A Randy Retirement Pt. 36: 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 summoned home for rendezvous

May, 2019 -- River House

It had been three weeks since the night Randy had introduced Gabbie to big black cock, along with spitroasting and double penetration.

In the interim he had been doing maintenance around the River House, though Gab interrupted him one Saturday for some maintenance of her own.

There was a section of the perimeter fence a hundred yards east of the gate where vines had started climbing the fence and Randy had been working in cargo shorts with his shirt off while clearing them. He was hot, sweat running like a river, when she called and he told her to come on over.

"Ten minutes out," Gabbie replied and hung up before he could respond.

He was still sweaty when she skidded to a stop as he sat on the front stoop waiting for her.

Randy knew as soon as Gab got out of the car that she was horny as hell, just by the way she walked up to him. Without slowing down, she wiped his chest with her forefinger and licked it, smiling at him before continuing to the front door. Randy just shook his head and laughed softly, allowing her to enter before he rose and followed her inside.

She was already naked, her clothes strewn in the foyer and her eyes wild as she crooked her finger and beckoned him to her.

His face impassive, he walked slowly to a spot just before her and watched as she went to her knees and began to untie his shoelaces and remove his work boots and thick socks. The cargo shorts and boxers followed, Randy dutifully raising the proper foot when appropriate, but not commenting.

She looked fresh as a daisy; nice tan, not worn or used up. But she was heated up and the whore inside was eager to be let out. Anya flashed briefly through Randy's mind, only to disappear when Gabbie spoke.

"Lay down and let me fuck myself," she told him.

"On the floor?" Randy asked.

"Floor, bed, stairs, I don't give a fuck, I just need your dick in me," she replied.

Randy reached down and grabbed her roughly by the hair at the back of her head, his other hand tightening around her throat as he pulled her to her feet.

"How bad do you want it?"

Gabbie was unable to answer, her face turning redder as her eyes pleaded with him, making his cock stiffer by the second. Finally, he let her go and she slouched, hands on both knees as she filled her lungs with fresh air.

Thirty seconds passed.

"You know ... choking me ... only makes me ... hotter," she said in segments, between deep breaths.

Randy did not answer and when she finally looked his way, he was flat on his back on the floor of the foyer, his cock rigid and pointing up at a 65-degree angle, waiting for her.

The nineteen-year-old blonde went to the object of her utmost desire, crouched over her grand, step-uncle on the balls of her feet. She relished the calm before the storm that was about to arrive as she descended slowly, once again into her happy place with a smirk on her face.

"What?" Randy inquired quietly once she had all of him inside her.

Warming up her pussy on his cock she told him, "I just thought of that saying, what is it? Ride or die?"

Randy smiled, "You're a loyal little whore, aren't you?"

Gab began to ride in earnest as she declared, "'til death do us part."

She leaned back then, her hands on the floor between his legs as she gave Randy a full view of her pussy being stretched by his dick. As she went faster and harder, her head lolled back and she cried out, "Oh god, it's so damned good!"

"Come here!" Randy growled in a very loud voice, breaking her stride as she looked at him. Her eyes were wide with want and he crooked his own finger and called her closer.

Gabbie rotated her torso down to him, her hips now grinding on the love rocket planted fully inside her womb, the fat head rapping on her cervix and driving her mad.

As she put both hands on the floor on either side of Randy's shoulders, he suddenly clamped her neck with both hands, one at the back and the other at the front. Gabbie fell completely silent but continued to grind even as Randy used his legs to thrust up into her.

Finally, a choked cry escaped her lips. It revealed the rip in the space/time continuum that was occurring as her orgasm arrived; her hands coming up to pound helplessly on his chest as she shivered uncontrollably. The crest was announced as her lips flapped, saliva flying while her eyes rolled back in her head.

It was all too much for Randy and he unloaded as deep inside the teen as possible, his hips twitching up with each shot as he held her still by her throat.

*

"When is my latex outfit coming in?" she asked him afterwards.

"Soon," Randy told her, making a mental note to himself to call and check with the manufacturer out in Arizona.

