Adventures Of A Part Time Sugar Baby free porn video

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?"

"Okay, I got the job. It lasts six months. It starts when I signed my contract, but I don't actually go to work until February 1st. One of the work conditions is that this is all I wear, well this or nothing, between now and July 31. I need both of you to help me keep to the dress code, no matter what. This guy seems like the type who will make sure I follow all of his rules." I gave as the encapsulated overview.

""So, stand up and turn around," Sue told me. I did and Mary whistled like a dockworker. Sue said, "You look tasty in that, girlfriend, I'd eat you like a gourmet cupcake as in don't wrap it up I'll eat it right here right now."

"Well, I for one don't like the idea of our roommate walking around in soiled garments. I think she needs to take that off and wash it, right now," Mary suggested, gesturing with her fingers.

I hated to agree with her. I had to though as my crotch was actually glued to the fabric of my bottom with the sticky secretions I emitted when I orgasmic. I began to walk to my room but was stopped by, "Where are you going? If your new boss told you it was the bikini or nothing, that means your robe, a towel wrap or any other covering is a no-no. So just peel that off and hand-wash it. When it dries we may let you put it back on." Sue ordered.

Here began the tests. My roommates began playing with dominant roles while knowing that my new job depended upon my submitting to a dominant boss. Little did I realize how the testing they put me through over the next week would prepare me for the first part of my journey into my new life.

The remainder of the day I was nude. Mary and Sue went into my bedroom and cleared my closet and dresser, locking my clothes into suitcases. They called down to the front desk to have a houseman come to put some things into the basement storage locker. "Get the door," Sue yelled to me, "After all it is your stuff that is going into storage."

I opened the door and it was Frank, the middle-aged handyman superintendent for the building. "Oh, sorry, miss, I'll come back later," he said in a flustered voice. He actually blush a deep red.

"No, that's okay Frank," I said nervously, "I had to pack all my clothes for storage I've taken a new job out of state and my wardrobe was totally wrong for it and my travel outfit is wet, I just washed it, so just come in and take those suitcases to the basement please."

Frank never let his eyes leave my body the entire time he was in the apartment. At the longest, it was three minutes, but it seemed like hours. I think he memorized the placement of every freckle on my body and knew how far my erect nipples stuck out from my breasts by the time he lugged the last bag into the corridor and placed it on the hand trolley.

I was exhausted and excited when he left. Mary began to applaud and Sue wolf whistled as they came from their rooms. "Great start, girlfriend. Damn you look horny as hell. Why don't you take care of that, or you'll mess up your one set of clothes again." Sue demanded. Mary placed a large towel on one of the kitchen chairs and added, "Go to it we want to see you come and come hard."

For the second time today, all it took was a few flicks of my index finger on my clitoris and I was spamming in orgasm. This time I had an audience. Sue knelt in front of me and began to lap up my juices. I offered no objection; though I did not consider myself bi or lesbian, I enjoyed the attention enough to have a second orgasm right on her tongue.

"Damn, girl, you are a tasty one," Sue grinned. "Mary, next time you need to take a taste of that girl honey."

We ordered Chinese for dinner. The girl who delivered our order was eighteen, a high school senior, and for some reason had piercings in her lip, tongue, and eyebrows, as well as from earlobe to top of both ears. Her shaggy pageboy haircut and ripped denim jacket and mini skirt completed the punk grunge image she tried to project. Of course, the girls had me answer the door still nude.

"Hi, Kim, come on in while I get you the money from my purse," Mary called from the kitchen. The girl entered our flat and her eyes were glued to me even tighter than Frank's were earlier.

Sue giggled, "See anything you like, Kim?" Kim smiled and nodded, not leaving her eyes off me. I was getting wet from the looks she gave me and from thinking of what the girls had planned.

"She is yours if you want her, Kim. She loves to be eaten and if you need relief I'm sure she will repay the favor." Sue had just pimp me out to an eighteen year old. I was embarrassed, I was excited and I was aroused.

The little Asian licked her lips and unbuttoned her denim jacket. A red bra was all she wore beneath it. The zipper of her short denim skirt was down and the skirt at her ankles seconds later. She stood in bra and matching red thong.

