Going from my own experience...
Back in 1999, I had surgery down at the anal ring. Even having to go to the bathroom, at that time, brought excruciating pain to me. Over the years that pain did go away but I always felt that, because of the surgery, my anal ring was smaller/tighter than normal.
Amazing what the mind can do to itself.
Since I live in the "Land of Perpetual Bottoms (Seattle area)," I was always wanted to top. Which didn't bother me at all.
Every now and then, though, I was curious to bottom, Counting this year, I've only bottomed 5 times.
The first two were very painful and so we stopped and I ended up topping them.
The third time was with someone who is now an ex. It was painful with him topping. So I topped him.
But the seed was always there in the back of my mind: They get so much pleasure from bottoming. Am I missing something?
In 2016, my desire (mindset) to bottom had taken a dramatic leap forward. It was all I could think about. I even had a wet dream about it. A guy I had hooked up with the previous year had friended me on Facebook and we began talking again. He's one of the most good looking guys I've ever met. Even today, he ranks in the top three. Previously, we had only done oral on each other.
Now, i started thinking about him topping me.
His cock was 7 1/2 and average thickness. Now, after all this time, I knew how bottoms prepped themselves beforehand. One ex told me his procedure and I followed that. Understand, all i did was clean myself out. I didn't practice with dildos or anything else. All I did was make room, if you know what I mean.
So the night arrives and we go at it.
Kissing
Making out
Feeling each other up
We're rolling all over the bed and I felt myself relax in his arms and told him: I want you to fuck me.
I decided I was going to the type of bottom, for him, that I like when I top.
His eyes just lit up. He wasn't expecting that. Just an oral session. He puts a condom on but after a few moments of stumbling I tell him I don't want him to wear it. I was (and still am) on PReP. He takes it off, fingers me with some lube and then lubes himself up. He starts to slide it into me.
At this time, I flashed back to all the other times I tried to bottom and the pain it caused. Just as quickly, I put it out of my mind.
I wanted him!
I wanted him in me!
As he starts to push in, I push down and he, effortlessly, slides all the way to his balls.
As soon as I feel his balls hit my ass, I wrap my legs around him. His eyes widened a bit as he hit bottom.
My cock, which was hard to begin with, just seemed to EXPAND in hardness.
And it stayed that way the entire time!
I had never felt my cock so big in all my life!
We fucked for at least 45 minutes. I kept edging myself has he fucked me. When I removed my hand, because I was getting close, he tried to grab it. I told him no. Just fuck me as I wanted to see if I could cum from just his fucking me.
Eventually, he gets ready to cum and picks up the pace. All the time he is pushing into me, I'm pushing back. When he starts to pull out, I clinch down. He shoots a big load into me, my very first load remember.
And it felt good!
He collapses on my chest and we start to make out again. He rolls over onto his back, pulling out.
I straddle his chest and just start masterbating. Ten seconds later, I cover his chest with my cum with a couple ropes hitting his face. Then I collapse on him as it was one of the more powerful cums I had ever had.
The lesson here, OP, that I learned, is that DESIRE and WILLINGNESS and being PREPARED ahead of time, can make anything happen.
I hope this helps!
Sklar
