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15 Tips on Cheating and Managing Your Mistresses

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tiger woods cheating meme

Recently, someone asked me if “men enjoy being the sideman?” For those of you who are unfamiliar, the “sideman” refers to a man who plays the side-role to a woman he knows is in a committed relationship. His equal of the opposite sex is usually referred to as the “sidechick.”

My answer: yes and no.

Most men are fine playing the sideman because it is usually a relationship dynamic many men are striving to achieve anyway. All benefits and no responsibility? Sign men up!

Let’s face it, the role of most sidemen is sexual, usually strictly. Frankly, a number of men spend their entire lives seeking out sex-based relationship and some men will even exit a relationship if they are forced to provide a woman with more than just the promise of good sex and good times into infinity and beyond. However, as with most rules, there are exceptions.

Some men, like some women, will desire more than a sex-based relationship and in their selfish pursuits, they may ruin both your side-relationship and your main-relationship if they want and/or think there is an opportunity for more. This brings us to the premise of today’s post.

We all know cheating is wrong, but since cheating still occurs, if you’re going to be bad, you might as well be good at it. In fact, one relationship expert – term used loosely – has even advocated that the key to a happy relationship is to let your man cheat, and in an interesting turn of events, as women become more and more financially and emotionally independent from men, more and more women are unfaithful.

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I was lamenting how bad a number of celebrities are at cheating and how they are caught in the most ignorant, disrespectful ways. It is one thing to cheat; it is another to simultaneously make your wife/husband look like an idiot in front of the entire world during the process. My complaints did not fall on deaf ears. Someone (who asked to remain nameless for obvious reasons) shared a post with me addressing this exact issue titled, 15 Easy Steps to Managing Your Mistress. While geared towards men, these tips can easily apply to women as well. Below are five of the 15 tips in no particular order.

15. No matter how much she looks back at it or how good she rides it, never under any circumstance have unprotected sex. Women lie a lot. Of course she told you that she’s on the pill.

14. When with your mistress always pay in cash, never use company credit cards, and always burn the receipts after.

8. Know that throughout this experience you run the risk of getting caught. Choose your mistress wisely. You want a woman you can trust to not go ballistic when you have to let her go.

7. Conduct yourself as a gentleman, always be honest. Make it very clear from day one that you have no intentions to ever leave your current wife.

6. Your impromptu fling should never take priority in your schedule. Let the rendezvous be spontaneous or in between work shifts.

4. Say adios to all your social media, this means no Facebook, Twitter, or Instagram. If you want to play in the big leagues you’re going to have to leave these childish games behind.

3. Know that the cyberspace is not your friend. Under no circumstance should you send emails. Emails are forever so are texts but take your chances with texts.

You can check out the complete list by clicking here.

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1) What is your favorite or least favorite tip from the list? 2) What additional tips would you offer the monogamously impaired? 3) If you would otherwise never find out, would you still want your husband/wife to admit they were unfaithful?

Comment(13)

  1. Use cash…i recently had a friend get caught up this way on V-day (purchased something from the jewelery store but it wasnt for his girl) smh. My favorite two that i tell people often is no one night stands (KNOW who you are sleeping with) and never cheat with a person who has less to lose than you do. (if you're married with 2 kids dont sleep with a woman that is single or only has a bf..equal or better) that way if they tell then you both go down.

  2. “Be good or be good at it” – Weezy

    #7 is key, most of the time sidechicks get outta pocket is because THEY was lied to, don’t tell her you’re gonna be with her, don’t lead her believe there’s anything going on besides enjoying each other’s company. #6 has potential to be messy, spontaneity works but still be half a step ahead. Honestly the smartest thing is to get as far away from home as you can, be nowhere anyone can ever catch you slipping.

