“So… ‘D’ and ‘D’… dinner and dick again?” Kaitlyn asked her roommate, Haley who was engrossed in her phone and the six dating apps she pivoted between in her daily hunt.
“But for which ‘D’?”
“Honestly… sushi. I’m fishing for any guy willing to take me…,” Haley grumbled.
Down to meet up for a date tonight if it’s GOOD sushi! She wrote to five different men who had bombarded her with super-likes.
Over the last year, Haley had eaten the majority of her meals while on dates. The men thirsted for her twenty-three year old, toned body and sparkling eyes, but she hungered for tapas, oysters, filets, and pho.
Maybe we do coffee tomorrow after work? One man replied.
“Unmatched!” Haley announced while digitally dumping the would-be suitor.
I’m down but I prefer to split the check on a first date. Another posed.
“Gone!” Haley declared, blocking the profile.
What part of town you thinking? Another asked.
“Oooh! Maybe a new contender!” she crowed.
Clement St… maybe Daigo or Wako? She wrote back, specifically asking for her top choices.
A minute went by before the man responded.
Daigo at 7?
Perfect but I don’t do dutch… Haley quickly wrote back then held her breath.
Five minutes went by and the hungry girl began to doubt the man’s potential, so she went back to the business of vetting other men who had sent her super-likes to see if they were game.
Ok, not dutch but this is a date… not friends, k? the man finally wrote back.
“This one has balls! He is fine with not going dutch but was all like… I’m def gonna make a move on you after… what do you think?” Haley asked Kaitlyn, handing her the phone.
The girl swiped through the profile of a man named Noah in Halley’s phone.
“Full body pictures… cute, tall, good dresser… thirty-four… kinda old…,” the girl trailed off.
“Almost no one under thirty is gonna pick up a check at Daigo on a first date,” Haley reasoned.
“His apartment looks clean… nothing weird… that’s a nice coffee table, maybe restoration hardware… it doesn’t look like he has roommates… but he does have a dog! He’s old but I’d go on a date with him,” Kaitlyn decided.
“Would you fuck him?”
“I’d have to see how I feel once I meet him,” the girl pondered. “If he isn’t too thirsty and makes me laugh and if I get a bit drunk… oh and if I think he might have a nice penis… maybe… if I’m horny and not too full.”
“Well then… hello Noah!” Haley said as Kaitlyn handed her phone back
See you outside Diago at 7. she texted back.
Haley quickly showered without washing her hair. She carefully shaved her armpits and touched up the thick strip of sandy brown hair she maintained just above her clitoris, just in case Noah’s potency wasn’t relegated to his credit.
“Oh, I’ve been bald since high school,” Kaitlyn had told her, years ago, when they were first roommates at USF.
“Everyone goes Brazilian and I love to be unique… so I have a nice landing strip when the D approaches this runway!” Halley had laughed. The truth was, she had extremely sensitive skin and every time she took her fur down to the dermis she developed unsightly razor bumps no matter what products she tried. Her sensitivity extended to many products as the poor girl would break out in a rash unless she abided by her tried and true natural soaps and lotions. This temperamentality further extended to contraception to the delight of any man who found himself in bed with the attractive girl.
It was a cool, foggy day and Haley lived in the inner Richmond, near her old campus. That side of the bay was typically hidden from the sun, despite it being June. She put on her favorite Rag and Bone jeans and a top she felt accentuated both her trim waist and respectable bustline. Light make-up, casual jewelery, a few touches to her already done hair, and she was ready to go.
Daigo was more than a few blocks away, so she walked to Geary St and caught the number thirty-eight bus and rode until she was at twenty-fifth street where she walked the remainder to the sushi joint she was dying to try. Had the girl been able to finance her own tour of fine eateries in the bay area, she have gladly done so, and with company she was excited to keep. Student loans from her four years at a private university, coupled with the exorbitant rent and cost of living in San Francisco kept the girl hovering just above the poverty line despite making ninety-thousand dollars a year at a corporate marketing gig she landed with ease.
“I don’t understand how you’re always broke,” her parents complained as they fronted her another month’s rents.
“Ok… I’ll break it down for you! I make ninety, I sock away ten in my retirement, and that leaves me with just under sixty after taxes, or five grand a month. My student loans are fifteen-hundred, my share of the rent is two thousand, my shitty car costs me five hundred a month in just insurance and parking… and I can’t park it on the street… between the asshole meter maids, zooming around writing hundred dollar parking tickets and broken windows from the homeless going after the forty-six cents I had in the ashtray, it’s much cheaper to pay for the parking lot! So that leaves me a thousand per month… or two fifty a week… which is thirty-five bucks a day to live on… and has to be stretched to pay for all my food, toiletries, dry cleaning my freaking work clothes! Toothpaste, tampons, freaking dish soap is a thoughtful purchase! If I go to Starbucks then I can’t afford lunch! If I buy a pair of jeans then I just spent an entire week’s money!”
