Dealing With Jessie - Cover

Dealing With Jessie

Copyright© 2019 by Jedd Clampett

Chapter 1

Romantic Sex Story: Chapter 1 - This is the story of a very ill woman.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Fiction   Cheating   Cuckold   Oral Sex   Safe Sex  

It was a Friday night in early December, and a big gala had been arranged for a retiring state delegate. Held in a downtown hall; hundreds of people were there.

Prologue: Jessie sat nervously on the edge of the big desk in the ‘President’s Meeting Room’ of Patriot’s Hall, a splendid if somewhat staid facility in the center of the city. She was expecting someone; a colleague she despised named Jeffrey Snyder. Somehow Snyder had managed to finagle an inside track regarding the two new partnerships their law firm was considering. She just had to get one of those partnerships. She just had to.

The door opened, and in walked Snyder. As usual he was dressed in one of the most expensive suits money could buy. She expected, like most chiselers, complaining of a poor fit he’d take the suit back Monday after the gala.

With a poorly-concealed snarl Snyder said, “So, the lady waits!”

Jessie waved him an artificial smile, “As agreed, I’m here.”

Hands outspread her adversary approached, “Let me see, lovely lady.”

Jessie reached behind and undid her dress, “I have your assurances my name will head the list, and whatever happens here stays here?”

He smirked, “Of course.”

Panties and hose already in a heap on the floor she pulled her dress from her shoulders, and unfastened her brassiere to reveal small but well-shaped breasts.

Pants undone, tumescent penis in his left hand Snyder stepped between her legs. He pushed her dress to her waist and proceeded to invade her fleshy crease, a crease that heretofore had been the exclusive province of her unsuspecting, and trusting husband.

Snyder moved quickly. His thick but somewhat short penis penetrated her dry canyon; and after several strokes of rough in and out he spent. Stepping back and reaching down, he grabbed her panties from the floor and finished ejaculating. Wiping his rapidly dying member with her now savaged silken treasure he chuckled, “I’ll put in a word, but remember, you must do your part or they won’t oblige.”

Jessie cringed, “I’ll remember.”

Pants back together, fly tightened, Jessie’s panties still clutched in his hand; Snyder retreated the way he came. “Have a pleasant rest of the evening,” he snidely chortled.

Jessie hiccoughed; then coughed, then sniffed back a sob. This was her first betrayal, but not to be her last. Her husband, the man she cared for more than her own life didn’t know it, but his world was about to change in a most horrible way. She hated herself. She hated Snyder. She hated the older partners. Her husband would never understand. It didn’t matter; she had to have that partnership!

And now we begin:

Gary was a middle school math teacher; his wife was a lawyer at a large downtown firm. She’d been chasing the “Holy Grail”, a full partnership for some time, and she thought she was finally on the short list. Gary hoped she was, he hoped she got it; he and their three daughters had suffered through every twist and turn of the process. Being a teacher and department head he knew there was always a certain amount of chicanery in every bureaucracy, but his wife’s firm was large and the opportunities for mischief enormous.

This evening’s “big do” had seen his wife meandering from table to table glad handing and back slapping with politicians, other legal minds, and various shakers and movers with relentless zeal. She was always looking for that next leg up, and he’d been proud of her determination. Twice tonight she’d disappeared; he assumed to participate in private meetings trying to garner more support for her cause. They all did it.

What had any of that to do with their marriage? Gary was in one of the bathrooms upstairs emptying his bladder when one of Jessie’s coworkers, Gary’s wife’s name was Jessie for Jessamine, slipped in. The man’s face was red like he’d been working out; he wielded a smile as broad as the Everglades. In his hand he clutched a pair of very expensive looking women’s panties, the kind not sold at Victoria’s Secret but at places like Nordstrom’s. He waved the filmy article about like it was a trophy of war, and as everyone all quickly found out, it was exactly that.

His countenance glowed as he whispered loudly, “I got her!”

Gary and the other three in the bathroom had no idea who he was talking about but another man, one Gary recognized as one of Jessie’s colleagues muttered, “No kidding.”

The first delinquent, the man with the panties held them up and proclaimed, “I got her in one of the offices down the hall. She was there, waiting and ready. I backed her over a table, lifted that thin black dress up around her waist, rolled down her pantyhose, slipped off her panties, and pulled the old in and out right there on the table. Did it for ten minutes too! Man she was tight. I got in deep. I shot right in her crotch. Let me tell you she liked it.”

