Short sex stories

Erotic fiction and short sex stories




A Bet's a Bet

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.
"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. . ."
She attacked my cock with a new vigor. It felt as though she was impaling her throat on my cock over and over. Her mouth and tongue and her hands felt amazing running up and down my cock and over my balls. Without thinking about it, I leaned over and played with her tits. They felt smooth and warm in my hands as I kneaded them and pinched the nipples. I heard her moan at that.

"Please, play with my tits, it gets me so fucking hot, put your hands on my body," Cally moaned and pleaded.

I squeezed her tits harder and let my hands roam over her freckled back and over her ass cheeks. As she gagged, I could tell Cally was inching closer down the shaft of my cock. She was playing with my balls and I realized she was trying to pull them closer to her mouth. Trouble was for all my cock, I've got barely any scrotum, it's a tight package at the base of my cock that melds seamlessly into my perineum, the taint.

After 20 minutes, I was getting ready to cum, I could barely hold on. "Concede yet, Cally?"

She took her mouth off my cock and looked at me. "Randall, fuck my throat, get your cock down my throat, even if I gag keep fucking me, I can't take that cock in my ass. Please fuck my throat. . ."

Her pleading tripped a new switch in me, a place I didn't know existed. I stood up and grabbed her head in my hands, I drove my hips back and forth, my cock sliding in and out of her mouth and throat. I'd never fucked my wife's throat like this, our lovemaking was too personal and intimate for that. Even the strippers never threw themselves at my cock like Cally was doing. I *wanted* her to take my cock past her gagging point. Without reservation I fucked her throat like the drunken, heedless idiot I turned into.

And still, no matter how hard I fucked her, past her natural limits and the gag-spittle that poured from her mouth, her tongue couldn't reach my balls. The harder I tried fucking her the closer I was to cumming. All of a sudden I went over the edge, I was going to cum and no force on earth could stop me. I kept fucking Cally's throat and hearing her gag made me lose final control. . .

Without pulling out I came stroke after stroke down her throat. She choked and sputtered. I felt the great spurts of semen launch into her. Some she swallowed but a lot she choked out to let it run down her cheeks and chin to mix with her spit and. ..were those tears running down her cheeks?

It was probably no more than 30 seconds, but I felt like I came down Cally's throat for a long time. When no more spasms wracked my cock and my hips, I pulled my slick shiny cock out of her throat.

Cally's face was wet from tears, spit, and my cum. She was breathing hard, catching her breath. I sat on the bed with my cock dripping juices onto the carpet and watching Cally's breasts heave up and down as she caught her breath. The towel was on the floor where I had let it drop and Cally pulled it over to wipe her face clean. Once she had cleaned herself, she crawled over and wiped my cock clean.

Looking up at me she said, "That was the thickest cock I've every sucked, Randall. You should have warned me."

With all the tension having shot out of me with my ejaculation, I laughed at that, "I *did* warn you!"

"I guess you're right, I should have listened," she admitted. "It's lucky for me you came, so you can't collect on our bet," she added slyly.

"Oh Cally, you'll want to grab another couple of those little bottles, because I can cum half a dozen times a night and I'm just getting started."

"Come on, Randy," she whined.

"First of all, that 'Randall', is that clear?"

She gulped, "Sorry, yes, Randall."

"And second of all," I began, then paused. My phone was lying nearby on the night stand. I reached over to it and pulled it over. Cally gave me a quizzical look. Until I brought up the phone and snapped a picture of her sitting naked on my hotel room floor.

"What the. . .what are you doing?"

"Second of all, what would your husband think if he got a photo of you in another man's room with tonight's time stamp? Pretty awkward conversation, right?"

She sat there dumbfounded. "Are you fucking *blackmailing* me?"

"Oh the picture? That's just for my personal use, for posterity, you know. I just know how unreliable digital technology can be with hacking and email piracy."

"Randall, please. . .," the situation was starting to sink in.

"I don't want to make any trouble for you, Cally, but I do want to fuck that ass of yours. A bet's a bet, right?"

She looked down at my cock that was already half hard again from just the past couple of minutes.

