I've tried bottoming twice. Once last year around this time with my ex-boyfriend. I didn't know much about it and he just tried to put it in with barely any lube.. bad idea! I had the opportunity to try it again back in October of last year with a guy when he ended alone at my house for a few hours. I had looked up some stuff. We used a lot more lube and he even fingered me a bit but it still didn't work. It was really tight and the further he pushed in I got a sort of burning sensation. I've played with my anus before during masturbation and I got about two fingers in there before it got really uncomfortable and had to stop. I have a guy that I really like coming over next weekend and I would like to bottom for him. I can only think about my two failed experiences the closer that I get to hanging out with him and I'm nervous it's going to happen again. Any suggestions?
There are so many variables, it's difficult to give a definitive answer as to what works. It is often a matter of your own shape and size as well as your partner's. Lube is for sure necessary, but position matters as well. Given this whole set of variables, you now have the tools, so to speak, to be a little scientific about it. Come up with a hypothesis, based on his size and shape, and then experiment with what you can control, i.e. position, trajectory and speed of entry (Sounds like instructions on how to fly an airplane ). You will probably feel an almost unbearable sting for about the first 30-40 seconds, but if you can endure this, and tell him to stop for a bit to get a breather, go for it!
The burning sensation may be the same as the sting I alluded to, but if it persists for longer than a minute, try something else...but don`t push yourself, it may just take some training with a dildo that is thinner than your guy.
The biggest thing you can do to make it easier for a first-time bottom is to give the bottom as much control as possible. Either riding him, or doggy style with the top understanding that he shouldn't move at all and allow the bottom to control thrusting, will make it much easier for a first-time bottom.
