Desperate Measures: The Driver

Of course I've done this before. Eating pussy may not have been a popular thing to do back during the stone age when you were young, but times have changed. Tom held his breath and slipped his tongue between the folds of her pussy. Gwendolyn's nectar coated his tongue as he pushed it into her vagina. He stabbed it in and out of her several times, then licked his way to the top of her slit.

"Very nice," Gwendolyn cooed. "I like your technique."

Tom extended his tongue and the flicked the tip against Gwendolyn's clit. He swiped it across several times, flicking it from all directions.

"Mmmm, that's it Mr. Lowery. Lick my clit. Just like that."

Gwendolyn closed her thighs around Tom's skull. She reached both hands under the desk and pressed on Tom's head, pushing him deeper into her crotch. She tilted her hips and then raised them upward, increasing the friction of Tom's tongue on her tiny nub.

"Mmmmmm, just like that. Don't stop. Don't stop. Don't...stop."

Gwendolyn pushed on the back of Tom's head while she humped his face with her crotch. Tom licked her clit faster and faster, sucking the little button between his lips and swiping his tongue back and forth.

"Twenty...minutes...Mr. ... Lowery," Gwendolyn panted.

Tom sucked her clit for another minute, and then tilted his face downward. He licked the juice flowing from Gwendolyn's slit, pushed his tongue inside her, and then resumed his attack on her clit. He felt her pressing the back of his head into her crotch, while her hips rocked with increasing urgency.

"Fifteen...minutes...to... ahhhhhhhhhhhhh..." she cried, "...go."

Tom reached between his legs. He was surprised to find his cock was already hard again. He stroked it twice, and then let it go. I don't have time for that now. Tom slipped a finger between Gwendolyn's thighs and pushed it into her juicy hole. Damn! The old lady really gets wet. Gwendolyn clamped her thighs against Tom's head and squeezed.

"There's... no need... to hurry." Gwendolyn sighed. "You're doing...uhn...fine."

Gwendolyn eased the pressure on Tom's head. With the additional space to maneuver, Tom slid his finger in and out of her slippery tunnel. He probed the upper surface with his fingertip, searching for the rough patch of tender flesh that triggered so many of his ex-wife's orgasms. After several seconds of delicate probing, his finger found the hidden treasure.

Gwendolyn's response was instantaneous.

"Oh! Yes! That's it! Yes! I'm...cum...ming! Yes! Yes! Oh! Yes! Oh! Yes!"

Gwendolyn gripped the edge of the desk with both hands. She pushed her hips forward, grabbed Tom's hair, and pushed his face against her crotch. She humped his face and his probing finger, easing herself from one orgasm into another. When her second orgasm started to fade, she let go of Tom's head and collapsed in the chair. Tom removed his finger from her pussy and backed away from her crotch.

"I didn't tell you to stop, Mr. Lowery," Gwendolyn cautioned while pressing her thighs against Tom's head. "This test isn't over, yet."

"Didn't you cum?" Tom asked, his voice muffled by Gwendolyn's smooth, trembling thighs.

"Yes, I did. But I think I have one more in me. There's still ten minutes remaining on the clock. Let's see if you can help get the last one out."

Tom took a deep breath, slid his hands under Gwendolyn's butt cheeks, pulled her crotch against his face, and then buried his tongue in her pussy. He licked her from top to bottom, then rolled his tongue into a cylinder and slid it in and out of her vagina. Gwendolyn rocked her hips back and forth, rubbing her clit against Tom's nose.

"Ooooo! That's...yes! Don't stop. Just like that. Just..like... Unh! Yes!"

Tom sucked her lips into his mouth, slid his tongue over every slippery surface he encountered, and then zeroed in on her clit. He paused to take a deep breath, and then sucked the nub between his lips. He flicked his tongue over and around it, attacking the little button of flesh from every angle at the same time.

"Oh god! Oh yes! Mmmmmmm! Oh! Mmmmmmmm! Unh! Oh yessss!"

Gwendolyn's thighs spread as wide as her bunched skirt would allow. She grabbed the back of Tom's head and pulled his face away from her crotch.

"Enough! No more! I can't take any more! Enough!"

Tom crawled out from under the desk. Gwendolyn closed her eyes and gasped for breath. When her breathing slowed almost to normal, she sat up and smiled.

"Well done, Mr. Lowery, well done."

