Dear Bossip: My Fiance’s Brother Is Bribing Me To Sleep With Him...

Dear Bossip: My Fiance’s Brother Is Bribing Me To Sleep With Him & I’m Tired



Black man angry

Dear Bossip,

I’m a well-educated man who is currently the manager at the job I’m working. I have a beautiful fiancé whom I love dearly.

We’ve been together for 6 long years and we have been living together for two years. I proposed to her 6 months ago.

The dilemma I’m having here is that I made a mistake 9 months ago that could threaten our future. One day, while she was working her very flamboyant brother stopped by, which he does on the regular. He and I were joking when I asked him for fellatio, in a joking manner. He said if he did it that I would be whipped and I told him to prove it. I’ve never been with a guy and to me this was nothing more than harmless conversation.

Well, he gave me oral satisfaction and I ended up having sex with him. Our affair went on for two months before I ended it.

Seven months ago I went out for drinks with my girlfriend’s brothers, (one came to visit from out of town and the other one I had an affair with). When I popped the ring out and said that I’m going to ask their sister to be my misses, they both seemed genuinely happy for me.

About a week later, while I was home, my girlfriend’s brother came over angrily. He went into this spiel about how I used him and how he loved me and how I loved his sister more. I told him I’m sorry for that affair and that I’m not gay and it should have never went that far. I apologized for getting his feelings involved, but I told him his sister is the love of my life and that I couldn’t imagine my life with no one other than her. That really ticked him off and he threatened that if I proposed to her that he would let everyone know about our little fling.

I was in complete shambles because he was trying to rain on my parade and gave me a very unfair ultimatum. I didn’t want him to expose our dirty little secret, which I regretted and still regret. I decided to take a gamble and propose to my girlfriend. My thing is, her brother has been livid ever since and has been bribing me into having sex with him or he’ll blast our affair. Every chance he finds that we can be alone he’ll come perform oral sex on me and in return I’d have to have sex with him, but I’m tired of living this lie.

I’m tired of having to do things I hate doing in order to keep a secret in the dark that would hurt and hinder my relationship. Terrance, I’m truly tired and I just want to come clean to my fiancé, but I’m so afraid to lose her. I don’t even know how to fix my lips and begin to tell her what I’ve done and is still doing. I don’t want to be involved with her brother anymore. I’m ready to get married and start a family. What advice can you give me? – The Sad Truth

Dear Mr. The Sad Truth,

Basically you’re cheating on your fiancé with her brother, and you’re having a gay affair, but claim that you’re not gay. And, you feel he is bribing you into having sex with him so that he won’t reveal your affair and end your relationship with the woman you claim is the love of your life.

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You are a mother***ng low down dirty ass bastard! And, so is her scum of the earth gutter ass trifling no good brother.

You have a lot of gall and nerve to sit up here and say that you love your fiancé, and you want to marry her, but you’re sleeping with her brother and want to blame it on some bull-ish bribe her brother is holding over your head. He’s bluffing. He’s weak. He isn’t going to tell anyone or do –ish.

What you’re doing to her is so wrong on so many levels. It’s not fair that she is in the dark about this, especially from the two men in her life that she loves the most. It’s unfair to her that you would do this to her with her own brother. And, it’s unfair that you would be sleeping with another man. She doesn’t deserve this. You’re wrong, and you can’t possibly think she would want to still marry you after learning the truth.

But, let me back up for a minute. You claim you jokingly asked him for fellatio, and once he obliged you ended up having a two month sexual affair with him. Hmmm, I don’t know any heterosexual man who jokes with a gay man about receiving fellatio, especially if he’s never been with a guy, and he is not gay himself. So, why were you joking with him about it in the first place? Why joke about something like that, and then follow through if you’re not gay, and you’ve never been with a man? Were you curious? Were you horny and wanted some head, and figured this would be your experiment? But, again, what heterosexual man would joke about something like this and he’s not gay?

And, why would you continue a two month affair if you’re not gay? You see, if you’re not gay, then it wouldn’t have continued that long. As a matter of fact, receiving fellatio would not lead to sex. How did the joke about fellatio lead to sex? That wasn’t the joke. You had sex with another man, and you proceeded to do so. The affair you had with her brother for two months was because you wanted to do it. He wasn’t bribing you during those two months, therefore, you were under no obligation to continue the affair. But, you did. Which leads me to believe that you are either gay, or bisexual, and you’re in denial about your sexuality. You’re lying to yourself. You’re lying to your fiancé. And, you and her brother are both some trifling dirty dogs for doing this to her.

Now, you have regrets for getting his feelings involved. And, you regret sleeping with him because you want to marry his sister, and live happily ever after. Uhm, sir, you ruined that. You destroyed that from ever being a possibility. The moment you slipped your penis in her brother’s mouth, and the moment you entered him, you no longer could allow yourself to be called her man, her fiancé, her lover, and future husband. I don’t even know why you proceeded to ask her to marry you. You’ve made the situation worse. You are sleeping with her own brother. HER BROTHER! That is truly low down, and just some deceitful and ratchet –ish!


