My New Boss Pt. 28

Emboldened by his successful vacation with Ana, Suky, and Steph, Tim decided he wanted another honeymoon vacation with both of our girlfriends. Steph wasn't invited this time, having fallen out of our little group. However, Suky was game, and this time Tim wanted me to tag along and witness how much fun one guy could have with two women. Needless to say, I wasn't enthralled about the whole vacation scenario, but it got worse. This sordid love affair was going to be filmed and televised to an audience of millions.

Tim broke the news to me on FaceTime, shortly before they were set to leave. He was beside himself with joy as he told me that he had secured the four of us a trip on the Below Deck Mediterranean boat, a well known reality show.

"I am coming too?" I asked, seeking clarification.

"It is a mandatory work retreat," he informed me, in a very business-like tone. "There will be ten of us attending. You and Suky are invited as a couple."

Once I leaned that it was a work-related trip, I was very relieved. I was also excited to be on the latest season of Below Deck Mediterranean. I had watched every episode of the television show since its inception. I really enjoyed the dynamic between the guests, as they enjoyed the opulence of the ship, and the crew, as they struggled to provide exemplary levels of service and luxury. The contrast between the beautiful state rooms provided to the VIPs, and the below-deck, cramped, sleeping births that the crew occupied in the few hours per day that they were not toiling, was amazing to me. Two groups of people occupying the same multi-million dollar boat, but having two polar opposite experiences.

Tim, as global head of our company had decided to embark on a team-building exercise, and there were ten of us going from the company. There were three married couples, from the upper echelons of the company management, my boss Tim, his girlfriend Ana, and then Suky and I.

I read the brochure several times, mainly to establish that there were enough state rooms to accommodate five couples. To my relief, there were six double rooms on board, so I didn't have to worry about Tim enjoying the delights of Ana and Suky, and banishing me to the bathroom, when it was time to sleep.

About three weeks before our departure date, the producers called me to go over the travel arrangements. To my surprise, they had a Town Car scheduled to pick me up the following morning. When I suggested that the car was three weeks early, they dropped a bombshell. Apparently, this season they were experimenting with a new format, one in which one guest would spend three weeks below deck, prior to embarking on the luxury experience above deck. I had been selected as the guinea-pig for the experience, and was flying out to the boat tomorrow.

They told me to pack a very small bag, as the crew accommodations were extremely cramped, and I would be spending most of the time in my uniform. I was in such a rush to get packed and ready, that I never really had time to go over my new itinerary with Suky or Tim, my boss. The car picked me up the following day, and fourteen hours later I was in Greece, boarding the Below Deck Mediterranean boat.

Any illusion of luxury was shattered after my first sixteen hour shift. As the least experienced of all the crew members, I was assigned the lowest position on the boat, that of Junior Deckhand. They may just as well have called me 'gofer' as I did all of the crappy jobs that no one else wanted any part of. I cleaned toilets, emptied the trash, did all of the laundry, even cleaned up when anybody threw up.

After twenty-one days of suffering from the effects of physical exertion, muscle fatigue, sleep deprivation, and severe claustrophobia, from sleeping in a tiny room with two other crew members, I was summoned to the main deck, all spruced up in my 'dress whites', to welcome the rest of my party to the opulent luxury of the boat's upper deck.

Even though it was just a show for the cameras, it was emasculating to carry my boss' oversized suitcases up the gangway and into his state room, as he was greeted by the Captain and the senior crew members. Tim, entered the boat with Ana and Suky on his arm, as if they were both his fuck-toys.

I had seen Ana once before, in the back of the stretch limousine, although from my vantage point that day I was only able to ascertain that she was a petite Asian. I had also seen quite a few pictures of her, that Tim had posted on his social media accounts. However, in these days of selective lighting and filters, even the most average of young girls, can be made to look like an Instagram model.

That said, in real life, Ana was absolutely stunning. I had spent the last twenty-one days working and sleeping, and had not even had time to jerk off once. For this reason, I had to look away as she approached me. She was just too beautiful for words, and I felt my cock stiffen in my dress whites, as I imagined having sex with her.

She was having the same effect on the television production crew, judging by the lewd comments they were whispering among themselves. I could hear the cameramen and sound guys trying to figure out the relationship between Tim, Suky and Ana. There were even a couple of bets placed.

