Jenny Goes Undercover - Cover

Jenny Goes Undercover

Copyright© 2012 by neff trebor

Chapter 1

Fiction Sex Story: Chapter 1 - Jenny's husband asks her for help. He is an undercover cop. Jenny is unwittingly duped into being used by both sides of the law.

Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa   NonConsensual   Reluctant   Coercion   Wimp Husband   Cuckold   Wife Watching   Humiliation   Group Sex   Interracial   White Couple   Black Male   White Female   Oral Sex   Anal Sex   Cream Pie   Size  

Jenny Marie Jenkins turned off the sprinkler in the back yard and put away the shears. She piled the cut spirea branches into the big plastic garbage cans spaced along the hedge. With the branches that were sticking out cut off, it would be easier to run the riding mower closer to the hedge. She dusted of the fine white flowers that had gathered on her clothing.

The grey wool hunting socks that were folded over the top of her chocolate colored lumberjack boots were covered with the little critters that had blown off of the plants as she cut them. Her cut-off Levi's had quite a few of the flowers trapped in the folds at the edge of her shorts where they had been turned up. "I need to just cut them and hem them a little shorter." She thought to herself. On the other hand, the length of her cutoffs seemed tied to her attitude for the day. If she was going into the store, she usually left them turned down with the edges just about mid thigh.

When she was working in the garden in her back yard, she turned them up as far as they would go to get more sun. If it was a real nice day, she would take them off and just do work in her bikini bottoms. The same with her top. The thin light cotton shirt with ivory buttons was tucked into her waist band now, but she might also work with the bottom rolled up and tied in front of her, or she might even just work in the bikini top.

In this particular case, nobody seemed around, so she took the cotton top off in order to shake out the flowers in them. Jenny took of her huge straw Stetson and bent over to shake whatever flowers she might have in her hair.

She heard Joe's Wrangler turn into the gravel drive. She could tell what kind of mood he was in before he got into the house. If there was gravel flying, and the door slammed, she knew he had had a miserable Monday. He had been promoted to undercover vice several years ago and had been ecstatic about it at the time. As time went by, he became more and more frustrated at the cases he had been solving. The age of the arrested people stayed the same. He on the other hand was getting older. It was harder and harder for him to strike up a friendship or form a bond with the people he needed to break many of the cases.

"How did it go today, hon?" Jenny asked as she kissed him on the cheek and grabbed his arm as they walked into the house. "Same damned problem." He said in frustration as he threw his keys on the table in the entry and hung up his jacket.

"What's the problem now?" she asked, not really that concerned.

"It's that fucker Sam Cromwell. We know he is bringing in quite a bit of stuff from Mexico, but are having trouble tying him into it. He always seems to have somebody else doing the dirty work and he never seems to have any bank accounts or anything that ties him into the stuff we find." Joe put a cold cup of coffee into the microwave and set the timer.

"What would it take to get the information you need?" Jenny asked.

"Well, any kind of undercover cops we need can only last so long. Once they testify in court against somebody, everybody knows who they are. We have had to go farther and farther out into adjoining departments to find somebody else. The best way to gain this guy's confidence is with a woman. We have used up all of our decoys. Most of the others who might entertain the thought can't get their husband's or boyfriend's permission. Once they are identified, they are in danger.

"I'm sure you will find somebody soon." Jenny said as she handed her husband the hot coffee and kissed him on the top of his head. Joe sat there motionless for a few moments. He turned to look at his wife in her short, short cut-offs.

"Jenny, how would you like to make some good money?" He said like an idea just hit him.

"What do you mean hon?" He was always full of whacky ideas.

"We live in Kansas. The case I am working on is in Missouri, across the border. They would never know you. It might work."

"What are you talking about?"

"We need to get somebody to find out where Sam Cromwell keeps his money, who works for him; how the drugs get here and who he sends them to. He would never suspect you."

"Honey, I am 48 years old. You said so yourself that most of these guys are young. How could I gain his confidence if you can't?"

"Well honey, you could easily pass for a woman way younger than forty eight. You have a side to you that appeals to all men. I don't think it would be a problem."

"What would I have to do?"

