This being my first story I guess I should start by describing myself. My name is Andy, I'm in my mid 30's and I'm 6'1" and 185 pounds with short light brown hair and crystal blue eyes. About 6 months ago I got out of a long term relationship and was just starting to get back out in the dating scene without much real success.
I've worked for the same company for the last 10 years, starting out in the field and working my way up into the office. I work for a small specialty construction company with about 30 employees, 20 field managers and 10 office staff. The owners are husband and wife team. Rob is in his mid 50's and is a started out as a great boss but over the last few years has taken less and less interest. She is the same age as I am and is a very intelligent but short tempered red head. For the last few years after a couple of drinks around the bar my boss would all ways say that if we had a great year we would have an office getaway. Of course all the office staff would say tropical and all the field staff would say hunting but it would never happen. It became something of a joke between a few co-workers and I. we would bet on how many beers in before the boss would bring it up and then how many more beers until his wife start yelling at him to shut up or book the damn trip.
Imagine my surprise when a mass email from the boss showed up in my inbox saying there was a sign-up sheet on the front desk and I was to put my name under either, four days and three nights in Canada or Mexico. Freeze my ass off in a tree stand waiting on some animal to walk by or siting on the beach working on my tan waiting on some bikini to walk by. Not being a fan of cold weather to begin with and being freshly single you can understand that my name was the first under Mexico. Unsurprisingly, almost the entire field staff fell under Canada and the entire office staff went in for Mexico.
As time drew nearer we all realized that the boss's ADHD had kicked in and he had booked the hotels for both trips but hadn't booked any of the flights. The head of the field staff, Mike (and my direct counterpart) took it upon himself to quickly book all the flights. Unfortunately we couldn't all get the same flight since they had waited until the last minute. So six people would be on a flight in the morning and the remaining five would catch an afternoon flight. Mike, being a strange duck, thought it would be "funny" to book me with the five women on the early flight. I'm sure he saw this as a chance to sleep in and hopefully get a leg up on me with the boss during the later flight. I on the other hand could care less. A free vacation is after all a free vacation.
That is how I found myself loading way too many overloaded lady suit cases into the back of my suburban at 5:00am as some light snow flurries fell down my shirt. All I could think about was getting to the airport and on the plane before the snow really started to come down. All the weather guys on all the T.V. stations agreed that the snow would stay north of us and we would only catch the very southern edge of the wintery storm. When that many meteorologists agree, I start getting nervous.
I guess this would be a good time to describe my group "the A team" as we started to call ourselves. First on the list is the new girl, Jodi. She is in her early 20's with short white blond hair, brown eyes, and lips made for sucking dicks if you know what I mean. She is very short just under 5 feet and a bit on the heavy side. She is what I would call, pretty but plump. Always tan no matter what time of year. Apparently, she really liked to party it up in college and she comes across as a bit of wild child. She was recently hired as an office assistant for the Boss in an attempt to keep him on track, but it seems she is only making it worse. From the way he stares at her round ass it would appear that he likes the thicker girls. She is also recently engaged as her college boy toy proposed just before the holidays.
Next on the list is Ann the office secretary. In her early 50's she started working for us a few years ago when her two children went off to college. She is also on the shorter end, maybe 5 feet tall, maybe 100 pounds, with medium length curly black hair. She is very fit with a body most women her age would kill for. It's difficult to tell but she appears to have a nice c cup rack hidden under all ways tasteful but boring clothing. Mousy isn't the right word for her but she is very quiet and when she talks to you it's to the point with no extra fluff. She never rocks the boat and all ways does what's asked of her.
Next up is our part time foreigner Aznar. Born in Iran, she came to the US for college and got a master in science as well as a well-paid lawyer/ husband while here. After giving birth to twins she became a stay at home mom. Once the kids where off to school she decided to take up a part time job with us in material testing. I would guess her to be 5'8" 130 pounds. With long legs, long dark brown hair, a nice ass, and good sold c cup rack. Of all the people in the company I find her the most difficult to work with. She has been in our country longer than her original but still has a terrible accent, a strange way of speaking, and an attitude that says she is never wrong even when she has no idea what she is talking about.
