These secrets were passed down to me by the venerable pole dancers of my studio, as it was passed down to them. Now, I will hand them to you - keep these secrets safe, and they will forever help you in your ventures.. :P
OK, joking aside - the general rule of thumb for any of these things (pole sits, superman, elbow holds etc) is that it will take 21 times to make it stop hurting. I don't know where 21 comes from, or whether it simply means that you have to do it over and over again, over multiple days, for your body and skin to adjust. And this has been true for almost everyone I know.
Also, flex. Flex, flex, flex. If you flex those thigh muscles, calves, point those toes, engage your abdominals, it will not hurt as much. Plus it will build really good habits :)
I am easily bruised as well - and it also gets better, although there are times when I swear I didn't even touch the pole in a spot and I get a bruise... even so, my body has adjusted and it happens less/the bruising bothers me less.