tagAnalCatching Jennifer Red-Handed

Catching Jennifer Red-Handed

byJRob©

Jennifer McDougall slumped in the hard-back chair on the other side of my large wooden desk. The wind knocked out of her sails, I knew she was beaten.

Tears ran down her face, and I handed her my handkerchief to wipe them away. It was a losing battle though, for each time she dried those blue eyes the tears continued to flow.

"Mr. Roberts, I'm so sorry, I..." she quietly said.

"Now, now, Jennifer. All is not terrible. All is not lost. Why, with a little luck you will be home with your little ones in later today," I calmly said.

Still, the tears flowed.

I stood, walked around to the front of the desk, and stood in front of the crying lady, a sympathetic look on my face. I stared at Jennifer, the 25-year-old woman who worked in the accounting department of my firm. It appeared she might collapse from the circumstances and fright.

My look changed to a leer, though, when I reached down to the zipper on my pants and slowly lowered it right before her crying eyes. Looking directly into those baby blues, I reached into my boxers and slowly pulled out my hardening cock. Her eyes saucered as I began stroking myself just inches from her face.

"Well, Jennifer, I think it's time for you to suck my dick!"

She pulled her head back as the tears began flowing like a stream after a rainstorm. She appeared to want to jump up and run away, but her body wouldn't move. She just stared at the hard cock in front of her.

"Suck it," was all I said.

Her terrorized reply was simple. "I can't."

"Oh, you can Jennifer. You can and you will...if you know what is good for you."

Silence rocked the room as we stared at each other.

The woman looked away from my dick and after thinking for a while she looked up at me.

"Mr. Roberts, I have never done that. I can't do it. I won't do it."

That made my manhood extend to its full six-and-a-half inch length. It pulsed in my hand as I continue to jerk it off toward her face.

"What about your ex-husband?"

"No....never."

"Ever?" I asked, incredulously.

"Never."

I thought for a second, then reached over and grasped the back of her head. "Jennifer, there is always a first time."

With that I pulled her head forward, and while at first she attempted to pull away it wasn't long before my cock was rubbing against her face. I held my dick against her cheeks and rubbed. It felt great, but there was more work to be done.

"Open wide, Jennifer. This cock's for you."

I place my dick directly against her closed lips and slowly pushed. She attempted to move her head away, but I refused to let her get away. I held her head with one hand, then pinched her nose shut. As expected, within a few seconds, her mouth open and in popped my dick.

At first she gagged, then I thought she'd bite me. But I just remained still inside her mouth. After a bit, the gagging and her attempts at removing my cock stopped.

"See, Jennifer, it's not that bad. My cock may look big, but that's just because you are so beautiful and your lips are so soft," I cooed at her. "Now, just rock it back and forth in your mouth, and suck on it. Suck on it like it was a straw."

What young Jennifer lacked in experience was more than made up by the angelic look on her face as she sucked my throbbing cock. I barely moved, allowing her to feel my dick in her mouth. It wasn't the best blow job I had ever received but it was in its own way tantalizingly hot.

The girl slowly moved her head toward my body then away, sucking all the while. Her eyes were closed, her hands trembled, her breasts heaved. It was a lovely sight.

My mind wandered back to this morning, when Jennifer's life turned upside down.

Jennifer had been working for my company a little over a year, forced to return to the workforce after two kids and a failed marraige. Her husband was a drinker, and apparently he beat her on occasion, and after attempting to stay together for the sake of her kids she finally gave up and filed for divorce.

She started as an accounting secretary --- it was her shapely legs in her short skirts which originally won me over --- but was promoted to accounts payable clerk a few months later. All was perfect except for one thing that recently came to my attention. Jennifer was stealing from the till. Not a lot, but when I began reviewing her books I noticed that a surprising number of checks were written for a temporary help firm I knew we hardly used, I knew something was wrong.

I checked with the company, was assured we hadn't been using them to the degree in question, and then formulated my plan. The money wasn't a lot, a couple thousand dollars. I called Mike Newtown, a former police officer who now was a private detective. And over beers he reviewed, sliced and diced the evidence. It was a clear case of embezzlement. Over dinner, the plan was hatched.

Earlier today I called Jennifer into my office and confronted her with my findings. She broke down, admitting everything, but said in her defense she had to do it to buy clothes for her kids and pay the rent. It seems her deadbeat husband wasn't paying his child support, and her credit cards were maxed out.

