Tough Times for the Transvestite

This lifestyle is still incredibly new to me. Every morning, I wake up, look in the mirror, and marvel that this is not, in fact, the remnants of a dream. I dove into dressing knowing nothing—besides the fact that wearing women’s clothing was extremely erotic. There’s so much more, now. Everything is so new—I’m realizing how much I don’t know—it’s an exciting, vulnerable, scary time.

Just the other night I had a sort of breakthrough. Up until that moment, Dulcinea’s and my joint crossdressing/genderbending forays have been spotty. I’d be thinking about it all day, preparing myself, sending hints to Dulcinea, waiting for her to come home and play. She’d come home, either miss or ignore all of my hints, and go to bed.

To me, it felt like she was no longer interested in exploring my femininity with me. Frustrated, disappointed, hurt, misunderstood, I confronted Dulcinea. We stayed up and talked about it, and we came to a number of interesting realizations.

Nature was a bit of a factor. I may have been a bit too subtle in my hints, and I can see where that problem lies. I still find it difficult to seamlessly step into a crossed role. Especially when I’m not alone. The transition from male to femme is extremely delicate. Any hint of ludicrosity can make that step into character so high as to be insurmountable.

So, to segue as smoothly into femme as possible, I try to avoid changing in front of anybody—or if that’s not possible, have it be a part of our scenario. And in either case, I do not under any circumstances directly say, “I want to be a woman tonight, Love.” I’m subtle in conveying my intentions. I’ll leave a pair of panties on the bed, or if I’m feeling submissive, a collar.

The problem here is twofold. Oftentimes, Dulcinea won’t pick up on the hint. She has other things on her mind, and though I may have been thinking about it all day, she hasn’t, and probably didn’t even know it was on my mind. Since I rely on her seeing what I’ve laid out when she changes out of her work clothes, it’s pretty easy to miss the hint until going to sleep.

It doesn’t help that my dressing has become linked to dominant/submissive play in Dulcinea’s mind. When she sees the panties out on the bed, Dulcinea told me, she thought it meant I wanted analplay and to be dominated. Neither of us can assume a dominant bondage role on a moment’s notice, and when she stumbles upon my panties laid out as a sort of hint, three blinks from sleep, she’s not in the mood. We’ve since agreed to communicate better, regarding this. For me, that means more direct hints, and with enough time to mentally prepare. But there’s still a problem.

In Dulcinea’s mind, the panties were just a sexual thing, a sort of selfish excuse for me to enjoy anal pleasure. I think she was a bit hurt that I was so interested in crossdressing and panties; in her mind, it indicated that she wasn’t adequate for me without them. Not true, painfully not true, and I told her that. She asked me what the panties meant to me.

And stumped me.

crossdressing