Hello, this is my very first post; I just joined the other day. I truly don’t know where I’m going with my crossdressing.
I recently turned 65 and am retired, happily too. I must add, healthy and fit as few people take me for my age. I have many interests that keep me busy, music, old cars, photography, and others.
After reading a number of other stories here, it’s clear that mine is similar. I first started crossdressing around age 12 by trying on my mother’s underwear. At that age, we are entering puberty and things female are suddenly much more interesting, including clothes. The old expression about clothes “making the man,” I think we might agree that clothes make the woman, too!
My favourite was what I know now is a corset. My mother was a bit heavy so she’d wear shapewear to help out. The feeling was fabulous when I slipped into it and one of her slips.
I was deemed old enough to be left home alone while they went out shopping. Being an only child, I had time to myself to, be myself, I guess. I simply cannot remember what led me to try on my Mom’s things, but I loved the feeling of her clothes, even though the fit wasn’t great. This also quickly became highly sexual for me, too. I started more fully dressing, using socks to fill out where her breasts would have filled the bra pockets, and then putting on a shirt. I never tried on any of her outer clothes.
We moved in with my grandmother after the sudden death of my grandfather when I was around 15. I had little private time, but I didn’t seem to mind. I don’t think I had the urge or felt the need to dress for many years; I had discovered girls! Even when I lived on my own for a few years before I was married, I never once considered dressing.
I met a wonderful, beautiful woman who quickly became my best friend and lover. Over the last 35 years together, we’ve had two kids, both pretty well grown up, though the youngest is still attending college and living part-time in another town. We have more time to ourselves now and love it.
As a couple, we’ve had a very active and private life, in that respect. As the children aged, adult “play-time” got tougher. We did a male/female swap at Halloween after everything was done and our kids were safely tucked away. The old thrill of dressing in women’s clothes returned. We added dressing to our private time; I’d dress up occasionally, but it wasn’t something I felt a need to do regularly. I sure enjoyed dressing when I had the chance!
That went on for 10-15 years. Over the last couple of years, I started wanting to do it more. Since the middle of last year, I find myself ever more drawn to the femme side. For Christmas, I usually buy my wife some kind of sexy clothes, but since she is a plus-size now, it’s hard to find nice things at the lingerie stores. I started looking online and ended up buying myself a couple of nice bras, garter, and stockings. At the same time, I ordered similar items for her!
One of the sites I browsed through had a section for crossdressing supplies. I was fascinated by all of the “extras” one could purchase. Those very realistic breast forms looked amazing; much better than using socks, like I did when I was 13. I haven’t bought any forms, not yet anyway.
I realize that she knows I’m enjoying dressing up more, and she’s been understanding about it; I don’t want to push things too far. I don’t feel the need to fully transition, but I am very mixed up in my feelings about all of this.
I don’t want to mess up things with her, and I certainly don’t want the rest of my family to know; some might be more accepting than others. I’m not nearly ready to go out dressed, and I don’t think that I’ll ever get to that point, but I didn’t think the femme side would feel so strong in me either. I do have this interest in dressing well enough to go out in a limited public setting. My other issue, as it were, is the beard I’ve worn for 40 years, and is very much ensconced in my male persona. That would have to go if I were to go out in public.
It was early this year that my femme name just kind of popped into my head. I began thinking that my femme side should have a name, and a day later, Amy appeared; it’s nothing like my male name.
I’m conflicted in my feelings; my male side is very strong though I’ve never been a macho guy. In some past situations, I suffered because I wasn’t. I’m only attracted to women; I absolutely love the look of women, finding so many of them attractive, regardless of their ages.
Last week, I took another step and went to a shop in the city (I live in the country), which sells items for CDs. I bought a nice wig and another skirt for myself. The person was nice and very understanding; it was nice to actually shop for Amy and not pretend it was for someone else.
As I mentioned, I’m feeling conflicted. I need to let her know how much I love the feeling of being dressed. I’m worried, as we are finally retired and hope to do some travelling and other activities that we’ve wanted to for many years that I might upset our plans and hurt our relationship. I don’t want that to happen.
Anyway, that’s where I am now. I’ve wanted to share this with others for quite a while.
More Articles by Amy Myers
- Try to be your Real Self
- Dinner and Pride in Toronto, June 2023
- Xpressions Christmas Gala
- Amy’s Day of Wonder
- Shopping in Person