This is the next installment of my series on Sexual and Relationship Development. I wanted to discuss crossdressing, since I have done it. I have never made it a routine, but there have been a few times that I tried it. Because it came up in discussion on the last part of this series, I decided I would blog about it today. But I have some limited experiences where I wore women’s clothing. Of course, I mentioned in the introduction to this series, that I might jump around in my timeline a little and this is one of those times, since I have tried wearing women’s clothing at different times in my life. But here are the experiences
Part 3: Crossdressing :
Ages 8-12, approx.
In previous entries, I mentioned my cousin, Marie. Well, I spent a lot of my childhood with her and she had a bit more dominant personality than I had. Although, our experiences in playing dress-up were silly for the most part, there was a tendency on my part to try women’s clothing on more than I understood at the time. She and I would find clothes of older family members and try them on and play around in them. But there were other times when we would wear each other’s clothes and my cousin took a particular interest in seeing me like a girl. She would ask me to put on her dresses and skirts and then ask me to talk like a girl. Of course, when you are younger, this is much easier than when you were younger. Obviously, as we aged and I was not developing breasts at all, we would find ways to improvise – namely the egg shaped containers of L’eggs nylons made perfect breasts for a pre-pubescent boy to pretend to be a pre-pubescent girl. Of course my cousin “helped” a lot with this. For example, the first assist was realizing that using the parts from one container resulted in an asymmetrical look to my faux-breasts. So, we began using two different L’eggs containers to be more symmetric. She would offer me her braziers, so I could put those egg shaped things upon my chest and support them with a bra. I would wear her shirts and her skirts or dresses. But I didn’t stop there, because she would ask me if I wanted to wear her panties and I did at the time.
She would tell me how cute I looked and ask me to twirl in her dresses. And since we were kids and feeling silly, she would war my clothes and we would walk around her house (Often times, my aunt would watch us while my mom worked or vice versa, but I only dressed when I was at my cousin’s house) pretending to be each other. It wasn’t always a quick in and out of the clothes, because sometimes I would spend the entire day in her clothes. Sometimes, in a teasing way, even my aunt would tease me and call me her niece. It felt oddly comfortable at the time. We did this on different occasions and under different circumstances. Sometimes, there was a sexual response to it all, but never in a way that I felt a sexual attachment to the clothing (If I did, this would probably be recognized as a fetish, but it never seemed to rise to the level that a fetish would). I always chalked it up to the idea that I was responding to the thrill of doing something naughty or something that was assumed to be wrong. Boys don’t wear girls’ clothes, do they?
Predominantly, through my teen years, I did not wear women’s clothing. I think it had a lot to do with the fact that I was trying to separate myself from social stigmas, societal expectations and trying to decipher if my sexuality was normal or a result of being a victim to a sexual assault. But eventually I met a young woman named Katy (I’ll talk about her in its own blog entry, because she was a significant relationship in my life). Honestly, I’m not even sure how Katy and I even began dressing me up, but it was certainly her idea. I think it was something as simple as she and I in bed together naked and she asking, “Will you put on my clothes?” Regardless, she began asking me to do it and she would go all out when we did. If I recall, however, we did not do it often – maybe 3 or 4 times (My age gap is due to the fact that I can’t remember when the exact time frame would have been).
It began with her asking me to put on her lingerie. Then eventually she would have me wear her dresses or her skirts. I would walk around in her heels and she would have me put on different shirts and tops. To simulate breasts, we simply stuffed her bras with toilet paper. One time she even did me up in make-up and asked me if I ever wanted to wear a wig. We would make an entire session of dressing me up and putting make up on. I think, at the time, that although I was already settling into my masculine body, my face was still young and could be “dolled-up”, so to speak. She seemed to really enjoy doing this and it inevitably led to love making, so I didn’t refuse it. But at the same time, I found myself enjoying it and since I was still trying to figure out my sexuality, I had the inclination to ponder if I would be attractive to men dressed like this.
Although, I never wore women’s clothing in any public way, I did enjoy putting panties on from time to time. Occasionally, I did this without even Katy knowing about it. For some reason, I liked the way panties felt and I enjoyed the idea that I could feel pretty. Granted, it was not a common thing for me to do, but on the few occasions I did, I liked it.
Unsure ages, but older
I never really did much crossdressing after Katy. There were a couple of times during my marriage when I tried on a couple of my wife’s clothes, but by this time my body was so masculine, I couldn’t really find anything in her closet that would fit me without me ruining what I liked. But I would occasionally by myself some underwear and put them on, but I always kept it on the downlow and didn’t tell anyone. I sort of like the idea of feeling pretty and I felt like it was the way I could do that. Again, I never felt a sexual attachment to it, nor a need to do it, but occasionally it just felt nice and comforting. Almost like my feminine characteristics could find some validity in me wearing some lacey red underwear.