A Randy Retirement Pt. 03: 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: Teen blonde caught with boyfriend by her step-uncle, who reveals the inner self of both.

April, 2016 - River House

It had been an unusually cold and snowy winter and five months since Randy's dalliance with Persia (see previous story). He despised cold weather and thought snow was great, for five minutes, and then it became a hemorrhoid. The combination of that and the five-month dry spell after his libido had resurfaced had Randy in a foul mood all winter, not to mention he had turned 54. But now the days had started to noticeably grow longer and warmer; the sap rising in the trees and in him as well.

He was at his brother's house, having volunteered to mow his grass while he was out of town for a week. Randy got there around mid-morning and had parked behind the outbuilding in the back where his brother kept the mower. It was a large yard, but it was a warm April morning and he didn't mind the solitude as it took about two hours to mow the entire acreage.

Once the task was completed, he brought the mower back behind the outbuilding to wash it off. As he was finishing up, he heard a vehicle drive up. Knowing that no one was supposed to be there, he placed his hand on the gun at his back and peeked around the corner of the building.

He relaxed as he recognized Halley, his brother's granddaughter. Well, not really his granddaughter, at least not by blood. His brother had two sons by his first marriage, was on his second marriage and that wife came with two children of her own, a boy and a girl. They had all grown and had their own families. Halley was the oldest daughter of the wife's son and Randy had always thought that she would grow up to be a good-looking woman and she was blossoming into one as a high school senior.

Then another car pulled up and Randy recognized her boyfriend, Brandon, and it dawned on him, 'They're skipping school, wonder what they think they're gonna do.' He smiled internally as he decided to give them ten minutes and then walk in on them.

They were less than two months from graduation and both 18. Halley was at least 5'10" with long, toned legs and a nice, round ass for a tall and lean girl. She had long wheat-straw blonde hair and a slight freckling of her fair skin. He had met the short-haired blonde boy a few times at family get-togethers and had always wondered if the boy was gay. The pair did not match in Randy's view, something about it just did not click, but he had tried to write it off as just their looks, because Brandon was several inches shorter than Halley. He came from a well-to-do family with lots of money, so maybe that was the attraction for her. Randy had wondered what the attraction was for Brandon. There were rumors the dad was gay or bi-sexual and in truth, Randy suspected the son was the former and Halley was his cover or maybe the boy just didn't want to admit he was gay.

He put the lawnmower up and locked the barn door, washed his hands off and put the firearm in his SUV. Checking his watch, he saw that he needed to give them a few more minutes to get into whatever trouble they were intending, so he lit a cigarette and bided his time.

When he made his way into the house, he heard them being less than discreet in one of the spare bedrooms. They had intended to shut the door, but had left it cracked an inch and he stood back from it and observed Halley, naked and on her knees, attempting to service the boy's dick. She barely had the head in her mouth, which almost made Randy laugh because the boy was not well-endowed, and she was stroking him with only her thumb and forefinger.

Of course, it was the first time Randy had seen her naked. It was all he could do not to whistle as he estimated that she must carry around 125 pounds on her tall frame and that it probably measured about 32-25-36 with a solid B-cup. Her areolas were of the puffy type, standing out a half-inch from her rounded breast; not quite as big as a silver dollar, but with a defined, hard nipple that stood erect.

'Must be from the air conditioning because it ain't from the heat,' he mused to himself as he continued to watch and noted her pussy had a fine-haired yellow bush that he could tell had never been trimmed.

It was at this time that an idea struck Randy and he considered the implications of it for a moment or two. He dismissed the incest aspect out of hand since they were not blood kin. The clincher for him was the small spasm that he felt in his work pants and he turned to walk silently down the hall to the master bedroom. This was where the video security system was located.

He ran back the hard-drive storage video and watched them as they had entered the house. The recording clearly showed them kissing and undressing as they fumbled embarrassingly with foreplay on the couch. It was enough evidence to get them in loads of trouble however and he took a blank memory stick from a package there and made a copy of the video, all the way up to the point they had walked naked to the spare bedroom where there was no camera.

