Will bottoming always hurt?

[polesitter]

My first time was awful and she was Huge (10+). The Second time it was better but the condom broke so it was short. Third time was a charm. What happened in between was i became more liberal with ass play when alone. I had a 8 inch dong that was a decent thickness. i wanted to get use to stimulating my spot and taking penetration. It got to the point that the third time ended with out me touching my self the whole time. I came just on penetration. I think mindset all so pays i big part too. The third time turned me to the dark side lol i havent topped since.

[Kayden Harley]

I hate bottoming. I've done it twice in my life.. last time was little over 4 years ago. Taking a dick in the ass just isn't for everyone. I hate the feeling of having something inside of me. It creeps me out, and it just feels like poo.

ugh, just thinking of it makes me squeeze my cheeks.

[PeePeeLover]

I've had a finger in my ass before and I couldn't handle it. Not because it hurt, which it didn't, but feeling like I was gonna shit all over her fingers, hand, and bed. Couldn't find pleasure or enjoyment in it at all. I'm into piss play not shit play lol

[deuxglass]

My first time hurt like hell but I was very young at the time. But one very important thing is that it felt it right to be penetrated. It was natural. Having a cock up my ass the first time was hard but good at the same time. I felt like a girl getting fucked. And I loved him getting so much pleasure from my body. And the first anal orgasm, well that's another topic altogether!