when does it become inappropriate?

[Samantha6string]

Only a few months into hrt and things upstairs are growing faster than I really thought they would although it seems fairly typical from what I've read. I've still got allot of muscle left and have pretty large pecs. There's now a bit more than a tennis ball each worth of growth somewhat spread over my pecs but they're starting to protrude off the muscle And can't just blend in anymore.

I'm still presenting as male in public, my friends know and have been wonderfully supportive. I went over to a friends house for a swim yesterday and casually changed pretty much in front of everyone,  like I always have. when I took my top off I instantly thought of the growth I've had so far and turned around, I put a singlet on and jumped in the pool...and the singlet clung to my skin like cling wrap outlining everything pretty obviously.

I still walk around the house in nothing but jeans or jeanshorts, I know for a fact if any of the cis girls in our friend group did what I did at the pool or walked around topless it'd be seen as really inappropriate regardless of how big their boobs are....so when does it become inappropriate for me to be topless or do other social things considered inappropriate for women to do but perfectly fine for men?

[Lady_Oracle]

when they start to look like boobs 

Like to give a better idea, when your aerola expand and there is visible projection (your breast bud is easily seen) like it doesn't look like moobs but like actual female nipple/aerola.

[Samantha6string]

when they start to look like boobs 

Like to give a better idea, when your aerola expand and there is visible projection (your breast bud is easily seen) like it doesn't look like moobs but like actual female nipple/aerola.

They pretty much do. They're not massive...but they've doubled in size at least.

[Seras]

Probably about now then

[lilredneckgirl]

Look  at  it  this way.

You  identify  as  female.  you  are  so  convinced,  that  you  are starting  HRT  to  change  your  body. 
  dont  you  think  the  when  NOT  to  go  topless   in  public  point  was  already  reached? 

  bunches of  genetic  females  out  there  have  small  or  nearly  non  existant  breast  development. 

  the  pre  teen  girls,   flat  as  a washboard  at  6  or  7  years  old.

  do  they  go  topless?

  should  you? 

[Steph34]

I feel that, once the body starts to feminize, it is no longer appropriate to present it as if it were male. Exposing skin is different from wearing men's pants; the changes that occur underneath proper clothing should be enjoyed privately unless you want others to 'track' your progress. Then again, being female at heart, I myself was never comfortable showing anything other than my face and hands because I was so distressed by living in the wrong body. Even my arms did not see the light of day except inside my home. The only exception was certain vacations, which I hated because exposing my 'wrong' body really brought out the self-hate. Once starting HRT, I have also found that dressing more feminine has actually made others more accepting of me. I mean, it would be awfully hard to convince many people that one is a woman at heart while walking around topless.

[JoanneB]

For sure time to avoid swimming and topless tanning in public. Or.... time to consider a bikini  Oh... and PLENTY of sunscreen

I have a barely B cup and get along fine presenting as a male. (full disclosure, for this baldy it is sort of hard to do otherwise). I've always dressed in loose fitting clothes thanks to many other assorted body image issues. What often leads to "Male-Fail" is a combination of many factors in your overall presentation. 

If things are going faster then then your circumstances permit then perhaps low dose HRT may bring about the emotional benefits. Keeping up on the AA won't have a big impact on the feminization. You may slowly loose a bit of what is there. I've been on/off low dose HRT a few times over the decades. On top of my natural bit of gynocomastia I did get a bit bigger up top, swollen nips and bit bigger breasts. Inside a few months of stopping that disappeared