To cheat or not to cheat

by Molly Moore
screen shot of tweets

Today I read a post on Kendra Hollidays blog, The Beautiful Kind, about a threesome that she and her partner recently experienced. The threesome in question was an FMF with Kendra, her partner Mathew and an old friend of Kendra’s from high-school, who is referred to as Andromeda. So far so good, but Andromeda is married to someone else who is unaware of what is going on. The post does deal very briefly with why Andromeda was motivated to explore this opportunity but it doesn’t talk about how Matthew or Kendra felt about that situation. In fact the majority of the writing is about the actual event itself which, regardless of anyone’s marital status or possible moral dilemmas sounded like a truly hot and pleasurable experience for all those involved.

However, it is in the commenting section of this post where things get a little more difficult as some people have accused Kendra and her partner of being hypocritical. Just to give some context to this, as well as writing her blog, Kendra is one of the founders of Sex Positive St Louis “an outreach and education organization.” and she also works as a Relationship and Sexuality consultant. Much of her work, writing and teaching, advocates openness and honesty within relationships and yet it would appear in this post that she is not only condoning but is complicit in Andromeda’s cheating. It is therefore easy to see why people have left some of the comments that they have.

For me though I don’t think it is as clear cut as that. People cheat for a myriad of different reasons, some of which are simple and some of which are hugely complex and challenging. We don’t really know anything about Andromeda’s marriage or life situation from this post, all we do know is that she decided this was something she wanted to do and something she wanted to do with Kendra and Matthew. From what I know of Kendra, which is from being a regular reader of her blog for the last 4/5 years (sadly we have yet to meet in person but I live in hope that it will happen one day) I am fairly confident that this was not something she decided to do on a whim and that she would have taken a great deal of time to know and understand her friend before embarking on this course of action.

The post wasn’t written to invite moral judgement on any of the people, it was written to share an experience that Kendra and Matthew had, because that is what Kendra does; she shares her life in a frank, honest and open manner. The good bits, the bad bits and all the bits in between. For me, not writing about this experience would have been the hypocritical thing to do. That would be saying “I did something that might challenge people’s views of me and so I will not be tell them about it.” In fact what she has done is present the situation in a fairly matter of fact and way and said, for right or wrong, I did this, I don’t regret it, in fact I am happy I did it. Now that is an honesty that all too many people shy away from.

Don’t get me wrong, I think the situation is complicated and yes I think there is huge potential for the people involved, particularly Andromeda and her husband to be very hurt but life is complicated. It is not always easy and nice and sometimes we make decisions that seems to be out of character or that challenge peoples view of us, but heaping shame on people for that and not taking the time to try to understand seems wrong to me.

Since reading the post I saw these tweets from Kendra and so in the spirit of honesty and openness here are my answers.

screen shot of tweetsHave you ever cheated?

Yes I have. I am not proud of it, I didn’t get a kick out of the cheating aspect of it what I did at all. I did get a kick out of the sex though and I did enjoy those times I had with other people. I am sorry that doing it hurt someone but I am not sorry I did it. I found myself in a place where at the time it felt like the only option for me and I think if I had never done it then it is possible that I would still be plodding along waiting for my life to start properly, not realising that the only person who could truly make that happen was me.

Would I ever cheat?

Despite my answer to the first question my answer to this one is no, I would not, but that is because my life is completely different now. I find myself in a relationship where, although we are mainly monogamous and both happy to be that way, it is not a fixed or rigid thing and so I can’t currently see myself ever needing to cheat. I hope that whatever the future holds for us as a couple we have been through enough together and built our relationship in such a way that cheating just would never need to feature for either of us.

Would you get with someone who was cheating?

I have done in the past. At the time I saw it as being their decision to make not mine. I knew the deal but the cheating was theirs. I didn’t make them do it, they were responsible for their actions within the relationship they had. Now though I think I would be more cautious. With life experiences comes knowledge I guess and being married to someone who was cheated on for many years and hearing firsthand the pain, distress and long term effects that has had on that person has altered my view. Betrayal is horrible. It can have deep and long lasting repercussions on peoples self esteem, self worth, body consciousness etc and their ability to trust and form relationships in the future. I think having seen this would mean that I would be very reluctant to be with someone who I thought was cheating. In fact a while back I decided against pursuing a relationship with another woman when I realised that her partner was completely in the dark about what she was doing.

