A Bets A Bet 1

Part 1

Big organizations love to have their national conventions in Orlando. People are more likely to sign up and show up when Disneyland is nearby (don't ask me why) and the whole city is a manicured wonderland with palm trees, waterfronts and plenty of public transportation to get back to your hotel after a binge drinking night with the buddies. "What goes on the road, stays on the road. . ." as any road warrior worth his salt will tell you.

I'd been going to conventions for 15 years, ever since I started working in sales for companies like IBM, HP, and Pfizer. I was heading the sales team for a start-up that had just closed its second round of funding and this Orlando conference was our big coming out launch party. Our product combined social networking, organizational training, and unique content that leap-frogged our competitors and put us 18 months to 3 years ahead of anyone else in the field. In the last 9 months since I'd come on board as senior VP of sales and business development I had racked up 150,000 frequent flier miles. . .not points, MILES. I'd built my team around quality professionals I'd worked with before as well as those who had been with the company from the time of its days in the proverbial garage (in this case the founders' basement). This convention was as much celebration for my team as it was about the sales meetings we'd arranged. The next four days and nights were going to be just as sleepless as the last 9 months had been, but for very different and much more interesting reasons.

This was why I was so excited to get out to the pool party I'd arranged for the sales team on the man-made lake of the Hilton Disney World Resort and Spa. Everyone had flown in earlier this morning and had either been out for a round of golf or spa treatments. Despite the economic tough times we had beaten our pre-launch targets by 250% and the management were falling over themselves to say "thank you" and "don't leave now and give our competitors the golden goose". Everyone was already out by the bar enjoying themselves and I beamed as I walked over.

I could see Gabby -- her big blue eyes unmistakable even at a distance, her fine brunette hair straight and obedient as always, her breasts still ample after her recent pregnancy and on full display with a plunging neckline in her flower-print yellow sundress. Next to her were Becka, Angy, and Tom. Becka was a sales veteran of 25 years with dark red hair, a perpetual Texas tan, and Sally Jesse eye glass frames that commanded the attention of any room she walked into. Angy was still in her twenties, barely 5 feet tall and a roly-poly fireball of blond ambition who owned the Midwest territory and who was looking as mellow as I'd ever seen her after an afternoon massage. Grinning next to the three lovelies was Tom, the 60 year old, steely-eyed, gray-maned former Marine who had followed me from HP and Pfizer to this shot at the big dollars. . .the REALLY big "fuck you" dollars that start-ups used to promise and this one had the chance to actually deliver. He'd gotten in his round of golf and was looking ruddy from the sunshine and no doubt his 3rd drink or so. . .

My attention was on the team and my anticipation was on my first Bombay Sapphire and tonic when I heard my name.

"Randy, hey Randy. . .over here," came the call. Now I'm an easy-going guy on most things, but one thing I make very clear to people, especially people I work with, is that my name is Randall, not Rands, or Ran-man, and sure as shit not Randy. It could only be one person calling me. . .and sure enough it was -- Cally Pines.

Directly in my line of approach to the bar and my mellow, fellow sales-warriors stood Cally with her marketing goons. These were the guys taking credit for our early sales success because of marketing bullshit they'd cobbled together and sent out at random to everybody on some list they got ripped off on from a broker. They always wore the fake smiles of Disney characters -- Goofy comes to mind -- and you had to watch your back for the inevitable knife they were preparing for it. The temperature around me dropped 15 degrees when I realized I had to navigate this snake pit before even getting fortified with a drink.

"Yeah, hey Cally," I said, deadpan. The VC-mandated board members were at the marketing table as well getting all manner of bullshit poured in their ear by Cally's pukes.

"What a great day, huh?" Cally said. "I love Orlando! Did you get in a round this afternoon, the fairways were super-fast."

The saccharine in her expression was making my teeth rot. "I had some customer meetings today, but I know Tom got a round in. I'm heading over to say hello to my team as a matter of fact."

Cally's team were all looking at us, waiting to see what would happen. It was no secret Cally and I didn't see eye to eye on how to bring in customers and how to close deals. She thought glossy postcards and coffee mugs were the way to go when selling executives and my "old-fashioned" view was that relationships and offering solid value was the way to go. I was sooo behind the times.

