The Boss's Pool Party. (Closed for DeepBlue89)

[hcsd1719]

The entire encounter started out as one of the worst months I've ever had in my professional career. Let me set the tone for you. I work in Research & development for Ames Research on several Government contracts. The story always seems to be the same. Lowest bidder gets the work. We get to pick up the pieces when they can't seem to get it done. My Boss (Mr. Scarpotchi) is one of those rare guys who manages to somehow balance the "I need it yesterday" with our trials & tribulations of the team. I'm one of twelve that the big man directs and recently I've been running into walls of stress. "Great job Doug! I didn't think you'd get through that workload that quickly. I've got something bigger that I think you’re the man to tackle it!" Oh yay!... My shit luck lands me in the spotlight? And now Mr. Scarpotchi thinks I'm some miracle worker. Ugh...

It was almost overnight I went from the prodigal son, to the POS making the team look bad because Mr. S said I could easily rip right through it. Day after day I've had those one sided conversations that end up with me limping out of his office in front of the rest of the team.

Thank God next week is the Fourth of July. I could use a weekend off. Mr. Scarpotchi always throws his annual company pool party but I'm really not up to going this time around. It's always the talk of the town, but somehow I don't think the attitude will be so welcoming this time around.

I was out with a couple of my buddies shooting a little pool when one of them asked me if I was going to the party this year. I knew why they were asking. Two years ago there were all kinds of talk after one of the secretaries in the office hooked up with one of the Reps out in the Gazebo just as the fireworks started. The stories I told them had them all worked up for yet another tale to be told. Last year, Amanda tried to talk me into taking her to the party. She & I have been playing around with each other from time to time, but she was a bit too eager for me. I mean where's the hunt? I don't want a woman who's that easy. Give me something that's worth chasing.

I had told myself on my way home from the pool hall that I wasn't going to the party this year. I didn't want to embarrass Mr. S at his own home to say nothing for my own ego so when he confronted me at our very next one-sided conversation in his office about the party I almost fell out of the chair. "I sure do think you’re going to be missing out on making several contacts that would be good for your work." Holy hell... Guilt? I'm still taken back that he wants me there but perhaps that's just my own worry. Maybe he's not such a hard ass. "Now get that damn sensor fixed before the end of the week so we can send it out!" oh... there it was. Yeah, he's still the hard ass I thought he was. As I was walking out of his office thinking the day couldn't get any worse, "And I don't want to see you walking around the party looking like a kicked dog either!"

 

[DeepBlue89]

