Terri's eyes tracked his as he stood. Derrick glanced at the dark, empty parking lot. Someone could walk by the windows, but no one had for the last hour. He pushed down his pants and boxers, exposing his hard cock to the young woman. Standing with his hands on his bare hips, he nodded. Terri's gaze slipped down his body until her eyes landed on his swollen manhood. The nodding throb his prick gave her gaze was involuntary. Her serious expression never changed, though he saw the pupils of her eyes widen. He smirked.
"Now jerk-off," she told him.
"Here? Now?"
Her eyes flashed back to his, narrow and intense. "Did I stutter?"
After giving the parking lot another glance, he gave his hard cock a few tentative strokes. Yes, he was hard, but was he excited enough to produce an orgasm quickly? He kept stroking. She looked, watching his hand move with the same impartial look on her face, as if she was watching him read or fill out a piece of paperwork. Still, she was watching him. He felt a thrill surge through him, spurring him to keep going. Glancing again at the empty parking lot, he looked past it at the cars driving past the center. This was crazy. Someone could see. Not from the road, but if they pulled into the center, they would. Inside the brightly lit store, he would be on display for any mother out running errands while the kids were in school or retiree too bored to stare at their TV. What about his neighbors? The strip center was big, but another manager might stop by for a drink or to shoot the shit. He worked his cock faster. The sooner he came, the sooner he could get dressed. He felt his thrill grow. He was close, arriving there faster than he expected. A week's worth of unintentional celibacy worked in his favor. "So close," he muttered.
"Cum on the table," Terri said, watching his expression as much as his hands working on his hard cock. There was a hint of a smile at the right corner of her mouth and a twinkle in her blue eyes as he reached his peak. His cock erupted, spraying his orgasm in a loose line from one end of the table to the other. Terri's laughter wasn't the reaction he expected. "Good one," she said. "Now lick it up."
After a last shiver of pleasure worked through him from his shoulders on down, Derrick looked at her with wide eyes and raised eyebrows. He looked at his semen laid out in wiggly spray of lines punctuated with drops and a small puddles against the faux marble topped table. He knew the table was clean, he was meticulous about keeping his store clean. Her wide smile told him everything he needed to know. She didn't think he would do it. Pants and underwear still around his knees, holding his hard cock, he bent and lapped up the mess he had produced. He worked from one edge of the table to the other, tasting the Formica top as much as his spent seed. Glancing up, he kept an eye on the parking lot and front door. No one saw him.
Finished, he hesitated before pulling up his pants. "May I get dressed?"
"You learn fast," she said. She grabbed his balls, watching her hand caressing them for a moment before she looked up at him. "If we do this, I own these. Are you sure that's what you want?"
"Yes ma'am."
She stroked his still hard cock. "Stand against that wall and wait for me," she said, looking as if she had reached a decision. Pants still around his knees, exposed to anyone who might drive or walk past his store, Derrick moved where she directed. From behind the counter, Terri grabbed her cell phone from her purse. Cell phones weren't allowed during working hours. Turning it on, she pointed its camera at him and snapped a picture before moving to stand in front of him. "Get dressed," she said, sitting back down at the table. Derrick pulled his clothes back into place and joined her.
Terri's phone displayed the picture of him standing next to the logo painted on the wall. Beneath the picture were two buttons, save and delete. She positioned the phone in front of him. "Your choice. One button leads to your destruction. The other?" She shrugged. "I guess the other means I just got a free show."
"My destruction?"
Terri covered the phone with her hand. "I'm serious, Mr. Mac. My role becomes finding your limits and pushing you past them. The more you squirm, the more fun it becomes for me. Discipline is only part of the deal. If you fail me, I'll send that picture to corporate headquarters."
"It's a sex game, though, right?"
"For one of us, it will be."
When she moved her hand, he pressed the save button.
