Cheating Part II: How much flirtation is healthy and when does it become infidelity?

This is Part Two of a multi-part look at infidelity. Part One of this series asked some questions about the morality of cheating, and whether it is relative to the attitudes of the participants. Click here to read Part One.

Here in Part Two, we’ll look at a few real life situations that are what you might call “fuzzy infidelity.” How do we define the line between flirtation and interaction that qualifies as cheating, or, as wrong? Is it okay, or healthy, to cross the line a bit? How far? Where do you draw your line and have you crossed it? Please share your thoughts and stories in comments to further the discussion.

Much of the stories we hear about marital infidelity involve clear sexual interaction; with these, while opinions may differ about whether the interaction was right or wrong, there’s little ambiguity about the fact that “cheating” has occurred. But, in real life, we have situations that aren’t necessarily innocent, but do not involve any sexual acts – or, perhaps, no sexual interaction at all. I’d love to here about any such situations you’ve encountered. Here are a couple anecdotes from my own life: would they qualify as flirtation, or cheating? Were they harmless and healthy, or deceptive and wrong?

One of these “fuzzy” type situations happened with a friend’s fiancee, Lisa. The incident happened one night as a result of a spontaneous Truth or Dare game that started up between a group of close friends at a Fourth of July party. You can read the entire story of that night in my recently published book “Dare.” ~ Available now on Amazon

The incident with Lisa didn’t involve any sexual activity, and we were actually miles apart when the “questionable” part occurred. Before leaving the party with her fiancee, for her last turn in the Truth or Dare game, Lisa had dared me to go in the bathroom and take a nude mirror-shot selfie and text the pic to her and the other people playing. The dare stipulated that I be erect when I took the pic. As I walked off to do the dare Lisa mentioned something about, “It has to be a good, clear photo, bonus for sending a couple…”

I sent each person the photo individually. Then I sent two more to Lisa, close-ups that I had taken while I was still sitting on the toilet “preparing” – one flaccid and one of my hard dick. I lied and texted her that I couldn’t remember if she had said to send her a few. Lisa made no mention of the two extra photos she received – thank God.

If a line was crossed, it was probably about a half hour after she left, when I received a text message from Lisa. The following short conversation occurred:

Lisa: Hey, thanks for the xtra pics. U send those to others or just me?
Me: Just you. Too much?
Lisa: Would I be a horrible person if I kept them?
Me: Probably – lol.
Lisa: I think I will if u don’t mind?
Me: Go for it.
Lisa: I was thinking that perhaps we can keep it between us, the xtra ones you sent?
Me: Okay.
Lisa: And Duncan…
Me: Yes?
Lisa: I like them.
Me: I’m glad. You’re welcome to use them for masturbating… Lol, totally kidding.
Lisa: So I can’t?
Me: You would?
Lisa: I might.
Me: =0

And that was it. Flirtation? Infidelity? Horribly wrong behavior? What do you think?

For those that think this was wrong of Lisa or me, would you consider it “cheating,” or wrong for other reasons? Was I the first to do wrong by sending those extra pics? Was it the secretiveness when she asked me to keep it between us? Or, perhaps it became wrong when she continued even after I answered her that she would “probably” be a horrible person if she kept them? Or, did it cross the line when it turned sexual with her saying she might use the photos?

How about pure mental infidelity, is that a thing? If she masturbates looking at the pics or thinking of me – her soon-to-be-husband’s friend – is that cheating? How about if I get off on the thought of her keeping and looking at the pics of me, am I betraying my friendship?

Would the context of the incident, where lots of shocking behavior from all of us had already occurred that night, excuse our behavior to some extent?

Right or wrong, I haven’t experienced any negative repercussions do to the incident and as far as I know there’ve been none between Lisa and Sean – who were married two weeks after this happened. I’m dying to know what became of the photos, but haven’t dared ask. I still remember seeing Lisa’s amazing tits that night – no photo necessary. She actually has seen my genitals in person since, but that’s a whole ‘nother story – takes place in Volume II of the Sinner Saint Diary series actually.

Is it ever cheating if one merely exposes their body without their spouse’s knowledge? Or, does the exposure have to accompany some kind of sexual interaction – even if it’s on video or over the phone? I’ve seen someone expose themselves numerous times without their husbands around. A few years ago two co-workers stopped by my house, one married and the other separated. After a drink or two,  we got talking about boob jobs. The separated co-worker volunteered into evidence her own boob job, and then my boss – the happily married one of the group, took her shirt and bra off, and sat topless for a spell, so we could asses whether or not she needed a boob job. Unless a woman was planning a  career as a Dolly Parton impersonator, it would be ridiculous to change such perfect breasts: did she just want to show her tits?

The most extreme exposure story, which is told in the “Campfire Talk” SSD story to be published, was when a friend took off all her clothes in front of a group of us camping, after her boyfriend got upset about her wanting to go skinny dipping with the rest of us. We ended up going swimming without her, while she fought with her boyfriend. By the time we returned, her boyfriend had left the campsite and driven home – back to Los Angeles which was about a hundred miles away. As as twenty of us warmed up around the fire,  our friend made sure there was nothing of her we didn’t see.

Here’s a link to next the next post in series:


If you enjoy true accounts like this – of scandal, infidelity and testing of boundaries, I think you’ll love experiencing the scandalous saga among friends that takes place in the recent inaugural SSD publication, “Dare” available now on Amazon – click here for free preview.



Cheating Series:

Cheating: Issues, Questions & Implications of shifting attitudes towards marital infidelity.
Cheating Part II: How much flirtation is healthy and when does it become infidelity?
Cheating III: Sex in Head, Mental Infidelity
Cheating IV: Anatomy of Infidelity
Cheating Part V: Loopholes, Free Zones and Grey Areas.
Cheating VII: Time Warp Infidelity – Sex After or Before the Relationship?
Cheating 7: When You Stumble Upon Much Better Sex Outside Your Relationship
Cheating 8: Is it Really Sex or affection we Want or is Cheating a Settlement?
Cheating 9: Considering Special Features in Defense of Sexual Infidelity
Cheating 10: Looking for a bit of fun before spilling the beans
Cheating XI: How Not to Sleep With Married People


And now about you:

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