Cheating XI: How Not to Sleep With Married People

If you have read a bit of this blog, you probably know that I’ve accidentally hooked up with a few married people. Shut-up – don’t clear your throat – how rude.

In this episode of our cheating series, I wish to share my experience in order to help not sleep with the wrong married people, if you every accidentally do.

If you have been reading the Sinner Saint Diary for a while, you may have noticed that there are not a lot of re-occurring roles, for the married women I have written about. There’s a reason why this doesn’t happen, I’ve gotten my heart broken and learned a few lessons.

Not to not sleep with 1: Don’t sleep with a married person if they aren’t separated or at least wrapping up a divorce. If you do, make it a one time event: don’t date them or make it a routine. And for God’s sake, don’t fall in love with them.

Yes, I know, you have no interested nor intention of falling in love with a married person – I’ve been there too; funny thing about nature, when people fuck regularly, love happens.

But, it’s different with this person you’ve been seeing, right? Perhaps because…

“They don’t even love their (husband/wife), they just can’t leave yet because (insert reason here – financial, kids, spouse is sick, weather is bad, etc)

“They have not slept with their spouse in years, it is basically a roommate situation…”

“We knew it from the moment we met, we are soul mates and we are meant to be, their marriage is just a temporary obstacle on our road to true love bliss…”

These reasons are compelling, I know because I have bought in to them too. I could have saved some heartache had I known: if a person is ready, able and open –  to giving their heart to you or anyone other than their spouse, they would be gone or in the process of leaving.

Maybe they love you, but if they are not determined to end their marriage, there is likely a reason why – and the same reason will prevent their feelings from outlasting the initial infatuation.

BUT: Should you accidentally sleep with them once, good chance it will be really really great! Unless, they stray from their marriage often – which brings us to the next type of married person not to sleep with.

“But, they have an open marriage, sort of, so what’s the harm? They’re just looking for sex and so am I.”

Who to Not to sleep with 2: Are you looking for a disease? Or, shallow encounters that make you feel like you just used a human being as a masturbation device? or, them you?

If the person and their spouse are both into polyamory or whatever the fuck, perhaps it is better – but then it’s not really cheating; however, if the person is cheating with a variety of people, behind their spouses back, is that what you are looking for? someone dishonest, cheap and unavailable?

reader: Fuck this blog! Like I really need more negativity or lectures about things I shouldn’t be doing. #not, #overit, #lickmeDontpreachme

I think I will unfollow — this bullshit is bringing me down!

Hold on a damn second, I’m not finished, so calm the fuck down. And keep reading.

… Are we calm?

Um, Why are you touching yourself there?

Okay, where was I? Yes, was getting to the “how to not sleep with the right married people section,” happy?

Who is better to not sleep with: The Beluga of married persons to hookup with, are those undergoing a temporary separation: You’ve probably heard me comment on this before – for good reason, there’s only one reason for the “temporary separation” … actually there are two – and both are good news for you:

1. The married person wants to fuck someone else (you) so bad, they incurred the expense and went through the drama to  move out of their damn home.

2. They were not getting any “on the side” before the separation, and won’t be getting any when the separations ends – or else they would not have to move out to “separate.” 

For anyone fooling themselves, who thinks a temporary separation is not so the married person can screw their brains out for a short time without having to account for it, you must be the spouse of one, and it’s better you know the truth.

There is the same danger of falling in love with the separated married person – don’t do it. They are probably even less likely to leave their marriage for you. They’ll rock your world and wreck you – all in a few months time – and by the time you come back to, they’ll be back with their spouse and all but forgotten you.

It is one of those laws of marital nature, if they go through all the trouble of a temporary separation, they are strongly committed. And, they are doing it because they want to fuck, Period!

They will never admit it and will likely take what you do with them to their grave, while their spouse thinks they were reading self help books and focusing on “getting healthy.” 