"Umbrella is your safe word," she said, picking up her phone and putting it her pocket. She explained what a safe word meant, how he was to call her only Mistress when they were alone, and difference between living in the world and being "of" the world. "You live in this world, but are no longer of it. You have no rights. No one is to know of our arrangement. Lie to anyone but me." As her list of instructions and rules went on, Derrick's second thoughts began. She had clearly thought about this in much greater detail than he had imagined. When she was done, she produced her phone again with the picture of him standing in front of the logo. Once more, there were two choices, upload or cancel. "If you press upload, it's saved to a private folder on the internet. If you press cancel, we'll delete the picture from my phone and forget all about it." He hesitated before pressed upload. "You're a stupid, fucking bitch," she said, laughing and heading behind the counter again. He guessed she was putting away her cell phone. Instead, she brought her purse back to the table and sat. "Can you get hard again?"
"Yes," he said, the anticipation of her next command teasing him.
"Good. Throw away your underwear, you won't need those anymore and let me see how hard you can get."
Recognizing his lack of choice in the matter, Derrick slipped off his shoes, pulled off his khakis and underwear, and threw away his boxers. Sitting bottomless next to her, he rubbed his cock back to life. It didn't take long.
"Good. Put your pants on in case someone comes in."
Relieved that he was allowed to dress, he scrambled back into his pants. "Thank you, Mistress," he muttered, using her new title for the first time. Beneath the pleated front, his hard on was still obvious.
"Do you have a camera on your phone?"
"Yes Mistress."
"Good. Then you can text me a picture of your hard cock every five minutes. Exactly every five minutes. And not a picture of it through your pants, but of your bare prick, understand?" Holding her purse, she pulled out her car keys and stood.
Derrick nodded. "Where are you going?"
"You don't get to ask me that anymore, bitch."
"Sorry, Mistress," he said, wondering how he could still be her boss at work. Did that still apply? Digging through the menu on his phone, he found a timer and set it for five minutes. Lost in thought, he had to revive his hard-on for his first picture. Bored, he walked around the store, pacing until another five minutes had passed. This time, his hard-on was waiting for its picture. He unzipped, pulled out his penis, snapped the picture, and was busy sending it when headlights moved through the parking lot. He realized he was standing in plain sight of the car with his hard cock sticking out from his pants. He turned his back to the window, finished sending the text, and tucked his prick back into place. During the next several alerts of his timer, he remained cautious.
Nine times, he sent Terri pictures of his hard cock. After the second one, he sent the rest from the relative privacy of his backroom office, sure that he was safe from prying eyes. He was getting ready to snap off his tenth picture of the afternoon when the service door opened. Spinning away from the open door, he fumbled with his phone and exposed prick, dropping his phone on the floor before he heard Terri's laugh. "Just turn around," she said. He did, his hard cock sticking out of his fly. He saw the delighted smile on her face and felt good to be a part of it.
Walking around him, Terri ran her hands over his body. She grabbed his pecs, squeezed his ass, and for whatever reason she had, tweaked one of his ears. Standing back in front of him, she caressed his hard cock. It felt strange to have this young employee of his touching him so intimately. Six inches shorter than him, she stared up at him as she rubbed his prick. "You were a good boy,
" she told him. "Every five minutes, right on the dot, you sent me a pic. That deserves a reward. Did you know I love to suck cock, Mr. Mac?"
"No Mistress," he said, his cock throbbing inside of her hand.
"Mm, I do. I love the feel of a nice, long, hard cock between my lips. You know the best part of sucking cock, Mr. Mac? Feeling him exploding inside your mouth. Fuck, I love that feel. I get wet just thinking about it. Would that be a good reward, Mr. Mac? Would you like to feel my warm, wet lips around your hard cock?"
"Yes Mistress," he said, though he was sure his throbbing cock was answer enough for her.
"Or maybe you'd rather see me naked. Would you like that, Mr. Mac? Would you like to see how I look naked? I know I don't have big tits, but they're perky and my nipples are really long. Everyone loves my nipples. Do you liked shaved pussy? That's how I keep mine, nice and smooth. Do you want to see me naked, Mr. Mac?"
