A Randy Retirement Pt 20 Halley

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: Halley returns for NYE

December, 2017 - River House

It was Christmas Eve. Another get-together of the extended family. All the second or third spouses; kids, step-kids, and adopted kids; grandkids and great grandkids had made the pilgramage and gathered. It had grown too big for Randy's parents' home, so it was a good thing his brother had a big house. Why? Because that kept anyone from suggesting they hold it at his house. Other than a bowl of green M&Ms, he didn't even decorate, much less put up a tree.

Randy's step-grand nieces, Halley and her sister Gabbie had commandeered the fireplace hearth and keep giggling while stealing glances in Randy's direction as he sat across the room in a wingback chair. This was the house where he had caught Halley trying to have sex with her boyfriend and the journey of their relationship had begun. As that thought entered his head, he turned and pointedly looked down the hallway to the bedroom where he had burst in on them. Halley caught the gesture and the meaning and dipped her head in acknowledgment, a thin smile on her face.

After the meal, when it was time to open presents, Gabbie came and sat on a footstool beside him. The younger children delivered the presents after being instruced by those slightly older to whom to make the delivery. Only after the area around the tree was bare, could they delve into their pile of colorful boxes. In the frenzy of it all, a hiss escaped Gabbie's lips as she watched her older sister open a box with some ankle boots.

"Problem?" Randy asked her.

She answered without looking at him, "No, not really a problem, it's just that Halley is so tall. She doesn't need boots. I need boots."

"Being short has its advantages Gabbie," he whispered to her.

She turned to him, "How's that?"

"Well, if you're short, it's easier for your boyfriend to pick you up and play with you."

Her eyes widen and then a tiny smile came over her face, along with a little pink in her cheeks.

Later, as things began to wind down, Halley came beside him for the first time that night as he was in the kitchen putting sugar in a cup of coffee and whispered covertly.

"We on?"

"Yes. I'm making dinner, dress up," he murmured back.

She deftly swung her ass sideways and bumped her hip into his, almost making him spill his coffee, "Rest up."

*

New Year's Eve was on a Saturday and over the next week they worked out by text that she would stay with him that night before she had to head back to college and her two jobs in Savannah on Sunday.

Randy made dinner for them, a lentil soup with Italian sausage to start, followed by lobster ravioli in a white cream sauce and topped by diced tomatoes. He had a bottle of Chardonnay chilled. Then he put on a charcoal gray pinstriped suit with a black shirt and red tie and sat to await her arrival.

He had compiled a playlist that consisted of a host of classical romantic music to set the mood and hit the play button just before seven when the security system alerted him that someone had entered the open gate. He hit the switch to close it and went to the front door.

As she parked the car, he opened the door and was greeted by a vision. She wore a long, off-white evening gown and carried an overnight bag. The dress plunged into a V, front and back, the back stopping just above her tailbone, the front just above her navel. Halley's 32-Cs filled it out nicely and the material was very clingy, highlighting the shape of her thighs and ass. On the sides it also plunged, to the top of her hip bone and was held together by three evenly spaced strands of silver chain.

"Damn woman, I hope you didn't pay a lot for that dress 'cause I may just rip it off you."

She came close, still holding her bag, and Randy's hands found the bare skin just above her hips. "Better not 'cause I did. This is the first time I can ever remember seeing you in a suit. You should wear one more often," and she kissed him briefly on the lips.

She began to pull away and he held her there, "How much?"

"I bought it with some of the money you slipped into my account. Yeah, I know." Randy tried not to smile and failed. He had been secretly depositing a thousand dollars a month into her checking account. "It cost $450, and the only reason I bought it was to wear it for you."

He was both surprised and happy that she had noticed the money. It meant she kept up with her finances. Still, he felt the need to apologize. "Halley, I just wanted you to have some walking around money since you won't let me help with your schooling. I'm sorry if you feel it was out of line."

