Uncomfortable Womanizer

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Ohmigod," she cooed. "Let's take a breather and do that again."

Later while Whitney was in the shower Luis dressed and left without saying goodbye.

He drove home replete and thinking if only all of his brief sexual encounters were that smooth and so delightful.

* * *

Five months after organizing himself to scout for sex some distance from Joliet, Luis reviewed the situation.

Once again he was thinking about the benefits of a long-term and stable relationship with a female.

Life was not all about sex. He found himself looking more and more at guys with their families at restaurants and he took in with emotional reaction the happy sounds of kids enjoying themselves.

Yes it would greatly add to his life to have a new wife in his life with one or two kids, taking the bad with the good that obviously occurs within families and being the family's principal bread-winner. Within a good family structure it would be near-impossible to experience loneliness as he experienced since the start of his marriage break-up.

Luis then realized his ex-wife had brutalized his soul and she had to share the blame for not dealing with the increasing threat to the stability of their marriage.

They both had been jerks he thought mentally kicking his butt.

And yes, the novelty of traveling around to replete himself engaging with a variety of women he'd know only for as little as a couple of hours, had lost its novelty.

Luis sighed and thought not attempting to save his marriage had brought him misery and in engineering a different type of relationship with sex-focused women really had been a pitiful response. It had achieved nothing, leaving him with a new stigma weighing him down.

He admitted it was uncomfortable being a womanizer.

Well it was up to him to pull his life together, to add value to his life. Oh yeah, he thought, that sounded rather positive.

Luis thought he should leave a text message for his sister-in-law's phone to call him for a long chat when she was free to do so. But he gave that idea the boot, thinking why drag Shannon into the emotional mess he was in any further. She'd already betrayed her husband with him on two occasions and Luis thought guiltily she'd probably commit adultery with him more out of sympathy than being motivated by desire to bury his erection into her pussy.

He sighed and decided to leave Shannon out of this. He would cease engaging in one night stands immediately. Perhaps then nature would take its course.

Two days later the CEO of the company Luis worked for called him to his office.

Luis went in relaxed as he considered his job was safe and wondered if he was required to lead a due diligence assessment of the proposed acquisition of another company.

"Hi Luis sit and here comes Sarah with coffee," Mike Feather said, confirming this was intended as an affable meeting.

After delivery of the coffee both guys watched the mobile butt as the PA walked off and closed the door.

"Brett (the director of finance) resigned this morning and the chairman and I have talked about you as the logical internal replacement. The truth is Luis everything stacks up for you with one notable exception."

Luis tensed attempting to think of what they had identified as his weakness.

"Well Mike I guess we all strive to be perfect and in synch with the requirements of the business."

"I agree and fortunately it's a deficiency you could remedy. As you know the director of finance sits on the board with Thelma and me as the three executive directors. Several board functions are held each year involving directors and their partners and..."

"And I don't currently have a partner and therefore would appear as odd man out."

"Yes exactly and I couldn't care less about that but the chairman does. He asked me to talk to you about the likelihood of your gaining a partner."

"Mike tell Arnold that it's almost six months since my divorce and I'd decided two days ago to find a replacement wife. In the best interests of me, and the company of course, I'll move in earnest to immediately fill that gap in my life."

"Well said Luis. Um do you have someone in mind?"

"Definitely."

"Well in that case the board is likely to accept the chairman and my recommendation for you to become our next director of finance. Congratulations buddy and may I say you'll have a partner in place within six months?"

"Yes but add it's likely to occur within three months."

"A regular partner is the minimum required."

"I understand Mike and thanks, I really appreciate your confidence in me."

Shannon the Matchmaker

That evening Luis called his brother Ben. After catching up since their last conversation more than five months ago Ben invited Luis to spend a weekend with him and Shannon.

"When?"

"We have this weekend free."

"Okay um may I speak to Shannon?"

"She's out till late. I'll get her to call you tomorrow."

"I'm wondering if she could find me a date so we could socialize as a foursome."

"That's a great idea. I'll mention that to her. She'll be more sensitive about the right kind of date for you whereas I'd probably end up suggesting a hooker."

They laughed.

Shannon called just after 7:00 next morning.

"Ben told me you are spending the weekend with us and he wants me to find you a date who I presume should be friendly and morally relaxed."

"Er really I'd like someone suitable to move in with me if we hit it off."

"What wife material?"

"Uh let me explain the situation."

After listening to Luis' explanation that he'd given up on one-night stands because it seemed so pathetic and pointless, Shannon laughed and was keen to help out. She already had someone in mind and welcomed the chance of being a matchmaker.

