A Randy Retirement Pt. 30: EllieA Randy Retirement Pt. 30: Ellie


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: College senior visits, and a pickup afterwards

September, 2018 — OBX house


Ellie was on her way for a long weekend. When last they departed, she had requested that he challenge her, but Randy had decided to his intended course would be challenging enough to treat her as her inner whore desired.

She was 21 years old, 5′ 2″ with 34DDs, both pierced with 8g gold segment rings to go along with an identical one in her clit. Blonde, with sapphire blue eyes, she sported a deep copper tan all over and exuded sex. Just thinking about her for more than five minutes made Randy’s 56-year-old cock hard without the aid of any pill and he had been thinking of her all week.

There was a tropical storm that was going to brush the coast on Saturday and it had already turned breezy, though the sun was out. Storms were a way of life in this part of the world, and it was a rare year if there was not at least one storm of some strength sometime between June and the end of September.

An exhuberant Ellie arrived in the afternoon, breezing through the front door in a strap-less, white sundress and sandals, the nipple rings conspicuous through the thin cotton fabric and Randy had to concentrate to contain himself.

Despite the excitement she showed, Ellie embraced him tightly, holding on for longer than normal and Randy immediately sensed something was up.

In these situations, he typically waited it out because people would normally come clean when they were ready. He sat in one of the captain’s chairs that served as stools at the kitchen island and asked, “How’ve you been Ellie?”

Ellie wasn’t ready, as she launched into chattering; a delicious gleam on her face as she stood within arm’s reach.

“Pretty good, better now that I’m here. Mom is so jealous.”


“About me getting to fuck you. I mean she acts likes she’s mad, but when I get home after seeing you, and we get alone, she pumps me for details.”

“Oh really?”

“Yeah, I think she gets off on it.”

Randy laughed softly, shaking his head.

“I do,” Ellie insisted, her hand coming to rest on his forearm.

“Do you tell her the details? You know, about how I pump you the entire time you’re here?”

Ellie joined in his soft laughter.

“Ehh, a little. Just enough to make her wish she was in my place.”

The smile that followed was all pearly whites and sparked an idea in Randy’s mind.

“How would you like to experience what I used to do to your mom?”

Ellie’s face instantly turned to one of confusion.

“I thought I was.”

“Not hardly.”

“So you’ve been holding out on me,” and she ran a French manicured nail down his cheek. “I want to experience it all daddy.”

Randy got up and went to the refrigerator, getting a small, 7.5 ounce can of soda.

“You two would drink Mt. Dew?” she asked mockingly.

Walking past the bar where she stood, he summoned her, “Come over here with me,” and took her to an area in the living room, just down the steps and behind the couch. “On your knees.”

“Shouldn’t I get undressed?”

“No. On your knees,” he restated.

She obeyed and looked up at him expectantly with her hands in her lap, the first few teeth of her libido ratchet clicking quickly through the pawl.

He cupped her chin and Ellie felt her womb quiver at his touch. She had been wanting his cock for two months.

“This is what your mom and I used to do the very first thing when I would come to visit her at college.”

While Randy undressed, he explained that she had to suck his cock without using her hands, taking it as deep as she could, and not backing off until she had completed her task. The task being, with his cock continuously in her throat, she had to undress herself. Only after she was completely naked could she release his dick and breathe.

“Once that is done, I’ll fuck you … without mercy.”

No one could have missed the quiver that shook her.

“Oh, and you have to complete your task before I finish this or no dick,” and she heard the vacuum seal break on the Mt. Dew can.

Ellie tilted her head down and eyed his stiff prick without delay as she knew she was bahis şirketleri now in a race against time. She filled her lungs with as much air as they would hold and followed his instructions just as Randy took his first sip from the can.

The sandals and thong were easy, but she encountered difficulty when she couldn’t pull the sundress over her head and reversed course to pull it down her body. For a moment Randy thought she was going to give up before she finally managed to get it passed her hips, every part of her body moving except her reddening face, which was firmly planted in Randy’s crotch.

