Ashleigh's Spring Break

Part 6 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 5: Ashleigh's Christmas Break. Ashleigh goes home for Christmas.

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's mom kept begging her to come home for spring break, but Ashleigh refused. First of all, her stepdad was a pervert who had raped her over Christmas. More importantly, nearly all of the Kappas were going to Cancun. This was her first spring break ever, and she wasn't going to waste it. Besides, she was running for Social Chair next year and she just wasn't going to miss the biggest party of this year.

The only real problem was money. Ashleigh lied to her parents and told them she had an on-campus job, but she also lied to her sorority sisters and told them her parents were a lot richer than they were. In her first semester, she got her boyfriend, Jason, to buy her a lot of designer clothes and pay for a ton of stuff, plus she ended up fucking their neighbor, Mr. summer, for some cash. But she broke up with Jason and Mr. Summer got arrested for drug charges over Christmas break, and Ashleigh found herself scrambling for cash in her second semester.

She tried waitressing at a diner at the far end of town. It was far enough so that nobody from campus would see or recognize her, but it also meant that she had to take a cab out and back, which really ate into her earnings. She quit after her first paycheck. Then she got a job in the botany department tending the greenhouses, but she ended the day with scratches on her fingers and hands, and as a varsity basketball cheerleader she had to look her best all the time. She had earned enough to keep up appearances, but as spring break approached, she wondered where she was going to come up with money for the flight. (She was sharing a hotel room with 7 other sorority sisters and obviously she could get plenty of food and drinks for free.)

With a week and a day left before spring break, Ashleigh pulled up her bank statement and sighed - she had $210 in her account, and the minimum payment on her credit card was $180, due the day before she left. She was going to have $30 for the entire trip, unless she found a quick way to make some cash soon.

Fuck.

If only Mr. Summer were still around, Ashleigh knew that she could blow him for some cash. Blowing men didn't bother her, and taking money for it didn't, either. It was just that she didn't have the opportunity. Or did she? Ashleigh pulled up her laptop and stared blankly into the Google home page - obviously, there were plenty of people out there who would pay her for a blowjob. But how was she going to find them? The minutes turned into hours as Ashleigh trolled through disgusting places on the Internet where no young woman should really be looking. Eventually, she found a (relatively) reputable website where she could post an ad for free. She spent a little time looking at a few other ads, uploaded a few cleavage shots, and then crossed her fingers.

The first call came in under five minutes later. Ashleigh realized she shouldn't have given out her real cell phone number. The guy wanted a "date" for that night, which Ashleigh enthusiastically, but as soon as he asked where he should meet her, she froze. In a panic, she blurted out a Days Inn just off the freeway outside the city where Jason had taken her on their one-month anniversary (how romantic!). As soon as she hung up, she realized that cabbing out and renting the room would probably cost as much as she was going to get for her services.

Shit.

She didn't have too much time to plan, however, as the second call rolled in just a few seconds after she hung up. She started stringing together her appointments, realizing that if she could meet a few people that night, she could fix some of her costs. An hour later, her phone was ringing non-stop, and she rushed in to take down her ad because she already booked appointments for 8, 9, 9:30, 10, 10:30, 11:30, 12, 12:30, 1, 1:30, and 2.

Ashleigh plopped down on her bed. It was almost 6, which meant she needed to get all her shit together. First, she located a bottle of mace that her mom had given her. Then, she packed a small bag, one that she could carry out of the house without arousing too much suspicion, with three outfits, some makeup, a whole box of condoms and lube that she kept around for, um, emergencies. She called a cab and dressed in some nice slacks and a blouse, trying to imitate a businesswoman on a business trip.

After she checked into the hotel, though, Ashleigh rapidly transformed herself from mid-20's businesswoman to 18-year-old slut - pigtails, no bra, her unbuttoned blouse tied just below her boobs, a tight black skirt, and then some black garters and tall heels. Ashleigh was uncomfortably nervous, and threw up at 7:55, just before the first knock on the door.

