Dear Bossip: He’s Definitely Freaky. But Is He Gay?

Hey Bossip. I have a major issue and I could use some advice. I had been seeing this guy since the summer ended last year. He had me on “cloud 9” and I thought I couldn’t have asked for a better man. He has everything, he’s a gentleman, listener, affectionate and FINE!!!

In previous relationships, I tend to jump in the bed to soon so I thought I would take a different path this time around and really get to know this guy. So I told him I wanted to wait a while and he was cool with it, honestly now that I think about it, he was a little to cool. He told me that he was patient, he respected my wishes and he would wait until I’m ready.

Like I said, he had all the works and had me floating. So over the holidays we decided to have sex and let me tell you, he was AMAZING!!! Things were going great until a few weeks ago. We had just came back from a lounge and we were both pretty tipsy. While we were having sex (it was kinda wild) he got up and pulled a box out the back of his drawer and it was a life sized dildo and this man had the nerve to ask me would I pump him with it. I was paralyzed, I couldn’t move. I told him that I wasn’t comfortable doing that and also it seemed a little gay. He tried really hard to convince me that he’s not gay and that he doesn’t feel like his “extremely freaky ways” are suspect!

I haven’t spoken to him since that night and it’s been almost two weeks. In his last message he said that he knows that he may have freaked me out but he really liked what we have and the ball’s in my court and to give him a call when I’m ready to talk. I’m so confused by all of this and too embarrassed to tell my friends and family because he’s been my dream come true for a few months and if I tell them, it’s a wrap. Is he gay or just “extremely freaky” like he says. What do I do? Do I talk to him or let it go?

Wow! If another one of these ” I can’t tell if my man’s gay” scenarios surfaces, it’ll be too soon. This topic is far too frequent! What’s really going on? But moving on. Is he freaky? Sure. Is he gay? Only he knows. Most straight men do NOT want their anal cavity poked, prodded or penetrated, period. However, there are some who are cool with a little bottom play, but a true-to-life penis seems a little too much. There may be a deeper issue behind his wanting to be sexed with a life-sized toy. There could be some history of abuse or molestation that he hasn’t shared with you. He also could have done some time in jail that you don’t know about. Worst case scenario, he’s willingly been with men once or twice, likes the feeling but prefers women. There’s a wealth of circumstances that could potentially contribute to his homosexual tendencies but you won’t know unless he’s willing to share.

If you should decide to talk to him again, you should be good and firm on your position. Are you seeking closure? If so, say everything you need to say, ask all the questions you want to ask and be done with it. No flip-flopping. Do you want to work it out and give it another go? If so, be solid on that, but just know that you can’t say you don’t know what you’re dealing with from this point on.

In total honesty, you should take the time you need to get over the shock of it all. Whatever embarrassment you feel is irrelevant because your friends and family have nothing to do with what transpired between you two. Sort through your feelings and thoughts and calculate your next move from there, but not a moment sooner! Don’t be pressured to talk immediately, or at all for that matter! Take your time, sis! Take your time.

What do you think she should do Bossip Readers?

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