A Randy Retirement Pt. 32: Gabbie

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. All stories can stand alone, but reading the series gives added insights and descriptions as it unfolds.

Synopsis: Gabbie delivers a birthday present.

November, 2018 -- River house

Friday

Randy had been on a conference call with his CPA and lawyer for an hour by nine a.m. on the second day of November. They had discussed the progress of the farm co-op and then turned to another project he had been working on that had finally closed. At 9:30 Randy drove to the lawyer's office to sign the papers on his new acquisition. Although his CPA had been leery of the move, Randy felt good.

After the signing he stopped by the grocery store and was recognized in the bread aisle by a former student.

Kristi was as tall as Randy and slim, but not skinny, with just enough curve in just the right places to make her imminently desirable. She had dirty blonde hair and made all the boys go nuts over her in school; but she never let Randy get too close, even though she took his senior year elective honors class.

Quickly he calculated in his mind, she must be at least 35 by now, but she still looked awesome, and his dick twitched as she gave him a quick hug. Randy wanted to check another box.

They caught up briefly and then he invited her to lunch.

"Thank you, but no, I don't think so." She told him.

"Why not Kristi, it's only lunch and I'm buying. We can catch up some more."

She laughed derisively, "It's not only lunch and you know it."

"Of course it is," Randy protested.

She smiled tightly, but was firm, "No, it's not. If I have lunch with you then I'm gonna need to have you and I have a husband and two kids that I can't do that to. Why do you think I avoided being alone with you back then?"

For one of the few times in his life, Randy was stymied. It didn't happen often, but there were times when he was denied. He was also reminded that there were times when he didn't get a hit off some female when there was a hit there to be had.

"I ... I," he stammered, so she continued her statement.

"Because I knew if I was alone with you for any appreciable time that I'd end up spreading my legs for you. I knew you had that power over me. I don't know how, but I knew. And I wanted to, in the worst way. But somehow, I denied myself, Lord knows how, and now, well ... I love my husband and I love my life. I don't want to mess that up, even for you."

Randy nodded in silence and Kristi added another layer and his little head began to scream at him.

"You know, I still occasionally think about you, see you when Dan and I are making love."

Randy rubbed his chin. He thought that if he pushed the moment, he could check that box, but it wasn't worth it.

"Kristi, I completely understand. I'm glad we had a chance to catch up and I wish you nothing but a happy life going forward. I'm gonna leave now, before I change my mind. Good-bye," and he immediately turned and pushed his cart away.

Just as he took his second step she called after him, "Just so you know, you still have that power." He did not look back. This time the big head won.

*

He had been in a bad mood the rest of the day from his encounter with Kristi; questioning himself. It was late at night before he went to bed. That state of being where you are aware of your surroundings but about to go off to never-never land had just arrived when his phone dinged. It was approaching 11 when he looked at the text.

'R U UP'

'At least she texted beforehand this time,' Randy thought as he told Gabbie to come on over.

She arrived dressed without a coat despite it being near 40 degrees. Instead she wore a wife beater cut at the neck to free up her bosom, no bra and black yoga pants with no underwear -- her nipples on display through the material, sweat coating her body, a camel toe plainly visible, and a can of Redbull in her hand. She was flying.

Gabbie handed him a crude 8x10 watercolor of a bowl of flowers.

"What's this?" Randy asked.

"You're birthday present."

"Where did you get it?"

"I painted it for you," she replied in exasperation and with a heavy emphasis on the first two words, as if she were offended by his question.

Randy looked again at the painting. He had thought she'd brought it as an excuse, then realized that she had really made it.

"Is painting something that you do often?"

"Some... I like to do it to free my mind of things and relax."

She pulled the wifebeater away from her chest with her fingers and shook it, then wiped a few beads of sweat from her brow. Randy couldn't decide if she were sweating from her internal temperature or the energy drink.

"Gabbie, you do know when you wear stuff like that, you make my side of the species want to fuck the shit outta you."

She went to her knees and faced away from him, then looked back over her shoulder seductively, "No, but I do know that I wanna get fucked in the ass."