"We would have to find a way for you two to meet. If you are around him much, you could overhear who he talks to. Maybe you could slip a GPS into his car or something. We can think of something if you are willing to take the chance."

Jenny was skeptical. "I guess I'll think about it." She said as she pulled the leftover spaghetti and meatballs out of the refrigerator and turned on the timer in the microwave. The rest of the evening melted into small talk of what their grown daughters were doing and the problems they were having.

A couple of days later, Jenny was out in the yard again, moving the paper bags of lawn waste to the edge of the drive for pickup in the morning. Her husband came rolling up the drive on two wheels and showering her with small gravel.

He grabbed her hand and walked into the house with her. He threw his leather briefcase on the table and pulled out several files. "Look what I have so far." He said as he spread several piles of paper on the table.

"There is a Jennie Marie Munson who is the same age as you. She has lived most of her life here in town and moved into the east side of town about four years ago. She was the city librarian until she recently left with a man to get married and go to Seattle. We have continued to pay her rent on her apartment and bought her car. You are going to get her job for the next six months. She kept pretty much to herself, so there aren't a lot of people who know her. What do you think?"

"What are you talking about?" she asked.

"I mean we have a pretty good cover for you. We could come up with some way to meet the guy and see what information you can get from him. What do you think?" Jenny could see that she was not going to get anywhere by resisting. He had already done so much work, she could hardly back out now. Maybe she could slip some kind of GPS in his coffee; he would drink it and they could track him.

"How dangerous is this going to be?" she asked.

"Well, hon, I hope you don't have to see the guy much and maybe you will be out of it soon. On the other hand, it could be dangerous if he ever finds out that we are married or who our daughters are."

Jenny didn't say anything, which to her meant she had not committed herself to anything. To Joe, it meant she had not objected, so everything was good to go.

"I'll come home tomorrow with a better plan." He said. In the meantime, why don't I take you somewhere nice to eat? It's Wednesday night." Jenny was too wrapped up in the excitement of going out to eat that she didn't realize what her lack of objection meant.

The next day, Joe came home and sat down at the dinner table with her. He was not so giddy now. "O.K. here's the deal as it stands right now. We have tapped his phone enough to know he will be meeting some friends Saturday evening at Guinevere's in the old Garment District at 8:00. We are thinking you can go there with some friends and bump into him somehow. You have to find a way to make contact with him. You may have to take a couple of your friends with you, or we could have a couple of the women officers go with you for company. There are several problems here. If you go with several women, he might pick one of the other women. I'm not sure what you can do."

"I'll take care of it, hon." Jenny replied without actually thinking through what she had just said. Joe gave her some photos out of a folder showing Jenny that Sam Cromwell looked tall and well dressed with an athletic build. Fortunately Joe had absolutely no idea Jenny once enjoyed incomparable sensual pleasure with a dozen different black team mates during 4 years in college. Sam Cromwell's appearance eerily resembled them.

All day Friday Jenny was totally preoccupied with her collegiate memories. Freshman year at college she was more often than not with a senior, Nkwame, one of the more popular football players. She had been a cheerleader and they were study buddies, but hadn't dated. Nkwame did not need to graduate. He had been assured by all the pro scouts that he would be taken in the first round. Both were sure he was leaving school making the dance after winning the bowl game her freshman year their first date rather than just hanging out.

No matter how hard she tried Jenny could not erase vivid memories of both being equally unsure. She clearly remembered Nkwame being disappointed without any sex that night. He was almost begging to go to a motel. As an alternative Jenny pulled her old Geo Tracker into a secluded spot in lovers' lane.

He had gotten her top, bra and panties off. Jenny was reluctant to stop or go any further. Against her best judgment, she allowed him to guide her hands to his pants. She unzipped him and helped him down with his jeans. This 300 pound lineman was well over six feet eight inches and could hardly fit in the passenger seat.

Once she helped him scoot his seat back and lower the back, she lowered her own seat and sat to the side of him on her knees. She grabbed the soft gathering of loose foreskin just below the crown with her left thumb and forefinger. They talked as she pulled the foreskin out and up away from him. They tried to keep the conversation informal and casual as she worked him into an immense erection. She ran the back of her hands along the sides of him. She leaned over and kissed the tip softly.

