in answer to your question, TRANSVESTISM IS A FETISH! some people consider it a part of the transgender spectrum, but it's not like he wants to be a woman (transexual), as can be shown by the picture of him holding his penis rather than concealing it, he has a "Living" feminine (not female per se, but feminine) side which he finds attractive, and it comes out when he crossdresses. I can also see that it is sexual because he is wearing lingerie rather than casual, appropriate women's clothing.
another thing, only a very small number of transvestites cross dress in public, the majority of them do it in secret, behind closed doors, and some of them (like me) are happy doing so. Some may feel like they need more freedom, that they need ways to express their femininity in ways that the confines of their rooms can not offer, these transvestites are very rare. (NOT to be confused for trangenders-or "other" transgenders if you include transvestites into that spectrum-who crossdress as a means to fulfill their gender identities.)
I've been there before-posting pictures on the computer-and I did it because I felt like I won't have a chance to ever cross dress again. It's a matter of finding a balance of when and where it's acceptable, and these parameters are flexible for those who only feel the need to cross dress sometimes.
listen, it's not necessarily an obsession to the extent that sweetiegirl is describing; everybody's different, and their interest in transvestism vary widely.
I like to think of it in this way- the part of my brain that tells me "HAVE SEX WITH THAT GIRL!" is also saying "WEAR THAT MINI SKIRT!" It's like I'm seeing myself as a hot girl I'm about to sleep with. sounds strange, sounds like I want to be with someone else, but that's not true, because it's like that hot girl is always with me- it IS my feminine side, because every girl I was with has become a part of me-much like any other guy-except that part of me (my feminine side) is more "real" than other guys, it holds more "Life" I like to think that I have a healthier balance of "yin" and "yang". In short, femininity is so beautiful and sexy to me, I sometimes just want to be a part of it.
Another thing that's common with transvestites is that after ejaculation, they suddenly become disgusted with themselves (I've been there!) and they throw away their "clothing stash". This feeling of disgust is a product of society's view of men in women's clothing. "what am I, some sort of freak!? what's the attraction to this clothing? why am I so different!?" and so, like many things, this situation can be viewed as either a mountain or a mole hill. It's important that, if you want to let your boyfriend know that you know about his secret, you try to make it a mole hill first in your own mind, because if he has those pictures on his computer, chances are that he is trying to supress his crossdressing, and instead he is looking at the pictures as a substitute, and that means he sees it as a mountain.
Also, just because he has a large feminine side, doesn't mean that he is effeminate, a lot of transvestites are very macho when they are not cross dressed. cross dressing-for transvestites-is usually just a means to express one's feminine side, either sexually or emotionally.
I've always felt that feminine side: Even when I was three years old I've always felt like my friends were missing something inside of them. I then thought that were just being insincere. Then, at six years old, I realized I just had more- I had more sensitivity, more of a sense of romance, I was moved by things boys my age weren't moved by, and I had more of what girls had. That last realization scared me, because I'm not a girl! I didn't want people to think that either, this insecurity caused me to push it back, I was "Manly" and "Masculine" and I ran away from it. This is the fear that chased me on and off throughout my life until I came to terms with it (I admit: with the help of my ex-girlfriend), and I realized how small the "problem" was. It's almost laughable from this viewpoint, the need to crossdress, now that I'm ABLE to crossdress, is getting less and less frequent.
PLEASE PLEASE PLEASE talk to your boyfriend about it, remember that he is probably very embarrassed about it, and if he denies it, please understand. If you love him, tell him you love him; I can imagine it's very important to him. Also know that posting his picture on the internet is a sign that the only place he feels he can find acceptance is in himself, and that even in there, the acceptance isn't complete. Also, YOU are just as important, if you deny yourself your needs, like my ex i mentioned before did, things can get ugly-compromises are key. Ask yourself this question-are you willing to buy him women's clothing? I say this because it is likely that he is VERY nervous about going into a store, or using a credit card with his name, to buy women's clothing.
I write this to give a man a chance I haven't had until recently. I hope your relationship turns out all right, and with this advice, you shouldn't have too many problems in that area.
remember that there are a lot of haters, and misunderstanders in the field of psychology. If you see the words "autogynephile", "paraphilia", or "pathological", YOU ARE NOT GETTING GOOD INFO! The best way to go about it is to just ask your BF about what he is feeling.
recap: Talk to your boyfriend, make him feel comfortable about talking with you about it (this takes PATIENCE), get to know what he'd like, tell him what you'd like, compromise :)