The third gentleman, another lawyer, ogled the panties and said, “Let me have a look?”

Another asked, “What’d she look like?

The owner of the panties smirked and replied, “Man she looked great. Not shaved, but trimmed to perfection, as pink as I’ve ever seen. God what a crease, the narrowest wettest damn slit ever. And that ass; Jesus, for a woman her age! I tell you she’s something to die for.”

The third guy said, “Good huh.”

The first replied, “You’ve got to be kidding; she was all round, firm, and red. I tell you she was so hot. Her hands were all over me.”

The third man said, “She was good. She suck you off?”

The panty owner was a big man, maybe six foot four, youngish, around thirty-five. Gary had his name on the tip of his tongue, Jeff something, Jeff Snyder. He remembered, he’d seen him a couple times at company functions. Jessie knew him, said he was a creep.

What’d he say? Gary had missed something. The guy, Jeff Snyder, kept twirling those panties around on his finger. He said, “She wanted to. She even started to go down on me, but I wanted her twat so I got her on that table and fucked her. I fucked her good! I tell you man.”

He handed the panties over to the second man. That was when Gary recognized who they belonged to, they belonged to his wife! She’d bought them that afternoon and showed them off earlier that very evening just before she put them on, just before they did it.

Gary realized none of the men in the bathroom recognized him, or if they did they didn’t care. They were too interested in the first man’s prize.

The second guy asked, “What’re you going to do with them?”

The owner, it had to be Snyder, replied, “Don’t know. Can’t keep them, my fiancé might find them.”

The second man said, “Give them to me.”

The third said, “No, I want them.”

That’s when Gary jumped in, “I’ll buy them.” If they were his wife’s he needed to keep them out of circulation. He knew the kind of people Jessie worked with, if one of the men got her panties there might be all kinds of shenanigans. Plus, they were his wife’s. He’d need them for later.

The first man replied, “Yeah? How much?”

Before Gary could answer one of the others said, “I’ll give you Fifty dollars.”

Gary had no idea his wife’s drawers might be worth that much, but he suspected how they might be used. He was wearing a very expensive watch, not a Rolex, but a costly piece of jewelry his wife bought him that fall. He pulled it off his wrist, “How about this?”

The proud owner of the “silk” grabbed the watch and thrust the panties in Gary’s hand, “You got it,” he said.

The second man asked, “What are you going to do with them?”

Gary realized they really didn’t know who he was. He said, “I have a hunch these belong to Jessamine McGowan. Am I right?”

The first man nodded and said, “Boy you’re on the ball.”

Gary replied, “I don’t know what I’ll do with them. I do know she’s hot for that partnership opening up.” Holding up the panties he added, “Who knows? They might come in handy someday. She’s married you know.”

The third guy said, “Yeah, a school teacher or something.”

The second nodded.

The guy he knew was Snyder grinned and said, “Yeah, what a waste, piece of tail like that pissed away on a school boy.”

They all laughed.

It was then another, unknown person came in, and their little gathering broke up. Gary went to one of the private stalls, got some toilet paper, wrapped his new treasure up, and stuffed them in a coat pocket. Five minutes later he was back out on the dance floor wandering about nonchalantly looking for his wife. He kept thinking, that fucking whore. What a piece of shit she turned out to be. She fucks me before the big shindig and fucks a fellow lawyer later while I’m downstairs like some stupid asshole.

He couldn’t find her. She wasn’t at their table, and he didn’t see her on the dance floor. It kept going through his mind, who else is she fucking? Maybe she was pulling a train. Maybe she’d lined up some of the senior partners? He wanted to kill her. It really pissed him off. But what could he do? They had three kids, three teenaged girls. He felt lost out on the dance floor. He felt like everybody knew what his wife was doing. He felt like they all knew what he had in his pocket. He had to get away.

He found his way to the front door, went outside, and drifted over to some shrubbery and vomited. He walked a little further out, and sat down on the curb. The concrete was cold and damp, but anything was better than going back inside. How the fuck was he going to get through the rest of the night? How was he going to handle this with Jessie? If it was just him he knew what he’d do; he’d take her home, drop her at the front door, and leave her. But God damn! He had three girls!

He pulled the panties out of his coat pocket, they definitely were hers. He sat there on the cold damp cement holding them in his hand. A few hours ago he’d watched her put them on. A few hours later a shithead lawyer pulled them off and fucked her. Never a violent man, he felt violent now.