Unhooking her bra revealed pierced nipples. She stepped out of her thong and approached me wearing only her low cut Converse sneakers. Whether she shaved bare or had no pubic hair, her piercings in her labia and clitoris were obvious. My second encounter with a woman ended in a sixty-nine. Her tongue stud rubbed my nipples first and then as it dragged on my clitoris sent shivers through my body as I mimicked her actions on her body. Kim liked her piercings pulled. After several minutes working on her breasts, she yelped for me to move to her cunt and pull the rings hard with my teeth. When I did, she sprayed my face with her juices.

When we both recovered, she cooed in my ear, "Since I am all over you, your dinner is on me." She then thanked Sue and Mary for the very special treat and dressed quickly. Mary insisted on paying her. She grinned and thanked Mary while refusing a tip. Licking her lips, she told me, "Any time baby doll, and any time, just calls me."

Eating moo goo gai pan with the subtle taste of girl come in my mouth was a new experience. After we cleared up, I went to bed. I was exhausted. Little did I know what the girls had planned for the next week?

The call came in the afternoon of January 31 that I my picked up by the Chief was at a specific time the next morning. In a way, this was a relief, in the week leading up to my leaving them Mary and Sue had me run to the lobby nude for the mail and package delivery and up and down to the laundry room dressed the same way.

Mrs. Willkie the seventy-something who lived alone on the fourth floor, met me on the elevator on the morning of the 25th. She asked, "Young woman, do you realize you are nude?" She smiled when she said it and winked conspiratorially. She then said, "When I was in college in the 60s we streaked all the time around campus and town. Keep it up, dear, you bring back nice memories." Whoa, the thought of my grandmother running around naked suddenly planted itself in my brain. Mrs. Willkie and she were of a similar age group. Yipes, they were young and foolish once. Was I foolish to do this? Was the money worth it?

That afternoon the package from the Mark arrived. My clothes worn to the interview were in it, as were fifteen more of the silken green bikini sets. The Mark had a note inside, "My sources tell me you are following our dress code. You may wish to go to O'Malley's in Hackensack and buy three pair of Sperry Topsiders and two pair of canvas deck shoes. Pack everything but what you wear to the airport in the flight bag in this package and be ready for the Chief when he picks you up." Sure, enough, beneath my clothes was a soft leather flight bag with the number '2' embossed in the leather.

We three roommates went shoe shopping the next day, I was allowed to wear one of the bikini sets and we went at a time when kids were in school to avoid angry moms calling the cops. Though it was off-season, O'Malley had the Topsiders and deck shoes in stock. We were in and out of the store in less than twenty minutes. Jock O'Malley made me walks up and down the store in each pair of shoes, 'to assure they fit correctly'. I knew he just wanted to see my ass wiggle past him as many times as he could. I imagined Gwen O'Malley, his wife of thirty years, getting the benefit of the monster erection visible in his trousers, when he closed the shop for lunch.

The morning of January 31 dawned, or pre-dawned and I said good-bye to my roommates and waited for the Chief. He right on time; the next phase of my life had begun.

The 1st of February started without the sun. A gray overcast day promising rain. The day found me in hanger 27 of the Teterboro airport. The Chief arrived at the door of my apartment in Teaneck at, as he called it 'zero dark thirty'. It was a short drive to the airport where I waited, shivering in my green thong and boat shoes.

"TWO, so good of you to be prompt and properly attired," The Commander said from the hatch behind the cockpit of the Gulfstream. "It seems some of the others forgot the terms of employment began upon signing their contracts.

"Did you get the packages?" He asked.

"Yes, Sir, thank you. I was concerned that having only this one suit, it would wear out before the end of my contract." I replied.

He laughed, as the folding stairs to the aircraft came down, "TWO, if I desire you naked for six months I merely have to tell you to strip. Now, welcome aboard and find a seat in the cabin. We have a two hour flight to Port Canaveral to meet the boat."

I was the last girl to arrive. My guess was I lived the closest to the airfield and those that lived a distance were picked up before me. The Chief smiled and placed a velvet choker around my neck. A silver numeral '2' dangled from the green velvet. The Chief gestured to the large leather club seats; the eight of them arranged four to a side with what looked like a boardroom table between them, and told me to take an empty one and belt in for lift off.

