Ashleigh's Summer Internship

Part 7 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 6: Ashleigh's Spring Break. Ashleigh goes to Cancun for spring break.

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

*****

Chapter 1

Even before her internship began, Ashleigh Holton knew that blowing her boss for the job was a bad idea. She just didn't know how bad of an idea it was until her first day, when she was kneeling in the knee space of her boss's desk, sucking on his dick until he blew a huge load into her mouth. And it was only 9:10 am.

Unlike most of her sorority sisters, Ashleigh was on scholarship - both a cheerleading scholarship, which some of them knew about, and an academic scholarship, which she had managed to keep hidden for her entire first year. As a result of her academic scholarship, she couldn't declare bullshit majors like most of her sisters, and most were honestly surprised when she declared pre-business / economics, which was, as Brenda put it, "harder than cocks."

Not a single Kappa had declared econ in the past 17 years, and Ashleigh found herself in the uneviable situation of having to find an internship entirely on her own. And when she found herself at one of the city's most prestigious financial firms with an Ivy League junior as her competition for the spot, she secured her victory by neatly folding her suit jacket on the chair, and then sucking the VP's dick until he let off a torrent of cum into her mouth. Ashleigh swallowed the whole load and sat back down in the interview chair, continuing the rest of the day like it never happened. And eventually, they ended up opening two internship slots so they could hire both of them.

But even on the drive home, Ashleigh realized that by blowing him during the interview, she would probably have to blow him when she worked there. And boy was she right about that - she arrived for her first day in a conservative pants suit and striped blouse, to which her boss expressed obvious disappointment. He didn't even begin talking about what she'd be doing this summer before unzipping and having her go down on him. Then, afterward, he took an incoming phone call and asked one of his subordinates to show Ashleigh around.

"Ray Deike," he introduced himself.

"Ashleigh Holton," she responded professionally, popping a mint in her mouth to cover the taste of cum. She followed him into the elevator.

"So, what are you going to be doing for us this summer?" Ray asked.

"I'm actually not sure," Ashleigh replied. "He didn't say much about it."

"Oh, really?" Ray asked. "Because it seems like you had a 15-minute meeting with him, which is more than most of us get in a year." His statement was intended to embarass Ashleigh, but she was unfazed. Ray knew exactly why Vernon hired her - every year they hired two interns, one for the brains, and one to suck dick. This Ashleigh must have been a real slut, since she didn't seem the least bit embarassed that she had just been caught sucking her boss's dick. Or, maybe she was just too damn stupid to realize what he was implying. At any rate, since she was soon to be the official office slut, he didn't mind making the third floor men's room his first stop.

The third floor was full of large conference rooms, too large for most meetings, so unless there was a huge meeting, it was pretty deserted. And two of the conference rooms were converted executive offices, with private bathrooms. As a result, most of the men at the office knew that if they wanted to jack off, or if they wanted to fuck someone, they should go to the third floor men's room.

"This is where you're gonna suck my dick," commented Ray as he opened the door for her. Ashleigh looked a little annoyed, but she went in anyway. Ray locked the door behind them, and then unzipped himself, pulling his dick out. Ashleigh didn't even object as she knelt down and took it into her mouth, and Ray continued his tour. "You see, Ashleigh, Vernon makes a lot of big decisions, but he mostly gives the small decisions for people like me to make. And what you do this summer is a small decision to him. I can either have you sorting mail or running a whole business division, and he wouldn't give a shit so long as you give him head. And I honestly don't give a shit either so long as you give me head. Which you do very nicely, I might add." Ashleigh resisted the urge to flip him off. And to bite his dick off.

"The other intern, Matt, is going to be reviewing some documents for an upcoming merger we're advising for. He could probably use some help," Ray continued. He paused to let out a grunt of excitement as Ashleigh picked up the pace. "Oh, yeah ... that's right. Just try not to get into his way, okay? And dress a little sluttier tomorrow." With that, Ray gripped Ashleigh's ponytail and shoved himself into her, unloading his balls into her mouth. When he was done, he let her up and zipped up. Ashleigh spit his cum into the sink and washed it down, and then wiped her mouth with a paper towel.