Gabbie inspected the outline of his body's perspiration on the wooden floor and commented, "I told you that choking me only makes me hotter ... makes me cum harder too." She smiled as she pulled her top over her head.

"You wanted it rougher, remember? You good now?" Randy asked. "I mean, can I to go back to work?"

"Yeah, yeah. You loved it as much as I did," she shot back.

"This is true. You are an exceptional little whore, Gabbie. But the question remains. Are you good now?"

She winked at him and headed for the door, "I am." Then she turned and blew him a kiss, "At least until I need you again." She paused for a second in thought and Randy patiently let her flesh it out.

Finally, she looked up at his eyes again, that impish smile revealing.

"You know, sometimes things become a blur when I am engaged ... when I'm fuckin' you. All I want, all that matters, is that moment when it all comes together."

Gab winked at him again and then she was gone.

***

In those three weeks, other than the sweaty quickie with Gab, there had been one or two instances in the grocery store when Randy had contemplated, but not acted upon, making a play for some strange that struck his fancy. But that had been dulled the last Thursday of April.

He had been in the pharmacy area, squatted down while he looked for something on the bottom row of shelves when his eyes were diverted by a pair of six-inch heels. They were attached to what could best be described as 80's rocker shoes, those platform things that looked impossible to wear.

As his eyes rose slowly in wonder, he found a woman about his age who was also perusing the shelves and completely unaware that he was taking her in. She wore a fringed shawl, but Randy could tell that she was thin, with granny glasses and graying hair. There was nothing remotely remarkable about her, nor anything revolting, but Randy felt a pang of disappointment and almost immediately wondered why he was disappointed as he made his way to the checkout lane.

'Is that what I'm headed for, holding onto glory days?' he thought to himself as he made himself busy looking at the magazines near the register.

Once in the car he got an irresistible urge to fuck Halley's ass and pulled out his phone. His encounter with the aging rocker had led him to decide to conduct a test and he fired off a text.

'Need your ass. Come see me. I miss you. Come now or ASAP!!! If not, I'm coming to Savannah. I'm not kidding.'

He put his phone in the cup holder and cranked the vehicle, saying aloud to himself, "I guess we'll see if she's really at my beck and call."

Just before he got home the phone dinged, but he left it alone. When it chimed a second time to remind him, it was like an insistent hot poker that burned a hole in his mind and once he had parked in the garage, he picked up the smartphone.

'i can get away the first weekend of may, is that okay'

That was a week away. Randy sighed and looked out at the inside of his garage, everything neatly in its proper place as his mind raced.

He had just decided that it would have to make do when the phone dinged again.

'is that okay' Halley repeated.

'Yes, be prepared,' was his reply and she sent back a smiley face with hearts for eyes.

***

A week later, the first Friday of May.

Halley arrived just before dark. She wore a black, low-cut jumper that highlighted her long legs and peach booty, her green eyes shining at him. The material clung to her, enhancing her ass in mouthwatering fashion.

It was then that Randy realized his summons was a crowning achievement for Halley. In her mind it meant that he needed her just as much as she needed him, and Randy admitted that truth to himself as she filled his arms.

The tall blonde had a way of conforming her long body to his, as if they were melded together as one and Randy filled his hands with her ass, relishing the tightness of her cheeks as she held him close.

"So I'm a stand-by now?" she asked after the first kiss.

"What?" Randy replied, taken aback.

"You must be in a dry spell, so you sent for me," she said, a grin on her face.

Randy cocked his head to the side and paused.

"There is some truth to that, but you're no stand-by Halley. It's been four months since I've had you and I didn't want things to go as long as last year."

She looked down sheepishly, "Yeah, I know. Things keep getting in the way. I apologize."

"No, no, don't apologize. I didn't say it to get an apology. I know school and work is time consuming and things get hectic. That wasn't the point. It's just ..." and his voice trailed off.

"It's just what?" she asked, her head tilting so she could look into his eyes.