“Why do you live there if it costs so much!”
“It’s where my damn job is, Mom! Salesforce isn’t hiring in Ohio!”
“Then how come I always see you eating at restaurants on your Instagram account?”
“Uhhh?” Halley stalled.
She knew that her mother would never approve of her dating simply for food, but then again, her mother never understood how difficult things were for Halley, trying to enjoy her youth while being hopelessly mired in debt. When Halley’s mother was her age, she had graduated without a penny in student loans and bought a house before she was twenty-five that was now worth nearly a million dollars. To Halley, the idea of owning a home was as fantastical as flying to Mars with Elon Musk.
In lieu of owning things and being debt free, Halley simply wanted to at least have experiences and her most cherished moments were the savoringly delicious bite of a perfectly seared filet minion, a sweet glaze on seabass, and a silky trailed string of molten chocolate from a spoon dipped into a souffle. In order to experience those morsels, she had discovered a pathway that didn’t require money; dating. And waiting outside of the sushi restaurant was an older man who vaguely resembled the profile she had corresponded with an hour earlier.
“Halley?” the man asked.
“Yes,” she replied, gritting her teeth in anger.
It was evident that Noah was not in his mid-thirties and was probably over forty. The pictures from his profile were definitely the best he had ever taken and were no less than five years old. He even seemed to be a few inches shorter, definitely under six feet, despite his profile emphatically stating otherwise. He also sported a small, but very present, potbelly that was nowhere to be seen in his eight photos that were supposed to serve as a preview to meeting in reality. This was one of Halley’s biggest complaints about the world of online dating; liars. Her pictures were taken within weeks and swapped out regularly. She was exactly as she appeared to be in real life, unlike Noah.
“So you’re thirty-four?” she smiled, brimming with sarcasm.
“Here’s the thing… I’m not… I’m forty-one, but everyone says I still look thirty-four!” the man explained.
“Then why the older pictures?”
“I just like those pictures of me,” he fidgeted.
“Well, I’m twenty-three… just like my profile says and forty-one is out of my age range,” Halley grumbled, despite the fact that she routinely dated men in their forties as long as the venue was sufficiently opulent.
“Oh, well… umm… if you want to go then… I guess…,” Noah stammered.
“No, we’re already here… we can still have our date,” Halley smiled.
I’m going to order so much toro! She said to herself then smiled.
Inside, Halley ordered several pieces of uni, toro, and hotate; her favorites. She insisted on an expensive bottle of wine and, with the tuna and sea urchin, bathing in a hundred dollar bottle of pinot, she began enjoying herself. Despite Noah’s inauspicious start, he became quite interesting after he finished his second glass of wine. Unlike most men, he didn’t dominate the conversation, he didn’t prattle about himself or his job, and, largely, kept the focus on Halley.
“Oh, you’re from Ohio? What brought you to SF?”
“USF is a great school, where did you land after?”
“I think I know some people who work there, how do you like it?”
Most importantly, Noah didn’t flinch when she ordered the market-priced uni and toro, again and again.
“One more round of toro!”
She requested, sounding like a broken record to the waiter.
When the bill came, Halley could see it was well over four-hundred. Barely looking at the check, Noah placed a reflectively beautiful, metal American Express card on top of the small black book. As soon as it was returned, he signed his name to the paper with a flourish and left a handsome tip.
“You wait here and I’ll pull the car around,” he told Halley as she attempted to eat the remainder of the mochi that Noah insisted she try.
Five minutes later, Noah texted her ‘outside’ and Halley left the restaurant and saw him in a pristine, dark blue Mercedes E-class. Without hesitation, she jumped in and began playing with the stereo, enjoying her wine and sushi buzz.
“What do you have in mind to do next?” Noah asked, his eyebrow raised.
“I think you should decide,” Halley smiled.
“I’ve got a few great bottles of wine back at my place we could open?”
“Ok,” Halley agreed while texting Kaitlyn a single character:
The engine grumbled in crisp German as Noah pulled off Clement onto nineteenth avenue and took the tunnel into the Marina then navigated into a luxury building with an automatic garage. A moment later they were in the elevator, then a carpeted hallway, where Noah’s keys opened a lovely one bedroom apartment with pricey furniture and a sunny view of the bay.
“Can you see Alcatraz from your place?” Halley excitedly asked, bobbing her head in the window, trying to figure where the small island should be on the horizon.
“Maybe from one or two floors up,” Noah shrugged while pulling out a bottle of wine from a rack built into his bookcase. “Cartograph Pinot?” he offered.
