Betting on One Night

It was just a simple bet, which is something I can never resist.

"You'll never last an entire night with Jason, so stop looking down there. No girl ever ever has."

Sam and I sat at the bar, him with a cold draft and me with my usual Jack on the rocks. The Rocket was a local place, half a block from my condo and usually filled with good-hearted neighborhood folks, most of whom knew each other. A typical bar. Dark wood, pool table, sports channels on the TVs. A mixed crowd, some married and just chilling, some looking for an evening's hook-up, some who were both. Friendly stuff.

I'd grown up in the neighborhood, and many of the guys had been in the same high school. I'd hooked up with a couple on occasion, including Sam. Nice in the sack, sweet, but not exactly what you'd call a thrill ride.

"What? Is he a perv?" I looked again at the man at the end of the bar. Tall, muscular in a "works with his hands" kind of way, Jason wasn't the stand-offish loner I associated with the guys I'd met who were into kink. Outgoing, Jason had a lot of friends in the area. Male friends. Girls had come on to him many times, but I never saw him with the same woman twice.

I'd never really thought about it until now. I'd come tonight looking for a new hook-up; it had been a long time. When I'd contemplated Jason, Sam had turned sullen.

Sam shrugged and looked away. "Probably not. Maybe he's just bad in bed."

"Yeah, you wish every guy was."

Sam hmphed, and turned to lean his back against the bar. "You wanna catch a movie Saturday?"

"Does it involve a lot of guns and sweaty men?"

Sam grinned. "Probably."

"Count me in."

A pleasant evening. Sam left about 10:30, and most of the others cleared out around 11:00. A few sports buddies, including Jason, clustered around the pool table in the back of the room, cheering on a basketball game from the west coast and occasionally shooting a round of billiards.

Around midnight, I signaled for a fifth Jack. Carter, the bartender, set it down with a concerned look. "You're walkin', tonight, Lyn?"

Carter and I had once spent two glorious weeks in Cancun, diving and exploring reefs and each other. I'd almost wept when he got married. "Of course, hon. I'm just down the street."

He didn't relent. "Sam's right about Jason."

"You got married."

"Just be careful."

"Aren't I always?"

"No." He wandered away to start the closing routine.

Jason's last sports buddies left 15 minutes later, and Jason brought several of the empties to the end of the bar. I grinned at him. "Helping out Carter?"

He smiled, and set the bottles in a neat row on the dark wood. "I used to tend bar. Habits die hard."

"Can I help?"

He shrugged. "Sure."

We made one trip back and forth, then he went to the pool table to get his jacket. I followed, waiting until we were out of Carter's hearing before asking, "Do you mind if I ask you something personal?"

He slipped the leather onto his arms and pulled down the bottom of the jacket. "You want to know why no girl hangs around me for very long." He crossed his arms and looked down at me, his dark eyes almost pinning me in place.

I finally found my spine and stiffened it. "Yes. How did you know?"

His stillness was almost unnerving. "Because I can tell when a girl is watching. When she's interested."

"You think I'm interested?"

"I think if you don't make an effort to find out, it'll make you nuts."

"So are you willing for me to find out?"

"Are you paid up or are you running a tab?"

"A tab."

"Get your coat."

The autumn night's brisk air rushed around us as we left The Rocket, swirling leaves and bits of street debris around our legs as we headed down the street. "I live at 1540."

I knew the building, a fairly new condo renovation. Not cheap. "Nice building. I take it you don't work blue collar anymore. Either you've gone white collar or your secret is a cougar-aged sugar mama."

He grinned. "You know why you have a hard time keeping guys, Lyn?"

"Tell me."

"Your mouth. Smart and smart assed. Most guys don't like it. They like a girl to be dainty and soft-spoken, even if she's smart and a touch feisty."

"They want to think they're smarter."

"Oh, yeah."

"What about you?"

"I like a woman who can challenge me. It makes . . ." His voice trailed off as we reached 1540 and the doorman greeted him by name and opened the glass door. We crossed to the elevator and he pressed the call button.

"It makes what?"

