A Randy Retirement Pt. 28: Halley & Gabbie

"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.

"Oh yeah ... oh ... ahhh ... oh fuck me, oh god I love it," she moaned as Randy began to make the bed shake.

"You love it in your ass?" he asked.

Breathily she repeated, "I love it in my ass."

"You're my little fuckin' whore?"

"Oh yeah, give it to me," she cried.

Randy slowed then, withdrawing completely, and holding for one count before plunging back in fully, then repeating the action. The continual opening and closing of her anal ring drove Gabbie wild and she began to cry out even more.

When he finally resumed, he went straight to a steady 4:4 timing and Gab's hands moved in front of her to grab the sheets and hold on. Her head came up from the bed as he rocked her world and she constantly cried out "Oh."

Randy watched her bubble butt jiggle under the onslaught of his cock and asked, "So I take it that you like getting fucked up the ass?"

"Oh god yes, fuck me ... oh god I love it ... give it to me," Gabbie moaned as her head wobbled back and forth.

"You my fuckin' whore?" Randy asked.

"Oh yeah, ahh."

"Yeah? Say it, say I'm your fuckin' whore," he demanded.

Without delay Gabbie responded, "I'm your fuckin' whore," drawing out the last word for at least three counts while she put her hands behind her back, inviting him.

Randy wasn't one to turn down such an invitation. He pinned her hands to her lower back and power-fucked her hard from behind. The sight of her ass clapping on his cock with every downstroke spurring him onward.

When Gabbie came, she moaned uncontrollably, her words unintelligible as her body quivered. Randy was so close to nutting that he kept pounding her ass until he felt his balls well up and then pulled out. He reached down and grabbed Gabbie by the hair, turning her around by her blonde tresses to his cock.

With her eyes closed and tongue extended far out of her open mouth, he plastered her face with several thick, white shots of semen as she propped herself up with her arms. Gabbie was totally out of it, overcome by her orgasm, as he rubbed his dick all over her open mouth, tongue, and cheeks to spread his seed. One last spurt blasted her face and found her flared nostrils.

Opening her eyes, Gabbie exhaled heavily through her nose and a wad of the last cumshot found her philtrum and stuck there. She brought her hands to his dick and began to clean it without instruction. Through it all, she paused only to stick her tongue out and attempt to lick the wad of cum from her upper lip. Eventually, she had to get it with a finger and then went back to sucking.

"My, aren't we the natural," Randy smiled down on her, his hand brushing back her hair.

Between slurps, Gabbie asked, "Natural what?"

Randy pulled her off his cock by the handful of hair, then pulled her upright and took her to his mirror.

"What do you see Gab?"

A wide grin creased her face as she answered, "Someone who's satisfied."

She turned to him, the grin still wide, and bent to kiss the head of his cock and then deep throated herself until her nose touched his pelvis, dropping to her haunches with his dick as a pivot point. Her cheeks sunk in with her effort and she sucked him clean, then slowly backed off at a snail's pace and watched Randy's face the entire time.

When she was finished, she stood, rose on her toes, and kissed him, Randy palming her ass roughly. He backed up and sat on his dresser so that his eyes would be on the same level as hers and reached out to lightly pinch her gumdrop nipples. Gabbie interlocked her fingers behind his neck, her forearms together and trailing down his chest, both elbows at his sternum.

"I don't want you to think that sex is only about the things you do with me. You realize that most people don't fuck like I do?" he told her.

"Yes, I know, but I like your kind."

"What do you like about my kind of sex Gabbie?"

"Cumming."

Randy nodded.

"And do you have a more detailed answer for how that makes you feel yet?"

"Why does that matter so much to you?" she asked.

Without delay he told her, "Because if I make you verbalize it then it will pervade your thoughts and enhance your desire and I get to do more intense stuff to you."

She paused for a moment, the mouth contorting again as her brain searched for the right words.

"The buildup to it seems like it's never going to happen. And I want it so bad, more than anything and that seems strange to me because before you, I never knew that feeling was even possible, much less that I could feel it."

She paused for a moment and Randy detected a tiny shiver run through her body before she continued.

"Anyways, after all that buildup, when I finally do cum, my mind goes totally blank. It's like, I can't think about anything and my body takes over, like, pulsating and then it completely lets go. It's like I'm melting and exploding at the same time. I don't have any control, and l don't care about anything but that exact moment. And you know what the scary thing is?"

