A Randy Retirement Pt. 01: Averie Ch. 02

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Retiree helps former student relieve sexual frustration.
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Part 2 of the 42 part series

Updated 07/01/2023
Created 09/08/2020
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Bamboo29
Bamboo29
218 Followers

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

Sunlight streamed through the skylights and windows when Averie opened her eyes. For a moment she did not recognize where she was and panic began to sink in before she remembered cumming the previous night. She looked at her bindings and felt the plug in her ass before a different urge brought itself to the fore of her consciousness.

It was at that moment that Randy had walked in, dressed in black jeans and a burgundy t-shirt.

"I need to pee," were her first words as she watched him begin to unbind her.

"I figured as much, go next door and freshen up. And you can remove the plug," he replied as he finished with the bindings on her left ankle and ran a hand along her leg that prompted shivers. "When you finish, come down to the kitchen."

Averie had made her way to the bathroom and sat on the toilet. As she emptied her bladder, she felt the plug in her anus move with the effort.

"Well, that's not coming out without help," she said aloud and, when she had finished peeing, reached down and pulled on the plug. It took some effort and concentration. Unlike last night when Randy had done it, she decided to go very slowly in working the plug out of her sphincter. Just as the widest part eased past her anal rim, she pushed it back in and felt the tingle in her pussy. She spent a minute or more just fucking her ass with the plug and enjoyed a slow buildup of sexual electricity before stopping.

'I'm liking this entirely too much,' she thought as she wiped herself and then got into the shower and let the hot water flow over her.

As she worked soap into her body, she wondered why the word "please" kept repeating itself in her mind. She did not remember the subliminal messages from her sleep, only that she dreamed last night of being fucked in every way she could imagine. She fingered her nipples and they grew hard despite the hot water and then her hand had found her clit. But despite masturbating herself for several minutes, she could only summon up a tingle.

Twenty minutes later she took the spiral staircase next to the elevator down to the kitchen. Halfway down she realized she was still nude, but was not self-conscious about it and smiled to herself. She found him in the kitchen putting together sandwiches.

"What time is it?" she asked as she walked up behind him and wrapped him in her arms.

"Almost noon, would you like something to eat?" and he turned in her arms and faced her.

"That sounds wonderful," she craned her neck up to kiss him, but he turned away and broke her grip.

"Good, you need to keep up your stamina. I hope you like BLTs. Coke or water to drink?"

"Coke is fine," she replied with a confused tone.

He led her to the adjacent breakfast nook that was a half-hexagon of windows that projected outward from the outer wall of the house and set paper plates down, pulling out a chair for her to sit.

As she did and he helped to push the chair in, he took a fistful of her blonde hair from behind and forced her face up to his, kissing her deeply with his tongue.

'What the hell?' she thought, 'what was wrong when I tried to kiss him?' and then the passion of the moment overtook her.

As he broke the kiss, he looked in her eyes while still holding her hair, "Don't pout Averie, it doesn't suit you. Now eat."

He went to retrieve the beverages while she sat in the breakfast nook and looked at a stacked bacon, lettuce, and tomato sandwich.

She faced the sunken living room, the kitchen to her back and on the same level as the nook. To her left was the river, to her right was the bar area and beyond that the dining room where she had orgasmed last night. Her pussy clinched at the thought.

Randy placed her Coke on the table and sat opposite, with his back to the living room. It was a round oak table with four matching chairs.

Between bites she worked up the nerve to ask, "Why'd you do that?"

With a mouthful of sandwich, he managed to get out, "Wha?"

"Why didn't you let me kiss you?" her head was tilted, and her face showed some measure of resolve.

He swallowed, placed his sandwich back on the plate, and wiped his mouth with a paper towel.

Steeping his hands, he said, "Want is a powerful drug. The more you want, the harder you'll cum. But then your puppy dog eyes from me putting you off got the best of me, which is why I kissed you here at the table."

"Oh," and her resolve melted, "Okay. You can do that more often, ya know?"