"I think you'll get along just fine," Ray commented.

Chapter 2

"Matt, this is Ashleigh." Ray introduced Ashleigh to the other intern like nothing unusual happened fifteen minutes prior. The two of them were to share an office. Matt tried to hide his instant erection as he shook hands with Ashleigh, who was by far the prettiest girl he had ever laid eyes on, and was going to be sitting 5 feet away from him for the next 10 weeks.

Their task, at least for the first two weeks, was pretty simple - there were sixteen boxes full of documents, and they had to look through each document and classify it into one of four categories. Ashleigh and Matt came to an agreement on the radio setting, and then took a box each and started on their task. For the next two hours, Ashleigh forgot how she got the job in the first place and began believing that she actually belonged.

She was brought back to reality when, on the way down to the cafeteria for lunch, the VP of human resources pulled her aside and said there were a few more forms she needed to fill out. As soon as Matt was out of sight, he dragged her to the third floor men's room and unloaded a dose of reality into her mouth.

Ashleigh picked at her salad at lunch, all the while carrying on some inane conversation with Matt and a few of the other junior analysts who came over and introduced themselves. They were all surprised that Ashleigh went to State, and were floored when they found out she was in a sorority. "So, rumors about sororities: true or false?" one of the analysts asked her. "Well, we're not all a bunch of vacuous sluts," Ashleigh defended, her three-blowjob morning not withstanding.

The afternoon was monotonous. Around 3pm, the junior analysts dropped by Matt and Ashleigh's office and asked if they wanted to go out for drinks after work. Both accepted, although neither was 21 yet. Ashleigh had a fake ID that she carried around for just such an emergency, but she didn't exactly need the reputation of being a lush on her first day.

The analysts feigned surprise when Matt and Ashleigh told them they were underage. They knew full well, of course, but everything was part of the plan. Eventually, one of them, Mike, offered his place and some margaritas, which sounded fine. Mike left his car at work, and Ashleigh, who had taken the bus from her apartment, accepted a ride from a guy named Harvey, who volunteered to be the designated driver.

In Mike's apartment, Ashleigh surveyed his music collection and asked if she could put on some classic rock. Mike mixed up a pitcher of margaritas and offered a toast: "To Vernon ... may he rot in hell." Everyone eagerly toasted to that. They ordered some Chinese takeout, and had another round of margaritas. Afterwards a few of the guys lit up a doobie on the balcony, and Ashleigh joined them.

By 9pm, most of the guys feigned tiredness, and even though Ashleigh couldn't believe that they were actually ending (rather than starting) a party at that hour, she realized it was a Monday night and everyone had work in the morning. Mike offered a round of shots for the crew, pulling out his best bottle of whiskey. Everyone smiled a little as Ashleigh slammed her shot down without a second thought.

On the ride home, Ashleigh thought it a little strange that she felt so queasy after just three drinks. The guys all made fun of her for being a lightweight, but she insisted she could usually hold a lot more than that. Harvey helped the increasingly wobbly Ashleigh up the stairs to her apartment, and refused to let her pass out until he was sure that she got back to her place. Not out of chivalry, of course, but they wanted her to wake up in her own apartment.

--

Ashleigh's head pounded as she cracked her eyes open. She was vaguely aware that she was naked, kneeling in front of the couch, and that someone was fucking her from behind. She tried to lift her head, but couldn't. She tried to lift her arms, but couldn't.

--

The next time she cracked her eyes open, she was on her bed, on her back. Her knees were jammed to her chest as some fat douche came, and then collapsed on top of her. She muttered something incoherent and then fell back asleep.

--

Ashleigh was face-down on her bed, with her ass in the air and someone's dick in it. She could hear voices - lots of voices - in her room. They were celebrating or something. Someone spilled a drink on her carpet, and someone else said not to worry about it. The guy who was fucking her ass was making some weird grunting noises and announced he was cumming.

--

When Ashleigh woke up for real, it was 4:30 in the morning. She was wide awake, but her head was still swimming. She tried to stand up but immediately collapsed on the ground. She crawled over to the bathroom and vomited into the toilet, which didn't make her feel better. She reached down and felt her pussy and ass, both tender and a little sore. Did she fuck someone last night? Who?

