A Randy Retirement Pt. 29: 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: Return engagement for Call Girl

September, 2018 — OBX house

Sam was retired military, but spent his retirement as the regular bartender of a pizza place in Corolla on the North Carolina Outer Banks. It so happened to be Randy’s favorite casual hang-out.

The elderly gentleman was wiping down the bar on the Friday night of Labor Day weekend when a twenty-seven-year-old woman walked in. She had been there before, but it had been a few years earlier. Even so, Sam remembered her face, if not her name.

“Hello and welcome back,” he greeted her and fumbled with the bar towel in his hands.

“Good to be back, I hope,” she replied as she searched the dining area, particularly the corner table to her right near the kitchen.

She was dressed to the nines in a black chiffon dress that came to mid-thigh and showed off her modest cleavage. Black cowboy boots with turquoise designs on them and turquoise Sam knew. “He was here last night for supper.”

“Is he coming tonight?” she inquired as she ate one of the olives.

“I don’t know,” the elder man replied, “sometimes he comes in on back-to-back nights, sometimes he don’t. Would you like me to call him?”

“Would you?” She clasped his hand on the bar, the warmth of it exciting the old man further. “That would be great. I lost my phone a year ago and lost his number.”

Sam hesitated, the warm feeling still there even after she had taken back her hand. He shook himself from his reverie, went back to the cash register and pulled out his flip phone. He found the number in his contacts and hit ‘Dial.’

Randy was watching the weather channel on television when the phone rang. There was a storm brewing out in the Atlantic that might be headed his way and Ellie was supposed to come visit in a week. He wondered if it might infringe on their time together as he reached for his cell and checked the screen. Wondering why Sam was calling him on a Friday night, he answered on the third ring.


Without preamble, Sam blurted out, “I need you to come to the bar.”

“Well hello Sam. Why would you need me to come to the bar?”

“Don’t ask why, just come,” Sam was insistent, “Come now.”

“Is something wrong Sam?”

“No, nothing’s wrong, just get in your damn truck and come down here, now,” and the older man emphasized the last word as he turned to look at her, pointed at the phone and shook his head with a smile.

Randy replied, “I didn’t realize y’all were that hard up for business Sam, that you had to call folks to come eat.”

Sam turned away from her and whispered into the phone, “It’s not that, young feller. I got a surprise for you, get your ass down here, NOW!”

Randy told him that he’ll be there in fifteen minutes, his curiosity piqued as he grabbed his keys and headed out.


As he drove his mind wandered to his most recent conquest. The entire month of August Randy had spent at his River House, playing golf every day. Gabbie had found a way to come play with his cock for all but three of the days left in the month after their first week of debauchery. He had alternated between her ass and pussy, fucking one or the other exclusively each visit she made, but Gab always spent at least twenty minutes each visit with his cock down her throat. Sometimes he tied her up while he screwed her, but he didn’t put her in any of the playroom devices again; choosing to save that for later if she kept coming back. Every time she arrived at his door, she was fresh as a daisy and smiling, taking his cock enthusiastically over and over just like an eighteen-year-old nymphomaniac would.

She had pouted when he told her he was headed to the Outer Banks for the entire month of September. Randy insisted that she needed to concentrate on the start of her senior year of high school and that he would be a distraction. What followed was a lecture on the Ofise Gelen Escort importance of education and perseverance.

He let her know that he’d be back sometime in October and wanted to see her grades, but that under no circumstances was she to skip school and come to see him. She didn’t like that, but made him a promise that she would concentrate on school and not come to the Outer Banks, and he let it ride with her promise.


The woman at the bar in the pizza joint was also lost in thought as she waited. Randy had told her the last time she saw him to always be wary of fossils like him, but her mind had occasionally drifted back to him in the last two years.

He saw her as soon as he entered, walked over, and sat next to her. He said hello to Sam, asking for a sweet tea, then turned to the young lady. Immediately he noticed that her face was more tight and drawn than he remembered. She must have really been on a health kick.

“Hello Anya.”

The ice gray eyes sparkled as she smiled sheepishly at him, “Hello, I hope you like surprises.”

“I love this kind of surprise,” and Sam brought his tea. “Thanks Sam, and thanks for the drink too.” The old man winked in reply.

“Can I get you another?” Sam asked Anya, patting the bar in front of her where her glass sat empty.

“Yes, please. Thank you.” She turned to Randy, holding the empty toothpick from the olives in her teeth, her elbow propped on the bar.

“I watched your movie,” she announced proudly.

“Excuse me?”

“Your movie. Hardbodies. I watched it.” She paused and set the toothpick on the bar, staring at it, “It was cute.”

Randy chuckled. Sam brought her second drink and Randy paused to let him depart before asking, “You just came down on the chance I’d be here?”

She took a sip and set the glass back down, removing the new set of olives and eating one seductively, “Pretty much. Kinda crazy, huh. I lost my phone, so I lost your number. This was the only option I had left.”

“Oh, that’s a bitch.”

