A Randy Retirement Pt. 29: Anya

He let her go at it for a bit and then took her hair and moved her further away from the bed, placing her face on the floor with her ass up. Then he squatted and entered her ass.

Randy could see Anya's face turned to the right, both of her lips curling into a snarl as she gnashed her teeth and growled.

When she was ready to cum he denied her, pulling out and flipping her over. He fingerbanged her instead, heating her up until his hand was covered in her juices, but still he denied Anya more satisfaction.

Her eyes were wild, and she howled when he removed his fingers and got to a knee beside her, putting the hand that had just come from her cunt into her mouth and making her suck it clean as he had done before.

She did, running her tongue across his digits as Randy pushed his fingers deeper, pushing down on her tongue and making her gag. He eased up, then immediately made her retch again, her chest heaving before he pulled his hand free and helped her up.

Taking her to the club chair again, her pushed her down into it, her knees on the seat and her ass facing toward him. She had her arms folded along the back, elbows out, as Randy put his knees in the chair seat and entered her ass again.

He pounded her so hard that she grunted out an "Ughhh!" with each stroke, the air nearly leaving her body as his weight forced her diaphragm into the back of the chair.

Randy's hand entwined in her hair and as she felt it, she gave a little glimpse of her yearning.

"Ouuuu."

He pulled harder, making her back arch and the glimpse turned sultry, her head turned now toward the ceiling.

"Ahhhh ... YES!!"

Slowly he released her curls, but she kept her head in place, a wet plopping sound as background while her lean ass rippled with every stroke. Anya's head began to bob in time with each plop until it looked as if she were riding a bull that was determined to shed her from its back.

In time, her voice turned down in pitch and Randy knew it wouldn't be long. He reached around to where her chest was now hanging over the back and pinched both her nipples hard, pulling them toward the floor, her small breasts deforming as she continued to grunt.

The first sense of his seed making the journey from his balls to his cock came over Randy and he power stroked deep inside Anya as hard as he could, urging it onward just as she began to shudder. Twin eruptions came in synchronicity as he moved his hands to her hips, holding them tight as he emptied himself.

There was sweat and bodily fluids all over the bedroom as they stayed put and panted. This was one of the reasons that Randy owned a carpet steam cleaner.

He had sat down in the chair, Anya turning to sit in his lap. She looked at him and said between labored breaths, "Damn."

It took over an hour to clean up.

***

Monday

Anya's spot was empty when Randy awoke. He got up in his boxers only and checked the bathroom. She wasn't there. Continuing into the rest of the house, he had the same luck. He finally found her sitting on the rock wall of the gazebo by the firepit, leaning back against one of the support posts. She was dressed in his long white bath robe, and it covered her entire body except for her head and feet.

The wind from the appoaching storm had abated for a bit, everything about the gazebo calm and serene.

"Quiet time?" he asked.

Without looking at him she replied, "Something like that."

"Would you like breakfast?"

"No, thank you," she replied, still staring out to sea.

Randy waited to see if there was more, but Anya was quiet and he thought to himself, 'Well hell, if she's in a contemplative mood, I'll ask her a contemplative question.'

"You've told me how you got into the business that you're in when you were here before. Tell me why you've stayed in it."

She looked down at her hands and considered his question for a moment, then looked back to the ocean and said calmly, but quietly, "When I was in school and getting kicked out and such," then she stopped and asked, "Can I have one of your cigarettes?"

"Sure thing, just a minute." Randy went inside to fetch the pack and lighter. When he came back, he lit one for her and handed it over, then lit his own and sat down in the nearest chair as she continued.

"I've never told this to anyone," she started and then stopped again.

Randy remained very still and quiet as she took a deep drag and held it before blowing out the noxious fumes from her lungs. It was almost two minutes before Anya continued and her eyes were now wet.

"I constantly found myself fantasizing about men tying me up and having their way with me. Over time, I found myself wanting to be their outlet ... for their stress ... for their sexual frustration ... their fantasy, whatever it might be. I found that I liked to serve the desires of men. Soooo ... I kept doing the escort thing because I craved ... no, that's not right, I still crave to be transformed into a helpless little whore by dominant men. And they paid me for the privilege."

