Two MILF’s for Valentine’s Day

Copyright 2014

This contains material of a sexual nature not suitable for anyone under 18.

Editing contribution by Literotica member Private1stClass vastly improving my story. Thanks!

This is a 2014 Valentine's Day Contest Entry.

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Lou's boss, Frank, was so boring. Pretending to give Frank his complete attention, Lou daydreamed. Fantasizing about women occupied his mind. He had worked long hours and traveled too much over the last months. Except for one notable exception, his love life had been dull. Then, as his boss droned on about their business, a beautiful woman walked into the bar area and he thought, Maybe it's time to change my luck.

It was Lou's second year with the investment bank and his second annual early February "Results" luncheon. He knew the routine. In morning meetings with each team member, his boss reviewed their past fiscal year performance, set goals for the next year, and passed out the bonus checks. For drinks, lunch, and bullshit, Frank hosted their team at a fancy restaurant. The lunch announced business was over and now it was time to celebrate. Lou knew that he should stick with his usual two drinks and forego the hangover he had last after last year's "Results" lunch.

It had been a very successful year for Lou. Recruited by this investment bank for their real estate lending department, his large Christmas bonus reflected his achievements. Lou found that he had an uncanny ability to parse financial numbers and penetrate the bullshit of real estate developers. He could pick the winners from the losers—at least most of the time. Assigned to cure several sick loans, he had gotten the projects back on track and saved the bank millions of dollars in losses had the loans gone into foreclosure. Although he was the junior member of the team, just two years out of college, he was accepted and esteemed as a big contributor to the department's success.

They started their lunch at the bar in a boutique hotel restaurant. Lou was surprised that all 15 or 20 bar seats were empty when he arrived. The dining room had plenty of empty tables and the hostess said she would save them a table. The guys in his department gathered at the entrance to the bar nearest the hostess station and the bar entrance. A chest-high partition separated a very narrow corridor of bar and bar stools from the dining area. Several, like Lou, sat in bar stools backs to the bar and the others clustered in the aisle way in front of the partition. Deep in conversation, they effectively blocked access to the rest of the bar.

A blonde woman—Lou guessed she was 30 to 35 and very attractive—had to squeeze through them at the end of the bar to walk to the other end. As individuals and as pairs, his group moved about to permit her to move through them. It was still a very narrow and congested path. As the blonde navigated their gauntlet, Lou smiled at her and she returned his smile. Wow, Lou thought, she's really good looking. Soon, one, then two, good-looking women between 30 and 50 had to thread through their group of happy, animated men to join the group of women at the other end of the bar. Within 20 minutes, there were about 20 women clustered at the opposite end of the bar.

Some of the women were tall, a few were petite, many were busty, and all were attractive. There were redheads, brunettes, and blondes. Some were their natural hair color and some obviously not. All were elegantly dressed, some in high-heel boots and others in high-heel shoes with dark stockings. The women were not perfect in all respects; yet, their beauty and assets made their imperfections meaningless. All his co-workers noticed them. They eyed all the women as they passed through and exchanged nods and smiles indicating their approval.

His boss, Frank, was a womanizer and Lou glimpsed him copping a feel of a blonde woman's butt, as she traversed his bunch to join the other women. She wore a tight knit red dress that displayed the curves of her hips and ass as well as emphasizing her ample breasts. She didn't appear startled but did turn to see who had stroked her ass. She looked right at Lou, giving him a smile that seemed to convey only one possible interpretation. It seemed to tell him,that grope was nice, though it's a little naughty, isn't it?--And Lou believed she was signaling she liked the naughty part. Although his hand was not the guilty one, he warmly smiled back.

A bourbon on an empty stomach loosened Lou's usual restraints on his behavior and he couldn't resist staring at the women. He twisted on his bar stool and kept appraising each one. Two women especially attracted his attention. One was the red dress woman. The other was the very first one who had navigated through his office mates.Red dress and mystery woman, Lou identified them in his mind. The red dress lady placed a birdcage veil with a large red heart and little red hearts in the veil on the mystery woman, apparently signifying she was the guest of honor or something for the upcoming Valentine's Day. Lou thought she was gorgeous.