“Yeah, it is. I lost my entire contact list, clients too. Took me six months to even get it close to back to normal. Anyways,” and she sat up straighter on the barstool, “I’m moving to Cali next week and I decided before I left to take a flyer. I probably won’t be getting back to the East Coast for a while and … well, I was hoping for one more go at the grand fossil,” and she smiled coquettishly at him.

The first time they had met, Anya had tried to solicit Randy and when he told her he didn’t pay for sex she had referred to his age by telling him that she didn’t fuck fossils for free. That had led to the movie reference and to him drilling her at his house for the rest of the weekend … for free.

“Finish your drink, I have some beef stew in a slow cooker at the house and there’s enough for two.”

Anya downed her martini in one gulp, pronounced herself ready, and got up. Sam came over and Randy threw a twenty on the bar, “That cover it?” he asked.

“Yep,” and Sam reached for the bill.

Randy threw another twenty down, “Have a good night Sam. That’s for being my pimp.” Anya blushed and smiled as Sam picked up the bills. She mouthed “Thank you” to him as she grabbed up her purse and Randy ushered her out.


Having cut a small chuck roast into one-inch pieces, Randy had browned it in a frying pan before dumping it and it’s juices into the crock pot, along with potatoes, carrots, onions, and celery that he’d also cut into pieces. He added no water, instead using beef broth and half a bottle of merlot.

Anya had sat in one of the captain’s chairs at the kitchen island while Randy dipped her a bowl and served it with some French bread and red wine.

He joined her, but with water to drink and she complimented his cooking skills after a few bites.

“Thank you,” Randy replied.

“You know, I’m kinda surprised you hadn’t already called one of the ladies in your little black book for tonight. Lucky me I guess.”

Randy put down the piece of bread in his hand and wiped his mouth on a paper towel. He took a swallow of water before responding.

“I don’t have a little black book and I haven’t called a woman to come over in at least fifteen years. Certainly not since I retired from teaching.”

“You don’t call women to come over?”

He shook his head side to side slowly, “They call me,” and her eyes filled with mirth. “Don’t get me wrong now, I pursue them. I enticed them. I dare them. But once I’ve had them, I don’t call them back, they either call me back or we call it even. I discovered that there are plenty of women out there who’ll put out if the situation is Otele Gelen Escort right.”

He could see the heat build in her eyes and realized Anya was getting off on his little revelation, so he continued.

“Actually, I don’t let them call, they have to text. Most of them are submissive by nature and follow direction well. Speaking of which, I notice your lace choker is missing.”

Anya’s hand immediately touched her throat and then she smiled and replied, “Yeah. I still like to submit; I’ve just gotten more selective about advertising it.”

“Live and learn,” he commented, and she nodded as she resumed her meal.

When they had finished, she told him to sit and let her clean up. She took both their plates to the sink, ran the garbage disposal, and rinsed them before filling the dish washer and asking for directions on how to start it. As she came around the island, she picked up a banana from the fruit basket on the dining table and sat again in her chair beside him. She peeled it slowly, then provocatively ate it as they sat in silence for a moment.

“Are you trying to tease me?” he finally asked.

“Yes, of course,” and she gave him her sexiest smile.

Randy stood then, “Don’t you want something more substantial?” He dropped his pants and flipped his hardening cock out over the waistband of his boxers. “I mean, after all, this is why you’re here, isn’t it?”

She left the rest of the banana on the counter and dropped to her knees. Randy watched her face, all her skin taut, her lips full and stretched around his shaft, just past the corona. There was not an ounce of fat anywhere on her body that he could see.

Anya began doing something that he did not remember from her first visit, curling the sides of her tongue upward to form a sort of trough to guide his cock deeper, though she did not take him completely the entire time she worked him over. She had skills though, and in time she achieved her objective.

After Randy had cum in her throat and withdrawn, Anya pinched and pulled her nipples hard, shuddering so violently that the little drops of his jism on her chin fell to the floor. Randy bent and cupped her chin, “Did you just cum?”

She smiled, some of his semen still on her lips, and replied, “A little.”

Then taking his ten inches in her hand, Anya swiped a streak of whiteness across her cheek from the tip as she spanked her jaw with it.

“A little,” he repeated her answer sarcastically.

“Yep,” she smiled as she gathered the last vestige of his seed with a forefinger and swallowed it with playful eyes while starting to rise.

He stopped her dead by asking, “Who said you were finished?”

Her face leered and then Anya sunk back to the floor, Randy putting a hand on top of her head.

She looked up at him with puppy dog eyes, but took his cockhead toward her mouth anyway. Curling her tongue to fit it in, she rotated her head forward and this time slowly made the 10″ disappear. Unhurriedly she fucked her throat with his cock, gagging and retching, but not stopping.

Ten minutes later, with tears streaming down her face, Randy came again. He held her head firmly on his dick and groaned loudly as he emptied himself while Anya squirmed to keep up with the much larger flow that filled her throat.

“Why don’t we take this to the living room,” he suggested as she again wiped his seed away from her lips with her fingers and tongue.