And now for the very worst and very best married person you should not sleep with…

Worst person to not sleep with: While you avoid sleeping with married people, avoid double the married person who’s been living on their own for any significant amount of time and no divorce papers have been signed.

This situation comes with the most risk and the least reward. There is some reason why divorce still has not happened; it must be a strong reason, or it would have!- How many happy, safe reasons can you think of – as to why a person would live alone for a long time without divorce?

Exactly, it’s creepy. Besides, they’ve had their freedom for a while, and getting a slice is no big thing; they have already been through their fucking-like-a-rabid-teenage-Rabbit-phase.

Perhaps they want your help to extricate them from their abusive husband Guido? or, their borderline psycho wife Haterknifeloveress, how happy would that fun be?

Very Best Person to not ever sleep with: We will end up on an up note and talk about the very best married person to accidentally sleep with…

But first!

I just remembered…

Another consideration: This is a caveat to the best option: While the penultimate accident to fall upon, can be with a person who’s ink is still fresh on the divorce papers – if they were not in favor of ending their marriage, especially if they were cheated on, prepare for tears in place or orgasms.

Why you ask?

Think back to relationships you have ended and those who have ended you. Were you not over the one’s you ended much faster? And, when you’ve been let go, did it not sort of make you want them even more? Their mind will be on them and they don’t want to fuck, if they do it’s stick it to their ex.

But with the non-jilted spouse who just wants out…

Did you ever go to disneyland as a child? Remember the anticipation in the car when the first ride had been spotted? Or, remember what the last hour of class before summer vacation used to feel like – how it seemed to last an eternity? All the energy you felt – perhaps a fog of euphoria – when you  broke free and the limitlessness and freedom of summer began?

Fair enough, you might get the dirtier sex from the separated spouse or the one trapped for life in a sexless marriage. But, you and the the almost unchained, will have hopeful, laughing sex.. and they will soon be available if you accidentally fall head over heals.


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

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Well we have it: 100% unanimous reader vote as to which book to finish up next.

I believe this is the first unanimous reader poll (which received more than a few responses) that I’ve ever conducted.  Was it the ass licking part? LOL, hey, that would be reason enough to get my vote!

I’d planned on needing to give the Which shall I finish up first? poll more time time than this, but given that literally, exactly, completely 100% of the respondents voted in favor of  The Roommates, the directive is clear. 

(BTW, damn good choice, the story is arguably the hottest and most interesting I have to tell)

Thank you all for helping me me find direction with this.

Next up for publication:

The roommates: Renting a room in a condo, Living with Judy and Jayme

This true story started when I moved back to LA for a job and needed a place to live in a hurry. I found a place through Craig’s list. It was a 3 bedroom, two story, two bath condo that two girls were living in. One of the girls, Judy, owned the condo, her parents helped her buy it the year before, and she needed to rent out the third room in order to afford the payments.

The other tenant, Jayme, was the daughter of friends of Judy’s parents. (so, sort of a friend). She was spending a lot of nights with her boyfriend, and Judy was looking for another tenant, in case Jayme moved out to live with her boyfriend.

My time living with these two lasted just over eleven months, but was unforgettable.  Things started getting interesting when the owner Jenny met a guy and started having him over, unbeknownst to her boyfriend. I could hear her on the other side of my wall.  Eventually, the three of us got entangled, and the story becomes complicated and super hot.

Highlights:

  • Hearing my straight laced landlord, Judy, having sex – and orgasms – with a guy she started having over and cheating with.

  • Seeing Jayme lick Judy’s ass – first time I ever saw a woman lick another in such a way.

Which shall I finish up first? Here are the sexy highlights.

I am about 3/4th done writing the following three books – to be subsequent volumes of The Sinner Saint Diary

I can’t decide which to focus on and finish up first, so I decided to ask for a vote.

Which book shall I finish up first?

Please read the following summaries, and then vote on which I should publish next. Thank you.

Gina – renting bottom floor from wealthy medical student.

True Story about the one year, one month, and two days I rented the first floor apartment, in the huge beach house, from a friend of a friend of my ex girlfriend’s.

