A Randy Retirement Pt. 28: Halley & Gabbie by Bamboo29,Bamboo29

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 shares secret with her sister

August, 2018 — River house

It was the first Friday in August, almost a month since Ellie had left the Outer Banks. Randy had stayed on for the rest of July, but made no effort to hook-up. He spent a lot of time on the laptop, working to get the small farm initiative up and running with a coalition he had found online. After having them investigated by a private security firm and his CPA, Randy had contacted them with his idea. It took some time to get the group to realize he was the real thing and not some con man and from that point things started rolling. The coalition agreed to spend the rest of the year spreading the word and initially vetting any farms that were interested before Randy had them vetted further. Finally, on the last day of July, he had traveled back to the River House.

He spent a few days cleaning up the house and surrounding property, then began to work on his golf game every day. He had just got home from an early morning round and sat at the kitchen island for coffee and a ham and cheese sandwich around noon when his phone dinged. The message raised eyebrows and piqued intrigue.

‘on the way over about one i have a surprise for you hope you are horny.’ Halley ended it with a smiley face.

It took him a bit to decipher her text.

Randy’s mind went into overdrive. ‘What’s she doing home? Is this a new development?’ He knew the anticipation would build for the next hour and though he wasn’t horny before, it was now blossoming. After all, it had been almost a month since he had cum.

Shortly after one, the now twenty-year-old Halley came through the back door, and she couldn’t keep from smiling. She was dressed in a neon yellow halter top and tight washed jeans with a new addition to her wardrobe; camel brown suede, above-the-knee, ‘Fuck-Me’ boots.

His dick immediately jumped in his pants as the long-legged blonde came and wrapped her arms around him from behind while he sat on a kitchen stool. Ellie had worn a similar pair just a month ago, but Randy had to admit that with her coltish legs, Halley wore them better.

She was at least 5’10” with a peachy ass and a 32C rack sporting big, puffy nipples. Her wheat-straw colored hair matched with the barely visible freckling of her skin.

“What are you doing home, I thought it wouldn’t be ’til Christmas?” Randy hugged her back as she sat on an adjacent stool.

“I had to make a quick trip home, just for a few days, something came up,” she replied with a barely contained grin.

“What came up?” Randy asked.

Placing her cell phone on the counter, she told him, “A surprise, one which I brought to you,” and she nodded toward the door.

He turned to find her younger sister, Gabbie, standing just inside the doorway; looking like she was ready to bolt. She was dressed in some type of blue and white summer outfit that was half tube top and half tennis dress.

Gabbie was eighteen, seven inches shorter than her sister and a touch thicker, but not by much. Her face was rounder and her lips fuller than Halley’s. She was also blonde, but her hair had some curl to it as opposed to Halley’s long straight locks and she had more yellow in it. The younger sister’s skin would take a tan and hold it, unlike Halley’s fair skin. Her tits were slightly bigger than Halley’s, between a C and a D. But it was her ass that was the most noticeable difference.

Gabbie had an ass that was slightly bigger, proportionally, than the rest of her body. It looked out of place on her frame, but it wasn’t fat or flabby. In fact, it was an ass that you could bounce a quarter off. Sometimes Randy marveled that the sisters had the same parents.

“Come here,” Halley motioned impatiently with her hand for her sister to come and stand between them at the island and Gab sauntered over, not taking her eyes off Randy.

Big sister took her hands and Gabbie turned to look at her as Halley, looking into Gabbie’s eyes, spoke to him.

“Gabbie’s been asking questions about sex; wanting to know how I found myself. She asked me to teach her, but I told her I wasn’t a teacher, but I would take her to mine. She agreed, but I didn’t tell her who my teacher was, I just drove here. Now she’s a little overwhelmed.”

This was something that Randy had never considered. He had thought Halley a once in a lifetime thing and did not think it would last as long as it had. To have the sister here now was just too good to be true; a stroke of fortune that he wasn’t going to turn down if she were willing.

He reached out and took Gabbie’s nearest hand from her sister and she turned to look, not directly at him, but over his shoulder.