Randy put the painting on a table by the front door. "You were such a shy girl, what happened to you?"

"Your cock made me cum. Now the memory of that feeling is roaming around in the back of my mind half the time and front and center the rest of the time. So, I texted this time, are we gonna fuck or are we gonna talk?" and she spun around to face him on her knees.

Randy was struck again by her very nice, pear-shaped ass as it moved out of his sight. He thought her tits had grown slightly, approaching D cup status, but still was undecided if her naughty look favored an imp or a cherub.

"You little whore. How long are you here for?" he asked her.

"All night, hope you took your nap," she teased.

"Oh baby girl, that's not very nice," he replied, instantly making up his mind what he was going to do to her in the playroom later. She had asked for more rough stuff, well, she was going to get more rough stuff.

Walking over to her, she pulled down his boxers without delay and retrieved his dick. This was the part that was definitively different, her eagerness, her passion, her whorishness. Their first times together Gab was exploring, flying blind but eager. The more they fucked, the more brash she had become and the more of the inner whore in her came out.

When his dick went into her mouth and forced its way past the catch in her throat with little effort and she retreated, licked his cock like an ice cream cone and told him, "You know, the first time I sucked you off and your cock got to that place in my mouth where it's do or die, I was scared that it wouldn't fit. I wanted it so bad. All of it. Now every time it hits that spot and makes its way on down where it belongs, it makes me hornier and my little pussy gets all wet."

"Why is that?"

"Because my body knows what's coming next," and her big, cobalt blue eyes flashed at him in mirth and she continued, "Almost every time you enter me it starts a sequence that is inevitable and unstoppable. I know I'm gonna cum and knowing it only adds to it when it happens."

He reached down and took her by the arm, getting as far as the kitchen before he forcibly made her squat before him. Her hair became more tousled as he treated her roughly, but it only stoked the fire in Gabbie as she eyed his cock and took it down her throat again, her hair wrapped around Randy's hand.

He marveled at how she gobbled his ten inches right to the root with no sign of resistance, retch, or gag whatsoever. It was something he thought he would always view with awe.

Gab slobbered all over his dick, getting it good and wet, then she gave her best impression of a sword swallower at the traveling carnival, going down on him slowly but completely. He could see the outline of her big ass in the yoga pants as she squatted low and pulled his cock downward so that she could straighten her throat and fuck herself with it by moving her body up and down.

He watched her reflection in the oven window, her ass moving as she sucked him off. She attempted to put a hand inside her pants to play with her pussy, but her stopped her and demanded her hands. When Gabbie complied, he held her wrists above her head with one hand while holding her head on his cock with the other.

"You don't get to cum until I let you cum, you little whore."

When he pulled his cock out of her mouth and let her hands go, Gab played with the line of spittle that drooped from the tip to her mouth. The front of the wife-beater between her tits was soaked, the cotton having darkened.

"I want this inside me. I need this inside me," and she put a heavy accent on her need as she smacked her lips.

"Let me get these pants off you and I'm gonna fill that need."

He left her shirt on, but got on his knees and pulled her yoga pants off abruptly, catching her legs in the air and rolling her back onto her shoulders with her feet sticking up so that he could go to the floor and bury his tongue in her twat.

Gab squealed, her feet coming down to rest on either side of Randy's neck as she palmed her boobs and looked at him working her over with his tongue.

"I've missed this," she told him, her voice halting, the mouth contorting into irregular shapes as she amped up.

Minutes later she was begging him to fuck her as his tongue almost had her ready to explode.

Randy rose and pulled her up with him, turning her roughly toward the kitchen island counter. He bent her over it with a hand on the back of her neck and then raised her left leg and put her knee on the counter. Gabbie's right foot barely touched the floor, with only the big toe and the one beside it maintaining contact as he licked her pussy one last time.

She squirmed, her head buried between her arms as his tongue lashed deep inside her, but his cock splitting the big, fat lips of her labia made her head rise and her eyes widen.

