After a few months without embarrassing situations Jackie is inspired by a letter from her cousin Jenny.  Jackie asks Robert to make a special vacation for her.

Jackie's New-d Millennium

By TrackJim


The New-d Millennium -- Prologue

Jackie sat at her desk in her spacious corner office. Overall, the year had been good to her. Her professional career had blossomed from that of a computer analyst so that now she was a successful relationship manager liaison between the IT and the business community. The users were delighted as her good business sense stirred the company into the development of two profitable business international ventures. She should have been on top of the world, but she was not.

Except for that one event at the hospital upon her return from Las Vegas she had not suffered any embarrassing clothing incidents. She should have felt relief but she found she was strangely missing the thrill of those past accidents. "Am I a slut? Do I want to be humiliated?" Her thoughts swirled as her secretary dropped off her morning mail. She absent-mindedly worked her way through the mail until Jackie saw the postmark on a letter.

"A letter from Jenny?"

Jackie tore open the letter and became immersed in Jenny's most recent life events. Jenny's natural bubbly spirit brought a smile to Jackie's face. After relating how happy she was and asking when Jackie could come to visit, Jenny told of her most recent clothing mishaps. As Jenny told of some misunderstanding with some college fellows at a resort hotel, Jackie remembered Jenny's last letter and the tale of a fashion show that ended with Jenny exiting the runway minus a swimsuit she had been modeling. Jackie could not help but picture herself in both incidents and a warm glow filled her face. When she had finished the letter she turned to look out from her fourteenth story windows and spy across the metropolitan skyline.

For several minutes Jackie sat silently as her mind whirled in turmoil. A look of resolution grew on her face and she turned back to her desk. She placed a quick call to Robert in Las Vegas. He was delighted to talk to her and asked her when she could return. She asked him if he could get away for a while for the New Years weekend. She could hear the smile in his voice as she stated her proposition.

"Robert, remember, I want surprises. You make all the arrangements and call me back. Just tell me what to bring and where to meet you."

"Don't worry Jackie. Leave everything to me. And Jackie? Just bring the clothes on your back. I will provide everything else."


Robert had done a great job of keeping Jackie in the dark. The round airline tickets to Corpus Christi indicated she would be there for a week, but no other details were provided. When she deboarded the plane a black uniformed driver with mirrored sunglasses was waiting for her and escorted her to a black limo with very dark tinted windows. After she sat in the back the driver handed her an envelope before he closed the door. She opened the envelope and read it.




Jackie felt a warm flush run through her body. She knew Robert would not embarrass her (not too much) and a smile formed on her face. As she kicked off her shoes she noticed a second package -- this one slightly larger and on the floor to the right. She restrained her curiosity as she removed her blouse.

The air in the limo was just a little cool against her bare shoulders, midriff and back as she bent forward and reached under miniskirt. She hooked her the thumbs under the waistband of both her lace panties and her pantyhose and pulled them down together. Now in only her lacy bra and short skirt she sat back in the seat and stretched like a cat.

There was a knock on the window from the front seat and a moment later a center panel in the window slid open and the driver spoke.

"Miss, Mr. Robert said I was to make sure you had changed by this point of the journey. Please hand forward your remaining clothes with all due haste."

The New-d Millennium -- part 1

Well, this was what she had been missing the last few months. She handed forward the clothes she had already removed. With the front window still open she reached behind her back and unhooked the clasp of her bra. In one smooth motion she slid it down her arms and passed it forward.

The cool air felt coolest on her bare breasts and hardened her already nipples. A cool shiver started to work up her calves and her knees even as inner warmth flowed from her chest and down to pass below the waistband of her skirt -- her sole remaining garment.

"Hurry, Miss. We will be at our destination soon. I am sure you don't want to displease Mr. Robert."

There was just a tinge of menace in the driver's voice -- just enough to give Jackie to remove her last excuse of modesty. The back of the limo now felt warm as Jackie hooked her thumbs into the skirt's waistband and she lowered skirt. Her hands were shaking as she passed the skirt forward. The window slid shut and the driver drove on in silence.

For several minutes Jackie forced herself to ride and just stare out the side windows at lush subtropical scenery. Only then did she reach down and retrieve the package on the left floorboard.