The fourth member of our merry band doesn't even work in our company, Dee. Dee's husband is a new hire in the field department and a very good friend of the boss. Dee is also a very good friend with the boss's wife. Which explains how she got an invite I guess. Not very fair to all the other wives and girlfriend in my opinion but then again not my money. Dee is taller perhaps 5'10". Medium length almost black hair around a pretty face. The few times we have met she has come across as a no nonsense person with a very smoky attitude. She a little wide in the hips, but has a nice pair of breasts that she likes to show off whenever the mood strikers her. (As I found out at the company Christmas party.)
And finally there is Summer, the Boss's wife, and 49% owner of our little company. As I stated earlier she's in her mid 30's with wild red hair past her shoulders and can be a bit of a hot head at times. She stands around 5'6" with dark brown eyes. Despite having 3 kids she has held it together fairly well. Her legs and ass are as great as I remember from the high school track team and it seems her breast had grown into a nice B cup at some point. She seems to hide her mid-section saying she's a bit stretched out from child birth. We have known each other since high school but we ran in different circles. After high school we always seemed to bump into each other every so often at college or a mutual friends party. Then after not seeing each other for a few years I was surprised to see her when I came in for an interview for a new job. I wouldn't be surprised if my employment is directly related to our previous acquaintance.
I have to admit I have a thing for her, she is pretty much the only reason I still work there. You see, I don't have to work. I come from a very well off family, and when my parents passed in a car wreck I took over there small fortune. I don't flash my money around like some do. I learned quickly that doing that draws an unwanted crowd. So, I took up a job, mainly to keep myself busy. I would have a girlfriend until she found out what I had. She would change from seeing me to seeing dollar signs and I would move on to the next one. I thought I had found one just before the Christmas party but I was wrong, very wrong. Which was how I ended up meeting Dee's nice pair if breast. (A story to be told later)
"Step over here Sir" she said.
"Ok no problem" I replied.
Arms out, legs spread, wand up and down left and right. This continued for some time, over and over.
"What is this lady trying to find" I wondered to myself.
Finally, with her magic wand resting on my groin "What's dis" she asked me.
"Just me mam" I answered.
"Well, I guess that's ok then. On your way" she said.
So I gather my stuff and head out to catch up with my party only to realize they were all standing there watching the entire situation.
"What was that all about?" asked Jodi.
"I think the security lady found something suspicious" answered Dee.
"Really...What?" replied Jodi.
"Nothing at all I'm sure" I said a bit embarrassed.
"I doubt it was nothing" Summer said cryptically. I looked at Summer and she gives me one off her sly little smirks.
"If you wanted to go back and get her number we have time before our flight" said Summer.
"Not necessary" I replied "I don't think she's my type..."
"Oh, I get it!... so what IS your type?" Jodi asks.
Fortunately I was saved trying to answer that loaded questions by all the other ladies laughter. Even quite little Ann gave a mousy little chuckle at that; witch surprised me to no end since I don't think I've ever heard her laugh.
We managed to board the plane without any other complications. As we sat in our seats waiting for pilots to get the go ahead for take-off. I couldn't help but look out the window and see the snow start to really come down. Light flurries my ass. How can the weather guys by so wrong so often and not get fired I asked myself.
"Oh my GOD are we going to be able to take off?!?!?!" came screeching into my ear from Jodi who had appeared out of no were. I looked past her to Wynter and Dee who were sitting in the other row of seats next to us.
"I hope you don't mind, Dee asked me to switch seats with her so they could talk about their kids or something."
"No problem I guess" I lied. As the plane started to taxi out on the runway, I looked to Jodi and said "see no worries here we go."
"Can I hold your hand? I hate take offs and landings" asked Jodi.
"Sigh, no problem" I replied as I looked past her to the other girls who were both holding back laughter and trying to covering smiles. You might be asking yourself what the big deal was. You might be saying "here is a cute young lady that is trying to jump you. So what if she's a little plump? Better than nothing. You are single, so what if she's engaged to some other guy. Give her what she wants and let the other guy deal with it." And you would be right. Except, I told myself back when I became single again that it's never a good idea to shit where you eat. And I was really trying to stick to that. Don't get me wrong all 5 of these ladies are extremely doable. And more than once, I've thought about trying to get with all of them. (Some more than others).
