Adventures of a Part Time Sugar Baby

by Chessman

Caution: This contains strong sexual content, including Consensual, Slavery, Exhibitionism, Workplace, Nudism, .

Desc: : “Adventurous female redheads wanted for a six month employment contract. Applicants must be natural redheads and willing to prove that status at the time of their interview. Sugar babies welcome” Is a vague ad in the extreme, who knows what the author sought and what the heck is a sugar baby? The post office box to send resume and head shot was included in the ad and as I had not found work in my field since graduating my very expensive college, I responded.

The Job Interview

I answered the advertisement with a bit of hesitation in my mind. After all a Village Voice personals ad that reads: "Adventurous female redheads wanted for a six month employment contract. Applicants must be natural redheads and willing to prove that status at the time of their interview. Sugar babies welcome" Is a vague ad in the extreme, who knows what the author sought and what the heck is a sugar baby? The post office box to send resume and head shot was included in the ad and as I had not found work in my field since graduating my very expensive college, I responded.

Two days later an envelope came to my post box. It looked like the type of invitation a couple sends to invite you to a wedding or to some fancy party. "Mark J. Chessman cordially invites you to audition for employment at 0900 hrs 23 January. Waldorf Tower Suites number 1423. Lateness will disqualify the applicant immediately."

A ninety-minute bus and subway ride brought me to the door of the suite at 0858. I knocked, admitted by a doorkeeper well trained in the arts of houseman/butler, who said,

"Mark is finishing his prior interview, miss, please have a seat. You will be called in a few moments." The middle-aged man with military bearing left to attend to other business in the suite of rooms. I stood, bewildered, and waited as instructed.

The man who appeared was stunning to look at with gray hair the color of a thundercloud a double-breasted navy blue blazer gray slacks and black loafers. The off white Irish fisherman sweater under the jacket suited him far better than a collared shirt and necktie. His smile was brilliant. His blue eyes offset with the type of crow's feet seen on people who stare into the sun for long years. He gestured to the next room and I led the way with him following and closing the door behind us.

"Tell me, miss, why is it you wish to work for me and why is it I should hire you?" The man asked.

"Sir, I graduated university in May. I have not found work of any type in my field or even sufficient to pay my bills. My roommates resorted to working at Club Zanzibar. I tried waitress there for a week, but the pinching and groping was more than I could take and I left. There are some things that are not worth the money no matter how well the job pays." I told him.

"What did you wear when you worked at Club Zanzibar?" The man asked.

"The uniform was semi-sheer baby doll pajamas in wild animal patterns." I replied.

His look suggested he wished more detail, "If a customer paid for a dance set, you went up on a small stage with a stripper pole and took off your top during the first song. Your panties came off during the second song and you danced the third song naked."

"Being naked bothered you?" He asked with a tone I could not interpret.

"No, Sir. Only the groping and touching of the men trying to stuff dollar bills and fives and tens where money does not naturally belong bothered me." I replied firmly.

"So, when I tell you to strip naked right here and right now, what will you do?" His smile was a tossup between cruel and amused.

"I will assume that this is part of the 'and be able to prove it' that was in the ad, Sir. Do you wish me naked now?" I replied.

"Yes, and then we shall discuss the actual employment opportunity," he replied.

I removed my short winter jacket and placed it on a leather loveseat. My strawberry blond hair in the short pageboy cut looked natural enough, but I knew the man wanted proof that the carpet and drapes matched. I pulled off my cardigan. My freckled B cup breasts were bare beneath it, and unzipped the below the knee skirt letting it fall to the floor. Save for the calf high boots I wore I was now naked. My pubic hair is sparse enough I never bother to shave or shape it. It is also a lighter shade of red than my head of hair but it is natural.

"How tall are you?" The man asked. He then asked my weight and clothing sizes. I told him five feet nine inches, one hundred thirty-five pounds and a size ten depending on manufacturer and time of month. I tend to bloat a bit near my period.

"Do you tan or burn when in the sun?" I answered that with lightly tan but I need an SPF 45 or I'll blister.

