A Randy Retirement Pt. 29: Anya

*

Diane the hostess greeted them and Randy gave her a discreet, one-armed hug as he introduced Anya. The expensive consort from New York, soon to be California, looked spectacular in the leather skirt that showed plenty of toned leg, a pair of black stilettos, and his white shirt. She had selected an old tuxedo shirt that he had forgotten about. It was cheap and had buttons instead of studs, though Anya had left the top three unfastened. As was her style, the makeup was heavy; but she looked dazzling.

They had a wonderful meal of local catch fish and she told Randy that she could see why he liked the place so much.

Afterwards he took her to the pier for a stroll. It was windy from the approaching storm, and thus chilly. One could tell that her nipples were hard enough to cut glass as they tented the fabric. Without regard to those who may have been watching, Randy checked them when they got to the end of the pier, grasping them hard through the cloth and pulling up until Anya's body rose.

"That wasn't fair what you did to me this afternoon," she told him through gritted teeth.

Randy smiled.

"Really? Have you not been on a slow boil ever since lunch?"

The woman, who could easily make a grand an hour giving some other guy the 'girlfriend experience', licked her lips and gave him a one-word answer.

"Yes."

"Then it served its purpose, didn't it?"

*

In the car on the way back Anya did her own checking, pulling out his cock and playing with it for the entire thirty-minute drive.

They had barely gotten into the house and walked toward the kitchen when Randy grabbed her from behind and pushed her back against the wall, his hand squeezing her throat. There were a few night lights on, but otherwise the house was dark. Even so, he could see her sneer at him, the lips curling.

With no forewarning, he put both hands to her collar and ripped the shirt open, buttons clattering to the floor as Anya latched on and kissed him roughly.

Randy spun her around, their eyes locked together, and he pulled up the leather skirt while maneuvering her backwards toward the dining table. He had the skirt bunched around her waist by the time they got there, the dress shirt he'd had her wear ripped and hanging in tatters, exposing her small round breasts.

Anya bit his bottom lip and nearly brought blood as she pulled back from the kiss, her eyes smiling at him from less than two inches away and then Randy lifted her onto the table.

"Let's see how flexible you are," he growled as he pulled her right leg up and she lay back, her hands over her head and limp on the tabletop. Her left leg followed, Randy putting both her ankles behind her head, and she brought her hands in play to hold her ankles in place.

"Impressive," he stated, straightening. "Here's the deal, if you let go, you don't get to cum."

He saw her face change to a look of shock, replaced instantly by determination. Stooping to lick her labia, he palmed her ass, then spent considerable time laying the groundwork for what he intended.

Anya began to pant and then squealed "Oh god," as he sucked on her clit. He tormented the little nub that, like the rest of her, was thin but hyper-sensitive and Anya's demeanor turned to one of desperate need quickly.

When he decided that she was primed to the point of breaking he spit several times on her asshole and then straightened and looked down at her.

"Open wide," he ordered and when she did, he reached over and took a red apple from the fruit basket, stuffing it deep into her mouth and locking it open.

Anya moaned as his hands found the underside of her knees and pressed down, her ass rotating up even more as his cock contacting her well-worn sphincter. Slowly he pressed it home, her ass opening to him as her eyes widened and her moaning grew.

He pulled her body toward him by her legs, so that her butt hung off the table and then began to slow-fuck her ass, ten inches in and ten inches out. In time he straightened so that he could drive his cock deeper. Anya kept her legs in place and tried to moan around the apple. The red fruit covered much of her lower face, hiding it from him as her eyes fluttered above it. His thumb found her clit, flicking it roughly and her moaning grew more insistent and fractured.

The fine alabaster skin shone in the dim lighting, a luster of sweat coating it. The constant moaning through the apple provided a lewd soundtrack to what should have been a painting, she looked that grand; and still, through it all, the unrelenting cock moved in and out of her ass.

When Anya was about to climax, she involuntarily bit hard on the apple and it fell away, tumbling off the table to the floor. She spit out what she had bit off and all but yelled, "Oh god yes, make me cum dammit!" as the first wave came ashore and her asshole clinched on him.

"Damn, your ass likes my cock," Randy panted, sweat dripping from his bald head as his body continued to rock.