"Did I pass?"

"With flying colors. In fact, you may have earned the highest score ever on that particular test."

"Now that you've gotten your jollies, would you mind telling me what this is all about?"

"Very well. I usually wait until the formalities are completed before explaining the meaning behind this process, but so be it.

"Mr. Lowery, as you can plainly see, I am not a young woman. I married my husband at the age of eighteen. Mr. Garrity was thirty-six years of age at the time. I was sexually inexperienced, but Mr. Garrity was not. In fact, I was still a virgin on my wedding night. I won't go into details, but it will suffice to say that our wedding night was a disaster. My trepidation and inexperience were the causes of that catastrophe.

"It was several weeks before I had the courage to try again. Mr. Garrity was kind and patient, but the result was another debacle. I feared that I would never be able to perform my duty as a wife, and that my husband would cast me aside and return to his first wife. I was resolute in my determination to overcome my distaste for the sexual act, and to become the loving, sexually satisfying wife that my husband deserved.

"It took me ten years to become comfortable with my sexuality. I was already in my late twenties when I finally learned to enjoy sexual relations and became adept at pleasing my husband. For the next five years we made love like newlyweds. We celebrated our love in every room of the house–as well as in the fields, in the groves, in the barns, on the machinery–there was nowhere on this property where we did not pleasure each other in one way or another. It was the happiest period of my life.

"Unfortunately, all good things must come to an end, as they say. My husband's libido started to diminish just as my desire exploded. Our lovemaking dwindled from two or three times per day, to two or three times per week, to once a week, and finally to once or twice a month. There was no Viagra in those days, and I had no choice but to accept his reduced appetite for lovemaking. Of course, I had no problem finding privacy in an empty room in this house, and made due with self-gratification as my only means of sexual release. It was not as satisfying as my husband's attention, but it was something."

"Did you take a lover?"

"I was tempted, believe me. With all the farmhands and laborers on the property, there were always available candidates. But I did not wish to disrespect my husband, and so I never cheated on him. Of course, I did fantasize over many of the young men working for us. I often sat in this window and pleasured myself while watching the men, shirtless and sweating in the summer heat, unaware that while they were working on the farm I was flicking my bean and imagining all the things we could do to each other. I imagined them individually, in groups of two or three, or when I was particularly randy I imagined all of them taking their turns spilling their seed inside me.

"But I digress. I was in my mid-thirties when my husband suffered a stroke. He was in the hospital for several months, and when he returned he was never the same. He recovered enough that he could still manage the farm, but he could no longer work the fields in a hands-on capacity. Even more devastating, he could no longer plow my field. I was thirty-six years old the last time I made love to my husband.

"He held on for fourteen years, but he was never the same. Nonetheless, I remained faithful to him despite my growing sexual frustration. I believe that my husband recognized my sacrifice, and that is why he left nearly his entire estate to me.

"Anyway, I honored his memory for a year. By the time that year had elapsed, I was fifty-one years of age and had not had sex with a man in fifteen years. Unfortunately, I was ill-equipped to begin dating. The first man I met bedded me in no time and just as quickly connived a plot to steal the estate from me. Fortunately, my husband's accountants were monitoring my finances and alerted me to his scam before he did any serious damage.

"What happened to him?"

"He's in prison now. He left a string of bankrupt widows from California to Florida. I would have been number seven on his list if not for the accountants."

"Are these the same accountants who were responsible for the IRS problem?"

"No. I hired a new firm to manage my finances after the IRS debacle. The former accounting firm was well-intentioned, but they still fucked up, if I may be blunt. The new firm found no evidence of graft–just the one enormous error."

"I see."

"After that, I decided to be much more careful with the men in my life. Nonetheless, I attracted one lout after another. I finally realized that I was happy being a widow–all I needed were occasional sex partners. My best years were behind me, but every once in a while I still desired sexual release. I decided to confine my sexual encounters to my household staff. If I employed single, unattached men and women of impeccable character, who would work for me by day and be available to me in the evening, all my problems would be solved."

"Did you say men and women?"

"Yes, I did."

"When did you develop an interest in women?"

"That was a relatively recent development, actually. A few years ago I was getting a massage at a day spa when I noticed my pussy becoming moist. The beautiful young South American masseuse continued working my buttocks and thighs, and the heat between my legs became hotter and hotter. Finally, I rolled over and asked her to finish me."