She looked a mess as she stood and Randy undressed her, kissing every erogenous spot as he uncovered it, even her bare feet as he pulled the boots off. He then undressed himself, with Anya’s help, but pulled the belt from his chinos. He looped the strap back through the buckle and placed it over her head, pulling it semi-tight around her throat and leading her down the steps to the big round living room.

Things started with a kiss before they ended up on the floor. He noticed her smallish, east-west breasts, each nipple pointed outward as she lay on her back. Then it got rough as he rolled her up with her ankles around his neck and pounded away at both her ass and pussy while occasionally pulling on his belt just to heat her up a little more.

His cock entered either hole much easier than he remembered; it was so evident that it was striking, but Randy didn’t care. He cycled back and forth between the two and when Anya seemed close, he would idle down and slow fuck her.

She had already cum once by the time he felt another climax of his own begin its journey and Anya’s second orgasm occurred before he could nut. She grunted it out like some wild animal as he continued to pound her asshole and just as she quieted, Polatlı Escort he erupted.

Pulling out, Randy shot off in her face; huge, thick ropes of white cum that she sat up to receive. She ended up with a thick wad in her mouth that she rolled around on her tongue and showed him as a river of it flowed down between her breasts to her navel. She made a big deal of swallowing what was in her mouth as Randy stood up and removed his belt, noting that he would have to clean it later.

“How long are you here for?” he asked, holding his right hand out to her.

“I have to leave Tuesday morning,” she replied, taking the offered assistance.

“So, you wanna venture out or just stay here and fuck?”

Anya laughed softly, “We can go out to eat, but I’m not much on sightseeing.”

“That’ll work, but you said you weren’t coming back for a while. Is there nothing out here that you wanna see and experience?”

She ran her hand lightly across his chest, flicking his far nipple with her forefinger, “All the things I wanna see and experience are right here.”

Randy nodded.

“Why don’t you go wash off and I’ll gather our clothes and clear out the dishwasher. Then I’ll join you.”

“Okay,” and she kissed him on the cheek. As she turned to head for his bedroom, she got one big slap on her ass from his folded belt. Both her hands went immediately to cover her ass and she looked back over her shoulder without stopping and bit the corner of her lower lip, taunting him.


When Randy came in, he immediately noticed the red mark from the belt on her bare ass as she stood on tip toes and brushed her hair in the mirror above his dresser. She had already showered and dressed in a nightie that resembled a halter top, and that was it, no bottoms.

“I guess this means we’re fucking again,” he said into her ear as both his hands found her lean waist.

Anya drew in a breath seductively and settled her feet to the floor. Without turning, she watched him in the mirror and said, “My job is fucking. You are my vacation. I came here to be with you because it’s not my job, it’s my pleasure and I want to get as much pleasure as I can before I have to leave.”

From behind Randy’s fingers found her still wet cunt and two of them roughly entered, eliciting a moan in response. He pushed her chest down on the dresser with his free hand and pinned her there while his fingers dug deep into the wet pit of her vagina.

Getting her all worked up to the point her ass was undulating on his hand, he stopped suddenly, removed his fingers, and stood straight. When Anya turned her head back in question both of his slick fingers were presented to her, the implication obvious.

She took them into her mouth slowly, being as seductive as she could muster while her tongue first bathed them, then sucked them clean.

When she’d finished, Randy silently left her there and went to sit in one of the club chairs that faced the ocean. He heard Anya rummaging through her bags and wondered what she was up to, surprised at what she had brought with her when she finally came to join him.

She stood directly in front of him, naked save for the nightie, a tape measure in one hand and the other hand pulling the metal tape out and letting it snap back into the case.

“What’s that for?” he asked coolly.

She gave him a crooked smile, “I must know, if you’ll allow me of course.”

He gave her the slightest of nods and she hit her knees between his and measured the length of his erect cock.

“Ten and three-eighths inches,” she announced, as if she were working at an auction. “Would you hold it back a little so I can measure the width?”

Randy gave her what she wanted, and Anya bent her lead low, pulling the tape across the base of his dick and eyeballing it.

“Let’s see, two and one-sixteenth … maybe two and a fourth,” and she straightened up, still on her knees and pulled the tape out and let it snap back one final time.

“Happy?” he asked softly.

“Oh yes, what girl wouldn’t be?”

Randy bent toward her, taking off her top and grasping both her nipples, pinching them hard as she dropped the tape measure to the floor.

He issued an non-refusable invitation, “Come get ya some.”

He pulled her onto his lap by her nipples, her tongue swiping her upper lip in delight as she positioned herself and put him inside. The entire time she rode him, Randy held her nipples tightly with his fingers, his hands completely still so that her motion provided the pull. When she finally made him cum, Anya rotated her hips forward and back, grinding into him as he shot off inside her until she climaxed as well.

They took a quick shower together to wash off the sex and made their way to bed. A short kiss goodnight and she conformed her body to his. Just after Randy had turned the bedside light off, Anya snickered.

“What’s so funny?” his voice boomed in the darkness, louder than he intended.

It took her a moment to answer, but when she did her voice had a light-hearted tone to it.

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