"Oh shit!!! I love you cock!!!!" she literally hollered at the top of her lungs while Randy steadily pushed the head of his dick all the way to her cervix.

Her pussy was tight, not uncomfortably so, but tighter than he expected. With her knee up, Gab's body was turned slightly to the left, so that Randy could see her breasts as they moved in time with his strokes. The sight of her nipples hardening sent a shudder down his spine as he took her there on the counter.

Again, he wrapped her long, blonde hair in his right hand and began to short-stroke her, only pulling out halfway before slamming his cock back into her pussy, her juices now flowing freely down both their legs.

When Gabbie orgasmed, it was with a weak "Oh lord" and her head and neck went limp and bobbled without control. Her toes lost touch with the floor as both legs began to quiver wildly in a motion that spread to her entire being as if she were possessed.

Randy held her body balanced on the edge of the counter, trapped between the Italian marble and his cock as the orgasm slowly subsided and then he pushed her further onto the countertop and withdrew, holding her steady with a hand at the small of her back.

After recovering from her first cum of the evening, Gabbie reached back and put two fingers deep in her asshole.

"Is that what you want?" Randy asked, watching her fingers widen her anal ring.

"Give me a sec," the young blonde replied, spitting on her hand and lubricating her ass. "Now, let me have your cock, I already made it ready for you." Her voice cracked with need.

He bent and kissed her deeply with a fistful of hair. Then he twisted her head so that he could see both her eyes and whispered, "For such a little whore, you sure have a big need."

Gabbie nodded, her bottom lipped trapped by her teeth, driving Randy wild.

He climbed atop the counter to join her, turning her over onto her back as she grabbed his dick and guided it to her backdoor.

Gab put it in with minimal effort and Randy began to plunder her asshole. He noticed that it was tight as well and it spurred him to grab her ankles and push her feet back alongside her head. With one big surge he used his hands and his cock to move the diminutive blonde further onto the kitchen counter, Gabbie crying out with groan, "Oh shit."

"You see whore, this is what happens when you text late at night," Randy growled, now up on his toes on the big kitchen island, his ten inches hammering her ass.

She could only moan in response and in seconds she orgasmed again, her body attempting to wriggle as he held her firmly in place and continued unabated.

"I'm gonna keep pounding your ass until I get off Gab, regardless of how many times you cum," and Randy shifted to 4th gear and railed her harder ... and faster ... going even deeper into her colon.

Gabbie looked frantic, her existence almost a continual orgasm as her legs quaked against the hands holding her ankles in place; and she babbled, her contorted mouth unable to form words.

Finally Randy roared and shot a torrent of jism inside her, Gab's eyes rolling back as the force of his release filled her ass.

Without delay he carried her to the playroom where he stood her up and ripped the wife-beater from her body.

She had liquid from both of their bodies running freely down her inner thighs as he sucked her nipples and held her upright by her hips.

Gabbie had ridden the V-bars before and had recovered enough for her eyes to light up when Randy backed her to them and picked her up, sitting her at the joint of the V with her legs spread insanely wide by the bars.

"We're gonna do this again huh?" she asked.

Randy kissed her harshly while holding her chin hard in his right hand and then pulled away.

"Not exactly."

He strapped her thighs to each of the wings of the V, two straps on each thigh pinning her in place, but leaving her lower legs to swing freely. Then he pulled her arms over the horizontal bar at her shoulders and straight down behind her back, strapping both arms together at the biceps, below the elbows, and at the wrists.

Standing up, he checked her pussy with his fingers, gaining a gasp from the eighteen-year-old.

"Still wet. You love this, don't you whore?"

"Yes!" Gabbie yelled, her eyes defiant, yet pleading.

Randy chuckled as he walked away. In moments he was back, wheeling a fucking machine underneath her spread thighs. It was topped with a ten-inch dildo that had three knots or bumps on it, the shaft an inch and a half in diameter and each knot two inches. He positioned the machine so that the tip was inserted between her labia, the fat lips now red and puffy from earlier.

"What's that for?" she asked, her voice squeaky, but he did not answer.