"That's so great that the whole sales team is here for our launch, you guys are really doing such a fantastic job. Congratulations, I just saw the latest numbers, you guys are really rocking and rolling out there!" I couldn't help but imagine her as a cross between a Disney princess and Barbie -- dirty-blond hair, gray-blue eyes and a plastered-on smile. Cally looked like Tea Leoni would look at 60 though she had just hit 40 the year before. I'm sure she had been a pretty girl when she was younger, but now the wrinkles and worry lines, and the thin, taut skin in the dark circles around her eyes were telling the story of someone in over her head and paddling with all her might just to stay afloat.

There was no love lost between me and her team: Lena, MarComm mistress of the dark who was an odds-on favorite of being a transsexual with her 6'2" frame, baritone voice, and NBA-sized hands; Krystal, the manic PR drone who was so hyper it seemed she would shatter into a million pieces at any moment; and Oswald, the Danish direct-marketing specialist who was the only competent member of the team but was so hen-pecked and dominated by his female colleagues that he came across as spooked and jumpy all the time.

"Okay, thanks for the kudos, um. . .good work on your collateral for the show, it uh. . .yeah, looks really professional. I'm sure customers will really love it." I was doing the act for the board members, Rick Jansen and Angela Cuvier, who had come from other start-ups they had helped to take to the IPO stage and were still getting the measure of the management team.

"Wow, thanks so much Randy, that's really nice of you," gushed Cally.

I nodded at Rick and Angela, "Nice to see you both here. I'd love to get you in front of a couple of customers in the next couple of days if you're available."

"That'd be great, Randall," said Rick. "Angela and I were just talking about how we'd like to sit down with you and really build on your early success. Maybe even learn a thing or two. . ."

Angela nodded and raised her glass, miming a toast, "Nice job, Randall, your team is really firing on all cylinders. Give them all our congratulations and we'll certainly make ourselves available for your customer meetings."

I could see that Cally's smile never wavered, but her eyes had turned cold and dark as a viper's. Ahh yes, I love the smell of corporate politics in the afternoon. . .

"So Randy," called out Cally. "Where are you taking your team for dinner?" She just couldn't let go: if I named some place cheap then I was a miserly boss, but if I was taking my team some place nice then I was a spendthrift. Ever the snake in the grass. Engarde!

"We're heading over to Sam and Delilah's -- it's supposed to be quite a good steakhouse and we don't have to cab it there and back. Gabby suggested it." Generous boss, but conscious of expenses. Riposte!

"Oh that's so cool," Cally gushed, "I love steak. My nickname in college was Cally the Carnivore. I mean I could really put it away: burgers, steak, if it was red meat I'd eat it." And she laughed loud as a hyena on the African plain. Then her team joined in to the yelping and guffawing. To give the devil her due, Cally may have put down the steaks and burgers, but she'd kept her figure into her 40's. But good Lord was she loud and abrasive! I exchanged a look with Rick and Angela as if to say: good luck with this one and received subtle grins in return.

"Okay, see you later, everyone," I said and waved as I made my way to the sales party that was in full swing.

When I got there Tom gave me one of his patented man-crusher handshakes, while Becka and Angy leaned in for European-style kisses on the cheek. Gabby flung her arms open and pulled me in for a bear hug that pressed her large breasts and toned body against me for a good five or ten seconds. My guess was she'd started drinking during her golf round.

"Well hello boss-man!" Gabby declared. "Nice of you to join us, now you've got to catch up because you are REALLLY behind. . . But cuz we know you and love you, we got you started already." And at this she pushed a tumbler full of clear liquid and just a couple of ice cubes in my direction.

"It'd better be Bombay Sapphire in there. . ." I said.

"We KNOW!" they all answered and fell back laughing. I put up my hands by way of resignation -- ya got me.

I raised my glass and said, "A toast: to the best damn sales team I've ever worked with, God bless revenue!"

"God bless revenue!" they all shouted and we clinked our glasses together spilling alcohol all over our hands in the process. That didn't stop us from downing our drinks in nearly one gulp.

Then it was on to another round. And another. . .

