20 year old Terri dominates her 40 year old boss

An early spring rain pelted the parking lot, dropping the temperature to a new low. Inside the frozen yogurt store, Terri shared at one of the round tables with her boss, Derrick McIntire, waiting for customers they knew would be rare. The dark storm clouds triggered the electronic eyes of parking lot lights, adding to the gloom. Inside the brightly lit store, Derrick grinned at the faint blush on Terri's cheeks. "Wow, what are you reading that can make you blush?"

"Porn," Terri replied, looking directly at him though her cheeks were pinked with embarrassment. When Derrick laughed, he saw her embarrassment fade as her eyes narrowed. "What's funny about that?"

Derrick considered where to start his list. Terri Saunders had all the hallmarks of being an innocent. Her sunny demeanor matched her blonde hair, blue eyes, and sprinkling of freckles across the bridge of her nose. He hired her because she was perky. Quick witted and smart, she laughed easily and weathered the rudest customers with patience beyond her twenty years. Once he tried giving her a guest spot in a fantasy. Stroking his hard cock, he got as far as imagining her bare, small breasts before giving up and replacing her with someone else. Terri Saunders was too much of a good girl to star in one of his masturbatory delights. "How you blushed," he said.

"So what do you use when you're doing it yourself? Probably videos, right?"

"Usually," he said, wondering if his cheeks were turning pink, too. "So, what kind of stuff are you reading, erotic romances?"

"Ew, you're not even close. Tell me what kind of porn you like to watch and I'll tell you what I like to read."

Considering her condition, Derrick felt a stirring in his lap as he imagined telling her the truth. He wouldn't. No way. "The usual stuff," he hedged, earning another steely eyed glare from her. "Seriously, just man on woman stuff. Now your turn." Her answer surprised him.

"Mostly hardcore BDSM erotica."

When Derrick started laughing, he earned another glare, but he couldn't help it. The idea of this sweet, innocent girl reading hardcore anything was funny enough, but BDSM? He struggled to rein in his laughter. "Sorry. I just, I don't know, wasn't expecting that answer." Terri didn't looked hurt by his laughter, she looked pissed. His glee faded. "So, um, what's the attraction?"

"Being in control," she said. "Making people do stuff."

Derrick chuckled. He liked Terri's personality, but it was her work ethic that had room for improvement. Lazy, she never displayed a single trait of leadership. "Like what?"

"Everything. Anything," Terri answered with a shrug. "Kinky stuff. The kinkier the better." There was a faraway look in her eyes as she stared at a spot on the wall just over his shoulder. She shivered. "I just think it would be hot to own a real sex slave."

"Well, let me know when you're taking applications from forty-something old guys." Once again, her answer surprised him.


Derrick considered the pretty blonde for a long moment. Could she be serious? "What if I wasn't joking?" he floated.

"What if I'm not, Mr. Mac? Do you really want to be a tool with no rights, forced to worship me without a promise of release and to cater to my every desire, no matter how sick or twisted it may be?"

He held her gaze before chuckling. "Now who's the tease?"

"Show it to me," she said, never cracking a smile.

"Show what?"

"You heard me. If you want to do this, then let's do it. Show it to me. Right here. Right now."

"You'd freak if I did."

"No, I wouldn't. But I would have accepted you into my service."

"What do you mean, 'would have?'"

She patted his hand. "Slaves have to be strong, Mr. Mac."

"You're saying I'm chicken?" he asked, wondering if it was a game.

"I'm saying you're not made for a life of service and you just proved it."

"Ask me again."

"Wrong answer," she laughed. It took him a moment to catch up with why it was wrong.

"Sorry," he said, realizing it wasn't his place to ask her for anything.

"Thanks better," she acknowledged. Tilting her head to the side, she considered him for a moment with half a smile on her face. "Make it hard for me and we can try this again."

Derrick felt his willpower fading. He had bought a fitness center membership in hopes of meeting a higher caliber of women. For three months, he worked off his middle-aged spread; tightening and toning his body into a shape the twenty-something version of him never knew. Proud of his new body, he was frustrated each time he spent time with another woman in his age bracket. He deserved better, but three months of doing it himself had worn thin. Grabbing the front of his work khaki's he rubbed the beginnings of a hard-on. "You know I'm really going to do this, right?"

"I'm counting it," she said, grinning as her eyes flickered towards his crotch.

"Want to go into the backroom?" he asked, feeling his hard-on reaching acceptable lengths.

"No. Right here. Right now. Stand up, pull your pants down, and show it to me. If you're not hard, the deal's off."

"And if I am?"

Leaning across the table, she propped her chin in her palm and held his gaze. "Then it's playtime for me. Now show it to me, bitch."

On the wrong side of forty, he was too old for this. He knew better. He was risking his reputation and job. At barely twenty, Terri was too attractive and vibrant to want him. He knew this was just a game for her. What if he did it? Risking her laughter didn't give him pause, it was losing a good team member weeks before things would get busy. But life is made from tiny choices made on the fly. Working in steps, he undid his belt, the button at the top of his khakis and worked his zipper while staring at her. Terri held his gaze, her eyes never wavering from his. Reaching inside his underwear, he laid his hand the long, firming rod of his manhood. He caressed the instrument of his pleasure, wondering what her reaction would be. While he wasn't blessed with porn star proportions, Derrick wasn't embarrassed of his length or girth. He knew he had more than most and those with more were few. Letting the smaller head made the final decision, he stood.

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.
17824 days ago, 15109 reads
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