Remote Work Pt. 02

Jerry rolled around on the couch and stretched. He wondered what time it was. The moment the thought crossed his mind, his heart started to pound as he feared he may have missed her call or text. She said she would be in contact this morning. In a panic, he grabbed his phone off the end table next to the end of the couch by his head, 8:04 am. No texts, missed calls, or emails from her, yet.

He sighed with relief as he stood up and walked over to the basement fridge to make some breakfast. He microwaved some sausage biscuits and made himself a cup of coffee before sitting down at his computer to start responding to emails. It was the weekend, but he never really stopped at his job, one of the reasons he was able to negotiate such a good salary and still work from home. It's also what kept his numbers so high, he rarely took time off.

After breakfast, he went upstairs to take a shower and clean up for the day. He may live alone and have little contact with people, but he hated filth. He'd seen real filth in some of the foster homes he lived in, he wasn't going to live like that. His house was clean and well organized. He was brushing his teeth when the text came. It was her, his cock twitched.

"I want your entire body clean shaven before I get there, everything except the hair on your head, and you had better be as smooth as a baby's ass, especially your face. You will be waiting for me on the front porch"

Shave my body? Weird, but all this is weird, he chuckled to himself. Shaving his body seemed like a small price to pay for Sandy's touch. Feeling excited about seeing her again and wanting to play along, he responded to her text with one of his own.

"Yes Goddess, it will be done as you command," he typed out with a smile. His cock swelled as he was having thoughts of Sandy alone with him, riding his cock as he lay on the bed. His cock continued to grow as he got in the shower, entertaining thoughts of Sandy. He was so excited he couldn't help but masterbate before lathering himself up and shaving his body. It felt strange. The shaving seemed to make his skin very sensitive and the water felt strange on his skin as it ran down his thin body, but he found himself liking the feel of it.

As he was drying himself off, his cellphone sounded a notification for another text. Nobody ever texts him, so he knew it would be her again. He quickly dried his hand and grabbed the phone. It was Sandy again, and he found himself so excited about it that a smile easily curled his lips.

"I will arrive around 6. Find a good local deli. Have them prepare a charcuterie board with meat, cheese, and fruit. Have your bedroom prepared for me, I will be staying the night."

His heart pounded as he read the text. She was staying the night. Holy shit. Was she going to fuck him tonight, he thought as a huge smile found itself on his face. He raced to get his clothes on and request an Uber as he searched for a local deli on his phone. He found what looked like a nice one, and called ahead to make arrangements so all he had to do was pick it up. After hitting the deli, he remembered smelling alcohol on Sandy when she entered his home. Wine, he thought, and had the Uber take him to an upscale liquor store. He realized he knew nothing about wine as he entered the store. Swallowing his fears, he approached the man working at the store. The man was huge, probably 6'-4", bald and in his late 50's. To his relief, the man was extremely friendly and nice. After speaking with the guy at the liquor store, who happened to have a good understanding of wine, he left the store with 8 bottles of assorted wines to try and cover as many bases as possible. The day was going great, he thought. Everybody he spoke to was nice to him, as if he was suddenly an accepted member of society. He felt better about himself and life in general than he had ever felt, he thought to himself.

When he got home the Uber driver even offered to help him get his shopping haul into the house, really nice dude. He tipped him heavily before sending him on his way. It was already 3:30 by the time he got home, 2-1/2 hours, he thought. Plenty of time to set up. He pulled out one of the folding tables he originally used for his workstation and computer desk while he was building his current set up. He looked around the basement wondering where to set up the food. The shower, toilet, and sink were in the corner to the right as you came down the stairs. To the left was the couch in a carpeted area that covered about 1/4 of the basement. Most of the rest of the floor was open except for the computer station/workbench that covered almost the entire 32' wall opposite the stairs.

He thought about it and decided that since the couch faced the wall and had nothing behind it, he'd put the table there to set the food up on. He stood the folding table up behind the couch and grabbed a white sheet which he threw over the table like a tablecloth, to make things more aesthetically pleasing. He was arranging the wine on the table when he realized he had no wine glasses. Shit, he thought to himself, and just went and got some regular glasses from the kitchen upstairs, along with a roll of paper towels and some paper plates. He returned to the basement and set everything up on the table, except for the charcuterie board, which he left in the refrigerator until she arrived.

