A Bet's a Bet

"Mmmm, I sure do know good wood when I see it," purred Gabby and ran her hand down my crotch and over my stiff cock. Then she gasped and looked at me surprised, "God Randall, I suspected you were packing, but that's a Louisville Slugger in there!"

The only thing that gave me a reprieve, however momentary, was the elevator gliding to a halt and the doors sliding open.

"Walk me to my room?" Gabby smiled at me wickedly. I just nodded and followed.

She led me by the hand to her room which was in a small alcove at the end of the corridor. She reached into her purse for the electronic key, but then without warning whipped around and grabbed my neck with one hand and my cock with the other and planted a wet, drunk kiss on me just to the left of my lips. She tasted of alcohol and sweat, and a citrusy lotion, musky perfume, and the effulgent glow of trangressive need. An irresistible cocktail.

My body reacted for me: I answered her kiss with my tongue, exploring her mouth and tongue with my own; I pressed her against the door of her room and myself against her, my manhood insistent and hard against her belly; my hands slid down to her hips to keep her against me; I felt her nipples stiffen against my chest as our bodies flowed against each other. Our kiss lasted long minutes, or it could have been the whole night.

Finally I broke our connection. "Good night," I rasped.

Gabby looked at me with eyes glazed over with arousal and desire. "Mmmm, it could be an even better night. . ." She let that hang in the air between us as she fished out her key and waved it hypnotically before me.

I wanted to go into her room more than I'd wanted anything in a long time, but I wanted a small bit of sanity and self-respect more. I didn't know if I still had any left of either, but I'd check after a freezing cold shower in my room.

"Let's pace ourselves, get some sleep. . . Good things come to those who wait." Still weak, but my brain wasn't getting most of my blood at the moment.

"Good things coming. . .you're quite the dirty one aren't you. . ." Gabby said, and then she laughed. "I'll see you again after I get some sleep, don't think you're off the hook, boss-man." And she pulled me in for another hug. "Not off the hook by a long-shot," she whispered. I kissed her cheek and she stepped into her room.

The door clicked and the last thing I saw were her blue eyes staring at me, daring me. Double-dog daring me. I stood at her door for a couple of minutes, smiled to myself wondering if she was looking at me through the peephole, then I turned and walked back to the elevator.

Part 2

Luckily my wait for the elevator was brief and I didn't have to share the elevator with anyone wondering what the hell I was doing sporting a raging hard-on, sweaty and reeking of alcohol. I exited on 24, my floor, and as calmly as possible, made my way back to my room. Which was where my luck ran out.

The door next to my room was open and Cally Pines was standing in the doorway laughing and flirting with Rick Jansen. Rick looked half in the bag himself, had his suit jacket thrown over one shoulder and was leaning on the door jamb. Cally, incredibly, was wearing only a button down Oxford shirt and, as far as I could tell, nothing else! Her legs were pale and spotted with freckles, but they were certainly one of her best features -- firm, muscled, long. Her feet were broad and spade-like, with the toenails painted a dark, brick red color.

I tried to just nod an acknowledgement to them and to slip into my room, but my door was literally right next to Cally's door. "Who the hell designed this damn hotel?" I thought angrily to myself. "And why the hell do I have a raging hard-on and my card key isn't working while I'm getting more aroused by Cally's legs and Rick is looking at me blearily and with visible discomfort?! I can't save everybody, buddy!"

"Hi Randy," chirped Cally. "How was your night with the sales team? Bet you guys had a lot of fun. Did you go out after dinner?" I could swear her gaze was locked in on my crotch while she was talking.

Good Lord she was nosy, "Had a great time, and then made our way to Sunstorm, you should check it out," I said. 'You should check it out'? what the hell was coming out of my mouth? 'Just get in the door, Randall, nice and easy, smooth and simple. . .'

"Randall," said Rick.

"Rick," I said. "Good night you two, see you bright and early."

"G'night Randy," crowed Cally.

And then the door lock clicked and the door was open and I shot into my room and pushed it shut behind me as fast as I could. 'Great timing, Randy,' I thought to myself. 'Anyone else you'd like to show your hard-on to tonight? Anyone? Maybe Becka and Angy didn't get a good enough look at the club. . . Maybe Tom wants to have a competition about old guys getting hard-ons with younger girls? Idiot!'

