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One Too Many or Not Enough

"Is it wrong to have sex with your business partner?"

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Lynn is my lush. However, she also happens to be my best friend, my business partner, and with someone else. My name is Alex and this is our true story.

My best friends have always been female. In high school, my best friend was the soccer babe. In university, it was the skater chick that I eventually went on with to have three children. In divorce, it’s Lynn, who suffered through the whole break up of a long-term marriage six months ahead of mine. It was the life-changing experience that bonded us.

In years since then, we’ve been through the ups and the downs of being entrepreneurs. We’ve fought over money, or more precisely the lack thereof. We’ve listened to each other bitterly complain about unreasonable ex-spouses. But, we’ve also celebrated countless successes and been on amazing trips to conferences where we co-present in front of sometimes small and sometimes large audiences. We are really good at what we do together.

We both found new love online, both in distant cities through our travels. But, between us, we have seven children making conversations about relocating improbable.

There was one night, not so long ago, where Lynn and I were out to dinner together, drinking more than a few bottles of wine - not an unusual occurrence for us.

This night, in particular, was just one of those glorious summer nights – warm, still, and seemingly endless. There we were sitting on a patio together sipping our wine savoring the meal we shared.’

We are both in our mid-forties, but neither of us look it. Lynn is blessed with naturally tanned skin, long brown hair, and almost black eyes. On this night, she was wearing a simple white dress that hung perfectly from her athletic shoulders, draped perfectly over taught breasts, and finished teasingly at mid-thigh.

Her legs have captivated me for as long as I’ve known her. She has those narrow ankles and athletic calves that one gets with the insane workouts she puts in at the gym. She rarely wears stockings because, with her legs, it would truly be a travesty.

Needless to say, she turns heads. Not only the men look at her, but the women too. Many people judge her based on her appearance, which isn’t fair, but I’ve come to appreciate the mixed blessing that represents. Most men fantasize about her. Most women are jealous. I’m not entirely immune to either perspective.

Not that I’m a chump by any means, but I couldn’t be more strikingly different than her. I’m tall and athletically toned, but with light skin because of my red hair. I’m the introvert of our partnership. I’m the thinker and the doer, whereas she is the social conversationalist and task delegator. We are admittedly and knowingly completely opposite people, and in our presentations, it’s become part of our shtick.

What looks glossy on the outside, however, is sometimes less polished on the inside. We’ve both been through so much trauma and drama together in our love lives. She knows my skeletons and I know hers.

After months of running on a treadmill between our children, our struggling business and our distance relationships, we finally had an opportunity to stand still. In those hours of being and laughing together, I found personal peace and happiness. I found myself truly enjoying spending that single solitary moment of life with her and just her – not thinking of the past, nor of the future.

We hailed a cab back to her place. Most nights I see her home, walk her dog and say good night. But tonight felt different to me. In the dimmed back seat of a 2011 Toyota Camry sedan, I just felt a deep need to be closer with her.

In the darkness of the back seat, my hand came to rest on her thigh, just above her naked knee. It was nothing but a gesture of closeness at the time. However, a few blocks later, my palm and fingers ever so noticeable slide barely an inch higher. I kind of expected an objection or a redirection on her part.

Nothing.

Every block closer to our destination, my touch lightened and my hand slipped higher.

By the time we reached her house, my hand half-hidden under the dress’s seam and my fingers dangling over the warm soft flesh between her legs. It was just us and felt surprisingly comfortable.

I paid the driver and followed her in. The kids were with their father that night and as luck would have it, so was the dog, relieving me of my traditional chore.

We entered the living room, collapsing together onto the sofa. She began checking her phone for messages from her boyfriend. She always had men texting her with various level of propositions. She started laughing at one, in particular, a high-profile celebrity whom she had met many years ago and stayed in contact with. She turned the phone to show me his latest message. We had always been completely honest about our love lives – the highs and the lows, the good and the bad.

As I leaned in to read the latest text, my hand reassumed its previous position.

We laughed together at the silliness of modern relationships – such a farce! While we are good at acting monogamously, we aren’t very good at thinking that way. We have often used Tinder together while we are travelling on business just to see what interest we can generate.

She was still checking her messages when her legs parted ever so slightly. It was a silent grant of access to perhaps go further than I had in the cab earlier.

