A Randy Retirement Pt. 14: Hannah & Her Daughters

"Stand up, turn around, spread your legs and put your hands on the back of the chair," he told her as he uncapped the bottle. He drew a full load of lube into the shooter and continued, "Now this is probably gonna be cold, so brace yourself."

Mina stared at the far wall and winced as the shooter entered her anal cavity. She felt Randy push it deep inside her and the cold liquid as he depressed the plunger. Seven more times he filled the shooter. Seven more times he deposited lube into her ass. She could feel it fill her.

Randy turned her around and sat himself in the chair, spreading more lube on his cock. "I'm going to let you set the pace on this one, at least in the beginning," and he grasped her tiny waist and moved her back toward him.

Mina backed up and put her feet on either side of the chair. She reached between her legs and grasped his massive meat and then paused.

She turned to look at him over her shoulder, "Just how big is this thing anyways?"

Sarcastically he came back at her, "If you had brought a ruler you could see for yourself."

She squeezed his cock with her hand.

Randy laughed, "It's about ten-inches long and about two in diameter."

Squatting onto the head, she questioned, "How the hell did you get" and the pressure on her anal ring made the question unimportant in the moment. He held her up by her waist as she continued to try to press him inside her asshole.

"That's a girl, push and relax, push and relax."

She did as she was told but the frustration was mounting. On the verge of giving up, she told him, "I don't think it's gonna" and then the head slid inside her ass an inch deep. "Oh my lord, its inside me."

"Yes, now start to ease down on it. Slowly."

Still grasping his dick, she eased herself down on his cock. The pressure on her anal muscles was tremendous as his cock stretched her. When she lowered herself another inch the lube gushed from her ass around his cock. She managed to get about four inches inside and then she started to use her legs to fuck herself. The feeling of being full was almost more than she could handle, but she wanted this badly and picked up the pace as she winced and sucked in breaths.

Randy knew she was struggling with his cock. The lube was being squeezed out as more of his dick entered her asshole. It was all over his lap and the chair and floor. Mina was doing her best, but it just wasn't happening to his satisfaction.

When she had settled into a steady rhythm and seemed somewhat comfortable, he whispered to her, "I'm gonna take the lead now."

Acknowledged with a shake of her head, Mina steeled herself for what was next. Randy suddenly came out of the chair with her and his cock pushed deeper as he did. She cried out loudly as she felt an orgasm rushing headlong into her future.

"Fuck me Randy, oh fuck my ass!"

He stood her against the near wall, grabbed her hair and turned the side of her face against it. With the difference in their heights, he was fucking her ass by just straightening his legs and his cock pushed over half-way inside her all at once.

Mina was frantic. Not from pain, although there was a burning sensation, but from the orgasm she wanted so badly. Eventually it arrived and it caused her to collapse to her knees with Randy still engaged in her ass and still pumping as he squatted over her and continued to hold her hair.

Just as her orgasm subsided, his commenced and he withdrew from her ass, the lube flowing from her gaping hole. Still holding her hair, he spun her around and jacked his dick with his free hand as hot jism painted her face. When Mina realized what was happening, she stuck out her tongue and caught the end of it as he let her hair go.

Afterward, when he was spent, he noticed a small smear of blood on his cock. It would not be the first time he had torn a woman.

Randy looked at her face. She had cum on her forehead, cheeks, nose and chin. She was flushed and her eyes still watered. The mascara had turned it into even more of a mess, giving her the impression of having two black eyes that were trying to spread down her face. He briefly thought of the image of a circus clown.

*

He had escorted her to the shower, where he turned gentle. He bathed her and cleaned her face of the spoiled make-up. He pulled her ass cheeks apart and checked her, probing with a forefinger as Mina jerked. Sure enough, there was a tiny, but obvious, tear on the posterior of her anus.

She wasn't so cocky anymore. If anything, she was docile. Randy begun to wonder if her spirit was broken. He did not want that at all. As he washed her hair, she spoke to him.

"I'm sorry."

He had to ask her to repeat it to make sure it was what he heard. It was.

"Why are you sorry Mina?" as he continued to massage shampoo into her scalp.

"Because I couldn't fuck you like mom. Because you're too big for me."

