How can I approach my boyfriend about his cross dressing?

**Cicatrixx** · 08-05-2010 07:03 PM

Okay, this is going to be a little long but I would really, really appreciate some help! I haven't had any one I could talk to about this because they all know my boyfriend but it's something that's come up and I could really use some advice...

So my boyfriend and I have been dating for just over two years now. I'm almost 19 and he's turning 22 this month. After I graduated high school, we had dated for 11 months but we were both going to go to school in the same city so we decided to move in together. Now we've lived together for just over a year and we've had lots of fighting and stuff, but that's not really the point.

Anyway, a couple months ago, I was cleaning and trying to unpack some more of our boxes and I found this red bag in one of his boxes and I pulled it out, not really thinking anything of it and when I opened it I found a some lingerie, a little dress, underwear and some bras... but I also found a pink wig, fake breast forms, sunglasses and a dildo. I was really confused at this point... I didn’t really want to think to myself that he was wearing it so I just left it alone, because our anniversary was in a month or so at the time.
In July I visited some family and when I came back my boyfriend told me that he thought we should live in separate places because both of us have a lot of stress and family problems we have to deal with, and it will be better for our relationship. I agreed with him eventually because our fighting has been getting ridiculous. But during that time when we were emotional and crying I told him that I found his red bag and kinda briefly said that I hoped it wasn’t meant for someone else and all he said was “you weren’t supposed to see that..” and I left it at that.
When our anniversary came up and he never said anything about it, I brought the red bag up again the next day and he got really defensive and said he didn’t want to talk about it. But that just made me angry because I felt like he was lying to me about something because I never really put it together so we had a big fight. I got really upset and went into the bedroom. I started to pack up the rest of my stuff because we already moved most of it. He still wouldn’t really talk to me about it but then he said something like he’s had to accept certain things about my sexuality without question (because I’m bisexual... this caused fights too) but we’ve talked about it openly a lot in the past and he wouldn’t talk to me at all. He also said that he’s had to deal with this longer than he’s known me and that he could never ever ever admit to anything like that because of the friends he has and stuff. But after the fight we just tried to let it go and not talk about it. I was still confused at first, but eventually all the pieces started to fall into place and at first it made me feel really confused about the way I felt about him and myself.
But now, I’ve thought about it a lot and done some research about cross dressing and I feel that I can understand a little more. I know he may not necessarily be gay although I’m beginning to question if he might have some attraction to men because of the dildo I found. I want to be able to talk to him about it more but he’s a very private person. I think it could be something we work on together because I know how hard it is to struggle with your sexual identity and the more I think about it, the more fun I think it could be, but sometimes the thought can still make me feel a little uncomfortable, mostly because it’s still fresh and he hasn’t told me anything. But I my question is how can I bring this up again without making him feel insecure or completely shut down. I know it’ll take time but I want him to know that I’m there for him no matter what and that I want him to feel safe talking to me about it. And if he isn’t able to talk to me about this at all, ever – I don’t think I can go on forever with this relationship because I can’t just have that hidden from me and never talked about, it will always be on my mind. I’m sorry this is so long, but I really appreciate anyone who answers!

**Beautiful Disaster** · 08-06-2010 06:47 AM

Sounds like it's the secrecy that's bothering you, and I can't say I blame you. Trust is huge. You were honest with him about your sexuality, it caused problems, he gave you a hard time about it. Now he's not quite being honest about his own. Not really fair.

I'd guess his desire to not live with you, was so he could be "himself", dress in his girl clothes when he wanted, express himself in that way without having to explain it to you. He's not comfortable with it. He's not comfortable with himself....therefore he can't even begin to be comfortable with being open about it.

He's a lucky guy that he has someone who would even be willing to consider this type of lifestyle. But you can't make him be open and honest about it. The more he hides, the more doubt you will have about "who is this guy really?". And if he's so ashamed of this cross dressing stuff....then maybe there is more....maybe he does like guys too?

If it were me, I'd sit him down and have a talk. Reassure him how much you love him and that his preferences won't make you stop loving him, but that it's not fair to offer you anything less than honesty. You deserve to know who you're with, what you've "signed up for". You deserve that. And if he refuses to be honest about this.......then I'd walk and give him a chance to figure himself out without me.

**Olympia** · 08-06-2010 09:14 AM

IMO, it seems that you have been 'open', honest about your sexual preferences, and he is not.. you state...

(because I’m bisexual... this caused fights too) but we’ve talked about it openly a lot in the past and he wouldn’t talk to me at all. He also said that he’s had to deal with this longer than he’s known me and that he could never ever ever admit to anything like that because of the friends he has and stuff.

From what i read, he seems to deny this of himself. He may find you a threat, due to your comfort level of honesty. (admittedly bi.)
I agree with BD, in a relationship there must be trust and honesty.
But there should also be mutual respect !

**Beautiful Disaster** · 08-06-2010 09:33 AM

But there should also be mutual respect !

Exactly!! You're not asking him to be someone he's not, you're not asking him to live a lie...you're just asking him for the truth so that you know what you're dealing with. He needs to understand that if he chooses to hide his true self from his friends and the world around him, then that's his choice......but that it's not okay to hide who he is from you. That's just asking you be in an insecure untrusting relationship with someone you don't truly know. Definitely not fair to expect that of you.

**AnGelWitHHornz** · 12-18-2010 05:56 PM

I feel for ya, My boyfriend is a cross dresser and it really bothers me. He says that He does not desire to be with a man, but it just makes no sense why He would enjoy being dressed as a female. Not to mention that He has had homosexual relationships in the past. I am not sure what to do about this.. we fight everytime the subject comes up because it really makes me feel like i am not good enough for him.

**WildChild** · 12-18-2010 06:13 PM

Not sure what to suggest on this. You are dealing with young men who still aren't comfortable with themselves or their sexuality. I was in a discussion group recently that included an cross gender person, they shared having spent the past several years living and dressing as a woman and are now spending time exploring living as a male. Some people can deal with this and make a relationship that works. They need to be clear and comfortable with who and where they are with this. If you want to have a ltr and possibly have a family, you need to know exactly where you both are in terms of sex and identity.

Certainly a man can be a good and positive parent and partner regardless of his preference in attire. The real issue is what his sexual preferences are and what you can live with.