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The Assistant

Category: Mature
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Vanessa Perry sipped coffee from her mug as she looked out at the summer sun rising over Philadelphia. The forty-year-old executive sighed deeply as she reflected back on her life. She had grown up the youngest daughter of an extremely wealthy family. She had dreams of growing up, falling in love and getting married, like her four siblings before her. However, as she watched their families evolve before her eyes, it became clear that that was not the life she wanted to lead.

So she left her small suburban home, made her way through college (relying on minimal financial assistance along the way) and spent the next fifteen years working her way to the top of one of the most prestigious medical research companies in the country.

All her corporate success had come at a significant cost to her personal life, however. She had been in a couple relationships, to be sure, but they never amounted to anything of substance, more due to her absorbing herself in her work. Now that she actually had some free time to focus on them, she was beginning to feel those sexual urges that she should have been feeling a long time ago. But the singles scene was absolutely dead; most of the men she met were either way out of shape (working out had been the only leisure activity she allowed herself, and only because the building she worked in had a company gym); wrapped up in their own careers, as she had been; or had any other of a number of issues that were common in men her age.

To hopefully bring an end to her problem, she put an employment ad in the newspaper for a “personal assistant.” She envisioned that whoever she found qualified to fill the position would be young, extremely good looking, intelligent, and an all-around gentleman. All the applications she received, however, proved her wrong. There were some that were attractive enough, but had no education; then came the smart but ugly ones. Day after day of sifting through packet after packet convinced Vanessa that she would never find the solution to her problem.


Astacio Vega pulled the classified section out of his morning paper. Having just finished college, he was looking for a job that could make use of his newfound skills, or at least pay the bills until he found one. He had been searching for a couple days now when he stumbled across a position for a “personal assistant.” The ad read: “‘WANTED: PERSONAL ASSISTANT’ Position available for personal assistant to V. Perry, CEO, LifeTech Industries. Applications must be requested in person at: LTI Center City Field Office, 16th and Chestnut, 17th floor. Pay starts at $2500/wk.”

Astacio couldn’t believe it. He’d wanted to work at LifeTech ever since he was in high school. Although it wasn’t quite a position that he’d ever envisioned taking, it would get him inside the company at least. He continued reading, and that’s when things got weird: “Applicants must be physically fit, attractive men between the ages of 21 and 27, and must submit at least two (2) 5×7 photographs with their application. Other requirements to be explained during interview.” What kind of position was this where the core requirements were one’s looks? And just what did they mean by “other requirements?” Then again, if that were the case, Astacio wouldn’t have any problems at all: he had served four years in the Army, where his physique had gone from wimp to ripped, and he took perilous care to maintain it. He figured, what the hell, one more job application wouldn’t hurt.


After only two weeks of running her ad in the paper, Vanessa was at her wit’s end. None of the applicants so far resembled anything close to what she was looking for. Then her secretary Emily knocked at the door.

“Come in.”

“Miss Perry, you got another applicant. This one decided to drop his packet off personally.”

“Oh really?”

“Yeah. I can’t say much, but I will say this: if you don’t at least give him an interview, you may as well just shelve this whole thing.”

Vanessa chuckled. “Thank you, I’ll keep that in mind.” She took the manila envelope from Emily and closed the door behind her as she left. Vanessa then sat down with the packet, and noticed that it was considerably heavier than any she’d previously received. She opened the envelope and read the application first. It said that the applicant was 25 years old, 6’3″, 195 pounds, a former U.S. Army Biomedical Equipment Technician who had just received his Associate’s degree in the same field. The vocabulary used in some of the personal question imparted his intelligence as well. She wasn’t quite sold on this guy at that point, but what his words didn’t say, his photos did. He had enclosed seven 8x10s with his application, some in his military uniform, some in street clothes, even one with no shirt on! She made two phone calls: one to the applicant to set up an interview, and the other to the newspaper to pull her ad!


Astacio got home about half an hour after dropping his application off at LifeTech, and there was a message on his answering machine. He couldn’t believe his ears when he played it back; it was Miss Perry from LifeTech asking him to call her secretary to arrange an interview! He immediately called back and set up a meeting at 7:30 dinner meeting. When asked where he should meet Vanessa, Emily told him that someone would be by his house to pick him up, citing security reasons. Astacio accepted that, figuring the job was his giving the quickness of the response.

That evening, 7:30 saw Astacio sitting out on his front porch waiting for his ride. At exactly 7:30, a black Mercedes pulled up in front of his apartment. This was a sight seldom seen in this part of the city, so Astacio knew it was for him. The back door opened, so he took that as a cue to sit there. Emily was waiting for him.

“Good evening, Mr. Vega.”

“Good evening. So, where are we headed?”

“You’ll see when we get there. In the meantime, I’ve been assigned to brief you as to the responsibilities of the position you’re seeking.” She had an unwavering professionalism to her, which is why Vanessa trusted her more than anyone else outside her family.

“Yeah, I’ve kind of been wondering exactly what it is that a personal assistant does anyway.”

“Well, first off, tell me a little something: What do you know about Vanessa Perry?”

“She’s the most successful woman in this city. She’s the CEO of LifeTech, a biomed firm I’ve wanted to work at for the past ten years. She’s originally from Upper Darby, but other than that, I don’t know a lot about her personally.”

“OK, no problem. That’s where I fill you in. You see, you were right in that Miss Perry is an extremely successful woman. She’s richer than 90 percent of the corporation heads in Philadelphia, and she also holds a great deal of political pull. She’s also never been married, which is understandable; she didn’t want to have to balance a family and her own ambitions. Now she’s forty years old and quite lonely.”

“I think I’m coming around here…”

“Miss Perry is a normal woman with normal physical needs, but since she doesn’t have the time for a regular relationship, she decided to hire a young man to be her companion.”

“OK, I get it now. She’s going to pay me to sleep with her, and that’s it?”

“Oh no, not at all. Although you will be having sex with her, your position as her personal assistant will entail traveling and dining together as well. Who knows, maybe once you get to know each other well enough, you may even help her out in the office.”

“OK, I’m with you on all that, but I’m still up in the air about one thing: the ‘other requirements’ mentioned in the ad?”

“Calm down, we’re getting there. Miss Perry is extremely driven to succeed, and like most driven people, her sex drive can at times be enormous!”

“Okay, she likes a lot of sex,” Astacio replied, “so do I, what’s your point?”

Emily shifted in her seat. “Well, much like any normal woman, Vanessa Perry is addicted to big cocks, and she has given me the, ummm, task, of measuring yours. Now, if you have any problems with that, I can have the driver take you back to your house right away, but if you want the job, then I’m gonna have to ask you to whip it out!”

Makes sense enough, Astacio thought as he unzipped his pants, letting his growing erection push its way through his fly. Emily was stunned; she’d seen a fair share of dicks in her twenty-eight years, but she had never seen one that big. She fumbled around in her bag for a few moments before producing a tape measure. She measured Astacio’s manhood at nine and a half inches long. “Oh, I definitely think you’ll do!” she said excitedly as she stroked it.

“Well, I never really knew how big it was, but I can’t say I’ve ever had any complaints.”

Emily said nothing; she just continued to stroke Astacio almost absentmindedly. Before Astacio could say anything, the car stopped. “We’re here,” said the driver.

Shit, Astacio said forcing his hard-on back into his pants as he exited the vehicle. They were in an underground parking garage that sat below the 56-story Citizen’s Bank Tower, the second largest building in the city. He and Emily got in the elevator and Emily hit the button for the top floor. Astacio was relieved; the long ride would give his wood time to subside back into his pants. Emily also gave him a last minute bit of information: “Oh, and one more thing: she’ll push you to see how much you’ll take, and if you let her walk all over you she’ll end up despising you as weak and worthless, so while I don’t recommend acting like a jerk or anything, don’t take any of her guff either!” Astacio was just about to thank her for the advice when the car suddenly slowed to a halt and the door slid silently open, exposing the two of them to vast expanse that was Vanessa Perry’s apartment.

