Sometimes in the heat of the moment my ex has entered me too quickly and it hurt... (a lot) I personally don't like the pain but after a minute or so it goes away and then its feels like pure ecstasy. Also I'm very tight so lots of spit has to be used.
one thing I miss about him is that sometimes he would surprise me. he was very vanilla but there where time wheN he fucked me like a bull. those where always the best sessions.
I only have that sensation when I'm on my back getting fucked. It doesn't happen when I'm the one controlling the action (for lack of a better way of saying it).
If there is the slightest bit of pain, you're doing it wrong.