This mystery woman was about 5'5" or so. Her bleached blonde hair, Lou conjectured, was not her natural color. Short and wavy, it was a very becoming cut and style. Her skirt was above her knees and she wore dark hose and three-inch high-heels. She was curvy and her sweater displayed a fine set of large grapefruit sized breasts. Her waist was modest, yet a slight thickening showed she wasn't a young, trim thing anymore. That didn't matter to Lou; he thought that she was gorgeous. He estimated her age at 30 to 35.

Lou traveled a lot for work and all his romances over the past two years had been brief flings. He was dissatisfied with his love life. Maybe just being terribly horny and lonely made him stare at the woman.

As the group of women grew with new arrivals, they stretched out along the entire bar. As the women encroached into Lou's group, he jostled this mystery woman at one point with his elbow.

"I'm sorry," he apologized. She explained that every year at this luncheon somebody was randomly chosen to be the Valentine's Day guest of honor.

She laughed, "And butt of all the jokes and gag gifts, too!"

Lou bit his lips not to retort,your ass does looks wonderful and I'd like to caress it.

Instead, he smiled and replied, "You look wonderful in the veil and I hope you have a very happy Valentine's Day."

Lou didn't hear her response clearly; he guessed her answer was not an optimistic one. When his team sat down to lunch, he sat directly facing a long table where the women were eating lunch. There, just one table away, Ms. mystery woman sat at the end closest to Lou. Next to her was the red dress lady.

By now, Ms. mystery woman was aware that Lou was giving her appreciative glances. After drinking another glass of wine before lunch arrived, Lou couldn't stop eyeing her. As he ate, he gazed across the table at her. She noticed him watching her but didn't frown or grimace. Every time she caught him staring, she gave him a nervous smile. Soon, she returned his looks with a more inquiring expression.

Lou's boss noticed he was distracted and demanded that he get back involved with what Lou knew was total bullshit. The mystery woman left the table for what he supposed was a potty stop. Lou fumbled in his pocket and found his business card. He scribbled on the back: "I apologize for staring. You are very beautiful and I would like to meet you." On the printed side, he underlined and circled his cell phone number. Rushing from the table, he intercepted his mystery lady as she returned down the corridor from the restrooms.

He gave her his card and grinning said, "I just couldn't stop admiring your beauty. Please accept my apology for staring."

She took his card, intently studying his scribbled message. Turning it over, she looked at his face and considered him. She read the printed side aloud. "Louis B. Shipton, Senior Analyst for Real Estate Investment." With a shy smile, she murmured, "I noticed you, too."

She brushed by him and returned to her table. By then Lou's group was gathering in the lobby and leaving the restaurant. He gave one last glance at his mystery woman. She was showing the red dress woman what he assumed was his business card with its scribbled message and whispering in her ear. They both turned toward him. He could imagine his mystery woman telling the red dress, "That's him."

Joan, Lou's mystery woman, and in the red dress her best friend, Sally, had noticed Lou even before he had given his card and note to Joan. While his staring had not been indiscreet or offensive, they detected him eyeing them. The two huddled after the luncheon and discussed what Joan should do. Joan believed Lou's note was an obvious invitation for a date, at the least, not just a phone chat. Sally agreed and told Joan about the unidentified groper who stroked her ass when she passed through the men standing with Lou. She related how she had she turned to learn whose hand had fondled her butt and given Lou her most encouraging smile. When Sally turned, she had discovered that it clearly wasn't Lou's hand. Given Mr. Louis B. Shipton's interest in her friend, she thought if he had been the one fondling her ass, maybe she would have gotten the interesting note.

For Sally, Lou was a hunk. Handsome, well built, and a confident smile gave him magnetism and allure that aroused her. Her biggest disappointment was that Joan attracted him and got his inviting note.

Sally encouraged Joan to respond to Lou's note. She pointed out the obvious: their husbands, partners in an import/export company, traveled most of the time to Asia and Africa. Their children were away in college, and the two were lonely and received little flattery or compliments at home. Sally argued that they were at the sexual prime of their lives and deserved to be flattered, pampered, and fucked. Staying at home with TV, books, and what excitement they could generate using their own hands is what the two mostly did. Although Sally did no more than talk about sex outside their marriages, Sally always voiced much more adventurous ideas about sexual encounters. Joan expected that she would encourage this dalliance.