With everything in place, he returned to his computer station and answered emails until she arrived, which he knew wouldn't be long, and he wasn't disappointed. She arrived just a couple minutes before 6. He was ready and opened the gate as soon as he saw her car pull in the drive from the camera on the pedestal by the gate. Then he dashed upstairs and onto the porch where he got on his knees in the position she had taught him and watched her pull up to his house. She hopped out of the car dressed like a teenager at a slumber party, light pink pajamas with red hearts that buttoned in the front with oversized heart buttons, pink bunny slippers, and her hair in a loose ponytail. She was still stunning, he thought, and alone. His cock swelled in his jeans.

"I thought I left you naked, Jerry." She grinned as she stood there and looked at him.

But they were outside, he thought to himself. She wanted him to be naked outside?

Her head cocked a little and her smile changed as one eyebrow arched. "Well," she said.

Yeah, that's what she wanted for sure. He started peeling his clothes off as fast as he could, leaving them in a pile next to him as his cock came to full mast. He dropped his pants on the pile leaving him naked.

"Better," she said. "Put your shoes back on and come over here you little skinny fucker. I have a job for you," she giggled as she headed to the back of the car. He put on his shoes and trotted quickly to the back of the car to join her, where she opened the trunk and gestured to two duffle bags.

"Bring those in, little man, and just look how happy you are to see me," she teased in her bubbly way while looking at his cock before turning and heading into the house.

He grabbed the two duffle bags, they were heavy, and he struggled with them unable to catch up to her. She disappeared into his bedroom, so he followed her. She was sitting on the corner of the foot of the queen bed, grinning.

"Put them on the bed," she told him as she patted the mattress next to her. He struggled over to the foot of the bed, set one bag down so he could place the other on the bed, and then picked it back up and placed it on the bed also.

"We're going to work on that weak ass body of yours, Jerry," she smiled as he struggled the bags onto the bed. One bag was black and one pink. She unzipped the pink bag and started digging around in it until she pulled out a plastic hair blush and then she hopped down on the floor and sat cross legged.

"Get on your hands and knees and face me," she smiled at him. She always looked so kind, and even though her words were bubbly, they always carried that underlying tone of authority somehow. He got on his hands and knees and crawled to her, she stopped him where it was comfortable for her to work on his hair.

"You're going to get a shampoo and conditioner that makes your hair less oily, that'll be an easy fix," she said as she brushed all his hair into a single bunch on the top of his head as he looked at the floor. She pulled it into three strands and started braiding it.

"We can't do anything about your height, or your face, but we can definitely put some muscle on your scrawny ass so I don't hate looking at you," she said as she braided his hair.

She smelled so good and his cock throbbed so hard it hurt. So many thoughts of what was going to happen were running through his head as she worked on his hair.

"There," she exclaimed as she wrapped the end of the braid with a hair tie. She stood up, leaving him on the floor on his hands and knees. All he could see now was her bunny slippers. He felt her grab the braid and she used it to pull him up onto his knees. He suddenly realized she had just turned his hair into a handle sticking off the top of his head.

"Get down stairs and wait for me," she bubbled as she released him, and stood there with her hands on her hips. He jumped up immediately and trotted quickly towards the basement.

"Yes, Goddess," he said as he complied. He ran down into the basement and grabbed the charcuterie board out the fridge, placed it on the table, and removed the plastic lid. There, everything was in place. He went to the center of the room, faced the stairs, and assumed the position he knew she wanted him in.

What was in the bags, he wondered. Restraints? Whips? That's what he was expecting. It made butterflies in his stomach. His heart pounded at the thought of being whipped. Could he do that? If she whipped him, could he endure it? Is the thought of fucking her, having his cock inside her, enough to carry him through such a painful experience. He'd had some pretty hard beatings from bullies, and felt like he could endure quite a bit for this beautiful woman. He suddenly realized he didn't hate her at all anymore. No, he adored her. He really wanted her touch again, even if that meant she would hurt him, that was the deal after all. He had agreed to exactly that, hadn't he.

