A Randy Retirement Pt. 04: Halley Ch. 02

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 revisits her step-uncle for more teaching with some bondage sex.

May, 2016 - River House

Halley was a ball of nervous energy. It had been five weeks since her encounter with her step-great uncle. They had spent an afternoon together after he had caught her and her boyfriend in a fumbling attempt at lovemaking (see previous story). The now ex-boyfriend had turned out to be gay, something the uncle had revealed to them both and then he had essentially blackmailed her into having sex with him. But Halley did not feel violated and wasn't mad at him at all.

Instead she felt curious, and intrigued, and horny. She had spent most of the first two weeks struggling with the situation, pondering what to do and how she should feel. She and the uncle were not blood-related, they were only family due to second marriages between her grandmother and his brother, so she did not feel any shame from incest. She did not mind the 36-year age difference between them because it wasn't like they were going to get married; she knew that if she decided to continue that it would be just for the fucking and in her limited experience, he certainly knew how to do that. He had said he would teach her, about sex and about herself.

The sex had been like nothing she had ever imagined and certainly not like the few times she had fucked boys her age. No, her uncle Randy's cock was huge, and he knew how to use it and how to manipulate her body to the first real orgasm of her young life.

In the third week she had decided that she would ask to go back at least one more time to visit him and she began to experiment with the dildo he had given her that she kept hidden between the mattress and box spring of her bed.

Every night she would use it to masturbate and stretch her pussy and then she would suck on the head to get used to something in her throat as well. It made her tremble and it made her feel good; but it never made her feel the way that Randy had when he fucked her.

That weekend she made a clandestine trip to a neighboring city, couldn't have anyone spot her, and made purchases there of a dozen thongs in various colors and styles even though she was nervous the entire time. She also went to a spa and got all her pubic hair removed. This was even more of an anxious experience for her, but the lady there was very professional and comforting and told Halley that with her fine hair it would probably be six weeks before it started to grow back.

During the fourth week she dug out the burner phone he had given her from its hiding place and texted him and asked if she could come over the next week and have him help her fill out her financial aid forms for college. She did not mention any other reason for wanting to visit. When he did not reply right away her anxiety pegged and she began to wonder if she had made a mistake.

She did not cry easily, but was on the verge of tears when an hour later the phone dinged, and she shook as she looked at the text.

"Sure thing. Bring all info needed & we'll get it done. Friday at 5pm."

The text ended with a smiley face and Halley's anxiety melted until she realized that Friday at 5 was a week away.

She had spent that last week in a state of simmering anxiety as she fretted about a number of things.

'Would he like her purchases and wax job?'

'Would they fuck?'

'Could he get it all the way in her?'

'Did she want him to?'

'What if he's changed his mind?'

'Would she be able to take all of him when she deep throated him this time?'

'Would he approve?'

All that continued to be on her mind as she was parking her car in his driveway. She had spent two days debating what to wear, finally settling on a white scooped neck mini-dress and sandals with a white thong underneath and no bra. For the first time ever, as she checked herself in the mirror before leaving home, she had thought she looked sexy.

Randy greeted her at the door, and they had a brief hug before he looked at the laptop in her arms and asked, "It's all online?"

"Yes," she answered.

"Well let's go in dining room and get you hooked up to the Wi-Fi and she what we've got," and he let her lead the way.

They sat at a corner of the table and after Halley had booted the laptop up, he turned it to himself and accessed his Wi-Fi. It took a little over 30 minutes to complete the process and Randy was all business. No flirting and no innuendo. Halley was becoming disconcerted, she had prepared and looked forward to this day and dressed to the nines and yet here Randy was acting like nothing had happened between them.

Closing the last of the completed forms on the screen, he looked at her and smiled, "Well, there you go, all set. You should hear back from them sometime in June."

"Thanks," Halley responded, her mouth in all but a frown.

"Something wrong Halley," he inquired.

"Yes. I," and she paused and looked down at her hands on the table and paused before diving in, "I thought you wanted me. I, I'm confused I guess."

Randy did not respond immediately, but after a moment he placed his hand on hers, "Oh baby, I do want you. But you should know that words mean things. I told you that you have to decide if you want to continue and tell me," and she opened her mouth to interrupt only to be stopped by his upheld finger.

He dug in his pocket and retrieved his phone, tapped a few keys and then turned it for her to read. It was her text to him, asking only to come over and fill out the forms. "You said nothing about wanting to continue with me. I took you at your words. Now, have you come to a decision?"

"Yes," she beamed as she said it, "I want you to teach me."

"What about Brandon?"

A smaller, pained smile creased her face, "Irrelevant, we haven't spoken since, well, since you know."

Randy opened the browser on her laptop and did a quick search, selected a picture from the search and saved it, making it the background before turning the computer back to her.

She bent her head to it and read aloud.

"Someone asked me today why I push myself when I train. I push myself to break through any perceived barriers I've unconsciously set in my own mind. To remember only I set the limit of what I am capable of. I push myself because it sends a signal to my whole body that I am alive."

