A Randy Retirement Pt. 06: Halley Ch. 03

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 and fictional. All stories can stand alone, but reading the series gives added insights and descriptions as it unfolds.

Synopsis: Teen blonde spends July 4th week with her step-uncle for bondage and rough sex.

July, 2016 -- River House

It was already past noon on Friday morning when Randy walked to the foot of his bed. Halley was half awake, lying there and luxuriating in the fact she had all day with him.

"HEY!" he hollered before saying in a softer voice, "Wake up sleepy head, you're wasting half the day!"

"Asshole," came the reply from under the sheet.

"Alright, as you wish. I guess you don't want any," and he turned to leave.

Halley rose from the bed and crawled to the foot, turning him back around by his hand. The sheet had fallen away as she had risen on her knees and her long, lean body radiated sex. "Come to bed and fuck me."

"Not yet. You have to eat breakfast," and he noticed that her nipples were still enlarged from the previous night's suction and pulled them gently. "You've been skipping meals too much this week and you need to keep your strength up. I don't want you passing out on me."

Halley purred, "Ooo, that feels good. A little sore, but good. My pussy is sore too. How about you fuck the soreness out of me and then we eat."

"Nope, we eat first. Go use the bathroom and then come to the kitchen," he was resolute and resisted her temptations.

"Oh, alright. Something to eat would be good. I am kinda hungry."

"That's a girl. Now, when you get dressed, do it for a little hike. We are going walking after we eat."

"Hiking?"

"Hiking," and he left the room for the kitchen.

Halley made her way to the bathroom and turned her back to the mirror, admiring the deep blue sapphire that capped the plug in her ass as she spread her cheeks. She squatted over the toilet, grabbed it in her right hand and began to pull. It required some effort as her asshole did not want to give the plug up, but she eventually won the battle and it released with a spark of electricity travelling up her spine. She set it in the sink as she emptied herself, examining her pussy as she did. Her lips were red and slightly puffy, extending out from her labia. She had noticed on past occasions that they had begun to look like that after Randy had fucked her good and hard. She smiled to herself at the pounding she was taking this week. It was exactly what she wanted.

When she finished, she washed the plug with warm water and took time to examine it further. She saw that it was teardrop shaped and widened to about two inches with a one-inch shaft before the large blue sapphire embedded in the flared base. The stone was beautiful and radiated the artificial light from the bathroom fixtures. She lubed it and then bent over at the waist to work it back into her ass. Once she got the tip in, she straightened a little and widened her legs to relish the feel as she slowly pressed the widest part inside. Her body shuddered with delight when it seated, and her anal muscles pulled the gem tight to her asshole.

She dressed in a black thong, sage green shorts, a loose-fitting yellow t-shirt and then skipped her way to the kitchen, delighted in the feel of the plug in her ass.

Randy was placing a platter of pancakes on the table in the nook as she skipped up to his side and lightly bit his ear, her hand rubbing his crotch. "Can this be a sex hike and we fuck out in the woods?"

"Ah, no. Now sit and eat," and he nodded toward her chair.

Halley mock-pouted but did as instructed and he retrieved two glasses of orange juice and sat himself, pointedly looking at her as he reminded, "You know that shit don't work with me, now eat."

They poured syrup on the large, buttermilk pancakes and he inquired of the eighteen-year-old, "Did you put the plug back in?"

"I did. Is it mine to keep or do I have to give it back for you to use on some other slut?"

Randy cut into a sausage link and put a piece in to his mouth, replying as he chewed, "I haven't decided yet. If I let you keep it, you must be careful with it. That's about $15,000 in your ass."

Halley almost choked on her orange juice, slapping her own chest with one hand while sitting her glass down, "Oh my god, are you serious?"

"Yep. That was just the cost of the stone, it cost another five thousand to get it custom made; so, you might see why I would be reluctant to let it out of the house."

Halley shook her head, "That's okay, I don't want it. I'll just use it when I'm here."

Randy nodded and shifted the subject, "I bought you some light hiking boots and socks, so you won't mess up your sneakers on our little jaunt."