I just had to tell myself "I'm headed to an all-inclusive resort in the beautiful country of Mexico where any number of single, attractive ladies will be waiting for me to buy them free tequila and margaritas." So you can understand why I was a little hesitant to give Jodi any reason to get the wrong idea. After what seemed like an eternity the plane leveled off and the seat belt sign came on I disengaged my hand from Jodi and headed for the restroom to unload the 4 soda's and 1 coffee I had to drink that morning. No sooner than I had locked the restroom door and unzipped my fly I heard a knock at the door.
"Just a second" I responded
Knock knock was the reply. Jeese can't I get a moment alone? If that's Jodi wanting to join the mile high club I'm going to shut her down completely. I finish by business and wash my hands to the sound of another nock on the door. I swing the door open about to go off on Jodi but to my surprise its Dee instead.
"All yours" I say as I try to slide by her. She steps halfway in the door as I'm half way out. Now we are chest to chest and I'm looking at some glorious cleavage.
"Like what you see? Or do you prefer what Summer has now?" she asks.
"I saw you in the car checking us both out" she said a little angrily.
"Ah well..." is all I'm able to stammer out before she presses her tits against me. And says
"You liked my tits at the Christmas party" she told me. (A completely different story)
"Listen, I'm sorry about what happened at the party. I had just broken up with my girlfriend and maybe had a few to many"
"So you're saying you didn't like sliding your cock between my tits and Cuming in my mouth?" she says with an evil eye.
"That's not it at all" I pleaded "you were great; it's just that you are married to my co-worker and he's a great guy".
"If he's such a great guy why was he passed out on the floor at the party when he should have been in the bathroom with me instead of you? If he's such a great guy why is on his way to Canada to go hunting with the boys instead of fucking my pussy in this bathroom right now?"
"Here's the thing Dee... I don't know what's going on with you two and frankly it's none of my business, but..."
"But nothing Andy I got you off at Christmas and now you owe me one" she said as she pushed her cleavage flat against my chest and slid her hand over my crotch.
"Excuse me folks but you need to return to your seats if you aren't using the bathroom" said the flight attendant that came around the corner and probably heard every word we had just spoken. The sudden appearance of the attendant seemed to embarrass Dee enough to make her slid the rest of the way into the restroom and basically pushing me out into the isle slamming the crappy little bathroom door behind me. Now I had to hunch walk back to my seat trying to hide my bulging pants as I did it. Not an easy thing to do in the middle of a full plane with an all knowing flight attendant hot on my heals.
When I got back to my seat I found Jodi to be gone and Summer sitting in her seat. "What now" was the only thing I could think.
"What was going on back there? You have been acting very strange since we got on the plane" she asked me almost immediately.
"Oh nothing, just a mix up with the bathroom" I said as the flight attendant walked by while glaring at me the whole.
She didn't like my answer but let it go and said "Listen, I asked Jodi to trade me seats so we could talk for a minute."
"That's cool, what's up" I asked.
"We have been very happy with your level work over the last few years. You have really stepped up and taken over a lot of responsibilities without us even having to ask. You are one of the main reasons we can afford to take a trip like this." She said.
All I could do was nod my head and stair into her dark brown eyes. It took everything I had to keep my eyes above her chin. I knew that if I started following her freckles down into her cleavage I would be done for. In a split second I thought what if I took a peak what could happen... slapped, fired, and/or embarrassed. In the next split second I wonder where else those freckles went... breast, legs, ass, back, pussy? NO! Stop it!!! Slapped, fired, embarrassed that's the way to think. But the head in my pants was fighting the head on my shoulders.
"I'm glad you are happy with my work and that the company is successful..." I started to say.
"The other thing I needed to talk to you about was Jodi" she cut in.
"Now hold on a second, that's totally all her! I've been shooting her down left and right and..." I said trying to defend myself.