Four nude girls with various shades of red hair sat in the seats on the far side of the table. A large pile of cast off clothing and shoes bore evidence of their error in judgment. One girl was wearing a yellow bikini the same style as mine. She wore the number '4' on her yellow choker and sat in the chair closest to the tail of the aircraft. I took the second chair in leaving the first seat for the Chief and one seat between Four and me.

No conversation and little eye contact came from the opposite side of the airplane. In my mind the nude women had instructions not to speak, possibly part of the 'you will not be fired, but you will be disciplined' clause. I looked to '4' and opened my mouth to speak. She quickly drew the fingers of her right hand across her throat and shook her head. I took the hint and remained silent.

The aircraft taxied to the runway and we became airborne moments later. When we reached cruising altitude the intercom came on, "TWO and FOUR please come up to the cockpit"

We two unbuckled our belts and knocked on the cockpit door. The Chief opened it from the inside and admitted us. He exited to the main cabin. The Commander flipped a switch reset a dial and took his hand off the yolk of the steering wheel. "We are on autopilot for the next hour and fifteen minutes. I wanted to speak to you both in private.

"As you both saw, our happy crew did not all step off on the correct foot. TWO, you were not here for the initial discipline. I regret that. Yet you were on time and in proper uniform. I have no complaint regarding you. FOUR, you were the third to arrive. Two women were already stripped. You were in your bikini and heels. While I agree the Nine West spikes make your legs look great, they are not the shoe of choice for a sailboat. For the footwear failure, you were silenced. You watched as the next two women arrived. One came in a three-piece business suit and the other in wool slacks and a parka. You saw each one stripped, silenced and awaiting punishment.

"Early failures will carry lesser penalties. As we get to know each other and work together, the punishments for gross errors will increase. Today, the Chief is informing you four compatriots their punishment is humiliation. You two and the Chief are to watch as the four others masturbate themselves to orgasm. The Chief will check each to assure none fakes the climax. You are to paddle the last woman to come with a ping-pong paddle. Each of you has twenty swats. If her ass is not bright red when you finish, the Chief has orders to redden yours. That is all girls; you have your orders, go carry them out." He dismissed us, and then added, "Would one of you brings me a cup of coffee, and I take it black no sugar, please?"

I brought the Commander the lidded mug I found in the galley of the aircraft. It bore the silver oak leaf of a USN naval commander. He smiled when he saw the mug, said, "Good Girl "2", and waived me away.

I returned to my seat. The Chief flipped a switch and the table disappeared into the floor. The four other women were now totally exposed to us three witnesses. "You may begin now," the Chief instructed.

I have my own technique I use to pleasure myself. Sometimes I am so excited, like the day I interviewed for this job, that a flick or two on my clitoris brings me off to mind shattering conclusion. My normal is a hot bubble bath and my cordless toothbrush. A low setting on my nipples, using the bristles, until they cannot take further stimulation and then the back, not the bristles, on the high setting directly on my nub. I am usually so weak I have difficulty drying off and making it to my bedroom.

The four women across from me were way out of their private pleasure zone. All were desperately using techniques from pinching their nipples to using fingers in the vagina trying for a quick but real come. Oddly, the more frantic they became, the wetter I became. I needed to bring myself off but I knew if I did, the Commander had not given me permission. I read enough master/slave dominant/submissive stories on the internet to realize the type of employment relationship of which I was now a part. The preparation of the previous week with my roommates around the apartment building had also helped my adjustment.

The girl on the far right of me, a slightly plump and shorter version of the red headed league, seemed to be making the most progress toward climax. Her right hand busily fingered her clit and her left pumped fingers in and out of her vagina. She rolled her eyes back and let out with a screeching noise from her mouth followed by loud farts from both her sex and her butt.

The Chief checked her by inserting a finger in her vagina and confirmed the contest had a winner. The remaining three redoubled their efforts to finish themselves. The medium red C cup tall and skinny as a fashion model and the thirty-something housewife Mrs. Average appeared neck and neck to reach their climax. The last girl, no more than nineteen and a small A cup athletic type actually looked bewildered, as if playing with herself was not part of her experience in life. Perhaps it was not, but I pegged her for the one FOUR and I would be paddling in a few minutes.

