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Showing posts with label Feminization and cross-dressing. Show all posts
Showing posts with label Feminization and cross-dressing. Show all posts

Tuesday, August 21, 2007

I want to be a pretty boy

I've never been a manly man. When I was younger, I watched quite a bit of television. I remember lots of the imagery I was presented with quite vividly. In almost every case, I wanted to be the girls. Growing up, I quickly learned that wanting to be more like the girls was a desire frowned upon by pretty much everybody else—not least of all, by the girls.

These days, the same things still come up in daily conversation as they did in years past. "I wish I could lose ten more pounds—I don't feel pretty," I hear women say all the time. In response, everyone simultaneously begins talking about the oppressive nature of our culture's media campaigns. "Oh, come on. You don't have to look like every model in the magazines. You're smart, you're kind; of course you're hot," they'll say to her in an effort to comfort and sympathize.

Most of the time, I think women's self-image issues are physically, though not emotionally, unfounded. All but one of my girlfriends were, to use the obvious example, heavier than the BMI charts would have them feel comfortable about. My femdom fantasies have always been tilted toward larger girls. Hula dancers were an ironic motif, but I attribute this mostly to the healthier, more attractive weight Hawaiian girls tend to carry. I'll never understand the fetish for stick-figure girls. That can be sexy but I think women are sexier if they're shapely.

Issues men may have with their body image, however, are almost never even recognized. If they are, they discuss how unmanly boys feel and offer ways to feel more manly. Nothing we see in our culture tells boys that it's okay to want to feel pretty, to want to be treated in ways similar to the way we see people treating girls. If a boy, like me, wanted that, they call him a sissy and expect him to want to feel bad about it. I find this fact, an association often cited between cross-dressing and humiliation, nothing less than repulsive.

Furthermore, every time I've ever hinted at having body image issues of any kind at all, a very strange thing happens. Rather than address these issues, people turn to my girlfriend and give her a once-over. Then, they turn back to me. "How can you think of yourself as not attractive?" They ask, puzzled. "Your girlfriend is so hot."

Granted, my girlfriend is hot. But what, pray tell, does that have to do with my own self-image? You've just told me that my own self-image should be measured by how hot my girlfriend is. Call me crazy, but my girlfriend's attractiveness should not be the scale by which I measure my own.

Is that what you'd say to a fat girl, by the way? Oh, you're totally sexy because your boyfriend is super skinny. What kind of logic is that? It's not only completely missing the point, it doesn't make her feel better. In fact, it often makes her feel worse. And that's exactly what doing that does to me: it makes me feel worse.

Why is it a taboo to discuss men on the basis of their looks? Even in romance novels, where the gallant and obligatorily handsome man plays center stage, most descriptions about his looks center on his other attributes. His strong muscles. His virile penis. His healthy hair. It's not about the way he looks, it's about what he can offer in every other realm; wealth, health, or power. Even here, men's sexual attractiveness is being judged on everything except their looks. This is crazy.

To top it off, even the pretty men, who were called the derogatory term "twinks" in gay slang for quite a while, are usually portrayed in as decidedly not delicate a manner as possible; sweating profusely, working out, doing some manly chore, or otherwise being rough and tumble. The message? Be ruggedly handsome, sure, but don't be pretty.

By this culture's dogma, being pretty is a woman's job. Women are the ones who are "supposed to" do the attracting; men are supposed to be attracted. But this is insulting, and unfair. Wanting to feel pretty often goes hand-in-hand with wanting to be pursued. The emotions are the same: love me, I'm precious. But being pursued is the woman's job, as if they are the only ones allowed to feel as though they are precious and worthy of loving attentions.

This whole fucked-up mess does a lot of things for men. It makes us get paid more at work. It makes it easier for us to attract people into old age (where, I'm sorry, looks are just not going to follow). It makes it harder to objectify us in ways we don't want. And, unfortunately, it makes it a lot harder for us to talk about body image issues—especially if you're like me and you don't even want to have the traditional Vin-Diesel-the-body-builder look and instead want to look like the lithe, nubile, pretty young things you only see cast in the gender role of supreme femininity.

Well, I have a confession to make. I like dressing up as a girl because, in part, it makes me feel pretty. It does this because putting on frilly panties is the only time I feel the culture in which I live is telling me that I might actually get away with being pretty.

This confession, low and behold, is not uncommon. Men who want to feel pretty end up wanting to emulate women because we have no other choice. Why can men, secure in their masculinity, not also be pretty? Even the dictionary is stupendously unhelpful here. Defining "pretty" results in this definition from Princeton's web dictionary:

pleasing by delicacy or grace; not imposing; "pretty girl"; "pretty song"; "pretty room"


(Emphasis added by yours truly.)

