A Randy Retirement Pt. 14: Hannah & Her Daughters

'Potential slut' involuntarily ran through his mind as he invited her in and led her to the U-shaped island in the kitchen that had four barstools, her black cowgirl boots clacking on the floor. He asked if she would like some wine and she said yes and after pouring they sat on adjacent stools. From the casual conversation, he noticed that she was being overly cocky and aggressive. Randy decided to put her in a formal type situation and see how long that would last.

"I have some questions I would like you to answer, just so I can get some idea of who I have the pleasure of spending the afternoon with. Would that be alright?"

Mina took a quick sip of her white wine and answered eagerly, "Sure thing, fire away."

"Just remember, there are no right or wrong answers. Standard question first, are you a virgin?" and he watched her face as she answered.

"Not since I was fourteen," she replied with a cocky smile.

Randy lit a cigarette and blew the first puff into the air, "How many guys you been with?"

Looking up at the ceiling as she counted in her head, her fingers ticking off the numbers, she eventually looked back at him, "Nine, counting you. Can I have one of those?" and she nodded to the pack on the bar.

"Sure thing, help yourself. I assume you give blowjobs. Do you enjoy sucking cock?"

Mina lit the cigarette she had taken from the pack and inhaled deeply before expelling it and answering, "I love it," and she reached for his crotch.

"Not yet babe," and he gently moved her hand on the bar. "Now, can you deep throat?"

"Of course," cocky again. He wondered how big the cocks she had taken were.

"Ever been face fucked?"

"What?" the first hint of ignorance.

"We'll get back to it. Your mom has told you about the anal. Have you taken it up the ass before?"

"Yes."

"Did you enjoy it?"

She shrugged, "It's not at the top of my list, but I don't mind it."

"Ever been with a girl?"

"Nope, not interested."

"Ever been tied up and fucked?"

"Once," she answered meekly, a hint of trepidation showing.

"Any group sex?"

"Not yet, no. But I wouldn't necessarily be opposed to it."

Randy nodded and proceeded onward, "What's the longest you've ever had sex before someone came?"

Again, she looked to the ceiling, taking a drag on the cig before answering, "Probably ten minutes, but that's a guess. It's not like I'm timing it you know."

Randy smirked. "How many separate times have you ever actually fucked in one encounter?"

"Two," came the quick reply.

"Have you ever orgasmed?"

Confidently, "Of course."

"More than once in an encounter?"

Hesitancy now, "Um, no. Not really."

"Okay, last question. What's the biggest cock you've ever had sex with?"

With a sheepish look, Mina peered at the almost finished cigarette in her hand and answered, "Probably about seven inches? I don't know, I don't carry a ruler with me either when I fuck."

"That's fine Mina. It wasn't a test. The questions were only for informational purposes. Before we begin, open your phone and set it up to text your sister."

"Why?" the thin blonde inquired.

"I'm going to instruct her what I want her to wear," and she did as he requested, her bare breasts showing as she leaned over.

When she handed over her cell, he told her, "Your dress becomes you nicely Mina, you are beautiful," and she beamed as he began to tap out the message.

'Ellie, this is Randy. I want you to wear your best, most revealing bathing suit and a t-shirt and to be here by 8, don't be late.' He hit the "Send" button and handed the phone back to the elder sister.

Placing it on the counter, she crushed out her cigarette and leaned forward on the stool, placed both hands on his thighs and moved in for their first kiss. As she leaned over to him, the thin, black fabric of her dress fell forward and her tits were on full display again, the nipples already hard. The sight awoke his cock and it began to grow.

They both ignored the ding of her phone as their tongues dueled.

His hands reached out and caressed Mina's ass, finding that she was naked under the dress. Bunching it up, they continued to kiss, and he worked his right hand around to her snatch and began to trace the outlines of her pussy with a finger before pushing it inside. She was damp and her body flinched. She was wet, but very tight.

Mina cooed and smiled as he placed small kisses on her cheek and then her ear. Her hands found his belt buckle and began to try to release it, but she had difficulty.

Pushing aside the plunging neckline of her loose dress, Randy suckled one of her breasts, laving the nipple with his tongue. She sighed deeply, then abandoned the buckle and her shaking hands came to caress his head as he switched to the other breast. Mina kissed the smooth shaved head in her hands and her hips started to twist the stool she still sat on.