He knew she was nervous, so he chose his words carefully, “Gabbie, we aren’t kin. There is none of my DNA in your DNA. The only thing you must overcome in your mind and conscience is the age difference. I am willing, but you must make your decision now and once you have, it is final. There is no reconsidering it. Do you understand? I can break you in, just like I did Halley, but it must be a decision of your own free will, just like it was Halley’s.”

Gabbie looked to her sister and Halley tilted her head down to look through her eyebrows at her sister, “Say yes Gab, you won’t regret it,” and Gabbie nodded yes.

He got up and went to the kitchen cabinet to dump the dregs of his coffee into the sink, subtly flipping on the video system that recorded everything in the house and turned back to the blonde duo.

His eyes bored into the younger sister, so much so that she knew he was looking at her without even looking his way. “I need you to say it out loud Gabbie, what do you want?”

She looked to her sister, who nodded encouragement, and then to him, “I want you to teach me how to fuck, how to enjoy it. I want you to teach me, just like you did Halley.”

His face remained impassive, but inside he smiled, “You know there is no going back? Sometimes you are going to think that it is too much, too hard, too rough and you will feel overwhelmed; but once we leave this room there is no stopping it. It will be like one of those hurricanes, it’s gonna happen whether you are ready or not. Do you understand that?”

Gabbie nodded.

“Say it,” Halley instructed.

Gabbie blew out a nervous breath from her nose, a little flapping sound escaping her lips, “I understand,” she paused, then added, “and I want it.”

“Okay, Halley, why don’t you introduce her to the playroom,” and he winked at the older sister as she got up and took her sibling to the spiral stairs.

He and Halley had been in an ‘arrangement,’ as she called it, since she was eighteen when he had caught her as she was about to fuck her boyfriend, who turned out to be gay. They had spent time together when she could get home from college and Halley had blossomed into a wonderful young woman, but a sexual beast when she was alone with her pseudo-uncle.

Taking his time walking to his playroom, Randy went the long way as his mind raced into overdrive to devise a scene that would do justice to the opportunity that Halley had provided. He hit on something by the time he reached the main staircase and decided to start out with it and then play it by ear afterward. He went up the main stairs and then doubled back to the playroom.

When he arrived, Gabbie was craning her head around, taking in all the sights in the room. The bondage rigs, the cable hoists, the circular steel rings hanging from the ceiling, the video screens and mirrors, the brass railed bed she could partially see in a smaller room, and all the other furnishings. She was lost in wonder and had a contemplative look.

“Over there by that one and go ahead and strip,” he pointed to the metal pipes as he retrieved some items from a nearby cabinet while taking off his t-shirt. When he turned, he noticed that Halley was stripping her clothes off as well.

“Threesome?” he asked, arching an eyebrow.

“No asshole,” Halley replied smiling, “I thought if she saw us first it would be easier for her.”

Skeptical of that reasoning he replied, “Un-huh and it has nothing to do with any pleasure that you might derive.”

Halley creased that tight, mocking smile of hers in return and mouthed “Oh my god” sarcastically.

Randy cocked an eyebrow. “I won’t even mention seeing you once in eight months and now you bring me your little sister as a present with no prior warning so I could set up something proper,” he replied with his own air of sarcasm before turning to his gift.

“Asshole, nothing about this is proper, but I’m sure you’ll do fine,” the tall blonde whispered to him.

“I wasn’t aware you two were that close,” Randy retorted.

“We’re not, but that doesn’t mean I don’t care for her. You think I want her out there learning this stuff from just anybody? Besides she’ll keep you in shape until I get to the point I can come back more often.”

Randy turned back briefly to the smug smile, “And that’s the only reason?” he asked before looking back to Gabbie.

“No, maybe it’ll keep you from picking up strays,” Halley said to his back.

He ignored her and focused on Gabbie standing there in a tiny red thong that barely could be called a thong; it was more like the thinnest G-string in the history of G-strings.

“Did you pick that out?” he asked her.

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