Crossdressing

[WolfgangD]

I prefer to keep my clothing more masculine, whether or not I'm pretending to have one on the way. I just ... dunno. The one time I cross-dressed on purpose was for a play back in high school, and even that made me deeply uncomfortable.
And, well ... with a few local friends who are in various stages of gender transition, even if I were comfortable with it, they'd probably feel like I was mocking them.

[mpregisamazing]

I've done drag for an amateur drag show in college. It's not something I like to do frequently

[littletwink]

I didn't see a thread about this anywhere on here but i'm just curious on how many of you out there crossdress? I know there are a few pregnant crossdressers on here but does anyone do it without a big bump?

Yes I crossdress often, but I also have many days when I may be appearing to crossdress but am actually dressing as a woman, because I feel as a woman on those days.  I have never crossdressed for entertainment purposes but have no problem with people who do.

[avant]

On rare occasions, I do enjoy cross dressing, but what I actually go for on more frequent basis (unless at work where not allowed) is the androgynous look, in varying degrees, from "obviously male but eccentrically dressed" to "wow, he could be a girl" to "I cant tell".

[TigerFan46]

I never go all out with makeup and stuff because of the fact that I could never actually pass as a woman, and it doesn't really interest me to actually pretend to be a woman.  But I do like wearing women's clothes from time to time.  I wear panties about 50% of the time outside of dressing up pregnant with maternity clothes.  And I go with fake boobs when I dress up pregnant, because hey, boobs are awesome lol.

[Marvelous]

When I did my 3 pregnancies, as I gotten "bigger" with my prosthetic belly I found online (CHEAP), I wore a few maternity dresses along with bra and panties. I wouldn't mind wearing clothes I can fit in and my wife said I looked pretty in them. Loose-fitting and supposed to keep you cool. For me, it doesn't have much to do with gender identity, but I sometimes feel "feminine" while I identify as a male (bigender? genderfluid? gender non-conforming?). I also wore a pair of maternity jeans my wife loaned me (I was able to fit them).

[Weirdoid]

I like to crossdress at LGBT clubs and events, sadly hadn't been free to in a while.

[kpeery]

I cross dressed a couple of times just to see how it would feel but thats about it, and in one of those times I did cross dress as a pregnant woman but didn't go out in public that day idk why I just didn't.