Does it get better the more you do it?

For the longest time, I was curious how anal would feel. It looks like there is pleasure in it. I finally decided to try and ended up using a dildo on myself. I have heard that having something inserted in your anus while having sex can intensify the feeling, but wanted to see how it felt initially before bringing up the subject with my gf.

I didn’t work my way up in size, I just started out with using a dildo. It wasn’t a huge one, and it is actually smaller in size than I am. When I started, it was a little difficult getting in. The dildo was not what I would call very hard. I finally started getting inside and at a point, came up to some resistance. As I kept trying to push it in, the resistance gave way and it more easily started to go inside.

I managed to get the whole thing inside, to where I could feel it pushing against me. Simply having it inside of me did not do anything for me. I then started thrusting it back and forth a little, but again, I did not feel like it was pleasurable. There was not really a point where I enjoyed any part of it. At times, it was a little uncomfortable, but it was not painful in any way.

I am not one to give up on the first try, but to me when you experience pleasure, it is usually right away. Is this one of those situations where the more you do it the better it feels? Should I have started with something small and work my way up in size? Is there truly a spot in the anus that can intensify the feeling? I am wiling to give it another go if it is worth it. Any tips or advice would be appreciated.