"Holy shit!" the man exclaimed as Ashleigh opened the door. The balding 40-something introduced himself as Rick, and checked her ass out as she closed the door behind him. Usually advertisements for 18-year-old blondes meant 28-year-old brunettes, but this chick was the real deal! His dick went rock-hard right away, and he was a blubbering mess by the time he counted out $200 and laid it on the dresser. He laid down on the bed and let Ashleigh remove his pants. His dick was already throbbing for release by the time she gently wrapped her lips around it, and he exploded into her mouth before she even got to suck him all the way in. Ashleigh was as surprised as he was embarassed. She just let his dick keep pumping jizz into her mouth, unsure of what to do next.

"I'll pay you another $200 for a second pop," the man offered, digging into his wallet. Ashleigh was a little dumbfounded - she thought that he had bought the whole half hour, and probably would have done him again for free. This was easier money than she thought! She straddled him to let him play with her tits through the sheer fabric of her blouse. Meanwhile, she stroked him slowly through his refractory phase until his dick was rock-hard again. Then she sucked it until it was flaccid again. Rick emptied his wallet as a tip on his way out, leaving her $436 for just half an hour of work!

Ashleigh pulled out the bottom dresser drawer and hid her bag with the cash behind the drawer, leaving just the condoms, lube, and mace out in plain view. She redid her lipstick (and hair, which Rick had grabbed for leverage as she went down on him) and watched a little TV before the next client arrived, an Asian businessman who counted out 2 crisp, clean $100 bills and then silently fucked her face while she knelt in front of him. He pulled out of her just as he came, spraying several jets of cum all over Ashleigh's shirt and tits. "Goddammit, you asshole, now I've got to change shirts," Ashleigh complained, but the man was already zipping up and rushing out the door, leaving Ashleigh to wipe herself off.

She tried to wipe the cum off of her shirt, but the water just made her thin blouse even more transparent. Ashleigh thought about changing, but then there was a knock on the door, and Ashleigh decided she'd get this guy done quickly and save a few minutes to change.

Unfortunately, the next guy, a white-haired retiree, wanted to negotiate. They had already agreed on a blowjob for $200, but he wanted full service. When Ashleigh said no, he wanted a discount. Finally, Ashleigh got fed up and told him that he had used up 10 of his 30 minutes, whether they stood and argued or whether she was sucking his dick. The retiree kept yakking away even while Ashleigh slurped his dick into her mouth, and didn't cum until the next guy knocked on the door. Ashleigh swallowed his cum and hurried him out the door, realizing that she shouldn't have stacked appointments back to back.

"Daaaaaamn, girl," her next client whistled as he walked in, a middle-aged black man who called himself X. He flopped down on the couch and whipped his dick out of his pants, stroking it. Ashleigh's eyes bulged at the monster cock that he sported, well larger than any dick she'd ever been with, and that was saying something. "Uh, you've got to pay up first," Ashleigh stated. "Aw no," X replied, "I only pay after I know what I'm gettin'." Ashleigh was firm, though, and he laid out a few crumpled $20's on the table. Ashleigh picked them up and counted - 1, 2, 3, 4, 5, 6, 7, 8 ... $160.

"It's $200," stated Ashleigh.

"It's all I got," X replied.

"Then get the fuck out," Ashleigh told him. She pointed towards the door.

X got up, but didn't put his dick into his pants. As a matter of fact, he was still stroking it as he walked towards Ashleigh, saying how he really needed it and repeating how $160 was all he had. Ashleigh just repeated her call for him to get the fuck out, but suddenly he reached out and grabbed her arm. Ashleigh tried to pull away, but he pulled her towards him, even with one hand, as he kept jerking his dick with his other hand. Ashleigh reached for her bottle of mace, but it was too late, as she felt a warmness on her leg and looked down to see that X had sprayed his jizz all over her skirt and garters. As soon as he squeezed the last few drops out, he pushed her to the ground and then ran out the door, grabbing a handful of $20's on his way out.

Ashleigh counted after he left, and he had left just 4 behind ... all that for $80! She counted her total so far, over $900, and decided she was going to leave after the next appointment, who had the whole hour and was going to pay her $500 to fuck him.

