The following is a work of fiction. All characters are at least eighteen years of age.
*****
"Yes Miss Featherly," John mustered through clenched teeth.
"Yes, you did pleasure yourself, or Yes you did not?" Crack the yardstick came down roughly on his bare ass.
"Yes Miss Featherly, I did, I am so sorry."
Crack the yardstick found its target again and then again. John's ass was a mess of red streaks. His eyes were beginning to water from the pain. He was leaning over her big wooden desk again naked. Both fists grabbing the edges of the desk firmly. She was standing behind him wearing a white pushup bra that exposed the tops of her two beautiful breasts along with her nipples and areolas. Her legs were clad in pristine white stockings held up with a garter. Her pussy was bare, showing off its glistening jewelry unashamed. Silver rings hung heavy from her full lips, and a steel bar hung from her clitoral hood.
His first instinct was to stand straight up and grab the yard stick and start slapping her with it.
Crack, another blow found its flesh target.
But he needed the grade. His life as he knew it depended on his passing her class.
Crack.
Also, somewhere deep down he knew he deserved this punishment. He had been so turned on ever since leaving Miss Featherly's office three days ago that he couldn't think about anything but her. He didn't plan on masturbating. He was just in bed, hard, and lightly touching his cock as he anticipated what might take place in their second session.
Crack.
The thought of Miss Featherly playing with her pierced little pussy inches away from his face the last time he was in her office was too much. He started to panic as he felt himself go over the edge. He tried to pinch the base of his cock but it was too late. What felt like buckets of cum shot out of his throbbing member and drenched his sheets.
Crack
"You are going to have to learn some discipline if this is ever going to work out Mr. Williams."
Crack. Margarette was beginning to tire from all of the exertion. She stopped to rest for a moment and noticed that John was getting hard again. She touched his semi erect cock with the yardstick and smiled.
"You really do love this." She stroked his cock with the ruler. " and you are so resilient. I love how you young boys can recover so fast "
It was fast. Just a few moments earlier she was milking his cock with her hand as she explored his virgin ass with her finger. She really enjoyed his cock. It was very thick and of ample length, but there was something else. It was simply beautiful. It was hard for her to explain what made some cocks beautiful and others just pieces of ugly flesh, but this one had that special something.
She had him stand by the desk as she knelt before him and stroked him. She was trying to teach him that she was in control even when she assumed a position that was below him. As she stroked him she knew he had a great view of her breasts. She had applied just enough makeup to her nipples and areolas to make them stand out.
To further her point of control, she reached behind him and toyed with his ass hole. He was so tight, as was to be expected. Since his cock was now oozing precum, she used some of this natural lubricant to moisten his entryway. Eventually, as she encouraged him to relax, she inserted a dainty finger. His ass clamped down so hard it felt as if her finger would be severed, but she just increased pressure on his cock to ease his reluctance. He had never had anyone play with his asshole like this. It felt strange at first and he fought it, but now as he relaxed a bit it felt strangely so good. It was as if a new part of him was coming alive.
"Miss Featherly. Uhh. I am going to cum if you don't stop. " He had almost yelled.
"That is fine Mr Williams, in fact it is the point." She could feel his cock begin to twitch so she stopped milking him and grabbed a clear plastic cup from behind her and held it to his tip.
"Stroke yourself to orgasm Mr. Williams. Fill my cup with the seed you have been saving up for me." She plunged her finger deep into his ass skillfully finding his prostrate and applying the perfect pressure.
His eyes went dark with the most powerful orgasm he could ever imagine. His cock pulsed jet after jet of creamy cum into her cup. As he basked in the post orgasmic bliss he heard Miss Featherly clucking her tongue disapprovingly at him. He opened his eyes to see her now standing in front of him holding a cup of his sperm.
"You clearly did not listen to my order. This is not three days worth of sperm. Now bend over and grab the desk. It is time I teach you to obey."
And that is where they were now. She was taking a break from spanking him with the yardstick, and now in a bit of awe at how quickly he regained his erection. She was also pleased at how much he was enjoying the flogging. He could end up being a fun one. If he took to her training.
"So you enjoy me hitting your naked ass with the yardstick?" She asked as she continued to trace his hard cock with it.
"Uh. I guess Miss Featherly." John answered honestly. He wasn't sure what was turning him on, but what was undeniable was the fact that he now had a raging hard on again.
Quick as lightning she gave his ass a hard smack that made his whole body move forward.
"Guessing is not acceptable Mr. Williams."
"Yes Miss Featherly. I like it. I like it when you hit my ass."
"Good boy." She was now stroking his cock with her smooth hand and it felt amazing. Her other hand was gently massaging his red ass with the wooden yard stick.
"See, so much pleasure can be found in a little pain." She was bent over him now talking just over a whisper into his ear. She pressed her chest into his back, and he could feel her hard nipples. "But first you must learn to obey. " John could feel another orgasm building up rapidly in him. He was amazed at how quickly she could get him off. She must have sensed his impending eruption because she stopped suddenly. She pulled herself away from him and he could hear her rustling in a bag. Then her mouth was at his ear again.