"I know why you do it and it's okay. You sticking to not paying for my college is the only reason I haven't called you up and cussed you out," and she gave him a sincere smile to emphasize the point. "Like I told you, I don't do much walking around, so I spend it on food and clothes, to wear for you. Just don't put more than a thousand a month in there, okay."

"Yes ma'am," he told her somberly, then changed the subject, "I hope you're hungry, 'cause dinner's ready."

"I am. I've been looking forward to it. Just let me put my bag in your room and I'll meet you in the kitchen," and she turned from his embrace towards his office door.

"We're eating in the dining room."

Halley turned halfway back to him and raised her eyebrows, "Goin' all out, are we?"

Randy just laughed and waved her off as he turned to go and fix their plates. As he set the food on the table, then lit the candelabra, he thought about how he had fucked more on his dining room table than he had eaten on it and shook his head sardonically.

Halley made her way back and he pulled out a chair for her. Most of the lights in the house were off, with only the dim lighting from the wall sconces and the three white candles. Still, he had enough light to see Halley as she gave him peeks of her tits at the table. The V on the front of her dress was very loose, especially when she bent her neck to eat some of the soup. As they ate by candlelight on paper plates and plastic utensils, he could easily see the curve of the underside of her right breast.

He explained to her what she was eating, as Halley ate and she told him that he had outdone himself. Another minute or two passed and then she made another declaration.

"This is strange."

"Why's that?" Randy inquired, thinking some smart-assed comment was coming about the food.

She picked up her plate and set it down, then held up her plastic fork, "This."

"Oh, I thought you meant the dinner," and he held up his own plastic spoon, "It's so we don't have to wash dishes after the meal."

She broke into a grin then, her eyes twinkling. "Oh. Good. I like the way you think."

They continued to eat, and he asked what she and her sister Gabbie were giggling about at Christmas.

"Oh that," and she patted her mouth with her paper napkin. "Gabbie kept making comments about how fine you looked and wondered why you were married. It was all I could do not to say something about our arrangement, or even your whoring around, so I just tried to play it off and we got to giggling."

Randy laughed, "Well, I guess our arrangement, as you call it, can lead to some interesting conversations."

"Yeah, well, I try to avoid those as much a possible."

He decided not to pursue her reply.

They finished their meal and Halley complimented him again on the meal as they trashed their plates and made their way to the living room, holding hands as they went.

There was not a lot of talk, as they sat on the couch and listened to the music he had chosen. It was enough to be in each other's presence again for the moment. Occasionally she would ask about a song and he would explain to her its provenance. Beyond that they snuggled in each other's arms, and watched the moon rise in the eastern sky as the music played in the background. Each of them knew, as they sat there and time ticked away, that the desire, the want, the need, was slowly building inside of them. It was palpable.

At eleven-twenty, he got up to get them each a bottle of water and when he returned, he made a big production of taking one of the little blue pills in front of her.

Laughing, she reached down to the coffee table and took a handful of the green coated candy that was in a glass dish, "This will do for me," and she popped two in her mouth. "By the way, how do you always have all green, peanut M&Ms at Christmas?"

Still standing, he told her matter-of-factly, "Halley, when you have money it's amazing what you can get if you are willing to pay for it."

She nodded, then paused and took a swallow of water before replying, "That's one reason I won't let you pay for any of my schooling. I'm more than content being your slut, but I have no desire to be your paid whore."

He thought again about the thousand dollars he deposited into her account every month, but didn't bring it up and then she continued, "By the way, I was wondering, just how much money do you have?"

"Last time I added it all up, it was around a hundred million in cash, Give or take. Another twenty-five invested in the market and doing well and another twenty or so invested in real estate."

She was not shocked as she knew there was a lot, but she did wonder about a couple of aspects.

"That's the houses?"

"The houses and some other properties."

"I own some high-end vacation rental properties in several other states; Texas, Florida, Wyoming, Montana."

"Why those places?" she inquired.

"Because that's where folks with money take their vacations."

"Ah, I see. And the stocks?"

