Jenifer's Choice

By Anthony Monroe

Jenifer’s Choice
We make choice every day, and sometimes those choices can bring about something that we never expected. That what happened to me when Jenifer Simms made the choice to have an extra-marital affair with me. Join me as I tell you the story and consequences that resulted from Jenifer’s Choice...
Jenifer’s Choice is an erotic adventure that allows one man to discover his true nature, another to be the man he always wanted to be, and yet another in a situation in which no one can possibly win...or can they? Find out and answer that one for yourself.

• Language: English
• Publisher: Anthony Monroe
• Release date: Oct 21, 2020
• ISBN: 9781005821319

Anthony Monroe

I am an aficionado of all things erotic.

Book preview

Anthony Monroe

Sometimes the choices we make have long reaching consequences…

This is a work of fiction. It is meant to be entertaining. Enjoy but, please understand the difference between fantasy and reality.

Smashwords Edition

TABLE OF CONTENTS

Prologue

Chapter 1: Lust at First Sight

Chapter 2: Show and Tell

Chapter 3: Friends with Benefits

Chapter 4: If It Ended Here…

Chapter 5: Sometimes It’s About More Than Sex

Chapter 6: Homemaking

Chapter 7: Remaking the Past and Shaping The Future

Chapter 8: Proof of Betrayal and Desire

Chapter 9: She Knows Me So Well

Chapter 10: Where Do We Go From Here…

Chapter 11: We’re Not Your Ordinary Couple…

Chapter 12: The Couple That Plays Together…

Chapter 13: …Gets Fucked Together

Chapter 14: What Nice Secrets You Have…

Chapter 15: Shared With Love

Chapter 16: Meating The In-Laws

Chapter 17: New Beginnings, Old Problems

Chapter 18: …Let No Man Tear Asunder…

Chapter 19: Home-Cuming

Chapter 20: Sister Wives

Chapter 21: Sweet Beginnings and Bitter Endings

Chapter 22: It’s A Party and Everyone is Coming…

Chapter 23: Tipton’s Party of Two…

Chapter 24: Released and Relieved

Chapter 25: There Will Be Surprises…

Chapter 26: …And Happy Endings

Epilogue

Prologue: Forever My Lady

I awoke to the music of Jodeci’s ‘Forever My Lady’ being played by my MP3 player/ alarm; I had to laugh because the person lying next to me was just one of the ladies in my life. She was however the lady of my dreams, and when we met, I had no idea how just a few months together would change our lives forever.

It’s one thing to have an affair with a married woman, but to have it turn into a full-on cuckold creating affair that ends with me having both her and my sister-in-law pregnant, that’s another thing all together.

I feel the princess cut diamond wedding ring slid roughly across my palm as my wife turns her hand to grasp mine. She looked over her shoulder and smiled before releasing a contented sigh and snuggling in.

It was Monday morning and I am just waking up with a coworker’s ex-wife naked in bed, the sounds of my sister-in-law talking to my brother, and my dick was once again responding faster than my brain could to the changes in my life.

What had started as a case of mutual curiosity and lust would reveal family secrets, ruin a man’s life, and make me the father of a child I could never claim.

Before you rush to judge me for stealing another man’s wife, and enjoying it; let me give a little background, and if after you have heard my story you still want to judge me then so be it.

Chapter 1: Lust at First Sight

My name is Alexander Tipton, by trade I am an Aviation Electrician Mate First Class in the US Navy; but that’s merely by choice. I’ve always believed that every able-bodied man ought to serve, and when I graduated high school, I opted to forgo college followed by working in the family real estate investment business, while living as a trust fund kid as an adult.

Instead I choice to enlist in the U.S. Navy that was almost six years ago; now at twenty-five I’m celebrating the end of a nasty divorce, planning my future, and despite hating my ex-wife I am about to enter the hallowed halls of Fair Oaks Academy to stand by her side as we celebrate our daughter’s kindergarten graduation.

I make it a point to be involved in every aspect of raising our lovely daughter, Natalie and if that means dealing with the façade that the parents of Virginia Beach’s upscale Oak Lawn Heights present to the world then so be it.

My wife (ex-wife) had insisted on buying a five bedroom three bath colonial in Oak Lawn even though we only had the one kid, at the time I didn’t complain because to be honest Norfolk was going to be my last transfer and I felt that I could use the connections that affluent neighbors could offer when I transitioned into my life post military.

