Bottoms. Just how painful was penetration for you when you first first bottomed for a guy?

[DNG999]

Pretty painful to start. Looking back on it my top lines his cock and the entrance to my hole. For a first time it would have been better to work that lube in finger deep.

[descartes70817]

It felt fantastic. He took me home drunk and poured me into his double bed after removing my shoes, socks, pants, shirt and underpants before he got naked on the other side of the bed where his hot body was making my cock so hard that I had to stroke my shaft without being too obvious, only to realize that he was stroking his own cock too.

We briefly started stroking each other's cocks before I shifted attention to socking and licking his cock shaft, then to him beginning to sucking on my cock too to. He made me cum faster and I wanted to make him cum too but the words coming out of my mouth were "I want you to fuck me".

After a brief moment in the bathroom he was back in the bed behind me and pushing his cock into my ass until my cock was rock hard again, and he was pounding my ass and my hard cock hard until I felt him spasm and shoot his cum inside but as soon as he came he pulled out and so he could roll over and I could fuck him again

[ffabbian]

I feel like I missed out because it wasn't painful at all. I was 13 when my best friend fucked me, he was 14 and had been playing with my hole since I was 8 and had slid his cock in my hole many times  but this was the first time he pounded my hole and shot his load inside me. It felt natural and what was missing in my life. 

[ptxpau]

It hurt very little, he was experienced and small size.

[Iker80]

The first time I got properly fucked he went in very easily. I was really wanting him and I relaxed. I don't think I've gotten any better at bottoming in the years since, I'm just either relaxed, or I'm not.

[drscorpio]

It wasn't painful at all. But he did have a perfect dick for the first time - smallish head with a shaft that gradually grew to a respectable thickness. It slid right in without any fuss. I loved taking cock and cum from then on. 

[blackrobe]

He drugged and raped the 12 yo me and it was so traumatic I can't remember a lot of it. The next morning my hole was incredibly sore for many hours after. I was a small kid and he was a full grown man.

Now, consensual and adult sex? I lucked out with a wonderful sexy man who vibed with me and he fucked me so well I almost had a hands free orgasm.