Joan wondered just who Louis B. Shipton was. She knew she could find out. Joan was a forensic accountant. She examined financial records to discover the reality of payments, deposits, or hidden funds that accounting records may or may not accurately represent. Law enforcement agencies contracted with her to audit financial records for criminal investigations. She had even done small jobs for the FBI and Homeland Security.

On her laptop at home, Joan perused the various databases she used in her forensic accounting and clicked through Google for Louis B. Shipton. Quickly she discovered the basics: two years out of college, majored in Economics and History, Honors graduate, and ran the 400 meters on the college track team. His credit was very good and he wasn't in any of the law enforcement data bases. She found a three-year-old picture of him holding up the first place trophy at the New England Collegiate Championship meet amidst his 1600-meter relay teammates. Joan had spectated at that event last year when her son Terry competed in the 100 meters for U State there.My, my, she mused to herself,a track athlete and competitor at the same meet where my Terry had competed.

As Sally had painfully pointed out, the two were not getting laid. All their sexual satisfaction came from the own, solitary efforts. Talking to Sally, pondering what to do about Lou, and finding such positive things about him got Joan to start rubbing her pussy and tweaking her nipples. She didn't imagine she was very desirable or erotic looking in her old ratty bathrobe.

Closing her eyes, she could imagine herself dolled up and looking hungry to be fucked. That was enough to get her juices flowing and her hips gyrating while she stroked her clit with one hand and piston two fingers of the other in and out of her vagina. Joan concentrated on an image of Lou on top her: thrusting his huge cock into her pussy, shouting his desire for her, and begging for her attention. It was all she needed to reach orgasm. Alone in her empty house, she moaned, cried out, and screamed "Lou, Lou,FUCK ME!"What has gotten into me? This imagined Lou is so much better than my usual sexual daydreams. Afterwards she decided to call Lou that night after dinner and prepared herself for disappointment.

More clear-headed later that same night, Lou agonized over his behavior. Sure, he had wooed women in a bar or at a party—girls he admitted to himself. This was a real woman. She certainly had intrigued him. She probably viewed him as a kid, a young nobody. Supposing that she would never respond to his not so subtle message, Lou picked up a book he had been reading.Damn, he told himself,too much travel and late nights working has made me a lonely, horny guy. I need to get out more and meet some women.

It wasn't like he had gotten laid lately. There was Carrie in Philadelphia. The bank had sent him to fix a failing retail/office complex in downtown there, where the bank's real estate investment fund would suffer a huge loss if the complex went belly-up. He quickly realized that a new and better management company could probably turn the development around. Carrie came with the new management.

Amazingly, he had met Carrie several years before at a track meet. She was a high jumper for another school and he remembered her. Tall and willowy, she had short blonde hair and a very perky personality. They were both surprised to see each other in Philadelphia. Frantic in bed, she pursued him fiercely. Lou loved sucking and nuzzling at her extended and very rigid nipples. But fucking her was always missionary style and over quickly. She immediately fell asleep and smothered him the rest of the night with her cuddling. He wanted more. He dreamed of getting a blowjob and even fucking her in the ass.

Over last fall when he had traveled to Philly several times to oversee the remaking of the development, they had fucked four times. She begged him to visit for New Year's Eve and take her to this 'Great Party'. It was an ambush. Her mom and dad held a huge New Year's Eve Party at their swanky suburban home. Lou met and mingled with her folks, her brothers, and her extended family. Large and boisterous, many were ex-jocks. As a former track athlete of modest talent, he passed the family's inspection. At the party, Carrie confessed she wanted family and children—she wanted them soon. He knew that was not what he wanted with Carrie.