Randy came back to her face, and they kissed again briefly, before he sat back on his stool and Mina began to deal with the buckle again. Finally, she freed it, unzipped his pants, and reached in.

Randy could see the look of intimidation come over her, even before she took his ten-inch cock from his boxers.

Her mind raced, though "Oh" was the only sound she made. Her mom had told her his dick was really big. She hadn't emphasized it enough. His dick was fucking huge. Her thoughts settled on the daunting challenge she had accepted.

'Alright Mina, calm down,' she said to herself, 'take a deep breath. Yeah, it's big, but a woman can deliver a baby and he's not that big. You can do this."

She grasped him by the base of his cock and began to lick it up and down like it was an ice cream cone, twisting her head around to get all of him wet that was not encased in her tiny hands.

Randy gave her credit, she was good with her tongue, flicking it on the head and pressing it firmly onto his shaft. Finally, she tickled his frenulum using the tip of her tongue and he let out a barely discernable sigh.

She smiled, then paused, took a deep breath, and guided his cock into her mouth, trying to lick the underside with her tongue. She couldn't.

She tried again, but it filled her mouth completely and he could tell that she was struggling with his size. Only a little over three inches went inside before she started to retch. He began to question if it was her angle of attack. His cock was straight up and she still sat with her butt on the stool, leaning over. After several minutes of her trying earnestly, but still failing, he reached and began to remove the dress over her head, forcing her to give up for the moment. The dress was so short that it came off with no problem.

Without words, he stood her up and turned her so that her forearms rested on the countertop. Quickly undressing, he fingered her pussy. It was sopping wet. Randy stooped to remove her boots and ran his tongue along her slit from behind, forcing it inside as he went, and Mina hissed in pleasure.

He spat on his cock and spread his saliva with a closed fist. She was wet, he was wet, it should be a go.

But it wasn't.

Mina squealed and contracted in on herself as he pushed the two-inch wide head of his cock into her.

'God she's tight.'

He backed out and tried again, going exceedingly slow as he steadied his shaft with a hand. Her cunt slowly stretched to receive him, but it was not giving much and she knew it as well. This wasn't like the other guys she had fucked. Nowhere close.

Her back arched as she went up on tiptoe, "Arrggghhhh, damn you're big. Go slow please," and she squirmed on the countertop and turned her head to the side, a look of anguish on her face.

Randy wasn't happy. He didn't mind delivering some pain to enhance pleasure, but not like this. Still, she had not moved a hand to push him away. He decided to continue.

Still not able get half his dick inside her, he decided he would just fuck her with what she could take and slowly stroked it inside her pussy.

The ass before him had begun to squirm as he slowly increased his pace. The first sound of passion came from Mina as a throaty sigh escaped. She tried to push her ass back into him, but to no avail.

Randy reached and bunched her hair, arching her head back slightly. The reflection of her face showed in the oven door across the counter. It was one of those looks that, without sound, you could not tell if it were pain or pleasure. She wasn't running away, so he assumed pleasure.

It was then that her legs began to move as if she were on a stair-step machine and her breathing changed. In a halting voice she announced, "I'm gonna cum. Fuck me! Fuck me harder! Oh god am I gonna cummmm!" and watching her reflection, he saw the tears roll down her cheeks as she did.

Her mascara had run and was smeared under her eyes when he turned her around and pushed her to her knees. She took his cock into her mouth without reservation and immediately retched on the first third of it, but did not stop and continued sucking on it.

When he started facefucking her, he held her with both hands by the hair at the back of her head. She gagged, she retched, spittle forced its way from between her cheeks and his dick. It still would not fit.

Her mouth was filled completely and the gagging commenced before his cockhead even got to the bend in her throat. When Randy pulled out, she would be starved for air and long strings of drool hung from her open mouth. And then he would go at her again. Through it all, she never attempted to push him away. In fact, she latched her hands to the back of his thighs and held on as he pummeled her mouth with what he could get inside.

As faintness set in due to the lack of oxygen, she suddenly felt confused. She did not understand what was happening. The heat in her pussy had begun to rise, just as it had done when she came on the kitchen counter. It had built quickly, and her hips rocked up and down as her legs tried to straighten.