"Wouldn't be the first time some rich guy boarded with two smoking hot bitches," I heard one of the sound guys exclaim.

Their relationship got even more murky, when I was instructed to take the luggage belonging to all three of them, into the master suite. As I placed the last of the cases at the foot of the massive King Size poster bed, Tim spoke up.

"Thank you, young man," he addressed me, even though we were the same age. "We are going up to have a cocktail and watch the sunset. We would appreciate it if you could unpack our suitcases and put everything away. My white linen pants will need a press, too, before dinner."

There were cameras everywhere, and a microphone right above my head. I didn't want to mess up the production, so I stayed in character.

"My pleasure, sir," I responded, using the response I had been taught in my brief training session.

A broad smile crossed Suky's face as she watched my subservience to my boss. Then, as a kick in the nuts, Tim handed me a five dollar bill, as a tip. I had watched enough episodes of the show to know that the tip occurs at the end of the week long voyage. They even have a tip meeting among the crew to determine the amount of the tip, and each person's share. This five dollar gratuity was done to diminish me in the eyes of my girlfriend, and probably made for great tv viewing, once the show finally aired.

"Thank you, sir," I responded, knowing full well that any other response would be met with a resounding, "Cut!" from the filming Director.

Tim didn't acknowledge me further, but placed his hands on Suky and Ana's butts, and escorted them both from the room. The camera men and sound guys left the room behind the happy threesome. Apparently, watching me unpack my boss' suitcase and hang my girlfriend's lingerie in his closet next to his suits, would not make good tv viewing. As it turned out, Tim had packed fairly lightly and I had his clothes put away in just a few minutes. I hung his white linen pants on the doorknob to remind myself that they needed ironing.

Ana's suitcase was next and I had to handle this with extreme caution. I had the hots for that young Thai girl, and my lack of discipline could land me in hot water. As soon as I opened her suitcase, I felt my resolve weaken. I had been on this boat for three weeks, and the long working hours and total lack of privacy, had prevented me from jerking off. I was horny as hell when I opened up her suitcase and was presented with the visual of all of her sexy clothes.

My cock involuntarily stiffened in my tight white dress pants as I began to remove her clothing and hang it up. Short skirts, tight dresses, silky camisoles, high-heels, bikinis and way more many pairs of panties than one girl would need for seven days on a boat.

I was leaking in my underwear by the time I got all of her clothes put away. She didn't seem to own any pants, shorts or low-heeled shoes, or at least elected not to pack them, instead allocating the majority of the space in her suitcase to lingerie and bathing suits. In a weak moment, I took advantage of the absence of any camera crew, and stole a pair of her panties. Bright yellow in color, with strings that tied at the side, they were constructed of the tiniest piece of material, and fit easily into the pocket of my dress whites.

I unpacked my girlfriend's suitcase last, and shuddered at the discovery of my cock-cage, my pocket pussy and her black strap-on, that was actually a prostate stimulator. Why on earth had Suky felt the necessity to pack that shit?

Once I had put all of their stuff away, and stowed their suitcases, I took Tim's pants to the laundry area, and then went to find a senior member of the crew. It was the Bosun that I found first. He was very unsympathetic to my concern that I should be joining my party in the opulent surroundings of the accommodations, above deck. Apparently, he had two crew members that were injured in a tender accident, and was already short staffed. Seeing that my pleas were falling on deaf ears, I went and found the Chief Stewardess, who ran the interior of the ship.

She was equally unconcerned with my plight, as she was also two crew members short, having had two of her stewardesses leave the ship with the flu, as required by company policy. She was more interested in solving her problem than in remedying mine, and marched me straight up to the Captain. The Captain explained that the ship couldn't leave port without a minimum number of crew, and if I rejoined my party, which was my right, we would have to spend the week tied up to the dock.

I was tired from the sleep deprivation, weary from working sixteen hour days and in no mood for a fight. I knew my boss, Tim, would order me below deck if the alternative was for us to sit next to the dock all week, so I acquiesced, and agreed to remain as a crew member, for the time being.

"Is he working for the Bosun, or as a Stewardess?" the Captain asked the Chief Stew.

