ashleigh tried to negotiate with them. "Please! You can keep the hair curler. I'll give you money for the rest of my stuff back! Please!" The two men were unimpressed. They had thought that Ashleigh was some rich bitch, but her suitcase was pretty devoid of anything valuable. No jewelry, no electronics, nothing that would bring them the payday they thought they'd have. The $22 that Ashleigh was frantically shoving in their faces was a pretty small payday. But they took it anyway.

Ashleigh zipped up her suitcase and started running back to the bus station when she remembered the glasses case. It had her glasses in it, and she didn't bring any of her contact lenses with her. Ashleigh ran back and demanded the glasses case as well, but the men asked for more money. "I don't have any more!" pleaded Ashleigh. "I gave it all to you already!"

"Well," one man drawled, "You're gonna have to barter for it then."

Ashleigh saw the leering looks on their faces and suddenly realized what they meant. Worse yet, she heard the announcement for boarding her bus over the loudspeaker, which meant that she had five minutes to get on the bus. "Fine," Ashleigh stated flatly. "I'll suck your dicks. But you better be quick." The two men were rather stunned by the speed at which she agreed, and stood around wondering what to do next when Ashleigh pushed one into the tent. He sat down, stunned, while Ashleigh ripped his greasy jeans apart to extract his dick. Ashleigh lowered her head onto his dick and almost gagged at the smell of piss and shit that wafted from his pants, but resolved not to miss her bus. Kneeling down, she wrapped her lips around his dick, and squeezed the base to bring him to full erection.

Walter hadn't had a blowjob since the 70's. In his younger years, he got plenty from all the sluts at the hippie conventions who'd suck and fuck anyone. He'd done a few years for trafficking LSD, and by the time he got out, girls were prudes. For a few years, before he looked like total shit, he got away with jerking off at the adult bookstores, but they started banning him a while back. Now he just jerked off in his tent into a pair of ripped panties he found in the trash on campus. The cute blonde going down on him brought back memories.

So did the sight of Red sneaking up on Ashleigh and surprise porking her from behind. Walter forgot Red's real name. They met at a Communist Party rally at some point and used to double-team girls all the time. Usually, with their prior consent, but usually there was so much sucking and fucking going on that there wasn't a big deal. Ashleigh didn't seem to mind, either, as Red yanked down her panties and slipped his dick into her eager cunt.

Ashleigh slobbered all over Walter's dick, trying desperately to get him to cum as quickly as possible. Doing Red at the same time wasn't her choice, but at least it did cut down on the amount of time it took to get them both off. Ashleigh heard the second call over the PA system - she had a minute, tops, to finish them off. The guy fucking her from behind started cumming, bucking wildly as he sprayed his seed into a real woman for the first time in years. Ashleigh redoubled her efforts on Walter, who just let his jizz go with barely a whimper. His dick pumped a mouth full of semen into Ashleigh, who mostly just let it dribble onto the floor of the tent.

As soon as the last spurt left his dick, Ashleigh jumped up, grabbed the glasses, and ran off towards the bus station. Walter and Red laughed as she ran off, hoping that she'd miss the bus so they could fuck her a little more, but she managed to catch the bus just as it was pulling away.

Chapter 3

Ashleigh didn't get a window seat at first, opting to sit next to some crazy cat lady for the first leg of the journey. She wasn't sure, but she was pretty sure the cat lady could smell the cum and was eyeing her suspiciously. Or maybe it was just that cat ladies eyed everyone suspiciously. Either way, when Cat Lady got off at the second stop, Ashleigh slid over into the window seat and nobody sat next to her. She grabbed two blankets off the shelf and used one to make a pillow / hood / eyemask so that nobody would bother her.

Most of the people got off the bus just after midnight, at the final refueling stop before the bus went express to Lakeville. Ashleigh, a young couple sitting across the aisle, and two single guys were all that remained. As the bus pulled away, Ashleigh retreated into her little cave and tried to sleep, but the couple across the aisle kept shifting around. Ashleigh tried to ignore them, but their shuffling made so much noise that she could actually hear them over the roar of the bus engine. She was about to move seats when she realized they weren't just moving around, they were fucking!