He pocketed the stick and then erased the clip from the main memory, back to the point before both their cars pulled into the driveway. He knew this system did not send alerts by phone or email when someone entered the house, so now he would be the only other person, besides the two high school seniors, who knew what had taken place here today.

It was time to spring the trap on the young lovers. He had to play this exactly right and if he succeeded, he might just kill two birds with one stone. Again, he peered through the crack and saw Brandon as he was half-on and half-off the bed and attempting put his semi-erect penis into Halley as she lay back on the bed., her legs flat on the sheets. He shook his head in ire. He wasn't necessarily mad because Brandon was attempting to fuck her, he was mad because Brandon didn't know what the hell he was doing. He strongly suspected the boy was gay and lying to himself, using Halley to cover up his inner urges. As a result, the attempt at lovemaking was as weak as the attempt at foreplay had been. Hell, he had even seen on the video he just watched that they had bumped their front teeth as they attempted to kiss.

In a smoldering rage, Randy banged the bedroom door open and caught it before it slammed into the wall and the doorknob put a hole in the sheetrock.

As he did, he all but yelled in a loud voice, "What the hell do you think you are doing?"

Brandon fell backward onto the floor and scrambled to the far wall in a reverse crabwalk to get away from the intruder, while Halley just stared, her eyes wide, the blush rising in her cheeks.

The blonde boy was the first to speak, "We, we were on our, our lunch break from school, we have open lunch and we were, well, we were," and Randy cut him off with a menacing stare.

Out of the corner of his eye he saw that Halley was trying to cover up with the sheet of the bed and he turned to her, "NO! Do not cover your body. I have already seen you anyway. So have the security cameras. All this is on video," and he pointed to each of them, "both of you, naked."

She turned to the boy, "Oops, I forgot about that," and Brandon tried to sink his head further between his knees. He was trying to figure a way out of this. This man standing over them had always intimidated the crap out of him and Brandon did not want anything to do with him in the least.

Halley on the other hand was mortified with embarrassment and on the verge of crying, which was rare for her as she hardly ever cried. She had always been determined to be the one that others could turn to in a crisis and this was quickly devolving into one. Unaware she began to pull the sheets to cover herself again.

Randy reached down and ripped the sheets from her hands. "What did I tell you? No covering up!" and he knew it was time to begin his gambit. He ignored the boy and bore his eyes into Halley as he spoke.

"Do not ever cover your body around me again. You have a beautiful body, but you need to learn how to use it. You're so damn sexy and you don't even know it. If you had the confidence, then you'd have the control. Trust is earned and is not to be given easily," and he pointed to the boy, "A male will tell any lie, assumed any trait, endure any thing to achieve getting in your pants," and he paused. Tilting his head toward Brandon, he continued, "On the other hand, some will fake any interest in order to prove to the world, and themselves, that they aren't gay."

"He's not gay," and "I'm not gay," were spoken in unison from separate sides of the room.

Randy put his hands on his hips and smirked, "We shall see, until then, keep telling yourselves that. Now I'm going to tell you what the score is here. I erased the part of the surveillance video that has you both on it. Only us three will ever know what happened here today."

Both teenagers chimed in with, "Thank you," thinking they were off the hook.

Randy held up a finger, "But. It's time you learned a life lesson. Actions have consequences and most of the time, when you think you are getting a break in life, there is a catch."

Brandon spoke first, "We'll do anything, just don't get us in trouble please."

Halley was more wary, "What's the catch?"

Randy produced the memory stick from his pocket and held it up for them to see, "I made a copy of the video. It is the only copy. You have two options. A, I send this to each of your parents and grandparents and anyone else I can think of as well as posting it anonymously on some porn sites; or B, you can let me teach you about sex properly by following me to my house in your individual cars and once there you do whatever I tell you." He had emphasized the 'whatever.'