"Are you going to miss me when you are gone?" she whispered to him as she held the tip against her left cheek and turned her head so her entire left cheek, her lips and nose grazed the sides of him as she turned her head slowly back and forth. He groaned, unable to intelligently respond. He wasn't evasive. He was powerless to react.

They were in the car for several hours; talking about their uncertain futures as she kissed and rubbed him. She did not want to get pregnant. The young boy was in too much ecstasy to care how he was getting it. This was better than any regular fuck he had ever been a part of.

Jenny finally got the courage to put her lips over the tip. Rather than bob up and down on him, she used it to steady him as she caressed his shaft with her delicate fingers. She used her tongue to flutter across the tip while he was talking. Eventually he erupted. Jenny was too green about these things to know quite what to do. Until Nkwame's departure after the NFL draft evening study sessions at the library always ended with mutually satisfying oral sex. Jenny fondly remembered the joy of learning what signs to look for to keep Nkwame's cum from getting all over her.

Attending college on a track scholarship she dated almost every discreet black team member from spring semester of her freshman through the end of her senior year. Four years of developing her innate sensuality enabled sexual gratification to steadily evolve from oral sex to lasciviously sheathing their magnificent black cocks with Magnum condoms to become friends with benefits. Wistfully Jenny recalled how liberal, open-minded collegiate classmates, faculty and coaches accepted her interracial associations.

Graduating college meant leaving interracial sexual pleasure behind her. For twenty-five years since returning home to Kansas Jenny kept her experience with black lovers secret. Well aware of how conservative and biased Jayhawks are and having married one, she was unprepared for this unforeseen opportunity. Even without a clue about her collegiate sexual proclivities Joe can neither think his wife can possibly avoid forsaking their marriage vows while undercover with black men nor claim ignorance of the old adage, "Once a woman goes black, she will always go back."

After carefully considering all her options over a sleepless night, a singularly focused Friday, and a very nervous Saturday morning she finally realized her long suppressed sexual preference would be a tremendous asset while on this undercover assignment. Winning Sam Cromwell's trust and confidence undoubtedly meant showing no reticence for sex. Jenny concluded the persona of an entirely different woman while undercover has to be the complete opposite of the faithfully married mother of two for the past twenty-five years. Absent any fear of pregnancy like with her black fuck buddies in college, Jenny wanted to enjoy as many black men fucking her bareback as often as possible for at least as long as it takes to close Joe's case, and most likely long after.

Saturday evening, Jenny took the car of the woman she was to pretend to be. Since both of their names were Jenny, her daughters didn't need to know much. They would call her "Mom" anyway.

She had gone over to Marie's house. They had agreed to meet there. Jenny had left home wearing her usual matronly dress that went to the floor with a large bag that fit over her shoulder. When she went into her daughter's house, Ginny and Marie were sitting at the raised kitchen counter on bar stools having a couple of drinks. They were having a good time until they saw what their mother was wearing.

Before she could discuss her plan to borrow more appropriate clothing Marie blurted, "Come on, Mom, we're going out to the Garment District. They will all be young couples. You will look out of place." Ginny returned from Marie's bedroom with a bundle of clothes in her arms.

"Take off those clodhoppers and try these shoes on" she said as she handed her mother a pair of dark boots. They were suede and zipped up the sides to just below her knees. The boots didn't show under the long dress.

"Take that dress off Mom." Ginny said as she tossed her a dark silk button front dress. Jenny pulled her dress off over her head and started to put the other one on.

"Oh, God, no Mom, you can't just throw another dress on. Your bra straps are going to show. Take off the bra. You can't have those straps showing on a dress like this.

Jenny unbuttoned the top half of the new dress she had just put on. She lowered her head so she could reach around for the clasp. The nude colored fabric didn't hide melon sized 38C breasts with no sag to them after having two children. Her daughters marveled at their mother's build and at forty-eight she didn't need the bra. Her long-stemmed coral nipples defied gravity as they stuck out enticingly from her alabaster white breasts.

