Sugar's Lucky Hole

This story is part of the Valentine's Day 2019 contest. Be sweet and vote.

I met Olivia Marchand in a coffee shop.

"Excuse me," I said reaching over her at the cream and sugar bar to grab a stirrer. My arm brushed hers as she sprinkled cinnamon onto her cappuccino.

She looked up at me with these unreal royal blue eyes beneath black haired bangs of a bob haircut that skimmed her lovely neck. The tip of her nose and her matte red lips drew me into her beauty. I don't know why she spoke to me. Maybe a bearded, football loving, outdoorsy, beer drinking lug in jeans, a checkered shirt and tie pouring cream into his coffee was a change of pace to this sophisticated-looking five-foot six woman in her late twenties dressed in a pretty green tight-fitting sundress.

Her gaze never left me. As if in a trance, she said, "You have the most amazing blue green eyes."

"Thanks," I replied, glancing away to stir my coffee.

"This may be bold of me, but do you have a girlfriend?"

I'd been on the Tinder-go-round since my last girlfriend and I broke up eight months ago.

"No," I answered, tossing the stirrer in the trash.

"Hmmm," she replied, intrigued by my shyness she mistook for being aloof. "What's your name?"

For a moment, I thought she was setting me up for a robbery, but she was too beautiful to ignore. Settling my gaze upon hers, I was instantly ensnared within those beautiful blue eyes.

"Jordan. Yours?"

"Olivia."

Someone stepped between us and we moved out of their way to a nearby quiet corner where we made a bit of small talk and exchanged numbers before going our separate ways. A day later, I called her, and we went on a movie date to catch a foreign film she wanted to see. When I drove her home, parking in front of her apartment building, we exchanged glances before nervously chuckling.

"I had a good time," she said.

"Me. Too."

Silence.

I murmured, "Well, I guess this is goodnight."

"You want to come in? I cleaned my apartment and changed the sheets. It'd be a shame to waste clean sheets."

Green light! Go boy!

Once inside her small apartment, I settled onto her couch as she fixed me a drink. We chatted and drank, cozying closer to each other before I felt comfortable enough to give her a tender kiss. She returned it with her gentle lips. Our session had begun. Our kisses grew longer and more intense with mashed lips and flicking tongues and before I knew it, I was grinding on top of her with her legs wrapped around my waist until her lips released mine and she breathlessly said, "Let's move into the bedroom."

I got up off her. She stood up and took me by the hand, leading me to her bedroom where a full-size bed took up most of the room. She returned to my arms, answering my hot kisses with an eager, open mouth as my hands roamed over her lithe body. She broke away again to start stripping off her clothes. I did the same and when we stood before each other completely naked, her eyes darted down to my stiff dick standing a full attention. She smiled a lopsided grin. She liked what she saw. The feeling was mutual. Full, tear drop tits with high set nubby nipples in pink quarter sized areolas, a snatched in waist, beautiful toned legs and when she turned to get into bed, she had this sweet ass with cheeks I wanted to slap and grab onto. She was damn near perfect. I crawled into her bed, into her waiting arms, and gave into the thrill of discovering a new female body.

We fucked. The sex: wow. She did this thing where, when I was deep inside her, she ringed the base of my sticky, wet dick with her finger and thumb, squeezing tightly, and held it that way on top of her pussy as I slid in and out of her. Moving in and out of that tight ring felt incredible and I came...hard. I don't care where she learned it or who she practiced it on - as long as she does it with me.

Sometime later, when we were both limp and sloppy wet from orgasms, she rested in the crook of my arm, and happily said, "God, my head hit all four corners."

"What?"

"Well, in my book, if your head hits one corner of the bed, sex is meh. Two corners, it's okay. If I'm face down on a third corner, now we're talking. But four corners is fucking fantastic."

Four days later, when we fucked again, her head hit five corners as we moved clockwise with a corner to spare. When I awoke the next morning with her sleeping beside me, open mouthed and her make-up rubbed off, she looked so sweet and fresh with a smattering of freckles near the bridge of her nose. And when she opened those big blue eyes and grinned a naughty smile before burrowing down into the sheets to take my sex crusted dick into her mouth, I asked myself how did I get so lucky? There's got to be something wrong with her. Something. But for the life of me, I haven't found it. She's smart, funny. She's down for anything. She says she loves my balls; that they fit in her mouth just right. I love how she tongues and bobbles them with her lips until she sucks them into her mouth and looks up all at me all innocent.