He smiled and completely changed the subject, "I love how your nipples stiffen with the coolness of the air conditioner. They're just so, perfect," and she blushed. "I intend to kiss you Averie, and your nipples and everywhere else," and she blushed more and looked away. "Now, finish your lunch. You have a big day ahead."

Silently they ate, the only sounds being their chewing. When finished, they proceeded to clean up in the kitchen.

As she nakedly bent over to open the cabinet for the trash can, he forced her to stay that way with his left hand and admired her slightly open asshole.

"I see the plug had its way," he remarked. "that bodes well for later," and he had then pushed the thumb of his right hand into her pussy.

She audibly sucked in air as he thumb-fucked her while rubbing her clit with his forefinger. She felt the heat from his hand as he increased the forcefulness of his attention to her pussy and she placed both hands on the trash can for support and spread her legs wider to allow him greater access. This wasn't the same as when she was fingering herself in the shower and she briefly wondered why the touch of this man could get her off when she could not.

When she began to rise on her toes and pant, he suddenly stopped and let her stand up. She looked into his eyes with her mouth still open, still panting, eyes pleading, and he placed his thumb in her mouth, "Suck it and clean yourself off my thumb."

Averie took her time with the salty taste of herself and treated his thumb like a lollipop as she used her tongue to swirl around it. After several minutes he had placed his forehead against her forehead and let his eyes bore into hers until she released his thumb and they kissed passionately. As they did, he reached down behind her back and pushed a middle finger into her ass to the third knuckle and left it there as she moaned into his mouth.

When they finally broke the kiss, she looked at him with both hands on his shoulders, foreheads touching again and whispered, "Please make me cum."

"Lead the way, upstairs," he replied in a whisper.

Once they had gotten to the top of the spiral staircase, he instructed her to turn left, which confused her as all she saw was a blank wall with a small seam in the middle, but she did as she was told.

Randy stepped to her right and flipped the switch to open the pocket doorway to his playroom. The doors slid back with a "Whoosh" and she stood in wonderment at the sight before her.

"Welcome to my playroom Averie," and he ushered her inside, the doors whooshing closed behind them.

She turned and looked at the closing doors and then to him, "That sounds like the doors in Star Trek."

He frowned slightly, "Yeah, I keep meaning to do something about that," and he stood by while she turned to take in the room.

There were eight 75" flat-screen TVs scattered along the walls in the main part of the room and most of the rest of the walls were covered in mirrors. Spread around the room were various bondage restraint devices made of 4" black pipe, padded leather devices and various attachment points. On the right was the computer area where Randy had controlled the sounds she had experienced last night with several monitors and one large flat screen in the center. Beyond it another balcony overlooked the river. This was the only natural light in the large room as it had no windows. Further into the room on the right and past the balcony/computer area were two smaller rooms. The first was storage for various BDSM items and the second held only a brass-framed, twin-sized bed. The ceiling also had additional mirrors, cameras and a sturdy track system and chain hoists for suspension bondage.

Without looking at him she said, "It's a little overwhelming."

"Na, you'll do fine. Come over here," and he led her to an area under one of the chain hoists, "Just stand right here, I'll be right back," and he disappeared into the storage room leaving her naked and fidgety.

This was certainly not how she had imagined this weekend to go. She had thought he would just tease her and get her off with his fingers and they would fuck. But his teasing was of a nature that she could not have imagined existed.

Returning, he spread a large white towel on the floor beside her and placed several items upon it. First, he picked up an adjustable spreader bar, set wider than last night, closer to four feet. As he bent down to attach it, he looked up between her breasts and she was watching him, anxiously chewing on her lower lip as he forced her legs wider and wider.

"Like last night, this will keep you from closing your legs," and he reached for another item on the towel and stood up. She felt the strain on her legs as she tried to find comfort with the spreader bar. It was to no avail. She remembered being a cheerleader in high school and felt as if she were attempting a split again.

