A Natural Fit

Sitting here in my gorgeous maid attire—petticoat, stockings, corset, heels, you name it—I can’t help but feel there’s no issue with what I’m doing. It really isn’t a problem, and I know that deep down. Even if I have to fall back on the excuse of “it makes me happy; everyone has their own thing,” that holds true. Society’s standards matter to me because I was raised respecting them, but that’s not my real struggle… I can handle playing the male role in public just fine. The place where I truly live as myself is right here at home…

I’ve been cross-dressing since I first started feeling desire, or at least ever since I can recall. Growing up in a house full of women, with only my mom’s boyfriend/fiancé (whatever they were) around the other guy was quite a jerk… that’s for another story. Not wanting to be like him and being slightly annoyed at Mom for keeping him close, I started noticing what my sister did. She was definitely the most feminine person in our house. Since we were so tight, I picked up on her habits but didn’t think much of it until about eight years later when she moved out and curiosity took over.

I began by borrowing my mom’s bras, sometimes a dress too, just to see how they looked on me. Naturally, I was hideous going through puberty… yeah:P But I’d do that, stay dressed up, and get bored after about 20-30 minutes. This pattern lasted for a while until it became less frequent because there wasn’t much else happening eventually I learned to masturbate, and the cycle of bras and dressing continued, but now boredom only hit after I “finished” (these days, I keep my clothes on even past that point simply because I can, being so comfortable [within these walls] in this attire). Then one day, a friend and I were browsing porn (a big surprise for someone ~14 years old?) and we discovered . I had never felt such arousal before! Seeing those beautiful women bound tightly, I knew right then it was the reason I spent half an hour in bras and dresses; why I’d steal my grandma’s robe belt to tie myself to the bunk beds. I wanted to be the “kidnapped” one, the helpless figure waiting for anyone to do as they wished with me. That discovery naturally led into selfbondage of course, though that isn’t our main topic here…

To wrap it up and conclude: Society raised me as a man, and I know without doubt I can fill that role—and enjoy doing so. I LOVE having a penis. Truly more than anything else in the world, believe me. But perhaps, just possibly, I envy women for several reasons I haven’t fully identified yet. For sure, I’m jealous of being the “weak” or “submissive” one—a role stereotypically assigned to women—whereas men aren’t expected to occupy that weak/sub space. And even simply because women can have (perhaps not necessarily more than guys, but certainly different) multiple orgasms rather than just a single big hit like we do. But there are other things too; I feel it. I just don’t know what they are yet… much like many people here who found this forum which has been such good fortune for me.

I wish for just one person outside of this site to understand me without judgment—someone with whom I could share all of this, perhaps elevating our relationship to a “back-up release” level or even further into full bondage partnership. Yes, there is someone who knows about my CDing and that I practice SB. But she isn’t quite the one I seek, despite our closeness over years. She knows almost everything except this core part; yet I don’t feel confident she’d see me differently after hearing how seriously I take crossdressing—to the point of spending money on it casually as if it were normal household routine.

Idk. Guess I just needed to voice these thoughts and free my mind from this stirring problem. One last thought: I wish I could be a woman for just one week, heck, even ONE DAY, just to experience that side personally. Of course, there are limits when using someone else’s…:twisted: but I only need one day to experiment fully. To tell the truth, I’d spend at least 12 of those 24 hours orgasming in bondage because I would have the power to punish/pleasure myself that way, which isn’t as easy for me as a male.

Big plus right now: I look gorgeous! I just need my reasonably priced blonde wig to complete this outfit…:gag::whip: