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. 

[liger]

Honestly, not painful in my case. I’d had plenty of objects, butt plugs and dildos up my ass in the years before a guy fucked me for the first time. I was lubed up and was well prepared for what it would feel like. I was more self-conscious about my hole being a bit too wide for his smallish cock, as he was pushing my legs and ass cheeks together to get a tighter grip.

[TommyTheVirgin]

Very painful.

He was well lubed and gentle but I couldn't relax.

It felt like I was being ripped in half.

I was crying and screaming the whole time.

[Falls727]

I never had pain when I was first fucked and bred. I have always had an amazing fuckhole that can take guys of all sizes. 

[NLbear]

No pain at all. I LOVED it! I was hooked 😉 

[hexfet]

First time was a little rough although he was a quite the monster so maybe that’s a bit of it.  That said I get rock hard every time I think about it. :)))

I’m wicked tight, but while he was big at least he wasn’t much thicker than me so I had a fighting chance.  Was so into him, and he didn’t believe I’d never been fucked before.  But once he started working into me, I think he decided I was for real.

Mostly was a great fuck, although, he short stroked some since my deep ring wasn’t letting him in.  Bounced off of it from time to time and made me jump good :))

Was at a time we should have been playing safe but didn’t. Fucking raw was a treat for him you could tell. Asked if he could cum in me and I couldn’t think of any answer but Fuck Yes. 

That definitely pushed him over the edge and saw his whole body tense up and just slam down deep into me, muscling my poor deep ring and making me jump out of my skin. 

I was so turned on anyway I exploded at the same time which definitely mixed that pain with pleasure.

[Warmnsalty]

My first time was painful, not pleasurable at all. He wasn't that big, 6" I'd used a dildo to fuck myself plenty on my own so didn't think it would be a problem. Think it was a combination of nerves and not being able to relax... took me a while to get the hang of it. After 4 or 5 times I started to relax enough to enjoy being used. Now I like nothing better than being head down ass up for men. Even though the first times were uncomfortable I had no desire to top, knew I was a bottom, just needed to learn to be a better bottom 🙂

[EastTNbareback]

14 hours ago, NLbear said:

No pain at all. I LOVED it! I was hooked 😉 

Same here, no pain at all.  I loved it too!  I had never felt anything like that before.  I was immediately hooked.  We even caught it on early computer camera video.

 

[sneakybare]

My friends soapy dick in the shower slid right in,  a little uncomfortable but it was his virgin dick going into my virgin ass. He was rock hard and a good size and it wasn't a very skilled entry  but I took it and he couldn't wait to unload. 

 

Edited 1 hour ago by sneakybare