My first time...

[Kara]

I bet I was around eleven. My brother was older than me and had Playboy and Penthouse magazines hidden under his bed. I used to look at the pictures. Then started reading the columns. Especially Penthouse's Xavier Hollander. The stories that caught my eye were ones where girlfriends or mistresses dressed their partners up in woman's clothes. Intrigued me.

But what started me was a story in Playboy called Voyages of a Mile High Fille De Joie. Remember parts of the story. But there was this illlustration of this beautiful reclining woman dressed in a corset, stockings, flowing, frilly nightgown.
Actually found the image here http://www.giantess.net/files/filledejoie.jpg" onclick="window.open(this.href);return false; (copy and paste the link in your browser)

I just wanted to know what it was like to be her. The stockings looked so sensual. I don't think I acted on it until I saw another pictorial in which one of the women said "I am a woman and enjoy being one." That always stuck with me.

After that I looked in my mothers drawers and found a basque with garters. No stockings, so I cut the legs off a pair of pantyhose. I loved the feeling. She had high heel boots but they did not fit me. Being a horny pre teen I learned about pleasuring myself. After that I always dressed in something when I masturbated.

After that I would wear what I could under my clothes. Doing my paper route. I dreamed of coming across an older woman who would dress me and make me her girlfriend.

I had no self confidence at this time in my life. Before or since. I was always picked on, called names by my brothers and neighbors - fag, wussy, wimp. Wasn't good at fighting so I think I retreated into crossdressing. Which probably didn't help my confidence since I was always afraid of people would find out and beat me up or humiliate me.

When I could drive I would go to stores 2-3 towns over and buy or steal (yes I stole a few things) stockings and garter belts. I wasn't into bras. Woolworths had great cotton garter belts.

When I was younger I used to dream of being a Playboy bunny. I didn't find out about transgenders until I was in college. But I dressed on an off until then. I didn't dress at all senior year in college.

I have been fighting crossdressing for the last 30 years. Sometimes I can go for months. Sometimes can't go for a day. A lot of the feelings I see others have. Guilty, feeling weird. Worried someone will find out. I'm married with kids. My wife made it clear she is not on board with this so I hide it from her. Have for years. My family would never understand.

Now being out of work I find myself dressing during the day when no one is home. I don't know if I want to be a woman, a lesbian, a crossdresser, or what. I know almost everytime I dress I end up masturbating. That is how I take the clothes off. Been that way for years. So is this a fetish? I went to a psych who told me I probably dress to relieve stress. Other than that she didn't help much.

I wish I had never started this. I just want this to stop controlling me.

I am dressed as I write this. Corset, pantyhose, heels skirt, blouse. It feels so nice! I really love undergarments from the 40's and 50's. Girdles, corsets, corselletes are my favorite. Love curvy woman. I love looking down and seeing my breasts. Wearing high heels. Tight pantyhose. Stockings. I love the feeling of being constrained in real tight shapewear.

But I could never pass. When we were expecting our first a coworker said to me "Hope it's a boy. You're a good looking guy but you'd make a lousy woman". And I am over six feet.
When I dress I don't like looking at myself. I don't want to see a man in a dress. And neither would the general public.


I didn't mean to go into all this.

[Anthony Simon]

I wish I had never started this. I just want this to stop controlling me.

You wrote a very honest post (though probably a bit explicit for this site), but this jumps out at me. From the rest of what you say, I have the feeling that you'd like to go further into the CDing and are not sure what would happen.

Like the sense in which you feel out of control is that your urge to CD seems to be taking you beyond the limits you know about. I have that problem with it also. My instincts are telling me that a deeper engagement with it would be a good thing for you (FWIW). So I guess your problems are to do with how it would fit into the rest of your life, fears about other people finding out etc..

[Davita]

Hi Kara,

One thing caught me, "'Hope it's a boy. You're a good looking guy but you'd make a lousy woman'. And I am over six feet."

Two things? Anyway, A good looking guy tends to make a good looking woman. So I have to ask what makes you a good looking guy that particularly won't make you a good looking woman? Over six feet? Ummm can you say gorgeous volleyball player? Every time I put on my heels, I'm over six feet. No one hollers out, "hey you're not a woman because you're over six feet." Heck if you're worried that much, find some tall friends. Height is not an issue.

[Kara]

I was trying not to be explicit, but didn't know how else to phrase it.

I don't know if I want to go farther. I kind of got myself addicted to internet porn. Particularly transgender and lesbian sites. Started with magazines, then videos, now internet. When I went to the counselor she seemed to think the internet porn triggered my desire to dress up. But I realized the other day that my dressing up triggers my desire to look at porn.
And when that happens hours go by.

I know when I dress up I feel like doing things I would not normally do. I am afraid I will do something that would get me in trouble.

I fantasize some woman would find out what I am wearing and we would have sex. (Probably from all the stories I have read.)
But I haven't cheated on my wife and don't want to.

I know this. My senior year in college I didn't dress at all. And that was a good time in my life. I had friends. I was working towards my career (which I never went into). So do I dress in response to not being happy or where I want to be in life? I don't know.

If I was not married I might take it farther. But I don't want to hurt my wife or family.

As for my looks. Big head, big ears, big nose, wide jaw, wide shoulders. None of which are very feminine.

[DonnaT]

Thanks for sharing.

I wish I had never started this. I just want this to stop controlling me.

I am dressed as I write this. Corset, pantyhose, heels skirt, blouse. It feels so nice! I really love undergarments from the 40's and 50's. Girdles, corsets, corselletes are my favorite. Love curvy woman. I love looking down and seeing my breasts. Wearing high heels. Tight pantyhose. Stockings. I love the feeling of being constrained in real tight shapewear.

Those two paragraphs seem contradictory to me.

As for the first, I reckon by now you know that this is a part of who you are and will always be a part of you. All I can suggest is don't try to fight it, accept it and it will become less stressful for you.

[Anthony Simon]

Kara, my feeling is your central problem is your wife "who is not on board with this". It may be that while you were in work your desire to CD was controlled but, now that you're not, it's ramped up and you fear discovery.