The package was small and wrapped in plain brown paper that gave no clue to its contents. Jackie forced herself to go slow. She took her time as she unwrapped it. Once the paper was removed she found a white cube of pearl white plastic with the initials "W W" arranged as a stylized logo. She opened the lid of the box to discover small bits of material and some hard white disks.

The first bit of material was obviously meant to be some type of bikini bottom albeit an extremely immodest one. As she pulled it up her firm legs and settled the waistband about her slim waist she realized just how minimal this bikini bottom was. The part in front and passing between her hard thighs was not even an inch wide. In behind the material was little more than a string. Jackie did not think it even was enough as a string bikini. She knew the back would quickly slide and hide between her well formed buns, but it was the front that troubled her more for she could easily imagine the narrow strip of cloth also sliding between and within her most private feminine flesh.

"Well, at least there's a top!"

Jackie pulled the two pieces of hard material from the box only to find two small almost flat clamshells made of hard but not inflexible plastic. Attached to tiny holes in the plastic shells were the two strings. Jackie's face grew even redder as she realized the whole arrangement was meant to be a bikini that would show all her breasts save for barely concealed nipples.

It took several minutes to get the strings arranged. She was barely able to tie the knot in the middle of her back. She just knew the knot would slip loose eventually -- probably at some most inopportune moment.

"I wanted this, didn't", Jackie thought with some trepidation. She was committed. The driver had taken her small bag of toiletries. It had contained her only identification and the small amount of cash she had brought. All she had really had with her was the embarrassing bikini she wore.

Jackie sighed and sat back to enjoy the ride. The limo was following the Gulf Coast. The deep blue water had just a tinge of green with occasional whitecaps adding a beautiful contrast. She was somewhat surprised at how quickly relaxed.

"What am I turning into? Am I getting used to being naked?" she questioned herself. A few moments she got her answer.

"Miss, we are nearing your destination. It is time for you to open the second box. Please don its contents now."

Jackie grabbed the box and tore the paper from it. Upon opening the box she found a pair of strappy high-heeled sandals with towering five-inch heels. She immediately noticed the ankle straps did not have any buckles. Instead curved metal tongue-in-groove tongues were ready to slide into corresponding metal slots. Jackie had no doubt that once the tongue was inserted into the slot it would not soon be coming out.

"Maybe if I don't slide it all the way I can slide the strap down and over my heel." Tentatively she slipped on the right sandal and slid the tongue into the slot just far enough so it was still loose when she heard a soft click. Yes, the ankle strap would not part but there was still some slack in it. She slid the sandal down her foot and was able with some force to get the strap down over her heel. "Yes!" She could still get them off. She worked her right sandal back up her ankle. The straps across the top of her foot should be adequate to keep the sandal on her foot. She placed her left foot in the other sandal and slid the strap's tongue to the same first click.

Straightening her legs she admired the sandals. They were quite attractive and nicely accented her feet. She wiggled her dainty toes. "Once I restore a tan to my feet they'll look very sexy. If only the heels weren't so high."

A few minutes later the limo turned entered a small a harbor area. The limo stopped at the end of a long wooden dock. Several sailboats were moored to the sides of the dock and she saw people on most of the boats. The chauffeur exited the car and opened the door beside Jackie. The sun seemed brighter than earlier. Her eyes had gotten used to the darkened back seat. As her eyes adjusted the chauffeur spoke.

"Mr. Robert is on the boat at mooring number five." The chauffeur pointed down the long dock. Jackie realized she was expected to walk to the boat. As she stood and put weight on her sandals, she felt the ankles straps tighten. They stopped before pinching her ankles but she had no doubt they were much too tight to slide past her heels. Her sandals were on to stay for a while.

Jackie set out for down the dock. Her high-heels forced an involuntary sway into her pert ass. After only a few steps she felt the bottom slide snuggly between her firm rounded butt cheeks. The occasional wolf whistles and comments from men on several boats made her feel very much on display. Before she had made it to Robert's mooring the clamshells moved across her breasts and she felt of hot sun on her bare nipples. She tried to adjust the top twice as she continued walking, but it only took moments for the shells to once again creep off her nipples.