Jessie despised the philandering Jeffrey Snyder, but she knew the son-of-a-bitch was after the same thing she was, a partnership. The problem was Snyder had the inside track; he had something, she didn’t know what, but she knew he had at least one of the senior partners over some kind of a barrel. She figured if she could find out what Snyder had she could use it, a quid pro quo as it were. Her bad luck, the prick had managed to turn the tables on her. He knew she was ashamed of her husband. Somehow he used that to finagle a stupid bet, a bet that she now had to make good, giving Snyder a little sex was just a part of it, the rest would come later.

God, she loved her husband; he’d always been there for her, he was the best. He was smart, the smartest man she knew. He was sure good to her, good with their three girls, good in bed, and good to her parents, but he had no ambition. Poor Gary could be anything, but no, not him, he was just another “do gooder”, a candy assed school teacher, at a public school no less, not even a high school, a middle school!

That bastard Snyder had come inside her, something she hadn’t wanted. She wasn’t worried though; she had her ‘morning after pill’. Still, she felt cheap. She’d never done anything like this before. No, not her, until tonight she’d been Mrs. Faithful. She just had to get that partnership!

Jessie, Mrs. Gary McGowan was inside the hall trying to find her husband. She asked her personal secretary, a youngish woman named Gail Honeycutt if she’d seen her husband, but she’d said no. She walked all about; she checked the bar, the lounge, the dining area, no Gary anywhere. He had to be around somewhere!


Jessie, Jessamine, his wife, mother of his kids, was now the corporate whore. Shit, twenty years, eighteen married. What a waste. He sat there on that cold concrete curb and thought back. They’d met while he was in his junior year at one of the state’s better public universities. She was approaching high school graduation working part-time, thanks to her mother’s influence, at the local public library. She was pretty and got hit on a lot. He recalled how he played his cards pretty close to the vest. She was irritable and indifferent at first; it took him quite a while to get beyond her defenses, but once he did she proved to be one of the most delightful ladies he’d ever met.

Jessie was pretty, with blond hair she kept in a tight bun, fitting for a young lawyer. She was tall, maybe 5’6”, sky blue eyes; not real sexy, a little on the thin side, smallish breasts, but she’d always been, for the most part, a real sweet kid.

He recalled how they dated through his junior almost to his senior year, but over that summer a little something came up. That little something was a baby, Dorothy. Jessie said she was on the pill, but he guessed not. Back then money was tight. He was the only child of a poorly educated single mom. Jessie’s parents were well fixed, but that didn’t do him any good.

Gary hadn’t wanted to get married, at least not back then, and not to Jessie. He loved her, but to him she just wasn’t marriage material. When they first met he thought she’d been sweet, maybe a little irritable; but the sex had been so good he thought he could put up with an occasional tantrum. The problem was her tantrums were more like category five hurricanes. If something went wrong she could really go off. She even smashed his windshield once, used an aluminum bat to do it; said she was trying to get at him. That was what led him to suggest they see other people. At first she panicked, even cried. Then she said she was good with the idea. Things went along for a while, like a couple months, and then she dropped the bomb, she was pregnant.

He had been just barely getting by. His mom worked at a Walmart and was struggling. He worked two part-time jobs to help his mother and to pay the costs of college. He was caught in a trap; his father, whoever he was, had skipped out when his mom got pregnant. Even though Jessie’s parents had money, he knew he could never run out on her.

That first year had been awful. Jessie’s parents never said anything, but he knew they blamed him for her pregnancy. No one wanted an abortion so her parents took them in. He still worked at a Fed. Ex. washing trucks at night, but her parents paid for his college. They even picked up all the medical bills.

The very next year, their second, Melanie came along, and two years later Katherine showed up. After that, with three girls, he and Jessie got exponentially more careful.

Meanwhile Gary got a job teaching math at one of the local public schools. He started at a middle school, decided he loved it, and had been there ever since.

Jessie had always wanted to go to college, and after Katherine came she was more determined than ever. Her mom and Gary’s mom covered the daytime babysitting so Jessie could go to college. Gary taught during the day, and took care of the kids most nights when he wasn’t working.

Money was tight, but Jessie was smart and a hard worker. She finished undergrad in three years, and went straight to law school. Two years later she took and passed the bar; then she got herself an entry level lawyering job at the downtown firm where she still worked.