"What?"

"Once I have cum the first time, all that matters is cumming again. It's like a drug I guess. I used to think those people who talked about getting instantly hooked on dope were full of shit, but I may be wrong if sex is anything like drugs. I can see how they can be addicted," and she reached for his cock.

"You want another fix?" he asked with a sly smile.

"Yes," she answered breathlessly and then she climbed up onto the dresser, straddling him with her feet flat on the top as Randy pushed his back to the mirror.

Gabbie had positioned herself so that his cock was behind her, rubbing against the crack of her sweet ass. She began to kiss him deeply, one of her hands caressing his face and the other on his chest as her tongue went deep inside his waiting mouth.

When she raised up, Randy reached down and positioned his cock under the gape of her pussy and Gabbie sunk, her cunt swallowing it whole. She exhaled into his mouth with a grunt and then began to ride him. It was the preliminary to the final act of the afternoon as she held onto his shoulders and pistoned her ass up and down with abandon.

Randy watched her mouth contort as she began to breath harder, her eyes flicking from his to her crotch. At the first sign of her impending orgasm, he stilled her and slid forward.

"Remember what I told you last Christmas?" he asked, and her eyes turned confused, so he reminded her. "That being short was an asset because it meant you were easier to pick up?"

"Oh yeah," she blurted as her eyes got big. They got even bigger when he hooked his arms under her thighs and stood with her.

"Oooo shittttt!" she cried out as he started to pound her cunt, her ass slapping against his pelvis loudly. Gab's eyes found them both in the mirror and she was taken by the sight of his dick slamming in to her body and shuddered in his arms.

Randy found that her facial expressions were intoxicating, simply because they revealed how much of an effect his cock was having.

When Gabbie climaxed, she wrapped her legs tightly around his waist and her arms just as tightly around his neck, her body undulating on his frame as he stilled and let her cum. She held on hard until her body stopped quivering and when it did, Randy walked over to the bed with her still clinging to him.

He sat on the edge, Gab finally relaxed enough to look at his face. Her eyes were spacey, and her mouth hung open when he asked, "More?"

She answered by nodding yes.

Twisting on the bed, he laid her on her stomach, legs together and straight. Getting on top, he sat on his knees with his ass on her thighs and reached down to spread her cheeks open.

"Fuck my ass again," she whispered.

That was his plan anyway, so Randy did, pushing his throbbing cock into her waiting asshole as she lay prone on the bed. He leaned forward, planting his hands on either side of her shoulders, his head towering over hers.

When Gab realized this, she looked up at him. Her rectum accepted his cock fully and he began to pound her, going up on his toes and using his full body weight to slam his rod deep with every stroke.

"Oh god," she groaned repeatedly, her body thumping into the mattress and rebounding up to meet the next volley, panting like a dog in heat.

When she came, she buried her face and reached back with her arms to hook them around Randy's as her body locked up and shook. Her asshole squeezed his cock so tight that Randy came then, dumping load after load into her colon until he collapsed on top of her. He could feel the seismic movement of the young woman's body as she continued to cum long after he was depleted.

*

Before they showered, he pointed out her face, makeup all over it. Gabbie laughed uncontrollably until Randy had to pick her up and place her in the shower stall.

"Why'd you put so much on?" he inquired.

Gabbie raised her palms up, "I don't know really. I think I wanted to look like a woman for you."

"Just be yourself baby girl, that'll always be good enough for me."

After they had dressed, Randy went and got the anal enema douche. It was in a felt drawstring pouch and Gabbie immediately took it out. The orange bulb was 5 inches long and the attachment the same. He showed her how to fill it and screw it together and she dropped it back into the pouch and the pouch into her beach bag with a smile just as Halley came in the front door.

Gabbie kissed him quickly and said, "I'll be sure to use it for next time," and then skipped past her sister, telling Halley in a sing-song manner as she went out the door, "I got my ass fucked and I liked it!"

Halley watched her head toward the car and turned to Randy.

"She seems happy."

"She's a natural," he replied with a sedate grin.

Halley looked at him and teased, "You don't have to be so happy about it."

Ignoring her comment, he asked, "You just drop her off and don't come in?"

"I knew if I came in, I'd have to have your cock and right now the focus needs to be on her."

