Originally Posted by
nylust
Or maybe the OP is just searching for encouragement and help to realize a very common fantasy. Pretty much describes how I first began bottoming. I wanted it to hurt and feel desperately out of control. I did go see an aggressive top, she's no longer working, and when I told her I was a virgin who wanted to be hurt she went for it. Probably not as hard as she could have but she did work me over in a very dominant way.
She bent me over the back of the couch so my but wasn't able to get away from her. Started with a few fingers with a bit of lube, but very rough and uncomfortable. Then she shoved it in an pretty much went to town as I'd requested. Decent amounts of humiliation mixed in. When I started getting really turned on by the pounding, that happened pretty quick as the pain subsided, she started inserting her fingers too to keep me stretched and uncomfortable.
Sadly it didn't cure me and now I go looking for bigger and meaner all the time.