A Randy Retirement Pt. 08: Anya

Randy maneuvered her to the end of the couch and flipped her backwards over the arm so that her hips rested on it and then he pulled her legs so that her lower back rested upon it and hooked her thong and removed it. She had shaved her pubic hair in a small, tight triangle and her inner labia lips were thin but engorged with blood below a heavily hooded, but small, clit. He gazed at her and put the thong to his nose and sniffed.

"Hmmm, seems like someone is creaming," and as she started to reply he bent and shoved the thong into her opening mouth with only an inch or two left out. "That stays there," and her face turned lustful.

He straightened and noticed her eyes, now wild with want, and told her, "To the victor goes the spoils," and he plunged the full length of his massively thick cock into her pussy in one stroke.

Anya arched her back and let out a muffled scream as without hesitation or preamble Randy began to pound her, alternately watching her pussy gape around his prick and then her face as it contorted with each stroke.

She cussed him with every cuss word known to man around the thong, but sprinkled it with garbled exhortations to not stop and professions of need. Suddenly the bet seemed to not matter as it became evident that the only thing her mind and body was focused on was cumming.

Randy stopped and left himself fully inserted inside her and smiled at her.

Defiantly, she spit the thong from her mouth to the floor, "Nooo!" she hollered at him. "Don't stop now mutha-fucker, make me cum!" she demanded.

"What about the bet Anya?" he asked stoically, ignoring her display of disobedience.

"Fuck the bet," she replied as she brought a hand up to work her clit furiously, "I told you dammit, I'm horny."

"You'll be mine all weekend if you lose," he smiled at her.

"Anything you want, just please make me cum. I need it Randy."

He withdrew his cock and pulled her up by the arms and then walked her to the curved glass wall of the living room. Facing the ocean, he forced her to spread her stripper heel clad feet, "Bend over and put your hands on the glass."

She turned her head sideways and did as she was told, her cheek touching the cool glass and her back parallel with the floor. He grabbed her hips and reentered her completely, again in one stroke, but this time long-stroking her fast and hard going in and slow and easy coming out.

Anya's breathing began to match his strokes, inhaling sharply when he went to the root inside her and exhaling slowly as he pulled out. He watched her reflection in the glass as he withdrew and her head was pulled away from it, her upper lip curling with desire while her orgasm built.

When she plateaued for several strokes be squatted, grabbed her knees, and lifted her into the air, raising her up off his cock almost entirely and then letting her slide down hard on its length again. She put her left arm around his neck to support herself further and her breathing became more frantic. Randy's intuition told him that this cum was going to be a gusher and as he felt it commence he pulled Anya off his long dick and pointed her pussy toward the windowed wall, where she squirted what must have been a pint of her juices all over the glass and repeatedly moaned over and over, "Oh god!" in a very loud voice as she bucked in his grasp.

He slowly lowered her to her feet and wrapped both her breasts in his arms for support, cupping them in his hands as her chest heaved.

"I've, I've never done that before," she panted and then she started to laugh as she looked at the liquid slowly seep down the glass. "I'm sorry about your window. god what a mess."

Softly he told her, "It's fine, don't worry about it. Was it worth losing $50,000?"

"God yes," she said while she still sucked in air, "besides, you can't lose what you never had."

She continued to reacquire air as he released her and she bent to place her hands on her knees and inspected the juices running down her legs before looking up at him with a smile, "What now Master?"

"No, no," and Randy picked her up in a cradle and carried her to his bedroom, "I don't play the Master thing. I may dominate you, but you don't have to call me Master, okay?" and she nodded with bliss on her face. He did not stop in his bedroom, instead, he dropped her feet to the floor at the pocket doors on the far side wall and then led her through an air lock into his playroom. There was a stripper pole in the center of the room, and he snatched up a pair of handcuffs and turned her to face him.

Bringing her hands up between their faces, he asked her, "How old are you Anya and don't lie to me 'cause I'll know if you do."

Looking haughtily at him through the split in her upturned wrists as he clicked the first cuff closed, she said, "Twenty-five. How 'bout you?"