She stopped then. Randy didn't speak, instead he waited to see what came next. She finished her smoke and got up to put it out in the ash tray on the table, then turned to him and smiled.

"Somewhere along the line I discovered that I could get just about anything I wanted if I played my cards right and my chosen profession became even more intoxicating. Then there was the excitement of it all."

Randy nodded, but remained passive.

"And then there was you. When you told me you don't pay for sex, I thought it was just some macho bullshit, But it's not. You're different. You don't have all the associated hang-ups and entanglements; you just enjoy the fucking. There's no outside stress, no frustration you bring into the act." She smiled broader, "Hell, you probably have no fantasies. For you, it's all about the cumming; make the woman orgasm and you get off on it."

He didn't say a word and she winked at him and untied the sash of the bathrobe while she resumed talking.

"And the thing of it is, I get the feeling that as far as you're concerned, the women can take it or leave it. As you said, there's lots of them out there just dying to give it away for free."

She started to gyrate her hips then, a little dance ensuing that turned into a strip tease with the robe. When she took it completely off, Anya dropped it into his lap and continued to dance, tugging hard on her nipples.

As he watched her, Randy removed the sash from the robe and then put the garment on the table. He stood and wound the sash around her throat twice, and just like with his belt earlier that he used as a leash, he led her to the playroom once again.

He placed her in the middle of the room and got the heavy-duty suspension cuffs, wrapping them around her wrists. Letting the cable down from the overhead winch, he clipped both cuffs to the cable and wound it up until her arms were extended straight above her head.

He left her there and went to get a few more items, ballgagging her upon his return. Grabbing the winch control hanging nearby, Randy suspended Anya further, stopping when her toes were a foot off the floor. She dangled there, stretched to the limit with the big red ball muffling her moans.

He pulled a pair of tweezer clamps from the waistband at the back of his boxers and pinched her nipples hard, then put the clamps on and made her squeal when he ran the metal ring as far up as it would go.

Removing his boxers and spinning her around, he slapped her ass every time it passed and then stopped her by grabbing her hips.

Anya was short enough that her pelvis was at just the right height to fuck, and Randy lifted the chain connecting the clamps, her body moving slightly toward him.

Her head trapped between her upturned arms, she grimaced at him, drool slowly forming on her lower lip.

"You want my dick?"

Anya nodded.

"Tell me you want my dick."

She tried, the words malformed and bearing no resemblance to any known language except the language of desire.

"Nod again if you want my cock Anya," and he lifted a little harder on the chain, watching as the steel that trapped her nipples turned them up and in.

Her head nodded furiously, and he let go, causing her body to swing slowly backwards.

Randy entered her then, picking up her body with his arms and letting her slide down with his cock in her pussy. He held her by her thighs and plowed into her, staring into her eyes until she came, the drool now a continuous stream.

She pulled up with her arms then, arching her back and pushing her hips forward.

"You want it in your ass?" he asked, and she nodded furiously again.

He helped her and stepped back to get a better angle, pushing his still hard monster fully into her rectum. Within five minutes she was cumming again, her body going limp as the climax permeated her existence.

Randy kept going until he climaxed as well, thrusting hard into her with each gush of cum. He shuddered when he finished and let her legs drop. When he removed the clamps she revived and howled, a noise that continued when he let the ballgag drop from her mouth.

Letting her down, Randy carried her to the shower and held her under the hot water until she could stand on her own.

*

They took lunch at Mike's Grill Room eating alfresco in wooden lath-backed chairs. The tables all had white linen tablecloths and Anya luxuriated in the sun while she waited on her shrimp and grits.

She had her cheek in her hand, elbow on the table, and beamed at Randy; ignoring the lingering stares she was getting, for she had chosen a tank top that bordered on the wicked. The bottom of the arm holes went all the way down to the top of her hip and the least little gust of wind would reveal a full side shot of her unencumbered breasts. It was a saffron shade of orange and she had on a pair of white canvas pants that complimented the top nicely.

