Over the past few years I've spent some time on sissy sites, reading and posting on the forums.
One thing that has become clear to me over that time frame is that I'm really not like most of the sissies you'll find there. While I have my fetishes, they aren't really for a particular feminine item and I really do love women's fashion, but at the same time it's not about me wearing fashionable women's clothing. I like certain materials, but as a whole my main attraction to women's clothing is how it looks on a woman. I am not pretty, nor would those items look good on me. Most of my experiences with dressing were as caricatures of a woman and not resembling an actual woman. I guess maybe it's that I feel so inferior to a strong woman... that I don't deserve to aspire for womanhood, but I can aspire to serve her and her superiority.
I'm not gay or bi, nor do I have any desire to engage in any homosexual acts. If I was to ever have (or be forced to have) a trans-gender procedure I would end up a lesbian and still be submissive to women.
Sometimes it's hard for me to relate to other sissies since I rarely share the bulk of their desires. I have been able to help many of them with advice and guidance on attracting or making themselves attractive to a Domme and in some cases, helping them guide their current significant other into the Dominant role.
I know there's a bit of a stigma against sissies in the BDSM world and many times it's deserved (although it just as frequently is not). It seems there's a lot of them out there that want all sorts of attention showered upon them and they just sit back and enjoy the ride through their fantasy activities. It probably doesn't help that many of them have little if any experiences with Dommes and have often been jerking off to the same fantasies for several years... this kind of behavior shifts their focus too inwards when it should be outwards.
Not many of them understand that to be an attractive sub you have to be able to offer a Domme many things that she finds pleasurable or useful. If you are lucky, she will find the some of the same activities pleasurable as you do, but this often isn't the case. I can say for things to work in the long-run, you should both have at least a few enjoyable activities in common.
The advice I would give to any sissies who might be reading this (if any of you are out there) is:
-Have as many useful skills as possible. Be able to cook, clean, and do yard work like a pro. Be good at massage, master cunnilingus, and work on as many skills as you can. Carpentry? Great. Fixing computers? Good. Plumbing, electrician's work, auto repair? Solid. Sewing/tailoring? Great. The more you have to offer, the more attractive you will be.
-Be interesting. Be funny. Be able to hold a conversation. Be able to be a great friend. Be able to be a great lover. Be able to give comfort, support, and everything you think people need to be happy. 24-7 is not Femdom ALL the time, it's Femdom at ANY time. Be a real person. The better and more interesting person you are, the more attractive lover you will be.
-Be flexible. Be willing to endure things you don't like. Be willing to try things even if you think you won't like them. Be willing to take a beating. Be willing to go long periods without an orgasm. Be willing to get pegged. Be willing to be tied up in the closet and ignored. The more you are willing to try and do, the more likely she will be to give you a chance.
-Be honest. If there's certain things you NEED, let her know. If there's certain things you really like, let her know. When fetishes and fantasies overlap between two people are when BDSM relationships work. If you really want her to dress you up and humiliate you, hopefully she'll want that too. If you are attractive to her because of the qualities I listed above, she might choose you and do it even if that doesn't "do it" for her.