“Emily, Mr. Vega, would the two of you join me for a drink?” came a voice from across the room. Emily led Astacio to a table next to a window which offered a fantastic view of the Philadelphia skyline. Vanessa joined them shortly, pouring a glass of wine for each. After going over Astacio’s packet with Vanessa, Emily left the two alone to finish the interview.

“So, relax and tell me a little bit about yourself, Mr. Vega.”

“Well, first off Miss Perry, I’d feel a lot more relaxed if you would call me Astacio.”

“All right then, Astacio, but only if you agree to call me Vanessa.”

“Agreed, Vanessa. I’m really not that good at talking about my own qualities; I prefer to have my actions speak for me in that regard.”

“Really? You certainly burned enough trees with your application.”

“Those are accomplishments. Factual occurrences. Nobody can say I didn’t do Things A, B, and C, because I, in fact, did Things A, B, and C, if you get my meaning.”

“I certainly do. You show wisdom beyond your years.”

“My point exactly. I didn’t have to tell you that, you judged it for yourself.”

The two talked until sundown. Vanessa was happy. She had found someone who was a good conversationalist, and also not afraid to give advice. He was also honest; she could ask him anything and know that he wouldn’t just say what she wanted to hear. Meanwhile, Astacio was still taking stock of Vanessa. She had a knockout body, with two gorgeous breasts that seemed to be standing up on their own. Her nipples pushed to the surface of her silk robe, betraying that she wasn’t wearing a bra. Never mind how beautiful she was; she was also witty and charming, and willing to listen to his old war stories, which she was constantly asking him to tell. Eventually she excused herself to her bedroom, and came back wearing a two-piece bathing suit. “I’m going out to the hot tub. You can join me if you’d like, or you can keep the couch company, whichever you prefer.”

Astacio grinned; sarcasm was a huge turn on for him. He joined her on the patio, but hesitated when she asked him to get in the tub.

“What, didn’t you bring a bathing suit?”

“No, I think I dropped it at my last job interview.”

Vanessa laughed. “Well, if it makes you feel any better…” She tossed her bikini bottom onto the deck. Astacio couldn’t help but grin. He stripped down naked and climbed into the Jacuzzi across from Vanessa.

“So, let’s get down to business shall we? I will admit, this isn’t the most conventional job interview I’ve ever been on.”

“That’s ‘cuz I’m no conventional woman, and this is no conventional job. In fact, I don’t even like to think of it as a job at all as much as a position.”

“Right, because from what I understand so far, there’s not gonna be a lot of work involved with this position, right?”

Vanessa moved around next to Astacio. “That’s certainly one way of putting it.” She ran her hands all over his body, before taking his fully erect member in her hands. “So, Emily tells me that you’re… shall we say, overqualified, for a position like this?”

“You tell me.”

“Mmm, and so humble about it. I like you, I really like you.” She turned to face him and threw her arms around his neck. Astacio returned the gesture by putting his arms around Vanessa, kissing her deeply as he held her to his chest. Her pussy was getting hotter by the second, and she was literally radiating heat from between her legs, through the water, and seemingly directly at his cock.

Vanessa ground her snatch against Astacio’s abs. “Can you feel me, how hot I am for you? Do you feel my pussy’s heat for your big, young cock?” she breathed in his ear.

Astacio uttered a barely audible ‘yes’ as he nuzzled her neck.

“Then give me that cock, baby, show me what you can do with that dick.”

“Are you used to people giving what you want?”

Vanessa pulled back and looked Astacio square in the eye. “Listen, young man, what I want, I take,” she said with a sultry, yet commanding tone.

