Halley needed to change up her dating profiles again; new pictures, new description, new Halley. She had gotten super-liked by several men whom she had allowed to take her on numerous expensive dates, after which she swiftly ghosted them. The aggravated fellows, upon noticing the beguiling former companion’s profile had once again appeared on their phone, spent a little more of their hard earned money to super-like her, again, to ensure the Halley would be forced to remember they had already been acquainted. By accident, Halley had mutually swiped one of them only to be greeted with an angry tirade.
Hey! Remember me? I took you to dinner… five times… you said you wanted to go slow so we could get to know each other… then you ghosted me when I balked at getting a reservation at Gary Danko for date #6 BECAUSE I STILL DIDN’T KNOW YOUR LAST NAME AND WE NEVER EVEN KISSED!!! Well… you’re a fucking gold-digging bitch! I spent $1382 on five dates… I want half of that back!
“Asshole! Blocked and reported!” she cursed.
“Maybe a name change… you could be… Natasha?” Kaitlyn offered, making a fun show of the possible pseudonym, as if her roommate could be the love interest of a British secret agent.
“I just need a better way to not see any repeats…,” Halley puzzled.
“Ugh! That sounds like so much work… I just want to eat at Gary Danko!” she wailed.
“Nah… I’ve done all of that a few times… I just need to switch age ranges for a bit and let the pool naturally filter itself,” Halley concluded.
“So… younger?” Kaitlyn pryed.
“No! Younger guys are broke as fuck… older. Gotta be older,” she concluded.
“How much older?”
“No one under forty… nope… forty-five,” she decided.
“Older than forty-five! Ewwww!” Kaitlyn retched.
“I’m not going to sleep with them… just let them take me to Gary Danko. But I might sleep with a fifty-year-old for French Laundry… or dinner on a private jet… on our way somewhere expensive!”
“So how are you going to do this… magic act?”
“Just like this…,” she replied and began typing her new description in the dating app:
Office over Friends…
SF over NYC…
Head over heels…
Dazzle me with your knowledge of fine dining and you have my attention, take me to Gary Danko and I’m yours!
“Now… let’s search in the area for old dudes!”
Halley set her age range at forty-five to fifty-five and began swiping on older men who dressed immaculately and had pictures of themselves in foreign sports cars, private planes, and on fabulous vacations. It wasn’t long before she had a dozen attempting to converse with her.
“That was quick!” Kaitlyn blurted, surprised.
“Oh when you’re fishing with a twenty-three year old worm, the old fish bite quick!”
After some trial and error, she settled on a silver-haired fox named Gerald whose profile had him skiing in Gstaad, driving up the coast in an Aston Martin, and shaking hands with Gavin Newsome.
We can go to GD if that’s what you like, the man wrote in the app.
Yessss! She replied.
How about tomorrow night at 7? He offered.
Umm… yes! How can you get a res so quick? She inquired.
Oh, I have my ways. Pick you up first? What’s your address?
I’ll meet you there.
Sorry, I’m old school and I pick up my dates.
Halley waited, yet the man didn’t buckle under the silence and she finally gave in and offered an address down the block to meet the gentleman caller.
The following night, Halley wore an elegant but understated dress, her favorite heels, and even spent the time to use the iron to doll her hair up with ringlets. Exactly on time, the Aston Martin from the profile growled down Anza Street with the silver haired man inside wearing a stylish suit. The man hopped out of the car, walked around the other side, and opened the door for Halley.
“Good evening, Halley, you look simply lovely!” he smiled.
“And you look very dashing, Gerald!” she replied.
“Please… call me Jerry. Only my friends call me Gerald and we’re going to be far more than friends,” he winked.
The pair drove to Hyde Street and handed the car over to the valet. True to his word, they had a reservation and Halley selected the tasting menu with the wine pairing. Everything was divine and couldn’t have been more expertly prepared.
“Thank you! That was so wonderful!” she beamed, after finishing her final bite.
“And for dessert, I thought we’d grab a suite at the Saint Regis and see if I can make you sing the high notes,” Jerry grinned.
