A Randy Retirement Pt. 21: Liz

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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 forty-five 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: Impulse gets a former student snowed in

February, 2018 – River House

During the first week of January Randy studied Halley’s (see previous Halley stories for background if you’d like) financial plan and found it sound. She had covered all the bases and he was impressed with her work. It was becoming evident that she had a good head on her shoulders, even if fucking him was her passion. He sent her a text with his seal of approval, but kept it appropriate just in case somehow it was seen by others.

He spent some time reflecting on the last two and a half years. He had been a player until his mid-forties, but had never married. Partly because he allowed work to get in the way and partly because he found too many willing sluts to fuck. Then he had fallen in love and after a few years that had ended badly, and he had gone dormant for almost two decades.

A chance encounter in a restaurant had brought him out of his stasis and the man who had emerged was edgier, more intense, and more dominant. The money had made a difference, not having to have a job had freed him up to be as provocative as he could get away with, short of a lawsuit. But he was confident he could read the signs well enough to avoid those, and he had the videos as backup if need be. Society had changed and so had the rules, but that age-old yearning had not. It was rooted deep inside, at least for a few. He found that he enjoyed the hunt for those few.

At the moment, that was of little concern to him as he sat and watched the gray clouds of winter. What he wondered about the most as he sat there was how many willing sluts he had let pass by, without even a sniff, during his dormancy.

“Lost opportunities,” he said aloud as he rose to make some coffee, “that won’t happen again.”


A month later, he was growing restless. Winter always made Randy that way. He abhorred cold weather, but still, he felt the need to get out of the house and searched online to find something, anything, to occupy his mind.

The small Southern city near where Randy had grown up had been founded four hundred years ago. It still had narrow streets in the old downtown area, most of the buildings there being remnants of the horse and buggy days of the late 1800s and early 1900s. A few of them were even older.

There was a theater downtown that had opened during America’s first Progressive sincan escort Movement to show silent movies and host traveling troupes before progressing as time passed to show the new talking films. When the move of businesses to the outskirts came and the vibrancy of downtown withered, it had stood vacant for many years in the late sixties and the seventies. In the early eighties, a local group put together the money to buy and refurbish it, turning it into a community theater for local productions.

It was at that theater Randy found himself, late on a cold Friday afternoon, to take in a production of “Bonnie and Clyde.” Standing in line for a ticket, he recognized a familiar ass in front of him, although it was slightly wider now and accompanied by a male. It was Averie, from three and a half years before. She was the one that got him started back on the hunt.

“Hello, Averie. Long time, no see.”

Randy could tell by the movement of her shoulders that she recognized his voice, yet she turned with a broad, toothy smile and introduced him to her husband. Randy hadn’t known she had married, but shook hands and congratulated them both.

Averie must have felt the need to explain as she told her spouse, “This was one of my teachers. One of my favorite teachers. He taught me a lot, things that I still use today.”

Randy could tell that the husband was intrigued, but before he could comment the ticket lady commanded his attention and they both turned back to the booth.

“Have a good time at the show,” Randy said and when Averie turned back to thank him, Randy winked at her. She showed just the slightest hint of a blush and then a smile before she went back to her husband.

‘Oh to be a fly on the wall when they get home tonight,’ he thought to himself as he grinned.

When his turn came, Randy purchased a ticket on the next to last row for a seat that was three spots from the aisle. He entered and seated himself, his overcoat in his lap, and was perusing the handbill when someone plopped themself down in the seat beside him and said “Hey!”

He turned to view long, dark blonde hair and a pair of greyish-blue eyes above a slim Roman nose and the lightest of freckles set in fair skin. Liz was an Honors student he had taught in the last year of his career and she couldn’t have been more than 24 years old.

“Hello, Liz. How are you?”

“Generally bored, but I’m excited for the play. How have you been?”

Randy closed the handbill and gave her his attention. She had always put on the air of Miss Prim to use your body the way that, deep down inside, you’ve always wanted it to be used. To fuck, just for the sake of the act and the orgasms.”

Randy could tell that she was hot, maybe hotter than she had ever been in her life. Liz’s body moved closer of its own accord, her head even with the top of his shoulders. Turning her face up to him, he knew exactly what she wanted at that moment.

“If you want to, go ahead, but remember not to pick up the bat unless you’re gonna play ball,” and he stood there and waited her out.

She swallowed and rose on her toes to kiss him. Randy took her in his arms and turned the passionate kiss into a seething, amorous ankara escort fest of dueling tongues and fondling, kissing her deeply and forcefully.

He broke the kiss and turned her around, placing her hands on the stairway railing, her feet far enough away so that she had to bend at the waist. Holding her there with his left hand between her shoulder blades, he swatted her hard on the ass.

“Owllll!” Liz called out and dipped her head between her arms.

‘Twack!’ he spanked her again, gaining the same response. He continued and after the fifth time lighting up her ass, Liz’s head rose and turned to look back at him. She flexed her knees and made her ass dip up and down and Randy spanked her even harder.