"How'd you know my size?" she cocked her head.

He smiled, "Well, I've collected your discarded clothes several times over the last few months, so I've had every opportunity to check the size of everything. But the boots are all I've bought you. I wouldn't dream of imposing a style on you, so I'll let you choose your own clothes. I just knew you would never buy hiking boots, so I intervened on that."

Halley took a bite, "You could buy me clothes if you wanted. Might be interesting to see what you'd pick out," and she snickered before taking another bite.

He began to cut more of his pancake into pieces and ticked off his wardrobe thoughts, "You wouldn't like some of it. No jeans with holes or rips or tears. None of those clogs or other ugly ass shoes. Nothing that looks like it was thrown away and reclaimed from the trash," and he paused. When Halley didn't react, he continued, "You couldn't wear some of what I would buy around your family, it would raise suspicions. There'd be stripper heels, fuck-me boots, ankle boots, mini-skirts and dresses, sundresses, halter tops and dresses, and that's just off the top of my head. To me Halley, you exude sex and I'd want to show it off."

She blushed and set her fork down, "Stop. If you keep going, I'm going to fuck you here on the table," and he shrugged.

"Do you really believe that?" she asked.

"Halley, you have no idea how sexy you are. That was one of the first things I told you when I walked in on you and Brandon back in April. You tried to cover up and I told you don't. Do you remember that?"

"Yes. I thought you were just trying to embarrass me," she demurred.

"No Halley, you are beautiful, and you don't hide beautiful, you show it off."

She wordlessly got up, took her plate to the sink, and then returned to sit crossways on his lap and embrace him about the shoulders, "I was born thirty years too late."

"Don't lament what could never be, take advantage of what exists," and he kissed her as he felt the plug in her ass with his hand. "By the way, just so there are no misunderstandings, what I said about wardrobe? That is what I think and what I like. You wear what you like, it's your body."

"Like the tats and piercings?"

"Like the tats and piercings," and he lightly slapped her ass and rubbed the plug. "Now, let me show you my property."

She got up from his lap and followed him to the bar area where there was a large shoebox and a pair of light brown, woolen socks.

"Put these on, they'll be better for your feet," and he handed her the items. The boots were light brown in color and lightweight and as she finished tying them, she stood and admired his gift.

"I like 'em. They aren't as heavy as I thought they would be."

"They'd better not be," he observed.

Halley thought the boots expensive, but his comment confirmed it and she didn't want to know how much. She curtsied, "I am ready for our walk."

Shaking his head with a smile, he reached into a cabinet behind the bar and brought out a semi-automatic pistol in a holster and attached it to his belt on the right.

"Do you always carry?" she asked as she watched.

"Every time I leave the house. You never know what you might run into out there, animal or man. I used to trust people until they proved themselves to be a liar, but now, since the money, I can't afford to just trust people I don't know. The sad thing is, some of the folks I do know, what I know best about them is not to trust them."

"Do you trust me?" she asked in a soft voice.

"Implicitly, if I didn't, you wouldn't be here right now," and he half-bowed to her and extended his arm toward the back door.

Randy followed Halley out to the breezeway, and he directed her left toward the back side of the garage. Once they had cleared the pavilion, on their right was a large staircase landing with sturdy wooden steps that led down. It was wide enough that they could descend toward the river side-by-side and he pointed left as they did so, "The property runs for a half mile that way, all wooded. It extends for another mile inland from the riverbank and," Randy pointed downriver to their right, "it goes for another half-mile in that direction."

"Geez, isn't that kinda big?"

"Just over 640 acres, but it's all wooded except for the part right around the house."

When they reached the bottom, they walked on a dirt path along the riverbank to the posted sign at the boundary of his property. He pointed out various things in nature to her, things Halley would miss entirely if she were alone; but otherwise they walked silently. As they headed back, she entwined her hand in his and walked close to him.

The climb back up the steps was more difficult than the descent and they both were winded when they got to the top. Halley stopped and put her hands on her knees, slowly regaining her breath. "You do that every day?"