I explained that wasn't my problem, and had my secretary send in Mike Newtown, who was dressed in a police officer's Sunday best outfit.

"Yes Mr. Roberts, I came as soon as I could," he said, playing the part to the "T". Is this the embezzler?"

Jennifer cried. "Oh, no," she said in nearly a whisper. "No."

I gazed at the woman. "Well, Jennifer, Officer Newtown is with the bunko squad, and it appears like you and he will be spending some time together writing your confession and an apology to the company. In return I will not press for a long jail sentence, and I will put in a good word at the child protective services agency so that your kids will be in a good foster home while you are in the state penitentiary."

Shocked, Jennifer looked from Newtown to me and back, tears flowing from her face.

"You are looking at three years," Ms. McDougall. "But I think with good behavior you will be out in a year-and-half."

She continued to cry, and babble something about paying the money back. I pooh poohed her answer by saying that she had no way to pay it back, and besides, since the officer had already been brought in that it was out of her hands.

We led her into my conference room, and with a florish, left her inside, locking the door.

Mike and I went to the coffee room and smiled at each other. "I think I can talk her into working her way out of her predicament," I said. "What do you think, a month of blowjobs?"

"That will do, as long as I am included," he replied. "Did you get a look at those lips. Beautiful. Even though she's bawling her eyes out those lips look unbelievably sexy."

We decided to let her stew for a while before I hit her with her alternative "sentence." In the meantime, I found the number of her ex-husband and gave him a call.

I got through to him, but barely. Although it was only 11 in the morning, he had already been hitting the bottle. After some chatter, I asked him about his wife.

"She's a no good bitch," he slurred. "I hate her fuckin' guts."

"But surely she had some good points," I replied. "You had two kids with her."

"Yea, but she's a bitch."

"Why's that?" I asked.

"We were married four years and she never once sucked my dick," he spat. "I am getting her back, though, I'm using the child support to pay for a whore to suck my dick. That will teach her."

I laughed at the new knowledge. Then and there I knew how we could solved all of these problems at once.

We talked for a bit more, then I told the man to be at my office at 3 p.m., that there was a bottle of Jose waiting for him as well as $25 if he showed up for an hour's work. He assured me he would be there.

I arrived back in my office and smiled as I hear Newtown interrogating Jennifer in the conference room. I laughed to myself as I could hear her pain. She was a caged animal, she begged for understanding and forgiveness, but Newtown didn't budge.

After a while he retired from the conference room closed the door, and shot me a thumb's up. He walked to my desk and whispered that Jennifer was scared to death about prison, being removed from her kids, and having the stigma of being a thief on her resume for life. In short, he said, she was ready for "the deal." He rubbed his crotch...."She's in your hands, Jonathan, make it good. I will be down the hall, and I hope this worked out because Mr. Happy here needs some love and affection."

Jennifer sat in the conference room as I paced my office. I wanted her to be desperate. After a half hour or so I opened the door and called her into my office.

I pointed to the chair across from my desk. "Sit down," I sternly said.

"You have a big problem, young lady. I appreciate your confession, and the apology," I said, pointing at the documents on my desk. "Do you have anything to say for yourself before Officer Newtown takes you downtown."

The young girl opened her mouth but the words didn't come out. She continued to cry, and finally said the words I was waiting to hear. "Mr. Roberts, there must be a way. Please, I am begging of you. Help me get out of this. I will do anything to stay out of jail and keep this out of the papers."

"Please, anything. Look, give me a chance and I will work for free to pay off the debt. I will get another job," she said.

"You know, I believe you," I replied. "But it will take more."

I looked at her in silence. After a bit I loked her straight in the eyes and started laying out what I hoped would be the makings of a deal. "I have needs. My wife no longer has sex with me..."

The look she gave me through those crying eyes was precious. It was as if a light went on in her head. "Of course, Mr. Roberts. Help me out of this and I would make you happy...uh, that way. Please, we can make a deal."

"Oh, make a deal we will. But it is not charity. You will have to work to pay off this debt."

I looked at the woman and smiled but she continued to cry.