Does seeing a sex worker count as cheating/Does going to a strip club?

For me, neither of theseΒ  things are cheating. I think the first one is clearly a sign that something might be wrong, but for many people choosing this route is how they manage to deal with a mismatch with regards to sex in their relationship. The second one is definitely not cheating. For me that would be like saying reading a sexy book and having a fantasy about one of the characters is cheating on your partner, or for that matter watching porn.

What these last two questions do really highlight for me though is, that this subject is complicated and that I think having a black and white approach to what is and is not cheating only sets boundaries that many people find impossible to keep and often makes it very hard for people to then talk to their partner in an open way about their desires.

Sadly there is still too much teaching that monogamy is the ‘one true way’. Everywhere you go it is held up as the perfect ideal, the thing to reach and strive for. In movies, in books and particularly within the mainstream media. Don’t get me wrong I am definitely not knocking monogamy but what I am knocking is the idea that it is the right way. The only right way of having a relationship with another person(people) is the way that works for the people involved. Monogamy is not the gold star of relationships it is just one way and it only works if everyone on board is, well quite frankly, on board. Human desire and sexuality is so diverse and fluid and monogamy often seems to be in direct conflict with that fact. Having this goal, or ideal, often driven by a religious agenda that effectively denies that fact is not helpful. Likewise judging people for their actions when they step outside of those boundaries for whatever reason does nothing to help create a positive and open conversation about other relationship constructs.

I don’t know what will be the outcome of Andromeda’s threesome with Kendra as far as her marriage is concerned but who knows, maybe it will inspire her to try and attempt a conversation with her husband about changing the dynamics of their relationship or maybe she will just carry on being married and treasure the memory of this experience or maybe it will be far more stressful than that and her marriage will come to an end but whatever it is I think that Kendra and Matthew actually gave her a very precious gift by sharing themselves with her without judging her for her actions. They showed her honesty, tenderness, care and maybe they might even have inspired her to try a different way in the future.


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Matthew May 21, 2014 - 9:22 pm

Thank you for your thoughts and taking time to share them. This is a topic that, I think, should be explored much more often. There are many, many unhappy people out there as you know.
For the record, I have been cheated on in the past. I was in a monogamous relationship for ten plus years, and quite happy with those guidelines. However, my life is much different now….I don’t imagine I will ever go back to full time monogamy.

Life is too fluid, as you so said.

Molly Moore May 21, 2014 - 10:02 pm

Hello Matthew, thank you for stopping by and leaving a comment. I completely agree with you that there are too many unhappy people. I used to be one of them. Cheating is not something anyone sets out to do I think but it happens and as I said in my piece creating shame and turning it into a taboo subject is not helpful to anyone.


Modesty Ablaze May 21, 2014 - 9:33 pm

As always you’ve written my would-have-been answers . . . to Kendra’s questions . . . for me, though far more eloquently.
We are all (I mean the royal “all / everyone”) different, yet all very much the same . . . just that some of us are more honest than others. More honest with ourselves that is, if not “shouting it all out aloud” to people whose situations, personalities, relationships etc, may not deem it right or appropriate to hear.
Xxx – K

Mia May 22, 2014 - 12:19 am

Beautifully written piece. For me here the overall message I come away with is acceptance and life and let live.

We are all different and are all in our own individual relationships with their own dynamics, thoughts, feelings and actions. What works for one does not necessarily fit well with another.

Being judgemental does not help anyone but nevertheless many people will judge and close their minds and that is a shame.

This is where I feel we fit well as the voice for sexual positivity and acceptance of the individual’s preferences whether or not they fit with our own ideas and ideals.

Here you have put the point across beautifully!

~Mia~ xx

Penny May 22, 2014 - 1:12 am

I’m really glad you wrote this post Molly. I didn’t see any of the original tweets, but I think Kendra’s and your honesty is extremely important, as it’s definitely a topic people stray away from. I too have cheated and may attempt a post about it all.

Molly Moore May 22, 2014 - 10:17 pm

I hope you do. It is a subject that still seems to carry much shame and so people all too often shy away from talking about it openly


Reply May 22, 2014 - 3:00 am

Your view is fair and balanced and without prejudice!

