Crossdressing and dating?

Lily · Post by **Lily** » Thu Mar 04, 2010 12:11 am

I would love some help coming to terms with being a crossdresser and dating women. This place has become a new home and I was hoping someone could give me some advice.

I’ve been dating since I was 15. For the few years between 17 and 19 I didn’t do much crossdressing. I didn’t think it was right since I liked dating women. Funny thing is the girl I dated during that time probably would have been okay with it.

Then I didn’t date for a while after I turned 19 and she and I split up. I thought, well I like dressing like a woman but I’m not gay. There must be something wrong with me. Then I met the woman who would later become my wife.

We moved in with each other then one day she came home and found me playing with her panties. She thought it was cute and took me out to buy my own. Then she bought us matching nighties. Then she bought me my own stockings and later dresses. Sadly she and I got divorced over other things. It was the right thing to do but I will always be thankful to her for helping me to feel okay with who I am.

The next girl I dated failed the test. You know how it works. I would throw out hints and she answered them in such a way I knew she wouldn’t be able to handle it.

Then there was a girl who loved it, but thought it was only a fun game and one night when she got mad at me she threatened to tell my friends and I knew it was over.

Then I met someone I was sure would be okay with it as she seemed to want to be as manly as I wanted to be fem. But believe it or not being with me opened her eyes to what she wanted. She wanted a man she could use as a role model and I guess that wasn’t going to be me.

The next girlfriend wanted me to keep it to myself but was okay with my dressing for Halloween. That just left me dressing when I knew I was going to be home alone. After a while we just decided we were too different.

Then there was another who made a few comments about crossdressers after we had been together for a few months and I knew it had to end.

Then I met the wonderful woman I’m with now. But again she’s okay with my dressing as long as she doesn’t have to hear about it. If she does bring it up she sounds like she finds it funny. It’s a shame because I really want to share it with her. I would love to go shopping with her. Do each other’s make up. The other day I told her I wanted to take her out to get Mani/Petties but she just smiled and ignored me. Then said she was going to get a Mani/Petty with a friend that week.

It felt so easy with my ex-wife. Now it feels like such work. I am really happy to have this forum to talk but oh how I wish I had someone at home who understood.

Absaroka · Post by **Absaroka** » Thu Mar 04, 2010 8:14 am

I think it just comes down to what you can be happy with. My wife doesn't participate at all, which truthfully is fine with me.

Most couples have stuff they don't do together. When is there too much of that is a personal decision and one persons answer will not be the right answer for someone else.

I think because crossdressing is unusual and often somewhat sexual that there is a pressure to share it with our wives. It's not like golf for example where we go off with our friends while our spouse does something else. But here is an interesting question. Why not? If it is not sexual, why shouldn't you have a gal pal to do this stuff with, even if your gal pal is another CD?

Of course some folks don't believe in having friends of the opposite gender (whatever that may be for us)

once we are in a relationship. But my wife and I have always had opposite sex friends, we named our daughter after one of my wifes male friends.

Zari

Post by **DonnaT** » Thu Mar 04, 2010 9:00 am

I don't have much experience with dating. My wife is the only person I've ever dated.

Seems to me you've had a lot of experience. The only thing I can suggest is being up front right away. If you are looking for a long time commitment.

Leeza · Post by **Leeza** » Thu Mar 04, 2010 9:38 am

I was talking to an ex gf from my school dayes last night.

I had talked to her about 20 years ago and at that time she had commented that I was the only guy she had dated that her folks had liked. I told her then that if they had realy known me they probably wouldn't have liked me either. They belonged to the same church that I was raised in and I was asked to leave because I was doing things that the church didn't agree with (other than cd as no one knew).

I have never told her that I was a cd. At the time we were dateing I thought it was something I could put away and not have to deal with. By the time I was talling to her 20 years ago I knew better.

The funny thing is that if I hadn't been asked at work one day if we were engaged we would have probbly been married. I realy figured that I would ask her to marry me, but was not ready for that at the time. When I talked to her about 20 years ago I found out that she had commented to a mutual friend that she wanted to marry me and it had gotten changed to we were engaged by the time I heard it.

At this point in time all she knows is that there is something about me that the church she belongs to will not accept. I wouldn't go any further into the conversation than that last night. Maybe someday I will tell her if we ever have the chance to get together for coffee, but it is not something I would tell her over the phone. Even over coffee I would try to read her before going too far.

Leeza

Rik · Post by **Rik** » Thu Mar 04, 2010 11:30 am

Im in the same boat lily, and its a tuffy.

My last GF new I liked any exucse to wear her underwear, which in turn I also knew frieked her out, as you did, I also dropped hints that this was more than just kinky fun, she didnt like it,and untimatly we split.

I am very eager to find someone to share this with and have fun with, and I strongly belive that the right person could have loads of fun with it.

Theres a girl I know who has admitidly fancied me for years,although I dont find myself arrtacted to her physically, but we always get on so well when we chat. She recently split with her current b/f whom she has a child with, and she txts me 6-8 times a day, I told her bout my dressing few weeks back, and she loves it,she cant wait to do my makeup in fact.

This person becomes more appealing to me daily, is this because she accepts me and im just lookin for some1 to have fun with? or are feelings emerging?

Its never going to be easy, and always risk involved, but just be yourself from the get go, no 1 can ask for more!