"He will be a Stewardess," she replied, "unless my replacement Stew arrives before the new Bosun's mate."

"Get him in the right uniform then, Maria," the Captain growled, as he dismissed us with the wave of his hand.

The Chief Stewardess muscled me out of the Captain's wheelhouse, and led me down to the laundry area, which also housed the spare uniforms.

"What size are you?" Maria asked.

"I normally wear a medium," I responded, worried about where this was headed.

"Women's size?" she responded, clearly irritated that she had to dress me.

I shook my head in confusion, and repeated, "Women's size?" under my breath.

"You look like you are an eight, but the male guests like us to wear form-fitting clothes, so let's get you into a six," she said cheerfully.

My heart sank at this revelation. The male guests were my co-workers and my boss, they didn't care what I was wearing.

"Can't I wear chinos and a polo shirt, Maria?" I enquired.

"Honey," Maria said dismissively, "all the girls need to dress the same. I need to know which members of the crew are mine, the guests need to know which crew members to approach depending on their needs, and the Captain, that horny old bastard, likes us Stews to show some skin. So get your ass squeezed into your size-six skirt, and let's get to work."

I was so embarrassed as Maria handed me the basics of my uniform. It consisted of a black stretch cotton polo-shirt, with the name "Samantha" embroidered above my left breast.

"Samantha had to leave the boat with the flu," Maria said helpfully, "you can go by Sam."

I reluctantly put the shirt on, it was very tight on me but was comfortable, constructed as it was of breathable stretch cotton. It was also very heavily scented with Samantha's perfume. It was a beautiful fragrance, but the young girl had apparently spilt the bottle on herself, when she was preparing herself for her work shift. Once I had arranged the tight-fighting, overly-scented shirt, just so, Maria handed me a beige stretch cotton skirt, with a matching belt, a pair of light beige, thong panties, and some skin-tone thigh-highs.

"You are kidding me right?" I asked. "I can't wear these," I exclaimed.

"Samantha," the Chief Stew began, instinctively looking at my name tag as she was used to a revolving door with crew members.

"Sam," she corrected herself, "the Captain and your boss had a meeting earlier today to discuss the options with regard to your week-long boat trip. They both agreed that it would be better for all, if you take one for the team and work as a Junior Stewardess this week. That way we can at least have the minimum number of crew on board to be able to leave the dock."

"Yes, but a skirt and stockings," I cried, "is that really necessary?"

"Absolutely," Maria responded, shutting down my protestations. "The crew need to present a unified front by being dressed identically. The Captain and the guests need to be able to distinguish the outside crew members from the inside crew members, from a distance. Besides, I offered Tim, your boss, the option of beige shorts for you and he responded unequivocally that he wanted you to 'blend in and be like the rest of the girls'. Now get dressed, we are serving cocktails by the jacuzzi in ten minutes."

With that last directive, Maria was gone. I took one last nauseating look at that skirt, and reluctantly squeezed into it. Luckily, it was made of stretch material, as it was definitely too small for me. It was very short too, as I am probably taller than the average woman. I tried the thong panties on, but they were very uncomfortable to wear, let alone work in. Not only did the thong ride right up between my ass-cheeks, because they were several sizes too small for me, but it did little to cover my stiffening cock. In fact, all the thong underwear did do, was to apply pressure to my cock-head as it sought to escape the confines of the tiny silky undies. This served to squeeze pre-cum from the tip of my cock, which would not be a good look in the light beige stretch skirt.

I discarded the thong panties, and picked up the skin-tone thigh-highs. They felt very soft as I slid them up my slender legs, but when I pulled them up as far as they would go, it became obvious that they were several inches too short. Apparently, I was a few inches taller than Samantha was. Undeterred, I had a quick look through the laundry room drawer, that Maria had pulled the thong and thigh-highs from. There were several pairs of underwear in there, most of which were even smaller than the pair Maria had selected for me to wear.

After a couple of moments rooting through the underwear drawer, I emerged with a garter-belt. It was hot pink, made of silk, and adorned with feminine bows across the front and on each garter strap. It was clearly not regulation work-issue, but it would solve my current problem, so I hastened to put it on. I made sure it was perfectly straight, clipped the four garter straps to my thigh-highs, and tucked my erect cock under the waistband of the garter-belt, to hide it.

