Cross-dressing boyfriend- need advice?

Question

My boyfriend, who I love and with whom I would like to have a long and happy relationship, is a cross-dresser. He told me a few months ago, and I was surprised and (to be honest) not exactly thrilled, but I figured it doesn't hurt anyone and there's no reason why it should bother me, so I decided to just be glad he trusts me enough to share this about himself. He is not a virgin, but he is inexperienced for his age and our culture, and he's self conscious about that and wants to take things slow. Again, fine. He's an incredible person and I can wait for him to be ready, except... he is ready I think, but not ABLE. He gets an erection when we are fooling around, and I have brought him successfully to orgasm before, so maybe it's just nerves, but the other night we were about to, uh, copulate, and he just... went soft. He says it has been a problem in past relationships and is not me. I want to believe that, but if it isn't me, what is it? If it's been a problem before, it isn't

a one time thing, which means it's a real problem. Do you think if I offered to let him dress up in bed, that would fix things? I know cross-dressing doesn't make you gay, and he says that he is straight and finds me attractive, but he could just be repressing his own sexuality because he isn't comfortable with it, couldn't he? On the other hand, I can't be asking him if he's gay all the time, it would be annoying and also disrepectful, since I firmly believe that everyone has the right to define their own sexual identity without being questioned about it. Is he sick or depressed? What is going on here, and how can I fix it? I am not in this relationship for the sex, but that doesn't mean I never want to have any!

I am not out of patience or anything, I am just not sure what, if anything, to do. Do I talk to him and risk making him feel worse? Do I ignore it and never get what I want? As I said, sex is not the most important thing. I wouldn't break up with him over this, but I can't see myself marrying someone who can't satisfy me physically either, and while I feel guilty and selfish for saying so, it's just the way it is. Sex is important in romantic relationships. Also, what if I wind up marrying him and then ten years down the line he realizes he's gay? He wouldn't intentionally deceive me on that front, but he might not know himself.

Answer 1

I guess the question you need to ask is whether this is related to his cross-dressing. Erectile disfunction happens for a HUGE variety of reasons, which can be physical, emotional, psychological, or just 'one of those things' that happens sometimes.

You sound like you believe that it has to do with the cross-dressing, which may be very true (it may also not necessarily be). In that case, it might be that he is worried after divulging this secret to you, concerned about what you might be thinking, although it sounds to me like you are very comfortable with the idea and understanding. Still, he could be on edge, thinking you think him weird and want to leave him- and that can psychologically keep him from getting an erection.

I know someone mentioned he being gay, which, I assure you, is not the case. I mean, it could be, but just because he is a cross-dresser does not mean he harbors homosexual feelings. There are many straight cross-dressers and there are lesbian male-to-female transsexuals. And because he is still with you, has had other girlfriends, etc., I don't think he's gay. He might, however, have some wonderings about transsexuality. When one crossdresses and finds pleasure in it, the topic of transsexuality always comes up, even if the ultimate decision is that no, I don't want to change my sex. He might be grappling, trying to decide if he really wants that penis that he tucks away while cross-dressing, and this may be a source of the erectile disfunction.

My answer is always the same. Talk. Communicate. Don't be accusatory (I doubt you would be), just ask if there's anything more he wants to talk about with the cross-dressing thing, or just life in general. It's not you, it's something going on with him, and discussing it in a calm, open, understanding way is the best.

Here's to hoping things will, um, shape up!

Answer 2

Pretty much all the corners have been covered,, but I would also say this,, in your search browser type this in " Do you know a Crossdresser " and then do yourself a favor and read it,, it may help you to understand a bit more, and this is when every little bit helps, and if this help, I am 46 been a CD since 14,, Many many times I felt like I didnt belong and like I knew I couldnt talk to anyone for fear of rejection and other things,, If you let him know that he can talk to you anytime he feels the need that would be such a BIG relief for him I am sure, I WISH I would have had someone I could have talked to, as much as you are dealing with acceptance of the situation, I would bet he is still dealing with it too, It took me many years to feel at ease with myself, and I have been there as well,, sometimes just get in a mood where things dont work right unless we are wearing something that feels right

Answer 3

Hi, I'm a gay transvestite but trust me I'm in the minority by far. There are some tranny sites where you may be able to talk to partners of tv's like www.tvchix.com or you can get info from www.beaumontsociety.org.uk. You can search for female admirers at tv chix and maybe get some support that way. You should find that the community is very supportive and you are far from alone. You come across as a fantastic woman so he's very lucky indeed. Feel free to message me, hope it all works out for you xx

Answer 4

I think you're right to think it would help if you inticed him to do it, tell him it really turns you on to see him like that and you can even make it a couple's activity to dress him up in different outfits (I know you had barbie dolls too). I do it with my bf on occasion and we started out the EXACT SAME WAY. He was nervious and I was a bit too but both of us thought it was acceptable and knew we were just being silly by being scared.

