A Randy Retirement Pt. 03: Halley

"That didn't take long, I always knew you were a cock slut, boy."

Randy reached down and picked up the cock-ring, stretched it in his hands and slipped it over the boy's cock and balls, so that it forced the shaft to stand straight up in salute, "Arrggghhh," the boy strained in his bondage.

"Deal with that and think about what you really want. I'll be back in a minute."

Smiling, Randy wiped the lube from his hands on a towel and walked over to Halley. Her mouth and her eyes were now closed, and she seemed to be concentrating. He reached down and tweaked a nipple, gaining a yelp from her, but no other reaction as he massaged her breast.

"Enjoy it Halley, there's much more to come."

It was then that the machine changed programs, and a heartier buzz came as it kicked up a notch. Halley wiggled her ass on it and started cooing.

Sighing at having to leave her, Randy went back and knelt between Brandon's legs. He reached out and flicked the blonde's erect cock with his forefinger.

"Ahhhh," came the guttural response from the boy, "Please, please sir, make me cum."

"You know who you are Brandon, and you know what you want. You've always known, but you've suppressed it. Time to commit boy. No more using girls to hide it. Let's get this out of the way so you can hit the road and I can show Halley how things are done in a proper manner."

And with that, lubing his hands again, he resumed edging the boy, stroking his thin, five-inch, rock hard cock that fit easily in one of his hands.

"Plea, please let me cum!" the boy cried, and the man stopped again; the boy's hips still humping air as he removed his hand.

He stood and looked down on the writhing eighteen-year-old, "Look at me," and the blonde raised his head. Tapping the head of the boy's cock with a finger on each word he said, "You. Know. What. You. Want." And taking the rod in his closed fist, thumb, and forefinger down, he squeezed with each word, "All. You. Have. To. Do. Is. Admit. What. You. Are. And. Ask. For. It." With the last word he squeezed hard and held it, drawing a squeal from his subject.

Letting go, he knelt again and continued the edging with one hand, while using the lube on the other to slicken up the boy's puckered asshole, "I bet when you jack-off it never lasts more than two minutes, does it Brandon?"

The boy felt the man's fingers enter him. Sometimes Brandon had played with his asshole and scared himself because he had enjoyed. He was not scared now and began bucking his hips again to get any kind of friction in his aching member. He spit out the answer to Randy's question haltingly, "N-no. It. Doesn't. Last, ahhhh, long!"

Satisfied, the man began masturbating the boy faster, "That's because you are thinking about the wrongs things while you jack-off, but you know that, don't you?"

"Ahhh, yes, oh god yes," and as the man stopped cold once again,

"Ohhh, SHIT! Please sir, please make me cum."

"Brandon. Brandon, LOOK AT ME!" and the boy complied, breathing heavily.

A deep sigh emitted from the side as Halley was no longer trying to avoid the nubs and was instead grinding down on them in a futile effort to get herself off.

Turning back to the boy, "What are you Brandon? Go ahead and announce it to Halley and me. What are you boy?"

"I'm gay sir," the boy cried out in his desire for release.

"Good boy. Now that we got that outta the way, how 'bout you tell me what you want? You know what it is you want, all you have to do Brandon, is ask for it."

In that moment, the blonde boy's eyes focused, he set his jaw and a resolve of acceptance came over his face, "Can I please suck your cock sir?"

With that, the man began again to edge the boy while picking up the anal plug and pressing it to the boy's asshole.

"Ahhh! What? No. NO!" the boy cried, but Randy was unhearing.

He continued to push, while edging the blonde boy, the very tip of the conical sphere entering his rectum, "Are you sure? This is what you want, isn't it Brandon?" and the first inch and a half slipped in.

The boy cried out as his rectal muscles tightened harder when another inch pressed inside him, "Please stop. Oh I need to cum. Please let me suck your dick."

The man pushed firmly and then relaxed the pressure on the boy's asshole. As soon as the blonde relaxed his resistance, the man pressed firmly with the heel of his hand and the boy's asshole expanded and swallowed the plug to the hilt with a wet sound.

"Ahhh. It's too big, take it out, take it out!"