He turned her to face him, wiping his soapy hands down the side of her head and placing them on her shoulders. "That's nothing to be sorry for young lady. If that's anyone's problem, it's my problem, not yours. And you're not your mama, you're Mina, with her own life and goals and aspirations. Taking a big cock is just a matter of practice and you did great for your first time."

It was then that it hit him. There was no 'la petite mort.' Mina wasn't like her mom in that way either.

She had smiled at him as he talked, but he still wasn't convinced that what he had said had taken. So he went at it again with another tactic.

"Mina," and the blue eyes looked at him, a little brighter now. "Did you learn to ride a bike the very first time you sat on one?"

"No. I fell."

"So, it took time and practice?"

"Yes."

"Did you swim the very first time you tried?"

The light was brightened more in her eyes, "No, I took lessons all summer when I was five."

She hugged him tightly and he started to rinse off her head. He still wasn't sure that she understood.

*

Mina was obviously walking sore, the boots clacking on the floor, as she headed for the door. She had a wet head and no make-up on now.

A thought ran through Randy's mind as he watched her smile with a tinge of sadness, get in her car and drive away.

'Must have been only small dicks, or average at the best.'

Coming back into the house, more thoughts came.

'That didn't turn out like I'd hoped.'

He glanced at the clock in the kitchen.

'Just after five. I got less than three hours until the main show commences,' and he started straightening up the house for her arrival.

*

Part III - Saturday Night - Ellie

Ellie had asked her mom why Randy wanted her to wear a bathing suit when she had gotten the text from her sister's phone early in the afternoon. Hannah told her daughter that she did not know, but he had his reasons. 'He always has his reasons,' she thought, but did not say.

She then told her to wear the black one with the white pinstripes. Ellie had texted back that she understood and looked out the window as the ocean waves rolled in.

When Mina got back, she looked exhausted, but otherwise fine. Still, Ellie could tell that something was bothering her sister.

Mom and sister asked her how things went, and Mina told them it was great and gave an overview of her time with mom's former lover.

Mina smiled at Ellie, "You're gonna love it sis." She thought the lie wasn't that bad. Ellie wasn't a rookie at sex, but she had not experimented as much as Mina. She certainly thought that Ellie should have her moment as well and didn't want to scare her.

"Well, I guess I need to get ready," and she headed for her room, looking back just once to take in the expended look in Mina's eyes one more time. Ellie realized that that was what struck her when Mina first got back. 'She wasn't exhausted, she was expended,' Ellie thought.

When Ellie had departed to her room, Hannah asked her eldest daughter, "So, now the truth, how was it?"

"I'll tell you after Ellie leaves, I promise," and she went to the refrigerator and opened a bottle of wine.

Slightly over an hour later, Ellie came back to her mother and sister, who were on their second bottle, "Well, I'm off. Wish me luck."

They did, and watched her leave from the window. Mina then turned to her mother.

"I couldn't take him mom."

"What?

"It wouldn't fit inside me. In any hole. I never seen a dick that big in my life."

"Oh Mina," and Hannah came to hug her.

Mina shrugged her off and reached for her wine glass, "I was so embarrassed. I kept trying to take it all, but he just couldn't get it in me, even with lube."

"It's okay, baby. It's not your fault. Nothing's wrong with you."

Mina was eyeing her full glass, "But mom, you were right," and she took a large gulp of the white before turning to her mother, "I've never cum so hard and so many times in my life."

*

It was three minutes until eight when Randy's doorbell rang. After starting the recorder, he opened it to a vision with blonde hair and sapphire blue eyes. Ellie had that Coppertone tan and he suspected that it was an all-over tan. She barely had any makeup on and the bikini she wore was perfect, not skimpy or lewd, and cut high on her hips, black with wide white pinstripes. She had on a white long-sleeved t-shirt, tied in a knot just above her belly button. The party balloons on her chest were every bit of 34DD and topped off a tiny waist and a big bubble butt. On her feet she wore sandals.

"May I come in?" she interrupted his mental inspection.

"Yes, come right in. Make yourself at home," and he ushered her inside. "Go right through to the living room there on the right," and he pointed the way. Following along he watched the sway of her ass cheeks. The bikini bottom was a wide thong.

'Would you look at that,' he thought as his eyes almost watered.

