It shouldn't hurt if you are both taking the time and care to loosen you up properly.
It's a little like a trust fall exercise, except you are gently easing a dick into a butt for the first time.
It's supposed to feel at least neutral if not good yet, and should not hurt.
Did it hurt to get in? Ive never had a cock in my ass but think about it often
If you've never been fucked then you can expect that it will hurt a little. For a first experience I would not recommend a very large cock, especially if it's fat. I played a little with inserting "objects" to get familiar with the feeling. So when a guy I liked slid it in my well lubed ass the first time, it felt weird but good. Dildos are nice but a totally different from being fucked by a man. Once you're used to it, and like the feeling on your prostate and just the general feeling of being penetrated as part of mutually pleasurable sex, it's easy to get used to longer, thicker, thinner, shorter and any other guy. I totally agree with the above post that compares guys that were great and not so great, unrelated to the size of their dick.
My first was just the right size for taking my cherry. He was about 8 inches long but thinner with a very nice head. He took his time and made it extremely pleasing for me. As I had more experience, Ive had bigger ones, butt I prefer smaller longer to really please my prostrate. Biiig ones dont work for me. Just my two cents!
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