“Oh! Oh… um… that’s a little fast for me… I don’t think so, Jerry,” Halley frowned.
“Well… it’s always worth it to ask,” Jerry smiled, then flashed two fingers at the waiter who brought over two small black booklets and placed one in front of Jerry and the other at Halley’s place.
Opening the book, Halley saw that she was presented with a bill for her tasting menu, her wine pairing, her pre-dinner cocktail, and twenty-one percent mandatory tip, which included the healthcare tax for the restaurant employees, which, brought her tab up to three-hundred-fourteen-dollars and change.
“What… what is this?”
“It looks like your half of the bill, dear,” Jerry calmly replied.
“Uhh… uh… I thought you were a gentleman… I mean… am I expected to pay on our date?” Halley seethed.
“Oh, sweetheart, a gentleman and a fool are two entirely different things. Besides, you’re not paying for our date, you’re paying for your half. I’m paying for my half,” Jerry smiled, placing his black American Express card into the book and handing it to the waiter who impatiently hovered over Halley.
“Would you be needing anything else, miss?” he asked, with a slightly impertinent tone.
“One moment please,” she breathed at the waiter.
“I’m not paying this!” she rose her voice to Jerry.
“I’ve got no idea why you’re saying this to me… I don’t own the restaurant you just ate at. Have a lovely evening,” Jerry winked then began to rise from the table.
“Wait!” Halley whispered.
“Pay for me. You tricked me and now you’re stranding me,” Halley seethed.
“No, no, no, no, no… you tried to trick me and now you’re caught. I’m sure you bat your eyelashes at younger men and tell them you want to go here or there… then, after they pay, you wish them a swell evening. It’s not going to work on me. Pay your tab and go home, Halley,” she lectured the girl.
“Pay for me but I won’t go to the hotel with you… but I’ll do something else,” she whispered.
“Oh, we’re negotiating now… what will you do?”
“Well… I absolutely won’t fuck you for a three hundred dollar restaurant tab… I won’t suck your cock either. In fact, I wouldn’t fuck or suck you for ten-thousand! I can pay this tab but I’m willing to see what you’ll offer. So, what do you want?”
“I want you to watch me jerk off in my car… and when I’m doing it, I want you to encourage me. Then, when I cum, I’m going to finish in a handkerchief and then I’m going to give it to you, and you’ll put it in the crotch of your panties and wear it until I drop you off at home, ok?”
“Are you… are you fucking high?”
“I assure you, I will be if you do this for me,” he calmly stated.
“That’s the most bizarre thing I’ve ever heard… and you’ll do this, completely on your own? You’re not going to demand I jerk you off or any bullshit?”
“Yup… you just gotta watch, no looking away.”
“Fine, pay the tab and let’s do this!” Halley demanded.
“Not so fast. I’m going to give the host three hundred dollars and your driver’s license in an envelope, you can pick it up tomorrow and pay your tab then.”
“The tab was three-hundred and forty… and I’ll need an uber to get here.”
“Three-forty then… you can walk off some of the calories you ate,” he chuckled. “Now, give me your driver’s license.”
Halley regretfully handed over her driver’s license. Jerry took the card and several crisp hundred dollar bills, along with a few twenties, and handed them to the host who, miraculously, had an envelope ready.
“Halley can pick this up tomorrow to pay her tab, ok?”
“Of course,” the man smiled and used a pen to write Halley’s name on the envelope.
Jerry walked with Halley out of the door just as the valet was dropping the car off. As before, Jerry held the door open for the much less enthusiastic woman who was born when he was in his early thirties.
Leaving the busy area that was Fisherman’s wharf, Jerry drove a couple blocks away from Halley’s supposed apartment location and found a secluded spot near an unlit alley. He pulled over, turned off the engine, and cut the lights.
“Yeah… jerk off for me, old man!” she demanded.
“I said encourage me,” Jerry chided.
“Well… this is how I encourage. I’m the Bill freaking Parcels of making you bust a nut… now stroke that skinny dick old man! Let’s see if you can jizz for this twenty-three year old! She doesn’t have all night!”
“Very well,” he replied and unzipped his pants and carefully extracted his penis.