Initially Jenny was embarrassed by nudity in front of her daughters. She smoothed her hands down the sensual feeling silky dress and tentatively asked, "How does it look?" Her persona began transforming from Jenny Jenkins to Jenny Munson as a glance in the mirror revealed how provocatively the dress showed off her nipples.

"Well first of all, your panty line shows. You need to take off those Mother Hubbard granny panties" the girls both said and then giggled. They couldn't believe they had gotten their mother to go without a bra and were stretching their luck with the panty command.

Jenny turned in the mirror. Yes, she could see the panty line at the top and bottom. She looked at her daughters. They did not have panty lines. She did not realize they were wearing thongs, and figured if they could do it so could she.

Jenny Jenkins would have been apprehensive about her daughter's dress only reaching down to the middle of her thighs. It would pass the catholic school test of being within the edge of her fingertips. So unbeknown to her two children Jenny Munson's persona easily acquiesced to their urging and chiding.

They walked out and got into Ginny's four-wheel Wrangler. It was summer and her husband had taken the doors and top off of it. Ginny drove and Marie sat in the back. It was not easy for Jenny to get into the high four-wheeler with high heels and a short skirt. It was even more awkward because she knew she had no panties.

The drive from Ginny's nice house to the Garment District was short, but there were lots of stop lights. Jenny had to keep her small clutch purse over the hem of her dress because of the wind. No matter what she did, the wind seemed to flutter the too short dress up enough that other drivers could see quite a ways up her thighs. Jenny Jenkins was embarrassed, but Jenny Munson kept telling herself these were strangers who she did not know and would never see again. Both personas enjoyed a twinge of sensual excitement over repeatedly seeing proof this forty-eight year old MILF could still turn heads.

When they got to Guinevere's Jenny was behind her two daughters as they entered. Even though there was a good twenty four-year age difference between them the three women could have passed for triplets. They all had very long reddish brown hair, freckles and a mind-bending tan for redheads. Their identical Dolce and Cabana sunglasses pretty much sealed the deal.

Jenny momentarily caught her breath when she spotted Sam Cromwell. She recognized him from both newspapers and case file photos. He was sitting near the middle of the room with several other men in business suits. He was much taller, even seated, than the pictures indicated. He had retired from the local NFL team because of repeating knee surgeries ... He looked like he could still play.

The hostess seated them at a table for four up against the full height glass window wall facing the street. The whole room full of diners had quieted when the three women walked in. Their identical fashionable sunglasses seemed to set them apart. It was like sitting in a strip joint with twenty nearly naked dancers walking around. Yet everybody fixes their attention on the one good-looking clothed girl that comes in with a date.

Jenny and her daughters ordered drinks; then the food; and then desert. Sam was watching but it didn't seem like there was any diplomatic way for one group to approach the other. Jenny knew she had been charged with introducing herself by her husband. A lot was riding on this evening.

After the three women seemed to have been lost by the waitress and could not get another round of drinks, Jenny got up. She walked across the room just past Sam's table delighted to see he was following her the whole way with his eyes. The sexy redhead seemed oblivious to the stares of most of the men in the room as she went into the bathroom. She checked her makeup while totally morphing into the uninhibited character she had decided upon while undercover. The transformation began while changing clothes and during the ride here and solidified with their first eye contact. Not wanting Sam Cromwell to harbor any doubts about her availability she unbuttoned a couple of buttons both on top and at the hem putting her two best assets on full display. Either in spite of or more likely because of being her vice detective husband's target, getting Sam Cromwell to fuck her before this case closed is intended to make Joe a cuckold.

Exiting the ladies' room with provocatively showing more tits and legs, she strolled nonchalantly to the bar. She raised one leg to get herself up onto the high bar stool. Jenny deftly hoisted herself up on the stool and crossed her legs provocatively allowing the dress to part below the open buttons. Most of her bare legs were now showing.

As a faithful wife of twenty-five years this was a shocking but still marginally tasteful display of skin. If her hair had been bleached blond and frizzed out instead of the natural red and woven into a French braid, she would have looked tacky. If she had worn a short red dress instead of the dark one with a couple of unbuttoned eyelets, she might have looked tacky. Instead of looking like a twenty five dollar hooker, brief eye contact with her quarry assured her of Sam Cromwell's interest in what appeared to be a several thousand dollar a night escort at the bar.