That is how I met Mrs. Jenifer Simms.

Mrs. Simms is or rather was my daughter’s kindergarten teacher; she caught my attention previously at a PTA function that I was forced to attend.

I hadn’t been to Oak Lawn Academy since the start of the school year and here it was almost Christmas and I was entering the pristine marbled hallways in a grease stained uniform that I was forced to wear since my darling wife flaked on her portion of the volunteer work.

My (ex) wife had pledged both our time and financial resources to the end of the semester Holiday festival and knowing how much this meant to my little angel I couldn’t back out now.

While normally I don’t spend much time looking at the women who attend these functions, it should be known however that Oak Lawn has some of the best pussy in the Hampton Roads/Tidewater area.

Since Ashleigh moved out of the house and into a condo (that I paid for) I’ve been taken advantage of the opportunity; you’d be surprised the speed at which legs open when their owner realizes that you can afford a house in the high six figures.

Waiting for the meeting to start I made my way through the mass of people, and although most them happened to be my neighbors, you would have thought they’d never seen me before. Many of my so-called neighbors didn’t even bother to say hello and as I leaned against the wall, I relished the fact that despite my less than stellar appearance I could probably buy each and every one of them if I wanted too.

With that thought in mind I put on my best smile, one that told them all that ‘yes my kid is indeed enrolled in this school’, and no despite my hands are full of these delicious chocolate no-bake cookies I’m not just here for the lukewarm punch and overly sugared cookies.

From my little corner in the back of the room I couldn’t help but notice a woman whom I could only describe as sexy beyond believe. She had seemed to notice me too and despite my workaday look she and I locked eyes several times.

I spent several minutes watching as she made her way through the crowd, I admired the confidence that she displayed. I tried to remember every detail of this woman who stood maybe 5’4" even with dark suede leather stiletto heels she wore.

I shyly averted my eyes every time I noticed her smiling in my direction as she stroked her shoulder length coal black hair behind her ears giving me every opportunity to admire her deep jade green eyes, but even their alluring nature couldn’t distract me from the way the black and cream thigh-length compression dress curved around petite frame.

I stood in rapt silence as I watched her move to the front of the class and begin her presentation in a voice that even though it was both raspy and heavily accented with a deep Texan twang, made my dick come to life.

I was finally shaken back to reality by the thought that my cock was getting hard in a space where my daughter laughed and played; I began laughing, thinking about how George Bush would have had a field day in office if he could have imitated her quick-witted confidence and southern charm while delivering his speeches.

I would just like to thank you all for helping me to ensure that this event continues to be the jewel of the season’s festivities, and I can’t thank all of you enough for helping me succeed in my first year… she began; to be honest until then I hadn’t considered that she was a teacher, let alone the co-sponsor for this event.

My mind drifted as began looking at her differently, she could have easily been someone’s trophy wife. I couldn’t take my eyes off her, and to be honest it was a bit embarrassing.

…I want this to exceed not only your child’s expectations, but also those of other less fortunate children in the community…

The room erupted in applause, and my thoughts were refocused as I too joined in the clapping.

She waited like a practiced speaker for the applause to fade before continuing, …this of course wouldn’t have been possible without Mrs. Tipton stepping in to ensure our fundraising was a complete success…

More applause from the room, including myself; I actually applauded just so I can have her look in my direction.

She raised her hands and the applause faded, Mrs. Tipton for all her efforts didn’t quite raise enough to completely cover the expenses that resulted from the unexpected downturn in the economy, but she assured me that, Alex… she said pausing and directing the room’s attention my direction.

…Mr. Tipton is more than willing to help should we need any assistance she concluded with a smile that displayed her Hollywood white teeth.

Several of the parents continued looking my direction, I’m sure they would have never been convinced that this outsider wearing a stained Navy work uniform was the reason that their precious little angels would be able to indulge in all the sugar they could handle while handing out gifts with their classmates to less fortunate children, and by the end of her presentation it no longer mattered what I was wearing because she had assured them that I would be footing the remainder of the bill for the festival; many of the parents, especially the men was glad to know that they wouldn’t have to pay for the chance to once again prove why Oak Lawn was the envy of Virginia Beach.

For me, I would have given anything to be able to see even more of Mrs. Simms; my pride included.

As the meeting began winding down I found myself swelling with pride, Oak Lawn is known for being snooty, and despite owning one of the biggest houses in one of the most prestigious neighborhoods; I could feel a few of the Oak Lawn snobs glaring my way as if in judgement of me for ‘buying’ my admission into their elite little circle.

