A Randy Retirement Pt. 08: Anya

Intro: The exploits of a man whose given name fit him perfectly, Randy, and he certainly was that. He was a high-school history teacher and coach until he hit the lottery and retired early at 52. While he was not averse to returning flirtatious quips from the girls in his classes, he did avoid giving in to the urge, telling the more enticing of them to, "come see me after you graduate." Some did, but these stories deal with his life after hitting it big and building two houses; one along a river bluff 45 miles inland from the Atlantic Ocean and another on a secluded portion of the Northern Outer Banks, both equipped with playrooms. And he still had over a hundred million to spare. All characters are 18+ years of age. All stories can stand alone, but reading the series gives added insights and descriptions as it unfolds.

Synopsis: High-class call girl finds she will fuck fossils for free.

September, 2016 - OBX house

After Halley had left to go to college out of state (previous story), Randy decided to spend the final weeks of August at the house he had built on the northern Outer Banks through the long weekend of Labor Day. It was a good place to think and he could spend the days with only the interruptions he allowed.

He knew he was going to miss her and thought that with her being off to college the unique relationship between them would probably fade away. If that were the way it turned out, he could deal with it, but it would not mean that he wouldn't miss their time together, and the fucking. It also meant that he had to process the change in his life and that was what the time on the OBX was about.

As he progressed along on the three-hour ride the houses became sparser on the mainland, especially the last 35-mile stretch of two-lane road with the deep canal running alongside it that was home to the occasional alligator. He smiled as he thought of one of his occasional ways to spend a day, watching from his house as families looked for sand dollars, seashells, and shark's teeth on the isolated beach. The endless search for fossils.

He crossed the bridge from Roanoke Island to the barrier islands and turned left for the last 45 minutes of his drive and called ahead to a favorite pizza joint to order a meatball sub for take-out.

His SUV parked in the gravel lot, he entered the establishment in his usual island dress; cargo shorts and a t-shirt with a sweat-stained baseball cap. When he was here, he usually dressed like a local except for the rare special occasion. Most of the time when he was out on the island he appeared as a common laborer or fisherman, unless of course one checked his hands. Still, there were very few of the locals who associated him with money, except maybe the waitresses he tipped generously.

Greeting the septuagenarian behind the bar, he sat down and ordered a soft drink in a to-go cup and asked for his order. Sam, the bartender, brought him his drink and asked, "Back for a spell?"

"Yeah, probably about a month. Anything new afoot?"

"Just her," and Sam's eyes pointed to someone seated at one of the tables to Randy's left while his head remained still. Turning to see what the wise old man meant, Randy took in an extremely fit young woman with hair that was just browner than auburn and wearing a tight white mini-dress. She rose from her chair to leave and her lithe body moved every inch of the white fabric of the dress as she walked toward the door. Turning back to Sam he shared his initial observations, "She knows how to move Sam, but there isn't any softness in that body, it's rock hard," and he noticed that Sam was not listening, still intent on watching her as she sashayed out the door.

Leaning to his left to put himself into the old man's vision, he inquired, "Who's the lady Sam?"

"Ahh, she blew in her from New York first o'da week. Been in here couple of times already. Says she's here on vacation." Sam had lingered on the first word of that last sentence as he wiped down the bar and Randy caught the skepticism.

"Well, she certainly fills that dress out nicely."

"Too expensive."

"The dress?"

"No. Her," and Sam nodded his head toward the door she had exited.

"Aren't they all?"

"Different kind of expensive," Sam replied, and Randy read his mind.

"How do you know that Sam?"

The full head of snow-white hair looked down as he continued to wipe the bar, slightly embarrassed. "Well," and he paused and then he lip-pointed to his right, "she sat right there at the end of the bar the second time she come in here. Heard her on the phone a'tellin' somebody she wouldn't be takin' no appointments 'til after Labor Day; that if any clients needed her," and the bartender looked back to Randy, "that they needed to find another whore, that she didn't think she'd have a problem getting them back when she returned."

