Salesman Enjoys Trip Of His Life

Introduction

I have not had this story edited so if you find some major spelling errors or other issues, please let me know.

February

One of the perks of working in sales and being successful with it is the annual trips your company pays for. I was lucky enough to have a Hawaii trip paid for and since the trip always allows the winner to bring a significant other along, my girlfriend and I took advantage of an all-inclusive vacation last year; correction, my ex-girlfriend and I.

The trip was definitely the peak of our two year relationship before it fell down face first a few months later. We couldn't find a reason not to argue about anything - from who should pay for the dent in her car, to what sex fantasies were off limits.

Don't get me wrong, Sara was good looking and barely held back in bed but the more the tensions grew it felt like more and more things became 'unconformable' for her which was a joke compared to all the wild things we did in the first three quarters of our relationship and especially in Maui.

While I had a slow start with this year's campaign, I gained some steam with consecutive months of near record breaking sales. I could start to taste the salty air while sunbathing on the cruise next to a babe, but my mind simply didn't allow me to go into too much detail since I had no idea who I would take with me.

April

Fast forward a few months and I find myself leading the campaign. For some reason selling IT consultation contracts to decision makers that don't know the difference between the internet and their intranet wasn't the hardest gig. As we came down to the last few months of the campaign, my coworker and friend David started catching up with me after closing a $1.2M deal in the middle of the month. His fiancé promised him an unforgettable sex escape if he won and knowing how little inhibitions she had (based on David's stories and experiencing it first hand at the company's holiday party) I knew David had every intention of taking the prize home.

Previous December

Speaking of the holiday party, it was a bit awkward being the only person out of 35 employees of the sales department that came solo. But the advantage was being able to flirt with the handful of female co-workers or their female companion since they weren't in a relationship either. Aside from David's fiancé, there were only a couple of other girls worth looking at but that was more than I could have asked for.

It being a formal event at an upscale steakhouse the men wore suits while most women wore cocktail dresses with teasing pairs of high heels that brought them closer to my 6'4" frame. Especially David's fiancé (without heels was approaching 5'8") who was so hot in her little black dress showing off her C-cup cleavage, perfectly tanned legs, and little ass that most men including the married CEO of the company couldn't keep their eyes off her. She knew it too and it was clear that she was pushing the envelope when she bent over, crossed her legs or leaned forward just at the right times.

Unfortunately, David was oblivious to the fact that Meghan was teasing the men around him. She was not only a sexy vixen but also in great shape and probably kept in shape while working as a physical therapist. I always wondered how hard it must be to have her as your therapist since she runs her own practice near downtown Seattle and from what David had mentioned always wears the tightest fitting leggings and athletic shirts. If she was to show me any stretches while wearing some of those outfits, I am sure any pain would quickly disappear.

Both she and David had had a few drinks with David becoming the life of the party telling stories that only drunk people would find funny. Meghan, while still able to walk in a somewhat straight line in her sexy black heels, was definitely becoming even less conservative in her actions.

While I enjoyed the view of her (she was now the only hot girl left at the party) I knew she was off limits. If you took David out of the picture I would have found a way to have her suck my cock or take her from behind in the parking garage. I just remembered that my Audi A6 was conveniently parked in the far back corner so it shouldn't be too hard to stay out of sight. My mind got quickly carried away with the visual of me banging this tall slender brunette from behind and I started to realize that my excitement was showing in my pants.

I decided I had to take a leak and with half the party guests being gone I thought I should actually get ready to head home. When I came out of the bathroom ready to say my goodbyes, there she was standing with her back against the wine rack, with her left leg lifted so her heel was resting against the wall. The black mini-dress was hiked up to the point where if one was to try hard enough, he should be able to make out the color and material of her underwear. Since the area was poorly lit, however, she was able to not draw more attention from others in the main area of the restaurant. There was no doubt about her intentions as she was licking her lips and rubbing her hand up and down her thigh. In that moment of male weakness I approached her and asked if she needed anything.