"Again, I didn't realize that you and your sister were so close that you shared things."

Halley sniffed, "We shared a bedroom for sixteen years."

"I'm talking about my cock Halley."

She tried to keep the grin off her face, but failed. "I know. We grew up to be two different people. This is the most intimate thing we've ever shared between us. But like I told you, I love my sister and want what's best for her. Just don't get too attached."

Randy snorted, "There will always time for you Halley. Now, am I gonna get to see you again while you're home?"

Halley frowned, "Probably not, dammit. I have to go back tomorrow morning and we have a dinner tonight with the grandparents that I can't get out of. December is most likely the next opportunity."

He embraced her and they kissed a kiss that lingered longer than normal. December would have to do.

***

Thursday

Randy had spent almost every waking moment of both Tuesday and Wednesday giving thought to where he wanted to take Gabbie and how he wanted to take her there. He did not want to overwhelm her too quickly, but he also did not know how long she would last with his appetite and there was so much potential inside her that he wanted to tap. The inexperienced high school senior, at the tender age of eighteen, had taken his monster in all three of her holes to the hilt and aside from the initial resistance, she had done so magnificently. What's more, she had done it enthusiastically. Gabbie was truly a freak of nature.

She had texted in the morning asking to come around late that afternoon. When she got to his house, she was dressed only in a black string bikini, a can of Red Bull in hand. She had no makeup on, but was flying, fidgety, her eyes wild, and Randy asked how many of the energy drinks she'd had.

"This is the third one."

"Third one since when?"

Gabbie shrugged, "Oh, about three."

"You know those things in that quantity aren't good for you," he told her.

Her eyes blinking rapidly, she walked over to the kitchen island and picked up his pack of cigarettes, "You sure you want to have this conversation?"

'Damned sassy, just like Halley,' he thought. Her point made, he switched to the more important topic, "What time do you have to leave?"

"I have to be home by eleven," she mentioned as she left him standing there and walked out the back door to the pool deck.

Randy stood still for a moment and calculated time, then followed her. When he caught up, Gab had planted herself crossways in the free-standing hammock and was using it like a swing.

"What are those?" she asked nodding toward one of the four devices spaced around the deck. They looked like miniature streetlights, each about five feet tall.

"Electric things that zap the mosquitoes. They come on automatically as it gets dark and have a low intensity light that attracts them."

"Oh cool," she replied and jumped topics absently, "I wore this because mom thinks I'm at a pool party."

Randy walked right up to her and reached down to the strings tied in a bow on each side of her hips, "Then I guess we need to get the party started."

"That's what I'm talkin' 'bout," she replied reaching for his zipper but before she knew what was happening, he had untied her bottoms, whipped them off her ass and rolled her legs back on either side of her head.

"What are you doing?" she asked, her breathing already turning rapid as she giggled.

Randy didn't answer her, he was too busy tying her ankles to the far side of the hammock. When he finally stood, she was trapped, swinging with her ass hanging over the edge, both wrists and both ankles tied together over her head.

"We," and he put a lot of accent on the word, "are about to fuck," and with that he undressed himself while Gabbie watched, her mouth twitching.

He went straight to her ass, the initial reluctance of her anal ring lasting all of thirty seconds before it opened up and Randy speared her completely. He stood there with his cock buried and watched her mouth work, flexing his dick just to gauge her reaction.

In a voice growing desperate, she begged him, "It's been three days, please fuck me."

With that he slowly withdrew until just the head was still inside and then grabbed the edge of the hammock's webbing and pulled her toward him, his cock entering fully again.

"Yessss!" She exhaled the word, leaving her lungs vacant until Randy pushed the hammock away. At her furthest arc away from him, Gab sucked in a breath and held it while he pulled her back again. This sequence continued, Randy picking up the pace until she was panting like a dog on a summer's day and he was railing her asshole.

It took only six minutes for her to cum, her legs trying to kick as they shook, and he pulled out and untied her. Without delay he moved her inside to the living room, putting her on her knees on the couch and fucking her pussy, Gabbie burying her face into the leather cushion and cumming a second time rather quickly.

He slowed then and instructed her on how to fuck in doggy, to use her legs and hips to fuck him back. Once she got into a rhythm, he told her about her Kegel muscles and how to use them to milk a man's cock while she was fucking him. Gabbie got the hang of it right away.