My mind snapped back to the woman sucking my cock. It had been a tough day, a day of charades, a day of convincing her that she was at the end of her rope. A day of Mike Newtown giving an Oscar winning performance. A day of making small talk with Jennifer's ex-husband.

Now it was a time for her to suck my dick. She wasn't the best cock-sucker I had ever sampled, but it was kind of sexy watching the woman give her first blow job. At first I hadn't believed her, then I suggested to her husband that he must be mistaken. All admitted the girl was not a cocksucker. After a few minutes of her sucking my dick I realized they weren't lying. But it was a a blowjob nonetheless, and that old saying that no blow job was a bad blow job held true as I watched the woman work on my cock.

She cautiously moved her mouth up and down my dick, sucking all the way. I pulled my dick out of her mouth and told her she was doing fine, then told her to lick my dick. She did, lapping at it like a cat to a bowl of milk. Then I slipped my dick back into her hot wet mouth and allowed her to suck some more.

Watching her, my cum started boiling in my balls. My eyes never left her lips as my dick began pulsing before letting go of a heavy stream of spurting. The woman gagged, my dick slipped out of her mouth, and I grabbed it and began jerking off on her face. The sex, the power, the control was an awsome feeling.

"Excellent, Jennifer, excellent. You have unexpected talent!" I said as the cum hit her nose and forehead.

The woman enexpectedly swallowed some of my cum, a look of displeasure coming over her face, and she used my handkerchief to wipe the rest of the sticky stuff from her face.

"Now, that wasn't that bad, now, was it, Jennifer?" I smuggly asked.

"No, Mr. Roberts, I guess not," she replied, asking hopefully: "Am I off the hook?"

"Oh, no, Jennifer. That was merely the payment of some interest. There is still a full block of repayment you will have to perform to get out of your predicament."

The girl nodded her head, and calmly said, "I figured as much. I appreciate you giving me a second chance, Mr. Roberts."

I thought to myself that the girl was coming around. I looked her in the eyes, and explained the terms which must be adhered to before I would let her off the hook.

"First, for the next month, Friday afternoons will be reserved for more fun in my office. You will be my whore for four Friday afternoons. Let's say from 3 to 5 p.m. You will continue working here, of course, but for the minimum wage."

Her face displayed shock, but "Ok" was all she said.

"Second, on those Fridays, you will dress for work as follows: your hair will be in ponytails, you will wear a white blouse with no bra, and you will wear a short pleated red schoolgirl skirt with no panties. You will wear knee high black stockings and black patent leather shoes. If anyone asks, you will tell them that you just love your schoolgirl outfit."

Jennifer's eyes nearly popped out. I could tell her mind was swimming with embarassment, but she simply said, "Ok...is that all?"

"Just one other thing. For the next two hours or so you will do as I tell you to do."

"And if I do all that I will not have to deal with the police? I will not have to go to jail?"

"Exactly. I will keep your confession, and I will constantly check your work. If you stray again I will use that confession and apology to send you to prison."

Jennifer nodded her head. "I understand," she said, wiping away some stray cum from her cheek, cum mixed with tears. "I will never steal again. I will be your most dedicated employee. I will do whatever you ask, and when the month is over I will prove to you I am a dedicated employee."

I knew she would. There was no way she wanted to be separated from her kids. My alternative kept her with her kids and away from jail.

"Ok, your time starts now, are you ready?"

"Yes, Mr. Roberts. What do I have to do?" she questioned, noticing my flacid dick.

I buzzed my secretary. "Please send in officer Newtown, Ms. Quimbly.

Minutes later the door opened and the pseudo policeman entered the room.

"Jennifer, I think the officer needs to sample your newfound talent. Treat him nice."

The woman nodded her head.

The "policeman" looked the woman up and down, then commanded: "Jennifer, unbutton your blouse. We want to see your tits."

Like a zombie, the young woman revealed her perky breasts to our view. Newtown admired the girls' 34 B's, gently feeling them as if they were fruit. Then he told young Jennifer to get onto her knees.

She knelt before the policeman, opened his pants up, and reached in for his cock. She pulled out his massive nine inch dick and pushed her head back. "Oh my god it's huge," she said. "I can't suck that."

Newtown laughed. "Oh yes you can, Jennifer, and you will. First, lick it."

The girl opened her mouth and extended her tongue. She licked the hard cock up and down, then began sucking the tip. Her head bobbed up and down on the crown of his cock, but she had a hard time getting more than a couple inches into her small mouth.