But there was no use now wishing I had stayed with Gabby, or wishing I had calmed down my cock before heading upstairs. . . It was time for that cold shower and some sleep. I kicked off my shoes into the closet and stripped off my pants and shirt into my laundry bag. The cold water was bracing and got my blood pumping somewhere other than my loins for a change. My brain was finally starting to work again. My body was cooling down and sense was returning, however slowly, to the rest of me. I wasn't worried about Gabby being hurt or "weird" the next day, the only thing I was thinking about was what the hell I meant about us "pacing ourselves." Was that some kind of implicit promise of. . . what. . .sex? I really needed to get out more.

I'd dragged a brush through my hair and was winding down my speculation for the night when I heard a knock at my door. Who the hell could that be . . . at 2 in the morning, in Orlando. . .? The night was getting weirder and weirder.

Instinctively I grabbed a towel and held it around my hips as though someone could see me through the door. I peeked through the peephole and called out, "Who is it?"

The sight and the answer came at the same time: it was Cally. "It's me, Cally," came the slightly sing-song, slurred reply.

Just when I didn't think the night could not get any stranger and out of control, there she was -- the queen of loud and the princess of cheesy.

"It's a little late, Cally. . .are you locked out?"

"No, it's just. . .well, can I come in? I kind of need to borrow something."

"Cally, come on, it's 2 in the morning, ya want to just grab some sleep?"

'Kind of need to borrow' -- the quintessential weasel phrase -- as little information as possible as blandly as possible, no doubt meaning she needed to take something pretty expensive and important. At 2 in the morning. . .in Orlando. . .and me standing there with just an over-sized hand towel covering my goods. But I'd be damned if I was going to get dressed and be put out because some drunken, corporate climber needed a power cord for her Crackberry, or whatever the hell she wanted.

Neither of us said anything for a long minute.

"Please," she paused, "Randall, if you let me in I'll let you in on a secret. You'll like it, I promise."

A friend of mine grew up on the East Coast, in Philly. He would tell me that during winter the biggest danger to drivers wasn't the snow or even rain, but black ice -- water that had frozen and re-frozen so flat and slick that you couldn't even see it. When a novice driver hit black ice and started to skid inevitably he would yank the steering wheel of his car in the opposite direction of the skid in order to regain control and to "get his wheels back under him". This was exactly the wrong thing to do as the over-correction produced a fish-tailing vehicle out of control and careening dangerously across the road. What experienced drivers had trained themselves to do was to 'steer into the skid' -- to turn the wheel in the direction the black ice had thrown them in order to use the car's momentum to get them through the frictionless surface and onto safe ground. Only by doing this could you minimize the damage of hitting black ice and increase your chances of getting back on the road in one piece.

My friend and I had adopted this term -- 'steering into the skid' -- to acknowledge that sometimes when a situation at work or in personal life hit unexpected bumps and left you feeling out of control, despite wanting to fight for the control, instead the best thing to do was to let go and go with the flow. To steer into the skid. That way damage was minimized and you could regain control much faster. At least that was the theory. . .which I was now in the process of testing in my hotel room engirdled only by a hotel towel.

With one hand holding the towel in a firm grip around my nethers, I opened the door with my other hand. "Sure, Cally, come on in. . .what can I do for you. . ."

Cally made her way into my room and leaned against the door to close it. She was still wearing the button down blue Oxford that made it look like there was nothing underneath. I also noticed that the shirt was unbuttoned down to her solar plexus and that her nipples were hard points protruding through the cotton weave of that shirt. Unfortunately I also noticed that her breasts were larger than I had ever guessed. Without a bra they fell 5 or 6 inches lower than I was used to seeing in the office. She was easily a D-cup with an impressively flat belly above those long, toned legs. Noticing all this was quite unfortunate because the erection that the cold water had worked so well at counteracting, the sight of Cally had enflamed anew. The inadequate towel grew only more inadequate by the moment.

"So. . .," I started, "what, uh. . .can I do for you? You said you needed to borrow something?"