"Oh, I don't know. I saw a lady in the store, and she was my age, maybe a little older, and just plain. She didn't appeal to me at all, not that there was a thing in the world wrong with her. She wore clothes from like forty years ago and for some reason it made me think of myself and wonder if I was trying to make up for lost time in my past and acting like a fool."

"Made you think about mortality, did she?" Halley asked.

Randy grimaced, "I guess, kinda, sorta."

She laughed as she said, "Kinda, sorta. What the fuck does that even mean?"

"It means maybe."

"Well, let me assure you, you're fine and there's definitely nothing plain about you," and she smiled erotically as she embraced him again, then whispered in his ear, "I hear you got a bigger dick now."

"Your sister Gab's been gabbing?"

"Oh, that's cute," Halley grinned sarcastically. "Yeah, she was pretty excited when she called me."

They were fully entangled with one another now, Randy looking into her eyes from inches away as she was almost as tall as he.

"That all she told you about that day?"

"Pretty much. She's got to where she doesn't get into details about what y'all do, probably because I didn't reciprocate when she first started coming to see you regularly and would tell me everything y'all did."

"Why didn't you reciprocate?"

"Because the details of what we do is between us."

A fleeting thought ran through Randy's head, that what he had planned for some day in the future might not come to fruition if Halley had that attitude about everything. 'Pryor' he thought.

"So, she didn't tell you she got some big black cock?"

Halley face showed her shock, "Do what?"

"Last time she was here I called one of my former players and we both fucked her. He's black. Not as big as me of course, but big enough."

Slowly she shook her head and Randy couldn't tell if she was repulsed or intrigued. "Of course," was the first thing she said, a hint of sarcasm again. Then she addressed the new revelation, "No, she didn't mention the black guy."

"Does it bother you? Not that she didn't mention it, but that he was black?"

Halley paused just an instant before delivering her answer, but when she did Randy was proud of her.

"No, not really. It's just that I've never really thought about it, so it's kind of a surprise." She paused again, her eyes showing that her mind was processing furiously, and Randy waited to see if she got there. Again, he was not disappointed.

"Wait a minute ... you both fucked her? At the same time?"

He nodded, "A double penetration and a spitroast. She loved it. That something you'd be interested in some day?"

Halley had a lost look of contemplation and again took her time to reply.

"Maybe, I dunno. I've never really thought about that either. Let me answer that later, okay?"

"Certainly," Randy replied and went straight to the next subject. "I've got something new I want to show you."

"Okay," she said softly, the thought of black cock departing her mind as a chill ran up her spine.

Randy led Halley silently up the stairs, across the catwalk, through the library and past the guest rooms before he turned and faced her as they stood in front of the air-powered doors of what Halley thought of as the Pleasure Room.

"When I texted you it was because I had a sudden urge ... a need to be inside your ass ... right then."

Halley did not reply, but she did show him all her teeth in a proud grin.

"Hold that smile 'cause I'm gonna rock your world," he stated flatly as he hit the switch and the doors swished open.

The entire space was in total darkness, save for a spotlight right in the middle and inside the circle of light was the seatless, metal chair.

Halley stepped into the room, stopping just before the light, and saw several things lying to the side of the chair, but it was all too much for her to attempt to comprehend as Randy heard her say to herself, "Oh what fresh hell is this?"

From behind he unzipped the black jumper and pulled it off her shoulders, letting it sensually slide down her long body to the floor, the material shimmering around her curves. Halley stepped out of her clogs and forward, past the boundary of the lighted circle, and Randy's hands found her waist before slowly sliding forward and up to fondle her breasts.

Her body was more cut than before, her muscle tone more defined and her abs tight. Randy concluded she must have started working out and the result was striking.

"So long," he heard her utter softly, almost silently.

He pulled on her puffy nipples, already erect, and walked her by them to the back of the chair.

"Hands on the back," Randy said sternly as he let go and she complied, her feet automatically widening as her torso went parallel to the floor, letting her breasts hang freely.

Randy picked up a squirt bottle from the floor and liberally squeezed half of the water-based lube into her asshole as Halley's head lowered and she began to coo.

