A Randy Retirement Pt. 28: Halley & Gabbie – Erotic Couplings – Free Sex Story

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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.

She clasped both hands against her mouth, both forefingers sticking straight out at Halley as she tried not to smile.

“She got it for my birthday.”

As small as the accoutrement was, it was easy to notice that she was smooth and bare. Randy thought that Halley had prepped her Sister far more than she had let on. Gabbie was also wet, the darkness of her dampness making the fabric darker.

He took in her eighteen-year-old body, all young and soft, the late summer tan, the dimples in her cheeks, the full lips and shoulder-length curly, blonde hair. No freckles on this one. What intrigued him the most was her fat outer labia and the narrow slit that ran down the center which was showing camel-toed through the wet, red material. It was the fattest labia he had ever seen in person and even more arousal bubbled up from his loins.

“Take the thong off too,” and she complied without hesitation as he questioned her sarcastically.

“Are you a virgin?”

“Nope.”

“How many guys have you had Sex with?”

“One,” putting a single finger up beside her smiling, impish face.

The look made Randy wonder if the inner Gabbie were an imp or a cherub.

“I would ask if he was any good, but how would you know. Did you Orgasm?”

“I think so.”

Eyes rolling, Randy replied, “Oh Gab, when you go home tonight, you’re gonna be able to know if you orgasmed or not. Ever sucked a dick?’

“Yeah, but I’m not sure I did it right.”

Randy shook his head, “So, I’m guessing nothing has ever been in your Ass?”

“No,” with emphasis.

“Well, there is no better time than the present,” and with that her eyes grew wide and she glanced toward the door.

Halley had raved about Anal Sex and even though Gabbie wanted to try it someday, she had never considered that the someday would be today. A yearning surfaced deep down inside, then a little shiver went up her back, and she looked back at Halley, who nodded.

Randy turned to Halley as he took in the exchange and was surprised to see that after she had stripped, she had put the boots back on and he cocked an eyebrow at her.

Using her hands like a presentation model on The Price Is Right, she looked down at them, “I bought these with just this in mind. I’ve been planning on fucking you with them on for a while now.”

Nodding, he replied, “I’m figuring that out, and where my money is going,” and he wiggled his eyebrows at her. His mind quickly factored Halley into his intended actions.

“Come help me put Gabbie in the frame,” and with that they began binding Gabbie in a short, H-shaped pipe frame that consisted of two four-inch pipes bolted to the floor. The pipes were as tall as Gab and had attachment points at the top and bottom. The third horizontal pipe between them would cause her to bend at the hips in an L-shape and put her on her toes. Her wrists were pulled back and bound with bondage cuffs to the top of the two vertical pipes and her ankles were secured by the same on the outside of the pipes at the bottom. This took almost all her movement away and made it impossible for her to try to straighten herself without putting excruciating strain on her shoulders.

He handed Halley a posture collar and a hair tie, “Put this on her and tie her hair back so it doesn’t get in her face. We don’t want Gab missing any of the show,” and while Halley went to work, he squirted some electro-conductive gel on his fingers and began working it into Gabbie’s asshole.

“Oh, uh,” she exclaimed as he worked a second finger in her tight Ass.

“Just relax,” Halley whispered into her ear as she pulled Gabbie’s hair into a ponytail.

Randy lubed up an inch and a half wide electro Anal plug and slowly began working it in. Push, ease off, push a little more, ease off, push some more, ease off and, as Gabbie became accustomed to the feeling, the plug slowly made its way past her sphincter while she moaned, and her Ass wiggled. She felt as if her Ass were overly full and could feel something hard snugged up against the outside of her asshole. Her focus was solely on that point of her body, her asshole, until the next words and sounds slowly made their way to her consciousness in a delayed fashion.

Randy watched her and noticed another difference in the sisters. Whereas Halley’s aureoles were pink, Gabbie’s were a dark brown in color and not as cone shaped. Halley’s were puffy with a small nub that would grow as she got more revved up. Gab had nipples that resembled large gumdrops.

He handed Halley a tube of skin lotion, “lube up her nipples for me,” and he turned to retrieve a portable goat milker from the corner, wheeling it beside her. He then began attaching wires to a modified PES electro box and the Anal plug.

“Halley, stand over there about five feet away facing her,” he directed, then squatted down so that he was eye-to-eye with the younger Sister.

