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I truly sympathize with your problem because I know how many unpleasant situations can cause such a problem.
From the details you provide me I can say that it can be several causes to your problem. First, and most common, is allergy, as you mention. You should check if you are allergic on some not so common things like lipstick, for example.
There are on market some non-allergic natural lipsticks and you should try them. Also try to use Vaseline before lipstick-in can also help.
Also, from symptoms you mentioned I guess it could also be condition called angio-oedema.
It is one condition where fluid parts of blood comes out from blood-vessels and make your lip swell.
If you don’t know the right cause-try to affect the consequences.
Us of some antihistamine drugs can relieve your symptoms and minimize your attacks.

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Hello. I have one strange problem and several times I have searched for medical help and opinion but no one was able to help me.
Sometimes, I feel itchiness in my lips especially in my upper lip.
With what is this condition connected I really don’t know but after a few minutes my lips are starting to swell.
You probably wouldn’t believe when I would say that my lips become five times bigger than usual. It all lasts for about hour or so.
I suspected that maybe allergy did something with this and I did some allergo-testing but nothing was discovered to be potential allergen.
I was wondering if someone had similar problem and hopping that I will get any help on this mater.