Ashleigh changed into her next outfit, a pair of jean short shorts with a sequin halter top and heels. She felt a little ridiculous walking on the carpet with heels, but when she opened the door for "M.K.M." and he whistled at her, she realized that ridiculous was not when whoring. On the flip side, though, she wasn't whistling at him. He was fat and his hair appeared unwashed, and he looked a lot older than the 25 years he had given her as a description. Still, his $500 bought the same amount of shit no matter who he was, and after he counted out five grimy Benjamins and introduced himself as Matt, Ashleigh laid him down on the bed and pulled his shoes and pants off.

Ashleigh almost laughed when she saw his cock - a tiny, shriveled mass which was only visible now that his gut wasn't hanging over his crotch. She gently parted his pubic hair and licked it a few times. His crotch definitely had NOT been washed recently, or at least, not well. Or maybe Matt had just been touching himself after handling a block of blue cheese. It really didn't matter to Ashleigh, all she had to do was get him off and skip out with her money. Ashleigh returned to sucking him with gusto, breathing through her mouth to minimize the smell. After a few minutes of sucking, she realized that was probably as big as he was going to get - maybe 3 inches, tops.

Ashleigh pulled a condom out of her pocket and rolled it onto his dick. Less than half the condom was being used, and Ashleigh wondered if it would even stay on. She slipped off her pants and heels and straddled him, stroking his dick with her pussy. She then reached up and pulled her halter top off over her head. Matt greedily reached up and played with her tits. He was rough and obviously had no fucking clue what he was doing, but Ashleigh moaned like he was the pro.

After she decided he wasn't getting any harder, Ashleigh positioned his dick upright and let him sink into her. She felt the ring of unused condom more than she felt him inside her, but she put her arms on his flabby chest and bounced up and down anyway. Ashleigh felt him get a little bigger once he was inside her, but she still felt empty and just wished he would be the two-pump chump that she had assumed he would be.

Actually, Ashleigh was right about Matt being a two-pump chump. If he had not jacked off before coming to his appointment with Ashleigh, he probably would have been done by now. And now he got to fuck her every which way for a whole hour thanks to his advance planning! Matt laughed to himself as the young slut enthusiastically slid up and down his dick. He let her go for a bit before requesting that they change positions.

Ashleigh knelt down on the bed and let Matt stick his undersized prick into her from behind. She could feel his gut resting on her ass as he pistoned in and out. The bedsheets where Matt had been laying smelled like dirty feet, and Ashleigh redoubled her efforts to make him cum faster by pushing back against him with every thrust. Matt lifted up his stomach to watch his dick sliding in and out of Ashleigh, then resumed fucking her with some degree of fury. This bitch reminded him of all the sluts when he was in college, always putting out for everyone except for him.

"Alright, bitch, on your back, I can't come like this," Matt directed. Ashleigh gladly rolled over and spread her legs in the air. Matt knelt between her legs and bent down to try to kiss her. Ashleigh redirected his lips onto her neck and tits to avoid his lips. After a few seconds of slurping loudly at her neck, Matt plunged into her and let his weight rest on her. Ashleigh tried to push back at him to keep as much of his sweaty fat from touching her as possible, but Matt wrapped his arms around her back and started humping wildly.

Ashleigh thought it was the new position that made him harder, but it was actually the fact that he had slipped off the condom while he was kissing her neck. Matt used his leverage to plunge his naked dick into her, savoring the wet cunt wrapped around him. Meanwhile, Ashleigh struggled to breathe as he was crushing her rib cage with his weight. Sweat dripped from Matt's forehead as he fucked Ashleigh, dripping onto her pretty face. With each thrust, his fat slapped against her inner thighs.

Finally, Matt felt his cum boiling over and collapsed on top of Ashleigh as he pumped her full of his jizz. Well, maybe not full. He felt a few small spurts and a small dribble flow out of his dick. Then, he pulled out quickly and pretended that he had taken the condom off after he came. He tossed it into the trash can and got clothed, while Ashleigh lay on the bed, trying to catch her breath.

