My best friend is struggling with his crossdressing...and I just want to be with him

[twostraightlines]

Okay, for those of you who have a minute...
I've been friends with Gabe since we were in elementary school, and we're both 22 now. I met him in first grade and we were instantly the best of friends. I was always more of a tom-boy as a kid, and he was more sensitive and let me boss him around. I'm not sure if that contributed to his crossdressing. Apparently it's something he's been doing for a long time, but I never knew about it as a kid.

He moved around a lot as a kid, changing towns and schools and eventually states, but we always tried to keep in touch and hang out when he was in my neck of the woods.

Just recently we started hanging out again since he just temporarily moved back to our hometown. He's been having a terrible time with depression, addiction, etc...he's in a bad spot and needs help. When he's with me, though, he starts to act like his old self, and seems to slowly be healing. It just feels like a relief to be together again- he laughs freely and easily, and smiles more. His mother was the one who told me this- that when she saw him and me together, that was the first time she'd really seen her son in a long time.

I've had feelings for him since I was old enough to start noticing boys, but I never told him about it. He was always big on me being "like his little sister" and all that, so I assumed he didn't feel that way about me at all and just learned to ignore it over the years.

One night, though, we ended up hooking up. We were just watching a movie, and he puts his arm around me, and then he's kissing me, and well, you know where this goes. He initiated it, but I didn't stop him. I did stop him, though, when he said something along the lines of, "Oh, this is great. We can just do this until I move to New York in a month."

I felt my heart drop...I've been in fwb deals before and they destroyed my self esteem. I knew I couldn't do that again. I told him that, along with the fact that I had feelings for him, and that in all honesty, I'd love to be with him like that, just not casually.

We did a lot of talking about what would be best moving forward, and decided we just needed to stay friends for the moment. This was heartbreaking for me but I understand he's going through a tough time, and I want what's best for him.

A couple days after that, I was helping him pack to move to NY (painful for me, but he needed the help) and he came out to me about his crossdressing. He had never mentioned this before. I think he felt I needed to know, since we've been getting closer again...or maybe he wanted to warn me to see if I'd run...or maybe he just wanted to tell someone. He's pushed a lot of his other friends and family away (maybe because of the crossdressing, but more than likely because of all of his issues that he's going through). The only other person he ever told was his ex girlfriend, who was bi and who was really into his crossdressing. The relationship ended badly but he misses the sex very much.

He told me the fact that he has to hide his crossdressing takes a huge toll on him. It's a part of himself that he has to keep under wraps. As I am an artist, I asked him if it would be similar to me having to keep my drawing a secret, as drawing is a huge part of who I am. He said that's exactly how it feels. He's so ashamed and embarrassed that he wants to do it, but at the same time depressed because he can't do it...

I know he's not in any condition to be entering a relationship right now...but part of me wants to wait for him to work it out so we can be together...

*But* I'm not in any way aroused by the thought of him in woman's clothes. We had such great chemistry the time we hooked up. It was literally perfect, I was so into it. What if he puts on an outfit that makes him feel sexy and confident, and I don't like it? I've never been attracted to women, so I have no idea how I'll react to it. I'm afraid throwing this into the mix will...I don't know...kill my attraction for him...

When I get right down to it though, it breaks my heart that he's so ashamed of something that makes him happy. It doesn't seem like a big deal to me in theory- if a different outfit makes him feel like a million bucks, I don't care if he wants to dress like a dinosaur. I want to see him happy and confident, end of story, right? But could this be a sign of other, more serious gender/identity issues? He assured me that he's 110% straight, but I don't know if it's wise to believe him...

Thoughts? Advice? Similar stories? Help? Literally, anything? I have no idea what to do here...

[Nadine Spirit]

twostraightlines-

Hi. Welcome to the forum. Now, as for your story, wow - lots going on there!