Randy continued to fuck Mina's face, but he noticed her movements and the look of want in her eyes. He knew what was coming.

'This slut is about to cum on half my cock stuffing her mouth.'

He pushed further into her, despite her choking and reached down and held her nose. Mina tried desperately to breath around his cock and her hands tightened on the back of his thighs until she pushed off without him resisting. Her hips were humping air and she came hard, trying to cry aloud and suck air at the same time. Through the entire 30 seconds of her orgasm, she clutched Randy's legs tightly to keep from collapsing to the floor as her body writhed.

Mina's first clear thought was, 'Oh my god, how did THAT make me cum?' She was in a state of confusion and the hormones that still raced through her body did not allow things to clear up.

Randy bent down and helped her to her feet. He wiped the drool and saliva from her mouth, flung it to the floor, and kissed her deeply. Mina moaned into his mouth, her body again responding.

Pulling away, he told her, "Now you know what face fucking is," and, with both wrists clamped behind her back, he marched her to the playroom.

*

Grabbing a straight backed, wooden chair as he entered, he stopped her under a chain hoist hanging from the ceiling. Randy planted the chair and told her, "Sit." When she had done so, he bent and placed his hands on her thighs, his face a few inches from hers. Her makeup was even more of a mess than before, the tracks of her tears evident, and she seemed shell-shocked. He asked her, "Are we done yet?"

Mina's head held firm, but her eyes turned down toward his cock, and in a shaky voice she answered, "No."

"So, you want to continue?"

Her eyes came back to him and in a firmer voice, "Yes."

It was a new and strange sensation she was feeling. She was a little scared and a little excited, all at the same time. The mixture enflamed her. No one had ever been rough with her before. No one had ever had that big of a cock in her before either. She eyed it as he approached her with several wide leather belts slung on his naked shoulder and a small leather string in his hands.

Going behind her, he silently pulled her mussed blonde hair into a ponytail and tied it off with the leather string.

"You like flying Mina?" he asked her as he pulled her arms over and straight down the back of the chair and bound her wrists together. The top wooden slat dug into her armpits as he secured her arms in place and strapped them to the seat of the chair.

"I love flying, but" and he cut her off.

"How about when you hit turbulence, you like that?" and he secured one of the wide belts around her hip bones, pulling her ass back in the seat and tightly against the backrest.

"It can get a little scary." He held a big red ball in front of her and she asked, "What's that?"

"It's a ball-gag, now open wide," and when she opened her mouth again to protest, he pushed it home, buckling it tightly by the leather strap that ran through it.

"Mmmm, Muuuhhh," she managed, and he smiled behind her.

Dropping down, he took her right ankle and pulled it to the back leg of the chair. Another leather strap secured it there. After he had done the same to the left, he came around to face her.

She shook her head, "Muhhh, gahhhh!"

Randy stroked her cheek, "Oh Mina, it'll be fine. I'm just going to teach you a new way to fly."

Randy went back to his storage room and when he returned, he carried a Hitachi wand and a drill-type screwdriver.

Eyes flying wide, she shook her head at the sight of the drill.

"Nnnnhhhh, nnnnhhhh!"

"It's okay, little one. I'm not using the drill on you. It's to secure the vibrator. For your pleasure."

He dropped to a knee and placed the wand on the seat between her thighs. They were spread wide due to her ankles being pulled to the back legs of the chair. With one hand he examined her pussy. It was red and swollen and still gaping from his cock. Spreading the lips further with his fingers, he pushed the bulb of the wand tightly against her sex and the lips wrapped around it on each side. Holding the wand in place, he used U-shaped brackets to secure it, screwing them into the wood with the drill.

Satisfied with his work, he set down the drill and tried to wiggle the wand with his hand. It was rock solid. Then he flipped it on low.

"Nnnnnnnn," the shock of recognition hit Mina like a ton of bricks.

She looked at him and her eyes melted as the fire in her pussy flared up again. Randy smiled at her, knowing that she had not yet realized that this was just the taxiway. Takeoff was about to commence.

As her moans increased, he again went behind her and secured a hook on the thick, top slat of the chair, right between her shoulder blades. She did not even notice the sound of the winch when he lowered the chain. He attached it to the hook and then sent her up, up and away.