"Well then, I guess it's a good thing I usually don't pick up strangers, you never know do you? But then, I guess we all get by as best we can," Randy smiled as he paid and picked up his food. "Thanks Sam. Don't be too hard on her, she's a good lookin' gal; she might just fuck ya." and he walked away as a grinning Sam picked up the twenty-dollar bill from the bar.

Randy drove into the garage of the home he had built on one of the few isolated stretches of the NOBX. The house was essentially a square with round sections built into the southeast and northwest corners. The east side faced the Atlantic Ocean and the circular section there was the living room. It's twin on the opposite corner held two guestrooms and a shared bath.

Attached to the other two corners of the square were smaller rectangles; a playroom on the northeast side and the two-car garage on the southwest side. The other stall of the garage held a 25-year-old pickup truck that he often drove around the island. The playroom here was about a third of the size of the one at his River house and could only be accessed from his bedroom. A deck wrapped around the southern and eastern sides of the house with a pool, hot tub and gazebo facing the ocean.

He checked the house and then ate his supper at the kitchen bar before bringing his stuff in from the garage. Afterward he sat at the small round table under the gazebo outside and the brunette came briefly to his mind. She had worn one of those black lace chokers. Sometimes a female did that as a fashion statement. Sometimes one would do it to denote that they were submissive. He chuckled as he thought to himself, 'Too bad that I'll never find out." His mind then turned to Halley and he smoked and watched the moon as it rose until it rotated out of sight well after midnight.

*

Randy was planning on the solitude of last night to continue for the next few weeks. He was in no mood to cook every meal however and ventured out to a variety of restaurants where he was known by sight. Sometimes he dined in, sometimes he got take-out. Despite the solitude, deep down he knew that he needed something to break the morose attitude he was experiencing.

Over the course of the next week and a half he noticed the well-toned woman in the white mini several more times at various establishments during lunch or dinner and she was always dressed provocatively. One night they were seated three tables away from each other at a popular upscale restaurant in Kill Devil Hills; one of the few places for which he would dress up. She was in a red, ankle-length, sequined gown that was split to her hip and revealing a shapely thigh as she ate broiled shrimp and scallops.

The last time he had encountered her, she was wearing a purple micro-bikini and a see-thru, white cover-up on the Wednesday prior to the Labor Day holiday in the grocery store and causing much consternation for the teenaged bag-boys there. Each time she had been wearing the black lace choker, as she was now in the check-out line.

Her overt sensuality did not go unnoticed, despite his neutral attitude about her. She was a trim and tight 5'4" and just over 100 pounds with a proportioned body that was in his estimation about a 32B-24-34.

'She knows how to use it,' Randy thought as he watched her at the register ahead of him, 'Well, she is a professional; she should,' and he noticed, as she paid with cash, a quick glance his way which he returned with a smile. She smiled back, took her change, and departed.

That Friday night he had returned to the pizza/bar that was about 20 minutes from his place. He had waved at Sam behind the bar and sat at his usual table that had a view of the entire room and ordered a pizza. Just as the waitress brought out his food, the brunette strutted in and turned every head in a royal blue mini-dress and 5-strap stripper heels. She glanced to her right and took him in briefly on her way to the bar and sat on one of the stools.

Randy thanked the waitress and began his supper as the brunette monopolized Sam at the bar for ten minutes before standing and heading toward an empty table with a glass of red wine in her hand. His napkin slipped from his knee to the floor and he bent to retrieve it. When he straightened, she was standing at his small table.

"Would you mind if I joined you?"

His mouth was full, so he nodded to empty seat on his left and quickly swallowed as she sat. "Would you like a slice?" and she said she would and thanked him. Randy called the young waitress for an empty plate and as they waited, he introduced himself.

"I'm Randy by the way, seen you around a few times I think."

"Anya," she said as she held her manicured hand with blue polish to match her dress out. They shook and she continued, "I've noticed you a few times as well. Do you live here?"

The spare plate arrived, and Randy placed a slice on it for her with the spatula, "I live here off and on. Depends on my mood. Are you here on vacation?"

She replied with what he already knew, and the conversation turned to her love of the beauty of the place and the solitude it provided. She was being mildly flirtatious without being overt and they began to laugh as he confirmed or debunked her observations of the island.