He snapped the second cuff closed and then tightened both further and she winced as he replied, "Me? I'm a fossil, what does it matter?" She made to reply and he put a forefinger to her lips and said, "Shhhhh, don't, I'm not really mad, in fact I found it funny," he admitted and then continued, "I'm 54 Anya and I like to fuck rough and sometimes I like to use toys and bondage and introduce a little pain to spice up the pleasure. But the main thing I like to do is make women cum," and he bent to remove her stripper heels. Once off, he attached her wrists high on the pole, so that she had to stand on tiptoe. He landed a hard slap on her right ass cheek and she flinched but made no sound.

As he rubbed the reddening spot, he commanded her, "Count, Anya."

She looked back over her shoulder at him and defiantly said, "One," and he immediately spanked her on the left ass cheek.

"That's for playing games with me at the pizza place," and she flinched and softly cried out, "Two."

He spanked her right ass cheek again, "And that's for thinking you were gonna charge me money to fuck," and she again flinched but tried to steel her determination as she counted "Three" in a shaky tone.

He slapped her left cheek again with a roll of his wrist as he did so, "That's for spitting the thong out of your mouth."

"Four!" and her voice cracked.

"And these are because you have a luscious little round ass on that tight body of yours and I want to turn it red," and he begin to quickly spank her ass, alternating cheeks and making her dance as best she could on tip-toe as he held her stomach with his other arm. Her breathing turned irregular as the heat from her ass spread to the rest of her body and she did her best to keep up with the count.

He enjoyed the shake of her ass that came with each lick, but paused when she counted to twenty and began to rub her ass and her whimpering melded with the fruit of his labor. "That's very good Anya, very good. What number did we stop at?"

With a tremor of both pain and anticipation, she managed the word, "Twenty si, er, I mean twenty Randy."

Ah, yes, twenty," and the current rub of her right ass cheek turned into a sharp slap and she jumped, her right foot briefly leaving the floor.

"Twenty-one," she counted while trying to inhale and twisting her head and neck slowly in a tight grimace of effort to absorb the pain.

The last four smacks of her ass were the hardest yet and each was followed by a massage of the strike zone as she increasingly sucked air in a futile attempt to quell the fire in her ass.

When he finished, he moved her arms to a lower attachment point on the pole, so that they were barely above her head and her feet were flat on the floor.

"Such a good little whore," he told her as he lightly ran a hand down her back while tweaking and then twisting her nearest nipple with the other hand.

Anya rose on her toes again as he twisted and squealed, "Fuucckkk me!"

"That's the plan pet, that's the plan," and he took station behind her, running his dick up and down her ass crack as he brought both hands around to her breasts and began to massage them in unison.

He let his cockhead briefly get caught on the bottom of her reddened ass before it would free itself and slide up the outer edge of her crack and she began to beg for him to put it in.

Briefly pulling her back into him by her breasts, he whispered in her ear, "You're a smart business girl Anya, figure it out," and he pulled her back off of him by her nipples and resumed letting his cock tease her.

After a moment or two, and a fit of impatience, she spread her legs, bent her knees, and used the slack in her arms to arch her back and his cock slid home into her sopping wet pussy.

"Ohhh, yes," she cried, "that's what I wanted," and she closed the eyes in her upturned face and began to moan loudly.

Randy reached down without missing a stroke and closed her legs, tightening the fit and she cried out hoarsely as he pounded her. He noticed the bounce of her small breasts in a mirror, how they deformed and reformed with the pounding of his dick.

He reached to her neck and roughly pulled her head back by it, the sound of her breathing growing rougher as he continued to pummel her and she called to him.

"Oh Randy, yes!"

Releasing her head after a while, she hugged the pole and arched her back more and told him, "Oh yes, please fuck me sir. Please fuck me."

Randy briefly thought to himself, 'I guess she can't help it with the sir thing,' and continued his assault on her pussy.

He reached down and picked up her left leg, turning her sideways and putting her foot over his left shoulder and resumed fucking her hard as she turned to look into his eyes, their heads touching.

Anya's lips curled and she tried to speak while sucking air, "Oh my, yes, yes."

It was when he reached down and massaged her clit that she spasmed on his dick and squirted again down both of their legs. This spurred Randy's own orgasm and he removed his cock from her quivering pussy and shot his load onto Anya's body as she tried to bend to catch his sperm with her mouth.