"Almost," Randy was winded as well, just not as much, "depends on the weather. Walking is my backup way to stay in shape."

"What's the main way?" she inquired.

"Fucking."

Halley laughed with him and asked, "How high is the cliff?"

"Exactly seventy-seven feet, about a fourth of a football field; but it's not a cliff. It's a bluff.

Having regained her breathing she looked at him, "There's a difference?"

Randy smiled, "Yes. A cliff is straight up, all but vertical and it's usually all rock. While there is rock at the bottom here, this is a bluff as it doesn't fall off vertically and it's not made entirely of rock, it has soil and vegetation."

She nodded and followed as he started off, leading her through the breezeway and out onto the pool deck. Randy began to undress, and Halley took her cue and shimmied out of her clothes as well, "We goin' swimming?"

"I thought it'd help to cool off," and he noticed the puffy lips of her pussy.

Noticing his stare, Halley reached down to put the fingers of each hand alongside her pussy lips and squeeze them out and then looked back to him, "They always look like that after you fuck the shit out of me a couple of times."

"Well we've fucked a couple of times this week."

"Ya think?" and she turned and dived into the pool, swimming toward the far end; Randy carefully laid the pistol on the deck and then chased after her. Halley had a swimmer's body and beat him easily.

Waiting for him in the deep end, she turned to face him and placed her elbows up on the edge of the pool and splashed him with her feet as he arrived. Randy dove to avoid her onslaught and swam up between her legs as she laughed, and he kissed her deeply before backing away. He let her body float as she supported herself with her elbows and began to eat her pussy roughly while holding her ass in his hands and locking eyes with her. Halley wanted to play and did her best to resist, a determined look on her face; but when Randy began to tap on the sapphire end of the plug in her ass, she lost it and her ragged breathing gave her away.

Suddenly, he disengaged and backstroked back to the other end of the pool and she stretched her neck and yelled at him, "Asshole!"

Randy laughed as he got out of the water and went to the shower to wash off. Eventually she joined him and once they had the chlorine off, he took her hand, grabbed their discarded items and led her inside to the playroom.

Sometime during the day, he had setup the Sybian with a wooden device behind it. The device was made of two 8x8 wooden beams in the shape of an upside-down L and the top beam had a metal pipe hanging from it that extended horizontal to the floor. The open end of the top beam hung over the Sybian.

"Do you remember your first time riding this?" he asked her.

"Yes, but it didn't have the wooden thing or a dildo on it then," she observed, looking at the six-inch phallus on the Sybian's seat while she wrung her wet hair.

"Ha. No, it didn't. This is another idea from a sex site online. Go ahead and hop aboard," and he leered at her.

Without hesitation, Halley went to her knees and backed herself over the machine and Randy guided her arms over the pipe so that they caught her at the elbows. The end of the horizontal wooden beam matched the height of her head so that it would keep her upright on the machine. He handcuffed her hands so that she was stuck as she seated herself on the dildo with a gasp.

"Oh com'on. It's only an inch wide. If you're gonna gasp about it, wait until I turn it on," he told her as he attached cuffs to her ankles and then attached them to the back of the Sybian's base with clips, her shins flat on the floor.

He stepped back to take her in, and she was beautiful strapped and locked into position. Her hips were slightly forward of her shoulders, putting an arch in her back. The position of her arms forced the lower half of her head and her neck back against the blunt end of the wooden beam and she had nowhere to go. He reached down and flipped the switch and the low hum of the Sybian started.

"Mmmm," Halley cooed as she looked down toward her crotch.

Randy let her relish it for about thirty seconds before he pointedly held the dial in front of her and turned it up to full blast.

"Uh, uh, uh, oh my goddddd," and her voice vibrated in time to the machine as she cried out. The cries turned to a low, vibrated "Ahhhh" as she focused on the feelings in her pussy and her ass.

The Sybian was causing the butt plug to vibrate as well and the two were working in concert on her sex as she leaned her head and shoulders back into the beam and pipe with eyes closed and mouth open.

