
“Have you ever walked to the edge of a precipice and looked down?” This is how my recent online conversation with a man contemplating infidelity began.
We often think of men as the ones seeking sex where it presents itself and never turning it down, but it’s far more complex than that. It’s a stereotype like women needing an emotional connection before sex. What is interesting is that someone would buck the stereotype to talk about it.
His story was a familiar one. He was filled with anticipation, apprehension, and awakening. But his potential affair partner made sure he saw the moral and emotional toll affairs can take before they slept together.
Taking the Plunge: A Leap of Faith into Infidelity
Desire ignited his journey. Devoid of passion in his otherwise fulfilling marriage propelled him into the uncertain world of online married dating.

His initial discomfort was akin to being “a fish among sharks.” His determination overcame doubt, reasoning, “nothing risked, nothing gained.”
An Unexpected Connection: The Bonds that Bind Us
His foray into the infamous Ashley Madison, notorious more for its 2015 security breach, brought an unexpected early bond. He’d shared a piece of his soul in the form of erotic writing on his profile that attracted a lady. Their connection was instant, magnetic. “My day would brighten at every alarm,” he confessed, underlining the anticipation their digital encounters sparked.

A Road Less Traveled: Emotional Readiness and Moral Considerations in Cheating
However, as he teetered on the brink of crossing the Rubicon, he faced a surprising revelation from his digital confidante, a seasoned player in the game of deceit. Infidelity, she reminded him, isn’t just an exciting escapade; it’s a complex journey fraught with practical, financial, and moral implications.

To navigate these complexities, she told him to get “How to Cheat: Field Notes from an Adulteress.” Yes, that book! I was chuffed when he told me that she’d recommended my book, lol. Who wouldn’t be? 🥹
My guide gave him new perspectives on the mechanics of cheating. What it also did was show him he wasn’t ready.
From Hindsight to Foresight: The Lessons of Emotional Readiness
He identified three pivotal lessons from his journey —
- Gauging one’s emotional readiness is crucial before doing something you’ll never be able to undo. He underscored, “A desire for passion must be tempered by an awareness of the potential consequences.”
- He learned that cheating is not merely a forbidden adventure; it presents significant moral, safety, and financial considerations that demand careful thought.
- He understood that recognizing when it’s not time to cheat is as important as knowing when it is.
After a year-long pause and some introspection, he returned to the scene armed with a better understanding of the realities of cheating and a renewed sense of readiness.
“Cheating is no matter to be taken lightly. If you want to have fun and not get caught, it takes a lot of work,” he warned, his experience serving as a crucial reminder of the importance of mental and emotional preparedness in navigating such sensitive terrains.
Takeaway
Sex is the easiest part of cheating. Finding someone, getting to and from a date, and paying for it are things you need to consider as well. But those skills can be learned. What can’t be learned is how you’ll feel when the sex is over. In the swell of emotions and new relationship energy, it’s easy to lose sight of the fact there might be an emotional cost.
What I like about this story is that he managed to experience all of that but then see beyond it. Not many have that ability, and he might not have either if it wasn’t for his prospective lover, who gave him the tools he needed to make the best decision for himself.
Why would she do that? Perhaps to make sure he wouldn’t fall apart after their first meeting. Or she did it to save herself from her own emotional rollercoaster of meeting a nice guy who withdraws after the connection was made. Either way, I think what she did for him was remarkable.
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© Teresa J. Conway, 2023