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Wicked1 · Jul 22, 2009, 02:18 PM

Ive been dateing this guy for a few weeks now and I was told prior that he crossdresses... It don't bother me but I kind of want to know out of his own words. What would be the best way to say something to him? Or should I not say anything at all? I had another boy friend prior that crossdressed and the only problem I had with it was that he always stole my clothes and make up?? What should I do?

Torrid13 · Jul 22, 2009, 02:22 PM

You've only been dating a few weeks---give him time to get comfortable to the point where he feels he can tell you himself.

Don't push the subject on him.

DrJ · Jul 22, 2009, 02:30 PM

You had a previous boyfriend that was a cross-dresser and now your current boyfriend is also likely a cross-dresser. What are the odds?

Anyway, yeah, he may not be comfortable or confident enough to admit that to you. Give him time. If ever broaching the conversation of ex's, maybe slip in there about your cross-dressing ex-boyfriend and how you didn't care other than the fact that he would always steal your clothes. Maybe your shown acceptance of the scenario will help him feel a little more comfortable in telling you.

Careful not to make it obvious or awkward, though... that could backfire on you.

Wicked1 · Jul 22, 2009, 02:40 PM

Originally Posted by DrJizzle

You had a previous boyfriend that was a cross-dresser and now your current boyfriend is also likely a cross-dresser. What are the odds?

I know I just know how to pick them right

N0help4u · Jul 22, 2009, 03:21 PM

Maybe hand him some tights and see how he reacts and then do like DrJizzle said.

Torrid13 · Jul 22, 2009, 03:26 PM

Originally Posted by n0help4u

maybe hand him some tights and see how he reacts and then do like drjizzle said.

Roflcopter.

DrJ · Jul 22, 2009, 05:29 PM

Originally Posted by N0help4u

Maybe hand him some tights and see how he reacts and then do like DrJizzle said.

Hahah... that actually could work! Just toss him some tights and tell him you were out shopping and picked them up for him.. just like it was no big deal lol

MarkwithaK · Jul 22, 2009, 06:10 PM

Originally Posted by DrJizzle

hahah... that actually could work! Just toss him some tights and tell him you were out shopping and picked them up for him.. just like it was no big deal lol

That could work... or it could cause him to go on the defensive and close off that part of him all together. Next time you two are having a roll, tell him you think it would be hot if he wore your panties... see what happens.

N0help4u · Jul 22, 2009, 06:13 PM

Yeah if she laughs it off and act like SHE does that in general and no big deal to her. It could work in some situations with a guy that has a good sense of humor.
But you are right it can put some guys on the defensive.

Torrid13 · Jul 22, 2009, 06:14 PM

Are you interested in cross-dressing yourself? Maybe if you dressed up butch, or showed that you are interested in cross-dressing, too, it could turn into something highly erotic for both of you.

Fr_Chuck · Jul 22, 2009, 06:34 PM

You are just starting to date, there is no need or even should not be any telling each other everything.

First how do you know?? Sorry are you standing outside his window watching him ?

I find your post hard to believe, but honest it is not something you have the right to hear from him at this point in your relationship

Gemini54 · Jul 22, 2009, 09:56 PM

Does it really matter to you if he crossdresses or not? As it's only been a few weeks, I'd leave it for a while and see how the relationship unfolds, rather than pushing the point. It is his business after all, not yours.

After a few months perhaps leave a few of your cutest lacy undies on the bed and see if they disappear...

Alty · Jul 22, 2009, 10:08 PM

I have to agree with the others, this early in the relationship he's probably not comfortable telling you this.

Give it some time. I also like Dr. Jizzle's idea of mentioning that you're ex was a crossdresser, that may open up the lines of communication.

This is a lot like telling someone how many partners you've had. You don't bring it up until later in the relationship because it's really none of their business early on.

Good luck.

Wicked1 · Jul 23, 2009, 08:32 AM

Originally Posted by Torrid13

Are you interested in cross-dressing yourself? Maybe if you dressed up butch, or showed that you are interested in cross-dressing, too, it could turn into something highly erotic for both of you.

I kind of dress in guys clothing now cause my ex stole most of my clothes so I went on a defence and bought a bunch of baggie clothes and nothing girly... but the guy I'm with now is insisting that we go shopping and get me girly clothes...

Wicked1 · Jul 23, 2009, 08:35 AM

Originally Posted by Fr_Chuck

you are just starting to date, there is no need or even should not be any telling each other everything.

First how do you know ???? sorry are you standing outside his window watching him ?

I find your post hard to beleive, but honest it is not something you have the right to hear from him at this point in your relationship

Ive known him for a long time now and we just been officially together for a few weeks.

I know buy what a past girl friend has told me and a past room mate... and there are some tiny little hints that get said but nothing major

N0help4u · Jul 23, 2009, 08:43 AM

Well the bottom line is whether he ever lets you in on it or not you have to decide if you are comfortable enough with him, knowing he is doing it or does it negatively affect your relationship with the fact that he does this.
Is it something you can live with whether he confesses or not?

Holly23 · Jul 23, 2009, 08:50 AM

I haven't read all the replys,just wanted to ask where the hell do you keep meeting all these cross dressers!

Wicked1 · Jul 23, 2009, 09:14 AM

Originally Posted by N0help4u

well the bottom line is whether he ever lets you in on it or not you have to decide if you are comfortable enough with him, knowing he is doing it or does it negatively affect your relationship with the fact that he does this.
Is it something you can live with whether he confesses or not?

I can live with it if he tells me or not. It don't bother me at all. I just don't want him thinking that it would ruin our relationship.

smoothy · Jul 23, 2009, 10:21 AM

Most likely its just a rumour, many people say things that are untrue about others.

If you are fine with it, don't sweat it, if its true, eventually you will know... if it is in fact false, he might get highly offended if you bring it up, particularly this early in a relationship.

jenniepepsi · Jul 24, 2009, 01:06 PM

I deifnately agree that dropping hints about your ex, and see where it goes. He may be uncomfratable and not ready to come out with it to you yet.

Good luck hon.