He held his fingers to his lips as we stepped into the elevator and he pressed the button for the fourteenth floor. The silence continued until he pulled out his keys and opened the door to 1414. He held it for me, and I stepped inside. The cool apartment held a scent of musk and leather that enticed, and I stared at the large room with its open arrangement of leather furniture, glass tables, and floor-to-ceiling windows.

"It makes for—"

Jason stepped in front of me and pushed me up against the wall. He grabbed both wrists and snapped them up over my head, where his right hand clenched them both. With his left, he grasped my neck, forcing my head to tilt back.

"It makes the conquering, the punishment, and the relentless fucking so much more gratifying."

His mouth crushed tightly against mine, prying my lips apart as his tongue shoved inside. Arousal flooded through me like a flash fire, and I sucked on his tongue, moaning deep in my throat.

It was as if he'd handed me a match, and I lit the fuse.

His left hand released my throat and grabbed the collar of my blouse. He ripped downward, shredding the cloth. I wore no bra, and his hand closed over my breast, gripping tightly. I pressed my hips against him, and he broke the kiss. "Slut!" he hissed.

"Bastard! You'll never make me cum like this!"

Jason's grin turned wicked, and he grabbed my arm and propelled me toward the long leather couch in the living area. He turned me around and pressed on my shoulders until I bent over the back of the sofa, my ass in the air. Grabbing the waistband of my jeans, he pulled outward, popping the button and splitting the zipper, and he yanked them down.

I tried to push up, but his years as a blue collar worker—bartender, bouncer, construction—had left him with strong shoulders and biceps. At 5 foot nothing and just under 120 pounds, I had no physical leverage over him.

Not that I wanted it. The raw force of his actions had left me hot and aroused—pinning me to the couch was like reading my mind, and the first blow on my ass made me whimper with pleasure.

"I knew it. You're just the slut I knew you were." His hand came down again, the blow echoing around the room. Two more, and my ass grew hotter, my arousal causing my nipples to harden and my juices to flow.

"You like it rough, don't you, slut?"

My voice cracked. "Yes!"

Two more on my ass, then the slaps moved down my thighs and back up again. Fifteen, then twenty. I moaned, rocking up on my tiptoes. He stopped, his hand rubbing my reddened cheeks, then two fingers slid between the lips of my pussy, and he sighed at the moisture he found there.

"My slut wants to be fucked, doesn't she?"

"Yes! Please!"

Two more slaps fell, then I heard his zipper. Still pushing me down over the couch, Jason pressed into me, thrusting his cock in so hard and deep, the pain seemed to split me. I dug my fingers into the cushions of the sofa as he grabbed my ass, the solid thrusts steady, rough, and merciless.

I came with a cry I'd never heard from my own lips before, animalistic and wanton. He came hard, then pulled me off the couch and down on the floor, on top of him. He took my face in his hands, his eyes dark and passionate.

"You want more, don't you?"

I'd never had a man like this, who could make me beg to be fucked and mean it, to want his punishment, more of everything he could offer.

I nodded. "I want more."

* * *

"If you let go of the table, if you close your legs, it's over. I'll put you in a cold shower and send you home. Understand?"

I nodded.

"Say it."

"I understand. Legs open, hands on table."

Jason had stripped me naked and set me on the dining room table, my legs spread as far apart as my hips would allow. He'd then told me to lean back and grab the edges of the table. The idea was to see if I could take what he had to offer without giving up. He slipped a blindfold over my eyes and tugged it into place.

"You can scream if you want to," he said. "No one lives in the surrounding condos right now." He chuckled. "Most girls do scream at this point. In fact, most don't even hang around for the cold shower."

"I'm not most girls."

"We'll see."

The soft touch of leather brushed my right nipple, which hardened immediately. Then the left. Right again, then left, then over one thigh and between my legs. The first slap, when it came, landed with a blazing stripe on my right breast. I groaned in pleasure.

"More?"

I nodded. "More, please."

He obliged, and the crop came down in rapid blows on my tits, thighs, between my legs. My body turned hot, and the stripes on my cunt made me arch and cry out, trying to spread my legs wider instead of slapping them shut.