"What did she do?"

"She laughed, and then covered me with a towel. So I made it clear that I was a regular customer and a very big tipper. She reached under the towel and fingered me to an astonishingly violent orgasm. I had to roll up the towel and bite down on it to keep myself from screaming. I have enjoyed the company of women ever since."

"Do you still see your masseuse?"

"I did, until she quit and moved away."

"Interesting."

"Do you have any more questions, Mr. Lowery?'

"Yes, I do. Let me see if I understand what you are saying. All of your household staff are also your occasional lovers, correct?"

"Yes, Mr. Lowery, that is correct."

"Does that include Wilson?"

"Of course."

"Ms. Webber?"

"Yes."

"How many others are on your staff?"

"There is an upstairs maid and a downstairs maid. The cook and the serving girl. The pool boy. I had a handyman, but when he resigned I decided not to replace him."

"So, that's four men and four women, including the driver?"

"Precisely."

"How often do you require the bedroom services of your staff?"

"It varies, but I try to spend some private time with each of them at least once per month. Sometimes more, sometimes less. There are also times when I loan the staff to guests. I have procured some rather sizeable donations to the Foundation after sharing members of my staff with a potential donor."

"I have just one more question."

"Go ahead."

"Could you explain to me why anyone would leave your employ? The handyman left, and the previous driver resigned? Why?"

"That's easy, Mr. Lowery. I require that my staff remain single. I don't care if you have outside relationships, so long as they don't interfere with your duties. But should you decide to get married, I will have to let you go. It's that simple."

"I see. Well, I guess you have made me an offer that I can't refuse. Hand me that contract, and I'll sign."

"Here's the contract." Gwendolyn handed a bound stack of papers to Tom. "I believe you already have a pen. Hold on a second while I call Ms. Webber in to witness."

Gwendolyn picked up the phone, and less than a minute later Cynthia walked through the door with a briefcase in one hand. Tom looked her over once again as she set the briefcase on the floor next to Gwendolyn's chair.

"Nice to see you again, Ms. Webber," Tom said.

"Thank you, Mr. Lowery. I'm very happy that you will be joining our staff."

"How long have you worked here?"

"I joined the staff a little over two years ago."

"Was your interview process..."

"The interview process is identical for all of my household staff, Mr. Lowery," Gwendolyn interjected.

"I see."

A bulge formed in Tom's pants as he imagined Cynthia sitting in the same chair that he occupied, her legs spread and her hands at work bringing herself to orgasm. His cock reached full erection when he pictured Cynthia beneath the desk on her hands and knees, her face buried in Gwendolyn's pussy.

"We're waiting, Mr. Lowery."

Gwendolyn's gentle rebuke snapped Tom out of his fantasy. He cleared his throat, skipped to the last page, and signed the agreement. He handed the gold pen to Cynthia, who once again bent over the desk and added her signature on the indicated line. She stood up, replaced the pen in the marble pen holder, and slid the agreement across the desk to Gwendolyn.

"That will be all, Ms. Webber," Gwendolyn said.

Cynthia turned and left the room.

"So, do I stay here tonight, or is Wilson going to drive me home now? Do I get a tour of the grounds? Can I see my room?"

"Not so fast, Mr. Lowery. There is still the matter of the third test. Once you complete the final exercise, you will be welcomed to my staff. Should you fail, however, you will be driven home and you will never hear from me again. Do you understand?"

"Yes ma'am. No problem. Should we go to the sofa, or would you prefer it bent over the desk?"

"You're being presumptuous, Mr. Lowery. Bent over the desk is indeed what I have in mind, but I will not be the one bowed over the furniture."

Gwendolyn stood up and reached for the zipper on the side of her skirt. She pulled it down, stepped out of the garment, and folded it over the back of her chair. Tom admired her smooth, toned legs and her glistening pussy visible beneath the neatly trimmed bush.

"Excuse me? I'm confused."

"Allow me to clarify matters for you."

Gwendolyn replaced the papers in the folder, and then moved the folder to the corner of the desk. She picked up the brief case, set it in the center of the desk, and opened it. She reached in, removed a small tube, and then handed it to Tom.

"Start lubing yourself up. You're going to need it."

Tom froze in his place. Neither his legs nor his arms seemed to work. His slack jaw and opened eyes revealed the extent of his dismay. After several seconds he managed to squeeze some lube onto his palm and apply it to his erect cock.