Audibly she sucked in air between her teeth, her lips pursed in a snarl, and he told her, “Make sure of what you ask for Liz, because once we start, then you are in all the way to the end.”

She waved her ass at him again, “I’m in all the way,” and earned one last slap of her ass.

Randy still had his doubts, but as he took Liz up the stairs to the playroom, he decided that he needed to make her hot enough that there was no way she would back out.

When the doors swished back and she saw the room, she paused for the slightest of moments and then made her way inside.

Randy’s voice boomed from behind her, “I told you it might not be what you thought it was.”

She turned to him and replied, “I read the Fifty Shades series. Just please, don’t cum on my face.”

“So, you’re not a swallower?” he asked as he came to her and placed his hands on her hips. They reminded him of the 1950s black and white pictures of models posing in one-piece bathing suits.

“Oh, I’ll swallow it. I just don’t want it gobbed on my face.”

Randy screwed up his own face in confusion, “That’s a strange thing to be squeamish about, considering that you’d swallow it,” but she didn’t answer as he had started to remove her boots, jeans, and panties and before he had finished, she had removed her top and low-cut bra.

She wasn’t shaved, but had trimmed her bush at some point in her life. Still, it was too much for his taste and Randy silently noted that he’d have to do something about that if this continued into the night.

Her thighs and calves were muscled, like you would expect a dancer’s to be. His hands found her breasts; they were firm and round and filled his hands, then kissed her deeply again. It was a long one, wet and sloppy, and it got her even hotter, but it was obvious that she was nervous by the slight tremor of her hands on his shoulders.

Randy began to try to kiss the nervousness out of her, moving all over her body and lightly kissing her. On her shoulders, the nape of her neck, her earlobes, down her left side and up the right and finally on each nipple; though he lingered there and suckled each for a dozen seconds or more. He then straightened and kissed her chin before locking lips with her again.

When he finally broke off from the kiss the realization of it all hit her and she asked him, “Are we gonna do it now?”

“Well, we could. But first off, I thought I’d make you cum without fucking you.”

Her head drew back, ticked to the right, but etimegut escort her eyes stayed on him, perplexed.

“Hey, you’re the one who’s read Fifty Shades,” Randy snickered, “Come with me.”

He led her towards the back where the Sybian sat between two lacquered six-by-six wooden posts, a towel covering it. He whipped off the towel to reveal the lone sentinel of a six-inch long dildo attachment standing at attention.

“I’m going to fuck that?” she turned to him in wonder as he bent to apply lube to the dildo.

“No, it’s going to fuck you, with me at the controls. Hop on, you’re wet enough.”

Liz blushed, but moved to straddle the black box and slowly squatted herself down on the inch and a half wide phallus.

“Down on your knees so you get it all in,” he commanded. She looked at him with a hint of annoyance before she complied and that same thin, compressed smile overcame her face.

He marveled that so many women, when they first came into this room, would do whatever he told them to do without any form of protest. It had happened over and over again. He always wondered what he would do when one finally balked.

Walking behind her, he took each wrist in turn, placing a leather bondage cuff on each and clipping it to the appropriate post. Liz turned her head to watch him and when he began to cuff her ankles, she blew out the air from her lungs forcefully.

“Oh shit,” she murmured, the tremble still in her voice.

With a short chain on each ankle cuff, Randy clipped them to the wall. The result was that her feet were dangling in the air, pushing her torso forward just enough to force her clit firmly against the rubber nubs of the Sybian attachment.

He left her for a moment and upon returning, he stepped behind her, took her blonde hair into his hands and put it into a ponytail with a hair tie.

“Thank you,” she told him as he came around to face her, the same wide and tight smile looking back at him.

Randy took in how her nose turned down the slightest bit at the very tip and the slight freckling of her skin and smiled back at her, “Hold that sentiment for later.”

He picked up the control and just held it in his hands while he watched the tiny aureoles on her chest rise and fall with her breathing. The buds of her nipples had hardened inside the pink circles, and he wondered for a moment how large they would get. Then he rotated the dial for vibration to five and watched as, to no avail, Liz’s thighs tried to walk her off the Sybian. Her face squinted, her breath caught in her throat, then her mouth made an ‘O’ and he could have sworn that her nipples increased in size by half as they instantly hardened further.

Her face continued in various contortions as her body began to vibrate on the machine. She looked around constantly, even turning several times to look at her wrists locked in place. Randy thought maybe she were seeking an avenue of escape, but there was none. As the vibrations continued their assault on her pussy, the facial expressions turned into a cross between the ‘O’ face and the lip-pouting face as her mouth was in continuous motion. It only spurred his own desire onward.

Placing two boxes in front, her attention was drawn to them and thus distracted her until he stepped upon them and reached out with his left hand to push her head back. Liz’s mouth opened automatically, and with his right hand, he guided his cockhead into her mouth.

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