When she looked back at Randy with a look of bewilderment, he told her, "I found that by accident about a week after I brought you here. It was written about exercise, about working out, but when I first read it, I substituted the words 'have sex' for 'train' and thought of you. I want you to push through any sexual barriers you have put up. I want you to understand that only you can limit what you are capable of sexually. That if you push yourself, sex will never be boring, and your body will always let you know that you are alive. That is what I would teach you Halley. But, and it's a big but, it is not about what I want. It is only about what you want."

"I'm ready," she said without flinching.

"I can tell," and he nodded at her chest.

Halley looked down and realized her nipples were hard and poking the fabric of her dress out like tent poles. She caressed them with both hands for a few moments and then laughed, telling him, "You know, a month ago I would have never dared do that, with anybody, not even alone."

He just smiled at her, "You know that I took it easy on you last time, I tend to play rough."

"I kinda figured. Took me a week before I wasn't sore the first go 'round. It's okay. I want it. I been practicing with that little gift you gave me," and she gave him a mischievous look.

"Stand up," he ordered and when she did, "Turn around." She did.

Anticipating what he wanted, she held her long blonde hair on top of her head as he unzipped her dress and let it fall from her shoulders. As Halley released her hair, he reached around and pulled her back into him by cupping and squeezing her breasts. She closed her eyes and sighed as he nuzzled her neck and let his hands drop.

"Let's see how well you've practiced," and she heard his pants unzip.

Halley twirled around and stepped out of her dress, stooping to pick it up. Randy put a hand on her head and held her there stooped over and a moment later she understood and sunk to her knees. He took the dress from her and put it on the table while she looked to find his meaty ten inches in her face as he had stepped out of his pants.

As she took hold of it by the base, Randy removed his shirt and then put his hands lightly on her head. "Go slow to start, this is gonna be harder than before because your head isn't hanging off the bed. The angle is different," and she began getting his cock wet with her tongue.

She took the head into her mouth with little effort and began to work it in and out. As she stoked the base, she took more and more into her mouth until she reached the back and then sucked hard on his penis, eliciting a sigh from Randy. The positive reinforcement had the desired effect as Halley then pushed past her gag reflex spot with a minimum of trouble, pausing only briefly to let a small retch settle and then pushing on, maintaining the suction.

She closed her eyes and dropped the hand from his shaft, placing both around his thighs and using them as leverage as she took more of him down her throat.

Randy concentrated to stand still while looking down on her. He thought of how wonderful she looked as a cockslut while he stared at her upper lip stretched over his cock. The first stirrings began in his balls then and he cursed to himself for not wearing a cockring.

When Halley had managed all but the last two inches, she held herself on his dick for a good 30 seconds, before backing off and taking a break, sitting on her butt with her legs tucked under her and tilting her head to look up at his cock as she used both hands to stroke it.

She had her mouth open in wonder and her eyes focused entirely on his cock, drool stringing from her mouth unattended. The word that came to Randy was ravenous as he watched her. He dared not speak, lest he intrude on this moment as she communed with the object of her desire.

Without preamble Halley rose from her knees and took it down her throat again, pivoting her head as she began to work it hard. In no time she was face-fucking herself and Randy closed his eyes. The liquid sounds as she forced his cock down her throat almost set him off and after a few minutes he looked at her and her eyes were open and watching him as she moved her head on and off all but the last two inches of his cock and he couldn't hold back any longer.

When she felt his first twitch, she took his cock from her mouth and directed his cumshot onto her face and chest. A string of sperm shot diagonally from above her right eye, across the bridge of her nose and onto her left cheek. Another decorated her right clavicle and down between her 32Bs with the large puffy nipples.

Randy reached down to help her to her feet and, without a word, guided her up the nearby spiral staircase to his playroom, stopping by the bathroom upstairs to grab a towel for her to clean up a little.

On the trip up the steps he admired how her ass cheeks were split by the new tiny white thong that she wore. He decided then that she deserved a spanking.

When they entered the playroom and the doors swished closed, she turned to look at him and spoke for the first time since she had hit her knees downstairs. In a raspy voice she said, "I remember that sound scaring me the first time I heard it," and she placed her hand at her throat and looked down.

"It's the blow job. Sometimes it causes a temporary rasp, unless you do it daily, then it sometimes becomes permanent. I find it sexy myself," and he smiled at her.

He led her by the hand to the small room on the back right. It held only a full-sized bed that had brass-railed head and foot boards but was special made as it was three feet longer than normal. He sat down on it and pulled Halley facedown across his lap. She laughed as he rubbed his hand on her bare ass cheeks and tugged the thong tighter into her crack, telling her "You know I should spank you for letting a sissy try'n fuck you."

Halley started to speak and was cut-off as he smacked her far ass cheek, "I, ow!!" and she sucked in air through her teeth and tried to sit up.

Randy held her in place across her back with one arm and immediately spanked her nearest cheek, bringing another vocal reaction but this time the breath she took in had a different tone; one of building heat as he rubbed the spot that had just turned red with his handprint.

He continued with this for several minutes; spank and rub, spank, and rub, and when he rubbed, he teasingly let his fingers include her asshole and the edges of her pussy lips.