The Hausdorff took the silver medal. She came with both a gasp and a squirt of fluid from her vagina that left no doubt of the legitimacy of her orgasm. That left the model and the athlete hoping for the bronze. The younger girl savagely pinched her nipples and the sweat on her body glowed in the filtered light of the airplane cabin. Continuing to pinch her left nipple, the athletic teen used her right thumb and forefinger to twist her distended clit. Pain was her trigger and when she pulled on the hood of her clitoris, she came savagely.

No matter the model finished seconds later, the fact was she had lost. She was placed bent over the back of her chair, her face down toward the seat. She had tears in her eyes before FOUR and I began. Each of us had a paddle. We worked it out, me speaking FOUR nodding, she was still silenced, that my first ten strokes would be on the model's right butt cheek and FOUR would paddle the left. We would switch sides at stroke eleven.

The Chief told the model she was now allowed to speak, but only to count the strokes of her discipline and thank FOUR and me for our efforts.

Being right handed and taking the right side to start I chose to use a backhand swing. A screech and "One, thank you Miss" followed my WHAP. To the model's credit, she did not lose count in the first twenty strokes. FOUR and I changed sides giving the hot red butt of our target a few moments to cool down. I began again on the left cheek using my forehand. The model sobbed out the last ten stroke counts and wet her on number thirty-eight. Her pee running down the inside of her legs completed her humiliation.

"Discipline is complete. Silence is lifted. No names you shall all use your numbers, The Chief shall see you collared and dressed. We shall be landing in fifteen minutes. Be prepared to deplane when the aircraft stops at its hangar." The Commander called in over the intercom.

The short plump redhead who came first was "3" her bikini was blue as was her velvet choker. The Hausdorff was "1" her suit and collar were white; the model was "5" and was dressed in orange that almost matched her hair. The athlete who came in pain was "6" and wore black.

As the plane circled for landing, we all briefed our group as to the talent or talents that brought us together. "1" told the group she was a certified meteorologist and a former navigator in the USAF. I explained my sailing and culinary background. "3" related she earned a maritime engines mechanic rating and would take over the sailboat's auxiliary engines and generators. "4" held a merchant marine ticket as a deckhand. In past summers, she had worked on charter sailboats. "5" with the bruised and battered ass and the look of a fashion model was an accountant hired to handle the finances of the expedition. "6" smiled and told us, "I am Chief's daughter. He told me this summer was my entrance to adulthood. I screwed up in high school and did not get into college. It was this or I had to enlist in the Navy. Now I wish I had taken the other option." I shuddered. It was bad enough to perform for perfect strangers. She had to masturbate herself to orgasm in front of her father. She was the crews' backup. By the end of the six months, she was to be a competent sailor and able to make her way on any charter boat in the Caribbean.

We landed and a Town and Country van met us at the hangar. The driver saluted the Commander informally and when a Chevy Aveo pulled up, hopped into it and left. The Town and Country sat eight and with only flight bags in the rear area was plenty large enough for us. We seated by our numbers "5" and "6" sat in the rear seat and "3" and "4" sat in the front facing middle. "1" and I found ourselves seated in the rear facing captain's chairs across from "4" and "3". The Chief drove and the Commander sat in the front passenger seat. The airport was a thirty-minute drive from the marina in Port Canaveral where our sailboat docked.

She is magnificent. Twenty-seven meters from bowsprit to stern rail nine meters wide at the deck sloop rigged with at least a thirty-meter mast. The Bermuda rigging looked like it was supporting an old-fashioned radio transmission tower. Guy lines trailed down to cleats at the bow and stern as well as port and starboard. The spaced winching boxes for raising and lowering sail without climbing the rigging. Her bright work shined in the daylight. Her hull is painted Navy regulation haze gray and carved into her stern board is her name BLACK SHAMROCK.

We unloaded the van and waited for either the Commander or Chief to lead us aboard the boat. The Aveo pulled up and the driver who left it at the airport got our saluted the Commander again and he grinned and tossed her the van keys. We trooped up the gangplank then down a ship's ladder two decks and the Chief showed us our quarters. Three cabins with bunk beds a writing desk and a monitor. Each cabin was en suite with a head. It held a toilet a sink, a shower, and a long list of rules concerning fresh water, gray water and black water.