With all this going onto Jackie was relieved the narrow front of the bikini bottom was staying in place. Unfortunately that was not good enough. She felt moisture forming between her thighs as she tried to hurry along. The tall-heeled sandals made anything faster than a brisk walk impossible. Hurrying only intensified motion of her hips and the affect made her mind all to aware of her barely covered loins. By the time she had reached mooring five Jackie could not deny to herself how charged up she was. She saw Robert standing near the railing of the sailboat on mooring five.

"Captain Robert, permission to come aboard?" Jackie asked. She had heard that in some movie.

"Permission granted, Miss Jackie. Please step on board. We are about to cast off."

Jackie climbed the two steps to the railing and stepped over. Immediately three young men appeared with one taking the wheel. The man at the wheel ordered ""Cast off!"" and in instants the sailboat flowed unfettered. The sound of a small engine increased and the sailboat moved slowly away from the dock.

""What can I do to help?"" asked Jackie.

Robert smiled and answered. ""We need to hoist the ship's flag.""

"Where is it?""

Robert's smile almost ran ear to ear when he answered ""You are wearing it.""

Jackie hands flew to her chest as she went slack jawed.

The New-d Millennium -- part 2

Jackie was in shock. Did Robert really want her to surrender her skimpy last bit of clothing? Only moments before she had felt the mini bikini was so embarrassing, but now she was almost ready to fight to keep it.

"Gotcha", Robert chuckled. "You were looking far too comfortable." He continued to chuckle until Jackie's shocked expression changed to a smile. They were both laughing until Robert added, "You won't be getting off that easily."

Robert walked to the fore deck and stretched out on one of the two deck chairs. Jackie became aware of an appreciative stare from the man at the wheel. She moved forward to join Robert as the boat eased out of the harbor. She stretched out on the deck chair beside him and forced herself to relax. Within minutes the sails were hoisted and the engine silenced. Jackie watched as land disappeared over the horizon.

Robert spoke. "It's time to do some explaining. The young blond haired young man at the helm is Winston. This is his boat and I've chartered it for the full week. Willy and Paul comprise his able crew. On this boat I am the honored rebel leader, but you are only the kidnapped princess. We are holding you for ransom. At anytime you can be ordered to do almost anything. Failure to comply and you'll be punished at my discretion. The only restriction is only I can order you to have sex."

Jackie accepted this with a giggle. She wanted him to surprise her. "My first decree is that at not time will you be allowed to pleasure yourself. Since I know you are a hormone filled creature I'll help you comply. Place your arms squarely on the arms of the deck chair."

Jackie positioned as instructed. Within moments nylon line was wrapped around her wrists and elbows securing them to the arms of the chair. The ropes were not so tight as to be uncomfortable but she was obviously going to be in the deck chair for some time.

Robert looked over his rope work with satisfaction. "It looks like you need some sunscreen." He disappeared from her view only to return a few minutes later with a bottle of lotion. He started on her feet and worked his way up her body.

Jackie found herself being lulled into a warm sensual haze. Robert's hands felt so good on her legs. He had worked the rich lotion into her feet then her calves and was working on her thighs. His touch was almost electrical as it kneaded her flesh. A soft moan escaped her throat as she felt his hands reach her hips. He lifted her hips.

"Yes, he's going to take me right now", she thought. She felt her teeny bikini bottom slide down her legs. His lotion covered hands caressed her waist and stomach and moved higher, but they did not touch her hot sex. She opened her eyes to see only Robert. The boat's crew was out of sight while Robert's hands worked up her body. Upon reach her breasts he worked around the clamshell top and continued working the rich lotion into her flesh.

Jackie's looked up into Robert's eyes and asked, "Aren't you going to take me now?"

"Didn't I say you wouldn't be allowed to pleasure yourself? If you ask, then I'd only be your instrument of pleasuring. For that infraction I think you need to simmer a while."

Robert walked aft out of her field of vision. Jackie felt her arousal fuel her frustration. Here she sat - strapped to a deck chair and bottomless under a deep blue canopy of sky. The roll of the boat and sound of the waves were very sensual. Jackie eventually drifted into a light sleep and she dreamed.