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"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.