They looked at each other, but did not speak. After a moment, Halley looked back to Randy, "Can we have some time to talk amongst ourselves?"

Randy made a point to look at his watch, "You have two minutes," and he shook the memory stick in the air before depositing it in his pocket and going out into the hall.

Brandon did not want to go. His reasoning was that they could weather any fallout and deal with any blow to their reputations, that their parents would turn against the man. Halley was intrigued by one word that Randy had said, 'Teach.' She did not tell Brandon this however, only arguing that they should not have been here in the first place and that she could not bear the strain that this would cause if it became known to her family.

"Besides Brandon, if this got out, I don't see how you and I could continue," she told him. That was enough for Brandon to reluctantly agree and Halley called to her acquired great step-uncle. "We've decided."

Randy re-entered the room and Halley began to tell him that they would go to his house, but he interrupted her, "I heard."

She looked at him incredulously, "I can't believe you were listening!"

He looked at her and stated flatly, "Halley, I am always listening, and watching, and observing, and processing. It's what I do. I do it even when I'm not trying to do it. Now, get dressed and straighten up that bed."

Once they had all reassembled in the living room, he looked to each of them and told them, "Just follow me. Don't turn off and don't go the other way. If you do, the deal is off, and I get on the computer as soon as I get home. Got it?" and they both nodded. "Say it."

In unison they both verbally acknowledged that they did, indeed, 'get it' and the caravan to Randy's river house began.

As Halley drove, she had to concentrate to keep her hands from shaking and to keep the car on the road. She and Brandon had fucked before a couple of times, but it had never been the experience that she had thought it would be. She had lost her virginity to one other boy before Brandon, but he had been even more clumsy in his efforts. Her mind however was trying to anticipate what was going to happen when they got to Randy's house.

'Is he going to show us the video and point out what we did wrong?'

'Is he going to instruct us on how to fuck?'

'By putting his hands on us?'

'Is he going to try to fuck me to show Brandon how to do it?'

She kept going over each of these as she drove, the thoughts eliciting a twinge of electricity deep inside of her that she had felt before, but nothing had ever come of it; a twinge being all that it had amounted to and as disappointing as her sex history. She was nervous and scared of the situation and of this new feeling deep down inside.

Brandon, however, was stuck on one single thought. He kept repeating silently to himself as he drove,

'I'm not gay.'

'I'm not gay.'

'I am not, gay.'

By the time they arrived, they were both keyed up and tense, Halley intrigued by the prospect of sex. Brandon intent on proving he was not gay.

Randy parked in the garage and directed them where to park their cars in front of the house. He made sure that Brandon's was parked in such a way that he could leave without Halley having to move her car. He then brought them in through the garage and turned them immediately into the elevator on the right, taking them to the second floor.

Turning left down a short corridor, he flipped the switch to open the sliding doors of his playroom and pushed them inside.

Once they were in, Randy pointed to Halley, "Strip. NOW!" and then to the boyfriend, "what are you waiting for?"

As they reluctantly began removing their clothes, he went to a cabinet and started his recording system. Everything in his house was now being recording in HD. He also plugged in the recording from his brother's house.

There were eight giant flat screens all around the walls and they all lit up with the pair's earlier futile attempt at lovemaking.

The presentation caused them to hasten in the removal of their clothes. As she removed her jeans with trembling hands, Halley began to look at anything else but the screens and found herself mesmerized by all the equipment in the room, she had no idea what many of the things were for and she slowly turned in a circle to take it all in, in the process unaware of what was occurring to her boyfriend.

Randy had directed the blonde boy to a bondage bench with two upright pipes on one end about four feet apart, "Lay on your back there." The young man hesitated, but then obliged when Randy pointed at the video. Brandon promptly had his wrists bound together with handcuffs, which were tied off above his head. Randy then put bondage cuffs around the boy's ankles and attached the cuffs to the top of the pipes, leaving Brandon's legs splayed up and out at a 45-degree angle and his ass hanging off the end of the bench. "I'll be back for you in a minute."