"Na, Brandon, that stays in. Get used to it, 'cause someday, some daddy is gonna put his big cock up that ass and you are going to love it."

The boy tensed again, almost ready to cum and the man stopped his stroking, causing an anguished sigh. He rose and went to the head of the bench, released the boy's wrists, but re-cuffed them behind the back as he sat the boy up on the bench. "We don't want any diddling while you are getting your request."

He unclipped Brandon's ankles and had him turn on the bench to face Halley while he removed his own clothes. Brandon fidgeted watching his girlfriend grind on the saddle of the Sybian, her eyes open for just a moment every few seconds or so, but she did not acknowledge him. He realized he felt no sexual urge watching her naked body as she writhed ten feet from him. His only sexual urges were focused on the feeling of his ass being stretched and his need to cum.

Halley was lost in her own world, trying to scratch the itch that was growing in her loins. And every time she thought she was getting close, the damn machine stopped. It was like there was something wonderful and fascinating that was just over the top of a hill and every time she got close to the top, she lost ground and slid back down and had to start over. The frustration of not being able to get over that hump, not being able to scratch that itch was driving her on and on in her efforts. She did not want to stop until she found out what was on the other side.

When the man came back to the bench, he positioned the boy so that Halley had a side view of his first attempt at a blowjob.

"Ok, boy, you've always knew this was your destiny, no matter how hard you tried to deny it to yourself," the man said, drawing Brandon's attention to what was in front of him. At least nine inches long, maybe more, and a good two inches wide, it was the biggest cock he had ever seen in his young life.

With his hands cuffed behind his back Brandon rose off his haunches without being told and took the head into his mouth, working his tongue around the underside of the thick shaft. It was big and he had to work it in using only his mouth and neck to position himself, but he was determined.

The man reached down behind the blonde's back and switched on the vibrator, causing the boy to jump, but not lose contact with the cock in his mouth.

The sensation on Brandon's prostate was so wonderful he started moaning around the man's cock as he took in another two inches.

"Not bad boy, you're a natural at this," the man commented as he stood there, hands behind his back and letting the boy do all the work. "Halley," he called. "HALLEY!!" The high-schooler's eyes flew open and she took in the sight just in front of her. "You see, this was the problem Halley. It wasn't you. It's just that, deep down, Brandon was born to be a cock-sucking whore," and with that Brandon engulfed another inch and moaned around it. "See, he admits it."

Brandon did not understand. This felt right to him. This cock was so huge, yet he immediately had felt the urge to suck it. Maybe indeed the man was right, he was gay after all.

Randy then spoke to the boy, "Ahh, you're a good little cock slut. I knew you were the first time I met you. Now, a little faster, make love to my cock with your mouth," and the man placed a hand behind the boy's head and gave him a quicker tempo. Randy then put his other hand on the boy's head and begun to guide additional inches into his mouth, hitting that spot in the back of the boy's throat where the gag reflex usually kicked in, but nothing happened. The blonde just continued to suck and with each stroke, the monster cock went down a little further while the man's hands let it come back out a little less.

When the boy had taken in all but the very last of his cock, the man, removed his hands and looked down at him, "Damn boy, a deep throater with no gag reflex. You play your cards right and you could make a ton o' money in the right places."

With this the boy began to long stroke the man's cock with his mouth, going all the way down to the root and backing off to the head.

Back and forth.

Back and forth.

Faster and faster.

The man looked at Halley, whose eyes were open, and hips were grinding, her face a picture of frustration at the elusive orgasm.

"Take notes Halley. He is good for something. You're going to be doing this before you leave today," and with that they locked eyes and neither looked away from each other as a sense of lust passed between them.

Halley's apprehension and fear had faded to the background as acquiring whatever it was out there just out of reach had taken over the forefront of her clouded thoughts. Even though seeing what was in front of her, it did not register consciously in her mind as she was preoccupied with the feelings in her pussy.

If she had been aware, she would have seen Randy's hips tense as Brandon continued to work the cock with his mouth. Brandon sensed that something was about to change, but he had no idea what to do, so just he took the man's cock in as deeply as he could and held it there. As the sperm started to come, the boy backed off, with his mouth wide, and the man with his eyes still locked with Halley's, took hold of his cock, and directed most of his load toward the boy's waiting mouth. Brandon thought it tasted wonderful, the saltiness of the sperm on his tongue satisfying an urge that he had never been able to quench. 'Who knew!' he thought to himself.