There is a brief moment in time when you think to yourself that this is perhaps wrong, but in honesty, it passed quickly. was an electrostatic field between us that night that I can’t quite explain. It was drawing us unwittingly closer to each other.

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Her eyes closed, her head tilted slightly as she emitted a soft and involuntary moan. A moan that called for more attention.

A second later, I reached her panties. The tip of my fingers rubbing over the silky fabric falsely guarding her most intimate privacy.

There was a minute or so of a lack of acknowledgement of the path we were so clearly on. That was, until she lifted and spread one of her legs over my lap granting me full, direct access. My now exposed philandering fingers, unabashedly stroked against the folds beneath her skimpy panties. Her head was thrown back with low guttural moans of distinct pleasure.

Without opening her eyes or any reaction at all, her own fingers reached up to her waist, tugging at the corners of her panties, and removed them on my behalf. And there it was…her naked pussy so perfectly laid before me. It was to me as perfect at the rest of her. I have never seen anything else in life that I wanted to taste and suck so badly.

My fingers reassumed their upward and downward massage over her now full nudity. I slipped a finger inside her. I felt her wetness building. I almost felt as though I could have lifted her entire body off the sofa with the touch of my finger. Tightening my grip, I smothered her pussy under my palm, my fingers buried inside her moving my forearm up and down. Her mouth widened, her breathing feels heavier. Impatience was building.

“Fuck me or suck me off,” She finally pleaded.

I could feel my cock dying to be one with her. My reply was simple and obligatory, “I will give you both.”

As I rolled over onto her, my pants, underwear, shirt, everything peeled off of my body. By the time I was between her legs, my swollen knob was right there, positioned between the two guardrails that define her so fuckable pussy.

Nary a single objection, as the engorged tip of my cock penetrated her. I dipped it in an out a few times, smearing my smoldering rod in her wetness and relishing her pleas for deeper and more.

“Give it to me…Don’t stop…” The commands were given between tired breaths. “All of it.”

Within a minute, I was happy to oblige having sunk the entire length of my shaft inside her. Nothing has ever felt that good. As close as we are as friends, I wasn’t sure if what we were having at that moment was sex together or making love. It was so incredibly intimate to release all that tension in the form of pleasure, each of us encouraging the other to ever higher levels of ecstasy.

It was so intimate to share that with someone I was so close to me in my life. My cock was admittedly splitting at the seams to release, but with all the alcohol in our systems, I was able to control ejaculation.

At one point, I held her very close to me. My cock was buried so deeply inside her, completely filling her. She and I both felt it. It was like flying so close to the sun. I could feel my loins releasing, my cum streaming into her. I felt this undeniable instinct to fill her pussy with as much of my seed as possible.

As much as I know she enjoyed having me cum inside her, I knew that she could only reach an orgasm herself with oral sex.

With the moment still ever present, I slid out of her and dropped to my knees between her still spread legs. I placed my mouth onto her aching clit and between sucking lightly with licks and kisses. My tongue would swirl it in a circular motion for a minute or two before changing to a long vertical paint from her pussy hole to her ebbing button.

I loved the taste of her pussy. It wasn’t aggressive. It had a very light scent and taste with a creamy texture. could suck her off for hours.

"Oh my god, that's so good, please don’t stop,” she was begging me over and over again. I could hear her building and I could feel her swelling inside my mouth. I wanted to please her so badly. I’ve always wanted to please her in everything we do together.

When she climaxes, her body tightens. Her pussy engorges to produce a hard nub. I know her so well that I know she liked having it sucked as it throbs its way through the entire orgasm. I also know that she becomes extremely sensitive after it begins subsiding. These things we have talked about over the years, but I never thought I’d ever have the opportunity to be with her that way.

Through all the years and time we had spent together, oddly we have never really considered each other viable or suitable partners. Best friends most of the time, but when we fight – we are vicious like brother and sister.

I stayed over at her place that night after all that. We woke up the next morning and at first, interestingly we were embarrassed by our adulterous treachery. But later, something changed, We’ve known each other for so long and been through so much together. We sat back and laughed at ourselves, unable to pick a new label for our relationship.

It’s now been three months since that fateful night. It never happened again. We are still best friends. We are still business partners. And yes, we are still with other people.

At times, I wonder. At others, I think maybe we should just accept it for what it is and what it was – a beautiful moment between two people who share a deep commitment to each other. What do you think it is?

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Written by ForeYou
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