Natalie West
18 years old
5'9
~~~
​

I sighed at the mirror, observing my reflection with great unease. "What on earth was I thinking?" I thought to myself, turning around and seeing most of my body exposed. This all started with a bet; you see, I'm not someone comfortable with my body. It all started at the age of 14, when my curves began to develop. At first, I was fine with it, I guess - but now at the age of 18, I was self-conscious of how my breasts seemed to have ballooned and how round my ass was. For the longest time, I wore the baggiest clothes imaginable, desperate to hide my features. I avoided guys like the plague and all my friends were exclusively girls - and while they dated, I was always single and never really looked for everyone. So, when my dad invited us all to his boss's party, Ashley (my best friend) came up with the idea of us playing a game of cards. Easy enough, as I was the best among us but instead of playing for money, we played for bets. If I lost? Well, I needed to dress up in whatever she chose...and somehow, I lost.

So here I was, at my dad's boss's place, where I changed up in Ashley's room. The outfit was skimpy as hell - a flimsy pink bikini top matched with a thin fabric thong for the bottom. Not to mention, I needed to put on these three inch heels that Ashley dictated for me - I seemed like a porn star more than anything else. My dad wasn't going to be around, so at least I had that going for me.

"Coming out Natalie?" Ashley said from outside as I sighed, leaving the bathroom as I headed out.

She clapped her hands in glee and said "You'll find a boyfriend here for sure!"

"You know that everyone here is old enough to be my dad, right?"

"Oh, don't act that way. Come on, everyone is waiting for you outside."

"Ashley, I'm so embarrassed!" I said, almost pleading with her to let this go.

"Don't be, I've seen the women here and most are dressed like you are. Come on!" she then replied, dragging me out. Well, Ashley was just as bossy as her father, I guess.

 

[hcsd1719]

Party day has finally arrived. The remainder of the week wasn't any better than the last four but I was determined to live up to my end of the bargain. So he wants me to play the part? Okay I thought to myself. I'm a guy who's six foot tall, 225 pounds who lives at the gym or the pool hall on his time off. I wouldn't say I'm a monster, but for a guy of 30 I think I could pass for a college guy still. I grabbed my best pair of swim shorts, good shoes. Tossed on a Polo and headed for the car.
When I arrived I found a crowd I didn’t usually see at company functions. Several people here were Contractor Clients from the government, others were women who looked like they were professional escorts walking on the arm of some guy that looked like he belonged in the mafia. I spotted Jim, one of my team mates and a buddy who’s not shy around a pool hall so I hooked up with him to see how the tempo was so far.

“ Dude, I didn’t think you were coming tonight?”

Me either, but the Big Dawg didn’t really give me a choice. What’s it looking like? Think we can bail early without causing a scene?

“Probably. It looks like two kinds of people here. Ms. Ashley & her crew and people with more money than they know what to do with.”

Ashley? As in Mr. Scarpotchi’s daughter?

“The one in the same. She’s here with the CFO’s daughter too.

Get the fuck out! Mr. West’s daughter is here? Isn’t she the one who came to last year’s Christmas party wearing that baggy pant suit?

“ HA! That’s her, but you wait until you see her now! If she was ANYONE else, I’d be all over that!”


Jim was never shy around women. He’s been known to get himself into heated situations with some of the more attractive woman we’ve found at a club or the pool hall only to find out they’re married or someone who’s connected at work. Go figure that he’s been looked over for promotion five times.

 

[DeepBlue89]

The scene around the pool was something that I haven't even experienced; most of the people here looked really wealthy, to say the least...and much older than I was. I was extremely timid, and Ashley could probably see this too, as she nudged me into several conversations she was having with people from her dad's work. I was hit on, and stared at, more than I would have liked. I wanted to leave, sneak away from her view and tell her the next day that I stayed after all, but I knew that Ashley was too smart to fall for that.

"Come on Natalie, show some enthusiasm." Ashley said, looking a little frustrated over how quiet I was.

"I don't know what you want from me Ashley..." I answered nervously, as people were eying me from left and right.

"Have some fun! You're always so tense!" she said, a little too loud for my taste.

"Okay, okay, I'll try! I don't know how though." I replied, as we were approached by another group of people.

 

[hcsd1719]

Scanning the pool area I didn’t see anyone I didn’t recognize from work.
Patio? No, no one I don’t know there either.

“Dude, let’s get a beer & say hello to people.”

That’s not a bad idea. I could use something to calm my nerves.

