A Randy Retirement Pt. 01: Averie Ch. 01

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 and fictional. All stories can stand alone, but reading the series gives added insights and descriptions as it unfolds.

Synopsis: Retiree offers to help former student relieve her sexual frustrations for a weekend.

*

September, 2015 - River House

It was not something he had planned. It was not something that was on his mind. As a matter of fact, it started back up totally by chance.

He had experimented with simple bondage while in college, tying up girlfriends while having sex and he learned something about himself. The more he could get them off, the more he got off.

His first teaching and coaching job was in the western part of the state and like all male teachers, there were always some of the high school girls who liked to flirt. He had managed to not become entangled while they were students, but he did hint to a few of them that after they walked across that graduation stage, they could come visit. He had a degree in history and psychology and that last one usually came in handy. A few did come visit and that's how he discovered that he had a penchant for making their inner slut cum out and then beg to cum some more. (He always smiled at that play on words.) That's when he started acquiring numerous aids that would amplify his options to an even greater scale.

After 15 years he took a job at a different high school, one near the coast. There were a much smaller number of girls that he made subtle hints to, but none of them had taken him up on any of the hints. He just figured he'd gotten too old in their eyes, so his exploits trailed off to nothing.

Through a chance, one-time purchase of a lottery ticket he found himself with a post-tax pile of $150 million, which he parlayed in the stock market into a doubling of his fortune. He had over a year's worth of sick days saved up that he converted to a couple of extra years and took early, but full, retirement in his early 50s.

He was 53, fit as a fiddle, with a nice home near the coast and a second home on the Outer Banks. He led a life of leisure, but alone.

And then one Tuesday for lunch he walked into a local sports bar/restaurant and it all changed.

He took a seat in a booth and started to check out the menu when someone plopped down by his side, almost in his lap. Turning he saw brown-eyed blonde, Averie. His mind went into hyperdrive. 'She's probably 25 or 26 by now, said on Facebook she has just broken up with her Marine boyfriend because he got out and went back to Ohio, always was a little mischievous in school.'

"What's up Randy?" She smiled with excellent teeth and golden hair barely to her shoulders, parted on her left. He remembered the time when she was still in school and came to the beach with a group of his nephew's friends. Bikini revealed a nice body, wide-shouldered on a nicely proportioned 5'6" frame. Her body was fuller now, but she hadn't let herself go. She had always called him by his first name.

"Right now, lunch. How are you Averie? You work here?" he replied looking into two brown irises, but aware of a 34B cleavage from 3 undone buttons on a white dress shirt.

"Yeah, working my way through nursing school." and she paused for a beat, "Do you know why I always call you Randy?"

He just smiled and shook his head in the negative.

"Because you always intimidated the hell outta me. I always felt like you were looking right through me."

He cocked his head and then turned to her, "Really? Like how you always seemed in conflict with your parents? Or how a boyfriend would never last too long? Or how you always found yourself frustrated by relationships and the disappointing sex they wrought? And I knew all of that just by looking at you?"

Averie dropped her jaw and just stared at him before regaining her composure, "Yes, exactly like that. I need get back to work before they holler at me. Whadaya have for lunch?"

"You tied up in my playroom would be nice," he replied without looking up from the menu.

"What?"

"Would you like someone who could satisfy you?" he asked her.

"You're too old for me Randy."

"Ah, yes, maybe. But you didn't answer my question, would you like someone who could satisfy you?" he chuckled.

"With my luck I'm not sure that's possible." she replied.

Now was the time for him to make his play, it would either succeed or fall flat, but his little voice said Averie's inner submissive was yearning to come out.

Looking straight into her brown eyes he said, "Oh, it's possible. Just listen and don't interrupt me and when I finish, if you have any questions, I'll answer them. You see most women settle for normal, run of the mill sex in exchange for security. They never get anything exciting sexually in their life and their sexual encounters always leave them wanting. What they are missing is the air of anticipation, of not knowing what's coming, of the build-up that leads to explosion. I can give you that. It will require you to trust me and to endure some physical trials & tribulations, but nothing that will cause you permanent harm. I can give that to you Averie and when I do, you'll be begging me to make you cum and when I do make you cum, you'll be off to la-la land."