"MY ASS LOVES YOUR COCK!!!" she shouted, fighting to keep her legs in place during the height of her orgasm.

Randy continued to rock her ass until he reached satisfaction, taking his cock out to spray several cumshots over her body. Anya still managed to hold her legs in place while the moaning continued.

Without giving her respite, he put his cock in her pussy and ran his arms around and under her body, locking her legs in place between them as he clasped his hands together. Bending his knees, he pulled her off the table and then lifted Anya up, walking with her to his bedroom while she wiggled her upturned toes in joy. She rode him there for another hour, Randy imploring her to "giddy-up," before they both came again. Then they showered, changed the sheets, and bedded down for the night.

***

Sunday

Randy woke first on Sunday morning and lay there studying how much Anya had noticeably aged in the last two years. The lines on her face just now becoming more pronounced, the effort to stay in shape further refining her face and revealing her bone structure.

But the most telling factor was her holes. Both her pussy and asshole showed signs of heavy use, with her taint prominent like a land bridge between the continents of her butt cheeks. Her asshole was depressed and now sat in what could best be termed a divot. She was a well-worn whore. But that had its advantages. She knew how to fuck and suck, and she relished it rough.

Randy couldn't resist and began to eat her out while she slept, Anya eventually stirring and moving her hands between her legs where he had latched onto her clit with his teeth and was bathing it with his tongue.

"Oh god," she groaned in a decidedly horny voice. "I haven't awakened this turned on in a long, long time."

It turned it into a sixty-nine with Randy on top and though she never took all of him she did remain locked on as he cum in her mouth, his hips spasming with each jet of hot spunk he could muster.

*

Together, they made a chef salad for lunch since they were going out for a big meal at dinner.

Randy cleaned the table and excused himself to get the trash ready for the collector on Monday morning and when he came back in, he noticed that Anya had disappeared. He thought nothing of it and busied himself straightening up the kitchen and living room. Fifteen minutes later she still was a no-show and he decided that he had better check on her.

He went to his bedroom and, as soon as he entered, heard her sultry voice.

"It's about time."

His head turned to the right, where Anya had situated herself sitting up against the headboard with pillows behind her head and back. Her feet were spread with knees bent and she had a thong playfully in her teeth. He continued deeper into his bedroom and turned to take her in, the ice gray eyes full of mischief and her pussy gaped because she had obviously been playing with it.

"Come fuck me," she said, the sultry voice again, and it was enticing.

"One moment," he told her as he held up both hands, each forming the shape of a gun. He departed for the playroom, returning with lots of rope and a blue foam, wedge-shaped pillow.

"Oh, I think I'm gonna like this," Anya cooed as she flung the thong aside.

Randy crawled onto the bed and grabbed for her, capturing her feet, and pulled her legs until her body was dead in the center of the bed. He sat on her stomach and took each wrist separately, securing them with hemp; then tied them straight out to her side and secured the rope to the support railing underneath the mattresses. He paused to place the wedge under her lower back, and then pulled her ankles straight out to her sides and tied them off in the same manner that he had her wrists. She was spread wide, her legs almost in a full split with very little leeway in the ropes. The wedge held her ass seven inches high so that her sex was continuously presented to him.

Standing up and backing off, Randy held his chin in his right hand as he studied his work. Without speaking he then turned and went back to the playroom, Anya calling after him, "Wait! Where are you going? Come back here you fucker!!!"

Her voice had changed. Gone was the sultriness and in its stead was a tone of want, need, desire.

When Randy rushed back into the room, she was still yelling at him. He blitzed her like a linebacker unabated to the quarterback, a flogger held high in his hand until he brought it down in the middle of her rant and her words turned into shrieks as the strands of the flogger found her exposed pussy.

Anya's body jerked as her limbs took up what slack he had left in the ropes; her hands having gripped the rope on her wrists so she could pull on it. Each time he landed the flogger on her mons she bellowed, the veins in her neck standing out. But her voice belied her, as it revealed her yearning.

She began to anticipate the strikes, her hips rotating up to meet them and Randy smiled when he noticed it.

