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Shy closet sissy
I've been a crossdresser since I was about 10 wearing my mom's pantyhose. I've gone through life without anyone ever finding out. I wish I had the nerve to confess to a woman in person, hoping she'll help me live out my fantasy. My fantasy is to give a ** while she is watching giving me tips. Then out of nowhere she has another man take my virgin **.
Jun 6
To start, you do not need a woman watching you. Take as many men as possible and let it be known you want to be watched. It will happen.
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Join a Dating site. specializing for gay and transexual men. There are lots of them. Make it clear who and what you want. It will happen. Good Luck
I tell girls on first date that I have a thing for wearing feminine underwear. So far, none have rejected me.
Yes, I am pretty much the same although for me it was first my Mom's ** and then bras. I have never told any girls about that other than my now wife who just diminished it to experimenting. I didnt push it so even she doesn't know the extent of my fantasies and desires. If she would have said like, "Oh, that's hot", it would be a whole different thing I think. I have also had bi "encounters" in my life including giving up my **. I have confessed that to a few girls/girlfriends. Even then, I didn't get the interest I think I needed to reveal my entire self. I suppose I was just hoping one would offer me to take it further, like, "Oh, I want to help you do it right. Let's find you a date. We'll go bra and panty shopping and dress you up like a such a cute little sissy. I want to teach you and watch you." These days though, I still don't share these fantasies and desires with my wife or any girls in person, although I talk a lot about it with girls online constantly. I still love confessing my sissy self to girls.
You are on the right track. Use your GF to help feminize you. Find and date men on your own. Men love a feminine crossdressing man. You may even want to start using hormone therapy to reduce facial and body hair, it also helps gain a feminine shape body.
Not all guys want to have relations with men or be trans. They love playing dress up.