He felt his mouth go dry. Was she setting him up? Was there one answer that was better than another? "Yes Mistress," he repeated, thrilling at the idea.
"Hm, which should I do, Mr. Mac? Should I suck you off or should I let you see me naked?"
His need had grown to great. Forced to choose, he chose the answer that included a release for him. She looked up at him with raised eyebrows, waiting for an answer to her question. "A blow job would be good, Mistress."
"Wrong answer," she said, still rubbing him. "Would you care to try a second time?"
"Seeing you naked would be a privilege, Mistress," he quickly amended.
"That's true, it should be a privilege for you to see me naked, but it's still the wrong answer."
Derrick felt lost and confused. How could both answers be wrong?
Ignoring the confused look on his face, she pressed forward. "Strip," she told him, backing away and watching as he took off his clothes. He pulled off everything from his logo shirt to his shoes and socks. "Good, now bend over and grab your ankles." He did as he was told, unsure what to expect until it happened. Using one of the long handled spatulas they used for cleaning the yogurt machines, Terri swatted his ass. The restaurant quality tool made a loud smacking sound as it bounced off his left buttock. A moment later, he felt the sting from her attack. She followed with a second smack on his right cheek. Once more, he experienced a momentary delay before his body registered the pain of the assault. Again and again, she spanked him, alternating cheeks and precise locations until his ass felt hot and on fire. He winced with each subsequent swat. Finally, she stopped.
"Keep your eyes forward," she commanded. He kept himself frozen in place, unable to see or guess what she was doing until he felt it. She was pressing something against his asshole. He didn't know what it was. He guessed it wasn't a finger and she had somehow lubed it. It felt uncomfortable, but it was slender and she was gentle about working it inside his asshole. "Hold it there or I'll beat you with it again," she said, solving the mystery. She had pushed the handle of the spatula up his ass. When she let go, he felt it threatening to slip from his ass and clenched down on it, willing it to stay in place. She moved in front of him, grabbing his chin and turning his face up to hers. She solved a second mystery for him. "The right answer was 'Whatever you wish, Mistress.'" She pulled the makeshift toy from his ass and he heard her toss it in the sink. "You can stay naked. Maybe I'll decide to reward you later."
"Thank you, Mistress," he said, feeling vulnerable and exposed. The bell on the door chimed and Terri pushed her way up front, leaving him. He listened to her talking to the customer with her usual cheerfulness. Hoping it was okay, he stood up. His ass hurt, but his cock was still hard. He spent the rest of the day hiding in the backroom.
At the end of the day, she sent him home in need of an orgasm and with a list of supplies in his pocket. "I'll call you tomorrow and we'll begin your training," she said, leaving him naked in the backroom of the store.
It was eleven thirty when his phone chirped with a message from Terri asking for his address. At noon, she showed up on his front step. Derrick had filled her list, shaved his cock and balls, and was hard with anticipation when he opened the door for him. Standing in the small foyer, she inspected him, running her hand over his shaved flesh. His cock danced from the attention. "Are you in need?" she asked.
"Yes Mistress." He was. He had spent the night and his morning excited and hard.
"Do you want an orgasm?"
"Your will, Mistress," he said, careful not to repeat yesterday's mistake. He saw her smirk, catching his careful reply.
"You learn fast," she said, grabbing him by his cock and leading the way into his small home. It was her first visit and she gave herself a tour of the two bedroom, two bath bungalow. She pulled him behind her as she moved from room to room. Living alone since his divorce, Derrick kept his space meticulously clean. She paused in front of his dresser. "Open your underwear drawer." When he pulled open the top drawer, she shook her head. "What's this?" she asked, holding up a pair of his boxer shorts.
"Underwear?" he replied, confused.
"Didn't I say you won't need these anymore?"
"Yes Mistress," he said, squirming. She had been in home for less than ten minutes and he had already disappointed her.