When he finally paused, I whimpered.

His fingers pushed apart my labia, exploring the tender folds. "Does my slut want to be fucked or spanked?"

"Yes."

He laughed, a low, passionate sound. Two fingers slid inside me, and I groaned. His hand moved in and out, and a third finger slid in, spreading me. "Please," I begged. "I want you."

His thumb pressed down on my clit, rubbing back and forth. "No."

My climax grew closer; he felt it, and his hand moved faster. I moaned, my hips pressing up against him. "Please. I want your cock!"

"No. Don't let go!"

Damn, I'd almost forgotten. I wanted him so much, wanted to grab him and pull him into me, feel his hardened cock buried deep inside. I ached for him. "Fuck me!"

"No." His hand moved in and out now with hard, rough thrusts, and as my climax began, he brought the crop down on my breasts, blows that focused on the nipples.

I screamed, my body rocking with the climax, cumming so hard that my ass arched up off the table and Jason had to drop the crop and grab me so I wouldn't slide off. He pulled me into his arms, laughing and kissing me. He slipped off the blindfold, looking into my eyes. "I want you to cum until you beg me to stop, spank you until you can stand no more."

I wrapped my arms around him. "Won't happen."

His eyes glistened mischievously. "I do like a challenge."

* * *

Twenty minutes later, on all fours in the middle of Jason's bed, I knew that he had some intriguing ways to keep a girl wet and aroused throughout the night. My pussy, wet and swollen, had been coated with a glycerin lube that heated when rubbed, and the silk rope that ran between the lips of my labia had been tied firmly to a belt encircling my diaphragm.

The rope rubbed every time I breathed. Especially when I gasped. And as Jason tried his hairbrush, a ping pong paddle, and a leather strap on my ass and thighs, I gasped a lot.

And came a lot. Twice with the rope before Jason had relented and fucked me from behind, a vibrator in my ass providing the sensation of double penetration. The feel of his cock in me satisfied as nothing else did, only making me want more.

Now he'd reattached the rope, applied more glycerin, and watched me, contemplating his next action.

For me, I felt I'd found my sexual nirvana. Finding men who liked to spank as a part of foreplay had been easy. Finding one who wanted to see my ass red and striped as a basic part of lovemaking had proven more difficult.

With Jason, I was sore and exhausted. My cunt felt raw and abused. I had cum until my head swam, and I only wanted more. THIS was ecstasy.

Jason came to the edge of the bed and reached for a pillow, putting it near my head. "Head down, on the pillow. Legs spread wider." I did as I was told, and he reached for the glycerin again, spreading more on and in me. The heat expanded my arousal, and I breathed deeper, more rapidly.

Spreading me, Jason inserted a vibrator into my pussy, turning it up. Then one in my ass, again on high. The double penetration sent cascading waves of euphoria through me, and I cried out, begging for to be spanked again.

This time, he reached for a flail, the split leather tails knotted at the ends. The blows were gentle at first, then picked up speed and severity as the vibrators and gel did their work. Pain and joy, pleasure and agony blended as Jason's blows fell over my cunt, pushing me harder. I came violently the first time, weaker the second time. I was sobbing by the time my body shook with a third climax, so weak I could no longer stay up on my knees.

"Please. I have to stop."

In an instant, Jason was beside me, taking me in his arms and cuddling me close. He removed the vibrators and wrapped his arms and legs around me, holding me tight, kissing my face, lips, and hair, until I stopped shivering.

Finally, I reached up, stroking his cheek. "Thank you."

He threaded his fingers through my hair, pressing my face against his. "You're remarkable."

"So," I said softly. "What DO you do for a living?"

He laughed, then kissed me. "I'm a pilot. Cargo." He paused and his mischievous grin returned. "Ever been spanked at 30,000 feet?"

* * *

The next morning, we made love. Simply, cautiously, a missionary-style cuddle that held more tenderness and gentle caresses than I'd had with any other man.

I'd made it through the night with Jason. And I knew that there would be many more nights to come.