More than a few of the women came by to ask me how my wife had convinced me to ‘sponsors’ the festival, I really wanted to tell them that I wasn’t sponsoring the event out of the goodness of my heart, but in reality because Ashleigh knew that I wouldn’t say no to the walking sex dream that was Mrs. Simms, being in mixed company I opted for the polite I’ll do anything to make my little girl happy… as my standard response.

While I never found my service to be anything but a source of pride, on more than one occasion it has been a source of contention mainly by those who feel that my net worth and not my reasons for serving should define who I am.

Ashleigh was one of those people; she would look upon with me what I felt to be disdain whenever we invited sailors into our home for the holidays, she could never understand why I chose to hang out with people like them and not our condescending neighbors whose shoes often costed more that the cars that those service members were driving.

That was what ultimately drove us apart; I tried to remain low key, but she had to have her dream life to include her dream house; part of that dream life included me paying six figure alimony but when my lawyers convinced her that she’ll never see a dime of my families money let alone be able to afford the taxes she’d have to pay on the 3.4 million dollar house she quickly came to her senses, leaving me with a fight to see our daughter and more house than I know what to do with most of the time.

Jenifer however seemed unphased being surrounded by these uppity folks as she excused herself from a group of stragglers and made her way to where I stood biding my time; we still had a few details to discuss before I could make my exit, so I was in the walking around the classroom, looking at the macaroni art enjoying another handful of cookies.

Without asking she reached up and took my gold crewmember wings between her thumb and forefinger, So what squadron are you with? she asked while allowing her fingers to trace the curve of the stitched wings on my chest.

303rd… I said while studying her features and allowing her subtle lilac based perfume to fill my nostrils.

I found myself being drawn to her; I looked down and saw a small smile spread across her lips as she asked nonchalantly You wouldn’t by chance know the person my husband told me about, they call him Mr. Ed, you know him?

She laughed when she saw me visibly blush; I had picked up the moniker Mr. Ed during my time in basic training. They guys in my training squadron started calling me that when they walked in on me taking a shower one morning after physical training.

Not to brag, but I’ve always known I had a large cock, and I’ve never loss a literal dick measuring contest, but my cock has scared away more than a few unwilling women, and as a result it’s not something that I advertise.

I wasn’t sure where she was headed with the question; was she letting me know she was married or coming on to me because her husband had told her about some Black dude in his squadron with a huge cock?

I could only muster a faint maybe…I’ve heard stories but, what did he tell you about this Mr. Ed? in response.

Never mind that…, She said playfully as she stepped back and sat on the edge of a child’s desk.

Crossing her legs at the thigh; she continued, …you should know him and my husband… NAS Norfolk isn’t that big, my husband name’s Marcus. she said while once again slowly fingering my wings once more and allowing her hand to brush along my chest before waving at the parents conversing with the few other parents as they said goodbye.

I stood there for several seconds thinking to myself how I loved everything about her; her voice, her confidence, but more importantly I loved the fact that she was something that I could never have.

Or could I?

I had spent almost an hour in her presence but it wasn’t until she was leaning over her desk, with her back to me, that I really begin to think about the things I could do with such an attractive playmate; I had once been apprehensive about coming between a married couple’s happiness but as we were giddily laughing and she told about her upbringing and how she met Marcus did I begin to want her even more.

She had an easy smile and self-assurance that comes from knowing the power of her sexuality.

I could have stayed there for hours studying the way she flaunted the fact that she was ‘off limit’ and that would have made me want her even more.

She stood and walked the last couple to the door, and I was mesmerized by the way moved while pretending not to notice the wife almost pulling her husband out of the room.

I found myself hypnotized by the clickety-clack of her heels on the tiled floor and while sitting on the edge of too tiny desk I began to imagine the curves of her body beneath the clinging fabric; I couldn’t stop visualizing her milky white naked body pinned beneath me while repeatedly slid my caramel-colored 12 inched black dick into what I imagined to be a tight pink pussy.

I had been fourteen or fifteen when I last fantasized so vividly about a stranger before, but then it was my mother’s best friend and in my defense, I’d just seen walked in her while she was semi-naked and getting ready to switch into her bathing suit.

Jenifer however was something else altogether she had done nothing overtly sexual and that made me want to be with her even more.

