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How do I tell my girlfriend, "sorry, my life has been a lie, I'm gay and a cross dresser"?

Tagged as: Big Questions, Dating, Gay relationships<< Previous question   Next question >>
Question - (29 September 2019) 7 Answers - (Newest, 2 October 2019)
A male United Kingdom age 41-50, anonymous writes:

I'm gay and I don't know how to tell my partner or even how to live as a gay man.

I've been attracted to other men for as long as I can remember, but I've only dated women, or had relationships with women. At first I told myself I must be bisexual because I was still able to get physically aroused enough to have sex with women. I don't enjoy it particularly, beyond the pleasure it gives the woman, but I can do it.

I've been in denial or at least repressing my sexuality and as time has gone on, I've realised that there's a huge hole in my life and the only thing that can fill it is a man. However, I don't even know where to begin.

I was in a long-term relationship that ended - ostensibly because we wanted different things in life. However, we'd basically become friends, with nothing physical taking place (by this stage, I had started sleeping with men (always with protection), I met on dating apps). We went our separate ways. I stayed single for a while, but then began having casual sex with men. When I'm with a guy I fancy, I feel alive and free. I just feel like me. But I also feel ashamed. I'm what you might call a lads-lad, I lift weights everyday, I drink beers with the boys. Women have always wanted me. Everybody thinks I'm straighter than straight. I'm not. I'm a total submissive 'bottom', I love to wear women's clothes, I love to give oral, to be spanked and penetrated. If I let myself be me, I'd be much more feminine and cross dress. But I can't. I just can't.

Now I'm in a relationship with another women. We've been together for the best part of 3 years. At first it was OK, we get on great and the newness seemed exciting. I thought, I was 'cured' (I know how silly that sounds). However, the same thing has happened again. I can have sex with her, but I don't really enjoy it, I'm on gay apps, although I haven't cheated on her. I'm desperate for gay male company, to have sex with men, to have a relationship with a man, to properly explore my feminine side. To be free. But I can't. I just can't do it. I'm 40, I can't turn around to everybody I know and love and say: sorry, my life has been a lie, I'm gay and a cross dresser.

Anyway, my partner has gone away for the weekend and I've spent the whole weekend dressed as a woman, fantasizing about sex with men. I even met up with a trans women. We dressed each other and put make up on. I felt amazing and sexy, but also ashamed. Now my partner is coming back tomorrow and I've realised I can't live like this for much longer. It's extremely selfish and unfair on her. I need to let her go, but how can I tell her I'm gay?

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A male reader, Billy Bathgate United States +, writes (2 October 2019):

End the relationship as gently as you can this poor woman deserves better than to have you waste anymore of her time. Then get yourself to a therapist one who can help you come to grips with who you are. Then maybe you’ll stop messing with Women’s lives because you’re to big a coward to be yourself.

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A male reader, anonymous, writes (30 September 2019):

Why are you in a relationship with a woman if you want to be with a man? It's incredibly selfish if you to lead your girlfriend on. End things with her so you can both be happy.

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A reader, anonymous, writes (30 September 2019):

She deserves to be told, and you should allow her to find the type of man she thinks she has. It's counterfeit, and selfish to know you're not really into women; and allow someone to invest their feelings, emotions, and time on you. All the while, knowing you're only pretending. Meanwhile, she's thinking she's in a real committed-relationship; you're thinking of men, and dressing-up in makeup and pretty clothes.

You can only imagine the emotional devastation she will experience to know it isn't real. She needs time to digest and recover from the truth. She may even have some suspicions. You can't fool everyone! The truth must be told sooner rather than later. Time is the enemy! Chances are, she has already been through your devices.

I'm not going to get into your lifestyle. Just the matter regarding honesty and exploiting another person's feelings; basically to use her as a beard and cover.

It is likely she is expecting your commitment to evolve on different levels, possibly leading to marriage. Even if that isn't the case, she thinks she's in a heterosexual-relationship. She isn't.

Tell her! The deception and this facade is totally unfair.

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A female reader, chigirl Norway +, writes (30 September 2019):

chigirl agony auntYou say that you cant live openly as gay, because that would mean saying your life is a lie. You say it is unfair to your girlfriend to live a lie with her. What strikes me is: this is your life. Its not about these other people or what they might think of you. Living a lie is not fair to YOU. No one else gets hurt more by this than you. And no one else but you, have the right to say how you should live your life. You do not owe it to anyone to be straight. This is your life, your sexuality. And you owe it to yourself to be who you are. You deserve to live a life free of lies. You. You are the important person here. Be mindful of yourself now, rather than everyone else.

You can just tell your girlfriend the truth, or you can end the relationship and not tell her anything. Its completely up to you. You decide what is best, but do yourself the favour of doing what is right for YOU, for the first time.

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A female reader, Youcannotbeserious United Kingdom +, writes (29 September 2019):

Youcannotbeserious agony auntHaving been at the receiving end of what you are doing, it infuriates me that men think this is ok. Although we are talking about nearly 40 years ago, I still remember how dirty and used I felt when I found out the guy I had been dating was actually dropping me off at home then heading into town to pick up rent boys. What you are doing is not only harming you but also your poor girlfriend, who has no idea what is going on. You have no right to do this. Don't play the victim when you are doing this to someone.

If you feel anything for her at all, you need to stop this relationship NOW. I would advise not actually telling her the real reason but just giving her some other excuse. Then, and only then, you can explore your real sexuality.

What is more important to you: finding out who you truly are and being happy, or your image and what (some) people will think of you? Your real friends will remain your friends; the others don't really matter.

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A female reader, Honeypie United States +, writes (29 September 2019):

Honeypie agony auntI'd end it. And I'd tell her that you have come to the realization that you need to be true to yourself and that is being a gay man.

It's UNFAIR to use her as your "nice straight-man facade". She doesn't deserve that. You know this.

While I get you think you SHOULD be straight and have a "normal" life with a gf/wife and the whole she-bang, that JUST isn't YOU, not your genuine you.

The fact that you are ON gay apps means you are already detaching yourself from her. Meeting up with a stranger to (pardon the expression) play dress-up means you aren't REALLY sorry about potentially cheating or hurting your partner. My guess is she will be WAY more hurt when you tell her it's over because you are gay. I do think you should tell her. Not sure about the X-dressing, but I think the gay part. I think SHE deserves the truth.

Whether you can be out and LIVE as a gay man is another issue, something only YOU can figure out, DON'T use another woman as your "shield" from reality.

Maybe there are some counseling or a forum for gay men who have been in denial, or aren't out, etc. It might be good for you to talk to other men who have been in your shoes.

Time to do right by her. And... by yourself.

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A female reader, anonymous, writes (29 September 2019):

You know you're gay so it was extremely crappy of you to get involved with a woman and stay with her for three years pretending to love her. It's not like you *just* figured it out. You knew from your last break up.

You know you're being selfish so you know you need to end it. I assume you care about this woman a certain amount, so let that make you do the right thing. You're holding her life back. You're holding her back from finding someone she really loves.

I might sound harsh but if it helps, I am a lesbian who was in a relationship with a man for a long time so I say it as tough love.

You don't *have* to tell your girlfriend you're gay. You just have to tell her you want to end the relationship.

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