But, hold up! Her brother comes to your house, the home you share with your fiancé, his sister’s home, and you have sex with him in your home that you share with her? WOW! You’re the worst! And, I can’t!

Now, you’re tired of being bribed into having sex with him. You’re tired of sleeping with him so that he won’t reveal your secret. And, you don’t want to live this lie anymore and you want to come clean to your fiancé. You say that you’re in shambles, and he’s raining on your parade, and he’s given you an unfair ultimatum? Really? Really, bruh! He’s given you an unfair ultimatum? He’s raining on your parade? Did you forget that you are sleeping with her brother? Did you forget that you knowingly had sex with him for two months? Did you forget that you are cheating on your fiancé, and that you have not considered her in this equation? You don’t care about her. You don’t love her. How could you fix your mouth to say you want to marry this woman and you’re sleeping with her own brother?

Well, since you’re so tired, and you feel like Mr. Do Right, and Mr. Feel Guilty, well, it’s time you come clean. Tell her. Be honest and upfront. Beat him to the punch and tell her that you’ve been sleeping with her brother, and despite the fact that you’re not gay, and you have no desire to be with men, you have continued this affair with her brother because you didn’t want him to reveal it to any and everyone. Tell her that you initially slept with him for two months because you enjoyed it, but stopped it because, well, what was your reason for stopping it? You never shared why you ended the affair after two month. (Sips tea)

If you don’t tell her, and you keep sleeping with her brother, then this will continue into your marriage. And, I don’t understand how you could even think about walking down the aisle knowing you’re sleeping with her brother. But, just know that this will continue, and you will then be sleeping with your wife and her brother.

If you end the affair, again, and her brother decides to tell her and everyone else that you and he have been sleeping together just know it will destroy your fiancé, your relationship, her family, and it will be a huge mess. You can forget about any type of marriage, or even having a relationship with her. It will be over. But, as I stated before, I don’t think he has the balls, gall, or nerve to tell. He is bluffing, and I would call him on his bluff. He is weak, and trifling. He’s manipulating you because he knows you have more to lose than he does. So, this bribe he is doing is his way to get you to continue sleeping with him. But, again, he won’t tell because he wouldn’t want to destroy his sister, and he knows the repercussions it will have on him and his relationship with his family as well.

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If you decide to end the affair, and you decide to tell your fiancé what is going on, just know your relationship will end. This will destroy her. She will be embarrassed. She will feel deceived and manipulated. She will not trust you, and will leave you. And, it will create a huge riff between her and her brother. You can try and explain what happened, how it got this far, and why you continued to do it. You can even try and explain that you’re not gay, and you don’t want to be with a man, but with her. She won’t believe, I don’t believe you, and no one will believe you.

Any of these scenarios can happen, and I’m sure there are others, but notice that in each of them you’ve created this drama. It is because of you that this is happening. And, you are responsible for whatever happens, and how it ends. But, please know that you are the catalyst for this, and you have to take responsibility for it.

Lastly, you can sit up here and claim you’re not gay. You’re not into men. You don’t desire to sleep with men. However, you consciously, knowingly, and willingly carried on a two-month affair with another man. It wasn’t a one-time thing. It lasted two months. Either you’re gay and in denial. Or, you’re bisexual and in denial. Notice that you never explained why you ended it. Was it because you started to develop feelings? Did you stop because you were enjoying it and then you would have to admit that you were either gay or bisexual? Did you feel guilty for what you were doing to your fiancé? Did you feel guilty it was her brother? What if it wasn’t her brother, but some random dude who didn’t know your fiancé, or was related to her, would you have stopped the affair? And, since you’re talking about him bribing you, uhm, sir, he doesn’t have a gun to your head. He is not making you sleep with him. He is throwing a tantrum, and he’s all in his feelings and emotions talking about how you did him wrong. He’s acting like a bish. So, you’re sleeping with him to stop his tantrums, and to make him feel good and that you like him? Again, if you’re not gay, and you’re not into men, no amount of bribing would make you sleep with another man just so that he will keep his mouth shut. – Terrance Dean

Photo source: Shuttershock

Hey Bossip Fam, what do you think? Share your opinions and thoughts below! Also, e-mail all your questions Terrance Dean:  Follow Terrance Dean on Twitter:  @terrancedean and “LIKE” Terrance Dean on Facebook, click HERE!

author terrance dean

Make sure to order my books Mogul: A Novel (Atria Books – June 2011; $15); Hiding In Hip Hop (Atria Books – June 2008); and Straight From Your Gay Best Friend – The Straight Up Truth About Relationships, Love, And Having A Fabulous Life (Agate/Bolden Books – November 2010; $15). They are available in bookstores everywhere, and on Amazon, click HERE!

Mogul  Hiding In Hip-Hop cover  Straight From Your Gay Best Friend


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