“Please!” she replied, remembering tasting wine from that particular vineyard a week or two earlier with a corporate lawyer who took her on a date to Portofino’s then fucked her in a dazzling condo at One Rincon.
“Hold on!” Noah pivoted, sparkle in his eye.
A moment later, the man emerged with two glasses and the bottle.
“Carry these!” he commanded.
Then ushered the girl out of the apartment while he carried a plate covered in plastic with a hooded sweatshirt slung over his shoulder.
Halley followed him to the elevator where they went up to the top floor, then Noah made them duck under a heavy chain blocking the last flight inside the stairwell that lead to a heavy door with a sign that loudly proclaimed: Warning! Alarm will sound if opened.
Smiling, Noah pushed the door open and no blaring whistles or sirens screamed in the San Francisco night. As soon as Halley was through the door she found herself on the rooftop and the view was dazzling. She could see all the way to Sausalito. Every building in downtown was lit up and felt incredibly close. Even the stars were out, a treat Halley rarely experienced under the foggy blanket that was her neighborhood all summer.
The roof was clearly not meant to be accessible for anything other than an emergency as there was no rail along the top. If Halley had simply walked a few feet too far she’d step off and land on Scott street far below. The wind whipped past the girl and she was instantly cold.
Fully prepared, Noah quickly walked around the back of the massive bulkhead that was the door downstairs and returned with two plastic lawn chairs. He took the glasses and wine out of Halley’s hands and then offered her the sweatshirt then a seat. The sweatshirt was massive and thick. Halley cuddled herself inside the womb of cotton, not threading her arms through the sleeves but opting to zip herself inside like a sleeping bag.
Noah opened the bottle, poured two very full glasses, then handed one to Halley.
“To the City!” he proudly proclaimed, touching glasses with the smiling girl.
As Halley lifted the plastic sheet over the plate and tasted a marvellous slice of gouda cheese, Noah pulled a small pipe out of his pocket that was already packed with what appeared to be rather choice marijuana.
“Do you smoke?” Noah posed, handing the girl the pipe and a lighter.
“Does the Pope shit in the woods!” Halley cheered, fixing her lips to the end and attempting to light the contents.
The wind whipped over the top of the building, making her task difficult.
“Let me help you,” Noah offered, then taking the girl by the hand, walked her to the bulkhead, away from the wind, and used his hands to create a pocket of still air.
Halley drew deeply and began coughing instantly. Handing the pipe back to Noah, she staggered to the chair in order to fetch her stemware in order to slug down enough wine to calm her rattling chest. When she returned, Noah had completed sucking the smoke and handed her back the pipe.
At first, Halley thought the weed to be rather harsh, but, after a moment, it was silky smooth and tasted divine. Greedily pulling from the pipe a second time, she saw Noah filling her glass. She passed the pipe back and breathed deeply through her nose, filling her lungs with the delicious salty air. Her eyes wavered as they drank in the intoxicatingly spectacular view that was her adopted city. Then she poured another heavy gulp of the wine down her throat.
“Can I throw my glass off the edge?” the stoned girl asked.
“Umm… sure, I guess,” Noah hesitated, not wanted to appear weak in front of the young girl.
The pair walked to the very edge and looked down on the street below.
“Would we survive if we fell?” Halley pondered.
“Nope. Not a chance.”
With her toes at the edge, Halley finished the last drop in her glass, then held the crystal orb straight out.
“No one will ever drink from this glass again… for all time… it was me! I drank from it last!” Halley spoke into the night air then relaxed her fingers.
The rondure container slipped past her fingers then hastily journeyed to the cement sidewalk where it exploded into a thousand tiny shards, echoing off the adjacent buildings.
A moment after, Noah’s glass perilously leapt from his hand to join its brother on the hard surface below.
“Kiss me!” Halley announced, standing on the precipice.
Noah asserted himself, standing with his back to the edge and kissed the girl passionately, not caring that a single step backwards would carry them both to be reunited with their expired goblets.
The danger enthralled Halley. She pushed her hips forward, into Noah who took his right hand and briefly warmed it, clasping the aroused girl’s breast for a moment, before sliding it down the front of her jeans. His fingertips braved the thick mat of hair atop the girl’s vagina before sliding past her wet lips and venturing all the way to the knuckle, deep inside her smoldering womanhood.
“Ugh!” Halley moaned, upon being fingered.
Reaching down, she unbuttoned her pants to give Noah better leverage to penetrate deeper with his fingers. With the additional room to operate, he managed to get a second finger inside causing Halley to reach the critical point where only a penis could possibly satiate her desire.
“Fuck me!” she demanded.
“I have a condom downstairs… let’s go back down,” Noah suggested, plunging his fingers deeper.
“No! Here! Now!” she ordered.
