Desperate Measures: The Driver

Gwendolyn's smile returned. She's genuinely proud of her work. This is much more than a tax shelter for her.

"That's commendable. But why do you need a driver?"

"That's simple, Mr. Lowery. I don't like to drive. I have an office on Brickell Avenue, but it's over an hour drive each way. That's time I could spend working, talking to donors, or just relaxing with a cold beverage."

"That makes sense."

"Also, I get sleepy when I drive–especially at night." Gwendolyn smirked.

"The car you would be driving is the same Mercedes that brought you here. It's a 2002 model with 400 horsepower, if that makes a difference to you. It was the first thing I purchased when the lawsuit concluded.

"For the most part, I need to be driven from here to the office and back two or three days per week. I travel once or twice per month, so I will need transportation to and from the airport. If I should have an event in the evening, I will require your services then, as well. And of course, for any shopping or other activities I should schedule on the weekends. In addition, you will drive the maid or Miss Webber to the store to purchase groceries and household items as needs require."

"I see. In that case, what are the hours?"

"Good question, Mr. Lowery. From what I have just described as the job duties, you can see that the hours are somewhat irregular. The average work day will comprise at most two to three hours of actual driving. However, I will require your availability twenty-four hours per day, six days per week. The one day off will vary from week to week, depending upon my schedule."

"So, am I supposed to just sit at home and wait for you to call and tell me where and when to pick you up?" Tom frowned.

"Would you have a problem with that?" Gwendolyn arched an eyebrow.

"Yes...no...I mean...is that normal?" Tom squirmed in his chair.

"I'm teasing you, Mr. Lowery."

Tom exhaled.

"You will live here. In fact, all of my household staff lives here. Except for your day off, the rest of the time you will wait here until I require your services."

"Live here? In the middle of nowhere?"

"I assure you, Mr. Lowery, it is not as intolerable as you may believe. This is a walled estate with twenty acres of landscaped tropical paradise. We have an Olympic-sized pool, a hot tub and sauna, and an expansive deck. We have a weight and fitness room. There is a putting green, biking trails, and a stable with six horses. I recently signed a contract for the installation of tennis courts this summer. You have never lived in such comfort at any time in your life."

"Is the housing expense deducted from the salary?" Tom raised one eyebrow.

"Of course not, Mr. Lowery. That is one of the fringe benefits of working for me. Not only do you live in luxury, but it is entirely free of charge. Just think of how much money you will be saving when you do not have to pay rent, electricity, or water and sewage."

Tom leaned forward in his chair.

"How much is the salary?"

Gwendolyn frowned.

"I am a little disappointed, Mr. Lowery. I had hoped that we would be further along in our discussion before the issue of money reared its ugly head."

"I'm sorry to disappoint you, Mrs. Garrity, but it is a matter of some importance to me."

"I'm quite aware of your circumstances, Mr. Lowery. You are thirty-five years of age. You have been out of work for six months. You were a beat writer with the local newspaper, but dwindling subscriptions have led to downsizing. Despite working there for twelve years and winning numerous awards, your job was eliminated and you have not been able to find any work since. Your wife divorced you immediately after you lost your job. She and your two children are living in the home of her fiancee, and she is planning a destination wedding in St. Thomas next Valentine's Day. Oh, you didn't know that last bit of information, did you? I'm sorry, Mr. Lowery, very sorry. In addition, your unemployment benefits are about to expire, and your child support payment is two weeks past due. Your credit cards have been cancelled, you have less than five hundred dollars in the bank, and your electricity is going to be shut off on Monday. Is there anything I am missing?"

Tom sat upright, his face frozen in shock.

"That's pretty thorough. How did you get all of that information?"

"I have my resources, Mr. Lowery. I know people who can find out things for me. It is very important for a woman in my position to be ultra-careful when bringing new people into my home."

"I see. Well, you probably already know everything about me already. But you still haven't told me the salary for this job."

"I assure you, Mr. Lowery, you will find the salary sufficient."

"Now you are just taunting me, Mrs. Garrity."

"Not at all, Mr. Lowery. I have done my research. The average starting salary for a driver with no experience is $25,000. The maximum salary in this market is $45,000. I am prepared to offer you $50,000 if you can start tomorrow."

Tom's eyes bulged.