"What kind of guy folds his underwear?" she asked, pulling out each pair of boxers and throwing them around the room. Leaving him standing in his bedroom, she returned from the main room with the package of spring clothes pins from her shopping list. Opening the package of plastic clips, she began clamping one after another of the rainbow colored clips on his balls. The pain was exquisite. As she added each clip, his cock bobbed and throbbed. "There," she said, leaning back to admire her handiwork. "Ten pairs of underwear. Ten clothespins. Now pick them up with your teeth and throw them away."
Dropping on all fours, Derrick crawled around his bedroom. One by one, he picked up a pair of boxers with his mouth, carried it to the wastebasket in the corner, and dropped it inside. The clothespins on his balls felt like bee stings, but his prick stayed hard. He was on the last pair when one of the clothespins worked its way off his balls. Any hope he had that she wouldn't notice or wouldn't care vanished quickly.
"Worthless bastard," she said, picking up the plastic clamp. "Stand up." He did. She replaced the clothespin and added one to each of his nipples. "Wait here," she instructed, returning again to the other room. Turning him around, she used a length of rope to tie his hands behind his back. Next, she wrapped a scarf around his eyes, blinding him. Hands on his shoulders, she turned him around and backed him against the wall.
He stood, listening intently. He sensed her still in front of him. If he looked down the bridge of his nose, he could see his hard cock, the clothespins on his body, and his feet. Feeling something soft against his toes, he looked down to see a pair of panties resting on his toes. A moment later, they were joined with a bra. His cock throbbed as he realized Terri had gotten undressed, too. He fought the urge to raise his chin so he could see his bed. Listening, he heard her soft moans of pleasure and the faint moist smacking noise of fingers rubbing a pussy. He heard her gasp as an orgasm overtook her. When she shoved two fingers inside of his mouth, he tasted her sex for the first time.
"When you're ready to try to serve me correctly, I'll be in the living room. Take off that shit and join me." Looking down the bridge of his nose, he saw her pull away her panties and bra before he heard her leaving the room.
When he wiggled his hands, he found it easy to undo the job she had done lashing his wrists together. He found it interesting that she hadn't bound him any tighter. Hands free, he pulled off his blindfold. The opened package of clothespins were still on his bed. He pulled off the twelve clothespins he wore, put them back inside the bag, and walked into the other room.
He found Terri standing naked at the dining room table where he had positioned the supplies from her list. Her firm, tiny ass was as tanned as her back. She turned when she heard him. "Looks good," she said, smiling.
"Thank you Mistress," he
said, his prick throbbing as he drank in the sight of her so casually naked.
"Balls hurt?"
"Some," he admitted.
"Relax," she said, opening a couple packages. "This is supposed to be fun, remember?" He wanted to ask for who, but stayed quiet. "So many toys," she mused. When she faced him, his eyes drank in the beauty of her naked, young body. He admired her firm, perky breasts and the long, hard nipples that stood out proudly from those twin swells. Below her flat stomach, he saw she was shaved. Her pussy looked puffy from her recent orgasm. "Got anything to eat around here?" she asked, turning and heading into his kitchen. She opened his refrigerator as if she owned it.
Setting aside two cups of yogurt, she rummaged through his kitchen drawers until she found two spoons. Pulling the top off one, she held it in front of his prick. "Jerk off," she told him. In need, Derrick began stroking his cock. She watched him, a pleased look in her eyes. "Fuck that looks hot," she said. As his orgasm neared, he aimed his cockhead at the open container of yogurt. He didn't need to be told that's where she wanted his orgasm. The force of his orgasm rippled the yogurt. "Good," she said, stirring the yogurt before handing it to him with the spoon still inside the cup. She picked up the other one from the counter. "Go ahead. Enjoy," she said, spooning her untainted yogurt in her mouth. Derrick ate his, aware that he was eating his cumshot at the same time. He felt humiliated and excited by the idea.
Terri's eyes danced across him as openly as his eyes absorbed her. "How's the yogurt?" she asked.
"Good," he said, not sure he tasted the semen.
"How long before you get hard again?"
Arousing Family Page 98