The boy started to protest, but as the first syllable came out a look was all it took, just one look, to make the rest of his words melt away.

Going to Halley, he gently led her to a Sybian that was 10 feet to the side of her boyfriend's bench.

"Sit." He told her.

She gave him a look of trepidation, she was as scared as at any point in her life. He pointedly looked at the nearest flat screen. There she was licking her boyfriend's flaccid cock. Her cheeks burned red as she slowly lowered herself on the nubbed, flattop attachment of the Sybian.

He checked to see that she was seated properly and noted something about her pussy, despite her bushy pubic hair, that he made a mental note to check later. Then he attached cuffs to her ankles and clipped them to the back of the machine, giving her a slight forward lean and placing her clit against the nubs. He handcuffed her hands behind her back and attached the handcuffs to the rear of the Sybian to keep her from falling forward.

Stepping back, he turned the power on and started an automated program that was attached to the control box that would get her hot, but power down so as not to let her climax.

Halley closed her eyes as the vibrating sensation began to take her and he leaned down and whispered in her ear, "Watch and see who your boyfriend really is while you enjoy your ride."

Going back to the cabinet, he got a rubber cock-ring, a bottle of lube and a large, vibrating anal plug; the kind with a rounded point that leads to a larger rounded bulb, and then a smaller shaft and a retainer disc to keep it from slipping completely in an ass.

The boy was intently watching Halley rock on the Sybian and didn't notice Randy kneeling between his legs until he felt the cold wetness of the lube on his cock.

"You see Brandon, you've been going about this all wrong," Randy said as he began to play with and manipulate the young man's cock.

The boy's head snapped to his groin and he let out a gasp. He watched as the man, gently at first and then more forcefully, began to stroke his dick with one hand and twist his forefinger and thumb around the helmet.

"Deep down inside you know that you are just like your dad ... same DNA, raised in his home, so you get the urge to be a cock slut from nature and from nurture," and as the man said this he began to squeeze the base of the boy's cock and pull up while he used the thumb of his other hand to massage the boy's frenulum.

A moan escaped from Brandon's lips as he let his head collapse back to the bench and began to try to extend his hips up into the man's hand. His cock had now engorged until it was past five inches in length and Brandon had never felt like this before. His mind was working overtime on his mantra of 'I'm not gay' but his body was losing the battle as it responded to the man's hands. He had always had doubts, always wondered why he didn't feel the urges that other guys seemed to have about girls. He tried to suppress the urge that was building inside when the man began speaking again.

"Have you ever cum Brandon? I don't mean a little spurt; I mean really shot off."

At first Brandon fought hard not to become excited by this man's hands. He kept telling himself that he did not like the situation he found himself in and that he was not happy in the least being masturbated by another male. But his penis and his balls and the fire in his loins were yelling 'Liar!' at him repeatedly as they urged him to give in to the man. They wanted to cum badly.

A moan from Halley interrupted the man and he looked over to see her rocking to try to get her clit off the nubs, but the strain on her ankles, thighs and calves just caused her to have to lean forward again. Her eyes were open, but far away, and her mouth was open as well with soft moans and pants escaping at regular intervals.

Randy's attention came back to the boy, who had begun to surrender. His ministrations were winning the battle and Brandon was attempting to speak, "Ca, can, can I, cum sir?"

The man smiled at the boy, "Sir? You learn quickly. We'll see how quickly in time. Oh, and you'll cum alright, you just have to figure out how to make it happen," and with that he redoubled his effort until, sensing that a moaning Brandon was about to orgasm, he stopped. Dead stop.

"Plea, please. Don't stop," Brandon pleaded. He felt the need to cum as he never had before in his young life. His cock had never felt this way before, and it was at the hands of another man. His mind stopped telling him that he wasn't gay. He wanted this man to make him cum.