The most incredibly bizarre moment of the whole trip was when Carrie's mom, Susan, waylaid him. Well, he had to admit to himself,she raped me. While searching for a bathroom, he encountered Susan in the hallway and she shoved him into a back bedroom. Susan was taller than Lou and probably weighed as much as he did. With her weight in her very large muskmelon sized 38 DD breasts and hips and ass, she manhandled Lou. He conjectured she could have been a professional woman wrestler with her physique and strength. Equally aroused and shocked at the time, he could now acknowledge,what an experience and I was a willing victim! Or was I just a whore serving her needs? He couldn't decide which.

"I try out all of Carrie's lovers and I think you'll make me very happy," Susan explained as she unbuckled his trousers, tugging them and his boxers off. Giving his prick a quick inspection, she sucked on his cock making him stiff and hard. Presenting the back zipper of her sheath, it was obvious she wanted him to unzip it. Lou complied. Shedding the sheath exposed her large white ass. Its size made her waist and hips appear modest. Turning back to face him, she cupped a handful of tit in each hand.

"These babies just love to be sucked, nibbled, and touched!"

Lou eagerly satisfied her demand. Susan sat on the edge of the bed with her knees up and thighs spread.

"You've got a great smile and beautiful teeth. How about using them to make me smile? Oh, by the way, don't worry about Carrie. She knows I try her out her men and she won't interrupt us. We can't spend the whole night at this. I know ... that's a disappointment for me too."

Her large pussy with its pink glistening lips matched the size of her hips and ass. Lou supposed that with shaving cream and razor, she had carefully sculpted her bush into a small triangular landing strip that rose towards her belly. On each side of her cunt, she had a thin neatly trimmed bushy edge. It gave Lou an easy target for his hands, mouth, and tongue. She didn't seem interested in extended foreplay and Lou skipped kissing her inner thighs and teasing her clit. He dived straight in. At least, Susan was interested in different kinds of sexual acts; her daughter Carrie was neither interested in foreplay nor variety.

The application of his mouth and tongue aided by two fingers thrusting past her pussy lips quickly got Susan oozing sticky juices that covered Lou's face and hand. Her wonderful salty taste and pungent aroma swirled around as he inhaled her scent and swallowed. As he teased her clit with his tongue and stroked with a finger, her clit stiffened into the size and almost the shape of half of a little finger. Such a large woman, he guessed, should have such a magnificent clit. His happy work produced and Susan moaned.

"My GOD! You are good at this, really good!"

She clamped his head between her thighs and screamed in ecstasy. A squirter, her little prick like clit stood at attention while Susan gushed into his mouth and on to his face.

Lou's lust had risen to an intensely painful level. He struggled from out between her thighs and climbed on top of he.

"It's my turn nowBITCH! You had your fun; I'm making youMINE now!"

He mounted her and slammed his cock into her. One, two, three thrusts and he was deep inside. She tilted her pelvis and rocked in time as Lou slammed his hips forward and back.

"Oh ... Oh ... Oh," she screamed, "Fill me! Fuck Me! Show me that you can make plenty of babies!" Lou sensed no need to hold back and prolong the intensity of their lovemaking. She wanted it now. He obliged and blasted a large load of cum and sperm into the mother of his date. When he plunged in deep, she clinched him with what was otherwise a loose pussy and held him. He slumped down on her and pumped load after load into her.

"That was incredible!" she enthused. "You are quite some stud! You must come back for our Valentine's Day Party. Both Carrie and I will want more of you!"

With that she motioned him off her. Lying propped up on her elbows with her thighs spread, her crotch was a creamy, gooey mess. A mixture of his cum and her juices leaked out of her pussy. She gathered a slather of it and offered it to him. With a snigger of self-deceit, Lou supposed it would only be polite to accept a taste and she filled his mouth. After savoring it, he swallowed the mix with a loud gulp.

Smirking, she directed him to the bathroom and advised him to clean up before returning to the party. The bedroom was empty when he returned from washing himself. Carrie welcomed him back to the party with no apparent jealously or questions. She did hug him and purred that she just loved his aroma. Lou was sure that scent was a combination of lusty sweat of sex with her mother, her mother's pussy, and his semen. She asked several times if he liked her mom and paused before continuing about him liking his dad, brothers, and other family members. In his hotel room, Carrie was even more eager to fuck, the same old quick missionary style. She fell asleep and the rest of the night smothered him with restless hugging and grabbing.