Averie started to speak, but he put a finger to her lips, a finger that seemed strangely calming, "I'll have the cheeseburger and fries with a Coke. Go back to work before you get in trouble and think about it."

She straightened herself, wrote down his order in her ticket book and went to put it in to the kitchen.

Her hands trembled slightly as she placed the order on the cook's counter. As she had said, Randy had always intimidated her. She always felt as if he could see right into her and, truth be told, she had always tingled between her thighs when he held her glance a second too long.

Did she really want to do this? He was twice her age; she stole a look his way, he had his head buried in his phone, ignoring her, but he was fine looking for an older man. Six foot and not quite 200 pounds she guessed. He had a shaved, tanned head with broad shoulders and no gut.

She went to check on her other tables as she continued to sneak a glance or two his way, but he was still ignoring her.

Back at the waitress' station, the thoughts came tumbling into her mind, 'Dare I do this? Give up control? La-la land? Trials and tribulations? What the fuck is a tribulation?'

Broken from her thoughts by the cook putting his order up, she took it and the Coke, passing the floor manager and telling her she was taking her break.

Walking to his booth, she placed his order in front of him as she sat down on the bench opposite.

Still ignoring her, he put condiments on his burger, picked it up, took a bite and slowly chewed while looking where the bite had come from. He had made his play and he wasn't going to push the subject. She had to want it, so he waited for her to broach the subject first and he had the patience of an oyster.

As she watched him eat his entire meal, the tingling in her mounted and the silence between them built until, as he finished the last of the fries she blurted out, "Tell me about these trials and tribulations."

He drank the last of his Coke and looked her in the eyes for the first time in the last ten minutes.

With the voice of the teacher he started, "A little bit of pain mixed with a little bit of pleasure has a multiplying effect that leads to sexual combustion. It will require some bondage, some toys and some time spent at my house; say a weekend. I might spank you, but I won't mark you, I won't fuck you and I won't make you to give me a blowjob; unless of course you ask me to."

Averie glanced around the bar to see if anyone else was listening and thought to herself, 'Fat chance of that.'

"I'm sure you've seen pictures of women tied up with various sexual toys and you've probably been curious, now's the time to satisfy that curiosity and with someone you can trust. It's all up to you. When's your next weekend off?"

Before she knew it, she blurted out, "I have this weekend off," and she looked away, thinking of some of the pictures she had stumbled across on those nights she had spent trying to satisfy herself.

"Ok," he replied while she stared at the wall of the booth, "here's the deal. Be at my house by five on Friday afternoon. No need to bring a change of clothes, you won't be needing 'em. No hair or stubble from the neck down or don't come. If you do come, there's no backing out until five on Sunday afternoon." He took a napkin and wrote directions on it. "That's how to get to my house. Five o'clock sharp on Friday, don't be late. It's a one-time offer, this weekend or never," and with that he laid a $100 bill on the booth table and walked out.

She sat and alternated her stares between the address and the face of Ben Franklin. Was he tempting her to prostitute herself or was he just leaving a nice tip? Did she even consider his conditions? She had never shaved herself below the waist, just the occasional bikini wax for swimsuit season.

"Averie, break's over," the floor manager called out to her, breaking her train of thought. She had three days to make a decision.

*

Three days later she found herself riding up a wooded, paved driveway about 10 miles out of town that the directions had led her to. The days had passed with increasing tension as she fought with the decision. She had tried masturbating, but that had not satisfied her. In the past she had fantasized about Randy once or twice but always dismissed acting on it out of insecurity. In the end the yearning in her loins had overrode any caution her brain tried to extend. The fact he had said it was a one-time offer had hung in her mind, do it now or never do it.