Luis told to go ahead and surprise him with the quality of her choice.

Luis received a phone text from Shannon late afternoon: 'All done and Leigh is lovely.'

He read the message twice and didn't know what to think

Leigh

Luis traveled the 40 miles to Chicago by train on Friday, arriving early evening and took a cab to his brother's apartment on West Madison Street and wondered what type of female his sister-in-law thought would be ideal for him.

In the lobby he called the apartment and Shannon answered and pressed the lock release to the elevators.

"Hi welcome," she'd said huskily, making kissing sounds into the communication microphone.

Riding to the 7th floor he wondered is his brother fully appreciated was a wonderful bang his wife was.

Sharron opened the door, stepped forward and kissed Luis sweetly and whispered, "She's here; be sweet to her."

Luis sensed their relationship had reverted to respectability and rejected the temptation to squeeze her butt as he was led to the living room.

His brother Ben greeted him and said he looked suave.

Sharron addressed the other guest and Luis looked at her, hiding his disappointment. He hadn't really thought about what she'd look like and guessed the default expectation would have been tall, blonde with big tits and slender hips.

Oh yeah.

"Leigh Johnson this is my brother-in-law Luis Bennett who I've told you about."

The slightly stocky pleasant-faced brunette with full lips - now that was a plus - smiled at him and Luis wondered was she concealing disappointment. Oh what did it matter because nothing was arranged beyond tonight and even if advanced beyond that either one of them could pull the plug. He winced thinking why be so negative.

Perhaps she liked having sex. Oh yeah, he smiled and returned her simple greeting of hi.

Shannon frowned at them both and said, "Come on you two, this is a friendly occasion and at least shake hands and smile at each other broadly.

The two guests shook hands and without thinking Luis looked into her green eyes and winked and was astonished to see a light blush appear on her cheeks.

"It... it is nice to meet you Luis," she said as he caught the scent of exotic perfume as well as her hint of nervousness.

Shannon stepped in and pulled them into her and called to Ben to serve the Martinis.

"Wow Shannon this is chummy," Luis said, thinking he should be first to speak.

"Shannon is my favorite sister-in-law," she said to Leigh.

"Oh I thought Shannon said she was your only sister-in-law."

"She is and that's why I'm so lucky."

They laughed with Shannon letting them go and saying now the ice had been broken.

In the SUV ride to the restaurant, Luis asked Leigh what did she work at.

"Didn't Sharron tell you that?"

"No."

"I work in law as an attorney and specialize in real estate, foreclosure defense and immigration and sometimes help out in family law when our small office becomes overloaded. And you?"

"I'm in business finance and begin my new role as director of finance with my company on Monday."

Ben their driver said, "Yeah bro, my congratulations on that big promotion."

Leigh smiled and said theirs were compatible vocations.

"Indeed and are you happy being an attorney?"

"Yes and no at least not in this city as it's overly competitive and things can get rather ugly at times. I came from a smaller city after my divorce..."

"Oh I'm sorry to hear that."

"What? Sharron didn't you tell Luis anything about me?"

Sharron said, "No I wanted to give you both a clean start and now that's happening. I suggest you tell Luis why you were nervous about this arrangement."

Leigh said nervously, "I'm a divorcee with a 5-year-old daughter and I employ a day-time nanny for Linda. This is the first time I've been out s-socially alone since the start of the marriage b-break-up."

"Linda eh; I bet she's cute if she's anything like you."

"What?"

Sharron turned from the front seat and said sweetly, "It's a double compliment Leigh; enjoy it. You two continue on getting to know each other. Ben and I will chat quietly and just ignore us."

"Y-you are not disappointed that I have a child?"

"Not at all. You see I'm a childless divorcee and I'm totally over my marriage ending unhappily. I'm rebuilding my life and Leigh I'm most interested in hearing more about you and Linda."

"Ohmigod."

The End

12
Please rate this story
The author would appreciate your feedback.
Share this Story

Similar Stories

Not Quite My Sister-In-Law An interesting day with his almost Sister-In-Law.in Erotic Couplings
Drawing a Nude Young Female 40 yr old man draws 20 year old female waitress nude.in Mature
Trick or... No, Just a Trick A woman dresses like a whore then acts like one.in Erotic Couplings
The Play Date Yolanda brought her daughter over to play and so did we.in Erotic Couplings
My Wife's Twin Expecting to surprise his wife in the shower...in Group Sex
More Stories