Both his heart and his cock pounded at the thought of all this, his mind racing through scenarios, when he heard heels walk across the upper floor and start coming down the basement stairs. He watched as her shiny vinyl boots descended the stairs. They stopped ascending her legs about halfway up her thighs and laced up the back. Just above the tops of the boots he could see stockings, and the garters that held them, which then disappeared under a leather skirt only a couple inches above the boots. The skirt was attached to the bottom of a leather bustier that had lacing in the back and a zipper in the front. Her hair was pulled back in a tight ponytail, high on the back of her head. Her hands and arms were covered with leather gloves that went halfway up her bicep. She wore black lipstick and dark eyeshadow, giving her a very goth look. She deserved to be called Goddess, he thought as she crossed the room. She carried two handfuls of leather straps, chrome chains like a dog's leash, handcuffs, whips, and a paddle.

Whips and paddles, he knew it, she was going to whip him. His heart pounded and he wanted to run already. He was ready to quit right now, but steeled himself. She could see the look on his face, and grinned at his obvious discomfort.

"Relax, little fella," she chided him. "I'm not going to draw blood on you, this time," she laughed, her heels clicking on the concrete as she passed by. She walked over to the workbench behind him and placed all her handfuls of equipment on its surface. She pulled out a long riding crop and then walked over to the table he had arranged with food and wine.

"What is this, Jerry," she asked.

"It's what you asked for, Goddess," he replied.

"Well, I asked for a charcuterie board, yes. But this arrangement makes me wonder what you think of me, Jerry," her tone pouty. Then her tone lost the poutiness, and became almost irritated, "Paper plates? That's why you think of me, Jerry? I don't even deserve an actual fucking plate," she asked.

"I'm sor," he started to say when she cut him off.

"Shut up, you little shit. It was a rhetorical question," she laughed. "Paper towels instead of napkins. Wine and no corkscrew. Tumblers instead of wine glasses." She reached down and picked up a piece of cheese and ate it.

"I have a corkscrew, Goddess. It's upstairs in the kitchen." He said to her, hoping to appease her at least some.

"Well, go get it then, little man," she giggled, and he sprang up and sprinted up the stairs to where he knew the corkscrew lay in a drawer. He grabbed it and sprinted back down the stairs. He ran over to her, got on his knees and presented the bottle opener to her in both hands, expecting that's what she wanted.

"What the fuck am I gonna do with that," she laughed. "Open that red on the far left and pour me a glass," she was bubbly again and that calmed him.

He jumped up and did as she had commanded while she stood and watched him, tapping her riding crop lightly on her boot, but hard enough to make noise. He pulled the cork of the red, and started pouring a glass.

"Stop," she commanded about halfway through filling the glass and he stopped. "Never fill a wine glass, Jerry. Put the bottle down and return to the middle of the room," she bubbled with a beautiful smile. He complied and she picked up the glass of wine, smelled it, and took a sip.

"Present," she giggled as he reached the spot where she wanted him. He spun to face her and assumed the position. She took a few more sips of wine and smiled at the ridiculous looking pigtail sticking off the top of his head. She sat the glass down on the table and walked over to him. She stopped a couple feet in front of him.

"You know I'm going to punish you for fucking up that table, don't you, Jerry," she smiled down at him.

"I thought you might, Goddess," he almost whispered. He trembled slightly, but his cock was still standing proudly from his crotch. It looked impressive on his small frame, even more so clean shaven. Sandy smiled down at it as she stepped very close to him. She grabbed the pigtail on top of his head to balance herself as she raised her right foot slightly and pressed the front of her boot against his hard cock. He pressed back and she moved her leg up and down just enough to make him hump her a little.

"Do you like humping my leg," she giggled and took her leg away. A string of smegma ran from his cock to her boot.

"Yes Goddess," he gushed, still humping air like a dog as she pulled her leg away, she laughed out loud.