"And if I let you fuck me, then. . .we're cool, right?"

"Of course, I always honor my word," I held up my hand in a "scout's honor" salute.

Part 3

There was a moment of calm. What began as a sexual game had turned much more sexual and suddenly, for Cally, much more serious. She couldn't have imagined losing that bet and getting her ass fucked but a cock that wouldn't even fit down her well-used throat. Now she was on the brink of a co-worker who had her on camera naked in his hotel room readying to blast her tight asshole with his outsized cock. It didn't take much of my imagination to understand her confused, tired, and scared position.

And while the better angels of my nature wanted to let her off the hook, the pent up devils of frustration having had to put up with her company political bullshit made me want to collect on my bet. I wasn't going to be heartless about it though.

"Hey Cally, what do you say to us fucking first? It'll relax you and I bet you like your ass played with anyway."

She looked at my flaccid though still thick cock hanging down my thigh and, I couldn't believe this, smiled a little at me.

"Since I saw that fat cock, Randall, I've been hoping you'd fuck me with it. Do me from behind too, like a bitch at your cock, fuck me deep. That'll get me crazy. . .maybe enough to let you break my asshole." There was both greed and fear playing across her face.

I stepped across to wear Cally sat on the floor and lifted her up to sit on the bed. Feeling her skin on my fingertips, smelling her sweaty and fragrant hair, I couldn't help myself -- I leaned down and kissed her mouth. Tasted her salty, sweet breath, like honey roasted nuts. Cally tasted good, and smelled both of sex and of exertion. My cock stirred again thrilling for what was to come.

Either by instinct or need, Cally's hands stroked my cock as we made out on the hotel room bedspread. She worked it across her chest and her hard nipples. Her moans excited me and I became harder and thicker in her hands. Moaning louder now, Cally reached one hand down between her legs and slipped two fingers inside her well-maintained pussy. Into my mouth she breathed the words, "God fuck yes, gimme that huge cock, Randall." She was calling me 'Randall' now and I liked the sound of her compliance.

Then the fingers of her right hand were on my cock slathering it with her pussy juice. She covered my throbbing head and stiff shaft running her fingers up and down. Our tongues were insistent and urgent now, probing and thrusting deep into each others mouths. As much as I enjoyed the feel of her mouth on mine and her hands anointing my cock with her sacred nectar, I needed to fuck her and NOW.

My hands were on her shoulders and I pushed her back on the bed. She looked at me with eyes ablaze with a dark hunger, a deep unfillable need that illicit danger and hyper-sensory experience could temporarily satisfy. I grabbed her thighs and moved her legs higher and wider apart; then my hands were on her ankles, she was on her back on the bed and her ass barely supported at the edge of the mattress.

She began to say something, "I need more sup. . .", but she never finished, I pulled her legs up a little and thrust my cock inside her wet cunt. Not all the way at first, just the thick head and an inch or two of the shaft to feel her warm wetness on me.

"Ahhh,. . .God, ahhhh," Cally stifled a scream and moaned like a wild animal. "Holy shit, god, please. . .oh shit, Randall, fuck that's too big. . ."

Those sounded like pleas to stop, or at least slow down, but not to the primitive, reptilian part of my brain that ruled me now. To that muck-dwelling survivor of a thousand challenges to its being these sobs and squeals were red meat and meant it would feed and live another day. I got harder, my cock grew thicker and slide further into Cally's drenched and hot pussy.

I looked down at Cally and her eyes stared back at me. The eyes that looked back at me were not the scheming, Machiavellian eyes of a co-worker or ladder-climber, but the eyes of a rutting beast both joyful and challenged at the new boundaries of its existence. She was being stretched wide, and she loved it, and still some small warning klaxon of self-preservation bleated in her brain that this thing invading her, this cock that was bringing her pleasure, would soon likely ram itself, perhaps somewhat slowly but more likely with an undeniable force, into her all-but-virgin ass. This combination of pleasure and fear drove Cally's human niceties from the field and looked out from her yes like a Fury that would have its justice. At another time I would be scared in my guts from a look like that, but at that very moment I reveled in the raw state that was as natural for me as breathing.