She knew exactly what she was doing, to him and the populace, and she didn't care.

Their meal arrived, the shrimp dish for her, and a hamburger for Randy. It was a simple meal, with casual conversation and she asked if they could walk on the beach when they got back.

"Sure, but I have a question for you."

"Okay," and she batted her eyes at him in anticipation.

"That top. Where did you get it?"

Anya looked down at her chest and then back at Randy.

"This? It's a men's cut-out gym shirt. Why?"

"Cut-out is the term for the overly large arm holes?"

Anya nodded yes and Randy told her why he asked.

"I was thinking about getting some. You look so delicious in it I wanna see if any of the others would be bold enough to wear one in public."

She laughed silently and drank some water, putting the glass back on the table and telling him, "You're bad. I tell you what, go back by one of those beach shops we were near the other day, and I'll help you pick some out."

"Do you think they'll have them?"

"If they don't we'll get online after our walk and I'll help you find some."

*

They got to one of the stores and Anya went straight to where the shirts were located, finding them with no problem. Randy was eyeing the packages without picking one up and she looked to him and asked, "You trying to determine size?"

"Yes."

"I'm wearing an extra small, so if they don't have big boobs get that size. If they are more well-endowed then you probably need to get a men's small."

He was thinking of Halley, Gabbie, Ellie, and Katie and, figuring in his head, said absently, "So I probably need two packs of each. Now what colors?"

The shirts came as singles or in packages of three and there were a multitude of colors, three different colors in each package. Anya took charge, finding a small and extra small package of fluorescent colors, yellow, orange, and blue. She then hunted for the same sizes in neutral colors, black, white and gray, finding them in under five minutes.

They went through the checkout line together, a young lady in her late teens running the register. She couldn't take her eyes off Anya at first and when she started to ring up the shirts she looked closely at each purchase and then at Anya's top, then back at the purchase.

Her nametag read "Jenny" and she was probably fresh out of high school. With each of the four packages of shirts her eyes flitted back and forth between each set of plastic wrapped shirts and the painted woman standing in front of her until she was finished ringing them up and announced, "Your total is $81.57."

For the first time she looked at Randy and a broad smile broke over her face as she quickly discerned the age gap and made the connection in her mind. Randy paid her and awaited his change, the young lady telling them both as she placed it in his hand, "Y'all have an enjoyable evening."

Randy picked up the bags and moved to leave, but Anya lingered, telling the girl, "Oh honey, I plan to," and she licked her lips and gave the girl her best seductive look.

To the amusement of both Randy and Anya, the girl winked, made a kissy face, and smiled at them; then visibly sighed and said hello to her next customer.

Headed to the car, Anya said to Randy, "You're coming back another day to see if she's working, so you can seduce her, aren't you?"

"Maybe," was his answer, his mind busy storing what he knew about Jenny in his memory bank.

Anya laughed as they got to the car and got inside. She was still laughing as she buckled her seat belt. Randy started the car and paused to look at her.

"What's so funny?" he asked smiling.

"You! Maybe," and she tried to mimic him as she repeated his answer. "Yeah right. Get me home and do me, Mister Maybe."

Randy laughed softly and wheeled out of the parking lot, coming back at Anya, "Hey, I can turn around and find out what time she gets off and we can have a threesome."

"Oh no," she immediately replied. "I only have so much time left here and I'm not sharing you."

"Because I'm so lovable," Randy teased.

"Because you're so good at making me lose myself," Anya corrected. "Don't go back right after I leave, give her a couple of days, but no more than ten."

"Why's that?"

"You give her a couple of days and she'll spend them stewing in her thoughts of you. That girl will be ready for just about anything you want to do to her, but you got to get the timing right, after ten days the image she has in her head will start to fade."

"And you know this how?"

"The look on her face. I've seen it before."

"Where?"

"When I was younger, every time I looked in the mirror."

*

He left the garage door up when they got back to the house, leaving the shirts in the car as they exited. Randy hit the button to close the door before they went around the outside and down to the beach.