As she returned to where I sat, she leaned around me and began shuffling items on her desk. So, can I count on you to help me decorate for the festival too…I could really use the help.

Sure… I said knowing that it’ll give me more time in her presence, …but what about your husband? Think he’ll help?

I doubt it. She said just before heading in the direction of the door, he doesn’t like children.

She said it almost sadly while leaning against the wall, I’m just glad you do, I told her fighting the urge to do or say something stupid.

Thanks… she told me while extending her smallish hand.

I took her hand in mine and when I did, she smiled up and said, I look forward to seeing you again.

She had no idea, but my mind was already thinking about how to make that request come true.

While sitting in the parking lot I made it my mission to find and befriend her husband just so I could see even more of her.

Over the next couple of weeks I seemed that I was too busy helping with the upcoming festival or planning my pending separation from the Navy to focus on anything else; I finally had a chance to return to my mission at a squadron return party. As usual I was one of the few black faces among the majority white crowd; but this seemed to always work in favor. I was known for my partying; this was on purpose.

Having already decided upon leaving the Navy and securing my honorable discharge, all I had to focus on now was leaving my mark. I was always on the lookout for networking opportunities and it seems that someone was always introducing me to new people. This particular night included and introduction to Mr. Jenifer Simms a.k.a. Marcus.

After hitting the max allowable ‘two drinks’ at the command sponsored party I pulled a group of friends together and suggested that we head to an out of the way strip club; one that was known for its loose women and cheap drinks. I made sure the group included my new best friend, Marcus.

I loved The Landing Strip; it had everything I needed to get my mind off of work. As we piled around perverts’ row Marcus made a comment how the petite dancer blonde making her way on stage was nothing compared to his wife, he boasted how Jenifer would put her to shame.

We all got a good laugh because the dancer was attractive by anyone’s standard. She had natural C-cup breasts and shoulder length hair trimmed on one side highlighting her ear’s multiple piercings.

Oh, so your wife’s name is Jenifer? I asked almost certain that this was indeed her husband.

As the dancer spun around the pole, the guys began to hoot and holler while throwing singles on the stage.

I ignored the show as best I could by focusing on my friend. You don’t have a picture of your wife I asked, because I know she can’t be hotter than Savannah there. While nodding my head toward the dancer who was now leaning backwards while spreading her legs and exposing two very puffy pink lips.

Marcus feigned interest in the show; reaching into his wallet he pulled out a picture of Jenifer seated astride a majestic black horse with a white star on his nose.

I smiled to myself upon seeing that this was indeed the same person; he noticed the smile on my face.

What? he said as he returned the picture to its place in his wallet.

Not wanting to let on I told him about meeting her at my daughter’s school by making another one of my usual race related comments, So she like’s ‘em big and black huh?

That got everyone laughing including him and the ice was broken; Marcus without realizing had managed to stoke my desire for his wife even further when he commented Jenifer would never be with a black dude. Besides I’m all the man she would ever need.

As the dancer exited the stage I invited the dancer over and as she sat on my lap I saw Marcus secretly checking her out; I slipped several twenties into her G-string and told her to give Marcus a private dance; she smiled at me and so did the fellas because they knew what happened in the private booths.

As they walked away, he turned and saw us smiling and waving as she led him behind the curtained wall. I had to find a way to endear myself to my new friend; I knew that having a secret was one way of doing it sooner.

Besides, I had to see for myself if he truly was all the man that she’d ever need.

After several songs I had forgotten about him, it wasn’t until the chorus of cheers began that I noticed him and the telling smile that comes with making a perfect landing.

So, how was she? I asked as settled in next to me while reaching for his beer.

Not bad, but her tits are fake. He said almost complaining.

The rest of our group was all admonishing him with the standard response being I bet you didn’t complain while they were in your mouth.

I pushed him further trying to get him to open up and admit even more, I wanted to give him a reason talk more about his wife.

What, you don’t like big tits or just not that big? They looked perfectly normal to me. I said.

This seemed to work because he offered Jenifer’s tits are a natural C cup; big, firm, and natural. I knew her’s wasn’t because they didn’t jiggle same way.

I agreed with his preference for natural tits and as we downed yet another pitcher of beer and we sat back, and he explained what took place during their private dance. When he was done, he and I tried to guess whose tits were real or fake, I even convinced more than a few of the dancers to let us prove our theory.

Our club session lasted well past midnight when some of the guys who were both drunk and horny suggested