Both the man and woman were facing away from Ashleigh, but from her vantage point she could clearly see the woman's pants down on the ground and the man plowing her from behind. Ashleigh reached down and started playing with herself as the two lovers fucked. After a few minutes, Ashleigh was dissatisfied with what she was able to see, so she sat up a little, and ended up looking the woman right in the eye through her reflection on the window. Ashleigh was a little startled, but all the woman did was smile as she was plowed from behind. She actually enjoyed being watched!

Ashleigh kept rubbing herself under the blanket, and then decided she didn't really need to be shy if the woman wasn't. Ashleigh dropped the blanket and let the woman see her bubble skirt pulled up to her hips, and her hand down the front of her white cotton panties stroking her clit rhythmically. Ashleigh continued watching the couple, who slowed down and sped up as they got closer or further from orgasm, respectively.

Eventually, the woman turned her head around and said something to the man, who then turned around to watch Ashleigh. Ashleigh stopped at first, but then resumed when it was clear they just wanted to watch her for a little bit. Ashleigh pulled her panties aside to expose her pussy to the dank, night air, and then started inserting fingers into her snatch - one, two, then three.

The man and woman flipped around so that they were facing Ashleigh now. The woman's shirt was pulled up over her tits and her bra pulled down. The man played with them as they watched Ashleigh masturbate together. Eventually, they began fucking again as Ashleigh rubbed herself silly.

When the couple stopped fucking, Ashleigh had assumed it was because they (or at least one of them) came, but the woman stood up (hesitantly at first) and pulled Ashleigh over to their side of the aisle. Then the woman sat down in Ashleigh's seat and put a leg up, spreading her pussy so that Ashleigh and the man could see. The man pulled Ashleigh into his lap, kissing her neck and nuzzling his penis between her slightly parted legs. Ashleigh allowed his hands free access all over her body, letting him pinch her nipples and nibble her earlobes as she settled down facing the aisle. His hands pulled her panties down to her ankles.

Ashleigh watched the woman finger-fuck herself as the man's penis mirrored the action and slipped into Ashleigh's pussy. He timed his rhythm to match the woman's, coordinating their ins and outs together. As he fucked her, the man reached around to continue playing with Ashleigh's magnificent tits. The woman's pace was faster than the man could keep up with, and Ashleigh heard a low moan over the grinding of the bus engine as she came. Ashleigh gritted her teeth as well as she was on the verge of cumming.

Unfortunately, the man stopped fucking her while the woman came, more interested in watching his wife cum. The woman stood up and Ashleigh thought that the session might be over before she (or he) came, but the woman gestured for Ashleigh to sit up and straddle the man. Ashleigh complied, kicking off her panties, and she positioned the man's still-rigid dick at the entrance to her cunt. The jostling of the bus made his cock tip bounce around, poking her labia as well as her clit and pussy. Ashleigh parted her legs and let him slide inside of her, while his wife sat in the seat beside them and watched.

Ashleigh kept bouncing up and down on the man's cock, which seemed to have eternal stamina. The wife reached over and began playing with Ashleigh's tits with one hand and ass with the other. One set of fingers gently circled around Ashleigh's areola while the other circled her asshole. Eventually, one of the fingers poked into Ashleigh's ass, and she rode up and down on both the dick in her cunt and the finger in her ass. Ashleigh couldn't take it any more and began cumming, loudly, not caring at all what the remaining passengers thought.

The man underneath her also came, but not knowing if Ashleigh was on birth control or not, pulled out and sprayed his cum all over the inside of Ashleigh's skirt, which was super annoying. Because her mom did all the laundry at home, it was going to be hard to hide jizz stains. His spurts became more and more infrequent as he emptied his balls, the last little bit dribbling out of the tip onto Ashleigh's pubic hair. The damage done, Ashleigh just used her skirt to wipe off all the fuck juices in her cunt, and then went back to her side of the bus and slept.

Chapter 4

It was the first time Ashleigh had seen her mother, Rachel, since Labor Day, since she spent Thanksgiving with some of her sorority sisters, and the two of them caught up over a heaping plate of french toast and sausage. Ashleigh's 6-year-old stepsister Amanda was there, too, a little brat of a girl that thought she was better than Ashleigh just because her parents were married when she was born. But unlike Gary, her stepfather, she was sweet and nice and tried to make the most of their forced relationship.