"Fifty thousand? I'll take it."

"Not so fast, Mr. Lowery. We still have a process to complete. I must finish what my advisors call 'due diligence.'"

"Fire away. I'll tell you anything you want to know."

"Actually, we are finished with the interview portion, Mr. Lowery. In this next phase, I have three tests for you. If you successfully complete all three tests to my satisfaction, then the job is yours."

"Tests? Great. Give me the keys, and I'll show you what I can do behind the wheel."

"These are not driving tests. I am sure that you can drive a car. I checked your driving record with the Department of Motor Vehicles. And to tell you the truth, the Mercedes practically drives itself. Mr. Lowery, these are tests of your character."

Tom shifted in his seat.

"Character tests?"

"Precisely. Each measures a different component of your personality. They are not too difficult, I assure you. But they do tell me if you are the type of person whom I want to bring into my home."

"OK. Let's go."

"I appreciate your enthusiasm, Mr. Lowery. Before we begin, let me remind you of the non-disclosure agreement that you signed previously. The terms of that agreement specifically cover every aspect of this interview, including the tests that you are about to undergo. Do you have any questions?"

"No–none. Let's get started."

Tom leaned forward in his seat, rubbing his palms on his knees.

"One more thing, Mr. Lowery. You will only get one chance to complete each exercise. If you should fail the test or fail to complete it in the time allowed, then the interview will be terminated and you will be dismissed. You will not get a second chance–ever. Are we clear?"

"Yes."

"Excellent. Alright, Mr. Lowery, take off your pants and masturbate for me. You have fifteen minutes to ejaculate, starting now."

"What? Is this a joke? You are kidding, right?"

"You are wasting time, Mr. Lowery. I suggest that you get started immediately. If you refuse the test, or if you fail to complete the task on time, then I will have to ask you to leave and never return."

"But..."

"You are running out of time, and I am running out of patience. Either take your pants off or leave my office. Now."

Tom hesitated. I need this. I'm on the verge of bankruptcy. I need to work. It's not a writing job, but the pay is better and I can still write in my spare time. It's almost too good to be true. Tom leaned forward and untied his shoes. He kicked them off his feet, stood up, and took off his pants and underwear. He wrapped his hand around his flaccid manhood and squeezed.

"Sit down and make yourself comfortable. You have fourteen minutes remaining."

Tom spread his legs in the padded chair and stroked his cock. It didn't respond.

"Mr. Lowery, I appreciate the difficulty you are experiencing. This may help."

Gwendolyn turned her computer so that the screen was facing Tom. She hit the 'enter' key and a video started playing. A naked, bosomy bottle-blonde woman was on her hands and knees while a tall, African-American man knelt behind her. He was also naked. The man worked his enormous cock into the woman's shaved pussy, and then fucked her at a furious pace. The woman responded to his thrusts immediately. Her lust-filled cries exploded from the speaker, filling the room with her pleasure. Tom felt his cock swell as the erotic action unfolded on the screen before him.

"That's better, Mr. Lowery." Gwendolyn's eyes sparkled. "You have eleven minutes."

Tom looked away from Gwendolyn and stared at the screen. Time was running out, and he had to focus on the task at hand without regard to his circumstances. He stroked his erect cock in an up and down motion, concentrating on the destination without regard to the journey. He preferred to take his time and prolong the pleasure, but Gwendolyn was not affording him that luxury.

Tom looked up from the screen and glanced in Gwendolyn's direction. A mischievous smile crept across her face as she stared in the direction of Tom's groin. Through her parted lips Tom could just see the tip of her tongue as it flicked up and down behind her teeth. The old lady's enjoying this. I wonder if I it's my cock that she finds so interesting, or if she just likes watching younger men jack off. Maybe I should slow down and give her more of a show.

Tom slowed his stroking and glanced back to the screen. No stranger to viewing porn, Tom recognized the video as an amateur production with unknown participants. The camera angles were all wrong for a professionally produced video. The actors were in positions that afforded maximum pleasure but less than optimal views of the woman's body and face, and her orgasms both looked and sounded genuine. Tom preferred amateur videos for that reason. Although not a fan of interracial porn, the action in this video was hot enough that Tom found himself hurtling toward self-induced ejaculation in record time.