He again took a handful of her hair and pulled her head back so that she stared straight at the ceiling. "Since you've never sucked cock, you can see how you like it," and he began to push a 3" black penis gag into her open mouth. She reached up with both hands to his, but he did not stop. The rubber penis barely reached to the back of her throat and the beginnings of her gag reflex and she rubbed her throat with her hands. Releasing her, he then pulled her hair back so that he could buckle the gag snugly into place behind her head.

"Just breath through your nose and suck on it. It's not in your throat, so you should be able to get used to it. And take your hands away."

Averie did as she was told, but swallowed constantly as her eyes watered and she struggled with this new sensation. She started the first efforts at sucking on it and found that he had used cherry-flavored lube. If not for the gag she would have smiled.

Noticing this, he asked, "Are you okay?" and she nodded yes through her struggling.

Staying behind her, Randy placed her wrists in leather restraints and fastened them together. He then retrieved some additional items from storage, returning with a 6" long black dildo on a metal pole that also had a Hitachi wand attached. Her eyes widened a bit as he lubed it up in front of her face.

She found herself trying to make out the size of his cock, but the black jeans managed to hide what she had briefly been able to grab through his pants last night.

Kneeling before her, he placed the dildo at the entrance to her pussy and slowly teased it up into her. Averie moaned and rose on her toes, fighting for balance as he worked it inside her. He then adjusted the pole so that it would stay in place with the Hitachi snug on her clit and attached the bottom of the pole to the center of the spreader bar to insure it would not slip out.

She now stood with her heels just barely off the ground. Randy looked at her with a wolfish grin and reached out to tweak and twist her hard nipples, eliciting a squeal from her as she tried to turn her body away from his hands and still maintain her balance.

He released her tits, walked to her side, and began to slap her ass cheeks. He stood with one hand on her bare mons while the other occasionally spanked her to emphasize his words, "Are you ready Averie?"

Her body coursed with blood and she could feel every pump of her heart. Her pussy was on fire from the fullness of the dildo and she intermittently fought with the urge to puke when she sucked too hard on the penis gag in her throat. In between swallows she tried to speak.

"What's that Averie, I didn't catch that," he teased her.

She attempted to speak again.

"You want me to make you cum?"

She emphatically nodded yes and tried to say 'Please,' and it was then that he reached down and flipped the switch on the Hitachi to low and Averie moaned as her body undulated on the pole impaling her.

She jerked involuntarily as he pressed the button on the chain hoist above her and lowered a hook, which he attached to the wrist restraints and then raised her arms until she had to bend over at the waist in strappado bondage. This caused her clit to be pressed deeply into the head of the wand. He then attached each end of her spreader bar to the floor. There was no way for her to avoid the sensations now.

"Two more items Averie," as he held an acrylic plug in front of her bowed head. "This is a double electrode anal plug."

It too was 6" long and as wide as the plug she had slept with last night. As he lubed it with electro-conductive gel and worked it into her ass, he told her, "If I can get it adjusted right, it should make your ass muscles contract and release, like it's fucking you. This is to get you ready for tomorrow when you beg me to fuck your ass."

Averie moaned again as he seated the plug in her ass and attached the wires to the electro power box. She let out little yips and squeals as he played with the dials and checked her asshole until he could see that it pulsated with the flow of electricity.

The first zaps from the plug had hurt, but Averie began to like the feel of the plug as it seemed to squeeze her asshole. It was like it moved in and out of her ass, which was a new sensation for her.

At that moment she noticed that Randy had bent down under her heaving chest and was licking her nipples, getting them wet and covered in saliva. Without showing her, he told her, "These are called claws, but don't worry, they aren't sharp," and she felt a pull at her left nipple. Quickly it was sucked into something and she looked to see the clear silicone tube of a goat milker attached to her breast.

Just as suddenly the right nipple was adorned with a twin attachment and she watched as her nipples stretched and retreated in rhythm with the pumping sound that she had just now noticed. It was then she realized that the sound was also in sequence with the electricity that stimulated her asshole and she felt herself begin that climb to climax.