Laura Bird · Post by **Laura Bird** » Thu Mar 04, 2010 11:56 am

Analise wrote:Im in the same boat lily, and its a tuffy.

My last GF new I liked any exucse to wear her underwear, which in turn I also knew frieked her out, as you did, I also dropped hints that this was more than just kinky fun, she didnt like it,and untimatly we split.

I am very eager to find someone to share this with and have fun with, and I strongly belive that the right person could have loads of fun with it.

Theres a girl I know who has admitidly fancied me for years,although I dont find myself arrtacted to her physically, but we always get on so well when we chat. She recently split with her current b/f whom she has a child with, and she txts me 6-8 times a day, I told her bout my dressing few weeks back, and she loves it,she cant wait to do my makeup in fact.

This person becomes more appealing to me daily, is this because she accepts me and im just lookin for some1 to have fun with? or are feelings emerging?

Its never going to be easy, and always risk involved, but just be yourself from the get go, no 1 can ask for more!

True love doesn't always include physical attraction at the very start.

Of course making the choice to date a friend is always a sticky one, but over time, who knows?

Lily · Post by **Lily** » Thu Mar 04, 2010 12:01 pm

My SO is not the girl I would have gone out looking for. But we were friends and it went from there. We've been together for years now.

Virginia · Post by **Virginia** » Thu Mar 04, 2010 9:01 pm

Lily,

You are a walking billboard for the fact that "it doesn't go away!"

Finding someone who can "live with it" is at best, difficult and an SO that will not only live with it but participate (to varying degrees) can rock our world, so to speak. They are few and far between, but as my sisters have said, it may be tough on us emotionally but it is best to be honest up front in the relationship as we have seen the results of trying to hide it and then getting caught 2 - 5 - 10 + years later.

No one here will tell you how to manage your relationships as they come along, but I think you are doing it "by the book."

Good luck, hon and keep the faith.

Love,

Virginia

Lily · Post by **Lily** » Thu Mar 04, 2010 10:12 pm

Thank you very much, all of you. I often wonder if there are things I can try to do to help her with who I am.

Gaven McLaren · Post by **Gaven McLaren** » Wed Mar 24, 2010 9:04 am

It helps if you are dating a friend that knows first then become a couple. That is my current situation. I recently started dating a lovely girl that was my friend first. She is very cool with it and has even insisted that I try one a dress that she brought over the last time she was down. I am taking it as slow as she is allowing me to.

SharonRose · Post by **SharonRose** » Wed Mar 24, 2010 11:18 pm

Lily,

Honesty is the best policy. A relationship needs to be built on trust.

That being said, I respect the fact that some people keep this a secret from their SO, out of fear of rejection. Also, times were different years ago.

I told my wife that I was a CD shortly after we started dating (which was 7 years ago).

One of the things I did to help explain to her what this was all about, is to give her the book "My Husband Wears my Clothes" by Peggy Rudd.

That, and allowing her the time to process all of this new information about me.

She has been very supportive, attending support group meetings with me and accepting the fact that I like to go out dressed from time to time.

We don't go much else together while I am en femme, other than attending events put on by the support group.

There are different levels of acceptance that we can experience from our SOs, and I feel fortunate to have what I have, even though there are times I wish for more.

I try to remember to keep my priorities in order, to allow time to nurture my relationship with my wife and kids.

One other thing to think about is not to give up. "No" may not mean "Never", it can just mean "No for now". People can change their minds over time.

I hope this is helpful.

Sharon

Hope · Post by **Hope** » Thu Mar 25, 2010 12:08 pm

Oh Jeezzzzzzz.....I should keep my mouth shut?

I have to say though, marraige is sort of like really good wine. If it's good when it's first bottled, over time it becomes just fantastic!

Unfortunately, CD'ing is also like wine. Once it's opened, you can't close it up and have it keep very long? Ok...poor analogy. But, I think we all realize it's a facit of our personality that just is. It won't magically go away once we are married. In fact, I think in the vast majority of cases, as we age, it just gets stronger.

It's so hard to know what your SO will do, just as it's hard to know what your own brain will do over time. My first wife knew well before we were married about my hobby, and was cool with it until 15 minutes after the wedding. Suddenly, she changed dramatically and for the longest time, I thought it was just my own brain having trouble adjusting to being a married man? (Old stupid here didn't figure out for 23 years that it was her that changed, not me!)

My current wife was also told long before we were married. Over the past decade or so (well....longer that a decade maybe?

) she has supported me in my hobby more than I could have fantasized about....ever! To her, it's part of who I am. It may be the thing that made me kind, gentle, whatever....but it's just part of what made me who I am. And she likes who I am.

So what was my point? I have times I don't particularily like the idea of wearing a dress. But I have other times where I don't want anything to do with pants or 'man' things at all. That won't go away. It just is. And I believe life is too short to be unhappy. We don't have that much time here....me or my lovely bride. Why should either of us be unhappy. I don't want to hide something from her anymore than I would like her to hide her feelings from me. I like open!

Now, I grant you I would have hated to miss one day of what we have had in our marriage, but I'm not sure it would have been the same if we compromised on something as personal to either of us. Or....maybe I'm just a really lucky stiff who should keep his mouth locked up tight?

All my best wishes for you.....