I certainly cannot address everything, but some thoughts I have-
1 - You sound like a great person, very open minded and concerned about your friend
2 - I have no idea if he does or does not actually like you, I know for me, I was super insecure at that age, and too dumb to realize that some of my childhood friends actually liked me more than a friend. They would have needed to hit me over the head with a frying pan for me to understand they really liked me.
3 - It is fine to wait for someone, but when it goes on too long, it can be pointless and hurtful for you
4 - So what to do about possibly not finding him attractive while dressed? Lots of folks here support their SOs cross dressing and never include any sort of sexual activity into it; it is perfectly fine to do that. Some partners though can figure out a way to have sex and enjoy it. You say that you are not into women, well realize that just because he may dress as a woman that does not make him a woman. Underneath the outfit is the same person.
5 - When pondering if he has "more serious gender/identity issues?" It is a bit vague. What is serious to one person may not be to another. So to read a little into what you may mean by that statement, many SOs are worried about the CD beginning the process of transition. At this point there really is no way to predict if that will happen. You can ask him, but he may not know.
6 - Oh and yes cross dressing does not predict sexual orientation, some CDs are gay, some are bi, and some are straight.

Good luck!

[Nikki A.]

Just because he dresses most likely does not make him gay or looking to transition. What is more bothersome to me is what is the root of his depression & addiction. These usually manifest as an escape from the stresses of life (as sometimes dressing is to a CD).
Be a friend, listen to what he says , don't be afraid to ask questions. Use your instincts to figure out if there is a romantic spark, if not just be a friend. It sounds like he could use a friend like you.

[tammie]

HILuvs: Twostraightlines, you mention an addiction issue , if its meth move on alone and maybe say goodbye to your friend one last time and remember to smile. Its that bad and there is about a 90% recidivism rate with meth even with sincere attempts to

stay clean. 420 use is less destructive but still is breaking the law in many jurisdictions and legal problems are costly in both $ and relationships , alcohol has a gamut of problems and many different levels of participationbut is legal again in most places .

So don't just gloss over that word of addiction assuming it will go away, please protect yourself .

Good Luck to you, and to Nadine Spirit , what a wonderful thoughtful answer you posted , Good on you dear for taking the time .

[Lorileah]

I was always more of a tom-boy as a kid, and he was more sensitive and let me boss him around. I'm not sure if that contributed to his crossdressing.

NO it didn't. but you make a point a lot of people don't get. It isn't something someone else did or didn't do. Also don't confuse being submissive or shy with crossdressing

I felt my heart drop...I've been in fwb deals before and they destroyed my self esteem. I knew I couldn't do that again. I told him that, along with the fact that I had feelings for him, and that in all honesty, I'd love to be with him like that, just not casually.

then don't. You must do what you feel is the right thing, not what you think you should do. If it makes you happy, do it. If it makes you feel degraded...don't

*But* I'm not in any way aroused by the thought of him in woman's clothes. We had such great chemistry the time we hooked up. It was literally perfect, I was so into it. What if he puts on an outfit that makes him feel sexy and confident, and I don't like it? I've never been attracted to women, so I have no idea how I'll react to it. I'm afraid throwing this into the mix will...I don't know...kill my attraction for him...

and the major gist of this. You can love him and not like crossdressing. Ideally you would accept this part of him unconditionally. Love make exceptions for what we really feel *but* if you read a lot of the posts here you will see that many women are not in any way attracted to any form of dressing. It is the "norm" and not the exception. So you have to make lines in the sand if you pursue this. You both have to agree where and when and how much AND how you will or will not participate

When I get right down to it though, it breaks my heart that he's so ashamed of something that makes him happy.

and THAT is a sign of a true friend

But could this be a sign of other, more serious gender/identity issues? He assured me that he's 110% straight, but I don't know if it's wise to believe him...

Yes it absolutely could be a sign of deeper issues. Or it may be just what he does. Or... There is only one person who can answer that...him. YOU on the other hand have to decide just how far you can trust him. People lie for a lot of reasons...not the least is sex (can we back up to the "bi" part? Was his GF the ONLY one who was "Bi"?

I have no idea what to do here...

Join the heart over mind club. If this was easy everyone would do it, there would be no divorce and we would all have castles. Trust me. I can easily tell you what I 'would" do but I don't follow my own rules many times. You have to decide. Can you live with the crossdressing,;maybe even learn to grow to like it (My GF was on board form the start and we had a great time together). Can you live with any other speed bump that may occur? I know you don't know right now because you wouldn't be posting here. But you have to please yourself right now. You are not invested in him, yet. You let it grow and decide later that it wasn't right...you will hurt a lot more than you do now

[Katey888]

tsl - welcome first of all

Good advice and points from Nadine already... All I can add is to emphasise what you've already said yourself - you imply that this used to be an integral part of sex for him (that might be an incorrect interpretation) and if it was, that might be a dead end for you.. That's a big question for you to answer, because if you can't see your way to accommodating that, then I can't see a way to a deeper relationship. If it's not that, then perhaps it is a different story...