As the sun began to set in ochres and purples, and the breezes blew more chilly than refreshing, we headed inside to Sam and Delilah's, the five star steak restaurant at the Resort. Shrimp cocktail, 20 ounce steaks, red wine, more toasts. The night was flying by in the perfect way. We regaled each other with stories of our craziest sales calls, our biggest deals so far, and even to the big scores we were working in the weeks to come. By the time dessert came around we were all red-faced, hoarse from laughing, and on Cloud 9. There'd be a long day full of customers tomorrow, but tonight we were letting it all hang out.

In fact, some of us were letting more hang out than others. Becka had undone her trademark maroon jacket and it was hard not to stare at her D-cups straining at the silk blouse underneath. She may have been over 50 but she had a solid rack and firm skin. I kept having to snap my attention back to the conversation after my gaze would sweep over her cleavage.

Angy also had loosened up, taken her hair down where it hung past her shoulders, and kept hopping up and down during her stories making her own young, firm boobs jiggle noticeably. I could tell that Tom, for all his military-style presence, was having a hard time keeping his eyes off the girl who was younger than all three of his daughters.

The other thing I couldn't help but notice was Gabby, who was sitting to my right, occasionally rubbing her arm or her thigh against me. Or leaning way over to her left during a toast so her breast was practically falling into my plate. She would also give me playful punches on the arm whenever I'd get to the end of my stories. Yeah, there was definitely something going on there. . .

But that was the whole point of getting together away from headquarters, away from families, and without quotas or deadlines for these four days -- to let loose, flirt a little, drink a lot, create some personal connections and come out of it with enough momentum and excitement to tackle the next 9 months as the company barreled towards its IPO or acquisition.

We ordered dessert for the table, a chocolate soufflé bread pudding that gave you diabetes just looking at it. They brought five spoons, but I opted for a nice little dessert wine, Moscato d'Asti, to let the flavor of the top grade beef linger on my palate. The girls were having none of that! While Angy and Becka fed each other the soufflé from their long spoons with Tom looking on open-mouthed, Gabby insisted that I try the "oh my God this is just GORGEOUS!" dessert. She dug into the gooey center of the concoction and brought a heaping spoonful to my mouth. I opened wide and she slid it inside gently, almost tenderly. When a stray drop of chocolate escaped past my lips and down my chin, Gabby scooped it up with her index finger and licked it all up.

"Good huh?" Gabby asked, looking into my eyes.

"Hell yeah, but I bet it was better licking it off your finger," I said, a bit surprised at myself for going along with the flirtation. As much as I think that sexual harassment is pure bullshit, the last thing I'd wanted to do it screw up the dynamics of my sales team and get Gabby's head all turned around about her marriage, especially with a new baby at home.

But, damn, those blue eyes were magnetic, like tractor beams pulling me towards her. She had a freshness and energy about her that I always liked and that helped me hire her. Those qualities no doubt were a big part of her sales success. People like to buy from people they liked, and everybody liked Gabby. Her sundress showed off a few inches of cleavage; she'd had modest breasts before the pregnancy and it looked like she was proud to show off her new plus-sized tits (and no surgery!). Though the hem of the sundress ended below the knee it was easy to see she had been getting off the baby weight by exercising as her calves and the stray flash of thigh were muscled and toned. The fact that she had spent the night rubbing those legs and her arms against me wasn't helping either.

Still, we were just having some fun right?

After I paid the check, Angy had a brainstorm: let's all go to the club lounge in the Hilton, called Sunstar. The other gals loved the idea and pulled me and Tom by the hand all they way across the lobby and into the club. They played techno and club music and Sunstar was packed. Becka and Angy pulled Tom over to the bar saying they'd be getting us all drinks while Gabby pulled and pushed me onto the dance floor.

Dancing hadn't been my thing for a long time, since I'd gone out partying most nights while getting my MBA, but the motions and rhythm came back to me pretty quickly. It helped that Gabby was gyrating and grinding her way all around me. She would pull herself close and shimmy down to the floor stopping just as her face was level with my crotch. Then she'd do the same thing in the back and give my ass a squeeze.

I leaned into her and said through the din, "Two can play that game."

"I double-dog dare you," she laughed back at me.

We kept dancing but my eyes locked in on hers for those few extra moments that said, "Oh yeah, it's on!"