"I know I saw everything that's happened and heard everything on the car ride over. I just wanted to let you know that I know it's not you. My husband says he caught her with the shop boys in one of storage sheds a few weeks ago." Then she mumbled under her breath "I think he was following her to try and get some himself".
"Shop BOYS? Pleural??" I stammered.
"Typical guy" she smirked at me.
"You would get hung up on the fact that she was doing 2 guys and ignore the part where I thought my husband, your boss, wanted to do her."
The strange thing was she was smiling at me the whole time she said it.
"Well I ahhhh... well you know I am a guy" I said with my best grin. And an uncontrolled (hopefully unnoticed) eye flash towards that freckled cleavage.
"And the last thing I wanted to talk to you about was Dee. I know something is up with you two but she won't admit it. What's got me stumped is how something could be up with you two. You couldn't have met more than what 2, 3 times."
"Nothings up between us" I said as my grin became more forced than natural.
"Well that's a lie" she laughed "whatever it is I will find out. You know you can't avoid her the entire trip."
All I could do was pretend to sit there the rest of the fight to Miami and try to read my book. I don't think I made it 3 pages. All I could think about was Dee, Summer and Jodi and how I could avoid them and get out of this cluster I somehow landed in. at least the other two, Aznar and Ann, weren't giving me any trouble.
At last we landed in Miami. All we had to do now was get off the plane run from one end of the airport to the other and get on another plane. Somehow we got lucky and made it onto the plane with time to spare. Apparently a bunch of passengers that were also scheduled to be on our flight to Mexico didn't make it out of their airports, due to the unexpected massive blizzard that was now pounding the northern two thirds of the US (stupid weathermen). I imeditley pulled my phone out turned it on and received 3 text messages and 2 voice mails. All from my boss and Mike trying to get a hold of us to let us know they didn't get out before the storm and that the airport was closed. I turned to Summer and saw she was probably listening to the same message I had. She made the call home and got the news that "B team" would be trying to catch a flight tomorrow after the snow stopped and the runways could be cleared.
Just as we were settling in the head flight attendant got on the mike and told us that we were all that was going to be on the flight, so if we wanted we could spread out and get comfy as the plane was less than a third full.
"Finally some piece and quite" I thought. Unfortunatlly, as I sat in my seat trying to read all I could think on was the Christmas party where Dee blew me in the bathroom. How nice it felt with by cock between her tits and my head sliding between her lips. What if I switched Dee with Summer? I could just imagine her dark eyes and that red hair going up and down on my cock. Those plumb lips gripping my cock. Or what if I was the one that walked into warehouse as the stock boys fucked her front and back. One smacking into her fat ass from behind while she swallowed the others cock. I'm sure if she could handle two cocks she wouldn't mind a third. Perhaps it was time to move this to the bathroom so I could let off a little stress.
As I quickly walked my way to the back I couldn't help but be relieved that the plane was almost empty and nobody looked up as I shuffled by. Tried to open the door... locked... shit. Just as I turned to head to the bathroom at the front the door opened. And there stood Aznar.
She peppered me with "you need bathroom? You use bathroom a lot? Why you use bathroom SO much? You got problem?" pointing at my crouch.
"no no, no problem" I said back un intinonaly with a bad copy of her accent.
"You make fun of my accent? It not nice to make fun of others? I just try to help!" she spit out at me as she pushed past me. I could almost swear she squeezed my cock as she went buy. Surely I thought "that didn't happen" as I watched her sway her hips seductively down the aisle back to her seat. Just as a thought it must have been my imagination playing tricks on me she reached her seat bent over at the waist and shook her ass at me and looked me right in the eye and then winked. The very last thing in the world I expected to say the least.
"What the fuck is going on" I muttered. All but jumping into the restroom, locked the door, pulled my cock out and started stroking it like I was 5 and it was a new toy. Just as a started to focus on a confused image of all these damn women I work with. I heard a thump and a dig and the seat belt sign above the door came on followed by an annocement from the flight attendant to return to you seat and buckle up. As I stood there trying to decide what the hell I should do, I heard a "nock nock, sir I need you to finish up and return to your seat. We have some turbulence coming our way."