Catching Jennifer Red-Handed


"I thought your mouth would be great, but this is unbelievable," he said as he fucked her virgin ass. The man rocked in and out of her ass, eliciting cries of pain from the girl who pleaded with me to have her ex-husband get his cock out of her asshole.

"Please, Mr. Roberts, please. Anything. Please get him off me."

"No, Jennifer, you brought this on yourself, you have to pay the price." I calmly said.

She closed her eyes and I saw her trembling body slump on my desk. Resigned to her fate, he lay there as her ex-husband fucked her tight ass. The excited man was fucking Jennifer's shitchute hard, and I could tell it wouldn't be long before he would be cumming.

I was right, as he cried out to the world that he was shooting his load into his ex-wife's ass. "This is for all the grief you gave me, take it," he said as his dick exploded.

He pulled his dick out of Jennifer's ass and pulled up his pants. "Thanks man, that was great." With that he slapped his wife's backside, thanked her for her ass, chuckled, and then left the office.

Jennifer remained over my desk, resigned to whatever came her way. I moved around behind her body.

"I'm going to fuck you in the ass now, Jennifer," I said, slipping my hard dick out and rubbing it against her cum-drenched asshole. The passage was slick from her ex-husband's cum, and unlike his difficult entry mine was relatively easy. I slid my dick into her ass and remained still as she got used to my girth.

"Mr. Roberts, you can fuck me back there, it's okay. Once he got going it was actually decent, but I didn't want to give him the pleasure of knowing that."

I held the girl's ass cheeks and slowly rocked inside her tight ass. The feeling was wonderful as I rocked back and forth. "Jennifer, your ass is so very tight," I said in between pushes.

Jennifer's backdoor felt spectacular around my dick. I pushed hard, inserting my dick as far as it would go, then grabbed onto her tits and pulled myself in and out of her ass. I had been up the chocolate speedway a few times, but this was extra special.

The young woman pushed her ass back at me, her butt chute taking all of my cock, surrounding it with wonderful sensations. I held her ass cheeks in my hands, rocking against her. After a bit I bent on top of her and reached around to fondle her tits, eventually leaving one hand with them and moving the other to her pussy. All the while she moaned as I pounded her asshole.

Needless to say, it wasn't long before I told her I was going to cum.

"Cum in my ass, Mr. Roberts, I want you too."

That did it, and I spurted my sauce into her backdoor where it mingled with the cum of her ex-husband. I kept fucking her ass until my dick shrunk and plopped out. The girl, worn out from the afternoon's activities, slumped back in her seat. She looked a mess, but I could tell there was a feeling of relief that she wouldn't be prosecuted for her felonious actions.

The blonde girl steadied herself, rose and smoothed down her skirt, looking at me as I zippered up my pants. There was a bit of uncertainty as we looked at each other, as if searching for words to say. After a bit I thanked her for keeping up her end of the bargain, and firmly stated that more anal action was in the offing.

She told me that would not be a problem, that she knew what she had to do. She added that she had learned her lesson. "I know I did wrong, but I hope this afternoon proves that I am willing to make amends."

I couldn't believe my ears. I had done my best to humiliate her, and here she was thanking me.

"Just remember," I said. "You will have to perform for me a lot more over the next month to pay your way out of this predicament."

"You can count on me," was all she said.

And I could. Jennifer did not renege on our agreement. In fact, she performed her duties with a smile, despite hearing all the women in our office talk about her behind her back.

"She must be fucking him, there's no way any self-respecting girl would wear that outfit to work unless she was being boned by the boss," I overheard one woman say of Jennifer's schoolgirl outfit.

"What a slut," said another.

Jennifer was adorable on Fridays. The short skirt and white blouse, to say nothing of her pigtails and knee high stockings, made her look like a young college girl. Several men who had appoinments with me commented on the girls lack of panties.

When our afternoon appointment came around she was alway prompt, entered the room with a smile, and allowed me to have her in whichever way I wanted. While our trysts generally started with a little oral action, it always ended with my burried to the hilt up her Hershey highway. Over that next month I receive more ass-fucking action than I had in my entire life.

Jennifer learned to enjoy my fucking of her tight ass. In fact, on one occasion she asked for it without being prodded.

"Mr. Roberts, I want you to fuck me up the ass today."

Always the gentleman, I complied with her request.

(Epilogue: Upon completion of our deal, Jennifer McDougall went back to her old salary and became one of my hardest workers. Although she didn't have to wear her schoolgirl outfit, she did, teasing me relentlessly. A few weeks later she asked for an appointment and asked me for a raise. I told her money was tight, but she said there was always a little extra...for a price. She suggested we resume our Friday afternoon meetings in return for a raise. I agreed that it was a small price to pay for her work ethic. After all, I am a good boss who cares about his hard-working employees.)

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