Halley's ass turned quite red as his onslaught continued, hard enough to be felt, but not hard enough to bruise. Each successive strike and rub brought Halley's internal temperature up a little more. It was when he felt her wetness leak to his thigh that he knew she was ready.

He removed her thong and slid it as far down her long legs as possible and then maneuvered her to sit up on his lap and face him, caressing her breasts as he kissed her deeply.

"You're mean," she told him amid their embrace, her arms around his neck and Randy moved a hand to her mons and felt the smoothness of her skin and she sighed.

"I see you can follow directions," he told her as his forefinger found her wetness and dove in, "that bodes well, but your past indiscretion required discipline," he smiled at her as he inserted a second finger and she placed her forehead against his and held her breath.

Randy pivoted on the bed and lay her on it, taking her nearest wrist and quickly attaching a restraint that pulled it to the corner. He slid across her and did the same to her other wrist.

"Oh fuck," and she drew out the words as she laughed nervously.

He ran his fingers lightly down her arm to her side and then her leg and then walked to the foot of the bed as she eyed him fervently.

Without warning he grasped both ankles and pulled Halley's body toward the end of the bed, taking all the slack out of her wrist restraints.

"Oh fuck," she sighed again as he attached matching ankle cuffs and then pulled them tight. She was spread-eagled wide now, naked on the bed, her pussy glistening with her juices. She began to test the limits of her bondage and rock her hips as Randy flipped the catches on the footboard and removed it, crawling on the bed and up to the Y of her legs.

"Oh fuck," she repeated when he placed both hands under her ass and lifted her snatch to his mouth. Halley arched her back and bridged from the bed as much as her bondage would allow as his tongue began its magic. Her body became lost to his efforts and continued to arch amidst her sighs and groans of pleasure. When he sensed that her orgasm was near, he sat up and looked at her, leaving just a hand covering her pussy, and she shook her limbs in their bonds and cried out in frustration.

A few moments to recover and she raised her head to look down her long body at him, "I told you that you were mean, didn't I?"

Softly he asked her, "What do you want Halley?"

"Fuck me Randy," she answered and watched as he moved to climb over her. He kissed her deeply while holding himself outside of her.

Between the mingling of their mouths she began to breathlessly demand, "I want you cock inside me. Please put it in. I want you cock."

Mid-sentence, he slid his large dick home in one smooth motion balls deep. Halley's body froze and she made a small O with her mouth as he watched her and then began to slow stroke her. She did not speak nor make any sounds other than her breathing. She was focused on what she was feeling deep inside and he watched her as he felt her pussy grip his cock. When she came, she muttered unintelligibly in passion and the muscles of her body constricted.

Randy paused and sat up. He watched her pussy as he withdrew his massive member and those perfect pussy lips tried to maintain their hold. While she was recovering, he untied her ankles and climbed back between her legs and sat on his haunches looking down at her hole dripping with her juices, his cock still hard.

He ran a hand along her inner thigh and asked, "So I'm mean, am I?" and he stopped at her cunt and looked up at her.

Her face turned to a sly grin, "Yes. But in a loving way," and he thumbed her clit and made her eyes close and her body flinch. Once she had recovered, she opened her eyes to him and asked, "Why did you untie my legs?"

Without a word, he scooped her legs in his arms and raised her ankles to his neck, entering her with more force than the previous time. He drove into her so hard that her body slid toward the headboard, giving her arms more slack in their bonds as she howled.

She craned her neck to watch his cock pound her and cried, "Oh fuck" between his strokes. Randy then pushed his torso further so that her hips rotated up and she slid until her head was against the the brass rails of the headboard and her arms straight out from her body. He was pounding straight down into her now and she responded with "Oh" and "Yes" over and over. He was approaching the jumping off point, as was she and he moved his hands down to behind her knees and pressed them into her chest and continued pounding her relentlessly.

Halley's head was slowly turning from side to side as she gulped air like a fish out of water between her cries. She had palmed the bands that ran from her cuffs to the corners on the bed and was pulling hard on them, every sinew of her arms and shoulders taut. As her orgasm came, she cried out again in twisted syllables and her hands worked frantically to try to embrace Randy but were stopped by the cuffs, instead flailing in the air helplessly.

Less than a minute later Randy felt his own orgasm begin and pulled out, climbed onto a still spasming Halley, and shot several thick ropes onto her face and into her open mouth. Much of the excess on her chin and neck made its way to the valley of her throat and pooled there. He lightly sat on her stomach, holding his full weight off of her with his legs, as he caught his breath and watched her swallow his seed and then lick as much as she could into her mouth with her long narrow tongue. He reached behind himself and placed a hand on her pussy. It was still pulsating to the rhythm of their fucking and he smiled.

Halley brought his attention back, "That was good. Can we do it again?"

"Yes baby, but not today. Got to be careful. Let's go take a shower and get you ready for home."

He untied her and they headed out, but he stopped at the computer center and asked her to wait. During the five week interval, Randy had struck upon an idea. It was probably silly and tawdry, but he really didn't care and had started to purchase various pieces of erotic jewelry for future use.

He brought Halley a small box and told her, "When and if you wear this is up to you, but I wanted you to have it."