"Fuck me like a bitch, Randall, turn me over and fuck me deep," Cally pleaded.

Without a though I grabbed her hips and swilled her with my cock still embedded in her. She grunted and her sweat was on my hands. Freckles and droplets of sweat covered her ass and her back. Now my hands were on her ass and spreading her cheeks wide. My cock drove deeper and deeper into her pussy.

"Stop, goddam it, fuck please just stop!" she begged. I stilled for a minute with my cock deep in her pussy, about three quarters of the way in. Just a couple inches of my cock were still visible. I didn't say a word. Just stayed still with the veins in my cock throbbing with blood.

"Okay, okay, damnit, I've gotta catch my breath, shit," Cally gulped air. "Fuck, Randy, you are stretching my pussy. . ." She didn't get the chance to finish.

The word "Randy" erased all conscious forebearance from my brain; I slammed the rest of my cock into Cally's pussy.

"Oh God, ahhhhhh, shit, sorry sorry," she sobbed.

I slid my cock out slowly, an inch at a time, as she exhaled and was about to take another breath, I slammed it back inside her.

"Ow, fuck, oh God, Randall, Randall," Cally's voice was cracking and squeaking.

I fucked her steady now, the rhythm of a piston in a recalcitrant housing, in then out, out then in, again and again. . .

"Oh holy God, oh fucking yes, please keep going, fuck me fuck me fuck me hard!" she spit and snapped into the bed spread. I was only too happy to oblige.

For one minute, then two, then three, I kept fucking her from behind. Her head buried in the bedspread, her hair wet from sweat and effort, her pussy red-raw from being stretched and abused, her back still a cello of skin over muscle and bone -- elegant, smooth, peerless. Cally's breathing was steady now and an electric purr rumbled from her throat and pulsed through her body.

We had settled into a brutal but welcome rhythm, Cally's moans came out almost satisfied, maybe even relieved -- some need was being satisfied that she hadn't been entirely aware of, couldn't have articulated, but here it was, a space that was empty being filled, a void being put right, and leaving a sense of deep happiness, the consummation of an unnamed but persistent urge. She was in a trance of hot and inescapable satisfaction.

My hands were on Cally's ass, slowly spreading her cheeks apart and working my slick fingers around the hole. She jumped a little away from me at that moment and I grabbed her hips and pulled them deeper on my cock.

"Ugh," she moaned and complied with my unspoken command.

My slick pinky worked its way around her asshole, then slowly inside. This was not her first rodea and she even relaxed her ass onto my little finger, this was a welcome and expected anal assault. I followed the little finger with my middle finger and worked it a bit deeper into her ass. As my cock fucker her pussy, my finger fucked her ass and I could feel my cock moving inside her, rubbing and pounding its way into her depths. Then it was time for two fingers. . .Cally jumped again and was rewarded with another slam of my cock to the bottom of her cunt.

"Oh fuck, Randall, God, you are a making me crazy," she breathed. "Yes, yes, just fucking do it to me, just fucking do it. . ."

I slipped three fingers into her ass now. She controlled her instinct to jump and began to pump her own pussy against my cock now. Cally was beginning to drive herself into a frenzy of orgasm. She wanted to cum now, she was losing herself to her body, to urges more ancient than consciousness, needs that were chthonic and essential to identity. We had to wear masks to hide from one another day to day, we dared not show our true faces, but here in this Orlando hotel room, drunk, and horny, and beyond the pleasantries of the real world, Cally and I were creatures out of Eden: barely named by God or Adam, pure existence the fulfilled the most basic and the most profound needs. And we were fucking, we were moving together, we were beyond any "no" or any "yes", now we were unstoppable.

As Cally pushed herself beyond rationale awareness again and again onto my cock, I slipped my cock out of her pussy, and slipped three wet fingers in. She moaned but didn't let up her pace. My cock was massive even to my eyes now, rock hard, not angry but redolent of musk -- my own sweat and Cally's cunt juices -- and fully in command. It slipped easily between the cheeks of her ass. Back and forth between her ass cheeks as my fingers fucked her pussy.

