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


And now about you:

Responses will be shared anonymous

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

  1. Pingback: Cheating 9: Considering Special Features in Defense of Sexual Infidelity | The Sinner Saint Diary
  2. Pingback: Cheating 8: Is it Really Sex or affection we Want or is Cheating a Settlement? | The Sinner Saint Diary
  3. Pingback: Cheating IV: Anatomy of Infidelity | The Sinner Saint Diary
  4. Pingback: Cheating VII: Time Warp Infidelity – Sex After or Before the Relationship? | The Sinner Saint Diary
  5. Pingback: Cheating 7: When You Stumble Upon Much Better Sex Outside Your Relationship | The Sinner Saint Diary
  6. Thanks for the reply.. I really enjoy your posts.
    It’s probably a given that people will flirt, and as a result, cheat; as to suggest that there is only your current partner who is ‘the only one’ for you on this earth, is highly dubious. Especially considering the relatively small number of partners we get to sample, prior to selecting our spouses…

    Liked by 1 person

    • Yes, monogamy may go against our nature, but what if their really is a God and what if he really does intend for us to be devoted to one person? Also, at some age when sex may be less important, are there rewards that pay off for those who remained devoted to one partner?

      Like

      • I suppose religion is always a controversial topic, however humans sin across the board, be they religious or not.
        To say we should follow the 10 Commandments to be fulfilled in life is one way to prescribe the ideals for one’s life I suppose.
        There may be benefits later in life, such as co-dependancy, however there seem to be many senior citizens getting divorced or in relationship conflict these days that may counter that argument.
        Then again, all the old couple’s interviewed in ‘When Harry Met Sally’ might be what we’d like to hope for as a reward for manogomy!
        Look forward to your next post!

        Liked by 1 person

  7. It is interesting such in-depth analysis of cheating. Perhaps it is also good to consider if true love is more common, or wandering thoughts of bedding another. I’d suggest the latter.
    In the animal kingdom, there is no such concept of marriage.. do we do it to bind ourselves artificially ?

    Liked by 2 people

  8. Pingback: Cheating Part V: Loopholes, Free Zones and Grey Areas. | The Sinner Saint Diary
  9. Pingback: Cheating III: Sex in Head, Mental Infidelity | The Sinner Saint Diary
  10. I’m drawn to quite a few of your posts and thoroughly enjoy the read. You’re quirky and realistic… but what I enjoy the most about your stories is how you don’t try to ‘justify’ yourself with infidelity/cheating. You explore it with us… and this makes the experience both more personal and enjoyable!

    I would like to respond to both your Cheating Part I & II, as well as Most Arousing: Silent, Risky & Simple.

    Firstly… yes, I think it is cheating. But… that is assuming the relationship between Lisa and her partner is discrete and monogamous. I know some polyamorous couples, swingers and real BDSM thrill seekers who have committed to much more without ‘cheating’. I have known people to also say less and ruin their entire relationships. However, her secrecy in the photograph affairs suggests her partner probably would not be pleased. We all have our guilty pleasures right?

    I think it’s natural to arousing thoughts when an attractive friend or stranger suggests they’ll get off on you.

    Also, personally… I’m someone who wouldn’t cheat on a partner too. Although, I am someone who has engaged with cheating partners. Some of my best sexual experiences which have made me “drunk with arousal” was with someone who was in a monogamous relationship and tried to keep it secret from me during the stages of our platonic friendship. Long story short, it all began with friendly encounters and light teasing. Then, I discovered in one way or another that he couldn’t keep his hands off himself (and eventually, me) whenever we talked from distance or in the same room together. His thoughts and pleasures were erupting from fantasies about me (and mine too, of him). It was a mixture of silence and riskiness, through his simple actions of hiding ra relationship from what seemed like the words and continuously taking me back to his house. It was as simple as masturbating often enough, as naturally as a coffee addict would lunge towards the first mug of coffee in the morning, to the thought of someone else who wasn’t the person you were meant to be committed to. Do it once, or maybe twice… sure, we all have a dirty little secret when our hands are upon ourselves? Maybe it becomes cheating when the small guilty pleasure becomes and addiction stronger than your partner, for whatever undisclosed personal reasons which dwell inside the mind of cheater?

    Concluding the long post, I just want to say your blog is rather addictive and I look forward to reading “Dare” when I have the time.

    Liked by 1 person

    • Thank you very much for your interesting and thoughtful feed-back – It gave me topic for cheating part 5 (already wrote 3 and 4).

      I’d be happy to send you a free copy of Dare. If you read it, I’d really appreciate some feedback.

      Yes, well that’s another angle – one I haven’t encountered- the cheater hiding their relationship from the other woman/man. So, he acted like he was single? Every woman I can recall, as far as I know, has been very upfront about not being single. That said, it is very possible some painted a worse picture about their marriage and significant other than was the case.

      So, this person couldn’t keep his hands off himself while you thought you were just being platonic? You mean he was perving on you, without you knowing it? That’s sort of creepy, no?

      I agree – not only some, most of the most arousing experience have been with those with some reason they shouldn’t be doing what we did.

      The long term, habitual cheaters I’d put in a different category – one I try to stay away from. Conic, habitual cheating suggests to me problems or personality flaws that are perhaps more unpleasant than those of the stage-cheaters, lust cheaters, awakening cheaters, life crisis cheaters, and I’m going to die if I don’t come right cheaters.

      Liked by 2 people

      • Such a wonderful response!

        Well, he had confessed to having an interest in me in both his actions and words. He also confessed to having a girlfriend, but only when I asked when he had taken me to the bedroom for the first time. I already knew he had one, but he didn’t know I knew… or hoped that if I did, not to mention it. He was a very passionate person, and very respectful of my boundaries – never entering them without my permission. From having hugs too extended, to *trying* to end the sexual relationship and being friends… our hands could never stay still. Maybe I was a pervert, and his simple actions were always misread when we were alone together? Hmmm… either way, our fantasies crossed over.

        But, aren’t we all perverts with out own fantasies when it comes to our alone time? No one has to know what races through our minds when we’re just pleasing ourselves.

        At least he wasn’t a chronic cheater… at least I don’t suspect so. Although a very stoic and quiet gentleman, the guilt deep from his soul would seep from his eyes straight into me. There is a personality flaw there that still baffles me to this day. You could tell it was eating him alive… both of us. But funnily enough, he never painted a picture of his girlfriend. To many people, and to me… it was hard to imagine she even existed until we coincidentally met at a bar one day.

        Did we stop? Well… that’s a story for another day 😉

        As for your novel “Dare”, I’ll be more than happy to read it and have a chat. I’m not someone who is overly literate, but I do enjoy expressing ideas. I’ve had a few experiences with infidelity, most I’m not hiding.

        Liked by 1 person

  11. Pingback: Cheating: Issues, Questions & Implications of shifting attitudes towards marital infidelity. | The Sinner Saint Diary

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