By the time she triumphed and backed off, spit was covering her massive chest and dangled from her chin. She looked up at him as she breathed in quick shallow breaths, her nipple rings waving from the effort.

Randy didn’t wait, stooping to set the empty can on the floor and grabbing her by the nape of the neck to bring her up roughly.

“Fuck me,” she croaked in an air starved voice.

“Like mother, like daughter I see. That’s what your mama always said when she had completed her task,” and he turned her toward the couch and bent her over the back of it, just like he would have done to her mama. The gold rings in her 34DDs were swinging wildly.

The first thing he saw was that Ellie had an anal plug in and he reached down and pulled it out slowly with his thumb and middle finger, using his forefinger to tug softly on her clit ring during the process.

She exhaled and bounced on the balls of her feet, that little signal she had when she was impatient to be fucked.

“It won’t be long now my little whore,” he growled.

In her soft, teasing voice, he heard, “Please daddy, go deep right to start,” and Randy smiled.

Her pussy was dripping as he inserted two fingers and then moved them to her asshole, working her own juices into it. She moaned with desire and heard him spit in his hand to lube his cock.

Randy pressed the head into her and after a moment her anal ring abandoned the fight and he watched as her ass swallowed his cock whole.

Ellie moaned and tongued her teeth, then the corner of her mouth, relishing the feel of his cock expanding her rectum. To her, the best thing about his dick was that it felt too big every time he put it inside. He made her feel so full, and it seemed to her at times that she would never get enough of it.

Randy placed his hands, palms up, on her back and demanded, “Hands!” and Ellie submissively complied.

They locked wrists and he moved his hips closer as he pulled her torso back, her pelvis pressed into the back of the couch by his body. Randy began to use the leverage from their linked wrists to pound her ass hard, her hair flying around in a crazed manner as she squealed, “Oh god, fuck me daddy!”

He looked down at her asshole grip his cock as he fucked her into oblivion, hammering her hard until her legs finally spasmed and left the floor. Her body shook in such a mind-bending orgasm that she did not even realize Randy had cum in her ass. He casually withdrew and gently let her slide to the floor in a squirming mass coated in bodily fluids as the aftershocks of her orgasm continued.

When she knew where she was again, Randy gave her a hand up and started herding her to the shower, telling her, “Yep, you’re your mama’s daughter.”

Ellie only mumbled in response; the deep blue of her eyes now washed away. It was a physical tell, one of the many unique and rare things about Ellie. Her eyes physically changed color when she orgasmed hard.

After the shower, Randy went and got her luggage and brought it to his bedroom.

Since she had not let him in on what was bothering her, Randy put his suspicion in a bottle, put a stopper in it, and placed the bottle on a shelf in his mind. He’d take it out and deal with it later, when Ellie decided to clue him in.

“Where do you want to have supper?” he asked as he placed her bags on his dresser.

Ellie knew that she should take every advantage when he gave her choices and asked, “Can we go to that place that looks out over the ocean?”

“The Oceanfront Grill?”

“That’s it!”

“Yeah, we can go there, though it’s gonna be a little windy.”

“The storm?”

“Yeah, but don’t worry about it. It’s only gonna be a tropical storm. A little rain and a little blow, then it’ll be gone. Dress nice,” and he left her to it, going to his walk-in closet and selecting his wardrobe for the evening. He chose black pleated pants, complete with cuffs, a light beige guayabera shirt and soft leather loafers with no socks.

When he walked out of the closet, Ellie had a white thong on and a silk, half-sleeved, cropped top that was a collage of small, colorful flowers at the shoulders and transformed to a solid aqua blue at her waist, a silver dangle navel piercing hanging below the hem. The top had maybe a dozen small buttons, only half of which she had utilized, and her cleavage was on ample display. She was just before pulling up a white, pleated bahis firmaları mini skirt and he walked to her as she did and zipped it closed.