“Ok, here’s the deal. I’m gonna put this goat milker on you and it’s gonna stimulate your tits. At the same time, that plug in your Ass is electrified,” and Gabbie sucked in a deep breath and tried to look behind her but couldn’t due to the posture collar.

He reached out and took her chin and directed her attention back to his words, “It will just be a little sting every now and then, nothing major. It is sound activated for any loud noise. So, every time Halley cried out, or you or I make a noise it will give you a little zap. If I do my job right, by the time I’m fucking Halley good and hard …

“Oh, yessss,” Halley interrupted with a purr. He turned to take her in, standing there in those boots, her hair draped around her shoulders and down past her breasts and two fingers deep in her snatch.

“Patience slut, I’ll be over to scratch that itch in a second.”

Turning back to Gabbie, he continued, “As I was saying, if I do my job and get your Sister good and worked up, instead of a zap, it will make your Anal muscles contract and relax so it will feel like someone is fucking you in the Ass. Questions?”

“Umm,” Gabbie replied, trying to squirm, “how long?”

He looked to her Sister, “until Halley makes me cum.”

Halley’s eyes widened and then she smiled.

Gabbie looked over his head to her Sister, “Okay sis, I don’t know how long my legs are gonna hold out like this, so be — ” and he turned on the PES box, “Owww!!” and the cry sent another jolt to her Ass and she cried out again and then it repeated. It took Gab about a minute to understand the sound activation and get her reactions under control and the shocks to stop.

He then switched on the goat milker and attached the claws to her nipples. They searched for a purchase and then sealed onto her breasts, alternating their suction on each tit. Her nipples took turns pulsing in its grasp, and she gave an “Oh!” followed by an “Ugghh!” when the plug zapped her again. She reacted quicker this time and her sighs took on a softer tone so as not to activate the electricity.

Walking over and blocking Gabbie’s view of her Sister, he smiled at Halley.

“You finagled this to get back for a fuck, didn’t you?” he whispered so as not to give Gab a shock.

She reached and firmly took hold of his manhood and breathed the words out softly, “Every once in a while is a good thing, asshole,” and she winked at him and ran her long, narrow tongue around the outside of her mouth, wetting her lips.

Asshole was Halley’s pet name for Randy, and he smirked as he reached down and dipped a finger. They just stared at each other, her with a hand on his cock, him with a finger deep in her Pussy.

“Whose is this?” he asked, working his finger roughly against Halley’s G-spot.

“Yours,” was the one word reply that came in a voice that dripped with need.

Randy removed his finger and sucked it, just like he was tasting cake batter from a bowl in the kitchen and with the other hand he reached into his pocket and took a pair of translucent suction cups out, putting them to her lips.

“Get them wet,” he ordered, still whispering. She did, taking them both in her other hand and running her tongue around the rims and inside.

He busied himself slobbering on her nipples, the little nubs growing in size and stiffness. When he had them sufficiently wet, he took the cups from her and pressed each in turn onto her nipples and squeezed some air out of them, sucking the little, sweet tart sized nubs deep into the cups.

Halley cried out in an erotic “Ahhh,” and Gabbie replied with an anguished “Agghhh!” She was quicker still this time to control her cries.

Randy dropped his pants and stepped out, kicking them to the side. He dropped to his knees and reached around Halley’s hips, taking a half of her Ass in each hand, pressing his face into her mound, and arching his head back.

Halley in turn arched her back and spread her legs to give him freer access to her Sex, placing her hands on his head for support.

His tongue went deep into her several times before he latched onto her clit. He took it into his teeth and lightly bit down, flicking her Love bud with his tongue, while Halley gasped loudly, and Gabbie cried out.

Halley’s breathing was becoming heavy and he recognized the sign. He stopped, stood, and turned to the side so that in Gabbie’s view, she saw him from his right and got her first view of his dick. He reached out and turned Halley so that she was facing him, Gabbie viewing her left.

Slowly Randy increased the pressure on Halley’s shoulders until she understood and dropped to the floor, hands on her thighs, and took the tip of the biggest cock Gabbie had ever seen into her mouth.

Gab was not great with measurements, but it had to be at least 9 inches long and bigger around than a hacky sack. There was no way that was fitting in her and the just the thought of trying to take it caused the wetness between her legs to increase.

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