I love summer!

The sun, the beach, golf, sailing, I even enjoy mowing my lawn. Planting my garden, watering and tending to it, the Black Eyed Susans taking over the front garden. Sunflowers growing tall and waving in the breeze.  I love looking out my window into my backyard and seeing the green grass.

However, my wife is home for the summer, that makes dressing as Jillian very difficult, I have NO time to myself. The last day of school sees Jillian’s things going into a storage container and down into the basement.

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Slowly the dysphoria builds. There are years, honestly most years, that it is manageable. This year it’s bad, really, bad.  This summer the realization has really hit me that I am not a woman, that my body is just not female. That hurts.  A lot, a lot more than it ever has, more than I ever thought it could.

Beautiful women are everywhere.  Summer is when I come face to face with the fact that I simply will not look like her in a bikini, or even that one-piece. That flirty sundress was not designed with my body in mind.  Summer clothes are tighter and more body conforming. I love the look, but I can’t pull it off and it kills me.  I have learned to observe other women with a mix of admiration and envy.  A part of me is learning, watching how women move, stand and gesture. Another part of me is envious, wishing that my body looked and moved like that.  I don’t have a pair of breasts gently bobbing in my bra or a narrow waist or a round bottom to fill the tight shorts or the long tan legs … well, you get the idea.

There are times when I could scream at the sky in frustration, “It’s not fair!  Why don’t I look like that?”

But then, who says life is fair?

I know, some of you will think that I should just come out and then transition.  Use hormones and surgery to change my body, to try to look like the girl I wish I had been born.  That’s out of the question for me.  My wife knows that I am a cross dresser but is not at all supportive.  She has let me know in no uncertain terms that our children should never know this side of me.  My family means everything to me, so that’s that.

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I didn’t grow up as a girl and no amount of chemicals or surgery will give me the years I missed as a girl back. My room wasn’t pink with a closet full of frilly dresses.   I didn’t have tea parties with my with dolls.  My mom didn’t spend evenings brushing my hair.  I never had a slumber party with my girlfriends where we played with our makeup or our hair, gossiping about our latest boy crush.  I never bought a prom dress.

I have never felt the dysphoria this strongly before.
Could it be getting stronger as time goes by?
Am I the only one who feels this way? Is it even possible I’m alone in these feelings. There must be others who feel as I do. The regret, the feeling I missed something important. The immense sadness that descends and takes root in the depth of my soul.

Then, when I do have the opportunity to dress, I look in the mirror and see an imposter, a faux woman and I hate myself. I tell myself  “You didn’t earn the right to wear this dress! You haven’t put in your time. You haven’t experienced life as a girl and a woman”. Instead of easing the dysphoria, the discomfort increases. I’m in a no win situation, I see no escape.

To think all this angst and soul searching because a pretty girl walked by me on the beach.

Thank you girls for taking the time to read my story and feel free to send in a response to my story or  an answer to one of more questions I’ve posed to you below:

  • Is your wife totally unaccepting of your desire to cross dress and do you have to stay in that cross dressing closet and keep all of your femme items hid from her?
  • Do you always wish you were born a girl or does your cross dressing give you the satisfaction of being a girl while getting your total girl on as a cross dresser?
  • When you first told your wife about your thrill of cross dressing and she was totally unaccepting, and then after you had “The Talk” with her telling her how your cross dressing was intrinsically linked to your overall happiness and mental well being, did she gradually come around to be more accepting of your thrill of cross dressing?

Thanks again girls and I look forward to hearing your responses.

Sincerely, Jillian




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I’m an off and on crossdresser that right now is more on than off. I am now 66 years old, married with 3 grandchildren. My lifestyle takes a backseat to the needs of my family. In the last few years I have let the girl side of my personality breathe a little more. I joined CDH to stay in 2019 but took a hiatus after Covid hit. I enjoy being here. Recently I’ve become more open to the idea of being out and it no longer terrifies me.

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Lacy Satin
1 month ago

Jillian, you are not alone with your feelings. I also find it very frustrating that as I get older my dreams of being that little girl slip farther and farther away. I use to be successful in passing as a woman and have a lot of wonderful memories of being out and feeling like one of the girls. I no longer feel passable as a young girl and do not go out anymore. I’m thankful I still have a very girlie petite body and I love to take pictures of myself from behind. It excites me to still be able… Read more »

Brianna Rizzoli
1 month ago

Jillian: First let me say that I LOVED your article no matter how serious and sad it made me. You threw out some blunt and honest feelings for us to hold with you and you had the courage to lay yourself naked before us. You are one very special Lady. Bare with me as the following is not short… Oh My!!! Jillian!!!! That was a powerful read. My heart aches for you. Especially when I read about how you look in the mirror and get those negative emotions running through you. I do not share that level of dysphoria with… Read more »

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