Unnoticed, Randy placed two wooden boxes to either side of her and stood on them, his feet close enough to her that he could place the head of his cock on her lower lip. Halley stuck her tongue out and he pushed himself into her mouth and slowly started to enter her throat. He leaned over her head and placed his hands on the beam as he began to pump into her gullet, the sounds of her gulping rising above the sound of the Sybian. She worked her lower jaw to accommodate him as he steadily pushed deeper into her throat and then he began to hold himself inside her for seconds before relenting. Each time he paused just a little bit longer before backing off and allowing her to breathe in air through her mouth. As the pauses lengthened, Halley began to work her lips and jaws to try to create space to suck in air, but it was difficult with his cock filling her throat.

She knew what he was doing, and she loved it. This breath-play thing was new, and she had only briefly experienced it in some of their earlier encounters. But it was something that heightened the feelings that came from her sex and she wanted more of it.

It was then that Randy moved his hands to Halley's wet hair at the front of her head and gripped it in both hands to force her head back into the beam. He began to lengthen the pauses even more until all except the last two inches were down her throat and then he would hold it and wait for her to start squirming before he relented.

Large strings of mucus and saliva came out of her mouth along with his cock each time he withdrew. The strings coated her chin and began to trundle down in thick, bubbled cords to her stomach and thighs.

Halley knew she was close to cumming, she could feel it as it welled up from her pussy and spread in her abdomen. Her body began to shake as Randy held his cock deep and she struggled for air; the struggling more intense as her oxygen lessened and her orgasm hit.

He backed off, all the way out of her mouth and held his cock in her face as she struggled to suck in big gulps of air and continued to cum. He barely let her recover before he forced his dick back into her throat to the hilt and she immediately began to climb to another climax, this one taking only half as long to arrive. Randy looked down past her face to see her tits jiggle as she bounced on the Sybian when she came, her mouth working feverishly to draw in some bit of air and her hands flailing helplessly, until he relented and stepped back off the boxes.

Halley's thighs squeezed the saddle of the machine tightly and her head immediately dropped and hung down, the mucus and saliva stringing from her open mouth as she wailed and shook. When she began to quiet, he reached and shut the machine off. She continued to gulp air, her chest heaving but just before she recovered completely, he reset the pattern on the Sybian and again switched to on to full song as he stepped back on the boxes.

Her head rose on its own, her mouth in the perfect O as the vibrations in the new pattern hit her. Her body tried to rise off the saddle but was stuck by the bondage and he took her head again in his hands and slid his cock into her completely before she had the chance to fill her lungs with air.

Over and over the process repeated as the minutes ticked by, until Randy had wrung five more orgasms from her body. After the seventh one, when he cut the power to her loins, she breathlessly begged him, "Please fuck me."

"Yes ma'am," and he unclasped the links that held her ankles tight to the Sybian. He then unlocked one cuff on her handcuffs and helped her to stand, wobblily though she was, "Looks like you might need some help," and he led her a few feet away as he re-cuffed the bare wrist.

Working quickly, he attached the cuffs to a cable and hit the winch button to raise her arms just to the point she did not have to bend over. He then attached a spreader bar to her ankle cuffs and extended it until her feet were four feet apart, the furthest he had ever spread her.

"Oh god," Halley responded as he hit the switch again, tipping her body over as her arms rose and stopping only when her back was parallel to the floor.

He immediately stepped in behind her and rubbed her red pussy, the lips swollen, gaping and moist with her juices. He let his hand jiggle the plug in her ass and she hissed and flexed her knees, letting her ass beg for his cock. He obliged her and filled her completely in one motion, grabbing her hips and pulling her back into him, plugging her pussy with hard and fast thrusts.

After several minutes of pounding her, her head dangling from her shoulders he told her as he worked her cunt, "You know, this is becoming my favorite position to fuck you," and he emphasized each word with a hard stroke, Halley grunting loudly in reply.

The build-up of the day had him ready to explode and even though she had already cum over a half-dozen times, Halley felt the well of passion building again. Between his cock and the plug in her ass she was filled to the brim, the heat in her body at the boiling point.