I have never been anally penetrated in these 34 years of my life. I want to experience it but can't gather up courage enough. Is it extremely painful? Is there at all any pleasure involved in bottoming? How to overcome the fear and how to get prepared?

 

It does hurt a lot. It takes a lot of practice and a lot of relaxation. Some people take a year or longer until they start enjoying it. Some guys do not take that long. It depends on how relaxed you are. The only way to get prepared is by relaxing yourself as well as using a lot of lubrication. Remember, the anal cavity is a muscle. So the more you practice, the more it will relax. After a while, you will learn how to relax it and then you will start enjoying it. However, some guys will never enjoy it and they are called tops. Some guys will enjoy it a lot and are usually referred to as bottoms. The bottom line is; try it so you know if you are really a bottom. If you are, great. If, after a while, you don't enjoy it, don't worry, someone has to be a top too.