I'm 67 years old and weigh 250 lbs. I'm also mostly bald. I've been on HRT for years and have large breasts, a feminine butt and lovely shapely legs.
When I see myself in the mirror, if I ignore my lack of head hair, I see a woman. Even my genitals barely show. I've seen more than a few women who have more "hangy-down" stuff than me.
Since my discomfort was more with my body than social role, I'm OK with wearing male clothes, although do dress androgynously often. In the summer khaki shorts, sandals or tennis shoes and a polo shirt are pretty gender non-specific.
I wear some men's underwear without a fly front, like Jockery Elance. I also wear women's underwear and it's not really much different. I have size 12 women's tennis shoes instead of size 10 mens, but that's not that obvious.
I have always had lots of women friends and very few male friends. I've been in the League of Women Voters for over 20 years. I recently joined a group of a dozen or so, "Nasty Women" for drinks and snacks. I also do water aerobics with a group that typically has 18 women and one or two men. I'm usually topless at water aerobics, despite my substantial boobage. I'm never has anyone suggest that I cover them up. At family gatherings where the men and women drift away into separate groups, I'm always found with the women. So, I'm socialized as a woman.
I have no trouble in the men's locker room. No one is going to point out that I don't have a visible penis. That would violate homophobic rules, by admitting they were checking out my genitals. Likewise, no one is going to tell a fat man that he has boobs.
Women, either consciously or un-consciously seem to notice that I'm "safe" and that it's OK to be friendly to me. Women DO notice boobs, as much as men do. At a few trans* groups I've been mistaken for an FTM.
My only complaint from my wife and daughter is how my nipples stick out when wearing a tight polo shirt. Solution: A size larger shirt or a woven shirt.
My life has not been disrupted by my transness, yet I now have the female shaped body that seems right and proper to me. Even my name didn't have to change much. My middle name is Randall and I've been know as Randy most of my life. I now have several credit cards and other ID cards where I am Randi.