I would drop hints throughout the day here and there and then try to get him to do it at night. It wasn't really my thing at first but I knew he wanted it and I was trying to make it easy on him.

After a while though it REALLY made a difference in our sex life, we're both really creative people and he's a great story teller so it opened a whole new world of fantasies for us and I'm so glad I did it.

I think your man's just a little shy, rub him the right way (ahem) and I think you'll be pleased with the results.

Answer 5

Do you know why he cross-dresses? Is it a gender identity issue or is it for sexual pleasure?

It's great that he has someone who is so open and understanding. The best thing you can do is communicate. He obviously has a lot of issues to work out and it's great that he feels comfortable talking to you. It might be best if you kept the relationship at a friendship level while he tries to figure things out.

Best of luck to both of you!

Answer 6

Your opening comments say it all. "You love him, You want a lasting relationship, His cross-dressing does no-one else harm."

Most couples use something to spice up their love-lives. Dildos and vibrators are now talked about openly. Some couples indulge in spanking, bondage, role-play, etc.

So why not cross-dress?

Sit down and talk about it. Help him to get some basic items of clothing that turns him on. Does it help him? It might even turn you on!

Take it slowly and see how it develops.

You might want to look at the website of the Beaumont Society or a specialist cross-dressing shop, such as Transformation.

Good luck

Answer 7

Hello,

First of all, the percentage of cross-dressers who are gay is the same as the overall population - about 10 - 11 percent. So if your boyfriend is with you, instead of a man, he is probably straight.

Also, there are many different kinds of transgendered (TGed) people, but people try to lump them into "main" categories: crossdresser, transvestite, and transsexuals.

A crossdresser is quickly described (and not very accurately, btw) as someone who likes to dress more for 'fetish' reasons. I have never met ANY TGed person who did not really start out this way. Some stay this way, and others figure out that the feelings are deeper than just dressing for sexual pleasure.

A transvestite is described as being similar to a crossdresser, but closer to a transsexual. They do not dress so much for sex, but they must dress. They will never become a true transsexual - at least in the eyes of transsexuals since they will not get a sex-change operation.

A transexual (TS) is someone who feels they were born into the wrong body. TS people can be male-to-female (MTF) or female-to-male (FTM). A TS feels that they must live as their true sex, and most of the time this includes getting the full sex-change operation. However, there are many who are trapped in their lives for one reason or another and cannot live in their true gender full-time...

The majority of TS people are attracted to the opposite of what they consider themselves to be, for example, a MTF is usually attracted to a male.

Now, back to your boyfriend... I do not know what his age is, or his past history of crossdressing. For example, some start "dressing" as early as 3 or 4 years old - long before sex has anything to do with them. Many TGed people are well into their 30's before they ever actually even try to have sex, because they are afraid of how their potential partners will react - keep in mind, their entire lives can be completely RUINED if family, friends, or coworkers found out about them! Secrecy is a MAJOR deal! The fact your boyfriend has told you about himself shows what honesty and courage he has! It also proves how much he trusts you!

As for his sexual performance - most TGed people don't realize this until too late, and it usually takes years to figure this out - they MUST feel (at least in their head) like the sex they wish to be IN ORDER TO HAVE SEX!!!! Dressing in bed makes it much easier to do that but if the partner knows this (which 99-percent never do) they can make things happen without dressing - at least, without dressing as often! Your boyfriend is probably having a problem because he isTRYING TO FEEL LIKE A MAN while he is having sex!!! If he can feel female (at least in his head) he will not have a problem!

He will also probably be a very giving lover to you in bed! YOUR biggest problem will no doubt be trying to get around the fact of how HE "feels in his head".

How do I know all this? I AM a dreaded "TS" (MTF), am NOT attracted to men (don't even understand WHY other women are!), and I have been through all of this!

I wish you both only the best!

Britt

Answer 8

You sound like a very nice, understanding person. But if he really has a problem of that kind, YOU are not going to 'fix' it. I mean if he represses his true sexuality or something, nobody can figure that out but himself. So I guess you can try to help him and be with him, but there's not a whole lot you can do...

Answer 9

Best thing I can offer is just play around and experiment! Sounds like you two could have a lot of fun in this area. I say work on removing the fear and trepidation first, then go for it!

Answer 10

What was wrong with the answers you got yesterday? You still seem to equate tranvstitism with being gay - it's not.

You need a counselor to help you both sort this out - not Yahoo! Answers.