He got on the bed between her legs and ate her out, her pussy already dripping, and when he first sucked her clit, her back arched up off the wedge and she sighed the most needful sigh he had yet to hear from her.

Randy sat up, his fingers replacing his tongue, "My, aren't we the needy one."

"FUCK ME!" she demanded, her pelvis trying to fuck his hand as she tilted her head toward him, every vein in her neck about to pop.

Picking up the flogger, he whipped her once on her exposed cunt as hard as he could, extracting a scream from her that did reveal pain as her body tried to rise off the bed.

Before she could recover, he plunged his cock in her snatch, pulling on the tops of her hips with his hands as he drove into her hard and fast. Each time she got close he would stop dead with his cock fully inside. He could feel her heart beating through his dick.

She cussed him some more, but as he continued her tone softened, until she was whimpering and desperate, needing out badly.

It was only then that he made her orgasm, starting slow and building up until they both reached crescendo in unison, Anya bridging up as he emptied his balls up against her cervix and held her squirming body in his hands by her hips.

He pulled out and reached for the flogger with his right hand while inserting the first two fingers of his left into the maw of her cunt while she was still bridged, her head swimming. With his left thumb he started to massage her clit as his fingers worked her over inside and she cooed.

Her body had just started to lower when he struck with the leather, lighting up her abdomen and tits and Anya immediately started to cum again, returning to the bridged position as the leather wrapped around the curves of her body.

Afterward he untied her, and they cuddled for a couple of hours and made small talk.

Just after four he asked her, "How long will it take you to get ready for dinner?"

"About an hour and a half."

"Okay, I was just figuring out timing in my head. We probably need to get cleaned up and start getting ready if we want to eat before nine. It's a popular place."

"Can I take my shower alone?"

His head turned to look at her, "Sure, if that's what you want. Any particular reason?"

"Yes. I don't want you to see me until I'm finished."

"Not a problem, but you don't have to. Any old thing would do and you'd still be ravishing."

"Let me do this my way."

He kissed her on the forehead and got up, gathered some fresh clothes, and went to the guest bathroom without another word.

*

She overdid it, emerging in an antique white, lace minidress that was brocaded with gold-colored seed pearls in all the right spots. It was off-the-shoulder and long sleeved and she looked hotter than nine shades of hell. Gold feather earrings and a gold "V" on a long chain completed her ensemble, along with white dress sandals. Anya had done her eye shadow in varying shades of gold and gone really heavy on the black eye liner and mascara. The V of the necklace lay on her chest just below the neckline and pointed at her hidden cleavage.

Randy whistled then asked, "What's the 'V' stand for?"

"Why virgin, of course," and she pranced past him with a merry smile and headed to the car.

As they left the house she told him, "By the way, that was evil."

Randy knew she was referring to their afternoon debauchery and the flogger.

"You didn't like it?"

"I didn't say that."

"That's what I thought," he replied smugly.

"The flogger, building me up and then leaving me hanging, the chairs you bought. You got a little sadistic streak going on there, you know that?"

"Ehh, maybe."

"Maybe my ass," she rebuked, then continued, "You enjoyed it."

"I enjoyed watching you cum from it. If I didn't think it would make you cum harder, I wouldn't have done it. Same with the other stuff you mentioned and everything else I do."

Anya laughed, "Cum harder, that's an understatement. I didn't even have to work for that one and it rocked me hard. Usually, I'm the one who is concerned with making a client cum. That's why I like you so much, you are only concerned with making me cum."

"What can I say, it turns me on, and I'll do just about whatever I need to in order for it to happen."

"And you do it well," she told him. Her hand found his on the console and Randy turned up his palm. She interlocked her fingers with his and squeezed lightly. From the corner of his eye, he spied a genuine smile on her taut face, the rouge prominent on her cheeks.

The restaurant he took her to looked like an old, single-story beach house made of cedar shake shingles with multiple dormers on the roof for natural lighting. It overlooked the sound and would provide a magnificent view of the sunset. They dined al fresco at a table for two that was just a little isolated by Randy's telephoned request while she was showering.

"Do you have a table reserved for you at every restaurant out here?" Anya had asked as soon as the hostess had left.

"No, just the ones worth going to," he replied and winked.