Afterward they showered together and she blew him, taking his entire length down her throat and making him cum again. They slept in his bed tightly entangled with one another.

*

Sunday morning Randy awoke and found her lying with her legs angled across him and her head at the far corner of the bed. He was horny and wanted her ass, so he slipped from underneath her and, taking both her ankles together and holding them up, he began to lick her pussy to awaken her. Occasionally he would let his tongue swipe her asshole and as he began to taste the saltiness of her juices she stirred.

"Oh god, do you ever stop?" she purred as he licked from her ass to her clit and sucked on the latter. She sharply drew in air with a hiss and tried to reach his face with her hands.

"I want your ass Anya. Just warming you up," and he spanked her lightly as he released her legs. "Now be a good whore and go to the bathroom and clean yourself out for me."

Anya cocked her head at him, but obeyed; returning in ten minutes and crawling onto the bed to suck his cock as he lay on his back.

She spent the better part of five minutes going down on him completely and when he was fully erect she continued to jack him as she played with the strings of salvia on the head and commented, "You know, I've had black men in my work, but none this big. You are an anomaly."

"No, I'm a fossil, remember?" and he rose and pushed her onto her back. Again he took both her ankles in his hands and pushed her legs into the air, bending to spit twice on her asshole.

She cooed as he lined her up and pressed his dick into her ass, never relenting until it opened to receive him, and she curled her lips and hissed as he entered. Once again, he was not gentle as he set off pounding her pert ass with his cock, using her legs in his hands like a pump handle to work deeper into her. She cussed him and implored him and at times mumbled garbled cries as the heat rose in her face and her body surrendered. Finally he relented and slowed, Anya's cries turning back to cooing until she pushed back on his hands hard with her legs and he released them.

Anya disengaged her ass from his cock and spun to take it directly into her mouth, sucking him to the root for several minutes and wetting it completely. She rose and placed her lacquered nails on his chest, pushing him down to the bed and mounting him cowgirl.

"You won the bet, but you can't control all the fun," and she reached behind her and inserted his still hard cock into her ass, riding him anally with her knees on the bed. Randy wrapped one arm around her waist as she ground into him and with the other hand he directed her left nipple into his mouth and suckled it hard.

After several minutes he grabbed her ass with both hands and tucked his legs to roll her over to her back with his cock still inside. He then exited her and used his hands on her hips to encourage her as he simply said, "Doggie," and she rolled to all fours.

Once again, he spat twice on her ass and then plunged deep inside and held it there for a full minute before pounding her again. He watched as the darker region of her asshole expanded when his cockhead neared it and then sucked in on his downstroke.

Eventually he slowed slightly and reached under her to work her clit and set her on her way to her first orgasm of the day.

"Oh, yes, yes. Cum in my ass," she told him as she began to lose control and her hips quivered. Her orgasm was strong and her whole body spasmed when Randy shot a ton of sperm into her ass, but she did not squirt this time.

Anya went flat on the bed and Randy followed before rolling off to her side. She had her head buried in the sheets as they regained normal breathing but eventually turned it in the crook of her elbow and eyed him with her left eye.

"Shower?" he asked.

She took a moment before replying, "No. I want to feel it in me," and she hesitated again before continuing, "I need to go back to my hotel and get some things but I'll be back, I promise."

"Un-huh," Randy uttered, not believing a word, but he made no effort to stop her as she rose from the bed and headed for the kitchen.

"Honest. A bet is a bet and you won. I'll be back for dinner," and she was gone.

Randy heard the front door open and close several minutes later and rolled to his back. He thought to himself, 'She'll probably be in Virginia and headed north by sundown,' before heading to the shower.

*

It was five o'clock in the afternoon and no sign of Anya. Randy went to the kitchen and decided on a salad for supper. He grilled some chicken tenderloins and was in the process of cutting them for the salad when the doorbell rang and he was surprised to find she had returned.

