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You’ve got questions? He’s got answers! Need advice?

Send your questions to Terrance:

Dear Gay Best Friend,

I have been wondering about the following for a while now.

At the beginning of our relationship my ex admitted to having had sex with a Transsexual in the past. According to him, he was in a bad place at the time and wondered if he had such bad luck with women because he thought he was gay. Besides, he was being hit on rather regularly by gay men. In his mind he asked himself if they saw something he was simply oblivious to. To cut a long story short, somebody set him up with a Transsexual man and they had an encounter. I never asked the details (top vs. bottom, oral) but I admit it was in the back of my mind and made me question his preference.

At the time he told me about it, I appreciated his honesty and didn’t think anything of it because he assured me that it was a one-time-only encounter which helped him realize that he is definitely straight. I blamed it on him being very open-minded and experimental. However, what made me doubt him was the fact that he had a thing for tranny porn (among other kinds). So if he was turned off by the idea why did he continuously get a kick out of watching Transsexual men having sex with both genders?

Confusing to say the least. Like I said, he is my ex – for other reasons. So the question isn’t an urgent one. However, I’d like to know if having had sex with a Transsexual man could be considered a red flag so I can steer clear of such “experimental” guys in the future.

Thank you in advance, my new gay best friend. – My Ex-Man Was Into Transsexuals

“My Ex Infected Me – I Want To Date But I’m Afraid Of Rejection!”

Dear My Ex-Man Was Into Transsexuals,

Okay, first off, let me explain to everyone what Transsexual is. A transsexual is a person in which the sex-related structures of the brain that define gender identity are exactly opposite of the physical sex organs of the body. Put even more simply, a transsexual is a mind that is literally, physically, trapped in a body of the opposite sex. So, yes, they still have the physical equipment of a man or woman, but a man will feel like he is more of a woman trapped in a man’s body, and vice-versa.

Now, let’s get back to his letter. Juicy!!!

So, let me get this straight, your ex said he was having such bad luck with women because he thought he was gay, and that a plethora of gay men were hitting on him, so he figured he must be gay? Girl, that is not rocket science. Your ex is gay. I mean why would he think he was gay because he was having bad luck with women? That would not be my first train of thought if I was having bad luck in relationships. I would try to figure out why I kept attracting these bad relationships.

But, there is a saying that I live by, “Everyone knows except you.” If everyone suspects you of being gay, and you keep saying you’re not, yet you keep thinking you are and questioning your sexuality, then it’s probably because you haven’t come to terms with yourself. There are obviously some signs you are demonstrating that you’re not aware that you are displaying. And, trust me, people can pick it them up. Also, many men, and women, are not comfortable enough to identify with their sexual desires and interests. And, that’s okay. There are many men who fight, and deny their sexual urges and identity. They don’t, and can’t understand why they have the feelings they have for the same sex. It is peculiar for them. It is difficult and a long process to accepting yourself for who you are, as well as the many challenges and obstacles gay men and women experience with their family, friends, and co-workers.

But, Ms. Honey, your ex had sex with a Transsexual. WOW! That is some serious –ish. And, after the experience he determined that he was straight. Hmmmm. I’m not buying it. Especially the fact that he enjoys watching porn featuring Transsexuals.

There are many men who are fascinated with men who are extremely effeminate, and identify with being women, and that is a turn-on for them. Many men who don’t identify as gay will prefer a Transsexual person because in their minds they are having sex with a woman. They may have the appearance of a woman because they dress up and act very much like a woman, and for the man it provides enough of the fantasy for them to be with a woman, yet they have the equipment of a man. In their heads they are having sex with women, not men.

I do commend him for being honest and telling you about it upfront. He let you know what he was dealing with, how he felt, and that he had sex with a Transsexual person. Now, clearly, I feel he was reaching out and he desperately needed someone to talk to about it. Trust me, he is still struggling with himself. He is trying to make sense of it all. Do I think he will experiment again? Of course I do. Will he ever admit to himself his true desires and identity? It will take some time. He needs to be comfortable with himself. Or, he may never accept it and creep and do it.

So, Ms. My Ex-Man Was Into Transsexuals, my answer is YES! If a man has had sex with a Transsexual person it is a red flag. Just because he didn’t like that experience doesn’t mean he won’t do it again. Maybe Transsexuals are not his thing, but a man who will go out intentionally and buy porn featuring Transsexuals, uhm, boo boo, your man is telling you something. You better pay attention to the red blaring signs blinking in front you. – Straight From Your Gay Best Friend