In addition to her piercing jewelry, Ellie had an assortment of bangles on her forearms and three necklaces of different sizes around her neck; including the one he had given her last time, a gold pendant that read “Whore, you say that like it’s a bad thing …”


They got a table next to the railing about midway on the second level of the restaurant. All the outdoor dining was covered by a roof, so it wasn’t too bad with the wind. As they sat, the sun was making its descent in the western sky, it would be dark before they had finished their meal.

“You look very nice,” Randy told her.

“Thank you,” and he could tell that she was surprised he’d said it. “Do you like my necklace?”

“Of course, I gave it to you, but you earned it.”

“I have, haven’t I? You know, I tell all my friends at college all about my sugar daddy.”

Randy chuckled as the waitress arrived and they ordered. Ellie asked for a pitcher of Sangria and ordered a Tuna steak while Randy got fried Mahi.

Once the woman had departed, Randy picked up the interrupted conversation.

“I’m not really your sugar daddy you know, ’cause I don’t buy you things. Do you tell them that?”

“Of course not,” she laughed, “that would ruin my image. Besides, I get my sugar from you another way.”

“What way is that?”

“Your cum, silly.”

She had said it as a part of normal conversation … without hesitation … in her normal voice … in public … at a restaurant full of people. It seemed Ellie’s conversion to a brazen whore was almost complete. Just one more thing to top it off. Randy had plans for that later in the weekend if the weather cooperated.

He had one glass of the Sangria with his meal, Ellie consuming the rest, and she aggressively rubbed his thigh and was chatty about what she was going to do to him all the way home, her ratchet tightening with each mile. It was very enticing, but as he drove, Randy decided that he would give her a challenge when they arrived.


In a back corner of his playroom there were two 6×6 inch lacquered, wooden posts that were eight feet apart. Each was bolted to both floor and ceiling and had attachment points all along their length. It was here that Randy brought Ellie, picking up the Sybian along the way. He had her remove her clothes and all the jewelry while he retrieved bondage cuffs, an attachment for the machine, a leather strap, and a blindfold.

He placed the machine at the foot of one of the posts and put on the attachment. It had two phalluses, each two inches in diameter and six inches long. Randy had her lube the twin dildoes and then situate herself on them, her thighs on either side of the saddle to the Sybian and her knees on the floor.

She did this without question, a little mew escaping her lips as she impaled herself.

Randy then cuffed Ellie’s ankles, clipping them to the post near the floor. Running the strap around her hip bones, he secured it to the post as well so that she couldn’t get off the machine even if she wanted. It was at this point that Randy blindfolded her. The entire time Ellie had not said a word, but her breathing revealed that she was fully amped.

He cuffed her wrists and then stretched each of her arms straight up, clipping them tightly to the back of the post and pulling her head back against the dark wood.

Flipping the Sybian on in its lowest mode, both silicone cocks began to vibrate and rotate softly, Ellie emitting a soft “Ouuu, nice,” and Randy’s face creased into a devilish grin.

This would be the first time his cock had ever been down her throat when she could not adjust herself for the bend, that spot where the esophagus turns downward. Randy was thankful that his cock wasn’t completely erect yet, at least at the beginning.

Ellie had been on simmer for a couple of minutes, and she squirmed as the machine hummed away. The ring in her clit had a little blur to it from the vibration and the dangle at her navel along with the rings in her tits shook in syncopation with the rest of body.

Randy took the cord of the remote and clipped it to the post just above her hands, so that it would be within reach. He then retrieved two boxes and set them on either side of her thighs, stepping up on them and letting his cock slap softly on her cheek.

“Daddy,” the blindfolded Ellie whispered, and her mouth opened like an automatic gate, sticking out her tongue and turning her head toward her desire. Maneuvering his hips so that his cockhead came to rest on the soft palette, Randy stood still and watched as she tried to pull more of him inside without being able to see what she was doing.

He let her fail for several minutes, keeping his cock just far enough away that she could only lick the tip and letting her ramp up further. Then, turning up the dials on the Sybian just a little, Randy put his hands on her kaçak bahis siteleri head and straightened it, aligning his cock with her mouth, and then pushed inside all the way to the turn.