I’m not usually this bad off. I’d consider myself confident and generally a fun person to be around but recently, I’ve felt like I’m walking on egg shells around people from work. Jim & I headed to the bar and ordered what passed for a beer at an aristocratic work function.

Then I saw her…

Stepping out from the house was a woman who I didn’t recognize but stopped me dead in my tracks. It was almost happening in slow motion. A cherry red, three inch Jimmy choo hugging the most perfectly shaped, toned & tanned leg I have ever seen. Then her body came through the doorway like she was gliding on a cloud. This woman had a body that looked like she lived at the gym and knew what she had. She was wearing… DAMN! I can’t… MOVE JIM! Frantic, I just about plowed through Jim to get him out of the way and knocked his beer out of his hand before it even registered in my brain what I had done. To this day, I don’t think I could tell you what Jim said to me. I felt like I was caught in space. She was wearing one of the hottest & revealing bikini’s I’ve ever seen. This Goddess was being hugged like a glove by her bottom’s. Her stomach & midsection was so tone, I wondered if her name was Aphrodite. She was spilling out of this tiny little top with two of the most magnificent breasts found at the party.

HOLY SHIT!!! THAT’S MR. WEST’S DAUGHTER!!!

Reality came down on me like a sledge hammer and all of a sudden the details of the last several seconds came flooding back to me. I looked around but couldn’t find Jim. I quickly scanned my surroundings to see if anyone had watched me make a fool of myself or my ogling of the CFO’s only daughter.

I fled the area and as calmly as I could, started casually looking around to see if Mr. West was attending the party. He usually comes to these things. He’s got to be here. I can’t find him. Where is he?

Doug, chill… What’s wrong with you, I said to myself. Just relax & everything will be cool.

 

[DeepBlue89]

"Okay Ashley, can we just go inside now?" I asked, tired of being looked at the way I was.

"No way, we're just beginning here."

"Come ooon..." I whined, as we walked around the pool.


Needless to say, I felt pretty uncomfortable the way that I was dressed. First off, I hated walking in high heels as I was at the moment. The clicking sound they made annoying me a great deal, as I was used to my sneakers (this is not counting how difficult it was to walk with these at all). The thong barely seemed to cover anything of my backside; my plump cheeks being visible a great deal for any of the wolves drooling all over me. My large breasts seemed hardly contained in the pink bikini top; the hefty orbs spilling all over my top as they strained to keep them in. Ashley seriously made me wear the polar opposite my usual concealing attire.

Lost amid my thoughts, I didn't notice Ashley motioning two people towards us.

"Hey Doug! Over here!"

"Oh my god, what are you doing?..." I asked, as the tall handsome man approached us.

"How have you been doing?" Ashley asked innocently "Have you met Natalie? Mr. West's daughter?"

"Hi!" I said a bit shyly, though maintained a tone of enthusiasm.

 

[hcsd1719]

"Hey Doug! Over here!"

Who? What? Me?

"Dude, are you okay? You knocked me on my ass. What were you looking at?

I was on sensory overload.

"Come on. Ashley wants to say hello.

Jim managed to find me and started tugging on my arm, pulling me toward Ashley.

Hold up! That's Natalie with her.

"Yeah so don't be stupid. Your acting like an idiot tonight & she's not the one you want telling her father you were an asshole."

As we walked towards to women I noticed that Jim was tugging on his shirt and straightening his posture. As we got to the ladies all I could do was stare at Natalie. My God she was gorgeous. I couldn't believe I was standing this close to a woman who got this kind of a physical reaction out of me.

Reality check! Everyone was staring at me. What did I miss? I thought to myself? Natalie was standing across from me with a half smile on her face nibbling on her lip. All I could think about was how those lips would feel on my shaft as I slid between them, or the moans that would come out of them as I lightly played with her clit.

"Um hi. Ahh hi Ashley, how are you doing tonight?

OUCH! Jim, gave me an elbow shot in my ribs. I looked at him only to find he was motioning me to actually look at Ashley while I was talking to her. I couldn't help myself. Here was this half naked woman standing in front of me who had me spellbound into desires to pleasure her.

 

[DeepBlue89]

He was looking at me a lot. I wonder if he could tell that I was blushing a bit...

"Um hi. Ahh hi Ashley, how are you doing tonight?

"I'm doing fine. We're just a little bored is all. Right Natalie?"

"Yeah, there isn't much to do here." I replied shyly again, trying to pretend that I didn't notice Doug's stares and lustful gaze. I hated wearing this...

"Are any of you looking for a date? Natalie is single..." Ashley said, as I elbowed her.

"Ashley!" I muttered loudly.

"Oh, could we hang around you two? Everyone else is such a bore...Hey, I know, do you two want to play a game? We have darts and stuff in case you're bored of business talks."

That Ashley, I wondered how she could behave the way she did. My eyes went back to Doug and I couldn't believe that he worked with these folks. He seemed more at home in a gym than an office.

 