In response she lifted her leg even further and started rubbing my crotch with her naked knee which caused an immediate hard-on. 'Forget the parking garage,' I thought. In the few minutes I was in the restroom, no one else was in it and the handicap stall was large enough for any sexual desires I had at that point.

The moment of her knee rubbing my member to full attention seemed to have lasted an eternity and I think I even had my eyes closed. "So, do you want to help me?" Meghan asked in the most suggestive way possible which for some reason brought me back to reality.

David and his continuous talks about the upcoming wedding that summer came to mind and I broke it off there and then. To say that she was disappointed was an understatement. She ran off in anger and told David who was in the middle of another story that it was time to go. So that was the abrupt ending of an otherwise exciting evening.

April/May

Here we were with only 6 weeks left in the campaign and David finishing prep work for another huge presentation to a Fortune 500 company. I knew that I was probably going to have to settle for 2nd place prize consisting of a $1000 gift card. The 2nd prize was definitely an insult because what either David or I would have made for the company in 2nd place is in the high 6 figure range in profits if not more. Granted, the commissions are very generous, but if I was the decision maker, I would offer the cruise which was supposedly valued at $15,000 and leave anyone else in the dust instead of making the runner up accept that gift card in a meeting. In the past, the first place winner could opt out to take some cash value if you didn't want to go on the trip but this year's cruise had to be paid for far in advance without an option for a refund.

Days later I closed a fairly good deal, improving my chance to hold onto first place with no idea who to take if I was to win. There was Jennifer who was a recent intern converted to full-time support staff. She made it through 4 sorority years and was the Barbie type blonde who always made sure she looked perfect before leaving the house in the morning (which always made we wonder what she was trying to hide underneath of all the makeup). She made every man's head turn most of the days when she either showed up in a pencil skirt, black leggings, or tight dress pants that showed off everything her young 5'4" body had to offer. We actually had lunch together a couple of times but I wasn't able to get a read on her and I couldn't find the courage to ask her out on a real date. I have never had a problem asking girls out, but with my breakup still leaving a mark on my heart, I was slow to get back into the dating world.

Jennifer was sitting across from my office and with today being her high heels and pencil skirt day, I kept looking through my office window to get a glimpse of her legs and feet that were poking through the bottom of her desk. Just as I imagined my hands running over her body, David stormed into my office with a look on his face that I will never forget. I could tell he had been crying and his face was so pale that he either had his life blood sucked out of him or he was about to vomit all over my desk.

"She is such a slut," were the first words coming out of his mouth.

"Meghan?" I quickly concluded.

"Yes, I thought I'd pay her a visit and drop off some coffee for her at her office and it was closed even though her car was there so I went to the back and saw her getting fucked by what must have been a patient of hers."

I would lie if my mind didn't try to picture the situation of his fiancé in some downward dog position getting pounded from behind but I quickly became the supportive friend that he needed me to be.

Despite both of us working on closing some smaller deals, we decided to get his mind off of things and hit a few golf balls at a nearby range. It didn't dawn to me until later in the day that he didn't even confront her but simply stormed off. Being the good friend I was, I called up Meghan without letting David know and since she had my number stored in her phone, she answered with a flirtatious "Hi Don". Shortly after the holiday party she 'forgave' me and was back to being the big flirt she was.

I told her what David saw that morning and that he would like her to get her stuff out of his condo by the weekend. He would spend the next couple of nights at my place giving her the chance to pack up without them having to face each other. What really blew me away was that Meghan seemed to have cared less and I was sure that fucking that patient was not the first time she cheated on David.

The moving out went relatively smoothly and David's mood improved after a few weeks when he ended up closing the deal of his lifetime. The cruise was pretty much his and the $25,000 in commission that came along with the sale as well. As he was thinking about the cruise he was in the same boat as me all of the sudden. I suggested Jennifer who I knew he was physically attracted to, but having just come out of an engagement he was not yet ready to ask anyone out again either.