She stood with a bag in her hand, dressed in a white collared shirt that was tied at her midriff but not buttoned, revealing a black half-bra that left her nipples exposed. She had on cut-off blue jean shorts and cowboy boots and smiled at him as he stood aside for her to enter. She sashayed past him and ran a finger along his cheek, "Told ya I'd be back. I ain't giving up another shot at that cock"

He split the salad with her, and they ate at the dining room table with a view of the Atlantic and Anya kept giving Randy occasional views of her tits as she teased him. He had to give her credit; she was very good at her day job.

When they had finished and put away the dishes, he flopped a dishrag down on the counter and looked at her. "I really didn't think you'd come back."

"Why?" she asked, a certain smile on her face as she sauntered up to him and played with the buttons on his shirt.

He shrugged, "I don't know, it just didn't feel like you would when you left in a rush. It was like you'd had enough rough stuff and were cutting your loss."

Anya watched her hands undo his buttons and then smiled naughtily up at him, "How about being a little rougher tonight?"

Randy's faced did not change as he momentarily considered her request before answering, "I think I might can accommodate you, if that's what you really want."

She had finished with the buttons and moved his shirt down off his shoulders before bending to nibble on one of his nipples with her hands at his waist. He exhaled loudly and brought her hands and head up to his face, Anya encircling his neck as he released her hands.

"What I want is to feel you. All the way on that long drive when I go back to New York on Tuesday," and she licked his lips and kissed him roughly.

Disentangling from her embrace, he led her back to the playroom and under a chain hoist at the far end where she faced away from the center of the room and stared at herself in a mirror a few feet away.

Without speaking he tightened leather cuffs on her wrists and attached them to the hoist, raising them just above her head. He stood behind her and rubbed her firm ass through the faded denim as he breathed forcefully on her neck and then blew lightly into her ear. It had an effect as Anya worked her mouth to maintain her composure.

Randy slowly worked his hands up her sides, his fingers lightly touching her in almost a tickle until he reached her tied white shirt and he spread the opening and exposed her tits that stood out over the half bra. Her nipples were hard and he tweaked them roughly. Half turning her head to look at him out of the corner of an eye, she bit her bottom lip and his dick leapt in his pants.

He bent his knees and ground his hardness into her ass as he continued to work her nips, encouraging them to further erection, and Anya tilted her head up and let out a whimper as she matched his grinding.

He suddenly left and she searched for him in the mirror, perplexed by the abandonment. She saw him return from what must have been a storage room and he was now naked with something in his hands and she wiggled her ass to hurry him as she looked at the reflection of his huge cock and licked her lips.

Taking his place again at her back, he reached around her and untied the shirt, letting it hang open. He then used both hands on her left nipple, one to tweak it and the other to attach a rubber-tipped tweezer clamp, sliding the retainer ring up tight against her nipple. He had trapped most of her aureole outside the clamp and despite the rubber it was a painful squeeze. She squirmed against his crotch and furiously sucked in air between her teeth. The same sequence was repeated with her right nipple, including the sucking of air, and he lightly tugged the chain connecting the clamps and caused her to squirm further into his crotch.

"I think it's time we dispensed with these," and he reached to unsnap her shorts, dragging them down to her boots and trapping her legs together. He momentarily stopped to admire her nipples as they stuck out from the clamps at least an inch. They were growing red and the look of her face told him it was time.

He bent her forward and pushed the hoist away toward the wall in the same motion and she let out with a soft "Oh," and bowed her head. Looking down he saw her pussy lips trapped by her thighs and he inserted two fingers and began to work them deep inside, her wetness making the passage easier. In less than a minute she raised her head to look at him in the mirror and whispered, "I'd rather have your cock inside me."

Randy obliged her, grabbing her hips and working his dick into the tighter fit of her pussy. After he had his cockhead inside, she bent her knees and allowed him greater access and with bated breath she told him, "Pound me and don't slow down until we both cum," and then she steeled herself for his onslaught.

What followed could only be termed as an attack. Within the first five minutes Anya came hard and screamed in ecstasy but Randy did not relent. Instead he grabbed her shirt and used it for leverage on her body and continued pounding into her, even after the shirt began to rip. When Anya's next orgasm came she had tears in her eyes as he didn't slow the pounding of her pussy and her squirt forced its way out around his cock.