Sounds like you have gynecomastia. Sometimes gynecomastia can be painful and it is not unheard of. As for the waiting part waiting usually solves nothing. One of the only reasons I can think of for pain is a painful gland, or rubbing against something for long periods of time like a shirt or your arm rubbing against the gynecomastia. If your gynecomastia bothers you I would get it removed with surgery. Might want to check your hormones first like others say on this board. But, that usually solves nothing. Surgery is really the only positive and benefical way of getting rid of it. And since it sounds like this has bothered you for a while and you have waited long enough I would tell you go get it done. Try to set up an appointment with a PS or go through your doctor again to refer you to a specialist. Insurance may cover gland removal especially if it is painful and uncomftorable. I also have the same problem and am seeing a specialist on the 19th of this month. Hoping to get surgery a few weeks after. If money is an issue I suggest save up as a back a plan because insurance companies are a pain in the a**. But, if the condition is painful and uncomftorable there is absolutely no reason insurance shouldn't cover at least gland excision. That would be a medical reason. They won't cover lipo unless it is necessary. The consider that cosmetic. I know my gynecomastia is 75% plus glandular tissue since it is all rock hard. So getting that removed will help get rid of the crap underneath my armpit to my nipple so I don't rub against it anymore to create pain and uncomftorablness and the contour will look a bit better by getting rid of the tissue. Usually puffy nipples are caused by glandular tissue or hard tissue connected right underneath the nipple. You are definetely a good candidate to at least get gland excision. But, I hear usually excision and lipo get better results. So, your first step is to tell your doctor this is really bothering you and you are experiencing pain and uncomftorablness. He should understand and refer you to a proper specialists. If not try to find a specialist on your own and see what you can do. Anyways, good luck and I am sorry you to are going through this bs. It is a step by step process getting gyne removed so every step you advance you will be one step closer to being gyne free.