When he was spent, the man removed his hand, "Clean it up now like a good little whore," and the boy eagerly slurped all the excess cum off the man's cock.

When he had finished, the man went behind him and removed the cuffs, turned the vibrator to high, and pointed at the bench, "Like I said, you have a future. Sit there and face Halley and get yourself off."

Brandon began to stroke his own cock, slowly at first, while the man walked to the Sybian control box and bypassed the computer program, turning the dial to max. Halley's eyes screwed shut tight and her mouth formed an "O" as the sensations on her clit and pussy lips caused the endorphins to light up her brain.

In a matter of minutes, they were both cumming together, him with an open mouth and a look on his face intent on squeezing out the biggest cumshot of his life; her with mouth now closed and teeth gritted as she was willing herself over the edge. As Brandon shot the largest load of his life, the vibrator also dropped out of his ass and his free hand automatically went to feel the sudden void there. His cum spurted almost the entire ten feet to where Halley was rocking on the Sybian, hitting her on her thighs.

Halley had wailed as her orgasm had overcome her. It wrenched every ounce of tension from her body and brought her to a sweaty climax that was the first of her young life.

The man turned the Sybian to its lowest setting, letting Haile, breathing shallowly, ride out the afterglow of her orgasm, and turned to the blonde, panting boy, "Get your clothes and follow me." Then he turned and went out the doors to the playroom.

Brandon gathered his things and followed out into the short hallway, the man leaning against the wall there, arms crossed. Brandon couldn't take his eyes off the man's cock, still glistening with Brandon's saliva, as it hung there.

"Get dressed," the man commanded.

"Sir, you aren't going to fuck me?" the boy asked, almost pleading.

"No son, not my thing. If it hadn't been the only way to show Halley your true self, you wouldn't even have been here. Now get dressed."

While Brandon began to put his clothes on over the bodily fluids that coated his body, the man looked him in the eyes, never wavering, "I knocked down the wall you had put up so that you could see what you really are inside. Never speak of this day with anyone. Never speak to Halley again, unless it's to say hello when you pass each other. Although I erased the video at her grandad's house, I still have the copy. I also have a video of you begging to suck my cock."

At this the blonde's eyes grew wide, "Yep, that's right. Now, leave and never look back. Your future is forward, and it includes a lot of cock." The man pointed toward the spiral stairs leading down to the garage and the door and as Brandon walked by, he smacked him hard on the ass. The blonde put his hand on his ass where it burned and turned with a wanton grin on his face, "Thank you sir," and he was gone.

Returning to Halley, Randy knelt and used the towel to wipe the cum from her thighs and then unclipped her wrists and ankles. She was mumbled softly. He turned the Sybian off and stood her up, then grabbed the hair at the back of her head and turned her face toward his. "What do you want Halley?"

"Teach me," she replied with a shaky voice, not sure why she said it but intent upon it nonetheless.

*

He took her to the nearby bathroom that had a large shower, turned on the water and checked its temperature for her before ushered her in, "Soap yourself up and wash," and then planted his naked self on the toilet seat and watched.

Halley reached to close the shower door and he spoke to her firmly, "Leave it open," and she relented. As she took the shampoo and fingered it into her long hair, he lit a cigarette and took in her long, lean body. She was tight in all the right places and yet had curves in all the right places as well, not boney, and not an ounce of fat. Theirs had always been a good relationship and he had even helped her with school papers and given her advice when she started to choose a college. Even though Randy always thought she would grow into a beautiful woman, he had never considered what was in his head at that moment. He was going to give her every opportunity to back out, but at that moment he believed she would not. His intuition told him that Halley was too inquisitive to pass up this new opportunity that had inserted itself into her life.

As for Halley, she was lost in thought, not knowing how to act or how to respond.

"Is he going to rape me?'

'Is it rape if I want him to fuck me?'

'Is it incest?'

She was struck with an inherent need to explore further and as she realized this, she spotted a black rubber phallus-shaped object that was about seven inches long and attached to the shower head by a metal hose. She pointed to the attachment and asked, "Do I want to know what that is?"