Watching her face, he twisted the dial on the control and the first bump slowly ascended into Gabbie's snatch, the sight of her pussy widening to accept it making his cock twitch.

Her mouth contorted until the bump disappeared and then Gab exhaled and seemed to relax, until the second bump began its entry and her head demonstratively dropped down to try to watch.

She could not of course, but as the second bump slowly disappeared inside her Gabbie's head rose toward the ceiling and she let out a howl of pleasure. Randy stopped the machine, not letting her take the third bump.

He left her again and gathered more items and on his return, he watched as she attempted to squirm while bound to the V-bars with the dildo impaling her. Gabbie did not even notice the rubber-tipped, duck bill clamps until the first one closed on her left nipple and her eyes shot to her tit as she squealed.

"Feels good, don't it?" Randy asked, but she did not reply. Instead, Gab began to pant softly.

Her eyes followed him as he clamped the other tit and then tied long lengths of twine to the hook on each clamp, pulling over the winch when he was finished and running the twine through a steel circle on the end of the cable. Holding the loose ends, he raised the circle to the ceiling and then tied the end of each length of twine into a noose.

"You ever been fishing?" Randy asked her and Gabbie nodded furiously, her eyes now bloodshot.

Holding out both of his hands, he showed her the eight-ounce, pyramid shaped fishing weights in each of his palms, "Then you know what these are, right?"

Again, Gab nodded yes.

"Guess where they are going."

"Oh no," she managed to say as her eyes widened while watching him reach for the nooses and attach the weights, one to each length of twine. Randy's head turned to her as he simply let go and the weights dropped and swung, snatching her nipples up and stretching her tits.

"Owwwlllll" she squealed and squirmed, her body writhing on the dildo inside her.

Without delay he reached down and turned on the machine, the third bump immediately pushing against the walls of her vagina until it too disappeared. Randy set the machine so it would slowly fuck her, the dildo moving in and out at a rate of an inch every three seconds. When it reached the limits of its depth the machine would begin to lower the dildo, Gab's pussy lips extending down grotesquely as each of the bumps exited her in excruciatingly slow motion. It would stop with the tip still inside and then begin to ascend again.

For five minutes this continued, Gabbie panting slowly. The view of her breasts being strung up was magnificent, and every time her body would jiggle the weights would spin and bounce. Before he left her for two more items, Randy turned the machine up, making the dildo move at a rate of one inch per second.

When he returned Gab's breathing had shifted to fast and shallow, her mouth hanging open as her eyes continually shifted from her crotch to her tits. He also noted that her toes were curled tightly. She was moaning as she panted, and he could tell that she was concentrating in an effort to orgasm.

Randy had brought back an inch-wide leather belt with a single steel D-ring. He walked to the side and placed it around Gabbie's neck, looping the end of the belt through the D-ring and pulling it tight before he set the fucking machine on high.

Now at a rate of an inch every half-second, the machine was pounding Gabbie, her body being moved upward with each ascent and pulled downward with each descent. Randy controlled her breathing with the belt, her face turning redder and redder as her body surrendered.

When she climaxed the first time Randy held the belt tight as her body jerked wildly and thrummed, the fishing weights performing a ballet of jumps and spins. When he relaxed the leather, she sucked in air greedily and almost immediately came again, her eyes wild as if she were high.

"How's if feel baby girl?" he asked her, but Gabbie did not reply. She was in her own little world, a world of constant orgasm as the machine continued to push the bumps inside and then pull them out.

The blonde's head had lolled forward during a brief interlude and Randy pulled it back upright by tightening the belt and immediately putting a Hitachi directly on her clit.

"Ohhh fuukkkkk," she managed to gurgle as the tremors immediately commenced again.

*

Gabbie had cum two more times before he shut the machine down and removed the dildo. Natural lubrication from her pussy ran freely down the silicone phallus as he moved it aside.

He took the worn out eighteen-year-old from the V-bars and laid her on her stomach on the floor while he went and retrieved the things he needed for her next encounter.