(NSFW) How can I get myself to orgasm with a condom while having sex?

Totally TMI here.

I grew up a good chunk of my life masturbating by proning – meaning rubbing myself against a surface. I wasn’t was aware that the “normal” way was to do it by hand until the end of high school, when I started to understand jerking off jokes.

I proned for a long-ass time until my senior year of college, when I finally had a girlfriend that I became sexually active with. It seemed to be a gift and a curse, because while I was always able to satisfy my girlfriend and last in bed, it’s VERY hard for me to get off inside of her with a condom. Without a condom is totally fine. But with a condom – it takes me forever and it’s such a pain (not literally in the physical sense – it’s just tedious).

Eventually I weaned off proning and got to do it by hand.

I still have problems getting off inside my girlfriend with a condom though – I’ve just been so used to rough friction. I really want to work towards fixing that. Another issue I’ve been ashamed to admit is that – I fucking masturbate so much. I really do. I’ve been keeping track this year on an Excel spreadsheet and so far it’s an average of 2 times per day. I’m the kind of masturbator who does it even during work when I’m alone at my desk, and my job is really boring and dull so I end up turning to masturbation to pass the time.

I believe I have to wean myself off masturbating so much, and not only that but I should only masturbate with a condom on just to get used to the feeling.

Right? I mean – if there are other creative ways to get used to a condom, I’m all ears.