As they headed south, Anya reached and took his hand again, interlocking her fingers with his. The wind was back, driven by the oncoming storm, and it hit them in the face, Anya's hair blowing wildly.

Within five minutes she noticed that houses had begun to appear on their right.

"You have neighbors?"

"I do, somewhat. The closest house on the beach is a quarter mile from mine. I own all the beachfront land between it and mine."

"What about the house that's across the road from you?"

"Yeah, that got put up before I could get the property, but I rarely see anyone there," and he shrugged.

They walked on for another twenty minutes before he asked, "You about ready to head back?"

Anya gave him a sneaky smile, "You have something planned for me?"

They stopped and turned, changing hands, and he told her, "I have something I want to do to you."

Randy felt her shiver. The wind was whipping her hair past her face and she struggled to keep it tamed. It also billowed her top, giving full views of her pointy, hardened nipples.

"Oh, now why do I like the sound of that," she replied and began to swing their hands between them.

Randy took her straight to the living room. The leather couch and television dominated the center of the round room, but off to the sides were various tables and chairs.

Going to the south side of the room, he stopped her at a strange piece that she had never noticed before. There were two rugs hanging on it and when Randy removed them what remained were two rails, each three feet high, four inches wide, and four feet long. They were heavily padded on top and stood parallel to each other.

"You undress and I'll be right back," he told her, and she began to take off her clothes, watching him as he went to the couch. She saw him pull a storage tray from underneath it and gather several leather straps and cuffs. When he got back, he handed her a pair of wrist cuffs.

"Put these on," and while she did, he undressed and took both their clothes to the coffee table.

Coming back to her, Randy reached down and pulled a ballgag from the bundle of straps, stepping behind her and waiting until she bowed her head and opened her mouth in acceptance. He seated it behind her front teeth and buckled the straps tight, including one that ran under her chin.

Picking up a ringed collar, he put it around her neck, buckling it in place as well as her eyes followed him.

Stepping between the rails and the windows, Randy punched a button and down came a cable from the ceiling. Anya craned her head up and saw for the first time a winch, hidden in the ceiling of the living room.

'Will wonders never cease,' ran through her brain as she slowly shook her head.

When the clip on the end of the cable was two feet above the railings, he stopped it and then patted the nearest one, "Okay, up you go."

Anya looked at him, her eyes showing disbelief.

"Here, I'll help you," and he took her arm and helped as she got on all fours on the rails. She supported herself on her knees, her toes and her hands and began to wonder what the fuck he was up to.

She could clearly see the ocean and the beach in front of her through the windows and she realized that in the same respect, anyone who approached the house could see her if they got close enough.

For his part, Randy began to use the straps to bind her lower legs to the railings, placing one set just below her knees and the other at mid-calf. He cuffed her ankles and attached the cuffs to an eyebolt the was secreted under each rail.

It was at this point that Anya realized the rails were far enough apart that Randy could stand between them, and his intent became clearer. She expected him to come around and clip her wrists in front of her to the railing, but Randy had other ideas.

Stepping in behind her, he reached across her back and grabbed both arms, pulling them behind her and clipping them together. If he had not held onto her, she would have fell through the void with nothing supporting her torso.

To alleviate this, Randy raised her wrists, putting the strain in her shoulders as he clipped the cuffs to the cable that was about six inches above her back.

"Mmmhph," she moaned through the red ball in her mouth.

Randy patted her on her bare ass and walked out from between the rails and back to the switch hidden in the wall of windows. He punched a button and Anya's hands began to rise, her arms following.

"Mmrhphff!" she squealed, her torso rotating down and her ass up as her hands rose.

Stopping the winch, she was left with her head lower than her ass, and even with the height of the railings.

Suddenly he was in front of her, attaching thin chains to eyebolts in the front of the rails and then clipping them to the rings in her collar. The chains were taut and would keep her torso from moving to either side.

His hand cupped her chin and he told her, "I thought about putting a hook in your ass, so your head had to stay up, but I want to fuck it so..." Then he patted her cheek softly, "I guess one can't have everything."