Jenny paid for the drinks; tucked the small clutch purse under one arm and picked up the drinks before pivoting the stool so her knees were pointing directly at Sam Cromwell. When her left leg met the floor, she still had her right leg up on the bar seat rung as she took her time dismounting. For a couple of seconds her thighs were bare high enough that Sam Cromwell and everyone else could see the edge of her tan line before the short dark dress closed like window drapes thus ending the intentional floor show.

Jenny could care less what everybody else saw. She succeeded in provocatively getting the undivided attention of Sam Cromwell. As she walked by his table, she stumbled and spilled some of one of the drinks on him.

"I'm so sorry sir. These floor tiles are a little uneven and I caught my heel on the edge of one of them." She said winning an Oscar for the on cue flow of tears. Leaning forward during the entire incident presented him with an unimpeded view of her proudly displayed white 38Cs. Besides communicating her availability Jenny implicitly conveyed absolutely no reservations with this handsome black man fucking her.

"That's O.K. miss. It'll clean up." He quietly replied. She could see in his eyes that her come-on was successful. Pretending to be embarrassed, Jenny made her way back to her table and succeeded in distracting her daughters with their long overdue the drinks.

She took out one of Jenny Marie Munson, Librarian business cards and wrote her cell phone number on it. She got back up and walked over to the group who appeared to be ready to leave. "Please take the clothes to any dry cleaner's. I will pay for their cleaning and bring them back to your office." She said as she handed him the card.

Sam looked at it. "Thanks. Miss Munson. I will text you my address. If you are nice enough to bring it to my office, I will pay you back by bringing you back here for dinner. Thanks for the card. I will keep it." He said as they left.

By the time Jenny returned and sat down, her phone beeped. "My name is Sam Cromwell. My address is and phone numbers are..." and he had all the information to return the clothes.

It was late by the time Jenny picked up her car at Ginny's and drove to Jenny Munson's former home. She pulled into the garage, quietly exited into the rear alley and into her own car. Halfway home her phone beeped again but she couldn't be distracted in the unusually heavy traffic.

Jenny had forgotten to change back into her original wardrobe before she got home. "Wow! You look fucking fantastic." Joe said with his eyes popped out like gold fish.

Jenny opened her cell phone and laid it in front of him with only the first text message already opened.

Joe's only reaction was, "Good fucking job, honey!" Belatedly wrapping his arm around her without any affection would have been irritating if not for the anticipation of reading the second undisclosed text message from Sam Cromwell. Jenny avoided her husband by busying herself in the kitchen until Joe went up to bed.

Jenny was unsure of what to expect with Sam Cromwell's second text message. Taking a deep breath she fingered through the menu saving the first text message before bringing up the second text message with an attached picture of Sam. "It is an unparalleled privilege to meet such a gorgeous woman this evening. Please do me the honor of attending dinner theater with me on the evening you return the suit from the cleaners. Sam."

Jenny texted her response, "Sam you honor me with your invitation. I gladly accept." Sam's picture was saved into the cell phone's "my file" before confirming removal of the message text. She didn't dare retain such a romantic text message from her husband's nemesis. Receiving that very enticing offer eliminated all remaining reluctance with being manipulated into an undercover assignment.

Every interaction thus far with Sam Cromwell reinforced the old adage, "Once a woman goes black, she will always go back." Four years of exclusive interracial dating had successfully imprinted the correlation between sexual pleasure and black men into Jenny's psyche. During the following week she often found herself unaccountably aroused. Whenever she felt the sexual edginess she would retreat to privacy so she could open her cell phone my file and fantasize about the black man in the picture fucking her while she temporarily took the edge off.

Several days went by before she got another text from the Dry Cleaners. "Mr. Cromwell's suit is ready to be picked up today any time after noon." Jenny forwarded the text to Sam and added: "I can have the suit at your place anytime you want. I can have dinner anytime you want."