"Five minutes, Mr. Lowery."

Tom glanced at Gwendolyn for a second. She was still staring at his crotch, but she was fidgeting in her chair. Both of her hands rested on top of the desk, but her polished fingernails clicked against the glossy wooden surface at irregular intervals. She's struggling not to move. She wants to touch herself. Or, maybe she's worried that I won't finish in time.

Tom's erection swelled as he considered the older woman's apparent arousal. A slight smile creased his lips. The old cougar–hell, she's practically a saber-toothed tiger–likes younger prey. I"m not sure if that turns me on, or if it creeps me out.

He returned his gaze to the screen. The black man slapped the blonde woman's ass, and then disengaged from her. The woman turned over and laid on her back with her legs sticking straight up in the air. Tom got his first good look at the woman's face. She's gorgeous. I could fuck that all night long. He stared at the screen as the man knelt between her legs, lifted her ankles onto his shoulders, and then speared her with his long, fat cock. The woman screamed as she urged her lover to fuck her harder and deeper with his enormous cock.

The male performer looked somewhat familiar, but just as Tom was searching his memory for a match, the camera angle shifted away and focused on the blonde. Tom's cock swelled as the young woman's unadorned sexuality filled the screen. Her face was a mask of pure pleasure–her pale skin was flushed, beads of perspiration dotted her forehead, her eyes were squeezed shut, and her jaw was clenched in a rictus of lust. Tom knew that she was about to explode in a massive orgasm, and he was on pace to join her.

"One minute," Gwendolyn panted.

Tom glanced from the screen and saw that Gwendolyn also appeared flushed. She can't wait to see me shoot. I think she wants to cum, also.

The blonde's grunts and groans filled the space between Tom's ears. He felt his cock swell and his balls contract. A load of semen shot up his shaft, exploded from the tip, and landed on the rug beneath his feet. He continued stroking as the camera panned down the woman's body, her chest heaving and her belly rising up and down while she sucked air into her lungs. The camera stopped at her gaping pussy, the shaved mound spread open as a river of semen flowed from within and spread out on the sheet beneath her buttocks. The last of Tom's load dripped onto the floor as the image on the screen dissolved to black.

"Very good, Mr. Lowery," Gwendolyn gasped. "Well done. You finished just in time."

Gwendolyn reached a trembling hand into the credenza behind her desk and pulled out a box of tissues.

"Here you are." She handed the box to Tom. "Take some tissues and clean yourself up. When you are ready, we'll proceed to the next test."

Tom reached for the box and set it on the table next to his chair. He grabbed a handful of tissues and cleaned the residual cum from his hands, cock and balls.

"What about this mess on the floor?" he asked.

"Don't worry, I'll have someone clean that up when we are through."

"We are through, Mrs. Garrity. I don't know what that was all about, but it is no part of any interview process I have ever experienced. I'm no lawyer, but I'm pretty sure that was totally illegal."

"Mr. Lowery, I admit that my methods are somewhat unconventional. However, bear in mind that this is an opportunity unlike any you have ever been offered. If we can come to terms, you will receive a generous salary while doing very little work, and you will be living in my home as a bonus. I am quite confident in stating that never again will you receive an offer like this one. Think very carefully before you turn it aside."

"That may be true, Mrs. Garrity, but my dignity is not for sale at any price."

"Mr. Lowery, everyone has a price. Everyone. We have already determined that your price is $50,000. I am prepared to meet that price. Tell me, is there anyone else making you a similar offer?"

"You already know the answer to that question." Tom looked down at his shrinking cock. "No, no one has made me an offer anywhere close to that."

"Very good. Shall we proceed to the next test?"

"I'm sorry, Mrs. Garrity. I don't think that I am the person you are looking for to take this position."

A tear formed in the corner of Tom's eye. He wiped it with a fresh tissue, and then leaned over and reached for his underwear and socks. This is just too weird. I need the job, but not like this.

Gwendolyn opened the folder and took out another stack of papers.

