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I Told My Girlfriend That I Crossdress

March 10, 2012

During high school, I had a few different girlfriends.  There were also some girls that I went on dates with but never really became boyfriend and girlfriend.  The last girl I dated in high school was different.  Our relationship was different.  We dated a long time, I told her, “I love you.”  I had with her the deepest relationship I had ever had with a girl so far.  Eventually, I decided to tell her my secret.

Sometimes, a crossdresser will start getting the notion to “come out” to someone.  I think the drive to do this is similar to the notion we get to try some new garment, or to go out in public, or to advance our crossdressing in some other way.  However, I think I wanted to tell her for other reasons.  It was not for a thrill or a turn on.  I was confessing.  I did not like being a crossdresser.  I had been fighting it for years, but enjoying it when I would give in.  I told her.

I presented it to her as a problem that I have.  I communicated what I would do.  I was open and honest, I believe.  She cried.  She needed some time to process it.  The next day, we had a talk.  She told me that I should stop and if I could not stop, I should get help.

I stopped.  I don’t know how many months I stopped for, but I tried.  I was not sexually active.  My crossdressing was the only technique that I had for attaining sexual release.  Therefore, when I stopped dressing, I stopped gratifying myself.  I have grown to believe that the stuff a man makes is not supposed to stay inside.  I believe that when it does not come out, the body starts to increase the hormones or something in the blood.  It basically drives a man, or at least me, crazy.  I had denied myself my only outlet.  Therefore, the cravings to dress grew and grew.

Eventually, I gave in again.

But, I don’t want to go in that direction.  The relationship with the girl and her knowing my secret was the point of this story.

That relationship, like almost all high school romances, eventually ended.  And, like so many high school romances, it ended badly.  I have grown to believe that women do not like breaking up.  It makes them angry.  And what is an angry, hurt girl to do when she has a mega secret about a guy??  I think she told some people.  I think she told my best friend and a girl that I liked.  Fortunately, they did not easily accept her story.  I figure if someone told me something negative about my friend, I would not believe it easily.  However, I would not forget it and I would hold onto the information and pay attention.  I have never talked to that friend about my crossdressing.  Perhaps I will never know for sure.  I know that if I ever run for president, she will be that girl in the headline “Former Girlfriend Tells All”.

The moral of this story is think twice about telling a girlfriend that you crossdress.  If it is a big secret and if you are not planning on asking her to marry you, then think hard about it.  Perhaps ask advice from an online friend or someone who you know in real life who knows your secret.  Ex-girlfriends can be a bad people to know your secrets.  But, in the middle of the romance, they seem like such good people to tell secrets to.

However, I believe that you should strongly consider telling your girlfriend that you crossdress or any other secrets before you ask her to marry you.  Let her decide with her eyes open.  Also, don’t downplay it.  If you cannot be open and honest, then in a few years when the whole truth eventually does come out, you might really hurt your wife and your relationship.  I have come to believe that women value trust very, very highly.


From → True Stories

  1. Sheila permalink

    I told and showed my other self to a wonderful girl. I was in bra and open bottom gridle with nylon stockings and my mothers high heels. She said she loved me for trusting her! … She said she was pursuing a particular man but would continue our relationship and help me with crossdressing until she got him. … It was great until I met my wife. … So problems popped up. I wasn’t allowed to spend money on this or that and on and on. So we parted. I then met another wonderful woman! She saw me buying pantyhose and a dress. She said she knew right away I was crossdresser, but she saw the real me during that time at the store. We are still married and now I am retired and dress most days!

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