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I don't know "why", I just know that I want to dress up. At this stage in my life (60's), I don't really care so much about being a man, but there's no magic fairy who could make me a woman AND also...

If you're "out" and don't care who knows about your crossdressing hobby -- or any other intimate details you put in your journal -- that's probably fine. Personally, I stick with a paper journal. I...

I'm glad to hear it's working out for you. You are definitely taking the right approach in ensuring that the women you date know about this aspect of your personality before any commitments have been...

The crossdressing urge definitely comes and goes for me. It seems to depend on how engaged I feel with my "normal" life. It never goes away completely, but if I'm on vacation, say, there's less of an...

You owe it to your SO -- and to yourself -- to clear the air before you propose, and the sooner you do it, the better. If it's a deal-breaker for her, the cost now will be hurt feelings and maybe a...

I guess the solution is to wear a black -- or some other non-girly color -- thong the next time you pull weeds there. But really, if someone wants to come pull my weeds, I'm not going to second-guess...

I think a lot of this has to do with the sexual nature of crossdressing. People -- and especially the ones with testicles -- will do almost anything to accommodate a sexual urge. I'd even say we are...

I'm not sure what's "passable". My safe space to start was a transgender support group, where some people made no effort to pass whatsoever. When I restarted going out last fall, I went to a...

I would have felt scared, too. I think the thing to do in a situation like that is to get finished up ASAP and get out of there -- or if it doesn't seem possible, to go inside the station and ask the...

One step at a time. You did just great on Friday. What really impressed me, though, is that your wife accompanied you today. I would love for my wife to go with me on an outing and also knowing I was...

If I'm going to have to be labeled, well, I'm a crossdresser for all 4 situations. When I am dressed as a woman, I prefer to be called "Ma'am", even if you suspect there is a penis lurking under my...

JennyMay,

I also go through times where I regret choices I've made. One thing to keep in mind is that the fantasy down the road not taken isn't perfect, any more than things are down the road...

One of my deep regrets is that I didn't explore crossdressing back in my 20s. I was too busy trying to be a man and too busy trying to put the "queer" label from middle and high school behind me. The...

Jamie,

Welcome back. My attitude is summed up in "Whatever floats your boat." I am a closeted crossdresser who fantasizes about having gender-confirming surgery, but I spend nearly all my time...

Trina, the thing that made it easier for me to go grocery shopping is that I went to a store well out of my neighborhood, so I wouldn't bump into someone I knew. My plan, should I ever run into...

It's also the name of a good book.

I posted about my experience in November when my wife left town for a week and I tried to make it a full week en femme. She went for another trip to visit her parents the middle of the week two weeks...

I feel the same discomfort shopping in drab in the women's section -- and especially the lingerie department. In the other women's departments, I can feel comfortable in responding, should anyone...

I expect it will seem like heresy for me to say this, but when I see a picture of David Bowie all made up, I am repulsed. The odd thing is that I don't feel that way when I see or meet someone who...

I have noticed how a woman wearing an unbuttoned sweater will occasionally pull the sweater forward, reducing the amount of exposure, almost like a nervous tic. Even my therapist does it. I cannot,...

I do a lot of the laundry. My wife has learned to bite her tongue if she is washing clothes and comes across some of my items. Trashing each other's possessions is strictly out of bounds, and if my...

My wife and daughter were/are the things that keep me living most of my life as a man. The two most important things to me are being J's husband and A's father. That doesn't mean I don't struggle,...

With a dress, I wear a slip. With other things, I wear a camisole. Both are lacy looking and add to my enjoyment. Just as with hiking and biking, it's all about layers. As for a coat, look at the...

Kimberley, I'm with the others on this -- going out for a walk or to the library is free, and a cup of coffee isn't a lot of money. On the other hand, I can also remember some lean times when I was...

Many times, dressing up as a woman is purely erotic for me, but once I have calmed down, it's just comfortable, like being held feels. I can look in a mirror and tell myself I'm beautiful, which is...