His CDing may not be any indicator of a deeper gender issue... or it may be. You'll have to talk about this and he may need some professional counselling. He clearly has some other issues to deal with as well - that can't be helping any of this either. Having a gender 'issue' does not predetermine sexual orientation - but the extent and nature of the issue may obscure this aspect of an individual. It needs a lot of talking, probably a lot of help, time and patience...

You're a diamond girl to get this far with your thoughts, but I'd suggest you must explore some of these potentially serious issues with him before committing yourself in any way. Does he feel the same way about you? Seems he was happy to depart back to NY without you...? I think I'd want to be sure about that aspect too...

Good luck, young lady - look after yourself...

Katey x

[CONSUELO]

As some have already mentioned you should be wary of the addiction and depression issues. I think that would be the first item to tackle and resolve before moving on to what to do about his cross dressing. Take a look at the many related topics on this site and you will find a wealth of experience and insight that will be helpful to you.

Best wishes and I hope something good comes of this for you. Sounds like you really deserve it.

[kimdl93]

Well, there are so many complexities to this situation. I am glad you were honest with him and find it encouraging that he could express himself about his CDing. If all the other issues can be resolved, maybe there a way forward. Addiction is the first hurdle, but probably intertwined with depression. And of course his repression of the desire to dress may contribute to both of the former. I don't see that it's within your power to heal him, but you can aim him towards resources that can.

As for sex...remember that ultimately, you're not making love to the clothes...even if he is dressed as a male, his mind and his intimacy ultimately may be female oriented...even if he hasn't thought much about it. And sex, ultimately isn't about gender so much as the exchange of the most intimate desires and feelings between two people. But before you have to face any such moments, he needs to get clean, sober and emotionally healthy.

[mykell]

two straight lines welcome to our world, you deserve a group for your understanding and compassion, oh and its definitely not your fault.
so many thoughtful and encouraging posts already, not much more to say,
my best advise is to follow your heart and if its in the cards the two straight lines will become intertwined into a well co-ordinated bow....
the depression and addiction may be a problem from him accepting who he is, many here struggle with this, maybe with christmas coming up a girly gift for your friend, a trinket of acceptance, even if you dont hook-up....but stayed a friend....
i wish you the best and hope that you can get anchored up where its convenient for you both if its in the cards....hope we helped you....

[docrobbysherry]

I think Lorileah posted most of what I was going say. Only better and with more authority, Two.

However, I CAN add 2 points from my experience.

1. U and he r both very young. Neither one of u is sure who or what u will be yet. But, I bet u will look back at yourself in 10 years and laff about these times. I don't mean to make lite of how u feel now because I know it must hurt unbearably sometimes!

2. U shouldn't worry about the, "what if's". What will happen, will happen. No one knows their exact future, so don't guess. If u want to tell him how u feel? Do it! Call him, text him, whatever. If he gets tired of hearing from u, he'll let u know. Your feelings r never wrong, even when u look back and u think they were.

It sounds like u may need him as much or more than he needs u. But, only time will tell. And, even tho it may not feel like it? Take it from this 70 y/o, you've got all the time in the world, Two!

[Gardener]

My immediate thought is to say that as people at different times we fulfil many different roles in life. Whatever he might think he wants from you, he needs you as a friend, who knows and who won't judge. The only complication is that a door opened into a different way of relating and it is not always easy to go back into the other room. For him and for you it might be well worth trying to maintain the historic relationship albeit enhanced by your deeper knowledge of him. Good luck

[twostraightlines]

Thank you all for the advice and kind words...

For now, I guess there's not much for me to do other than be the best friend I can be and to make him feel accepted.

I got him some DVD's for Christmas in the hopes to cheer him up- Eddie Izzard's "Dress to Kill" DVD (he's a famous comedian who crossdresses when he does his sets) and the movie Kinky Boots, which just sounded fun. It will hopefully be relevant to him because he's an actor and wants to work in movies. I hope he doesn't think I'm making assumptions about how he views himself or how he wants to be, I just want him to see that people can both express themselves, and be successful and loved...

I'm anxiously awaiting the opportunity to talk to him more about this, and to continue learning about my best friend.