Tag: crossdressing

“I found out my boyfriend is a gay crossdresser”

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My boyfriend and I have been going through a bit of a rough patch. We have been happily together for almost a year. We recently broke up, but got back together. Me being the nosy person I am, I went through his phone while he was sleeping. Nothing could prepare me for what I found.

My boyfriend is a masculine, car dude, and has never given me any reason to believe he plays for the other team…..I found TONS of responses to Craigslist personals (MAN SEEKING MAN) asking for gay, cross dressing, and even transsexual favors. He has sent nude photos, and photos of MY underwear saying they were his! He had the Grindr app, kik, and another email to keep his secret life from his open one. I don’t know how to go about this, or even if I should. I am at a complete loss right now. Someone please help me!

I’m a guy and I love wearing dresses and jewellery”

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Hi, I am a straight 15 year old guy who occasionally, in private, wears dresses and some jewellery as I find them comforting. I am not gay, or trans, I don’t do it to be or look like a woman. I do it to feel better about myself (plus I look good in them!)

For example, the other day when I was home alone, I wore a black dress that I took from my girlfriend once. That’s the thing, I love my girlfriend so much but I feel shitty lying to her about this. I want to tell her that I like dressing in this way, so I can do it around her without feeling like a freak . Should I tell her?

Also, I have been thinking about sex as well, and whether we should try it. Although it will be my first time, I am ready (despite that we are underage). I want to approach her about it to see if she is prepared to take our relationship to the next level as I am so in love with this girl!
Is it a good idea?

“How do I come out about being a crossdresser?”

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I am a 65-year-old crossdresser. I do not identify as a woman most of the time, and yet there is a feminine side to me that I do not get to express as fully as I believe that I should. I have crossdressed for many years, but only in the last few have I tried to get more serious with it, now that I have retired. Basically, I have begun very carefully trying to take my dressing more public. I believe that I should be able to express my feminine side without reprisal and hopefully without concern.

My dilemma is this. I want to tell my dentist about my dressing, in order to see if she would support my desire to come to the appointments dressed as a female from this point forward. I don’t want to harm my relationship with my dentist, but I am hopeful that she would encourage me to dress as I want. My thinking is that once I have crossed this bridge and agreed to always come dressed as a woman from now on that it will provide me with a true success in my quest to become accepted dressed as a woman. Continue reading →