As they came to the last slices of the pizza, Anya drew a deep sigh, "Randy, I'm afraid I have a confession to make. I asked Sam if it would be alright for me to come over and he told me it was a free country."

Randy chuckled and wiped his mouth with the napkin and turned to face her, "Sam is an acquired taste. That all you asked him?"

"Pretty much. I only asked because I'd seen you those times in the past two weeks and here you were again tonight. I don't know, I guess I was curious."

"I see," and he contemplated the pizza slice in his hand a moment, took a bite, and looked to her as he chewed, "What were you curious about?"

Anya shrugged as she looked off into nothingness, "About why you were always alone," and she then focused her gaze back on him.

Randy stalled and looked to the table and his near-empty glass. She asked him if she had overstepped, "No Anya, your question was fine. I just didn't expect it. Excuse me a moment, but hold that thought and I'll be right back," and he picked up the red plastic glass and headed to the bar for a refill.

"Refill Sam and another wine for the lady."

When the full glass was returned, Sam inquired, "I see you've acquired some company."

"Seems like. She ask you anything about me when she came in?"

"Yeah, she wanted to know how old you were and if I thought you'd mind her asking to sit with you. I told her that was her choice, it's a free country," and he placed another glass of the red on the bar.

"That all?"

"Yep."

"Thanks Sam," and he took the glasses and returned to the table.

Sitting the wine alongside her almost empty glass he said, "My apologies for not inquiring if you wanted another, so I just got you one anyway," and she thanked him as he continued, "Now, where were we? Ah, yes, my apologies also for the delay. Why am I always alone? Well, it's rather simple Anya, I choose to be alone."

"Interesting choice, but one I can certainly appreciate," and she changed tactics, "If I might be so bold, what do you do for a living?"

"Live," and she smiled with a hint of frustration. This was not going as smoothly as she had imagined. "Nah, I'm just being a smartass. I'm retired. I was a high school teacher. How 'bout you, Anya? What do you do in the big city?"

"Oh, I have a small little business. It's a busy place. Lots of stuff going on. There is so much tension and stress in everyday life for many executives up there and I provide them a service to relieve some of it," she coyly answered as she placed a lacquer-nailed hand on his thigh under the table.

Randy didn't flinch or react in any way. If you had been watching them you would never have known that her hand was mid-thigh on his leg as he calmly address the situation, "Anya, you are a very lovely woman and I'm sure you are excellent at what you do and have 'em lined up back in New York, but," and he looked dead into her eyes, "I don't pay for sex."

Without batting an eye, she slid her hand closer to his crotch and retorted with a smile, "And I don't fuck fossils for free."

Randy laughed and placed his hand on hers to stop its slide, "You sweet little girl, you stole that line and don't even know it. It's from a 1980s movie titled 'Hardbodies'."

"Really?" and she was serious.

He brought her hand back above the table and clasp it in his own, holding it up and kissing it lightly. She hid well the slightest hint of embarrassment in her eyes.

"Yes really. It was a B-movie about three 50-somethings on vacation at the beach and they pay a 20-something guy to show them how to pick up 20-something girls. Stereotypes out the ass and mildly funny. There was even a song with that line as the theme. You should watch it sometime, just for laughs. Now tell me, what prompted you to proposition me just now?"

Their hands still clasped, but now on the table, she looked down at them and quietly, but defiantly asked him, "Are you looking down your nose at me? Because I can just get up and leave right now."

Squeezing her hand tighter, he smiled at her. "No, no Anya. I'm certainly not judging you. I just don't make a habit out of picking up or for that matter, being picked up by, women that I do not know. It's kinda like a habit of mine. I like to have some idea of a person's motivation, that's all."

She took a sip of her wine and let it wallow in her mouth before swallowing, the black lace choker moving as she did so, and then looked at him, "I've been here for almost three weeks and," she paused and then plowed on, "I'm horny. I thought maybe it would be a way to make a little spending cash. Since I'm on vacation and you were just a retired teacher, I was gonna give you a discount. I don't know, it seemed like an interesting idea at the time."