"Hmmm. . .," Cally paused and I could see her looking me up and down, mostly down. "Well, Rick was over and we kinda went through all my little bottles of Jack. And all the Cokes. . ." She giggled. "Now he's gone and I could use a little nightcap for the road, ya know?" Then she smiled. It may have been the first genuine smile I'd seen on her. One without calculation spinning in the difference engine in her hominid cranium. Not that I was going to turn my back on her for a second, but clearly tonight was having its eerie effects on everyone.

"Help yourself, my mini-bar is over by the TV," I motioned with my free hand over to the 50" LCD screen hanging on the opposite wall.

"Cool, thanks," said Cally and wagged her hips all the way across the room. I watched her pad across the room barefooted and couldn't see an outline of underwear under that shirt, but it was just long enough to not show off even a flash of ass cheek either. Blood thundered in my ears as I wondered how she was going to get her drinks from the little mini-bar set down low on the floor.

I found out right away: Cally got on her knees and wiggled her ass as she cleaned out my stock of tiny liquor bottles -- Jack Daniels, Southern Comfort, Tanqueray. . .pretty much everything in there.

"Those are coming out of the marketing budget," I said. When she turned around I could see she had snagged over $100 of mini-booze from my fridge.

"Relax, Randall, I'm always good to my friends," purred Cally. "And anyone who lets me into his room at 2 in the morning to snag booze is a *good* friend of mine."

She had gotten up off the floor with her boozy booty clutched to her chest pulling her shirt up another couple of inches up her thighs. I was glad that booze was all she needed because her body was sexy and having no uncertain effect on me. Even sitting on the bed and hiding my re-awakened cock I wasn't going to be able to keep it to myself for long. I needed privacy and soon to keep my interest under wraps.

"Okay, that's great, Cally. Enjoy your nightcap; I'll see you tomorrow at the show."

She pouted for a moment, "Aren't you going to have a quick drink with me, Randall?"

That was the second time she had called me Randall. She definitely wanted something, but this was no time to be building bridges. "I'll take a raincheck, thanks. I need the rest. Good night, Cally."

Never underestimate the power of a good silence. Cally knew she had been dismissed and after a few moments of quiet she moved towards the door. When she was just a foot or so from the handle, she turned back, "Aren't you curious about my secret, Randall?"

Almost free. "Why don't you tell me tomorrow. I'm sure the sales numbers or web pages responses will keep till then."

"Oh, it's got nothing to do with marketing, this is a private little piece of information. I think you'll enjoy it."

Good Lord this woman was getting on my last nerve. I could see how she had gotten to be VP of marketing -- stamina and persistence. Steer into the skid. . .

"Okay, sure, go ahead: tell me your secret."

Cally put her little bottles down on the dresser by the door and came back to sit in the armchair across from the bed. Me in my towel and her in the button-down, great examples of two professionals having a meeting.

She began, "You know how I tell people that I used to be called Cally the Carnivore because I eat so much meat?" I nodded. "Well, that's not how I got the nickname."

With this she put her feet on the floor and spread her legs a little. Another inch or two and I'd be staring right at her cooch. Just for a moment I wondered if she kept it natural, trimmed or shaved. I said nothing.

"My sorority sisters gave me that nickname, actually," Cally continued. "During my initiation they made me the 'coat check girl'. I thought the point was for me to dress slutty and take everyone's coat, but there was a lot more to it. To get into the house I had to suck off all the guys who came to 'check their coats.' And there were a lot of guys at that party. Sometimes two guys checked their coats at once."

Cally kept talking, but I couldn't really hear what she said. My heart hammering in my chest and the blood thundering through my ears drowned her out. All I could think about was this cute co-ed with her dirty blond hair and big blue eyes sucking off one frat guy after another, taking two cocks at a time. . . There was nothing I could do about my raging hard-on now, it was champing at the bit and the towel was a silly little attempt at modesty.

The next thing I heard was, ". . .and I couldn't even wipe my face the whole night. I was covered in cum till everybody left. The next morning I got my house invitation and my new nickname -- Cally the Carnivore." Now she sat silent, looking at me. . .double dog daring me to keep quiet.

"That's some story, Cally," I stammered. "College must have been quite the adventure for you."

She laughed, an easy laugh that was both giddy and world-weary. "Yeah, definitely an adventure. Every frat guy heard about my initiation and was getting me drunk so I would blow him. I guess one thing I got out of the whole thing was being great at giving head, there isn't a cock I can't deepthroat, and I've had more than my share."

