You might have a very tight frenulum - the part that attaches your foreskin to your shaft at the back. Has this always happened? If this happens every time I would go and see a doctor. There is probably things that can be done - for example some people are also born with a 'tongue tie' - where the stringy bit that attaches the tongue to the floor of your mouth at the front is too tight so they can't move their tongue properly and sometimes surgery can release that. If you do have a tight frenulum you are not alone - I worked as an escort and had one client where this happened, he bled everywhere - thankfully not in me as condoms are regulation, and I've heard of it happening to other men too.
You might well be hypersensitive on the glans area - the head of your cock, which might just be natural, or you could have an infection or skin irritation that makes it like that. I can't stand direct pressure on my clitoris either - but I guess its easier to ensure it doesn't come into contact with anything!
The best thing I'd say is go to your doctor, or even better your local sexual health clinic and they can refer you to a specialist if needs be.
Also always carry a tube of lube with you (which should be used with condoms anyway to stop splitting) and make sure the girls lubed up enough - don't worry about offending them, just explain why and they'll be fine - and if they aren't tell them to bugger off. If you are really hypersensitive on your glans - wear an extra strong condom that might protect you a bit from too much friction.
Hope that helps.