Randy smiled at her, "We're talking about stocks and it's almost midnight on New Year's Eve?"

Halley shrugged, "Just curious. Humor me. You never, and I mean never, talk about how much you have. Besides, the fact that we're gonna fuck tonight is a fait accompli, New Year's Eve or not."

"Oooo, good phrase," he teased her as he sarcastically bowed and then he considered for a moment before he gave her the answer. "The twenty-five is diversified throughout about a dozen blue-ship companies, all doing well. I keep track of the market so that I can buy and sell nimbly when the need arises, but for the most part, I let it ride. With what I do sell and the dividends from what I keep, it makes another million, give or take, each year. That twenty-five started out as a half million-dollar investment just to give me something to do with my time. Twenty-five is what it has grown to so far."

"Jeez."

"Having money makes it easier to make more money Halley," and he got up without another word, went to the source of the music and picked out a particular set of songs deep down the list. It was a song that wasn't classical, though it was a classic.

As the first notes of Eric Clapton's "Wonderful Tonight" started, he turned to her, holding out his hand. A pensive look on her face, she took another swallow of water and then came to him. They slow danced in the dim lights of the wall sconces, Halley resting her head on his shoulder. Just his touch sent the hormones screaming throughout her body and sent it down the path of explosion.

Randy watched her reflection in the windows as they shuffled. She had grown so much more self-assured in herself and her sexuality in such a short period of time. It was as if all she needed was something to give her a slight push, an opening, and then she took care of the rest. That push came the day he stumbled onto her and her gay boyfriend when they were eighteen. She was now twenty, going on thirty-five.

"You're beautiful Halley. I wish I could take you out and show you the world."

She looked at him, "Someday, just not yet. Though I'm caring less and less." Randy took note of the last part, but did not comment.

Neither of them was a dancer of note, but as Clapton ended, Johnny Rivers began, and they continued to sway to the music. Like the song, the shadows danced across the walls and the rest of the world seemed so far away and small. Her body was almost glued to his and the warmth of her loins was prevalent through the material of their clothes.

It was approaching midnight as the Rivers tune entered its last chorus and Randy moved them silently to an ice bucket near the spot where the windowed walls made the corner at the northeast end of the house. He took out a bottle of champagne, opened it, and poured them both a glass.

There were no spoken words, but they clinked glasses together in a silent toast and eyed each other as they drank. It was at that moment that Keith Whitley's "When You Say Nothing at All" started to play. They finished their champagne, listened to the song, and watched the full moon reflect on the river.

The sound of a clock striking midnight jarred the mood and Halley turned to him, "I didn't know you had a grandfather clock, where is it?"

"I don't. It's the security system. I set an alarm for midnight and selected the clock sound."

"Well dammit, I was wanting to see a clock," and she smiled at him as she moved closer. "Happy New Year asshole."

He embraced her, "Happy New Year Halley," and kissed her deeply, bending her back in his arms. The kiss led to fondling, his hand slipping inside her gown, and it wasn't long before he had undone the dress and slipped it over her head.

Randy was not surprised that Halley was naked underneath and he had her turn to face the glass, spread her feet wide, and put her hands to her sides, palms flat on the window. Her ass was sticking out and he rubbed it as he came to stand beside her, turning his back to the window, so they were facing opposite directions.

Halley let out her breath slowly as his fingers slid down her ass crack and he gently inserted his middle finger into her cunt from behind. It was already drooling.

"Whose pussy is this?" he asked as he plunged the finger deeper for emphasis.

"Yours," she replied without hesitation, turning her head to look at him proudly.

Randy moved his finger to her dry asshole, the only lubricant being her wetness. As he inserted it to the last knuckle, he asked, "And whose is this?"

In a low tone she answered, her voice trembling, "You know it's yours."

"Did you prepare yourself for me?" he asked with an arched eyebrow.

"Of course. It wouldn't be complete if you didn't fuck my ass," she smiled at him.

"Undress me," he told her, and she slipped the jacket from his shoulders to the floor and unknotted his tie.