Newtown looked at me and said the girl had talent, but he wanted something different.

"Go ahead, she's yours," I replied.

The cop nodded and continued to thrust gently in and out of the girl's mouth. Jennifer attempted to take more of his dick in her mouth, but obviously had trouble with the massive cock. After a few more thrusts Newtown patted the girl on the head and pulled his dick out of her mouth with a plop.

Jennifer looked at the man and asked if she had done something wrong. Newtown assured her she hadn't, but that he wanted something else: her pussy. She nodded her head as he told her to bend over my desk. The girl rested her head on her hands on my desk, looking at me sitting in front of her. Newtown lifted her skirt, pulled down her panties, and moved into position behind her. He rubbed his cock up and down against her wet pussy slot.

"Um, go slow please," Jennifer said to the man. "You are so big."

Newtown slowly inserted his big dick into the girl's cunt. He moved back and forth a few times before slamming his dick into her pussy to the hilt.

"Ohh!!!" she exclaimed. "I've never felt so full."

The girl reached down and began fingering her clit as the man banged in and out of her pussy. She moaned at each thrust, while he grunted as he fucked her hot wet quim. "Oh, baby, your pussy is to tight," Newtown said. "I love it."

The two rutted for a while, with the girl getting into it.

"I'm gonna cum," said young Jennifer, firing her ass back at the man. "Umm it's so goooood."

The man's head rose toward the ceiling as the cum began to boil and rise from deep within. He began shooting his cum into the girl's pussy, and that ignited her own cum. I watched in awe as the twosome came together.

Newtown collapsed atop the girl, the two of them breathing heavily.

"Well, Jennifer, it appears you liked that."

"Oh yes, Mr. Roberts. That was fantastic! I can't remember feeling so good. That was tremendous."

"Well I'm glad you liked it, but you still have some time to work as part of our deal. Are you ready to continue?"

The blonde girl lowered her head and nodded. "Oh yes sir. I'm just so happy you are helping me out here. I'm so sorry I did wrong, but I'll tell you if I knew Mr. Newtown would be my punishment I would have been caught a lot sooner," she said with a sly sort of smile.

The girl sat back in the chair across from my desk. Her panties were on the floor, her lipstick smudged, she had that freshly fucked look of contentment as she waited for her next assignment.

The smile on her face disappeared when her ex-husband was ushered into the room.

"Oh My God, NOOO!!!!" she cried out. "Get out of her you bastard!"

"Now, now Jennifer. You are still on the clock and there's time left in your workday," I sternly said.

Blood drained from her face as she looked at the man with distain. She knew she was under my control, and had to comply with the terms of our agreement.

"What do you want," she quietly asked her ex, knowing in the back of her mind what was coming next.

The man pointed to the ground in front of his cock, and she nodded and slithered down to her knees. He whipped out his dick and rubbed it against his ex-bride's face. "I've been waiting years for this," he said, watching as his ex-wife, resigned to her fate, opened her mouth and began orally attacking his cock.

The girl worked on her ex-husband's dick as best she could, but the man made things difficult by pulling it out from her mouth to rub it all over her face. He spanked her cheeks with his dick, then inserted it back into her mouth and attempted to jam it down her throat. He seemed to get off on humiliating her.

The blowjob continued for several minutes before the man pulled the cock out his ex-wife's mouth. "Bend over the desk," he commanded, and Jennifer compiled. At first she figured a fuck would be a lot better than his mauling of her mouth. But when she felt his dick against her anus she cried out "No!"

"Oh yes, little darling," her ex-husband said before attempting to push his rock hard, hungry dick into her small, tight asshole. It wasn't easy taking her anal virginity. She was dry as a bone back there, and the man spit on his dick to get it moist. He put one hand on her back to hold her down, while with the other he jerked his dick against her ass, then her pussy, then her asshole again.

She continued to try and pull away, but it was in vain as her Ex was a man on a mission. He pushed and prodded and forced his big cock at her anus.

The girl cried out to no avail, as her ex-husband began living his deepest fantasy, slipping his cock into her darkest hole. Jennifer cried out in pain as his dick broke her anal cherry.

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byJRob© 5 comments/ 221823 views/ 4 favorites

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