Gina was a third year medical school student who’d taken ownership of her wealthy family’s beach house, and I was getting booted out of my girlfriend’s house and needed a cool place to go.

Things were winding down with my girlfriend, (ending), and she stumbled upon an option – a place to go. Interesting things happened while I was living in Gina’s house, my first floor apartment there was more like a luxury spa.

Highlights include:

  • My will power breaks down and I take Gina’s panties from a load of clothes she had drying, and masturbate into them. I find a big toy in Gina’s underwear drawer while trying to return the panties.
  • An unexpected, complicating resolve to several months of sexual tension.
  • Gina has a party, and ex Morgan and other friends from Dare I are there. At the end, Gina and I share some drunken confessions.

 

The roommates: Renting a room in a condo, Living with Judy and Jayme

This true story started when I moved back to LA for a job and needed a place to
live in a hurry. I found a place through Craig’s list. It was a 3 bedroom, two story, two bath condo that two girls were living in. One of the girls, Judy, owned the condo, her parents helped her buy it the year before, and she needed to rent out the third room in order to afford the payments.

The other tenant, Jayme, was the daughter of friends of Judy’s parents. (so, sort of a friend). She was spending a lot of nights with her boyfriend, and Judy was looking for another tenant, in case Jayme moved out to live with her boyfriend.

My time living with these two lasted just over eleven months, but remains unforgettably.  Things started getting interesting when the owner Jenny met a guy and started having him over, unbeknownst to her boyfriend. I could hear her on the other side of my wall.  Eventually, the three of us got entangled, and the story becomes complicated and super hot.

Highlights:

  • Hearing my straight laced landlord, Judy, having sex – and orgasms – with a guy she started having over and cheating with.
  • Seeing Jayme lick Judy’s ass – first time I ever saw a woman lick another like in such a way.

 

Dare 2: Living and being crazy with Morgan.

Morgan and I end up dating – I move in with her for a while. Our relationship was crazy and unique. We continued the dare game, defined our relationship by it even, and wild, hot, craziness ensues.

highlights include:

  • Morgan’s cleaning crew talking in Spanish after I did Morgan’s dare to streak naked in front of them. I knew Spanish and listened over intercom.
  • The massage experiments where Morgan and I conduct a study, and have a contest, around getting happy endings from massages.
  • Paula, from Dare I, staying with us after a big fight with her husband Rick.

 

Cheating 10: Looking for a bit of fun before spilling the beans.

We’ve put our discussion down for some time – and now we resume with this tenth installment of the Sinner Saint Diary Cheating series. (links below)

Throughout the series we’ve looked at some destructive situations, shared some marital tragedies, and while some of these stories are in a way quite sexy, most come at a cost.

The Original topic for this installment was be, “Do you spill the beans or not, when you think you find out that your friend’s significant other is cheating: I’ve got a two huge, real life stories about this, that family members and I were caught up in. While the topic has many serious, if not interesting aspects for discussion, it’s not particularly sexy, fun and happy.

So, before we go down deep about cheating, we’re going to ease our way back in and look for a brighter side. I’m wondering where there might be space to play.

“Please, dear lord, I beg you – can we just have a little bit of harmless fun already?’

Looking for fun in grim and unlikely places, is…. Well, not something I’m particularly adverse to.  Let this be our meta-mission: if there are any happy aspects of cheating, perhaps we’ll find them by looking at cheating where it’s left the least damage – or, perhaps where it is no longer cheating at all.

If this sounds a bit familiar, it brings us back to where the series began. On thing this series has made clear, the edges and grey areas are where infidelity – its discussion at least, becomes the most interesting; otherwise, cheating – is fucking – is cheating, sort of – discussion over.