I moved closer to Gabby and put my hands on her hips. They were soft but firm with muscle. Giving me a smirk and with her eyes looking into mine, Gabby moved closer until our bodies were touching all while wiggling her hips to the beat against me. I spun her around with my hands so instead of facing me my body pressed against her back. Her full, firm ass pressed right against my hardening cock. I didn't even realize I was getting hard until Gabby pressed her ass against me and started to really grind it against my cock. She arched her back and wrapped her left arm around my neck as we swung around the dance floor. My hands moved just a couple of inches below her hips to knead her ass cheeks. My cock got harder and harder with every beat.

Front-to-back, and front-to-front we kept dirty dancing together for another few minutes until Becka, Angy and Tom brought our drinks.

"Cool down you too, pace your dirty selves!" laughed Angy. We grabbed the drinks and toasted again.

"To a great night with good friends," said Tom. Everyone echoed, "Cheers!" and down went another round.

What I hadn't noticed was that someone had brought along a tray of shots and now that we'd down another round they were passing around these small glasses with a pale gold liquid in them.

"There's NO way we're doing shots," I protested.

Becka slapped me on the arm, "Go on now, Randall, I've got 20 years on you and if I'm still drinkin', you're still drinkin'!" Then the shot was pressed into my hand and Gabby said the toast, "No rest for the wicked!" In one gulp the shots were gone: sweet like honey with a fantastic kick like getting rear-ended by a semi.

"What the hell was THAT?" I coughed and sputtered when I regained my breath.

"Oh, that's potchian," said Angy, "my boyfriend introduced me to it when we went to Ireland last year. It's strong huh?"

Everyone nodded and then we got back to dancing. It was almost impossible to hear each other in the club so we flowed in and out of dancing with one another and in a big group. After another shot of potchian however, Tom and Angy paired up and disappeared into the crowd and Becka winked at me and grabbed a guy who looked to be in his 20's and began throwing all her moves at him. He just smiled and went with it.

Gabby and I were alone and red-faced and sweaty in the crowd. She pointed for us to head off the dance floor and into the slightly quieter lounge area. I grabbed her hand and made our way through the crush of dancers and on-lookers.

When we got to the lounge and sat down for a minute, Gabby said, "I hate to do this, Randall, but I've got to head back to my room -- I'm exhausted and pretty drunk." I could see she was right: there were dark circles under her eyes and her cheeks were glowing a nuclear pink.

"Yeah, that's probably the right move," I said back in her ear. "It's been a long night and we've got three more just like it ahead of us coming up." As I talked to her I could smell her floral perfume and the clean smell of her hair, along with her dance sweat and the pheromonal tang of arousal -- it was more intoxicating than the potchian. "I'll walk you to your room, drunky."

Gabby laughed, "Okay, Mr. Sober."

We made our way out of the club and through the lobby of the hotel back to the elevators. As we waited for the elevator I had my arm around Gabby's waist and she had her hand on mine. It was very casual, relaxed. I could feel the throb of my cock from our earlier dancing, but I was keeping my breathing deep and even. Gabby settled her weight against me and sighed a little.

When the elevator arrived we stepped into and I pushed 17, Gabby's floor. "You're a really good dancer," she said, breaking our mutual silence.

"Well thank you, you're pretty good yourself. I haven't danced that much since B-school."

She looked mischievously at me and said, "Oh, you were dancing pretty hard alright."

As flushed as I was, I'm sure I turned several deeper shades of red at that comment. "Hey, that was all your fault you know. Tossing that ass around. . . I'm just a man after all, not a wooden statue."

"There was plenty of wood on that dance floor," she kept mocking me as she leaned her body against me. I couldn't decide if I wanted the elevator to speed up or slow down. I could feel her body through her dress brush against me and my cock was reacting just as it had on the dance floor.

"Feels like you know your way around the hard wood," was all I could think of. I had thrown myself into this job after my divorce five years ago and besides the odd fix-up from friends or a celebratory strip club outing with the guys I really didn't do a lot of sex. . .anything! So here I was in a hotel elevator getting hit on by a work colleague who was a subordinate and married, and I was completely out of practice of feeling this horny around a woman. Every Michael Douglass movie I'd ever seen with dangerous women flashed in my mind -- Glenn Close, Sharon Stone, Demi Moore -- but it did nothing to cool my blood or ease my hard-on.