I have never posted about this part of my life before. I did try to register at Crossdressers, but it did not work for some reason. I am not transgender, but I am a crossdresser—something I started more than half a century ago. There was a long stretch when I did not dress, but lately the "pink fog" has come roaring back.
Thinking about how it began brought back early memories. When I was about four or five, my parents would tell people I should have been born a girl because I was "too pretty" to be a boy.
I once found red lipstick and smeared it on, and my mother put my blonde hair in curlers just to see how "pretty" I could be. I wanted that to happen again for years, but I was told, "Boys don't do that."
I modeled dresses a couple of times so they could be altered, happily volunteered to do it again, and was told that was not something a boy should do.
I loved boys' sports, but I also wanted to hang out with girls; a little teasing from other boys was enough to make me stop.
Around age ten or eleven I began trying on pantyhose and found some nail polish. I thought I removed it well, but the light pink frost sometimes showed.
A couple of girls in my class started calling me "Petunia." I was secretly thrilled, but those girls moved away.
As puberty progressed, I no longer looked like a "pretty girl." I still wore pantyhose under my clothes sometimes, painted my nails when I could, and experimented with makeup. I was questioned about red-tinted lips and once missed a bit of eyeshadow, but I think I mostly got away with it.
Once I started working and had my own money, my wardrobe grew—mainly lingerie and sleepwear, because I could not leave the house dressed.
I bought makeup and applied it in my car, then panicked and wiped it off before getting out. I spent a lot of time underdressing and sleeping in silky nightgowns.
Eventually my father found my stash when I was in the hospital for a couple of days. He asked me about "that bag," and I pretended not to know what he meant. It held my lingerie, makeup, a stack of Penthouse Forum and Variations, and many issues of Female Mimics International—a now-defunct, Vogue-style crossdressing/trans magazine.
At that stage, my dressing was heavily fetishized, and I am sure it contributed to confidence problems when talking to women.
I met my wife when I was twenty-three, and I lost my virginity to her. She was the first girl I was strongly interested in who showed interest back—or at least the first I could tell.
Up until then, more guys had come on to me than girls. It was also the height of the HIV crisis where I lived, and gay-bashings and even killings were tragically common.
Before marriage, we exchanged secrets. She disclosed having been sexually abused multiple times by at least four men. I slowly revealed my crossdressing.
She was okay with it as long as we kept it private. We shopped together, did each other's makeup, I did infills and painted her nails, and she did acrylics for me.
She bought me lingerie and sometimes borrowed mine. I would underdress when we went out, and she would be affectionate.
We got cozy sliding stockinged legs together and enjoying the feel of lingerie before intimacy. Yet afterward I would often feel disgusted with myself and strip everything off immediately after orgasm.
One day I stopped. I looked in the mirror—middle-aged, greying, wrinkling—and wondered what I was doing.
My wife entered perimenopause and her libido dwindled, so I took out my earrings and let the holes close. For twelve or more years, that was that.
Then the pink fog returned. I did not recognize it at first. After a couple of life-changing experiences, my outlook shifted.
With a little time to myself, I went shopping: pantyhose, then panties, nail polish, and heavily tinted lip balm. I got my ears repierced, bought inexpensive jewelry and wore it daily, removed body hair from the eyebrows down, and began using feminine hygiene products. Most of this could be hidden.
When my wife noticed, she was not happy. "Why now?" she asked. I could only say that it never truly goes away and that life changes might have brought it back.
I went shopping again and bought women's jeans and big hoop earrings. That was a step too far. One pair of jeans looked way too feminine; the hoops were a no-go.
She did buy me smaller hoops—which thrilled me—and I wore a second pair of skin-tight, jegging-style jeans. My wife's friends told me I looked good and skinny; those became my first clearly feminine outerwear.
Since then I have worn panties exclusively and added a couple of camisoles, pantyhose and stay-ups, women's tees and shorts, a makeup kit, two steel-boned corsets, ballet flats, and some sex toys that, when used on myself, were mind-blowing.
My wife does not know about most of this, and she refers to my crossdressing as my "perverted kink."
With a few days alone out of town, I decided to push myself. On four occasions I went shopping in women's tops, jeans, hose, and shoes, with lipstick, concealer, and mascara. I tried on clothes in roughly ten different stores without issues. I am grateful to the younger generation for making that feel possible.
Where does this leave me? My wife asked if I want to have sex with men or go out dressed. I told her no to both. I love my wife and do not want to destroy our relationship.
Even so, I have gone out in a blended style—not fully presenting as a woman, because I do not expect to be passable. My dressing has shifted from primarily fetish to something I simply love.
I saw ads for a Halloween trans ball—presumably welcoming to crossdressers—but I am unsure whether to ask my wife about a weekend away. They offer makeup application, which I have always wanted to try but have been too self-conscious to do. My wife once offered to take me to a dressing service, but I did not have the courage. Maybe next year.
For now, I will see how it feels when I get home. I resurrected a nightie my wife gave me for Christmas two decades ago—when I cried with happiness. I hope she recognizes it, and maybe that can open a gentle conversation.
I apologize for the length, but this has been a long time coming. If you made it this far, thank you for reading—and thank you for letting me ramble. —P