"When you're finished, hand me the tube. I like to apply a little myself before we get started."

Gwendolyn stepped out from behind the desk with a leather harness attached to a long, slender phallus-shaped implement in her hand.

"Whoa! What's that for?"

"Use your imagination, Mr. Lowery. I can only think of one purpose."

Gendolyn stepped through the leg openings and fastened the harness around her waist.

"You aren't using that thing on me. No way. Unh-uh."

"Mr. Lowery, all that is standing between poverty and financial security for yourself is fifteen more minutes of your time and eight inches of vinyl. Surely, you aren't going to throw away this opportunity over eight slender inches of vinyl, are you?"

"That thing is not going up my ass. No way."

"If you prefer, I could have Wilson administer the test. He's a bit bigger, I'm afraid, and quite a bit stronger. His method of testing is–how should I say it–more robust than mine. The choice is yours."

"No. I'm going home. Call me a cab. I don't want anything more to do with you people."

"Mr. Lowery, you disappoint me. We were so close to reaching a deal. After you did so well on the first two tests I was really looking forward to you joining our team. Is there anything I can do to change your mind?"

"Yes, Mrs. Garrity. Call off the testing."

"That's not an option, Mr. Lowery. All of my employees have been tested in the same way. It wouldn't be fair to them if I were to exempt you from the requirements of the job."

"How is it that you fucking me in the ass is a requirement of the job?"

"Mr. Lowery, I have developed an interest in various sexual practices. Some might call them deviant sexual practices. No matter, I overpay my staff so that they will be available to me whenever I want to indulge my interests. If you cannot meet my needs, then I have no use for you."

"But..."

Gwendolyn opened the folder and pulled out a check.

"Mr. Lowery, here is a check made out to you in the amount of $4583.33, minus required deductions for income taxes, FICA, etc. This is your first month's paycheck. I am paying you for the entire month, even though you would not be starting until the fifteenth. All you have to do is pass the final test."

Tom stared at the check. His face reddened and he started to sweat.

"I can't. I'm not a fag."

"It doesn't matter to me whether you are or you are not a homosexual, Mr. Lowery. This is not a test of your manhood. I have never hurt anyone, but I now have enemies–starting with my late husband's children and their mother. I have to know if I can trust you. This is a test of your loyalty and fidelity. It is a test of your willingness to do whatever it takes to please me. It is the ultimate test of your character, Mr. Lowery. Nothing more than that."

"But...

Gwendolyn reached into the folder one more time and retrieved another check.

"This check is made out to you in the amount of $5000. Consider it a signing bonus. It is my final offer. There is close to $10,000 dollars on the table in front of you. That's $9000 more than you had this morning. You must make a choice, Mr. Lowery, and you must make it now. Either pick up the checks and join my staff, or take your clothes and walk out that door with what you brought here. What's it going to be, Mr. Lowery?"

"I..."

"Decide now, Mr. Lowery. How are you going to support your children if you walk away from this opportunity?"

Tom's face twisted in agony. My kids. They aren't going to have health insurance in another week. Dammit, she knows my weakness.

"Can I..."

"No. All you can do is choose."

Tom's knuckles were white from wringing his hands. I'll never be able to pay for their college if I don't start working again.

"But..."

"We're done, Mr. Lowery. I'm sorry."

"Wait. Alright. I'll do it."

Tom walked over to the desk, bent at the waist, and pressed his face against the hard surface. His naked ass was pointing in Gwendolyn's direction.

"Have you sufficiently lubricated yourself?" Gwendolyn asked.

"Just a second."

Tom squeezed another dollop of clear gel into his palm and applied it to his anus.

"Let's get this over with. Please be gentle."

"I assure you, Mr. Lowery, I am not a brute. I'm a sixty-two year old widow. Now, relax."

Gwendolyn stood behind Tom and pressed the tip of her plastic penis against Tom's anus.

"There's a timer on the computer screen. When you're ready, just hit enter with your dry hand, take a deep breath, and let it out slowly."

Tom followed her instructions. A timer displaying "15:00" appeared on the computer screen, and then started counting backward. Gwendolyn placed her hands on Tom's hips and pushed.

"Oh god! Fuck!"

"Relax, Mr. Lowery, it will only hurt for a minute or two."