Chapter 2

Ashleigh slept for most of the flight to Cancun. She had pulled an all-nighter the night before, and for schoolwork none the less! Like most of the Kappas, Ashleigh had some guy who would do most of her schoolwork for handjobs and blowjobs. She didn't even have to fuck them, just find someone who was either in class with her or had taken the class before, and presto, her work magically appeared in her inbox, done to near-perfection. But this semester she was taking one of her breadth requirements, economics, and most of the grade came from tests instead of papers, so she had to do her own work. The Kappas had thrown a last-minute party, and because she was vying for Social chair next year, she couldn't exactly skip it for studying. So she drank a little, got nailed by some guy with a big dick who was friends with one of the Delts or something, and around 2am kicked him out of the house and started studying. After her test at 10, she rushed back so she could pack and leave for the airport with the rest of the Kappas.

The weather was warm and balmy when they landed, and Ashleigh marveled at the azure waters. It was her first trip out of the country - actually, her first trip anywhere of consequence, really. She tried to play it cool and pretend that she wasn't totally starstruck, but she just couldn't believe the scenery, even at the airport. And of course, the guys. Holy fucking shit, there were hot latin guys all over and she couldn't wait to be at the beach to see them with their shirts off.

"Come ON, Ash!" Her sisters kept having to redirect Ashleigh's attention to getting through customs. Ashleigh smiled as she saw two agents run to open new booths when they saw the large group of Kappas arriving. The Kappas obliged by dividing themselves equally across the two booths to make sure they were rewarded for their enthusiasm. Ashleigh's line moved slightly slower, and by the time she stepped up to the booth, all the Kappas were waiting for her on the other side of the barrier.

"Anything to declare, miss?" the guard asked. Ashleigh handed over her form, on which she had declared the $1,200 cash that she had in her purse. She could tell something was wrong when the guard called his supervisor over. They spoke in rapid Spanish and in the end, the supervisor motioned with Ashleigh to follow him.

"What's the matter?" Andrea asked. She tried to cross back across the barrier to help Ashleigh, but one of the armed guards stopped her.

"I don't know," Ashleigh replied. "Something with my declaration form."

"Oh, you dumb bitch, you didn't tell them you were carrying over $1,000 cash, did you?" Andrea asked, exasperated. Ashleigh's face turned beet red as all the Kappas groaned out loud. Andrea instructed Brenda, Ashleigh's big sister, to wait while the rest of them headed over to the hotel.

Ashleigh entered a small, windowless room with the supervisor, who introduced himself as Cristiano. "I check your bags for drugs, yes? And I check for gun, yes? And then we are finished." Ashleigh nodded politely, mustering a smile. She handed over her purse and Cristiano emptied it out on the table, lining everything item by item for the camera to see. In her wallet were 11 $100 bills, plus a thick wad of $20's, which he counted and fanned out. When everything was shown to be in order, he put everything back into her purse and started with her carry-on bag. Again, there was nothing of interest, and after capturing an embarrassing number of tabloid magazines on film, he packed everything up and handed the bag to her. Ashleigh had hope that this would be over quickly.

Unfortunately, Ashleigh forgot that she was in charge of carrying the Kappas' condoms for the trip. And when Cristiano opened Ashleigh's suitcase, one of the first things he noticed was a 500-pack of condoms tucked on the side. Ashleigh felt her face turn beet red again as Cristiano quizzically opened the box and then looked at her with a bewildered look on his face. Ashleigh looked down at her feet.

Cristiano sifted through the rest of Ashleigh's belongings. There were clearly no drugs or weapons, but obviously the girl was a prostitute, and he knew how to deal with prostitutes. He quietly unpacked most of her items, and then excused himself from the room. He beelined back to the security room, and turned off the cameras for the interrogation room. Then he raced back to the unmonitored room, and locked the door from the outside before entering. He ogled the young Ashleigh, in her sneakers and jeans, and imagined her working the streets with the hot pink miniskirt he had seen.

"Prostitution is illegal here," he commented. Ashleigh tried to jump in but he shushed her. "Is okay, many girls like you here." Ashleigh was indignant at being called a prostitute, but she quickly realized that he just wanted his cut. She could sit here and try to argue with him for hours, or she could just fuck him and be done with it. She could already see his dick straining against the fabric of his uniform as he reached over and stroked her baby-soft face.