A few targeted strikes

Steves finger circled around Catherine asshole. She was no stranger to assfucking, but it was not an everyday occurrence. Occasionally, her husband would use her like that, but that only happened as part of punishment sessions. Sessions such as the one she found herself in now, the only difference being that the man doing the punishment was a coworker, not her husband.

Then the finger disappeared. Catherine held her breath, ready to be penetrated by something thicker… which did not happen.

“Spread your checks for me.” Steves voice was not malicious, but didn’t hold any compassion either. Punishing his coworker was a part of his job, and a part he would do as professionally as any other tasks he had. His own enjoyment was secondary, although he could not deny that the sight of Catherine opening herself for him made him hard. There would be a time for that later.

Catherine did as ordered. Her hands, which had held onto Mr. Greenes desk, slowly moved around and grabbed her butt. She was very aware that her meaty asschecks were her last line of defense, and that she offered an absolutely inviting target by spreading them.

“Mr. Miller, what will you do to me?” Her voice was almost too soft to hear as she asked. She was afraid of the answer, but not knowing was worse.

And then she found her answer! “YEEOOOWWWWWW”, she bellowed, as a sudden pain shot through her body. Steve Miller, boring Steve Miller, who built model railroads in his spare time, has just landed a perfect cane strike directly at her exposed anus. Right at the spot where the nerve endings met. Catherine could not hold back tears, and instinctively moved her hands to cover her oh so sensitive nether regions.

“Pllleeease, mr. Miller. Pl..please don’t…” It was all she could do to **** words through her sobbing. And this was caused by just one perfectly targeted strike.

“Silence, Catherine.” Mr. Miller was still not angry. Somehow, this made it even worse. He was not a sadist and was not doing this to her because he was angry. He simply knew how to provoke the most pain as efficiently as possible and was using this knowledge to finish the task at hand. “I shall strike you four more times. If you move or attempt to cover yourself, I might miss. Such misses, while still painfull, will not count against the strokes I will administer. Do you understand?”

*Sob*”Yes, Mr. Miller… I.. I understand.”

“Good. Now spread your cheeks again”

Catherine did as ordered. With shaking hands, she offered up her defenseless ass to her punisher. “Sir… could I have the gag back?”

Mr. Greene had been silent until now. If he had any objections to Steve Millers chosen punishment, he had not voiced them. Now he sounded almost kind as he answered her question. “Off course, Catherine. Steve, if you would wait a second.”

Catherine willingly opened her mouth as Mr. Greene fastened the gag again. It had been left on his desk when Chloe removed it, and was still wet with her spit from the last use. As he gagged her, Mr. Greene even wiped away the tears from her lovely face. “Bite into this, Catherine. Be brave, this will soon be over.”

And then the short respite was over, and Steve resumed his attacks on Catherine tender asshole. The gag silenced her screams, as Steve proved to be a master of the cane. With surgical precision, he managed to land every single strike directly at her dirty hole. After the second strike Mr. Greene started to stroke her hair and whisper comfort to her.

As the fifth and final stroke landed with marksman like accuracy, Catherine was reduced to a sobbing and crying mess. Her eye were red and swollen. Mr. Miller had carefully managed not to damage her, but every movement hurt so much. And despite all this, Catherine did not hate.

These men did not hate her. They cared for her, and only wished her to be as effective as possible. She had made a major error and was now paying the price. Once this was all done, they would all be colleagues, and this would be a distant and painful memory.

As her sobs subsided, Mr. Greene once again removed the gag.

“Thank you, Mr. Miller.” Catherine managed to whisper the mandatory sentence.

“No hard feelings, eh, Catherine. We better not repeat this. Oh, did I say 5 strokes? I dropped a digit, I meant 50.”

Catherine was close to tears just at the thought of another 45 of these masterfully targeted canings. In that moment, she was sure she would never survive such pain. And then she heard Mr. Greene laugh.

“Good one, Steve. Now, back to work with you.”

Steve laughed as well. This punishment had left him somewhat horny, but it was obvious that he would not be allowed to fuck Catherine. Oh well, there were other women in the company, and tension relief was an important part of their duties.