As the chair ascended, it tilted forward, the weight of it and its cargo finding its center. The effect was that Mina's body weight forced her cunt down harder onto the bulb of the Hitachi. Her eyes were as wide as ever, her mascara smeared cheeks bulged by the ball, her nostrils flared in her attempts to breath.

Randy spun the chair around so that she faced him. With her body squirming, she alternated looking at him and then her crotch. Drool was beginning to escape from the corners of her mouth and run down in rivulets to the floor.

In a calm, detached voice, he told her, "I hope you enjoy your flight," and he switched the Hitachi to high and left the room.

Mina shrieked at the top of her lungs repeatedly as he walked to the computer room off to the side. The sound was muffled greatly by the ball-gag, but continued as the hormones overtook her. Her pussy was telling her that it needed relief and she knew it was coming. Her body started to shake and in doing so the chair began to bounce on its tether. The sensation translated to the vibrator that was tight against her sex and sent her body into the convulsion of her first in-flight orgasm.

Randy was watching on the monitors. He sat and smoked a cigarette as the thin blonde's body surrendered to the euphoria that the endorphins coursing through her veins delivered. She had been flying for five minutes when the second orgasm arrived, her body shaking so hard that it made the chair spin, and swing, and bounce again.

She tried to talk through the gag and the orgasm that was wracking her lithe body, "lees, LEESSS!!" He couldn't quite make it out through the headphones that he wore, but he thought it was 'Please.' He lit a second cigarette and watched her as the drool increased from around the gag, her head hanging.

Ten minutes into her flight, her head came up and she squealed the arrival of orgasm number three. Randy put out the cigarette and walked into the playroom. Her body convulsed into a cramp and for a moment he thought she might break the chair. Snot had shot from her nose and was planted across the big red ball that filled her mouth and her eyes showed the delirium that she was under as she thrummed along.

"Nnnn, nnnn, nnnahhhh."

When it was over, he reached out and switched off the Hitachi. He let the chair down and began the task of unbinding her.

"We hope you enjoyed your flight on Air Randy, please cum again."

When he had removed the gag, she raised her head to him. "Please fuck me."

Randy was surprised. It was something she had volunteered on her own, not demanded by him. He wondered how she thought he was going to fit inside her any better now than before, but asked her anyway, "How would you like me to fuck you Mina?"

In a tired voice she told him, "In my ass."

Somewhere in her frazzled mind she thought, 'Why in the hell did I just say that. It will never fit in me.'

Since the first time she had felt the monster that Randy sported between his legs she'd had one ongoing thought that spurred her on. Her mama had fucked this man and, 'dammit, I'm gonna fuck him too. No matter what.' It had kept her from running away, it had driven her. And along the way, she had experienced the most amazing orgasms of her young life.

He brought her a bottle of water and offered her a cigarette, along with an ashtray. She took both. Halfway through the bottle, she had finished the cigarette and asked for another, which he obliged.

"You did as instructed before you came here?" he asked.

"Yes, I used my douche."

"Thank you. About the chair, just so you know. I saw something like that once on the Kink porn site. Always wanted to do it to someone," and he pointed toward her, "How is it?" he asked.

"It was," and she paused, took a deep drag on the cig, and watched the ember of it glow. "It was the most intense thing I've ever experienced. I've never come close to cumming like that," and she looked up at him.

"Good to hear it, glad you enjoyed it. But I was asking about the cigarette," and he winked at her.

She laughed. It started as a chuckle, but advanced to a full-blown belly laugh and Randy joined in before disappearing into the storage room again.

'Oh god,' she thought as she wondered what he would come out with this time. When he emerged, he had a blue plastic thing in one hand and a big bottle of lube in the other.

"You ready?" he asked her.

"Yes," with a little anxiousness she replied, then she added, "What's that?" and she tipped her head to the hand that held the plastic object.

Randy held it up, his thumb working the plunger. It looked like an over-sized syringe.

"This? This is a lube-shooter. I'm going to use it to put as much lube as I can, as deep into your ass as I can and see if we can't help you along a little."

It was as big around as one of his fingers and longer than his hand and she hoped it worked. She hid the slight embarrassment she felt at his statement, but stood and asked, "How do we do this?"