With just as much authority in his voice and a grin on his face, Astacio retorted, “Then I suggest if you want that dick, you learn to take it.”

“Oh, OK, I see how it is. Then from here on out, this dick is mine. It goes in my pussy, my mouth, my ass, and no one else’s unless I say so. Are we clear, Mr. Vega?”

“Perfectly.” Without so much as another word, Vanessa grabbed the young man’s dick and impaled her cunt on it. She wrapped her limbs around his torso as he fucked her like the young stud she had been looking for. Astacio was in heaven himself. He had fucked older women before, but none of them could hold a candle to the beauty he was slamming his cock into. He fucked her shallow, deep, hard, slow, fast, any way he possibly could. She soon came violently, digging her nails into the flesh of his back and letting out a throaty moan loud enough to be heard throughout the entire city!

Astacio held her in his arms, gently kissing and caressing her. She wasn’t in the mood for any loving yet, though; she had come several times, now she wanted to feel him come for her.

“Take me into the bedroom,” she ordered him.

“Not a problem.” Astacio climbed out of the hot tub, then jogged, with Vanessa still mounted on his pole, into the bedroom, causing her to let out a moan every time she spiked down onto him. Once in her bedroom, Astacio proceeded to fuck her again before she pushed him away. Astacio was a little bewildered, but all questions were answered when she got on all fours, thrusting her ass lewdly backwards at him. That was all the hint he needed, sliding gently this time into her still burning cunt.

Vanessa was in overwhelming ecstasy as she gyrated her hips to meet her stud’s thrusts. Never before had she met anybody who so ably made her feel like a woman; who made her feel so completely in control yet helpless at the same time. Astacio felt her snatch spasm with another spate of orgasms before feeling his own building up in his loins. It seemed Vanessa could feel it as well: “Are you ready to cum now?”

“Oh, yeah… where do you want it?”

“Cum in my mouth, I want to taste your young spunk.” She turned around and jerked Astacio’s pecker until he had a mind-numbing climax, and she dutifully swallowed every drop of his cum. Now too weak to stand, Astacio dropped down on the bed. Vanessa snuggled up to him. “Well, I think the interview went well, don’t you? I don’t know who’s going to enjoy your job more, you or me!”

“I thought we had agreed to call it a position.”

“Hmm… true, true…”

Astacio’s dick was already stiffening again. “Speaking of positions, I’ve got one in mind for you.”

“Oh really? What’s it called?”

“This one’s called the Baby Maker, due to the fact that it results in 100% penetration. More depth means less distance for the sperm to travel, which means higher likelihood of survival and thus, pregnancy. Here’s hoping you’re on the pill.”

“Wow… good thing I am,” Vanessa said as Astacio turned her on her side. He straddled one of her legs, lifted the other over his shoulder, and pushed his cock halfway into her. Just as Vanessa was beginning to wonder where all this ‘100% penetration’ was, Astacio grabbed her by the hips and pulled her with all his might towards him, pulling her cunt lips against his groin. Vanessa screamed at the top of her lungs; she’d thought he was big before, but feeling that cock being pushed almost through her cervix was more than she’d expected! He held onto her, moving only his hips, causing her to writhe in ecstasy. Eventually she cried out, “My god in heaven, Astacio, I’m coming again!” Vanessa’s pussy clenched down like a vise on Astacio’s dick, causing him to scream as he swelled up, before filling Vanessa with every drop of cum he had conceivably stored in his body, to the point that it flowed out onto the sheets!

Vanessa struggled to get her legs under her, but collapsed as soon as she set her feet on the floor. As Astacio helped her up, she spat, “Mr. Vega, I have just two words for you: You’re hired!”

Astacio smiled. “Miss Perry, I think I’m gonna enjoy working for you just fine.”

“As true as that may be,” Vanessa replied, “I have a feeling I’m gonna enjoy working with you even more!”


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