And here she was at a two-story house built of dark brown wood and river stone. The wooded area cast the house in shadow with a soft glow seemingly in every window and she found as she parked and got out of the car that her panties were already damp.

She managed to get out of her car, and on nervous legs, walked to a larger than normal oaken door with a heavy brass knocker. It was the first time in her life she had ever used a door knocker.

Randy answered the door in a white, open collared dress shirt and dark slacks, "Hello Averie, welcome to my home," and he extended his arm to the interior as she walked into the foyer and started as the heavy door closed with a thud.

'No turning back now' she thought to herself and felt a small drop of her juices start to ease down her thigh.

He began to tell her about the house. "Upstairs on the right is the media room. On the left are the guest rooms, and a library and of course, the playroom," he turned to her and winked. "My bedroom, bath and office are to the right here on the first floor and the dining room is over here on the left. The living room is right through here."

There was an angled staircase that they walked by on the right as he led her forward toward the sunken living room. It was a peaked roof, open to the second story. The far walls were all windows, looking out onto the river that was some distance below as the house sat back about 75 yards on a bluff.

"It's beautiful," she said as she stopped and took in the sight; wall sconces in the wooden beams lighting the room.

Standing off to her left, he looked out and agreed. "It is. Would you like something to drink?"

"Yes, do you have any wine?"

"I do, white or red?"

"White," she replied, and he went to the bar on their left to pour her drink as she followed.

Giving her the stemware, they both sat on captain's chair barstools and she turned to him.

"So, how does this go down?"

He lit a cigarette and turned his body on the stool to face her, "It goes down by me asking you some personal questions. Don't hold back and don't get embarrassed, just answer, OK?"

"Ok," she replied as she slipped the wine.

"Are you a virgin?"

Averie thought, 'Damn, straight to it' and answered, "No."

"How many guys have you ever been with?"

"One."

Randy was skeptical, "Only one?"

"Well, one at a time. Three total, but separately," she smiled impishly.

"Blowjobs?"

"No. I've never been asked."

He arched his eyebrows and laughed hard and she playfully slapped his thigh, but before she could take her hand back, he grabbed it by the wrist and held it; not hard, but firmly. It was the first time he had touched her since this mental dance had begun last Tuesday and it sent a shock of electricity through her body that surprised her.

"Do anal?"

"No," she squirmed.

"Been with girls?"

"No," with defiance.

"Bondage?"

"No," meekly.

"So, I guess if no bondage, that means no S&M."

She blushed, "Um, what's S&M?"

"Sadism is the enjoyment of giving pain; masochism is the enjoyment of receiving pain."

"Ah, that would be a no."

He took a drag off his cigarette and blew it away from her direction, "If you've only been with one guy at a time, I guess that means no threesomes?"

She shook her head and smiled a wry smile, "Nope."

He released her wrist and rubbed his palm on the top side of her thigh, "Good, cause I don't want to share you with another person right now," and she felt another twitch in her pussy as she subconsciously licked her lips and took another sip of wine.

He crushed out his cigarette in an ashtray, "What's the longest you've ever had sex before taking a break or cumming?"

She looked to the ceiling, "I don't know, I don't time it."

"Estimate."

"Probably thirty minutes."

"Did you do it again afterward?"

"Yes."

"How long that time?"

"Ten minutes," she smiled sadly.

"How many times have you ever actually fucked in one encounter?"

"Twice."

"What's the biggest cock you've ever fucked?"

She held up her two forefingers in front of her face, about six inches apart.

"Ever orgasmed?"

She put her hands in her lap and looked down at the wine glass, "No. Uh, yes. Well, I think so."

"You think so? Oh girl, when I finish with you, you'll know so. I bet all you've ever done is missionary."

She downed the rest of her wine in one gulp and stood up with a look of resolve on her face, "Well dammit, you'd win. Now, I have a question for you."

"Ok," he replied.

"The hundred dollars. Was that a payment or a tip?"