  3. the sad thing is, people wanna play but can't play the game right. You make sense with a lot of your tips, but I think at the end of it all, be real with the mistress/side chick. If you're in a relationship let them know whats the deal. Let them decide if they still wanna roll with you or not. And they'll respect you more because you were honest and upfront about your situation, so if they see you with your woman chances are there won't be a scene made. Also I have told dudes in the past if you're gonna screw around don't treat the side woman like she's yours. You know doing things for her that you would do for YOUR woman. You'll give her that sense of entitlement and it's all down hill from there
    My recent post WTF Am I Listening To?! – 10 Dumbest Rap Songs Ever Made

  4. I love the one about social media. That gets cheaters and soon to be cheaters in all sorts of trouble. I would erase all texts when you received them just in case your wife/girlfriends happens to go through your phone. If you use condoms with your side chick and not your main only buy them when you are on your way there and buy the three pack. Do not come home with condoms because that will jack you up. The reason is there shouldn't be any reason why you have condoms on you when you leave or enter the house, unless they are in a plastic grocery bag so you can re up the stash. If you email erase your emails and always log out your inbox. Have your own phone line and own bill so she can't check the call log. If you are going to lie practice that lie lol Do not go straight off the dome because some men are horrible liars! lol Those are some tips on how to successfully creep. I hope my future man doesn't see this!
    My recent post Children are our future part 2

  5. It doesn’t matter what year it is. The only reason why cheating is as prevalent as it is, is because of articles like this. Not to mention the people who surround themselves with those who think alike. If the inevitable possibilities of disease were talked about or the demise of a relationship you don’t want to leave, people would rather think twice about indulging in such reckless behavior. I don’t understand why people glorify cheating when the risk is much greater than the reward. What is exciting about possibly getting exposed to herpes which no condom protects you from? Or the more then likely possibility that the condom will break during one of these sexcapades and now your exposed to hepatitis c or the worst HIV? What’s fun about any of that? What kind of person are YOU when you can continuously put yourself at risk and not give a damn about the outcome? I’ll tell you…. A beast. Everybody is out here beastin’ cause it’s the fun popular thing to do. We aren’t even talking about the loved ones who have to come to your aid after you confide in them what your reckless behavior has done to you. Forget what everybody else is saying and stop lying to yourself. It’s never a one night stand. When sex occurs feelings will get involved by one or both parties. The truth always gets told, lies are always found out, and what you have done in the dark will always come to light. If more people shunned this type of behavior and told the truth to the person considering cheating it would less likely happen or wouldn’t be such an easy topic to discuss. Nothing good comes from cheating and the cheater ends up hurting the most. Those are facts. Who in their right mind wants that.

    1. If it was an article that seriously spoke about the dangers of cheating and it's aftermath then I would be with you 1,000 percent. I think in this one it's more a light and airy post. I do not believe anyone thinks that it is truly a positive thing to do in a relationship or to participate in.
      My recent post Children are our future part 2

  6. I'm not too sure about the being spontaneous part. I mean what if your side person is dating other people (smanging) you aren't aware of? Cause, technically, you aren't in a committed relationhip with that person.

  7. I think its best to be open with your side kick and very true about carefully choosing your partner in crime. Some women, the minority (emphasised) do not want a man to leave his wife or get married to them. That would be insane, getting married to a man who cheats on his wife? How stupid is that? Some of them are in it for the fun of it and would happily avoid the missus finding out thus avoiding all the drama. (I am a woman, if you were wondering)

  8. My boyfriend and I were happy as far as I could tell and I never thought that we would break up. When his cousin died in a tragic car accident he went back to Philippine for a week to be with his family. I could not go because I was in the middle of entertaining out of town clients for work. He did not seem to be upset that I could not go so I let him be. The next thing that I know, he reconnected with an old friend from high school that he had a crush on years ago and they started to have an affair! I had no clue what was going on until a month after he came back from Philippine.He proceeded to see both her and I until I caught him testing her one night. I confronted him and he told me the truth about what happened. We broke up and went our separate ways. Neither of us fought for our relationship. I was angry and decided not to be upset about it and just keep it moving. Then after about a month of not speaking to him I became sad. I wanted him to tell me that he wanted to be with me and not her. I contacted prophetjakula for a love spell and he totally helped me! he was able to get him to miss me to where he wanted to get back together again. He had a lot of regrets and felt bad for not fighting to keep me and for cheating in general. He values our relationship so much more now and we are together now! You can also get your lover back with the help of prophetjakula contact him through [email protected]

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