It was Happy Hour on Friday night so a couple of us co-workers got together for some beers and appetizers. There were seven of us including Jennifer whose casual Friday outfit consisted of a tight fitting sweater, black leggings and a pair of black army boots; she was simply a knockout that night. For some reason I started to feel the urge to become a matchmaker and asked her if she wanted to go on the cruise with David. But the more I thought about it, sharing a suite on a ship isn't a simple arrangement for two coworkers. I kept bringing the trip up but Jennifer didn't open any doors of possibilities for self-inviting her.

"Whoever wins should bring the other guy along," suggested Jennifer all of the sudden.

"This isn't THAT kind of cruise," was my immediate response.

"Don't be so immature about it. Think for a minute. You guys will get to relax, have all the food and drinks paid for one full week and the ship will probably be filled with a bunch of hotties."

It was a bit weird hearing Jennifer say that but after David and I glanced at each other, we gave each other the nod as if confirming we had a deal.

A couple of weeks later

Well, I hate to admit that David ended up winning the grand prize. The advantage of me being the guest and not the winner was that he would have to pay for the taxes on the winnings. I offered my gift card to spend on any other unexpected expenses that would come up.

As we made arrangements for the trip later that spring we actually got excited about the idea that we could be the hosts of numerous parties since we will stay in the presidential suite that even for cruise room sizes was a formidable 1000 square feet, not including the balcony. Jennifer kept reminding us that a lot of college girls like to let loose and that some bachelorette parties take place on cruises too. Too bad Jennifer couldn't be part of one of them...

June

Our flight was scheduled to leave at 8 am and we made arrangements to be picked up at my downtown condo. David spent the night at my place and the company arranged a car to pick us up at 5:30 am. We both pushed the snooze button on our phones too many times and got out of bed around 5:15 probably only woken up by the sunrise that was hitting my top floor pad. We both showered quickly but had no time to make any coffee or grab a bite to eat. The doorbell rang right at 5:30 and we still weren't close to being ready.

"Good morning, I am Steve your chauffeur," said our driver through the intercom.

"We are running a bit late, we will be down in a few minutes," I responded stressed.

"Let me come upstairs and grab whatever luggage is ready to save time," he responded.

I buzzed him in but was confused that the taxi driver was also acting as the bell boy. Previously, I had to drag myself and my luggage to the curb to be taken to a business trip and for the trip to Hawaii I had to make my own arrangements to the airport.

When we finally headed downstairs, we woke up slowly and were getting a bit excited. We had no paperwork on us aside from our passports as someone was going to meet us at the airport to explain our travel arrangements. We weren't sure why it was so secretive but we were joking by how the "flight concierge" might be some hot woman who will make sure our trip starts out right.

When we stepped out of the building we were greeted by a stretch limo.

"Ha, that's what I call an airport shuttle," said David jokingly.

As we stepped inside, we were greeted by the smell of our favorite Starbucks beverages.

"Your boss told us what your drinks of choice are. Hopefully we got it right," said Steve.

"This is perfect," I said as I sipped on a soy mocha.

As we pulled up to the curb at SeaTac I noticed a few glances from people around us who probably thought we were showing off. I must admit that driving 2 people in a vehicle that is meant for 12 was overkill.

Our concierge turned out to be a guy in his fifties but we weren't disappointed for long. He handed us first class tickets and he informed us that we can get a quick massage by the gate.

Hoping for two potential babes to lay their hands on us, we were disappointed again to be met by two young guys at the massage station. The upside was that their hands were strong enough to partially get rid of the stress and tension we had built up with all of our hard work.

We were the first ones to board and I felt like a king sitting in the oversized seats because I have never flown first class before. We were greeted by the first class flight attendant and we finally got our first look of a hot babe that day. Sandy was the type of girl who would be featured on an adult costume website as a model wearing a stewardess outfit. She was so flirtatious with both of us that I wondered if she was crossing the line of professionalism a few times. But then again, this might be the job responsibilities in first class.