I was thankful that the interior crew were required to go barefoot, as I really didn't want the added humiliation of high heels. I tucked my shirt into the waistband of the skirt, fastened my belt, and went upstairs to see how I could be of service.

My appearance, dressed as I was as a Junior Stewardess, created quite a stir upon my entrance. Tim, let out an appreciative wolf whistle, and beckoned me over to him. I stood in front of my boss, trying to blot out the faces of my co-workers as they all took me in.

"Fetch us a round of Tequila shots, Samantha," he said derisively, playing up for the cameras, as he rested his hand on my lower back, right above my ass.

"My pleasure, Sir," I replied as I turned and fled the table, before he lowered his hand and copped a feel, or even worse, discovered I was wearing a garter-belt!

My hands were shaking as I fixed the drinks for my co-workers. One of the other Stews offered to carry the tray of drinks out for me.

"Until you get your sea-legs honey," she said kindly, mistaking my terror at having to serve my co-workers dressed as a girl, for some kind of symptoms of sea-sickness.

Tim and my fellow workmates ended up having five or six rounds of shots, and things were quickly escalating, as they got wasted. Once they realized the dynamic between myself and the paid guests, the other Stews protected me the best they could, but as the evening wore on Tim got way more touchy-feely. He was basically groping me whenever I approached his side of the table, and finally he grabbed hold of me and pulled me onto his lap.

"Come here Samantha, you little prick tease," he said, slurring his words.

I felt his erection against the back of my skirt, as soon as my ass hit his lap. It throbbed and jumped around in his pants, as he forcibly held me in place. The other guests, sensing his arousal, and being subordinate to him in the company, all excused themselves for the evening, feigning tiredness from the journey to the boat. Within two or three minutes I was alone with Tim, Suky and Ana. The two girls sat without expression as I writhed on Tim's lap, trying to escape.

All that squirming around on my boss' lap, did nothing to extricate me from his iron grip. He was just way too strong for me, and I eventually tired and gave up. The protracted struggle, and the resultant wriggling around on Tim's lap, had increased his arousal though, as evidenced by his erection which was now tenting in his pants.

"Somebody wants to get balls-deep," Suky teased.

I flashed her a dirty look. I would have expected a little more support from my girlfriend, as my boss was trying to butt-fuck me at the dinner table, but Suky had her priorities correctly aligned, and was focused on my boss' needs and desires, rather than the preservation of my anal passage. She got up from her seat, and turned the lights off, so that Tim and I were left in the romantic light of a pair of candles, burning on the dining table.

As I sat passively on my boss' lap, he kissed the back of my neck, and whispered softly in my ear.

"You smell good, baby. What perfume are you wearing?"

I cursed myself for being dumb enough to wear that overly-scented shirt. I should have asked Maria for a freshly laundered one. I didn't answer my boss, but pulled away from his lips, which were now nibbling my earlobe.

"Don't fight me anymore, Samantha, this is happening, with or without your consent," my boss said assertively.

I looked over my shoulder at him, to gauge if he was being serious or just fucking with me. Even though his eyes were glazed from his excessive alcohol consumption, there was a steely resolve in them. My boss was planning to fuck my ass, and there was very little I could do to stop him.

"Maria?" I cried out, looking for the Chief Stewardess to save her most Junior employee.

"All the staff have turned in for the night," Suky said with a smile, "well except you, Samantha. Maria left you to take care of our needs tonight. You smell divine," she added, as if to reinforce that I had way too much perfume on.

Tim was molesting me now, his hands roaming all over me as I struggled to maintain my composure.

"Please, Tim," I begged, "let me get back to work."

"This will be your sole form of employment, if you don't get with the program," Suky chimed in ominously, reminding me that this man held my professional life in his hands. "Have fun tonight, baby," she said, before she left me to the wolves.

I can't really remember the exact moment when I decided to stop fighting his advances, but to this day, I justify it by my possible loss of employment. Tim Andrews was the Global Head of my company, and I had an irreplaceable job, that I loved, and that paid me sixty thousand dollars per month. I repeated that figure over and over in my head, as I lowered my defenses, and allowed my boss to take liberties with me.