"Mr. Lowery, my attorneys prepared an employment contract with your name on it. It is dated with today's date and it takes effect at the conclusion of this interview. I anticipated your reluctance, so I made a counter-offer within the contract. If you will take a look at paragraph number four, you will see that the base salary is $55,000 per year, with annual cost of living increases and the opportunity for year-end bonuses. Of course, your cost of living is nothing since you will be living on my estate, but the point is that annual raises are already built into the agreement. In addition, I will pay off the balance on your current lease, bring your child support arrearage up-to-date, and provide manpower to move your possessions into your room. My signature is already on the last page. All you have to do, Mr. Lowery, is successfully complete the interview process and sign the agreement."

Tom gulped. His head was spinning, and he wanted to throw up. This is all happening too fast. I need time to think this over. He tried to stand, but his legs wouldn't function.

"Here is my pen, Mr. Lowery."

Gwendolyn reached across the desk to hand the pen to Tom, but it slipped from her fingers, rolled off the desk, and fell to the floor.

"I'm sorry, Mr. Lowery, would you pick up my pen for me?"

Without stopping to consider his actions, Tom slid from his chair and crawled under the desk on his hands and knees. He located the pen a few inches from Gwendolyn's feet, picked it up, and raised his head. He wasn't prepared for what he saw next. Gwendolyn's knees were spread apart, providing an unobstructed view up her skirt–all the way to her naked crotch. Tom gulped.

"Don't move, Mr. Lowery."

"Ma'am?"

"You heard me clearly enough. Mr. Lowery, tell me what you see."

"I, uh, I see your gold pen next to your very expensive well-polished shoes. I think they are what my ex-wife called 'slingbacks.' Um, ah, they are resting on this very elegant Persian rug..."

"Mr. Lowery, please don't lie to me."

"I'm not lying, ma'am."

"Mr. Lowery, I am not a stupid woman, and I would appreciate it very much if you stopped acting as though I am. You have already demonstrated to me that you are a young, healthy, heterosexual male. As such, you and I both know where you are looking. In fact, you are unable to look anywhere else. Your biology will not permit it. You are looking at my pussy, Mr. Lowery. Please don't deny it."

"Yes ma'am."

"Yes what?"

"Yes, I am looking at your pussy, Mrs. Garrity."

"Thank you for your honesty, Mr. Lowery. I expect nothing less from you."

Tom started to back out from beneath the desk.

"I assume this interview is now over?" he asked.

"Not at all, Mr. Lowery. I would have been very disappointed if you were not looking up my skirt. And I would have been even more disappointed if you had continued to lie about it."

"Then, was that the second test?"

"Heavens no. Placing a pussy in front of your face and asking whether you can see it may be an interesting exercise for your optometrist, but it merely serves as the introduction to the next phase of this interview. For your next test, you are to lick my pussy until I attain orgasm. You have thirty minutes, starting now."

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"Mrs. Garrity?"

"I believe I was quite clear, Mr. Lowery. Start licking me. You do know how to perform cunnilingus, don't you? Your wife didn't leave you because you refused to go down on her, did she?"

"Uh, no."

"Then stop wasting time. Unless you want me to tear this contract into pieces, have you escorted from my office, and driven to your soon-to-be dark and very warm home, then you will get started immediately. I am losing my patience, and when that happens my desire diminishes."

This is insane. Or a bad dream. I'm being sexually harassed by a senior citizen. A wealthy senior citizen with a job opening–a job I can't turn down. I don't have any god damned choice. I just hope that dried up, fossilized old pussy can still cum.

Gwendolyn reached under her chair and located the handle locking the back into place. She pulled the handle, reclined the chair, slid her hips to the edge of the seat, and spread her knees another six inches. Tom eyed the pink lips protruding from her sparse bush, closed his eyes, and crawled toward her.

Starting at her knees, Tom kissed the insides of her thighs and worked his way toward her crotch. At least her legs are smooth, and they are still rather firm despite her age. Why shouldn't they be? She is still an attractive woman. Tom hesitated when he reached her pussy. He kissed all around her mound for several seconds, trying to work up the courage to make his final approach. She isn't as hairy as I expected, and she smells surprisingly fresh.

"Twenty-five minutes, Mr. Lowery. I'll keep you updated on the time, since you can't see the clock from where you are."

Well, here goes nothing. Tom extended his tongue and licked her inner lips. With the tip of his tongue making as little contact as possible, Tom licked up one side and down the other. He repeated this process several times, lengthening his stroke with every turn.

"I like that, Mr. Lowery. It does seem as though you have done this before."