Our first flight from Seattle to Atlanta was eventless and we actually slept through most of it. After landing, we were going to grab a bit to eat before our next flight to Puerto Rico when David checked his voicemail. As I was watching him, his face turned to that same pale white that I saw that morning a few months ago when we came to my office. He just stood there frozen.

"What's going on?"

"My mom, she had a stroke and is in the ICU."

"She lives in Orlando, right?" I asked.

"Yes."

"Well, let's go. We can get a rental car and head right over," was my honest, heartfelt suggestion.

"You don't have to come along. You deserve this trip and maybe I will be able to join you in a few days."

"Are you sure? I want to be there to support you in any way possible," I countered.

"It will be fine. My sister called me and she said that our younger sister is on her way from Chicago and my dad and her have been at the hospital. I will have a ton of family there. Go have yourself a good time and who knows, if it isn't too bad, I think the cruise line actually allows passengers to come on board at different ports."

I genuinely tried to convince him otherwise while he was trying to get a hold of a family member but with much hesitation, I agreed and was getting ready to head to my gate to grab a bite to eat and let him go on his way. Before I left, David opened his carry on and pulled out a black Canon bag.

"I bought this $5000 kit to take pictures of the trip and the ladies that we run into. Don't let that money go to waste," he tried to say cheerfully but was noticeably freaked out and was juggling his phone as he was trying to dial one of his family member's phone numbers.

I tried to calm him down a little but he was simply a mess. All I could do was just give him a quick hug and let him go on his way. I texted him a couple more times to make sure he didn't want to have me come with him but he kept reassuring me that he would be fine.

After all that I needed a drink or two so instead of getting fast food I decided to go to a bar and grab a burger and a few beers to go along with it. I wasn't sure if I should be mad, sad or excited. I was definitely mad about the fact that David couldn't catch a break and sad to hear the news about his mom, but I started to get thrilled to finally get a chance to relax. Just as I was downing my 2nd beer, I noticed these two girls entering the bar with their carry-ons.

Where Jennifer might have that Barbie doll beauty, these two girls were that Victoria's Secret model type but with some sort of natural beauty that would make any man's adrenalin soar. One of them wore a tight fitting Seattle shirt along with a jean miniskirt while her brunette companion wore a summer dress. Both of them actually made eye contact with me and I am sure they caught me staring at both of them from head to toe. There wasn't a part of their body that could be improved I thought. The blonde had her hair tied in a lose bun which went past her shoulder blades. Her t-shirt was made to accentuate what must have been D-Cup breasts. Her mini skirt, while not too short, revealed enough of her long legs to show them off. The brunette might not have had the same fill on top, but the rest of her body made up for it with even sexier legs.

They sat down a few tables away from me and I am proud to admit that I was able to keep my eyes off them for the most part when an announcement was made that my flight was about to start boarding. I paid my tab and got up grabbing the Canon bag and my carry-on when the two girls stood up as well.

"Also heading to Puerto Rico?" I asked nonchalant.

"Yes sir," they responded in unison with a smile that nearly made me melt.

The flight to Puerto Rico was another first-class treat. Having boarded first, I got a chance to watch most other passengers walk by as they entered the plane including the hot pair I saw at the bar. When they saw me sit in first class they gave me the kind of 'must be nice' look that I usually give others before I take my tall frame to the sardine can part of the plane.

I swear the airlines assign the hottest flight attendant to 'serve' the first class passengers. And as if the flight attendant was able to earn bigger tips by flirting with me, she kept on winking and smiling at me as she brought a few different drinks to me throughout the flight. I simply had a thing for women in uniform and even though her short heels didn't help much to lengthen her rather short frame she looked hot in her black pantyhose, the skirt that went to her knees and the blue and white shirt that covered her petite body.