She had her hands on each corner of the back of the chair, her head hanging in between her arms as she saw Randy's feet step up between her legs.

Haltingly she asked, "Go slow at first, it's been a while."

"Un-huh," he grunted and with that pushed the head of his cock past the slickened ring of muscles that guarded her colon. It wasn't violent, it wasn't hard, but he steadily pushed the shaft of his cock as deep as it would go in one motion, Halley's head rising as she yelped.

Once he stood still, his dick impaled fully inside her, she whispered again as her body sought to assimilate to his cock, "Oh god, it's still as good as it was the very first time."

With that, Randy wrapped her long blonde hair in his right hand, pulling her head back as he ordered, "Do not let go of the chair," and then proceeded to pound her ass until he came deep inside her with a roar of conquest. It took eighteen minutes and Halley had cum twice, the gibberish flying from her lips as her big ass quaked while Randy continued unabated.

Once he had dumped his load, he pulled out and immediately shoved a huge, pear-shaped anal plug where his cock had been, her ass sucking it inside and snugging the retainer tight once the widest part had passed her anal ring.

It was as if the two of them had never been apart.

Again, with a handful of hair he forced her to sit on the chair, her ass sinking down where the seat would have been. Bending her legs back severely along the sides of the seat, he secured her ankles alongside her hips, forcing her thighs to stay wide and giving him full access.

He ran his fingers across her snatch once before standing and found that it was dripping from her first orgasm.

"You slut," Randy said as he stood and Halley responded with a guttural moan.

He pulled her arms behind the back of the chair, tying them together at her elbows before securing her wrists to the seat adjacent to the crack of her ass. He then gagged her with a ring gag, which held her mouth open wide as the moans continued in a different tone.

The moaning increased as he began to play with her pussy and clit with a pink slim-vibe, teasing her relentlessly, but not letting her orgasm. He noticed how the retainer of the ass-plug moved, in and out, as if it were fucking her. The closer he let Halley get to cumming, the faster the plug moved.

Drool covered the inner half of her tits as she continually made noises as if begging, a cord of saliva connecting her mouth to her breasts until she shook her chest furiously and let out a garbled plea for relief.

For a half an hour Randy edged her, slowly, methodically. He played the vibe over her pussy lips, put it inside, and splayed the hood of her clit with his other hand so that he could work on her love bud without mercy.

Finally, he raised his voice and commanded, "Cum for me slut!" and with that he used his off-hand to fingerbang her as he pressed the vibrator hard on her clit.

Halley's chin dropped to her chest and a low, growl ensued, the drool multiplying. Her face was bright red, the freckles a darker hue and she carried a pink glow as miniscule sweat beads covered her spotlighted body. Slowly her head began to rise and as it did the rat-a-tat-tat of throttled gobbledygook began until her body seized in a slow-motion release.

*

Randy had removed the anal plug and untied her; leaving Halley in the seatless chair as she caught her breath.

"You been working out?" he asked.

Weakly the smile came, "You noticed."

"I notice all but everything, Halley. It looks good on you, it's not always that you can improve on perfection; I didn't think it was possible, but your body is even more luscious."

She was reviving quickly now.

"Aw, that's sweet. You're such a paradox."

"How so?" he asked.

"Like that comment, right after this." She stood up and with her hands indicated the chair and the edging he had just subjected her to before he had allowed her cum. "That was rather mean."

"Did you get off?"

She smiled, "Yes."

"Hard?"

"It was pretty intense."

"Then what's the problem?"

Halley laughed softly, "No problem asshole."

With that, Randy pulled her roughly to him.

"No problem huh?"

Halley was surprised and delighted, telling him in her best sexy voice, "Do my ass again please."

Randy brought her behind the chair, raised her left leg and put it over his shoulder as he turned her slightly in a standing split. Halley grabbed the chair back again as her body turned and Randy positioned his feet on either side of her right foot on the floor. He lined his cock up with her ass that was dripping lube and sperm from the removal of the plug, and plunged inside.