Three blissful months later, in the middle of sex, Olivia was sitting naked on top me with my cock all the way up her snatch and my hands on her hips. I pressed my thumb to her dewy clit, rubbed it around and watched her cum. I came soon after, and with jizz oozing between us, I realized I'd never been so exhaustedly happy in my life. Sweaty, huffing and puffing as I cooled down, 'I love you' slipped out of my mouth.

I opened my eyes, hoping she hadn't heard, but she looked down at me, smiled that mischievous grin of hers, and cooed, "I love you too."

She leaned down and kissed me, pushing her tongue onto mine and I moaned as my arms encircled her to slide her body close to mine. I'm in love with Olivia. She's the woman for me. There's just one thing; she's always unavailable on Friday and Saturday nights. See, Olivia is like a mysterious cat that shows up at your house one day, confident, clean and groomed, stays for a few days and then disappears. I know that she's an assistant editor at a food magazine, but when I try to make dates on Friday and Saturday nights, she's always working. I thought she might be a stripper but she's much too classy for that line of work. I asked where she works but she says she's too embarrassed to tell me.

"Maybe one day, I'll invite you to a show."

I figured she sang at the jazz club on Riverside, but I quit asking for an invite. Let her reveal her secret at her own good time. I'm not going to ruin a good thing. We've been dating for seven months and things are going well. We're sleeping together nearly every night; she at my place or I at hers. I took her to meet my parent at Christmas time where she won over my mother with her cooking after downloading a recipe from her online magazine and baking a pie. Then she charmed my father so much that he took me aside in the kitchen and said, "If you don't marry that girl, I will."

Months went by and after ten months of dating, we finally had our first Friday night date on a chilly Valentine's Day night.

Olivia and I met at eight on a busy street corner in the heart of the city. We strolled arm and arm down the busy city street. I'd made plans for the night but so had she.

"Where are we going?" I asked.

"I'm going to take you to my work."

"Really? I was beginning to think you were a hooker."

"You mean a high-class escort."

"A twenty-five thousand dollar per week-end Dubai date book platinum pussy girl."

She giggled and cozied up closer to me. "You know me too well."

Off the main boulevard in the entertainment district, we turned down an alley. A mean-looking, burly Hispanic dude stood by a railing a few yards away. I froze for a second.

"Relax," Olivia cooed, urging me forward. "He's security."

We strolled towards him.

"Good evening, Mateo."

"Hey," he said, before we ventured down a set of dimly lit stairs.

She opened the door to a club I'd never heard of before. There was no sign. No advertising. I don't know if it would even show up on Google maps. We stepped into an entry area lit by red lights where a pretty, older woman with cotton candy blonde hair piled on top of her head and titties pushed up in champagne pink corset stood behind a maître d' stand.

Olivia cheerfully said, "Hi, Sugar."

"Hey, Livie," replied the woman with a husky Southern drawl. Looking me up and down she asked, "Who's the cutie?"

"This is Jordan."

"Ahhh, honey bunny."

Olivia actually blushed and snuggled closer into my arm. "Yes, this is my honey. Make sure he gets a good table up front."

She stood on her tiptoes to kiss my cheek and said, "I have to get dressed for the show. See you in a little while."

She left me in Sugar's capable hands. Stepping carefully in her stiletto shoes, Sugar rounded the stand and led me inside the club. She escorted me into the dark club, leading the way around the small round tables scattered about as we headed towards the stage. I was mesmerized by garters holding up her stockings which hung over her bodacious ass in satin granny panties nearly the color of her skin.

It was a very intimate club. People sat at tables or at the side bar. A band, bathed in murky blue light, played soft jazz in a corner beside the stage. The piano player, drummer and a big bass player looked like they were from the Cotton Club, cool as fuck in cream colored suits and sunglasses.

As Olivia demanded, I was seated a table front and center.

"Enjoy the show," Sugar said before leaving.

I took off my jacket and hung it on the back of the chair before taking a seat. Before too long, a beautiful light skin black girl with long braids wielding a cocktail tray stopped at my table. Her tight curves of her Coke bottle body were on display in a pair of pink velour running shorts and matching jacket she was wearing. She set a cocktail napkin on the table.

"What can I get you?" she asked.

"Got a Dewar's on the rocks."

"Of course. Coming right up."

I couldn't help but check out her bubble butt as she sashayed towards the bar. When she returned with my drink, I reached for my wallet.

"Your drinks are on the house," she said. "Courtesy of Miss Olivia."

"Thanks," I replied, still handing her a five which made her smile in appreciation.

She folded the bill and shoved it in her ample bosom before walking away.