What the hell happened?

Chapter 3

Per Ray's suggestion, she dressed a little sluttier - she had a tight white blouse, top buttons unbottoned, with a black, mid-thigh length skirt. Ashleigh thought she'd be the first one at work, arriving at 7:30. But Vernon was already there, making his cappuccino. "Ah, Ashleigh, you're here early. Let's get started so we can have the rest of the day free." He led her into his office and closed the door, marveling at her legs. "You know what? It's early. Let's use the extra time well." He motioned Ashleigh to the side of his desk, and then roughly bent her over the side. He reached up her skirt with one hand, feeling around her privates. "Garters, nice. Underwear, unnecessary." He yanked her panties down to her ankles, and Ashleigh stepped out of them.

Flipping her skirt over her ass, Vernon Bessie rubbed his dick up and down her crack. Both her asshole and her vagina felt loose, as if all the junior analysts that he had told to fuck her had all fucked her. Since she wasn't wet and he wasn't willing to wait until she was, he sprayed on a little lube and began fucking her from behind.

Ashleigh's body began responding, and soon enough she was pushing back against him in rhythm. Vernon took a few photographs of his dick sliding in and out of Ashleigh's teenage pussy, his rod glistening in the morning sun. When he was about to cum, he stopped and flipped Ashleigh over, laying her on her back on his desk. She wrapped her legs around his neck and he fucked her a little more while he opened up her blouse to play with her tits.

Eventually, he couldn't hold it back any more, and ordered her to kneel in front of him. Ashleigh scrambled to the ground and opened her mouth, letting her boss ejaculate into it. His cum was thin and dribbly, and Ashleigh couldn't tell whether it was just because he was old or he had a vasectomy. At any rate, it was over soon enough, and she straightened up her hair and clothes while he slumped in his chair, exhausted.

--

Ashleigh went to her office to try and get some work done, but the junior analysts were there. The conversation ground to a halt when she appeared around the corner, and they were all strangely unfriendly to her at first. But then she smiled and said hi, and they pretended to be concerned about her "hangover," and everything seemed okay. They still made fun of her for being a lightweight, and Ashleigh wanted to prove them wrong, but she was just getting a weird vibe from them.

As a matter of fact, the vibe got really weird later in the morning when all the junior analysts started cracking super sexual jokes around her. Jokes about her having sucked ten dicks in a night (which was true, but goddammit, they didn't know that), jokes about her scissoring with one of the accounting interns named Jen (which was totally plausible because Jen was fucking HOT, but goddammit, they didn't know that). Ashleigh actually started to get pretty annoyed by it, and went down to HR to complain about it.

Ashleigh knew better than to try the VP of human resources, who had made her give him a blowjob the day before. She snuck by his office and went to one of the directors, named Rick, according to the name on his door. She knocked and he called her to come in. As soon as she saw him, Ashleigh thought he looked familiar, but she couldn't put her finger on it. He was a balding man in his 40's, so it wasn't from school or anything, but she definitely remembered him.

"I'm having some trouble with my roommate," Ashleigh explained. "They're making weird sexual jokes about me, and I don't think it's appropriate."

"Well," beamed Rick, "What are some of the jokes?" He had a weird smirk on his face, like he recognized her too.

"You want me to repeat them?" asked Ashleigh, incredulous. "Well, for one thing, they called me a whore."

"And ...?"

"And I'm not!" protested Ashleigh. Rick seemed amused more than anything, and reached down to play with his cell phone. Ashleigh didn't realize what he was doing until her phone started ringing, and she looked at her phone with horror. A few months ago, in order to pay for her spring break trip, Ashleigh had posted an Internet ad. Being a dumb noobie, she had posted her real cell phone number, and now a bunch of pervs who paid to blow a load into her mouth or pussy had her number. And apparently, Rick was one of them. Ashleigh rejected the call.

"Follow me," Rick said. Rick led Ashleigh out of the HR department and down to the third floor, and Ashleigh groaned. MotherFUCKER! "I have a sneaking suspicion you've been here before," he commented as he opened the door to the men's room for her.