Rising on his toes for a better angle, his dick made the curve and a slow throating ensued with Ellie constantly retching as he kept her head pinned back against the post and slowly advanced the Sybian dial to just short of halfway.

When he pulled completely out and allowed her a breath, he dragged all manner of mucus and drool along with his cock, covering her chin and breasts.

After the first time, Ellie declared distractedly as she blew out globs of saliva, “Whew, that was intense,” and then his cock was tapping her mouth again, almost before she had finished the words.

She would breath when she could, her jaw working to accommodate the unseen invader. Sometimes Randy would put just the head in her mouth and watch as she tried to anticipate when he was going to push the rest down her throat. It became a little game that they played for a few minutes after each break.

But the breaks were never long, as Randy always pushed right back inside, fucking Ellie’s throat while the machine continued to do a number on her pussy and asshole. She opened her mouth as wide as she possibly could to gain some space between her lips and his shaft. Her only issue was that there was little space to be gained.

In response, Randy used breath play on her by holding his cock deep for over a minute until her lips twitched around his shaft and she began to panic for air. He would always relent, and Ellie would cough a couple of times and get one decent lungful of oxygen. Randy watched her knockers sway as she coughed before pinning her head back and starting again. She could never see it coming, the blindfold eliminating her sight and further tightening her ratchet.

As those brief interludes dwindled in number, Ellie became increasingly disoriented, her mind succumbing to the euphoria that was brewing in her body, which was near its boiling point.

Randy pushed so deep that he could not see her lips, they were pressed that hard into his pelvis. Turning the Sybian off, the hard hum of the machine was replaced by the sounds of Ellie’s struggle.

Holding her face in place and looking down at the blindfold that covered her eyes he told her, “I’m gonna get my nut regardless, the question is if I’m ever gonna let you have yours.”

She whined around his cock, trying to beg as he continued to hold her face tight to his groin for a few more seconds before he let her go, pulling out and watching her heave as she tried to inhale, babbling as she could, “Please make me cum!”

The drool was a full-on river by then, running in one long rope from her lower lip and chin to her body as her head turned slightly, trying to home in on his exact position.

He waited another second or two for her to get some air and then rotated the dials of the machine to 10 all at once, Ellie’s mouth opening wider in response to the sudden return of stimuli. Just as she started to squeal, Randy forced her head back against the post and fed her his cock once more.

The lush, copper toned blonde internally detonated as Ellie’s orgasm appropriated the last vestige of her consciousness. Randy watched as the balled fists of her hands unwound, her fingers spread as wide and as straight as they could possibly be as they quaked in such a way that he had to look closely to make sure he wasn’t imagining it.

A choked moan emitted from deep inside her being as his cock filled her windpipe and her body trembled atop the plastic and steel of the Sybian.

It was then that he came, not in multiple cumshots, but one big release of about three seconds. Instead of the thick, ropey sperm that he usually produced, this was the watery, runny kind that sometimes showed up.

It was a product of age and Randy knew it would become more frequent. He noted that it was time to review his vitamin intake. In the meantime, he had a hot blonde to satisfy.

Backing off and stepping down from the boxes, he turned off the machine. The only sound left was Ellie as she gasped for air, cum running down from her chin and slickening her tits further. Her head was down, but she could not see her abdomen as it heaved; though Randy doubted that if the blindfold were off that she could actually see it anyway. With her head hanging and her arms in the bondage position they were in, it put tremendous pressure on her shoulders. He doubted she felt that right then either, as she was still floating.

He waited until his cock showed the first signs of softening and then stepped right back on the boxes. Randy put his thumbs on her forehead, his fingers spread along her temples, and rotated her head back against the post, presenting himself again.

Ellie’s jaw fell open, whether through want or rote, and he slid his cock in once more, dialing up the machine as soon as he was fully inside.

It took nowhere near as long, but she came again in much the same manner as the first one. The difference this time was that Randy did not relent. He kept the machine humming and kept throat fucking her, making her suck while the Sybian worked her over for yet another orgasm.

Bir cevap yazın

E-posta hesabınız yayımlanmayacak.