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Dear Bossip,

This is not a PG-13 conversation. Nitty-Gritty: I need the advice of a gay man.

Does a man’s desire for butt play mean that he’s gay or does gay require the desire to be with other men? If a man wants to be poked, does it matter whether a man or woman does the poking? I’m fully aware of the pleasure of prostate stimulation and the abundance of resources that encourage women in heterosexual relationships to “go back there.” I need some raw truth!

My issue: I’m 30ish, divorced 7 years and have no children. Because I married my childhood sweetheart and have an old-fashioned view of relationships and a lengthy requirement list, I don’t have extensive dating experience. Yes, I’m in a drought, but I’m not pressed for a relationship. I want what I want, no exceptions.

From a small child, I was around many gay and bisexual men who hid their truths because of religion and their wives. I fine-tuned my gaydar long ago, but I think it needs an upgrade.

A few years ago, I met “The Geek,” who’s a divorced, single father of five and seems to be the perfect man (handsome by all standards, fun-loving personality, multiple successful careers, heavy community involvement, not an ounce of femininity, etc.). We spent 6 months getting acquainted over the phone and in group settings before beginning to spend time alone. Six more months passed and although we spent time, I never considered our outings dates because despite the long stares that everyone around us noted he never expressed his interest in me.

One evening, he picked me up for dinner and he left the glasses, cuff links and “the geek” at home! Although I was impressed that his “sexy” had multiplied times ten million, I found it odd that he appeared so completely different. His reserved demeanor was replaced with an irresistible and sophisticated swagger. He spent the entire evening explaining why he had to have me in his life and after 4 Long Islands, he had me!

He is an amazing lover and I have no doubt that he loves the female anatomy. I had been celibate for over 2 years at the time and wasn’t open to continue a sexual relationship based on one night that I categorized as a blessed mistake.

We continued to build ‘something’ that neither of us ever labeled a relationship, but we bonded intensely. After months of the conflict that came from his trying to balance a respect for my wishes and wanting sex (we only made magic once), I tried to pull away. While lying in bed one night chatting, he shared (in detail) his desire for anal stimulation, both ways. He has many strange sexual fantasies, most of which I’d try at least twice.

I’m a “butt” virgin and although I’ve not said “Never,” I wouldn’t consider it outside of marriage. My concerns about that (and his begging) made me disconnect from him even further. Eventually, I ended all communication. Be clear: I’m not bothered by homosexuality, at all. Bisexuality is something that I don’t really understand. I do believe that one should be honest enough with themselves to live the life that genuinely satisfies their soul.

“The Geek” was a good friend and I missed him. Recently, after a year apart, I contacted him just to make sure that he was well. As if no time had passed, he began urging me to join him in planning our future. According to him, I should be living in his house and pregnant within the next 6 months (NOT!). It’s clear that he truly wants me.

He’s asking that we pick up building a relationship where we left off, sex or not. We have discussed sex and his butt desires. He sticks to the claim that he’s never shared the thought with anyone, has never had his “back” parts touched and is open with me only because he wants to spend the rest of his life with me. Each time he’s mentioned it, he needed reassurance of my confidence.

I’m not a religious woman, but I do have a solid and growing relationship with God and that’s something we have in common. I assume that since he comes from a family full of active Methodist ministers and works in professional sports, his family and work life wouldn’t be supportive if he were gay.

He’s an amazing person and I trust that he’d treat me well. I even trust that he’s been honest with me… about everything except the root of his sexual desires. I can’t decipher whether he’s hiding his true sexuality or if he’s just a freak. It would be a shame for me to miss out on the best man for me, but I have no desire to be a cover for someone living on the down low.

I need some advice before I ask this man to strip, bend over and cough because I know he’ll oblige. – Entering The Backdoor

Dear Ms. Entering The Backdoor,

So, why don’t you just ask him if he’s gay or bisexual. Why not ask him if he has had desires to be with a man, or if he has ever been with a man intimately. Why not ask him where this desire came from and why he feels the need to have his butt played with. He’s so forthright about his desires, therefore, he should be forthright with his truth.

Chile, some of you women are so scared to talk to men, and ask the necessary questions, but you you’ll stay up in their faces letting them say any and every thing to you, and you’ll keep spreading your legs for them. Then, you wonder, “Why did he do this to me?” Or, “I shouldn’t have continued this, and I knew better.” SMDH! If you are uncomfortable with what he says, what he does, and your intuition is telling you to walk away, THEN WALK AWAY DAMNIT!

