Ask Dan & Jennifer

Hi there, SG

I'm also a crossdresser and can relate to you almost completely. All that separates us is that I'm a virgin and haven't had a girlfriend yet.
I can still, however, understand how you must be feeling about your dilemma. Even though you're deadset about telling her with your very wise truth policy, don't spill any beans just yet. You have no idea how she's going to take the news when you tell her. If she's as open and warm in er sex life as Jennifer then you know that it's going to be a smooth ride all the way through. Contrasting that possibility, if she's got any prejudices against any male homosexuality (and relates crossdressing closely to it) and doesn't like any nasty surprises, you may find yourself on don'tdatehimgirl.com, leaving you exposed for all to see.

Some women take it horribly from day one straight through to whenever she last sees you.
Some initially take it badly but come to condoning it, perhaps even straightforward accepting it sometime after.
Others may be really aroused by our intriquing hobby.
And, of course there can be different levels of emotions throughout those three possibilities. Those are the three main outcomes, though there would be others tailored to the woman and the timing.

Because I'm on your level age wise and probably in the way of crossdressing itself, you should join me on a very resourceful and relieving website that will guide you through any of your crossdressing queries and maybe even your partner, whoever she may be at any given stage. It's exactly like this website, but purely for and about crossdressing of all levels. This is the most advice you could ever recieve on this one.

crossdressers.com

Hope to chat to you soon

Matt

Thanks Matt.

I checked out the website that you suggested and found a very good post on this topic.

"How To Tell Your Partner"

I found it very informative on the topic of how to introduce the topic to your girlfriend.

One of the biggest things I liked about this article is that you need to make sure that you can accurately answer her questions about what crossdressing is and is not. And where you fit on the scale.

I do agree that you need to be completely honest with her - but where and when and how much you tell her depends, in my opinion, on how big your cross dressing fetish is? Is it something you do occasionally? All the time? Is it full dress with makeup and the whole 9 yards, or do you just like women's lingerie?

Make sure that you really understand yourself in this area before you try to share it with her.

No worries, guys. It's a very useful site, isn't it? So glad I found it.

Hey, Jen. Have you asked Dan to do any feather dusting, yet? lol:D

i put her panties on and her skirt and just told her, if she leaves it better u find one who accepts it. it will be better and easier. mine accepted it

as along time panty wear er and crossdresser i will say dont just throw this at her take your time if your dateing a girl you think might be into this play it off as you one moring accidently put hers on when getting out of bed she her reactions . if you get hard in them she may like it if she asks you tell her you feel harder in them.

many feamles have diffrent things they like. you never know its its treid but do it with taste or make a game of it

I'm not really sure which way is better to tell your girlfriend. If I were her, I would definitely appreciate you explaining everything. It would make everything clear and nothing left to imagination, in case if there were any misunderstanding if you slowly hinted at it. However, the communication in the relationship has to be good enough. Dan's way feels like it's more of beating around the bush, which is a good way to get a general feel of how she feels before you sit down and talk (just something to keep in mind is that she might be able to sense something is going on before you talk to her).

He peeps, I totally agree with Jennifer on this. Most women would respect a man for being open and honest. As it takes alot of courage and guts. Yep a good old fashioned heart to heart does it for me anyday.

Good advice Jennifer, it is good to see someone with a bit of common sense around the place.

She might surprise this guy and want him to show her his credentials as a woman lol? She might like having him in this feminised state? Some women love it and it makes them very aroused and horny lol!

My views.

Regards.

Tenderkiss.

I went on a date with a guy I met online a couple of years ago. He seemed like a wonderful guy online, worldly and smart. We talked about everything but sex. It wasn´t the time for that yet.
When I met him I was so surprised; he was a weakling in every scene of the word. But I didn´t leave before he got undressed and was wearing a pink corset and high heals. That´s not the way to go! Always talk about it first!

I think there is more depth to this question than is apparent on the surface. At what point do we share information with people that may make them uncomfortable. D&J made some great points about the need for discretion. I can see where sharing this information too early could cause a person to prematurely abandon a relationship that could turn out to be very beneficial for both parties. I think DarkMist makes a great point, too. I think it would be very unfair to, for example, marry someone without them knowing that you like this activity. I have read many posts on these forums from women who have found that their husbands were involved in activities that they considered "deviant." The sense of hurt and betrayal permeated the posts.

This is an area where we will all be seeking balance long after this post is history. I think the guiding principle needs to be that it is unfair to let someone make a major decision without access to information that could impact their decision. The woman is eventually going to find out that you crossdress, and I think it's better for her to know it upfront than after she's in a committed relationship. If she is accepting of the behavior, she will wonder why you didn't trust her enough to share it with her. If she can't accept it, she will be angry for hiding it for her. Either way, she will wonder what else you were hiding from her.

A rule of public relationships is that when upsetting news has to come out, it's always better for them to hear it from you. I probably wouldn't tell someone I was seeing casually, but as DarkMist says I think it would be unfair to spring something like this on someone late in the game. I think this issue calls for careful consideration and balance applied to the specific situation.

Another issue underlying this question is the topic of compatibility. If someone can't accept this part of you, which is obviously a big part of who you are, then you need to accept that she isn't the right person for you. You don't want to be married/committed to someone and living in fear of them finding out about this. You deserve to be with someone you can feel free to be your real self with. If you have to hide a part of who you are, then the relationship isn't the right one for you. You deserve someone who loves you for you. Therefore, if she can't handle it, it's better to find it out before the relationship goes too far.

I want to thank you for bringing this issue up on the forums. It is a very delicate issue, and I'm sure this won't be the last post about "When do I tell him/her.....?"

You should listen to Beagle, especially about a person being right for you or not.
Personally I would not might having sex with a transsexual. I haven´t done that yet, so why not. But nothing is attractive when forced on another person.