"I see that," she laughed and released his pigtail. "Clean that off my boot," she giggled and tapped her boot with the riding crop next to the smear of smegma.

He started to reach for the smear with his hands and she smacked them away with the crop.

"No, no. Lick it off my boot," she giggled down to him. He just sat there looking at it on her boot for a moment. Did he really want this? Licking his own smegma off her boots hadn't even crossed his mind, but here he was, and he knew if he said no, she'd likely leave, pissed. He swallowed hard, leaned in and licked it off her boot. The vinyl was slick and so smooth as his tongue glided over the soiled area. He turned his head and gagged.

"Choke it down, little man. Eat it," she giggled. He turned back to her and resumed cleaning the thick salty fluid from her boot with his tongue, without gagging this time. When she was satisfied with his work, she dropped the crop on the floor next to her, reached down and grasped his pigtail in her left hand, using it to bring him back up on his knees. She then reached down and wiped a couple large drops of smegma off the end of his cock onto her index and middle fingers, stood up and shoved her gooey fingers into his mouth as she looked down at him and bit her lip with a little smile. He started to gag again and tried to pull back from her and turn his head away. She yanked her fingers out of his mouth and slapped him, hard enough to ring his ears.

"Get used to eating everything I feed you, Jerry, and that includes everything that comes out of your dick," she said sweetly before releasing his pigtail.

"You want me to touch your dick again don't you, Jerry," she giggled.

"Yes, Goddess. Please touch me again," he begged.

"That can't happen until you beg me to punish you for that table over there, and anything else you may have done to displease me, do you understand, Jerry," she asked.

Is that what it would take? He would have to beg her to whip him, and after doing that, and being whipped, she would touch him? Is that what she wanted? So be it, he thought to himself. He leaned over on his hands and knees, kissed the tops of her shoes and he begged for her whip.

She giggled as he groveled shamelessly before her for the promise of her touch. She relished such power. Jerry had barely even thought about it before begging, making her wonder how far she might be able to push him. What pains would he endure, what humiliations would he subject himself to, just so she might touch him. She had her hooks deep in him and she could see it. He had only met her yesterday and within just a few minutes of seeing her in all her dominating glory, he was licking her boots clean of his own filth. This ugly little fucker was going to do it all for her. She would inflict the most humiliating things on him, disgusting things, and he would beg for it, he would beg for the whip afterwards. He would beg, and beg, and beg, and she would dish it out as harshly as possible, giving him pleasure and comfort only when he absolutely needed it to string him along, for no other reason than to satiate her desire to grind him into the dirt, and she was a master of this game.

"Good boy, Jerry. That's enough slobbering on my boots, but stay down there with your face all the way on the floor and you ass in the air," she said as she pushed his head down with the bottom of her boot until his forehead was on the floor. Then she stepped around to his left and turned to face him. That's when he heard the crop cut through the air for the first time before meeting the flesh of his ass with a loud crack. He flinched and inhaled sharply. It didn't hurt as bad as he had expected. It stung, but it wasn't gonna make him give up. She watched him carefully, then delivered another stroke, and then several more in rapid succession. He only flinched and writhed at the strokes, but didn't try to crawl away.

"Good boy, Jerry," she cheerily said. "I expected you to try to get away from my crop," she bubbled at him.

"Now beg me to punish you, Jerry," she said with absolute authority. His heart pounded suddenly at the change in tone. It scared him.

"Please punish me until you feel I've learned my lesson, Goddess," he begged in a shaky voice belying his fear. She smiled sweetly, before biting her bottom lip and raising the crop high. She wasn't testing him this time, she was punishing him, and the crop ripped loudly through the air before meeting his flesh. It cracked against him leaving a stripe of fire on his skin. He jerked his head off the floor and scooted forward a few inches as he gasped in air.

"Head down," she said cheerily. "We don't stop until you've had ten strokes of the crop without trying to scoot away or raise your head off the floor, and maybe, we will be done. Now back up and put your face on the floor," she said sweetly like she was trying to help him while she stood there with a whip in her hand. He got back into his original position.

"Now beg for me to start again," she giggled teasingly.