Every time we had anal it hurt in varying degrees. And we had anal every time we saw each other.
It wasn’t intentional on his part. He just had the perfect penis. Not terribly longer than average but it was so so thick. And uncut. Truly the most beautiful penis I ever saw. When it wasn’t inside of me I was sucking it. It was so perfect that I sucked it each time we switched positions. No matter what hole he came from. If you saw it you would get it. But enough of that I wanted to write a about a few times we had anal that run through my head when my hands are between my thighs.
I’ve never used lube for anal. And that night we were having a rather vigorous go at it. It was towards the end of our time together for the night. I was pushing back against him in time with his strokes. Nice and rough and lovely. But all of that friction shredded the condom and his cum filled me. I have absolutely never felt that much ecstasy in my life. I could not stop kissing him and touching him afterwards.
The second instance happened near his climax as well. We were in missionary and doing piv and suddenly he switched to holes. Missionary anal is the most painful to me. I do not what it is but my body does not like it. But I did not voice my pain. He had left enough room between us that I could look down and see his perfect penis pounding into me. Streaks of blood formed on the condom before he plunged into me and finished.
When I mentioned earlier that he was not intentionally hurting me I might have been a bit dishonest. But I am an anal whore and didn’t really mind. Prefer it actually. This last time was another switcheroo and I was very unprepared for it to happen. So much so that I yelped “ouch.” With the speed of lightning he pinned me onto my tummy and slowly entered once more. It was painful for a bit and then it wasn’t. I started trembling and he got as deep as he could and kissed my forehead.
Source: reddit.com/r/gonewildstories/comments/ljuipj/my_favorite_anal_partner