[hcsd1719]

Before Jim could even get a word out, I blurted out;

" I think we can find some darts around here that will fit in your hands to use."

Did that just come out of my mouth? Before I knew it I was at it again but I couldn't help myself.

Guys vs. Gals! Natalie & I will make the walk to the other side of the yard.

As we were walking towards the grass area away from the group, Jim grabbed my arm.

"Dude, are you nuts? I wouldn't even fuck with that one. That's professional suicide served up on a platter."

"I know, but look at her. I don't know what it is about her but I can't stop."

"Well just don't go too crazy. I know you like your blonds, but that one is the spawn of death."

 

[DeepBlue89]

" I think we can find some darts around here that will fit in your hands to use."

Ashley didn't say anything, but smile. I, in the other hand, was a little confused. Regardless, we walked away from the pool for now, going towards somewhere a little bit more secluded; nearer to the garage. It was open, there were no crowds of people and everything was set up already.

"Who wants to go first? Red darts are for me and Natalie, blue darts are for you two" Ashley said, handing them over "What are the stakes guys?"


"Stakes?" I asked "I don't have any money Ashley."

"Don't worry about it. I'm sure that they'll think of something."

 

[hcsd1719]

Jim frantically looked at me with a look of Don't Do it!


"The stakes shall be, the loosing team needs to dance for the winning team.

I heard a gasp come out of Jim. Dougie, if you get us in trouble I'm going to take it out on you!"

" Don't sweat it bro. A little tease dance isn't all that bad. It's not like I said they had to strip & fuck us. Now get down there with Ashley & send Natalie down here. Team mates need to be on opposite sides so we can throw them back."

"I don't know if I dare leave you down here alone with Natalie. She doesn't look like she's into this. I think your barking up the wrong tree.

"Oh, quit being a pussy & get down there. I happen to know you've been staring at Ashley's breasts all night long."

What do you think, Ladies? Does that bet work for you?

 

[DeepBlue89]

"The stakes shall be, the loosing team needs to dance for the winning team. "

"Okay, sure." Ashley said with a grin "What do you think Natalie?"
"I guess that isn't a big deal." I answered back, wondering what kind of dance he was thinking about though.

They were arguing a bit, but over what - I had no idea. Pretty soon, they seemed to have fixed whatever was the matter and..

"What do you think, Ladies? Does that bet work for you?"

"Sure." I said, feeling a bit of a thrill. Ashley on the other hand...

"What kind of a dance? Is that something that only the winner decides?" she asked, before nodding "Okay, let's do this."

 

[hcsd1719]

"Oh now Ashley, where's the fun in knowing in advance?
My heart was pounding. I wasn't acting like myself at all. It was almost like I was watching this from outside my body but I didn't care. There was something about Natalie that I had to have. That innocent yet dominating personality, or perhaps that was only the persona we all put on her because of her father. Either way I didn't' care. I had to pleasure this woman. I had to make her eyes roll into the back of her head.

I could hear Jim mumbling something as he was walking down towards the ladies but I couldn't make it out over the pounding of my excitement.

It took a couple of minutes before Natalie started her way towards me. I could see the three of them exchange words briefly, but I didn't care. It was almost like being at a fashion show watching her walk towards me. Stride for stride she bounced her way along. Every step was another shot of adrenaline into my system but I knew I had to play this cool if I was going to have a chance in hell to say nothing about keeping my job. Was that it? Was it the danger stigma that was attached to her?

Hello. I said to her. Nope. It was her all by herself.
I'm Doug. My friends call me Dougie. I extended my hand in an attempt at breaking the ice with her.


Have you ever played this game before?

 

[DeepBlue89]

Ashley sure was a chatty woman; Jim and her really began talking, so much so that I thought that we were going to drop the game. Eventually, they stopped and my friend told me to go over to Doug, since we were paired together. I saw no reason to object, as he seemed like a nice guy.

I got to him and smiled.

"So, we're paired up together huh?"

We introduced each other, him starting with:
"I'm Doug. My friends call me Dougie."
"Nice to meet you Dougie. I'm Natalie." I answered with a smile.

"Have you ever played this game before?"

"Darts? Yep. This particular game of darts? No way." I replied with a chuckle.

 

[hcsd1719]

Oh, well if you'd like I'd be happy to give you a quick lesson. We can't have you betting something this serious without knowing what your doing.

She looked so hot standing there. Those heels made her legs & ass perk up but it didn't look like they needed any help what so ever. And her breasts... I wouldn't consider myself a "Tit guy", but her pair was making me come around to seeing it.