I sipped my drink, looking around at the murky shadows of patrons seated around the club. The band finished a song with a flourish. They received a handful of applause. Then the bass player took out a joint from an inside jacket pocket and licked it before lighting it. He deeply inhaled before passing to a band member. They passed it around a couple of times before stubbing it out. Then they began to play and upbeat tune.

A spotlight hit the stage and I shifted getting comfortable as I turned my gaze towards the stage. My eyes widened and my mouth nearly fell open as Olivia, dressed in a black corset, black satin bikini string panties, fishnet stockings, and black stiletto heels, slinked onto the stage wielding a riding crop. She grabbed the microphone from the stand.

"Welcome, one and all, to Sugar's Lucky Hole."

Applause sprung from the crowd. Then she began to belt out a song like a Broadway pro.

'Welcome to Sugar's Lucky Hole. We're going to show you some things you ain't seen before.'

A set of topless twin girls in black sequin tap pants like 1920's girls enthusiastically trotted out to flank Olivia on stage. Their small titties jiggled as they did their synchronized dance.

'We'll make your moan with our bump and grind. We're going to tease you and please you with our cute behinds.'

The twins turned around and stuck out their butts. She tapped each one with a swat of their riding crop which made them hop with open mouth shocked faces. Olivia moved with grace as she did a little high energy showgirl dance between the twins.

So let's start the party, let's get it on, in Sugar's Lucky Hoooole!

The spotlight dimmed as she and the girls strutted off the stage before the stage went dark and I proudly clapped along with the others.

The club and acts are best described as a risqué cabaret burlesque. It was a blend of music, old acts like a fan dancer and acts from modern times. My waitress went up on stage and grabbed the mic. The bass player plucked out a beat as she gave a spoken word tribute to her punani. It was accompanied intimate interpretive dance by a couple; a guy in a loin cloth and a girl in a suede bikini which matched the color of her skin touching, embracing, and rubbing against each other as the poet uttered an ode to her pussy.

'My punani is goddess mother; deliverer of life. A pleasure, a weapon, a muscle of delight. You make it soooo juicy, moist enough to eat. You know it's your favorite San Francisco treat. Sooo sensual, sooo smooth, put it in, let me soothe your aching hard cock that brings me such joy.'

The dancers ended up on the floor, the man on top of her, simulating sex. Was it a simulation? I wasn't sure. They looked like they were really doing it.

'Velvet walls that squeeze, massage you until you shoot your load and we merge in our juices of love making.'

The acts become more outrageous as the night went on. Then came the act that made my mouth drop open in pure shock. The bass player started plucking at a three string Japanese guitar. Very peaceful and precise before the curtains opened. Then the spotlight popped on to reveal the crazy sight center stage.

A Japanese woman, wearing a red kimono hung suspended by ropes, her knees splayed open as though she were sitting in a rope chair. Her face was painted white with kabuki make-up and she wore a black geisha wig with intricate twists and knots. A wizened old Asian man shuffled onto the stage. For some reason, I believe he's the one who tied her up there. He flung open her kimono to reveal his handiwork of tied knots holding up her naked body. But the reason my mouth fell open is that the pink of her pussy was absolutely exposed. And a flower, a lily, was sticking out of her pussy. A skinny, near girl with long dyed red hair crawled onto the stage towards the suspended woman and stopped to raise up on her knees. Her head was in the bound woman's snatch where she took the flower by the teeth and pulled it. To my surprise, another flower popped out of her pussy as part of a daisy chain and the girl proceeded to crawl off stage, exposing another flower and another. How flowers were up her? The daisy chain of flowers stretched fifteen feet before the last one popped out to be dragged off stage where the crawling girl disappeared, leaving the bound girl and the trail of wet flowers.. The curtain closed. Everyone applauded, as did I, slowly shaking my head.

On the dark stage, a girl walked onto the stage with a chair, setting it in the middle facing the crowd before walking off the stage. A pink spotlight appeared and a few seconds later, a girl took the stage dressed in a short pink satin robe. It was Olivia. I almost didn't recognize her under the long pale pink wig, long black lashes, pink glossy lips and a little black heart drawn below the corner of her eye. She looked like a My Little Pony had come to life, became a woman and worked at a futuristic Japanese sex club. She stood there like a confident pixie in Lucite heels holding her microphone.

She said, "As you know, it's Valentine's Day and I'm proud to say my lover is here. I love you, baby."

I puckered my lips to give her an air kiss.

She continued. "If you will indulge me, I'd like to do something special for him. Honey? If you'll join me on the stage, please?"

