I didn't respond in this thread previously because, the first few times I tried it with an ex it was an absolutely Horrible experience, he got carried away, it was painful, I did not have fun- anways.

Recently this changed. I was very skeptical and weary about it at first, but I really don't want to judge the act from those few times with an amature, so I figured I'd give it another go, so to speak.

I was glad I did, he was very clean and slow, almost 'professional' about it in a strange way. He already knew how I felt about anal and got lots of lube, plastic gloves, wipes, my vibrator, a small butt plug, and a trash can for later use. I wasn't quite sure what to think of it all, I never really gave thought to any of the items he put on the table except for the lube. He told me straightaway that if there was any pain we would stop, as nothing good could come from that. He made me feel comfortable with the situation, and he had me bent over the bed and started from there, working up slowly.

It was still uncomfortable, but- it didn't hurt at all and eventually it was Okay. The vibe was used as a slight distraction, having it placed on my clit. In the end he was able to really fuck me and wow I had my cum leaking down my leg, covering my hand and vibe, and even dripping on the floor XD

I can happily say now that I'm more comfortable with anal than I ever had been previously =)