They had crab-stuffed shrimp with potatoes au gratin and cornbread, paired with a nice Chardonnay.

Randy had admired the way she looked all throughout the meal, her skin contrasting with the stark white of the dress as it peeked through the lace. He even found himself liking her makeup. By the time the dessert came he was ready to fuck the shit out of her, but Anya had other ideas.

She told him on the way home that she had a surprise for him and that he was to "cool your heels in the living room" until she was ready.

He played along, but told her he would be on the pool deck instead. He chain-smoked until she opened the French doors to his bedroom and whistled softly.

There were vanilla scented candles throughout his room, leaving it with a shadowy look as the candles flickered. Randy paused at the doorway to get used to the lighting and spied Anya waiting for him at the foot of his bed.

She had dressed in a short, black lace negligee, with black hose and a lingerie set that included a garter belt, lace thong and half-cup lace bra all done in what looked like a light rose color. She stood there with the long lace sash that was tied just above her navel, holding it out to its fullest extent from the bow with both hands.

Randy stepped just inside and watched as she turned to the full-length mirror on the wall between his dresser and the door to the playroom. Anya got to her knees, her feet tucked under her ass, and looked at herself in the mirror as she untied the negligee and pulled it apart.

He walked slowly to her, stopping on her right side, and she ran her arm between his legs and palmed his right butt cheek. With her left hand she unzipped his pants and half turned to him, fishing out his rapidly growing penis.

Her breathing grew shallow as she began to lick his cock, grasping his nut sack in her hand to steer it. He unbuttoned his shirt and took it off, tossing it behind him to the dresser, then bent over and slapped her ass.

"Ouuuu."

She breathed it out and then opened her mouth bigger to take him in, sucking on the head and first few inches as she removed the negligee. Once she had worked half of him in, she went to work on his balls, turning fully to him on her knees and putting each one in her mouth to run her tongue over it before switching to its twin.

Her hands went to work on his pants, pulling them the rest of the way to the floor, along with his underwear and as she refocused on his dick, Randy stepped out of his shoes and the rest of his clothing.

Anya was gucking now, holding on to the back of his thighs as her face moved forward and back on the tree limb that was filling her throat. She pulled on his legs hard, and her body rose, as she adjusted her head to get more of him down.

"Look at that," Randy commented, his hands embracing her face. He bent as she came up for air and kissed her, their tongues twirling.

As he held her face, he moved her body up and away from the mirror to lean over the end of the bed. He unsnapped her top and she removed it as he pulled down her thong and freed it from her legs. That left Anya in only the stockings and garter belt as he lifted her left leg onto the bed.

Randy got on a knee on the floor and spread her cheeks, running his tongue from stem to stern. Her left leg was bent on the edge, her right on the floor, as she looked back over her shoulder and tried to watch.

Finding that she was sufficiently wet, Randy stood and plunged his cock into her as she groaned. He bent over her back as he began to slow fuck her, turning her face further toward him with a hand and they kissed passionately.

The moaning continued as she broke off and looked down at his cock when he picked up the pace.

"Oh, like that," she grunted, "Yeah, mmmm, so good ... oh fuck yeah," she moaned, the fire raging and Anya put her face to the bed and bit the sheets.

The pace had gotten more forceful, and she pulled her right leg up on the bed, both knees pressed into the mattress with her feet dangling in mid-air.

All that did was allow Randy to drive her further and he stuck his legs at an angle out behind him and put his hands in the small of her back. Once she was pinned, he pounded her pussy for a good minute, Anya calling his name and imploring him to fuck her harder.

He reached out with one hand and pushed her face into the mattress, muting her voice while still allowing her air as he continued unabated.

Without removing his cock, he pushed her further onto the bed and then pulled out, turning her to her side with his body at ninety degrees and then re-entering to fuck her side-saddle while he held her thigh airborne.

Anya reached back and grabbed him, urging him onward as their movements pulled the sheets loose from the bottom corners of the bed.

She came then, pulling him tighter into her as her torso rolled back to him and he pinched her nearest nipple. When she had calmed, she moved to the floor to suck his cock as he sat on the edge, swallowing the precum and her juices that coated it.