“Holy fucking shit!” Halley blurted, shocked that the old man had such an incredibly massive cock. It was at least eight inches long and grotesquely thick. The shaft almost looked misshapen with bulging veins and pale spots followed by darker regions. Most surprisingly was the head. It was incredibly ugly but a massive bulb that looked like one of the huge genetically engineered, misshapen strawberries that men sometimes sold along the roadside.
“That’s fuckin’ way bigger than I thought it would be!” she blurted. “Can I touch it?”
“No, you get to watch and that’s it… but if you want, I need some lube… so you could spit on it, if you’d like?”
“Yeah!” Halley agreed then got close and swished saliva in her mouth until she had a good amount then drooled the stringy liquid onto the old man’s cock.
“Spit in my mouth!” the old man added.
Hocking deep in her throat, Halley spit a tightly formed ball of saliva into the old man’s open mouth.
“You’re a freak!” she smiled.
With the massive wad of spit, Jerry began to massage his cock while Halley sat, cross-legged, watching, mesmerized. With his other hand he pulled out a beautiful, embroidered handkerchief that looked to be make of silk.
“Let me see your balls,” she asked.
Jerry pulled a massive scrotum out of his pants that contained two hulking testicles that were also grossly misshapen.
“This is what I’d imagine Shrek’s dick to look like!” Halley squealed.
Using his hairy fingers, Jerry squeezed as his hand rose up and down the misshapen cock. The veins bulged and the massive head contorted, morphing the shape depending on the progress of the stroke.
Unable to look away at the breathtakingly disgusting penis that belonged to a bizarre old man, Halley whispered her encouragements from the passenger seat of the parked car.
“I can’t wait to see it happen… cum for me… shoot your load… I want to see it!” the young girl prayed aloud.
“Do you… you want to see it?” the man grumbled while stroking.
“Yes!” the girl hissed, her eyes ablaze.
“What will you do with it? What will you do with the cum?”
“It’s mine! I’m going to take it with me!”
“How?” the man grunted, his strokes increasing in speed.
“You’re going to cum on that piece of silk in your hands and I’m going to slip it into my thong and wear it home… I might even sleep with it!” she breathed.
“Oh! Oh yes!” Jerry grumbled, furrowing his brow and positioning the handkerchief above the now throbbing carmine strawberry.
“Yes, Jerry! Cum for me!” Halley begged.
“RRRRR!! HAAAA!” the old man screamed as a torrent of glue launched from the bulbous head and splattered all over the silken handkerchief, dangling over the erupting mount Krakatoa.
“Ohh!” Halley squealed at the massive ejaculation.
“RRRRR! RRR! RRR!” Jerry sputtered as additional globs smacked into the delicate fibers.
The sputtering cock stopped twitching and Jerry carefully began dabbing the glazed tip with clean stretches of the handkerchief.
“Take down your panties,” Jerry commanded.
“Thong… I haven’t called them panties since I was a child,” Halley joked while reaching up the sides of her tight fitting skirt to slide down her black thong.
“Do you want to or may I?” Jerry offered, holding the folded, cum drenched patch of material.
“You can,” Halley smiled with her thong tightly around her thighs causing the stretching material to dig into her flesh like a dressed up ham.
Slowly and carefully, Jerry turned the handkerchief so that the semen covered side was angled in the direction of the young, furry vagina belonging to the girl in the passenger seat.
“Are you ready?” Jerry asked, giving the girl one last chance to back out.
Instead, Halley carefully spread her labia with two fingers and looked at Jerry, goading the man to continue.
With a knowing grin, Jerry adjusted his precarious grip on the material to angle the most pregnant bead of semen at the tiny wet fold of Halley’s parted lips. The silk came in for a landing perfectly and stuck to the delicate pink flesh of the young girl.
“Oh!” Halley gasped.
Smiling, the girl pulled up her thong, holding the silk in place, then shimmied her skirt back under her hips.
“Can I drop you off at your actual address?” Jerry asked, returning the massive deformed penis into his slacks. .
“Only if you pick me up there again… and soon,” Halley smirked.
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.