After almost ten minutes of feeling the rhythms of stimulation and slow build-up, Randy reached down and flipped the Hitachi to the high setting and Averie exploded. Her arms tensed and pulled down on the chain hoist despite the pain it caused. Her legs trembled and she screamed into her penis gag as best she could. Her orgasm lasted a full minute and when it subsided, she went limp in her bondage. But the assault on her nerve endings did not subside and she continued to be stimulated.

Randy was rubbing her back gently, "That was excellent Averie. Let's see if we can't wring another one from you," and he continued to lightly rub her lower back for several more minutes as Averie began hearing the voices again.

'Please fuck my throat.'

'Please fuck me.'

'Please fuck my ass.'

She could not tell if it was real or only in her head, but her pussy, ass and nipples demanded her full attention and she focused on them.

She had never cum twice in an encounter before and she felt as if she were hurtling out of control headlong toward the climax she knew was approaching. Her legs started to quiver, her shoulders started to shake and then she moaned loudly around the gag again as her body convulsed with another shattering orgasm, the acrylic plug shooting from her ass and bouncing on the floor as a result.

Randy switched off the Hitachi, milker and electricity and pointedly looked at the plug lying on the floor, still attached to the power box that it had dragged along with it. He shook his head and unbuckled the penis gag, letting it slip from Averie's mouth into his hand. She gasped, taking in breaths, and tried to speak at the same time.

"I been studyin' nursin'," and she struggled to get the words out, "for two years and I never," she gasped again, "seen nuttin' said a body, could feel like that. I didn't know I could cum like that. Hell, I didn't know anyone could cum like that."

Randy smiled and slowly began to work the claws off her nipples. As the suction gave way, the nipples emerged from their sheaths swollen, angry-red and twice their size of fifteen minutes ago. He massaged them as Averie winced.

"I've got something to take care of that. Ever been skinny-dipping?

Having caught most of her breath, she smiled, "Actually, yeah. I have done that."

He released her from her bonds and replied, "You saw the pool beyond the living room?" She nodded yes, "Go ahead and jump in, I'll join you after I clean this up."

She noticed her image on the large flat-screen of the computer table as she walked out and made her way on sore legs and throbbing body to the pool, which was a nice in-ground one on a large deck that wrapped around the two walls of windows of the living room.

Slowly she walked down the steps into the pool, the warm water soothing her body. After standing for a few moments and letting the water take her, she pushed off and swam toward the deep end.

During the ten minutes of semi-floating there with her elbows on the pool edge, the thought of the image on the flat screen re-entered her mind. 'Dammit, he's recording this,' she realized.

Randy came out in a pair of royal blue swim trunks and when he was halfway to her on the deck, dove headlong into the pool. He swam underwater until he resurfaced between her legs.

"Are you recording me?" she immediately asked as she wrapped her legs around his waist and squeezed for emphasis.

"Yep, everything in the house is filmed from the moment a second person enters it. I'll make you a DVD of your weekend if you want," he replied without a hint of regret.

"Without my permission?" she asked, not in a furious way but more of a question.

"Once you entered my home you gave your permission. When you have as much money as I do, you must take pre-cautions. Sometimes folks get funny ideas about what they are entitled to."

She nodded her head, "Yeah, I guess that makes some sense. It's got to be a pain in the ass to have people always comin' at ya with their hand out."

"Part of the deal. But we would not be here now if it hadn't happened, now would we?" he replied.

"I guess not. Hey! I thought you said skinny-dipping?" she shifted subjects.

"No, I asked if you had ever been. I never said I would join you," he replied as he teased her ass with his hands. "How's the water doing you?"

"Good, but I still think I'm getting cheated," she replied.

He winked at her, "Get back to me on that tomorrow," and he escaped her legs and swam away toward the shallow end. She pushed off and chased him. Catching up as he sat with just his shoulders and head out of the water on the steps. She placed herself on the step below him and he cupped her breasts from behind, gently massaging her nipples. It was two handfuls, bigger than baseballs but not quite as large as softballs and he enjoyed the firmness in his hands.

Bamboo29
Bamboo29
218 Followers