"Put this on," he demanded and handed me a small plastic bag. A great many strings and three green triangle patches proved a thong style swimsuit. When I had it on, he smiled and told me to turn in a circle. His smile grew larger. He told me to retie the bottom over my hipbones and tighten it so that the triangle formed a camel toe. The light material, a silk I thought, wedged into my lips and began to rub erotically in my clitoris every time I moved or posed for him.

"The Chief and I are leaving to winter on Gull Cay, a small island I own in the American Virgin Islands. We require a staff of six to maintain the house, prepare meals and act as crew aboard the sailboat we shall use to get to the island.

"One of the points on your resume was your sailing skills. It is not often that a university grants a partial athletic scholarship for nine meter sailing.

"The other thing that impressed the Chief and me was your degree is in culinary arts and resort management. In this economy, it must be difficult to find work in the hospitality field. I can understand your not being in a five star kitchen or on the front end at a resort hotel. Many women resort to exotic entertainment when they find the bills overdue; I do not hold that against you. Their loss is my gain, should you accept my employment offer.

"Your employment will begin the first of February. If you decide to accept, your pay begins today. While in my employ, the MOST you shall ever wear is what you are wearing now.

"I see the look on your face. Yes, that means when you leave you will wear the bikini. The clothing you wore here UPS will deliver to your apartment in a day or two. The Chief will drive you home; I would not make you freeze on a subway and a bus to get back home.

"Should you accept employment you must understand that your pay is at the end of your employment contract? Once you accept employment, you will not be fired. You must complete the employment period to be paid. Should you choose to terminate employment before the end of the contract you will receive nothing. You will pay your own way home from Gull Cay or whatever point geographically you chose to leave.

"For the six month period beginning February 1st and ending July 31st you shall receive two hundred fifty thousand dollars." He finished talking and my head was awash with so many thoughts. He needed a woman who can sail, cook gourmet meals and look good doing it. I can sail, cook and he must think I look good. A quarter million dollars for six months in a bikini or less and doing what I loved to do anyway. This girl saw a no brainier looking straight at her. "I'd like the job, sir, if you are offering it to me."

I signed a contract and we shook hands. I left the suite by a different entry. The man referred to as Chief escorted me to a Bentley, sat me in the rear seat and drove out of the garage.

"Mark Chessman is not an easy man for whom to work, miss, I was stationed with him in the Navy for five years. You are the fifteenth woman to interview. You are only the second the Mark has hired. He probably told you his policy that you would not be fired. He did not tell you that you are subject to discipline. His toleration for first time mistakes is low. Repeat an error and his frustration level borders on wrath.

"The six women who make this trip will find something to occupy their time twenty-four hours a day for six straight months. Every penny promised you, you shall earn and every bit of you will be useful at one time or another.

"One last thing, miss, for the duration of your employment you shall be referred to as TWO. If the reference is to your work HELM or CHEF might replace TWO. Your name and those of the other women hired are not important to the Mark."

With that the Chief pulled the car to the curb in front of my apartment building. My purse, boots key fob and tiny bikini exited the car and headed to the lobby of my building. The thin covering over my breasts did little to nothing to hide my very erect nipples. Unsure if excitement, cold or fear had popped them out me brazened my way past the doorman and to the elevator. Only then did I feel the dampness between my legs. The small patch of fabric covering my mons was completely soaked through, touching myself to feel the dampness I orgasmic, with a visible shudder, while leaning against the car wall in the elevator. I came twice before I reached my floor.

I must have passed out upon the sofa and slept the rest of the day away dreaming of sails filled with warm tropical breezes and the clear blue of the island waters. When I woke my roommates were home, their reaction to my outfit and the stain on the bottom was direct and suggestive.

"Who was he?" Mary asked. "Does he have a brother?"

Sue wanted to know, "What the hell happened to your clothes, girlfriend? How did you go from fully dressed to a job interview in the city nearly naked to Teaneck, New Jersey, without being molested by every pervert on the D train or in the Port Authority bus station? Better yet, how come the cops didn't arrest you for wearing that outfit in public?"

.... There is more of this story ...

The source of this story is Storiesonline

For the rest of this story you need to be logged in: Log In or Register for a Free account

Story tagged with:
Consensual / Slavery / Exhibitionism / Workplace / Nudism /