They sat on separate ends of the couch and faced each other, the Atlantic waves still pounding the beach in front of them. Randy was leaned back into the couch, but Ellie sat on the edge of her seat, and he thought she was about to bolt until she slipped off the sandals.

"That's a nice tan you have," he sought to break the ice.

Her eyes looked down, as if subconscious, but then lifted to him and she smiled, "Thank you."

"Are you tanned all over?"

With no hesitancy she answered.

"Yes. I sunbathe in the backyard. We have a privacy fence," a trace of gaiety in her voice. Randy wondered about the shyness considering her lack of hesitation in revealing the completeness of her tan or how she got it.

He asked her if she had any trouble finding her way and then some questions about her studies in college, the shyness returning. Ellie wasn't cold to him in her responses, but the shyness pervaded in her answers.

"So, tell me about your family," he asked.

"What do you mean?"

"What's the dynamic in the family? How do y'all get along?"

"Well, you know my mom and my sister. And you know my mom and dad are divorced and that I have a brother."

"But have you always gotten along?"

"Yeah, kinda."

"Kinda how?"

She started slowly, "We do stuff together and all and we mostly get along. Except when Mina and I are arguing over who gets something and she usually wins. And then to keep the peace I let it go. I always kinda felt in the background. Behind mom and Mina. And then my brother came along, and I became the middle child, and" she stopped talking, pausing to assess the thoughts that had gathered and that she was about to confess to this stranger. She had not been the type to complain, to anyone. She wondered why now she was doing it. Somehow it felt like she needed to tell him this, something she had never told anyone. Maybe it was the way he had listened as they talked at the restaurant. Whatever it was, she felt chatty, but it was not second nature for her to talk so freely.

Randy noticed how her chest moved as she breathed. He waited her out, watching those gorgeous melons as they rose and fell, even as he knew she was debating with herself.

When Ellie was ready, she locked her eyes on him and poured the rest of it out, "I always felt like an afterthought once my brother came along. I wasn't the oldest. I wasn't the youngest anymore. I was always the third to be asked about something, like I was being ignored for the most part and thrown a bone occasionally. I wonder sometimes if they think I'm good enough or if I matter. So, I just kinda stay in the background and take care of myself"

Her self-pity aside, Randy remembered enough from his psych minor, all those years ago, to know that some middle children go through similar feelings to what Ellie expressed.

"Ellie, I am going to be very honest with you," and he sat forward on the couch, placing his elbows on his knees and returned her gaze.

"My greatest asset is my bluntness. My greatest sin is also my bluntness. You, my dear, are gorgeous."

She blushed.

"No matter what goes on here today. If we just talk and you leave or if we talk and we fuck; know this. Your body is the envy of any man's dreams, young or old and I believe you have the personality to match. I see glee and intrigue and spontaneity and wonder in those deep blue eyes of yours. And your body, there aren't words to do it justice. It's more than wonderful, it's perfect. I see and sense a sexual creature who doesn't know how to express itself. Most women have a little bit of slut in them. Most women also suppress it, or deny it, or they're scared of it. I want to introduce you to it. I want to play with your tits, eat you out, tie you up and fuck you until you think you can't cum again and then fuck you some more. But most of all, I want to provide you the means to find that sexual creature that's within you and let it loose."

Ellie felt her face flush and then a strange, hot twitch in her pussy, which surprised her again because it had never happened before today. She wanted to call bullshit on his little speech. But she could not deny that it had enflamed her to the point of dampness.

"I mean, you've fucked before, right?"

"Yes," she shyly admitted.

"You've had more than one lover?"

"Three," and she squirmed a little.

"You like sucking cock?"

Ellie screwed up her face, "Eh, I wouldn't say like. I do it because it's expected," and she seemed to be getting into answering the questions a little.

"Has a guy ever made you cum from doing you orally/"

"No," with just a hint of frustration.

"Have you ever let one of your lovers take your ass?"

She hesitated and gulped, her eyes averting his, "You'd be the first."

Randy nodded as if that was a fait accompli and proceeded, "Look at me," and when she did, he continued, "What's the longest you've ever had sex before someone climaxed?"

This time there was no hesitation, "Less than ten minutes and it's always been the guy." Apparently, unlike her sister, Ellie did keep time.