Jenna May 22, 2014 - 11:55 am

I find your honest exploration of this topic refreshing. So many people equate cheating with a black and white sense of right and wrong, and it’s never that simple. I’m still struggling to shed all the sexuality prejudices and assumptions I’ve been raised on and unfortunately cheating is right up there at the top of the line. Being aware of the assumptions you may fall victim to, being honest and candid, and reaching for a sense of understanding rather than trying to figure out who’s right is the only way to approach this kind of topic – which you’ve demonstrated beautifully.

Kendra Holliday May 22, 2014 - 5:28 pm

Thank you for posting your thoughts on the topic. You’re right – we did not dive into the threesome recklessly. I don’t take responsibility for other people’s relationships. I don’t think I’m a hypocrite.

One of my goals is to leave people better than I found them.

Ideally, everyone is happy and on the same page, but the truth is, many times a thing that makes one person happy causes pain in another person. There is a balance, we all take turns with the highs and lows. Life is full of creation and destruction – it’s how we keep evolving.

John May 22, 2014 - 10:02 pm

I have never cheated, in that I have never had sex with anyone else.

To (one at least) of my friends, I have cheated, because I think about sex with other people, I write and read erotica, and I watch pornography. To them, and their conservatism, that is cheating. I think not, and my wife (obviously) agrees.

I live by the boundaries my wife and I have agreed. I know where the line is, and I have never gone near that line. For that reason I am trusted to go to London/Bristol for Erotica/Eroticon/etc because I have never gone past the line. And if I violated that trust I would lose that freedom.

But a really interesting post! πŸ˜‰

hubman May 22, 2014 - 10:05 pm

I’m a big fan of Dan Savage and I think he makes a great point, though I wish I could remember which of his books I read it in. His basic premise is that many of us are not wired for monogamy and the occasional fling with another, whether it’s consensual or not, could actually be good for the long term health of the primary relationship. Maybe Andromeda had her 3some fun with Kendra and Matthew, satisfied an desire for something different, and is ready now to recommit to her husband.

Molly Moore May 22, 2014 - 10:16 pm

I love Dan Savage too and I completely agree with him about this subject. I nearly linked to a clip of him talking it actually at the end of this post, but sadly it would not load properly.


Marie Rebelle May 24, 2014 - 6:53 pm

A lovely message and something that so many people should read, because yes, monogamy is not the answer to everything. What is the answer is that each couple should be able to decide how they want to live their lives, what makes them happy. And yes, each individual should be able to decide this for himself/herself too. I would not want to live my life with Master T anyway else than from what we have now, where we allow others into our relationship, where I can watch how another woman sucks Him or when He watches how another man kisses or fucks me. We are happy like this and I don’t care one bit what people who swear with monogamy thinks about it.

Like I said, a lovely post!

Rebel xox

cammiesonthefloor May 25, 2014 - 12:28 am

Such a great post, and the others have already said what I was going to say.

Harper Eliot May 27, 2014 - 12:42 pm

This is such a thoughtful and honest piece. I always think, from any one person’s perspective, that cheating happens in three directions: your partner can cheat on you, you can cheat on your partner, or you can be part of someone’s decision to cheat on his/her own partner. In all three I think you have to own your part in that, and I think thoughtfulness and mindfulness are paramount. But ultimately, I believe human beings should have the freedom to make their own choices. In an ideal world I believe those choices ought to be very well informed, but at the end of the day, it is our own choice to decide.

What I would really like to see change, when it comes to cheating, is the reaction. I loathe that we live in a world where so often cheating = breaking up. I don’t think this should be the default. The default should be conversation and consideration; maybe that will end in a break-up anyway, but, as you say, life is complicated. Living by expectations is endlessly sad.

Sex Toys June 3, 2014 - 1:10 am

My partner and I recently had a 3 some with an escort and we can really relate to this post. We don’t feel that it’s cheating.. but is sex with an escort cheating if you’re 1 on 1?

Molly Moore June 3, 2014 - 3:18 pm

I think the answer to that is.. it all depends on the people involved. For some people it would be and for others it would not. Sadly I think for many people talking openly about things like this with their partner can be very challenging and as I said in my post monogamy is still held up by society as the ‘right’ way to be which often leads to situations where couples feel that any kind of sexual interaction with another person, who is not their partner, is some sort of major taboo.


CavaSupernova June 17, 2014 - 3:39 pm

Fascinating post on a complex subject. I’ve been in threesomes when the third (a male) was married; this was many years ago. It was a crazy time of my life and I had a horrible, skewed perspective on just about everything. I’d never do it now, unless it’s with married people who are married to each other.


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