Almost gently I moved my cock head against her asshole. Her intake of breath told me she was ready, but she didn't jump. I moved it into her ass.

A sharp in-take of breath, "Ahh, ohhh, okay okay, yes," she mouthed and kept fucking my fingers.

Slowly and inexorable I slipped my cock head into her ass. Cally just grunted and drooled, I could see spittle leak from the corner of her mouth.

"Oh fuck, oh fuck, make me cum, make my cunt fucking cum, fuck!"

Slick from fucking, hard from desire and frustration and disbelief, my cock slid deeper and deeper into Cally's ass. I'd never fucked anyone's ass before, the feeling was weird. . .tight, of course, dirty -- certainly!, very different from a pussy with its muscles and lubrication. I kept moving deeper and deeper into her ass.

"Oh God, mmmmmm, ooohhh, mmmmmm, Randall, oh mmmmmm," Cally threw her head back and moaned with unconcealed pleasure. "Mmmmmm, make me cum, baby, gimme all that cock. . .fuck me so fucking good. . ."

My cock was more than halfway in and my fingers were crooked in Cally's pussy around her G-spot. Her moans were coming in time to when my fingers hit a certain spot inside her. I made sure to run my fingers down that spot regularly. She nodded her head spasming and breathing hard. Meanwhile, my cock was beginning to fuck her ass, not just sliding inside her, but moving in and out now, deeper with every stroke.

"Can you fucking feel it, fuck, you can feel my cum fucking building. . .oh shit," Cally rasped out the words. "Just fucking don't stop. . .do it, fucking do IT!"

Now I was losing myself too. My fingers in her pussy and G-spot; my cock in her ass spreading it wide, beyond what it had ever felt. Suddenly my own balls tightened up with that telltale sign that I was going to cum.

"You're going to get an ass-full of cum, you whore, taking my cock in your asshole," I said. I had no idea where it was coming from but now there was no more talk.

Cally fucked my fingers and I fucked her ass. . .her orgasm arrived her and she yelled out -- a wild shriek of exalted satisfaction. She might have killed a mammoth, scalped an enemy, or defended her child. Her next whoop was into the bedspread and I could feel her gushing onto my fingers, a sacred geyser of her juices and her flavor. That downpour was the last straw for me and I felt my cock tense up and go balls deep into her ass. Then I came -- hard and long and what seemed like forever. Though I'd come less than 30 minutes before it seemed there was even more cum this time. As I came I imagined it filling Cally's ass and it made me buck and cum harder. Hot spurt after spurt.

We collapsed together onto the bed. Spent physically and coming out of an orgasmic trance. The only sound in that room was our breathing that was erratic, and harsh, and sometimes came in huge gulps that fed the worn out muscles we'd pushed to their limits.

As she lay there, I looked at Cally admiringly: the smooth curve of her ass, her muscled legs quivering a little after our exertions, the sweat running down her ribs, her hair wet and smelling of her oils and our fucking. I didn't like her, but I wanted her and realized how attractive she really was. Or how deprived I had been physically for a long time.

Casually I reached for my phone again: I looked at the time -- almost 4 in the morning -- then took another picture of Cally stretched out on my bed. I wanted to remember this moment.

She raised her head a bit, "We're good, right, Randall?" with eyes both confident and pleading.

"Yeah, of course."

"God, my ass is just. . .ow, God, I can't believe you fucked me with your huge cock." She was in pain yet still in the glow of the orgasm. I nodded in understanding.

"Can I. . .use your bathroom, to clean up, Randall?"

I nodded again. "Help yourself."

She pushed herself up off the bed slowly and in a lot of discomfort. Willing her legs over to the bathroom, she half-staggered, half-limped to the door and steadied herself there. Cally looked back for a moment, and said, "Those pictures are just for you, right?"

I nodded, "You kept your word and I'm keeping mine. A bet's a bet."

She smiled and closed the door behind her.

bet's   bet  

Jul 22, 2018 in blowjob

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