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

"Two," again without hesitation. Randy got a feeling Ellie like to keep score.

"Have you ever orgasmed?"

Distractedly she answered, "Yes," a little pink coming to her tanned face.

"It's nothing to be embarrassed about Ellie. Have you orgasmed more than once in the same encounter?"

"No," and she blushed more.

"What's the biggest cock you've ever had sex with?"

Ellie stuck out her bottom lip and considered before holding up her palm and answering, "About the length of my hand."

Randy knew, without looking, that she had small hands.

"I have a question for you," she countered, unexpectedly.

"Ok, that's only fair, but you only get one," and he smiled at the glimpse of her spirit.

"Why smooth," and she paused before nodding to her own crotch, "down there?"

"You mean why do I want your pussy hairless?" He noticed that her eyes widened just a little at his crudeness and continued, "Because I wouldn't want to kiss you if you had a full beard and I don't want to eat you with one either. I like to watch what's going on without looking through a forest."

Taken aback by his bluntness, she considered it for a moment, and he could see acceptance as it washed over her face. There were little signs of progress, but no commitment. He decided to give her an out.

"Tell you what Ellie. You still seem a little unsure," and before he could finish the sentence, she interrupted him.

"It's not that I don't want to be here. It's just that," and she paused, seeking the right words, "I'm afraid I won't enjoy it like my mom and Mina."

"You don't enjoy sex?"

Her voice rose an octave as she rushed to get it out, "I don't know if I enjoy sex. I don't know what 'enjoy sex' means. I don't know if I'm doing it right. I don't know if the guy was doing it right. I don't know what it's supposed to feel like or if the feelings I have are the feelings I'm supposed to have," and she paused and calmed before finishing, "I just don't know."

He wondered briefly if her sister had enjoyed her afternoon. Then his voice softened, and he told her, "I understand Ellie. Really, I do. It can be confusing to grow from a girl to a woman. Here's something for you to consider. It does not matter if you enjoy it in the same way as your mom or your sister. Sex is different for each person. It only matters if you enjoy it in your own way. We all have our likes and dislikes. They are like guideposts on our own individual sexual journeys. I help women find their own path on that journey and sometimes push them to boundaries that they may be uncomfortable with and then push them across those boundaries."

He paused and let her take in what he'd said before continuing, "One has to know where the boundaries are in order to know themselves and you'll never know where the boundaries are unless you push pass them."

He paused again for a few seconds and then took his shot, "I'll make you a bet, okay?"

Ellie arched an eyebrow in question.

"If I can make you cum in ten minutes without taking any of your clothes off, then I get to fuck you any way I like. If you don't cum in ten minutes you can go back to mama."

Ellie felt her loins twinge at his suggestion. Never had anyone been able to conjure up a tingle by just talking to her before, as Randy was doing to her now with his lewdness and questions. She didn't know why, but she shook her head yes and agreed to the bet.

He had her straighten on the couch and face the television, spread her bare legs, and put her hands behind her back. He set the timer on his phone for ten minutes and showed it to her as he started it.

Then he hit "play" on the TV remote and the video of her mother appeared on the screen. Her mouth slowly opened in shock and while she watched, he lightly ran a finger along her breast and then down to her slit, both still covered by the suit and t-shirt. The wetness between her legs was evident through the fabric.

"You're wet Ellie, are you excited?" and he brought his finger close to her nose. It was as if she could not see or smell it, she was engrossed in her mother being pummeled by this man who sat beside her. And the look on her mother's face was evident with want and desire. She had never seen that look from her mom before, but she recognized it somehow. All this built-up anticipation and dread since last night after dinner. All this sexual discussion. All the non-spoken competition between mother and daughters. It had all combined to have her hormones gathered, just waiting for release, and this man had opened the gates.

His hand returned to her crotch and Ellie still did not resist his touch as he rubbed his finger harder, finding that her clit had made its debut for the evening. Her hips begin to squirm slightly and her breathing noticeably changed. Ellie closed her eyes tight and her mouth began to twitch. She wanted to resist, but the want to cum was greater and she surrendered to the flame that had built within her. The mouth twitch overspread her body and she shuddered once and moaned as she came with three minutes to spare on the timer.