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Dear Gay Best Friend,

Let me start this off by saying I found your column very helpful. You have straight forward advice no holding back and that is what I need right now.

Okay, here is my story. About 2weeks ago I borrowed my boyfriend’s iPad. When I turned it on there was a She-Male sex site! Let’s just say I snapped when I first saw it. So, I started doing some investigations of my own. I found that all these sites were from 2003/2004. (Oh yeah, there were more than one) So, I confronted him about them. He admitted to me that years ago he was with a Transgender woman and that he slept with her. He said at first when he brought her home he thought she was a woman, but when they got in the bedroom he found out different but still did it anyway! He told me after that he started questioning himself and what attracted him to her even after finding out she was a man. So, he started to explore the Internet and wanted to know more about She-Males. He said he tried it one more time after that with a Transgender woman, but didn’t enjoy the experience so he never did it again.

He was trying to erase this site when I stumbled across it. I did see that there was no activity on these sites for years and that he just never deleted them. Now, this man is my best friend we have been together for almost 3 years. He is very good to me. I work 3rd shift at a gas station 3 days a week and he sits in the parking lot the whole night to make sure I’m safe, and then goes to his own job in the morning. He has always been there for me no matter what. I’m trying to be understanding to the situation everyone has a past. I’m not questioning his love for me because I know he does. But, what I am questioning is can someone engage in homosexual sex and then be done? Could it have been he was just experimenting with his sexuality? I know around that time he went through a nasty divorce with his ex-wife whom was cheating on him.

Whenever I have a question he answers it for me. He says I am what he wants and wants to marry me. I love this man and want the best for him I would stand by him no matter what as he did for me. I told him if he is still struggling with his sexuality I will always be his best friend if he has a desire for these Transgender women, and I would understand and wouldn’t judge him. But he reassures me I’m what he wants. Hell, I even offered to bring one in the bedroom with us but he said no! That he was not into that and it was that one Transgender woman he was attracted to and that’s it. I know when I was younger I experimented with a woman and I have no desire to be with a woman again. Could the same thing go for him? Sorry if I dragged this on. I just have a million questions going through my mind. – Trying To Understand

“I Can’t Stand My Husband And I Cringe At The Thought Of Him”

Dear Ms. Trying To Understand,

I agree, that yes, we all have a past. And, many of us have done some things and have done some experimenting including having same sex relations. But, experimenting with a She-Male is a whole other thing. Your man brought a Transgender person home under the guise that he thought he/she was really a woman. Once they got into the bedroom he discovers he/she is not a woman, and yet he still goes through with the sexual act. WOW! Okay. And, he just didn’t do it once, but he tried it a second time with another Transgendered person. And, after the second experience he determined it was not for him.

Okay, I don’t want to put any doubt in your mind, but your man actively sought out a Transgendered woman and went back a second time. It wasn’t by happenstance or coincidence like his first “alleged” time with a Transgendered woman. But, the second time was purely intentional. It was premeditated and planned out. You see, I’m on the fence with this because you say that he said the second experience wasn’t satisfying or gratifying. And, afterwards he concluded that because he didn’t enjoy it, then he didn’t try it again. So, does this mean he won’t ever try it again?  Remember, he did admit that he was attracted to the Transgendered woman. And, I’m not so sure if any heterosexual man would have said, “Well, since you’re here we may as well have sex.”

Here are my questions: Why did he go back a second time? What did he like about the first experience and what exactly did they do? What type of sexual act was involved, such as penetration from both parties? It’s obvious he enjoyed and got some pleasure from the experience because he went out to do it a second time. But, what about the second experience he didn’t like? Was it because he wasn’t necessarily attracted to her? What was he hoping they would do? There are lots of questions, and he has all the answers. I strongly suggest you sit down with him and be prepared to have all your questions answered, and be open to what he has to say. You may not like what he has to say, and it may be uncomfortable to hear the truth, but instead of wondering if he has an attraction for Transgendered women, and if he may be homosexual, you need to talk with him and get all the answers you need.

And, I do believe that a man or woman can have an experience, and may never do it again. I do believe that one experience does not make you homosexual. But, several experiences, and you questioning your sexuality, and you don’t tell your current partner about your past, then you’re hiding something. (Leans in and whispers: What is your man hiding?)

I don’t understand you women who won’t communicate, or ask questions of your men once you find out that they have, or had, or engaged in a sexual act with a man. You don’t ask questions to get the answers you need, so you start assuming, guessing, and making excuses for them. STOP THAT MF’ing –ISH RIGHT NOW! Stop dancing around the situation and walking on egg shells. Get to the bottom of it, and find out where his desire and attraction stems from. Does he like the fantasy of getting both male and female genitalia? Does he like having his ass played with, and the idea of a woman pounding him? Is he into sucking d**k and breasts at the same time? Girl, you better ask these questions. Something is turning him on, and you better find out. You need to understand his sexual fantasies and desires.

But, I do want to give your man some credit because he researched and scoured the internet trying to understand his fascination and attraction for Transgender women. Now, here’s where I’m stumped. You said he questioned himself after that experience. Ms. Thang, did he ever find out his fascination and attraction? You didn’t say that in your letter, and I’m assuming he didn’t because you drew your own conclusions by saying he was going through a divorce so perhaps that made him do it. Uhm, really sweetie? A divorce can drive you to have same sex relations, even to the point of a Transgender woman?  Your man said he was attracted to her. HELLO! I really think there is something else driving the attraction, and it wasn’t the divorce. By the way, he says it was only that one time, but it wasn’t one time, it was two times.

Sure, your man may have only done it twice. He may have even searched the internet seeking out Transgenders and his fascination and attraction for them. But, the fact remains that they were on his computer. He didn’t delete them, and although there has been no activity on the sites for years, they are still on his computer. And, how did you stumble across them? If you were able to access them that easily then it’s obvious that they are sitting right there in plain sight, or in his cookies web history. So, then how come in all these years he still hasn’t deleted the sites? I’ll wait for an answer.

Here’s the thing. Having those sites lingering on his computer is like having an ex lingering in your life. Although you’re not communicating with them, you still haven’t quite gotten rid of them, and they are hanging in the balance. And, if the right moment and right opportunity presented itself you will find yourself revisiting your past. So, if he’s really over the experience, and Transgendered women are not his thing, then the two of you should sit at his computer and delete all the sites. Really make it history and a part of his past. DELETE THE –ISH!

You sound like you have a good man, and that he really loves you. I don’t doubt it, nor do I doubt that he really wants to make a life with you. But, ask yourself this question – If you’ve been with him for nearly 3 years, and he’s never told you about his experience with a Transgendered woman, and the only reason he confessed is because you stumbled upon the websites on his computer, then do you think he would have ever told you? I just want to say this, your man has some secrets, and you don’t know him as well as you think you do. It’s time you two sit down and be really honest and open with one another. There are some skeletons hidden, and your man has a closet full of them.

Finally, Ms. Girl, I do applaud you for being open enough to support your man, and be there for him. Even to the point of being his best friend if he is struggling with his sexuality. You truly are understanding and amazing. There are not many women like you. However, I don’t think you should have, or even think about exploring bringing a Transgendered woman into your bedroom. Honey, trust me, you will be the odd ball (no pun intended) left out! – Straight From Your Gay Best Friend

Make sure to get your copy of my new book,  Mogul: A Novel (Atria Books – June 2011; $15). It is available in bookstores everywhere, and on Amazon, click  HERE!

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