How "passable"/feminine must I be? Just to have fun.

[getinsideme]

Hello everyone. This is my first post, so I'd like to first say that I'm very impressed by the candor on this forum. I really appreciate this forum because it's given me some much-needed perspective, and gone a long way toward eliminating the awkward (shame?) feelings I have about some of my desires. So, thank you.

Here's my question - but first, some background. I'm not sure if I'm a transvestite or transsexual (I've wanted to be a girl from a very young age) but I've recently decided to explore. I have only a little experience dressing and I've never been with a man before (women, yes). I've gotten in touch with an older guy who really gets me and seems to be willing to take things slow. I intend to eventually get the best of both worlds: a man who understands me and connects with me on a deep level, but who will also fuck me ... hard.

My main concern is this: given some of my undeniably masculine features (I have a somewhat long torso, muscular legs, very masculine shoulders and neck, and my hair is thinning even though I'm pretty young) - how feminine must I be to attract somebody, for either a casual relationship or hooking up?

Specifically, how masculine is too masculine to complete the "illusion" enough to really get men interested in undressing me, and getting inside me? What kinds of general steps can I take to pass - even if it's only behind closed doors (even if I am a full-blown TS, I will never have the guts to transition)? How do you get the courage to buy skirts at a popular clothing store?

The bottom line is that I want (1) to pop my cherry (2) to attract men as best as I can with what g*d gave me and (3) to find people that will think I'm feminine enough on the outside to give me a chance to show them what's inside too.

Thank you in advance for your help, and in case I've said something offensive (terminology is a bit tough here, and I'm not sure how to be PC) I apologize and hope that you will see that I just need some guidance from more experienced girls (and admirers/men).