i assume, from my own experience and logic, that the first time will always hurt, unless the anus muscles are naturaly too stretchy, which isnt the case usualy. First time you gotta take it very slow and patient. And lube up..

well, in my particular case, i loved it when mine was slowly going into her ass lol

lol I didn't have a clue what I was doing but I think he did

I loved my first time, he took it slow at first . My legs was sore for a couple of days .

Hurt a first but I've loved it every since...

Yes mainly because I wanted it so badly, my desires and needs for years finally a reality, it was not as comfortable as now of course I had some pain and I learned how to prepare myself from that point, I did love it and knew i could and would not stop needing or receiving anal

I do know what you are talking about. I have been on both ends of that.

Mine was so gradual that the first time a real cock entered me it didn't feel all that big. I started out by getting fingered. That felt so good that I looked for house hold item to insert, back in those days I had never heard of a dildo. I can remember inserting magic markers, my sister's hair brush handle, tooth paste tubes, and gradually worked my way up to larger things.

I was fucked in the ass using toys along time before I had the real thing which was painful the first couple of times but I gradually began to enjoy it and enjoyed having the real thing even more!!

My first time was painful. He was so big he only went half way in. After he came it felt a little better

Not really. Traded a ton of emails and pics with a guy I met on Craigslist. We went to his boat, went underneath. He had a great cock, but you could tell it was all about him fucking me. When he finished, he just sat across from me and watched me masturbate. Didn't after to help or anything.

My first time was with my neighbor's cousin, he was a year older than me but I knew him from my school. It happened after all three of us were swimming in my neighbor's pool. My neighbor had to leave with his mom suddenly but me and the cousin stayed and waited to get our rides home. We were changing out of our swimsuits when he got weird and physical and pressured me to suck him. Then he basically forced himself on me and fucked me for about two or three minutes. It really hurt and it was unexpected. Yeah I was a little turned on by it but it was a lot to process cuz it happened so fast. So no, I didn't like it but looking back, I have find memories of it haha.

I've had anal 5-7 times...not terribly painful. The men I was with were slow to stretch me.

But it doesn't make me cum so I don't see the point. I spend the entire time worrying that there's going to be poop involved that I can't enjoy it.

Not much draw for me. If my fuck buddy REALLLLLLY wants it I'll consider it.

I havent tried yet .. i would like to try