Girl, look here, I find it strange that out of nowhere, and all of sudden, he wants to engage in butt play, yet, he claims he’s never done it before. (Giving him the side eye.) Then, if he’s never done it before, where did he see it, or why does he want to do it now, especially with you. That just doesn’t add up. Was he watching an adult movie and saw it happening and figured he wanted to try it? Was he reading about it, and he read the rave reviews of men discussing the pleasure they received and he decided he wanted that same pleasure? Or, has he been playing with himself and he enjoyed the pleasure and wondered how it would feel if a woman strapped up and pumped him. Maybe he’s afraid of having a man do it, and figured the next best thing is a woman doing it for him. Who knows, but it is strange and out of the blue. Hell, I’m curious to know what the hell is up! Why now!

Besides, isn’t it odd that he’s willing to risk everything by disclosing this to you, and he put all his confidence in you, then he asks you for your reassurance. Why? Are you a gatekeeper of secrets? Why does he want your reassurance to keep his secret that he wants to have some butt play? Yes, for some men it may be emasculating to have his butt played in, licked, fingered, and plugged. And, if their secret got out about their desires then people would assume they were gay or bisexual despite it being an erogenous zone. But, again, why does he feel he can confide in you about something he claims he’s never done? He is willing to let you play in his butt because he likes you and feels he will spend the rest of his life with you? Girl, come one. Really? You are the chosen one! LMBAO!

You know what, I say go for it. Strap up, sistah! Strap up! Let him bend over, or throw his legs in the air, or get on all fours. You let him get into any of these positions (this will be tell-tale because if he’s in any of these positions, then yes, he’s done this before), and you get the toy and begin to explore in his backside. If he’s telling you to go deeper and harder, then he’s done this before. If he is arching his back and thrusting back on it, and enjoying it way better than you imagined, then he’s done this before. If he’s riding and grinding on that sufrtboard, telling you how good-good it is, then he’s done this before.

Obviously you are intrigued by him and attracted to him. And, I gather it’s more about why you can’t figure him out, especially this heterosexual appearing man who has it all, yet, he has this weird fetish he claims he’s never done. This is bothering you because you can peg a gay or bisexual man, and for some reason you can’t seem to peg him. It bothers you that you can’t seem to pinpoint him in your box of categories. You enjoyed that one night with him, and you want some more, but you’re not willing to risk it because what if he turns out to be gay or bisexual, then you are not willing to sign up as his beard. You’re not willing to join that party.

Yet, the mystery is killing you inside. You so desperately want to know, and you want to find out what’s going on with him.

Look, I get that you may be new to the dating game, and you have a list of requirements for the next guy you plan to marry. It’s obvious that you both like one another. He wants you, and you want him. You enjoy each other’s company. However, if after a year apart, and after him disclosing his desire for butt play turned you off, then why did you call him up? Why check in on him? Most folks when they walk away from someone, especially once someone turns them off, they do not return to pick up where they left off. You move on with your life and keep it moving.

You opened the door, and now Pandora’s Box is sitting perched on your doorstep intriguing you to open her. If you open this box you will not be able to re-close it. You are going to unveil some things you may not be ready for. And, if his desires for butt play, or questions about his sexuality are lurking in your mind, then stay away.

I don’t know if he’s gay or bisexual. I, like you, find it odd that out of the blue he wants to experience butt play now. So, again, you have to ask him the questions and get him to reveal to you why he wants to do this all of a sudden. Where did this idea arise, and why does he want to do it with you. Why does he feel so comfortable revealing this to you, and what happens if you don’t continue a relationship, but end up as friends? You can’t ensure him of a commitment, or that you will end up together. Who knows what will happen. But, one thing you can be sure of is that you are unsure about him, and your uncertainty is there for a reason.

If you are uncomfortable, and your mind is unsettled, then walk away, and move on with your life. There is a reason why your intuition is telling you to stay away. There is a reason that red blinking light is giving you a warning sign. – Terrance Dean

Hey Bossip Fam, what do you think?

Share your opinions and thoughts below!

Also, e-mail all your questions Terrance Deanloveandrelationships@bossip.com

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!

     

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! – See more at: http://bossip.com/938581/dear-bossip-i-simply-want-a-fwb-situation-however-they-are-catching-feelings-im-not-sure-if-its-me/#sthash.q64KWEdt.dpuf
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