Noah, tried to lead the girl away from the edge but she was intransigently anchored; a horny gargoyle, fixed on the brink. Breaking loose, Noah grabbed the lawn chair and marched it to the edge. There was enough of a lip on the boundary to wedge the feet into. Then, he spun the girl, pulled her jeans and thong to her knees then performed the same action with his own. Stepping over the arm of the flimsy chair, he sat down, his feet dangling precariously over the edge.
“Come on!” he encouraged.
Halley hesitated for a moment, then realized she couldn’t get her leg over the arm to mount Noah with her pants half off. She squatted, removed her clunky shoes, pants and thong, then athletically performed a frightening battement, learned at her favorite barre class, where she elegantly stepped like a ballet dancer over the chair on the edge of the tall building. Guiding her hips, Noah ensured the tip of his erect cock found her slick opening as she dropped onto him.
“AHHH!” she moaned while being penetrated.
The heels of Noah’s shoes touched the edge of the rooftop, but Halley’s sparkling blue toenails danced in the night air with nothing between them and the ten stories below as she pressed her hands into the metal chair to raise and lower herself onto Noah’s cock.
“Yes!” she moaned, feeling spectacularly alive.
The massive hooded sweatshirt impeded her movements. Unzipping the bulky piece of cloth, she attempted to throw it behind her, but the wind caught the great sail, propelling it off the building, twisting and waving as if worn by a ghost in the night air.
“Uh! Uh! Uh!” she panted, uninterested in anything beside her sex. Still, she wasn’t able to orgasm. Riding was never her favorite position and the narrow constraints of the chair convinced her that ecstasy would never be found, bouncing on the older man’s cock with the soles of her feet dangling off the edge of oblivion.
“Fuck me from behind!” she screamed into the air.
Digging his heels into the only inch of hard wood, Noah, showing incredible strength, stood from the chair while holding Halley, and carefully shuffled until he was past the metal apparatus. He placed Halley down and she instinctively gripped the back of the chair and waited for Noah to remove his pants so he could adequately pound her from behind.
With his pants removed, Noah, stepped back into his shoes for leverage, then gripped Halley’s waist with one hand while feeding his cock into her pussy from behind.
“MMMnnn!” Halley moaned, feeling the deeper penetration in her preferred position.
As Noah pounded her from behind, Halley starred into the night air. In a moment of clarity, she thought to herself that this would be one of those moments she would trot out in the future if asked about the most daring place she had ever had sex.
Noah’s hard hand, colliding with her ass, brought her back to reality quickly, and Halley let go of the chair with one hand so as to rub her clitoris with the tips of the other.
“I wish I had my bullet!” she moaned, making due without the powerful vibrating toy.
“I’m gonna cum!” Noah announced.
As soon as the word left his mouth, Halley felt the man begin to back away, as if he intended to pull out.
“Cum in me!” Halley screamed.
“I’m on the pill! Cum in me!”
“HUUU-NAAAHHH!” Noah began grunting.
There was so much going on that Halley couldn’t quite feel Noah cumming but she did feel immensely wetter.
“Don’t pull out! Stay in me til I cum too!” she yelled over the wind.
Noah positioned himself behind the girl, his cock pulsing slower and slower, tiny droplets of semen falling from Halley’s lips as the girl furiously rubbed her clitoris.
“Uhhh… UHHHH!” she began screaming, announcing her orgasm.
Her body twisted as she came and the hand remaining on the chair reached a point of pressure where the uneven force dislodged the feet from being wedged against the wooden border and Halley lurched forward as the chair tripped over the edge of the building.
“AAAAAHH!!” she screamed as her momentum carried her with the chair.
Snatching her by the hip and then, painfully, by the hair, Noah, miraculously, pulled her from the edge and stepped backward with the terrified girl.
“Oh! Oh! Fuck! Oh shit!” Halley panted, sprawled on the tar roof, on top of Noah.
At that precise moment, an eruption of semen evacuated its way out of Halley’s pussy, making a terribly humorous sound causing the girl to laugh.
“Holy shit! How can you laugh!” Noah asked, his heart racing.
“You must have believed I was on the pill… otherwise, you’d have let me fall!” she snickered.
“That’s fuckin’ dark, Halley!”
“Yeah!” she agreed.
The pair stood up and looked over the edge. The chair had fallen and hit a car parked below and shattered the windshield. Several people were looking up to the building and spied the half naked couple.
“Shit! We should get off the roof!” Noah panicked, grabbing his clothes.
“Well, I got off… how do you make the roof cum?”
“I’m going to get thrown out of my building!” Noah worried.
“Well… hopefully they let you go out the door and not get chucked off the roof!”
“Are you done, Halley?” Noah grumbled.
“One more round of toro!” she giggled.
To be continued…
Author’s Note: If you enjoyed this original story, please check out my other original stories in the blog section. Several of the stories have been compiled into full length books.