
One of the things I have struggled with as a cross-dresser over the years is body weight. I have been up and down for a variety of reasons, but this time I think I am finally headed the right way.
Way back when I first started dressing in my mother’s skirts and blouses, there was a point where my growing male body fit perfectly into her things. The waist sizes, the shoulders, and even the shoe sizes all worked out right. Those were some great times, as I had literally had access to a full female wardrobe. Unfortunately genetics decided to put an end to this as I began to outgrow almost all dimensions of my mother’s things. Sadly, I came to the realization that I needed my own female things, or I would end up ruining my mothers.
One thing I have always been very good at is gaining weight. Actually, it might just be my greatest talent. I love to eat all kinds of foods and that pleasure is only matched by my love of all kinds of beers/ales. With this in mind, I was able to effortlessly put on weight.
Don’t get me wrong, I didn’t really want to gain weight… it just happened. The older I get, there more effortless it became. Now to be totally honest, at one point I liked the weight gain, because my whole physique became soft and round. Even though I was plus sized, there was nothing powerful or muscular about my build. My adams apple was completely obscured (not really very big anyway) and I was able to create some impressive cleavage using a boob belt. All these things helped me to feel exceedingly feminine, but only to a point.
Being brutally honest, I didn’t like being fat. I enjoyed the cleavage, but there was really little else good about being big. I topped out at about 260 lbs (118 kgs or 18 stone, 8 lbs).
I didn’t feel great, couldn’t keep up with the kids in anything, and probably wasn’t too healthy. Any of these realities should have been enough of a reason to make a change in my lifestyle, but they didn’t… at least not by themselves.
I could (and did) get women’s clothes in larger sizes, but they weren’t the feminine articles I really wanted. Once I had come to the conclusion that the fashions of the 1950’s were where my heart was, I started focusing on those vintage skirts and dresses. The problem is that women in the 1950’s were smaller on the average. Most of the items I found and fell in love with were simply too small for my larger frame. It was the desire to get my hands on more of the real vintage fashions that pushed me to lose some weight (sad but true).
So I have been at it now for about eight months, and to date I am down about 55 lbs (25 kgs or 3 stone, 13 lbs). I do feel much better and I am losing dress sizes! I am seeing a much greater selection of vintage items available in my range, but I know there will be even more as I continue to lose more weight. I actually get excited when I weight in and see I have lost some more weight and know that means the selection of vintage clothing is increasing conversely.


One thing that has not escaped my attention is that most of women wearing the fashion I prefer (full skirts and petticoats) have that iconic “wasp waist” look that at this point I could only dream of having. Tight tops, tiny waists, and full, poufy skirts are so enticing to me. That 50’s hourglass silhouette… it is the look I really want, but once again genetics will be working against me. Guys, even ones in great shape, just don’t achieve Barbie doll thin waists.

Betty Brosmer… the original living Barbia Doll.
Truth is most women didn’t achieve those wasp waists without some assistance, namely the corset. So now I am infatuated with the idea of getting a corset and beginning to train my waist down several inches smaller than what I could achieve through normal means. I have just started reading and researching the subject of “waist training” and I have a lot to learn, but I am truly enamored with the idea of wearing a tight laced corset.
This would be the type worn just at the waist, not right up to the breast or under-breast. So far I know that to be truly effective in training, they need to be worn at least 12-14 hours a day (i.e.) almost every waking moment. The idea of wearing one to work is not so ideal, especially when feigning a masculine existence! So I am thinking of wearing one at all times, outside of work and mostly at night. I haven’t quite figured this all out yet, but I gather for some reason wearing a corset at night while sleeping is much less effective. Figures!
Another thing I have considered and not yet figured out how to handle is my wife. I’m pretty sure she will not be in favor of the corset plan. Once I have a bit more understanding, I will have to explore the idea with her. Just based on experience, I am sure she will think I have fallen a little farther down into the rabbit hole and oppose the idea. But we shall see. Of course I still would have to hide it from everyone else in my personal life, and that would still be a challenge. The good news is it should be easier under all the winter clothing that will soon be coming out of the closet, even if I am not.
After writing this, I took a minute to think about the corset idea and all that Valerie has become. Once again I have taken the cross-dressing to a new level (or would like to). Again, I have to wonder… just where will it end?
-ValS