Dear Bossip: He’s The Perfect Guy, But He Wants Me To Top Him In Bed

- By Bossip Staff

Dear Bossip,

I recently started dating after breaking up with my daughter’s father and being single for 3 years.

Because of being a working mom and school, I have turned to online dating. After a few frogs, I met a really nice guy. He really is a gentleman. We’ve been speaking now for about 6 months. He’s 39, never married and no kids. He opens doors, asks about my daughter, and my well-being. He’s supportive, our conversations are great, etc.

I like him, but the one thing that is holding me back from pursuing more with him is I think he’s gay or bisexual.

Now, I don’t hold back and I’ve asked has he ever been with a man or do men turn him on, and he says no. What makes me think he’s into men is when we’ve spoken about being intimate he brings up the subject of him being penetrated!

I’ve looked it up and I see that some men like being “pegged.” But, does that make him gay?! I’ve asked him if he’s been penetrated before and he says no…it’s a fantasy of his to have a woman use a strap-on on him.

I thought I was open-minded sexually, but I have never explored in this arena! Maybe I wouldn’t think like this, but EVERY time we speak about being intimate he goes to the subject of him being penetrated. We talk about other things pertaining to intimacy, but that subject is sure to come up and it really seems to turn him on. He also says that in adult movies 2 men are the one thing that turns him off. We watched an adult video of what he likes and its dominatrix.

At this point, I’m not sure if he just really wants to try it or if he misses having it done. My fear is if he likes it what’s the difference with being penetrated from a man? A lot of what I’ve read about it is once a man tries it he they love it, and they continue to want it done…some have even wanted to feel the “real thing.” Please please give me advice on this subject. – Ms. Very Confused

Dear Ms. Very Confused,

You all and your online dating habits, and the folks you meet. GEESH! What website were you on, Meet-Freaky-Deeky-People dot com.  LMBAO!

Well, apparently you haven’t heard about the craze that some men like being penetrated by women. Yup, they want their women to strap up, lube them, and slide it in while they’re on their backs with their legs up. Or, some men like it doggy style.

Honey, in case you didn’t know, it’s been going on since the beginning of time. Some men like having their prostrate and anal area touched, licked, and prodded. That area is an erogenous zone for men. Gently rub between his legs, or lick anywhere underneath the base of his shaft and you will get him going. Even so far as tossing his salad, or inserting a few fingers. Yup, that will definitely send him over the edge.

So, is your man gay or bisexual because he wants you to strap up and penetrate him? No. That doesn’t make him gay or bisexual. He’s told you that he is not interested in being with men, nor has he ever been with a man.

However, what I do suspect is since you mentioned that he’s into dominatrix, then he is into role reversal. He enjoys submission and pain. Yes, he wants you to top him. He wants to totally submit to a woman and she dominants him in the bed while inflicting pain. And, this is not unusual. Everyone has some fetish they are into be it feet, leather, breasts, women’s shoes, women’s lingerie, or whatever. His fetish is being submissive and you inflicting pain on him. He wants you to dominate him, top him, and he becomes your Bish!

He wants to be told what to do by an aggressive and domineering woman in the bedroom. And, it may be because he’s an A-Type personality in his everyday life, or at work. He may be the man who is always in control, strong, and forceful. But, in the bedroom he wants someone else to take control. He simply wants to submit, and endure the pain. And, what type of pain will give him pleasure at the same time – being penetrated. He gets the best of both worlds.

I wouldn’t be surprised if he wants to be spanked, tied up, gagged, and slapped around by a woman. But, once the action is over in the bedroom, it’s over. He goes back to his life and workplace being the strong, confident, and dominant aggressor. Hell, how you top him, penetrate him and make him totally submissive may give him that extra shot of adrenaline to his ego. And, it stays in the bedroom because what happens in the bedroom doesn’t affect his identity or manhood.

Now, you have to ask yourself if he is someone you want to be involved with, and are you willing to strap up and be the aggressive top who penetrates her man? If it makes you uncomfortable, and it is something you don’t see yourself doing, then don’t do it. Don’t do anything you do not want to, or feel uncomfortable doing. You don’t have to succumb to his pressure or manipulation. Simply end the relationship, and walk away. It can be a bit much for a woman, especially seeing her man with his legs in the air, or, he’s on all fours arching his back with his a** in the air.

However, I am curious to know since you’ve been discussing intimacy with him, and he brings up being penetrated, have you told him what you like, and what you’re into? Have you asked him how will he satisfy you, or pleasure you? If the conversation always leads to him being penetrated, and how you can satisfy him, then he is not interested in pleasing you. You did mention that you talk about other things, but it always leads back to penetration and he gets really excited talking about you doing it to him. If he isn’t telling you how he will please you, or asking what turns you on, and what can he do to make you feel enjoyment or excitement, then, you shouldn’t go any further. You don’t want to get in the bedroom and it’s all about him, and you’re left waiting and hoping he will touch and please you.

Therefore, you’re an adult. Make the best possible choice for you. I do recommend that you ask him if he is into pain and submission. What is it about a woman penetrating him sounds exciting and that he wants to try it? Ask him if he ever thought about a man doing it to him instead? Though, again, I don’t suspect he’s gay or bisexual. I truly feel he’s into dominatrix and submission, and he’s into pain. And, he wants a woman to do these things to him. Let him know your apprehensions, and also ask how will he satisfy and pleasure you. If you don’t like what he’s saying, or if he doesn’t seem compatible to your bedroom tastes, then he is not the man for you. Everything ain’t for everybody. End the relationship, move on, and stay away from Meet-Freaky-Deeky-People dot com. – Terrance Dean

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!

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!


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