He matter-of-factly told her, "It's an anal douche. You'll use it to clean yourself out before I fuck your ass," and her mouth gaped open as she looked at it while Randy continued, "but that's for another day. Are you on the pill?"

"Yes. I've been on the pill since I was 15," and she recovered her composure and continued to the question that was foremost on her mind, "If we fuck, is it incest?"

He considered the question for the second time that day and decided to test her.

"What do you think incest is?" he asked.

She looked at him, "Fucking someone you're kin to."

He nodded his head once, "That's true. But are we kin? I think the legal definition involves blood relation, while the social definition is muddled and sometimes includes even relation by marriage or adoption. But I never cared much for what society thinks. The most commonly accepted definition is to be related by blood. We are not related by blood, so no, if we fuck it is not incest."

As Halley began to wash her pussy, the hand that held the washcloth lingered and he took note as she told him, "You know, I had a dream about you when I was fifteen. Scared me to death, I thought I was going to hell. Then it dawned on me that we weren't really related."

Randy wanted to ask her about the dream, but she swiftly switched topics. "Are you bi-sexual?"

He laughed aloud and stood to flip up the seat and tap the ash off his cigarette, putting the seat down and sitting again as he replied,

"No Halley, I'm not. You witnessed the first time I have ever done anything with a male. It was just so obvious to me that Brandon is a cock-slut trapped in a male's body; that's why he didn't know how to fuck. So, I decided to show him who he really was. I am most decidedly heterosexual. A gay thought had never entered my mind until today, and today I considered a necessity to prove something to you and him. I love fucking women, but I derive my pleasure from making women orgasm and helping them to find their sexual self and in the process, maybe their real self, sexual and otherwise."

She was bent over now and washing her long legs, "How did you know Brandon was gay?"

Randy turned his palms up in front of him in a shrug, "I don't know how I knew. I can't explain it. I just get intuitions about certain people. They come of their own accord and without any effort. And they come about all sorts of things, some of them not even sexual in nature. I just knew. And he's not the first I suspected to be gay and turned out to be right about either. Matter of fact, I can't think of one that I was wrong about."

"Have you had intuitions that turned out to be true about me?" she inquired.

He smiled at her before replying, "Not intuitions really. Let's just say I have wondered to myself certain things that are yet to be determined."

Seemingly satisfied with his answer and gaining confidence she switched topics again and asked why he'd never gotten married.

"Damn girl, it's gonna be tough to keep up with you. You jump from one thing to another at the drop of a hat," and he grew silent and looked up at the ceiling for a long time. Halley half-smiled and just continued to wash herself until he was ready to reply.

He stood to throw his cigarette into the toilet, re-seated himself and started, "Of all the dreams, or goals or statuses one could realize in life, marriage was the one I wanted the most from the time I was a young teenager. Maybe that's why it didn't happen, I wanted it too much. I determined early in my life that I wasn't marrying someone just for the sake of being married. I wanted a relationship I could work at and grow for practical reasons, but I also had all these romantic reasons for it. Work and coaching kept me really busy more than it should have and I wasted a lot of years, but there was one woman, when I was in my early forties, that I really thought was the one. I had always thought I was caring and empathetic, but the relationship with her was different. With her, every decision of consequence that came up, the first thing I considered was how it would affect her and us. I changed with her. I no longer thought 'I', it became 'we'," and he paused then and lit another cigarette.

Halley turned off the shower and reached for the large towel. She stood in the shower and began to dry herself and let the activity eat up the silence. As she neared the end of her task, she asked what he knew would be the next question, "What happened?"

He laughed again, "To be honest, I don't really know. We were together for almost five years. She was half my age and just finishing up her fifth year of college and I suspect the reality of marrying an older man finally hit her; but I never really got a straight answer on it. It takes a different breed to be involved in an age gap relationship; takes someone who doesn't give a damn about society's perceived rules. When we got together just after her high school graduation, I know she thought that she didn't give a damn, but in the end, I think she came to realize the full implications of it and it scared her off. But I could be wrong. Maybe she just realized she wanted more than me. Like I said, I don't really know."