When I used to be closer friends with the Pro Dommes at one of the local dungeons where I live, I would get invited pretty regularly to their Friday night parties. These were not great events because the Mistresses never had a truly fun time (since they were technically working), and I’m pretty sure that’s why they kept inviting me; I was never a client, only a really, really young boy to play with. And I’ll admit it: I was incredibly naive.

On several occasions, the girls used to dress me in full cross-dressing gear from head to toe. One of them was a fantastic makeup artist, and so the first time they did this I was actually speechless when I looked at myself in the mirror on the wall. With the makeup, she had done such an amazing job that I actually got asked if I worked at the dungeon by one of the party guests, and another one who had been eyeing me all night had to “check to make sure” whether or not I was female.

At that time, I didn’t really understand the appeal of becoming outwardly more feminine. Now, however, it’s one of the fantasies that runs deep within me, for many reasons and, and elicits a lot of different emotions. (As a sidenote, there’s an interesting discussion spawning around this subject at the Fetish Lore Forum.)

Making Faces
By the way, when I asked her how she learned to do this she recommended a book that I think was called Making Faces. It was a photography book showing pictures of men’s faces made up to look like stunning women through the use of makeup. She said such books (and a willing human canvas) were the best ways to learn.

It had not been first time I had ever cross-dressed, but it was the first time I was truly made to feel like a girl. This was a subtle yet eye-opening revelation for me. I always had thoughts of what it might be like to be a girl instead of the boy I am, and from a very young age I became fascinated with the gender differences (and similarities) between the sexes. When I became sexually aware, I began to have (and still have to this day) a very serious case of clitoris envy.

I believe that this, in at least some significant part, is due to the fact that I have always felt very strongly feminine in many ways. The popular phrase these days is to say that I am “in touch with my feminine side.” I was an introvert and a shy child in general, but more so than this, I was hyper-sensitive to emotions and felt very moody much of the time because of this. I got along better with girls than I did with guys and I felt envious of them for being able to manipulate society’s double-standards in ways that I wished I could, such as the approval of playing a sexually submissive role yet at the same time desiring to be lusted after.

Cross-dressing in and of itself is a lot of fun. I find girl’s clothing to be unusually comfortable and very sensual. The softness of the fabrics such as leggings and nighties are extremely appealing (I’ve always loved soft things). The tight, form-fitting nature of the clothes such as jeans and shirts make me aware of my body in ways other clothes don’t. (Interestingly, that only became an appealing aspect once I begun to feel more okay about my self-image.) However despite all this, I never truly thought of myself as “girly” in the sense of liking pretty things for the sake of their prettiness or being enthralled with pieces of jewelry. I like pretty things and I love jewelry that is somewhat demure, but these things never defined the pleasant emotions behind wanting to be a girl.

I eventually confessed to my girlfriend how sexy I thought girl’s clothing was–everything from panties to outerwear. At first, it was a novelty when we went shopping for some tight jeans for me in the girl’s section. Then, it became a regular occurence. Now, I own more girl’s jeans than boy’s jeans, enough panties to last me through a full laundry cycle, and a little less than half my outerwear wardrobe is girl’s clothing. I don’t wear most of them for any special occasion whatsoever; they’re just part of my regular wardrobe. It certainly helped me to hear the continual encouragement from my girlfriend. She told me how nicely shaped my waist is and how feminine my ass looks, how sweet and cute I looked when I dressed in younger-looking clothes and how sexy she thought I was in my new tight clothes. Being handy, she made me lots of necklaces and we eventually bought a jewelry box for me.

All the while, we slowly began introducing more and more feminization aspects to our play and sex as well. It varied immensely and was the most role-play-like thing I had done to that point; at times she would speak to me as though I was a young lost girl, at others I would put on my sexiest red nightie and do my best to seduce her. While there was a naturalness to the play that I was not expecting, there was also the feeling of being almost doll-like in the sense that I was not myself anymore. Again, while I am very much a “girly boy,” I am still a boy.

Feminization, then, is partly self-expression but also partly being made into my dominant’s image. The submissive in me finds it incredibly erotic to be molded in whatever way my Mistress wants. When I am her little girl, even though I am a boy, that is an act of her power and my submission because I am then something she has made me into for her own pleasure. She turns me into her pretty, perfect little girl. And I like feeling perfect.