I have been called graceful. I have also been called delicate. I've been called pleasing a bunch more times than these other two things combined.

People I don't know ask me if I dye my hair when they look at its color in the sun (I don't). They ask me if I've ever played the piano when they notice the way my fingers curl around cups as I drink (I haven't). They have remarked on how carefully I treat all my belongings, and how thoughtful I am when I am hosting a guest. But they have never called me pretty.

It may surprise some of you to hear this, but Eileen is actually the first person I have known that has called me pretty. She is fond of my ass and these days I might call it one of the prettiest parts of me, but it was not always this way.

One night many years ago, well before I even consciously thought about why I kept wanting to feel pretty, I was lounging with my then-girlfriend in the bedroom I shared with my brother. I remember only a single sentence from the conversation we had that night. It was this sentence that my girlfriend said to me that cued six years of body image issues centered around my butt: "I would like it if your ass was firmer."

What did firmer mean, anyway? It meant that I should have more of a boy's body. I didn't have a muscular gluteus maximus; I didn't have the body of a strong, rugged, self-respecting man. But you know what, I didn't want that body, either. And that should've been okay.


Addendum: For those interested in a bit more academic self-education (the best kind, if you ask me), I would highly suggest reading the Wikipedia articles on sissyphobia and effeminacy, for a start.

A particular passage of interest is cited below, and serves as a wonderful example of the fact that cultural ideals change with time. My message in this post, if you are to take one from it that I did not actually intend when I started, would be to stay aware of this constantly changing cultural stereotype—in all cultures and in all situations—and to avoid letting cultural noncompliance result in prejudiced or oppressive actions of any kind.

Pre-Stonewall "closet" culture accepted homosexuality as effeminate behaviour, and thus emphasized camp, drag, and swish including an interest in fashion (Henry, 1955; West, 1977) and decorating (Fischer 1972; White 1980; Henry 1955, 304). Masculine gay men did exist but were marginalised (Warren 1972, 1974; Helmer 1963) and formed their own communities, such as leather and Western (Goldstein, 1975), and/or donned working class outfits (Fischer, 1972) such as sailor uniforms (Cory and LeRoy, 1963). (Levine, 1998, p.21-23, 56)

Post-Stonewall, "clone culture" became dominant and effeminacy is now marginalised. One indicator of this is a definite preference shown in personal ads for masculine-behaving men (Bailey et al 1997).


My personal experiences written above are likely the result of my interaction with New York City's leather subculture, as that community is my primary social outlet (for now).

Thursday, March 29, 2007

On the wonderfulness of thongs and chastity devices

Okay, so here's a funny subject I've been trying to experiment with a little lately. This past week I've been locked up in the CB-3000 at my girlfriend's command. The last time I had been locked up wasn't for a good many months ago. (I have it recorded on my personal kink calendar, but without looking it up I'd say it's been at least four months since my last lock-up.) I'm glad that, after all this time, it's still relatively easy to get acclimated to wearing the device again. Sleeping is not a problem, comfort is hardly an issue, and overall it's not difficult to remain hygienic.

The thing that has changed between then and now, funnily enough, is the kinds of clothing I typically wear. My wardrobe is stocked full of form-fitting shirts and, more to the point, pants and underwear. My underwear inventory isn't even very good at accomodating my penis when I'm not locked in the chastity device (it's mostly very feminine wearables), so trying to maneuver into it with the bulk of the chastity device is an amusing challenge.

This has led me to experiment a lot more with what kinds of clothing work best when locked. I've had to consider both comfort and look, for obvious reasons. The results have surprised me!

For instance, it turns out that thongs (designed for women) are actually very comfortable to wear when I'm locked in the chastity device. It seems that the tightness of the thong stretching over the device gives me a lot of support in the needed area, and pulls the device downwards enough to avoid being a noticeable bulge in my pants. Since there's not a lot of fabric, it's also a lot easier for my bits to "breathe" if it's warm out. Wearing tidy whities or similar underwear is supportive enough, but also stifling. Besides, my ass looks like a million bucks in a thong. ;)

I've also found that low-rise women's jeans are way more comfortable than traditional men's style jeans. This is because it's trivial to place my package on either side of the seam without trouble, whereas in other styles of pants the seam itself gets in the way of things. Readjustments have been necessary on occasion, but it's not difficult to find a public restroom to do so.

Of course, I'm not sure how much of this is personal taste or actually making sense objectively, but whatever. My conclusions from all of this experimentation largely boil down to two salient points. These are:


  1. I need to purchase way more thongs.

  2. I can be a bit more bold in the style of my dress while locked up. (Yay!)

Wednesday, March 07, 2007

Feminization as the perfect creation


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.