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Been type one for twenty years and will confess to injecting through clothes, although not thick ones. Although I did absentmindedly attempt injecting through my motorcycle leathers once. It didn’t work.
It works for me every time, can't say i've ever noticed needing to use more pressure either, the needles are so fine and sharp nowadays it;s almost like the weight of the pen is enough to puncture clothing and skin.
I have done. I have also been told not to since it blunts the needle plus alters the depth. I can usually engineer things to use a tummy or accessible site (Summer is great with shorts - appreciate others may have other items of clothes that get in the way but having bare legs is a godsend! Would inject through thick jeans or wolf jumpers but this items yes not issue.
Girl or boy thing?
I would only say the girl thing matters if you are wearing a dress. Otherwise, it is easy to lift a short/jumper/t-shirt and inject regardless of gender.
Dropping your jeans or injecting through them?
Depends high you wear your jeans and how low you inject.
Unless you keep your nipples warm with your jeans and inject in your unmentionables, what is wring with lifting your short or prising it apart between a couple of bottom buttons?