They worked hard; they scrimped and saved, and managed, with her parent’s help, to put aside enough money for a down payment on an older mid-sized house, a split foyer in a 1960’s era neighborhood. Jessie’s success at law school, and her subsequent new position put her on track for some good money. Gary quit the night work, and started to spend more time, including summers, with the girls. As the years rolled by Jessie’s legal work took up more and more time so Gary picked up most of the domestic chores including the cleaning, laundry, and meals. Several years on, what with the recession and resultant suppressed teacher salaries, and Jessie’s hard work she was pulling down almost twice what Gary was earning so he took up all the remaining home responsibilities, and that included getting the kids off to school, the ironing, and all the other duties that needed to be done.

For Jessie her work was never done: it seemed like the more she succeeded and the harder she worked, the more ambitious she became. Three daughters, plus Jessie’s growing ego, meant finding a bigger house, exclusive private schools, clothes galore, an in-ground backyard pool, lavish vacations, more and more frequent travel for Jessie, and lately a new car for Dorothy. It worked out great for Gary, or until recently he thought so, Jessie was pulling down so much money his income landed on the back burner; Jessie picked out the new house and worked out the mortgage, she chose the schools and paid the bills, and of course the clothes and cars all fell to her too.

Meanwhile, his salary only covered insurances, groceries, utilities, and the occasional toy for dad and the girls, like a small sailboat, hunting rifles and shotguns, a pram, and a nice safe, and slow, motor boat. For sure, he wasn’t a loafer, with his math background he understood a little about finance, and started quietly setting aside money in mutual funds in just his name. He wasn’t hiding anything; he just believed he should have a little something that was his alone.

Jessie’s success also left him the job, not a job really, of seeing to the girl’s social life. That meant dance, swimming, and Karate lessons, as well as drama and sports activities. He had to admit it wasn’t hard being the dad who got to go to the dance competitions, swim meets, hockey, volleyball, soccer, and baseball games, not to mention caddying girls around for sleep overs, parties, and field trips. He was Mr. Mom, and loved every minute of it!

So much for the back story, that left Gary with an attractive over-achieving, and now adulterous wife, three wonderful daughters, all the spitting image of their mom, and yes himself, a moderately well-paid teacher, financially alert if not overly smart, a modern house mom, and to some, maybe a near-do-well, wife dependent, lazy loafer, it was all a matter of perspective.

To be a little more explicit about the money; he paid Social Security all year, but Jessie’s “freedom threshold” has been repeatedly pushed back, from once New Year’s like his, to Thanksgiving, then Labor Day, next back to Flag Day, and most recently, he suspected back as far as Mother’s Day. He was never sure as she kept her income and expenses to herself. He wasn’t sure, but he believed they were rolling in the gravy!

Well there it was, he came back and took his place at their table. He still had his wife’s panties stuffed in his coat pocket. It was a flat out fact he had to do something. He’d heard some war stories where men, and just as often women, knew their spouse had been cheating but either pretended it wasn’t happening and did nothing, or they came up with some elaborate scheme involving electronic surveillance or secret agents working night and day to catch the schemer outright. Gary was neither a hider nor a schemer, but he knew he had to do something, he just wasn’t sure what.

He asked the person next to him what time it was; they said nearly 11:30, almost time to go home. Jessie had decided that, since Dorothy was seventeen, soon to be eighteen, the girls didn’t need a babysitter, but tomorrow was Saturday and he had his chores, things like the vacuuming and laundry. Besides neither wanted to stay too late, it was December, Christmas season, they had the house to decorate and a tree to put up. The girls and he had gone to the tree farm and cut their tree a week ago, and he figured either tomorrow night or Sunday they’d put it up and decorate.

Yes, though Jessie said she didn’t care, they still bought a live tree; the girls still wanted it that way. Gary liked a live tree. They had a cat, a grey tabby named Jupiter who was eight, and a nine year old chocolate lab named Daisy. They were both good with the trees, but anyone who owned a lab knew that with their tails, anything could happen. Jessie wasn’t very fond of Daisy, she said she preferred a smaller dog.

He saw Jessie cross the dance floor; she looked peeved, and her makeup didn’t look quite right. He hadn’t decided anything yet. What was he going to do? Well nothing at the big party, certainly nothing in front of girls when they got home, but he wasn’t going to hide his head in the sand. He decided he’d have to bring the issue up on the way home.

Jessie sat down at the table. She was pissed that she hadn’t been able to find her husband. “Where have you been,” she asked? “I’ve been looking all over for you. You had me worried.”

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