Embarrassed, I hesitated, feeling my cheeks flush but she smiled at me and that's all it took. I rose from my seat, a bit uncomfortable by my half-hard dick and mounted the two steps to the stage. Olivia placed her microphone onto a mic stand. She took my hand and sat me in the chair. Blinded by the spotlight, I couldn't see the audience. I began to get nervous. The band started to play the sultry beats of a rumba and Olivia, facing the audience swayed to the beat.

The piano player began to sing Sign Your Name Across My Heart and I began to fall under the spell of Olivia's slow swaying hips. She strutted around my chair to the sultry beat, her delicate hand trailing around my shoulders, until she stood before me once more. Facing the audience, she slowly untied the sash holding her robe and let it drop to the floor. She slowly shrugged the robe from her bare shoulders until it hit the floor as well. My eyes widened to see her lovely butt cheeks in a string thong mere feet from my face. I felt like a hungry lion in the grass watching a gazelle. I just wanted to pounce and bite on her ass. Still swaying, she extended her graceful arms as her long pink hair hung down her naked back. Was the crowd getting a good look at my girl's tits? Then she turned around and I sucked in air as I saw diamond pasties covering the nipples of her upturned breasts. She danced for me and I wanted to grab her but I'd been in strip club's where touching the girl is a no-no so I made a conscious efforts to keep my hands by my sides.

She turned around once more to sit on my lap where she began grind her cheeks against my groin. She looked over her shoulder and murmured, "You can touch me if you want."

My hands went to her waist, creeping around her stomach and up to her titties that fit so perfectly in my hands. I played with them, giving no thought to who was watching, as she writhed on my lap. I was totally hard in my now moist tidy whities. My hands drifted down her oiled skin to settle on her flexing thighs as she undulated the cavity between her ass and legs over my burgeoning hard-on. She dismounted to turn around to face me, straddling my thighs to settle upon me once more. She looked deep into my eyes before flinging her body back as the song ended with a high hat crescendo.

The audience applauded and she righted herself to face me.

"You okay?" she asked.

"Yeah," I hoarsely replied.

She got off and led me off the stage. The twins, now painted blue and green and clad only in matching panties, scurried past us to wait behind the wing curtain for the band to play them on. Olivia led me through the narrow, dark hall to her tiny dressing room, where she closed the door behind us.

Olivia asked, "So, what did you think?"

"You almost made me cum in my pants," I said looking down at the small dark spot of pre-cum on wetting my pants.

She giggled. "Sorry."

I walked her back to her dressing table. "I wanna fuck you right now."

"Baby, I have to close the show."

Kissing her, I murmured in her ear, "It won't take long."

I whipped her around and bent her over the table, running my hand down in the crease of her cheeks. I dry humped her, getting harder with each thrust. Bottles tipped over and rolled off her table. Her bag fell to the floor. Her hands flew back to push and swat at me.

"No. Stop. I have to get back on stage."

She pushed at my thighs, slapping at them really until I released her. She turned to gaze at me with horny eyes.

"Later," she said. "Go back to your table. Take the first right when you leave the room."

"You going to blow me later?"

"Yes, yes, I'll suck your dick. Now go. Out. Now."

She opened the door and pushed me out before slamming it shut . I stood there a while, until my dick settled down again, before finding my way back to my chair. I caught the last of the twin's act where they showed off their contortion skills that were so good, they could work at Cirque de Soleil. They left the stage and the curtain opened to reveal a pretty brunette girl bound to plywood wall. From her collarbone to her legs, she was covered with a sheet which hung on either side of her tethered by tabs attached to the plywood wall. On the other side of the stage, five stout red candles burned on tray perched on a wooden table. Beside the candles were three hatchets and a coiled bull whip. An athletic redheaded woman, with a sleeve tattoo and black leather biker pants and vest, sauntered onto the stage. She picked up the hatchets, walked across the stage from the bound woman, turned, aimed, and threw the hatchet towards the bound woman. The hatchet hit the wall with a thud, cutting through the first tab which caused the sheet to fall which revealed the bound girl's left breast. The crowd clapped. She threw the second one, cutting the other tab, and the sheet fell to the ground exposing the naked girl. Lovely and slim, you could see the naked ribs as she breathed. Then the leather chick picked up a bull whip. She wriggled the whip on the floor before snapping it in the air with a deafening crack. She swung the whip over her head and with a quick flick, she cracked it forward the candles to extinguish one. She extinguished them all except for one. I clapped with the others as she walked over to pick up the last lit candle. Then she walked over to the bound girl and proceeded to drip wax over the hapless girls' breasts. I'm ashamed to say it turned me on to see the brunette flinch as she bore manageable pain. Her tormentor lowered the candle and kissed the bound girl fully on the mouth. They were both into it when the curtain closed.