The text came back: If you get here at four O'clock, I can take you on a tour of our office and we can find someplace nice; better than Guinevere's, on one condition. If you wear the same lovely clothes, I will be your slave for life."

Jenny smiled at the ending. She had actually made contact. Her husband was still gone, and she would have to leave before he got back. She was on her own.

Jenny picked up the clothes. It was an expensive dry cleaning bill, but she put it on the credit card that had been given to her as part of her new identity. She drove the Wrangler to Sam's office. It was in the river bottoms. Lots of the old office buildings, warehouses and train loading docks had been rehabbed into contemporary office buildings.

Sam's office was in an old warehouse. It was several stories high. Several of the inner bays had been removed. Instead of a brick building with fourteen feet of head room and huge wooden columns every twenty four feet, the middle fifty feet was a clearstory up to the roof. The offices around the atrium had walkways and doors into individual offices. There was a central receptionist at the main entrance. When Jenny announced herself, she was told where his office was.

The elevator was a glass enclosed cab with a nice view of the entire clearstory. There were lots of flowered and hanging vine plants along the handrails at the edge of the atrium.

Jenny opened the door to Sam's office and walked in. There was another secretary, reception area, private office, large meeting room and a private unisex toilet. The secretary took the dry cleaning and hung it in the coat closet. Jenny stood and shook hands with him as he came out of his office.

"How was your work today?" Sam asked as he offered her a seat in the Mies Van Der Rohe chair. The short dress was O.K. in a dining room chair, but the Swedish seat was very deep from front to back and only about a foot off of the floor. The cold white leather was very comfortable.

"Oh just another day at the office" she smiled and giggled nervously. They talked for a while before Sam guided her up out of her seat. He seemed even bigger now that she was near him than he previously appeared.

Sam had his arm around her back to steady her as the elevator descended. It is awkward going down the elevator the first time when you can see outside. Her high heel boots were not the steadiest support on an elevator moving down. He had pulled her comfortably close to him on the way down. She had no reservations about putting her arm around his waist for more support as they descended. In her Jenny Marie Jenkins persona it would have been very awkward for her suggesting too much closeness too soon. However, in her Jenny Munson undercover persona she did not hesitate to enticingly plant her unfettered booby into her black paramour's side.

It was hot and Sam took off his coat and tie. He walked over to the red 1966 Carroll Shelby Cobra that was parked crosswise in three stalls at the corner of a parking lot that was half full. He opened the passenger door to help her in. For a very brief moment Jenny was embarrassed at her position. The aluminum racing seats had just a little padding and seemed just inches off the floor.

Jenny demurely tried to sit almost sideways to keep her dress together. Sam kneeled down on the parking lot in his $200.00 slacks. He pulled the shoulder straps together and snapped the clasp shut. He pulled the lap belt across her waist and snapped it shut and pulled it snug. He reached under the seat and pulled out the last belt that fit between her legs and into the clasp on the lap belt. It wouldn't fit with her dress the way it was.

Sam looked into her eyes as he started to unbutton her dress. Since it was pretty short already, there weren't a lot of buttons to open to get the belt to snap. Even so, Jenny unabashedly left herself exposed almost to her crotch. Jenny seized the unexpected yet fortuitous opportunity to provocatively reveal her sexy body to her very desirable black date. She sat there with her thin top squeezed down against her body leaving her proud nipples straining to explode through her dress. There was no hiding what was and was not beneath the garment.

Sam got in and started the engine. It didn't have any mufflers. There were a series of baffles at the end of the four tail pipes. It wasn't unreasonably loud, but had the low clear rumble that sounded like a Harley that had been race tuned. It would hardly run at idle, but ran effortlessly at about 140 mph.

They took the long way through town back to the local dinner theatre. The theatre was noted for having celebrities from Hollywood and New York being the main characters in plays and musicals. Sam had box seats along the side. After the dinner was over, the table was pushed to one side and Sam sat next to Jenny. The program that night was a musical. It was a "play" about the "Buddy Holly Story." There was some beautiful music and Jenny lost herself in it. Not daring to text or call her husband for fear of exposing either of them for what they were doing effectively dismissed any Jenny Jenkins worries about what her husband might be thinking.

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