"See, if you wore suits more often, you could tie me up with this," she taunted him, holding the tie up before she deposited it on the floor as well and started on his buttons.

Randy began to knead her nipples and slowed her down, her fingers not working as nimbly while his sent jolts of electricity through her tits.

When she reached down and fumbled with his belt buckle, he taunted her back. "I thought you wanted to fuck?"

She moved in to kiss him then, passionately as she finally freed the belt and pushed his trousers off his hips to the floor. Her body slowly followed them and she squatted to remove his shoes, socks, pants, and boxers. When she finished, she rose and wrapped her long body around his, kissing him deeply again, "Take me to the playroom."

In the elevator, she nibbled on his ear while she fondled his engorged cock, "I want you to fuck me like a slut."

Randy just stared at her, and the act served to energize the hormones that coursed through their bodies.

The first thing he did once inside the playroom was to hand Halley the set of XXL nipple suckers they had used before. She did not need instruction as she licked them, drooled on her own nipples, and then attached the silicone cups, wallowing in the feel of her puffy nipples as they expanded inside them and grew larger.

He had left her to the task while he retrieved some items from the storeroom and when he returned, had her lay on a padded box that was against the left side wall about two-thirds of the way into the room. He knelt and spread her legs, Halley's bare pussy beckoning to him, and began to lick it.

Using his tongue, he massaged her clit, forcefully working it into her flesh and then did the same to the area around her urethra. Halley began to softly pant and he inserted a finger and worked on her G-spot. In no time, she had put both her hands on his head and tried to push his face deeper into her sex.

This prompted Randy to redouble his efforts and he reverted to an old tactic of his, lightly biting her now exposed clit and sucking hard on it. Immediately her legs tried to close around his head as she yelped in delight, but Randy pinned them down with his elbows and kept up his oral assault.

"Oooo, dammit! You're gonna make me cum!!" she shouted, the words coming out rapidly with no breaks between them. It was then that her body seemed to fold in on itself as she convulsed, and Randy got a rush of her juices on his chin.

He stood and wiped off his face as he took in her gasping body, her head lolled to the side as she eyed him with a satisfied little smile.

"That was good," she managed to pant out. "It's been so long."

"Just good? Damn, I'm slipping," and he pulled her to her feet. "I want you to lightly tweak those nipple suckers, but do not take them off. Understand?"

Halley tilted her head forward, looking at him through her eyebrows, as her hands came to the cups, and mocked him, "Understood."

The mocking, the taunts, her calling him an asshole, him calling her a slut, it was all a little game they played, an adding of a little nitrous oxide to their building combustion.

He began strapping her ankles into suspension cuffs as she closed her eyes and drifted off to the pull of the suction on each of her breasts. When he had finished, he led her between two six-by-six wooden posts that had been bolted into the floor four feet apart in the far back corner of the room, right beside the steel autopsy table.

She looked on as he also strapped her wrists in suspension cuffs and attached them to metal rings at the top of the lacquered posts, pulling her arms wide and down as the posts were only three feet high. Randy then stooped and pulled an ankle to each post and clipped it to metal rings on the bottom. Halley was now slightly hunched over, with her knees bent. It would have been a difficult position to maintain if he had left her there.

Reaching out, he pulled the cups off her tits, revealing two fat, puffy nipples. They were at least two and a half inches around and the same in length and were now swollen and a deep, dark pink in color, just before turning an angry red.

He massaged them roughly between thumb and forefinger and watched her face as she struggled to contain a reaction. Smiling, he told her, "I love your tits, you know that?"

Through gritted teeth she responded, "They're not too small for you?"

"Nope. Just right. More than a mouthful is wasted," and he bent to suck hard on each nipple to emphasize the point. When he stood straight again, he resumed his manipulation of her flesh and continued, "Big tits have their place, they're fun to play with, but my personal preference is a breast that fits in my hand, like yours," and he hefted her left breast, "and nipples that get good and rigid when the owner gets hot."