He stood and placed his hands on her shoulders at arm's length, "It was a tip. I don't want you here because I paid you to be here. I want you here because you want to be here, okay? Now, let's eat and if you want to leave you can," and he turned and went to the kitchen.

Averie followed him over and they sat at the U-shaped bar that surrounded the kitchen island and ate salad and spaghetti with garlic bread and a red wine. He asked about her studies and what she had to still complete to become a RN. When they finished, he washed the dishes and she dried. It was all so normal and domesticated and lulled her into a sense of security as she had not expected it to go like this.

Finished with the dishes, she dried her hands on a dish cloth and asked, "OK, so what now?"

He turned to her and said in a firm tone, "Well, you can leave, or you can strip."

"Here," she asked, looking around, suddenly feeling very self-conscious.

"Yes, here. No one is going to see you but me and since you didn't make for the door, I assume you want to continue. Now STRIP," he said forcefully before leaning back against the adjacent kitchen island.

She was dressed in a thick, yellow t-shirt, blue jeans, and flip flops; the footwear being the first to go. She took a deep breath, took hold of her shirttail, and brought it up and over her head, depositing it on the counter. Being braless, two pert, firm B-cups were revealed with a perfect curve and bounce to them and nipples the diameter of a Sweet-Tart. Randy licked his lips in anticipation of suckling them. He noticed the fade of a summer tan, she did not tan in the nude, and he spent several minutes just taking her in without showing the first reaction.

"Would you say something?" she implored, seeking confirmation.

"The jeans," was the only reply.

Her eyes rolled as she turned her head to the outside wall and reached down to her leather belt, loosened it, and begin to wiggle her ass out of the jeans, bringing her panties with them.

He could sense her self-consciousness as she stood there with her head down, not quite comfortable with her nakedness.

"You did very well on your grooming Averie. I appreciate it. You have a beautiful body," he said as he looked at her hairless crotch, "and I'm going to explore all of your most sensitive places."

Her head tilted up and she took him in through the strands of her hair that were hanging in her face and felt the wetness that had subsided during dinner reawaken.

"Follow me," he said as he walked to the adjacent dining room. Over a closed closet doorway hung two webbed straps with wrist restraints attached. He positioned her back to the doorway and placed each of her wrists in a restraint and then adjusted the straps so that she was stretched to her tiptoes.

"Well, I guess that takes care of the bondage question," she said with a touch of nerves as he finished.

"You know Averie, you always did have that wannabe smart mouth on you. Open wide," and he took a ring gag off the counter, placed it between her upper and lower incisors and then buckled it tightly behind her head.

She made unintelligible attempts at speech as he set about placing a three-foot spreader bar on her ankles, wide enough that she couldn't close her legs.

He took a moment to admire her taut body, the way her arms were spread to the upper corners of the door and the way her wide shoulders narrowed down to her waist and then widened back to her hips. He felt his dick spasm and said, "Let's see how wet you are."

His hand barely rubbed the outside of her sex and as she let out a whimper. He brought his hand up and smeared her juices on her gagged mouth, "You're this wet and you've never really cum before?" He left and went to a built-in stereo system in the wall across the room and soon Little Richard was singing "Long Tall Sally."

When the song got to the line, "Having me some fun tonight" he spun on his heel and pointed at her as he sang along. He continued singing the song as he poured lube on a flowered silicone anal plug and then, standing to her left side, began to work it into her ass. She felt the coldness of the lube as he took his time with the plug and smeared some of it in that place where no one or no thing had gone before. The point of the flower began to spread her anus and she squealed, but he kept increasing and relaxing the pressure over and over, gaining a little more intrusion each time.

Averie alternated between looking into his eyes as he sang along with Little Richard and looking down at her crotch and letting out little moans and cries through her gagged mouth. She began panting as Randy continued the pressure until her ass stretched over the wide knot in the plug and fully seated on the inch-wide shaft; the three petals of the plug having opened up inside her rectum to hold it firmly in place.