I have been crossdressing to some extent for most of my cognitive life. When I was a child, I found various items of clothing compelling for reasons I did not understand. I remember when my mother had bought me a sought-after pair of penny loafers for Easter, the day when we all wore our new clothes. I looked for them one time when she was out and, finding them, put them on and felt exhilarated.
As an adolescent, I developed a fascination for women’s accessories to the extent that even men’s items that reflected women’s fashion were appealing. The practice of wearing wide belts with the buckle at the side was common among young men at the time and I coveted the look. While I did not see it at the time, it was probably evocative of the wide belts women wore buckled in the back. At least it titillated me in the same way.
I had a very ordinary life as a young man, but occasionally tried on various clothing items and accessories that belonged to my sister or mom. What I might call my crossdressing behavior was limited to a fascination with women and the way they dressed. This was probably not much different from other young men, except that I was not only turned on to attractive women – I was turned on to their clothing and accessories as well.
When I was in college (during the 60’s) our society was experiencing a cultural revolution, so many styles became sort of androgynous. I began wearing hip-hugging pants, low-rise underwear (that resembled women’s panties) and even high-heeled boots and shoes. This seemed to satisfy my desire for things feminine. Many of those styles held for several years with tighter clothing, wide (fashion) belts, waste-length jackets, and bell-bottomed slacks. I enjoy that sort of “out-there” style for men, but I still bought a few women’s low-rise panties to replace my men’s underwear.
In the 70’s, although fashions changed and left the androgynous patterns behind, I continued to favor those that I found feminine. Eventually, it became a practice that blended less successfully so my crossdressing was driven underground. I started shopping for shoes that I could wear privately with panty hose. I had some platform sandals that went unnoticed if I wore them with flared jeans. I found dresses made from stretchable material, which seemed to fit well enough and look feminine.
Near the end of the 70’s I began to travel overnight several days on most weeks. I built a small collection of feminine attire that I would put on at night as I watched television in my motel room. I never really looked credible except for my legs which appeared very feminine in nylons or panty hose.
In the early 80’s my doctor told me I had high cholesterol and should consider medication. I asked the doctor if better fitness and weight loss would reduce the cholesterol sufficiently. He was skeptical but did not argue. I began to run for exercise for the first time since high school cross-country, at which I never excelled.
Five years later I’m 20 pounds lighter and my cholesterol is within normal ranges. I was running five or six days a week. I found that running gear hugged my body much like the feminine wear I had enjoyed so much. I accumulated a collection or bike shorts and running tights that allowed me to feel good and still move around in public with few stares. I often got compliments from women on my legs in running tights. Since a lot of the running clothes were unisex, I could buy them without notice. Nevertheless, for some reason, I bought mine mostly in women’s sizes. I enjoyed knowing that I was dressed in women’s clothes.
Throughout the 80’s into the 90’s I continued to dress privately. I once suggested going to a Halloween party in drag, but my first wife was turned off by it. Toward the end of our marriage, she became aware that I crossdressed beyond the running clothes. I tried to tell her what it was about, she didn’t want to listen. Before the internet it was pretty difficult to support the concept that my propensities were neither perverted nor unusual. I think her contempt drove me further into privacy – we worked different schedules, so it was possible to conceal my dressing pretty effectively. As the kids grew older this became more difficult.
In the early 90’s I was offered a new position in the KC area. This move ultimately brought us to divorce. In the early months of the move, I dressed every night while alone in my apartment. I eventually bought another home, the distribution of property progressed, and two of my children chose to live with me. They headed off to college.
A friend of mine introduced me to a wonderful and beautiful woman who I started seeing. I was so taken by our relationship that I virtually stopped crossdressing beyond the running clothes – it was enough. A little over one year after our meeting we married. Regrettably, it never occurred to me to tell her about my crossdressing before we were married. I didn’t plan to conceal it – it just never came up and did not seem important to me. I knew that it would not interfere with our sex life because I could not be more drawn to her sexually.
Our early months were playful. We went to several formal and/or “dress up” events where I was required to wear a tuxedo. My wife commented before one event that she did not have matching shoes. I was more experienced than she knew at shopping for women’s clothes, so it took me no time to find her some beautiful dress pumps that coordinated very well with the dress she had chosen. She was thrilled and told our table mates at the event what I had done. Several of the women said they wished their husbands were so thoughtful and fashion conscious.
At another event, she showed me the dress she planned to wear and again I found some expensive blue leather pumps (4 inch) at a closeout price. Again, she was thrilled. After the event, she told me that she was uncomfortable with the shoes because she thought they drew more attention than she liked. You bet they drew attention. How could a trim attractive woman, with gorgeous hair and eyes, and shapely legs with slender ankles not draw attention when stylish heels enhance her legs?
One evening when as we were laughing and talking, she said I would not be so eager to buy her high heels if I had to wear them too. I said that I had worn high heels. She laughed and asked me where. I told her that I had dressed like a woman for a Halloween party – this was not truthful, but it had been my intention as I mentioned earlier. I left the room for a few minutes and returned after changing into a sweater dress, stuffed bra, panty hose and heels. I can still remember her comment at seeing me, “Well look at you!”
We played around on and off with my dressing for several months. My wife really seemed to enjoy it. We were, however, newlyweds and newly in love and almost anything we did together made us happy. I don’t know when it began to change but it did. I read once that a fellow traveler initially found his partner accepting and eager to play dress up. He felt that his excitement got the better of him and he overdid it. I believe that was one of the things I did. I mostly wore lingerie – panties, garters, and bra. I always bottomed them off with high heels, although mostly the same two pair of black (patent leather & suede) open-toed pumps. I had a couple of dresses that worked pretty well.
One day, my wife said she had grown less comfortable with my dressing and that she wished I would stop. I didn’t! I couldn’t! She knows I still dress, but she doesn’t want to share in it, and we seldom talk about it.
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