Rick took off his pants and sat down on the toilet, his rigid dick standing up in the air. He pulled Ashleigh over and sat her down on his lap, straddling his legs and facing him. Ashleigh sighed and unbuttoned her blouse, letting him paw at her bra-covered tits. He was gentle with her, appreciative even, as if he didn't get it very often. He reached back behind her and unclasped her bra, letting it fall down. Taking an engorged nipple into his mouth, he sucked on them, alternating.

As his dick got drooly, Ashleigh was afraid he was going to cum before he even put it inside of her (and get his jizz all over her clothes), so she stopped the proceedings and stood up to take off her panties. Pulling her skirt up to her waist, she straddled him again, jamming his dick inside of her. It didn't take long - after a few seconds of wild bucking, he started blubbering her name and released a big wad of cum into her. Ashleigh sat there, reaching down to milk the last few drops out of his cock, before standing up.

"So, can I switch offices or something?" she asked.

"No, each department only gets one room for interns. You have to stay where you are," Rick said.

"What the fuck?!" replied Ashleigh. "I just let you cum in my pussy. The least you could do is to give me a different room."

"You gave me a freebie so I wouldn't tell everyone in this company that you suck dick for money in your spare time," Rick corrected. "I never promised to help you. I'll see what I can do."

With that, Rick zipped up and left Ashleigh to scoop the cum out of her pussy. She wiped it down as best as she could, even wetting some paper towels with water, in an effort not to smell like she had just been fucked. After putting her panties back on, she checked her hair in the mirror and was about to leave when the door opened again, and Ray walked in with Rick behind him.

"Rick tells me that you don't like your officemates," Ray commented. He didn't waste any time, as soon as the door clicked behind him, he unbuckled his belt and gestured for Ashleigh to kneel down in front of him. Ashleigh gritted her teeth and did it, fishing Ray's dick out of his pants and stroking it with her fingers to get it hard.

"I'll tell you what I'm going to do," he continued. "I'll move you up here, to the third floor, to give you more room to spread out all your files." Ashleigh licked her lips and sucked him in with a little slurp. "Also, this way, you'll be closer to the bathroom here, so you won't waste too much time walking back and forth." Ashleigh bobbed her head up and down his dick, letting it slide back and forth across her tongue. She grabbed the base of the dick and matted down his pubic hair so it wouldn't tickle her nose.

Rick watched Ray's swollen member slide in and out of this intern slut and felt his dick harden again. He pulled Ashleigh to her feet, and like a pro, Ashleigh didn't even let Ray's dick slide out of her mouth. Pulling the crotch of Ashleigh's panties aside, he fingered her cunt until it was sopping wet, and then yanked out his own dick for a second helping of pussy.

Rick and Ray developed a rhythm, alternating between impaling Ashleigh on the cock behind her, and the cock in front of her. As they neared orgasm, though, both lost control of the rhythm, and Ashleigh found herself tossed about between two guys on the verge of cumming. Eventually, it was Rick who came first, pulling Ashleigh backward and shooting his second load as deep inside of her as he could manage. Ray had to take a step forward to get his dick into Ashleigh's mouth again, and unloaded a few streams of thick, stringy jizz into Ashleigh's mouth.

By the end of the day, Ashleigh's official office was the small conference room, and her unofficial office was the third floor men's room.

Chapter 4

Three weeks into her internship, Ashleigh had everything down to a routine. When she got in, she'd blow Vernon first in his office, and then Ray in his office. Rick would come by on his morning break to fuck her in the men's room, and again for his afternoon break for a blowjob. The VP of HR and the VP of Investor Relations usually alternated days, but they always asked for it around lunchtime, and almost always wanted her to suck them off. One of the senior analysts had caught her flushing a used condom down the toilet, so she let him dump a load into her every few days, and she had to fuck the janitor, too, to stop him from asking questions about why she was in the men's room all the time. She also realized that the junior analysts had roofied her, so she stopped hanging out with them, but Matt was cool, so she fucked him once in a while after work.