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He Wants Me To Try A Position I'm Uncomfortable WIth

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Dear Gay Best Friend,

It’s this guy, I’ll call him “C.D.” He’s from the hood, and one of, if not, the most THUGGISH dudes I know. We dated years ago, actually we were each other’s first. We were together for a couple of years and I must say we tried a lot of things sexually during that time.

After we broke up C.D. went to prison for a long time, longer than five years. When he got out we thought we’d try to see if the spark was still there. We had sex a few times, (protected of course), and everything seemed to be the same as I remembered. However, there was this one thing. The second time we were together C.D. wanted to have anal sex. YUP! My gay-dar went up quick. I refused and asked him, “Where did that come from?” He was like, “Let’s just try something different.” I thought to myself, OMG! He’s GAY!

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I told C.D. that sounds gay to me, and I have never wanted to have anal sex and I’m not willing to try it with him. C.D. then told me that a lot of women like to take it in the butt, and I’m acting like a little girl. I then asked him, “Are you gay?” At first he was angry and said, “Don’t try me like that.” I said, “Well, before you went to prison you never wanted to do anything like that, and now, out of nowhere, you want to have anal sex. I don’t understand.”

C.D. insisted that he just wanted to try something new with me, and that if I didn’t like it, he will stop. He even told me that all he has to do is lubricate himself and everything will be just fine. At that point I was like, “What the hell! He even knows how to lubricate himself?”

I refuse to be involved with C.D. anymore. He still calls from time to time saying I am acting like a little girl because I’m scared to try new things. I think I know the answer, but I would like to hear what you think!

Please help! – He Wants To Put It In My Butt

Dear Ms. He Wants To Put It In My Butt,

Well, damn! I feel like you, why is he pressuring you so hard to do something you clearly are not comfortable with?  And, girl, you did the right thing. You asked all the right questions:

1.) “Where did that come from?”

2.) “Are you gay?”

And, 3.) “Before you went to prison you never wanted to do anything like that, and now, out of nowhere, you want to have anal sex.”

Honey, I am so glad you stopped having sex with him because he clearly is the childish one. How dare he try that old school tactic of peer pressure by saying you are acting like a little girl, and that a lot of women like to take it in the butt? What does that have to do with you? You are not, “a lot of women.” He needs to go sit his THUGGISH behind in the corner and grow up. I am shaking my damn head right now.

Listen up, ladies. In prison it is not uncommon for men to engage in sex with other men. But let me be clear before every man who is in prison, or has been to prison starts writing me letters. NOT EVERY MAN WHO HAS BEEN TO PRISON, OR EVERY MAN IN PRISON ENGAGES IN HOMOSEXUAL SEX. However, I will repeat, it is not uncommon for it to occur. There is this term called, “Gay for stay.” It means a man will only engage in sex with another man while in prison, however, after he leaves prison he will not have sex with another man. He will resume his “heterosexual” life with his girl, or wife, as if nothing ever happened.

Also, some men like anal sex with women because the anus is tighter and they find it more pleasurable. But, if that is all he wants to do with you, then girl, drop him and run. His anal desires are a clear sign of his sexuality.

So, Ms. He-Wants-To-Put-It-In-My-Butt, first, let me say I am proud that you used protection. Every woman reading this, please use protection at all times. I don’t care how long you’ve known him. It’s your body, and your temple. Protect it. Now, back to you, Missy, the fact that he didn’t answer your questions with a concise answer, yes, girl, I think he may be hiding something. He is clearly not being forthright with you about some things. So, until then, keep him right where you got him, on the other end of the phone. – Straight From Your Gay Best Friend


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