A Randy Retirement Pt. 28: Halley & Gabbie by Bamboo29,Bamboo29

“I’m glad,” he replied, “I enjoyed myself immensely as well.”

“What happens now?” she asked him.

“If you want to continue, you text me and ask if I’m free. If I am, then we set aside some time to spend together.”

“As much as I want?”

Randy shrugged, “As long as I’m free,” and he noticed Halley’s lights in the driveway.

“You’re retired, when aren’t you free?”

“You might be surprised Gabbie.”

Halley came in then, leaving the front door open as she stood framed in the outdoor lights streaming through it. Little sister gave Randy a quick kiss on the cheek and headed out.

Randy couldn’t see it, but she was beaming at Halley as she left for the car, stopping only to whisper, “Thank you” to her sister.

Halley watched her go and turned silently to envelop Randy in her arms and kiss him deeply. Then, still without saying a word, she traced her fingernail down his cheek, leaving a trail of fire, then turned on a booted heel and swaggered out the door.

***

Monday

Randy was not surprised when he got a text on Monday morning, asking if he were free that afternoon. He told Gabbie what time to come, and she arrived at his door just before one in a white cotton sundress and flip-flops, a large beach bag in her hand. She had overdone the blue eye shadow and mascara, but somehow it worked.

“Halley dropped me off. She’s covering for me with mom and picking me up at five.”

Randy nodded. “Subtract an hour for recovery and clean up, that’s leaves three hours to fuck. Do we need to talk first, baby girl?” he asked her.

Gabbie smiled sheepishly at the nickname, “I do have one question.”

His head rotated slightly to the left, while his eyes locked on her, “Shoot.”

“Why do you fuck so hard?”

Without cracking a smile, he replied, “Because I want you to feel it, even after it’s over. Do you not like it?”

“Oh no, I do. I was just curious why you fuck me like a maniac,” and she smiled at him.

“That’s it, nothing else you wanna ask?”

“Nope. Not unless you need to tell me something. Otherwise, I’m good.”

“What would you like to do?”

“Go to your bedroom,” and the sheepish smile turned lurid. “You know, you succeeded. I can still tell that you fucked me.”

Randy extended his hand toward his office door, “Your sister recently told me something similar.”

“So, how do I compare to my older sister?” she asked coyly, standing her ground.

“Oh no, we’re not playing that little game,” he declared.

“Why not? I need to know how I stack up don’t I?” and Randy couldn’t decide if she were being serious or playful.

“Baby girl, you are well on your way,” was his only reply.

“Well on my way to what?”

“When you figure it out, you’ll know,” and he once again extended his arm toward the office door, a little more insistently this time.

Gabbie shrugged and headed where she had been directed. Once inside his bedroom, she slipped the thin straps from her shoulders, dropped the sundress to the floor, and turned to him totally naked.

“Even though one benefit of being with you is being able to feel you days later, I like feeling the real thing better,” and before Randy could reach her, she had dropped to her knees, her hands flat on her thighs. The big gumdrops on her breasts were already rock hard.

Her hands never leaving her legs, she worked her mouth around to take in his hardening cock, going to the root right away. Then she backed off and brought her right hand up to stroke it and spread the saliva she had left, her eyes focused on his ten inches as her face broke into a huge grin. Still jacking his dick, her eyes turned up, “I wanted to make sure I didn’t dream it.”

“Dream what?” Randy asked, knowing the answer.

“That I could take all of it. It’s all I could think about since I left. It’s even kept me from sleeping,” and her eyes went back to the head of his cock, and she looked lovingly at it.

“Get it good and hard Gabbie, cause it’s going in your ass first thing.”

She didn’t look at him, but her lips pursed dramatically, like she was contemplating the thing she held in her hand stretching her asshole. Gabbie visibly gulped, then licked her lips and spit on his cock before extending her tongue and taking it in again. She took away her hand, clasping it with the other at the small of her back.

“Good, very good. Just think, the little cock whore inside you has been hiding all this time baby girl,” and Randy suddenly closed his eyes as he felt the first pang of pleasure from her throat.

When he opened them, Gabbie was still throating him enthusiastically. Her eyes were on him and the slightest hint of a smile appeared on her distorted face, the nostrils flared and her mascara had smudged from her eyes watering.

Randy let her continue until he was on the verge of cumming, then stopped her. The makeup had run more, turning her cheeks blue just below her eyes. He took her to his bathroom and instructed her on how to use the anal enema attachment to clean herself.

“I want you to take note, whenever you come to me, you should be ready for my cock in your ass.”

“How? I don’t have anything like this,” she asked holding the ribbed black silicone phallus out toward him but being careful not to let the stream of water wet the floor outside the shower.

“I have a travel model, one that isn’t too big for you to secret away someplace. You just fill it with water, screw to top on, insert the nozzle, and squeeze. It’s kinda like an old hot water bottle, but a lot smaller.”

“A what?” she asked.

“Never mind, you’ll understand when you see it.”

He shook his head and stood, holding out a towel to dry her lower body.

When they reentered the master bedroom, Randy positioned Gabbie on all fours on the edge of his bed, her knees spread and barely on the mattress. He filled a lube shooter syringe twice with lube and greased her butt deep, with Gab commenting on how cool the liquid felt.

“Put your hands back and spread your ass cheeks,” he commanded, and she did without fail, although he had to reposition them for the maximum effect.

She started cooing “Oh” when she felt him move in and repeated it as he pressed the head of his cock against her anal ring. Her voice got louder as he pushed harder, then got softer when he retreated. On the third try his cock slipped inside and Gabbie yelled, “OH!”

“You good?” he asked.

“Yeah, go ahead,” she told him with gritted teeth and then she flexed her ass.

Randy shrugged, thought ‘Damn’ to himself, and began inching his cock deeper. At no point did he hit a snag, pushing his entire ten inches slowly into Gabbie’s ass until he hit bottom.

When his got cock fully inside, Gabbie extended her neck and her body followed. “F-U-CK!” she bellowed loudly, with a distinct and emphatic enunciation of each phonetic sound.

He was amazed, but the time to think about it was later; right then he started to pump her asshole.

The ‘Oh’s resumed as he increased his pace and Randy eventually responded by yelling in the heat of it all, “Oh fuck yeah!”

Her head was turned to the left and he could see her mouth getting all bent out of shape, but she kept her hands firmly on her ass, continuing to spread her cheeks.

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