So, here’s the question, again: are there any ways we can play around a bit without feeling too guilty or doing too much damage? If we’re just a tiny bit unfaithful perhaps? Or, by the time we’ve sanitized it to that degree, is it even cheating? Is it worth cheating without any fucking? At what exact point does cheating become just flirting, or more important, where exactly does flirting cross over? I think we should pinpoint that spot and set up camp there.

Are you lost yet? Great, then you have good cause to keep reading. Afterwards,  I might just rename the series to, “The Sinner Saint’s quest to rationalize bad behavior, and reason his way out of hell.” – That is what these topics feel like, but damn it – if that’s a game my subconscious is playing – what can I say, I hope to hell it works.

We’re looking for where cheating is playful and light, so here is a more playful experience that blurred the boundaries without causing catastrophe. I’m interested in your thoughts and comments – would you consider the following situation to be cheating – or just flirting? Also, have you found a boundary? How close to the boundary do you go, or have you gone, and is it a good thing, or wrong?

(I hope you all leave me a really big tip because I had to dig far and deep, go with something nobody has ever known about, to come up with a real life experience on this topic that I’ve not already shared. (p.s. comments and tit flashes are accepted as currency at the SS Diary.)

I’ve never been married, but the following events happened while I was living with a girlfriend – in a monogamous,, semi-long term relationship.

Remembering back, my girlfriend and I, and our friends, did a lot of dancing. It seems strange now, but going to bars or clubs and dancing was routine. Perhaps it still is – I’ve since moved to a different environment… or,  maybe people just don’t dance much when they get old as fossilized sand.

Anyway, if it seems far fetched, trust me – drinking and dancing in packed bars and clubs, with groups of friends on the dance floor, was not fetched far at all, once upon my twenties.

We’d often meet up in groups of up to twenty or so, to drink and dance like this. There was one married couple that my girlfriend and I were particularly fond of.

Now, what happened might  sound subtle or strange, yet, is this not where most of our private or forbidden choices happen? In the dark, unspoken, and known only to ourselves and the one other person in the world who participated?

Both of them were extremely attractive – no doubt my girlfriend would have liked a piece of him. They were also really nice and cool – making them even more attractive. I don’t remember how it started, and to this days we’ve never acknowledged nor spoken a single word about it, but it just kind of evolved: whenever they were around and there was dancing, the wife and I would eventually find close proximity.

We were all big drinkers – no doubt that helped such behavior come about. What I mean is, under the cover of crowd packed dance floors, or dim lit dive bars, we’d always  find our way to the other at some point, dance against each other, and sneak some touches, we were discrete and watchful, acted in-deliberate, yet, the last time I can specifically remember, I actually came in my pants, so, we are not talking about some accidental shoulder grazing here. Not sure if she knew it, that I actually came that time, and I never told her… but, yea, that’s what I mean when I tell you we would dance closely.

This never happened in any other context. There was never any drama nor consequence, and it was really fun. This went on for two years probably. The contact was unquestionably inappropriate, but her and I were the only souls on earth who knew about it.

That is a happy place, right? Perhaps you don’t consider it cheating? When someone has an orgasm, by definition it must be, right?

Please use the comment section liberally, no worries, I bought an endless supply. What is your story? What is your little naughty thing you do that no other soul on earth knows about, that keeps your desire rolling?


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

Should There be Doctors for Orgasms & other Questions About Sex

If a person hires an escort (prostitute) should they get their money back if they don’t orgasm?

If they cheat and the sex is bad, should they feel cheated?

If their partner gets off watching them do it, should they be blamed for doing it?

Should there be doctors and clinics that treat ailments with orgasms?

Should politicians have to have at least one debate in the nude?

If someone is working on their roof and watching a neighbor sunbath – out in the open but in their own backyard, who’s fault is it?

If you slept with them first, is it really cheating if you hookup with them again, or is it the the person their with now who cheated you?

If you’ve already done it once, is it twice as bad or no worse to do it again?

Would you choose tell your partner about all of your past sexual experiences with others if you could know everything about your partner’s past encounters?

Are you more likely to not tell your partner because it was too good or because you were too bad?