Now she looked at me defiantly, waiting for me to challenge her cocksucking expertise. Leaning forward to give me a better view of her full tits. You doubt me, buddy? her posture said.

What I should have done is thanked her for the story and pointed her to the door reminding her of the hour. And maybe it was some kind of pent-up need or singularly clever devil who sprang to my tongue that moment, but what I actually said was, "That's definitely impressive, but no one has ever come close to deep-throating my cock. Not even close."

As soon as the words came out of my mouth I wanted to take them back, but you can't put the genie back in the bottle.

"Is that a challenge, Randall?" smirked Cally. She stood up and came closer to the bed. "You must have some kind of massive cock hiding under that towel. ..or maybe the girls you've been with weren't good at giving head."

As she came to stand right in front of me, she undid the last few buttons of her shirt and let it slip to the floor. "So you want to let me try?"

For all the political corporate bullshit that our relationship had been built on, my dislike for Cally did not blind me to her beautiful full tits, hard brown nipples, and worked out body. I also had the answer to the question that had popped into my head earlier: she was trimmed. I looked up at her challenging smirk, having completely lost control and now sliding on the black ice of co-worker sex, and said, "Sure, let's see what you've got."

Before I got the towel off me, Cally chimed in, "So what do I get if I win? Let's make this interesting." She had the body of a sorority girl, but the brain of a frat jock.

"Okay, let's make this. . .interesting then, but no work bets, let's make this personal," I offered.

She nodded, "Personal it is." We both thought for a minute then Cally's eyes lit up. "I got it: if I can deepthroat your cock, I mean really tongue your balls with your cock deep in my throat, you have to eat my ass. That personal enough for you, Randall?"

As she turned around to show me her ass, I could see that it had definitely gotten bigger since her college days, but was nevertheless firm and with no cellulite. I was never a big ass-eater, but what the hell, it'd be worth it to finally get some deepthroat head.

"You're on, I'll eat your ass if you can deepthroat me, but if you can't then. . .I get to fuck your ass. You game for that?" No one had ever let me assfuck them before, not drunk girls in college, not my wife of almost 20 years, not even any strip club girls after a crazy night of drinks and speed. But this was the art of negotiation -- win-win, mostly for me.

Cally hesitated. The stakes had gotten way higher than she imagined they would. ..but she laughed it off certain that she win this bet, "You're on, Randall. There's no way you'll be fucking my ass."

At this I pulled off my towel and dropped it to the floor. I guess I thought she would just drop to her knees and start sucking my cock, but she actually took a step back and swallowed hard.

"Jesus Christ, Randall, that's some fucking cock you've got there," she said, her eyes wide.

I'd heard similar exclamations from nearly all the women I'd been with. Not that the number was that great, but still, I mostly put it down to womanly flattery and a desire to get me aroused. I figured most guys heard "oooh, you're so big" like most girls heard "you're so pretty." A polite prelude to sex; an "I'm okay, you're okay" declaration to oil the socio-sexual machinery. With Cally, after her story of sucking dozens of cocks, was the first time I believed that what I was packing was more than average. It wasn't just the length either, I knew the girth was something that challenged some of the women I'd been with even for vaginal sex. Most loved it, but for some it turned out to be just too big.

"A bet's a bet," was all I said.

"I've had bigger," Cally huffed. Then she got on her knees and put her hands on my stiffening cock.

For all her posturing and boldness, Cally really did know how to handle a cock. Her hands moved up and down my shaft and rubbed my head gently getting my fully hard. She worked on my balls and licked nearly down to my ass. From all the teasing tonight, and the drinking, the dancing, the making out with Gabby, the tension with Cally and her revelation. . .my cock was raging hard. And Cally was using all her skills, working her way up and down the shaft of my cock, sucking on my head, working her throat open to take my girth and my thick head down her throat.

After 10 minutes she grabbed one of the little bottles of Jack and downed it in one gulp, all while stroking my cock with her left hand.

"Fuck, Randall, if I'd known you had this massive cock I would have come on to you months ago. You've got the thickest cock I've ever had."

"You're a goddam pro at sucking cock, Cally, I don't mind telling you. Really, nobody's ever worked my cock like you, but you've only gotten about halfway down. . .so. . ."