Randy was attentive, and showed no disdain, although he thought her answer was bullshit. She was a smart lady, that was obvious, but she had made a dumb decision in this instance. He now was curious and asked her, "Why pick me?" and her answer steeled his determination.

"Cause you seem harmless," she said with a sheepish grin.

Randy laughed quietly and raised her hand to his cheek, "Oh Anya. You're right, that's me, I'm harmless," and he nodded his head towards her throat, "What's this lace choker you have on? You've worn it every time I've seen you."

Anya looked down, as if she could see it, and then back to him, "It's just an accessory. I like it."

Not buying it, Randy tilted his head toward her and looked out the top of his eyes, "And that's all it is?"

The beginnings of a smile barely showed at the corners of her mouth, "Well," and she drew the word out as she said it.

Randy decided it was time to lay down cards and see what the score was, "Okay then Anya, if this wasn't just a ploy and you really are horny," and her face showed interest, "I have my own proposition for you. I'll make you a bet. We go to my place and we fuck each other's brains out, but no foreplay other than kissing. If I cum first, I'll give you $50,000 cash," and she grinned a devilish grin, "But, and it's a big but, if you cum first, I get to do whatever I want with you for the rest of the holiday until Tuesday morning. I don't know how you conduct your business in New York, but if faking orgasms is part of your usual method of operation, this time you won't have to."

She removed her hand from his and drew a fingernail gently across his cheek to his chin and told him with the utmost confidence, "Oh, Randy. I don't want to take all your money."

"Hold on just a sec," and he pulled out his cellphone and accessed his online banking app and let her briefly view his current balance.

She could not hide her confusion, "That's yours? But I thought you were," and he cut her off.

"Bigger fish than you thought, huh. Next time you might want a bigger boat when you go trolling. Now, is it a bet or not?"

In Anya's mind she tried to suppress the thought that it'd be the easiest money she's ever made, nonetheless she was now intrigued by the proposition, even though the fact that he apparently knew the symbolism of her choker should have been a warning.

"It's a bet. Your place or mine?"

Randy's dick poked up its head for the first time as he told her to follow him in her car and he'd lead the way. He had Sam put his drink in a to-go cup and paid him for their meal and drinks, then took Anya's arm and led her out to the parking lot.

On the drive northward he took a little blue pill from the console and downed it with the drink, all the while checking to make sure her silver BMW was still behind his pickup.

He parked in the garage and waited as she exited and then led her inside the front door that was between the round guestroom part of the home and the garage.

They traveled through the foyer and into the kitchen/dining area. Beyond to the right was the round living room and straight ahead was a wall of windows looking out upon the pool and beyond it and down the dunes, the ocean. She did not notice as he flipped on the video recorder for the cameras located throughout the house, nor as he quietly removed his pistol and placed it in a cabinet.

"So Anya, why are we here again?"

She turned to face him and smiled, "To settle a bet, who can make the other cum first," and she reached behind her and unzipped her blue dress, letting it fall to the floor and leaving her in only a blue thong and the stripper heels.

Her tits were small, maybe the size of a baseball with perky nipples that turned up. Years ago, the boys in high school had called them stargazers and hers were hard as rocks.

She called him to her with a forefinger as she led the way to the sunken living room and Randy undressed as he followed. Once there, she stopped and faced him, "You said no foreplay, right?" and her eyes swelled as she caught her first glimpse of his cock. "Oh my!" and she trapped the lacquered blue nail of a forefinger between her teeth.

Randy reached out and grabbed her, pulling her toward him, "Wrong, I said no foreplay other than kissing," and he filled both hands with her round ass and pulled her tight as he buried his tongue in her mouth and she returned his effort in kind.

She kept trying to work her hands in between their bodies to get them on the cock that was pressed against her midsection, the head just at the bottom of her cleavage. But Randy pulled her tightly into him by her ass and bent her backwards with each attempt and she eventually relented.

He broke the kiss and took both her arms by the wrists, twisting them behind her and holding her there as he tongued her ear and whispered, "Your specialty that you sell in New York is that you are a sub, isn't it?"

"Yes," she answered yearningly.

"What do you want right now Anya?"

"To win the bet," and she lightly bit his ear.