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

[NWUSHorny]

I didn't try it until I was 21, and then with someone with a relatively small dick, but I really enjoyed it. Two or three days later I hooked up with a black guy who was similar in size to my own big dick, he fucked the cum out of me that 1st time, and since we both had to get to class didn't teach me how great flip fucking was until the next day. He and I fucked each other 3 or 4 times a week for our last semester of college and I often regret not trying to keep in touch. 

Strangely after that, I went on a kick for several months where I wouldn't let anyone smaller than me fuck me, which was really counter productive given my size and how much I love to both bottom and top.

Edited March 4, 2023 by NWUSHorny

[JamesL100]

I don't think I had seen any gay porn in pre-internet days but my first bf was more experienced and I loved it. At bedtime and breakfast 😄
Later on it took time to accommodate some super hung guys but it was usually down to finding a comfortable position 😉
And enjoying finding some versatile guys to flip fuck with 😎

[ThisBoyBottoms]

I had a pretty good teacher the first time, and while it did hurt, it was mostly pleasurable pain and adjusting to the feelings and sensations and learning to relax a little more. Seemed kinda counterintuitive, but he (the top) was right. (He was older so he had experience and was a good instructor.)

[URS2USE]

i had been experimenting with toys for awhile before i got up the courage to take a dick, so it wasn't painful at all...especially when he put the first bottle of poppers under my nose and had me inhale.  He had me bent over the back of the sofa, and when those poppers kicked in, i was begging for him to feed me that cock harder, deeper and faster, which he did.  That night...the first dick in my mancunt, the 1st time for poppers and the 1st time barebacked and took my 1st load inside my ass...i just wish that i had a video of it!!!

[Bimarried001]

Not sure if me first time counts. It did hurt but I was raped by an uncle. I’m no longer gonna say the age as I’m not sure what will get me suspended here. 
My first time getting fucked willingly hurt a whole lot as well. 

[AussieMarriedBtm]

First time for me was completely unplanned. I was just there for a BJ but half way through the other guy said.. you wanna be fucked don’t you? And I simply nodded. 

Thankfully he had a some lube on him - put some on my hole and some on him, folded me into the fetal position,, lined up and slide in.

No pain, just immense pleasure, probably helped by him not being huge and me being relaxed. I asked him to pull out way before he was ready to cum but of course like any good top he ignored this and came in me anyway.

so , in short, it doesn’t need to hurt the first time!

[backdoorjimmy]

It wasn't as painful as I expected. I'd been playing in my hole for about 3 years and was using phallus-like toys (candles, drumsticks, handle to a plastic toilet plunger) so I was more than ready. But most of the discomfort was from me bracing myself for the pain and tensing up. Once I relaxed, everything went from stressful to magical.

[evilqueerpig]

I was 17 and he as 28.  When he first rimmed me, I knew I wanted his 7" cock in me!  He was gentle, patient and it was more discomfort than pain during the initial penetration.  Once he was balls deep, it was pure pleasure and the man knew how to fuck, long and slow with plenty of kissing.  I felt his cock swell before he came.  Perfection doesn't exist but he came DAMN close.  I fucked his ass and declared myself versatile.

[LDNhungvers]

I remember my first time bottoming like it happened yesterday.

In Mai 1990 I fucked my first guy on a nice  large gay bathhouse and until Oktober 1993 I only topped…until I saw this guy in a gay sexshop with it own cruising area in the back…we catchend each others eye and went in a cabin.

I didn’t knew why, but when we started kissing I knew I wanted him to fuck me….I didn’t planed to get fucked but there was the entire time no mess….

Pain? 
No, he was really amazing to get me in the mood and the first penetration was an unusual feeling, but I like every second….and he bred me after a breathtaking fuck….

i still know his name 😉

[ErosWired]

I experienced no pain at all my first time, and it wasn’t a short fuck. I hadn’t been playing with toys or anything like that to prepare myself for the possibility of getting fucked - I don’t think I even owned a dildo at that point. Afterward when I told him I was a virgin to taking cock, he refused to believe me. I guess I must just have a natural talent for taking it up the ass.

[Piggyybttmm]

My first time getting fucked I was like 17/18....with a guy in his late 30's.....and honestly it wasn't painful at all. Infact, it felt amazing. It was prob one of the best feelings I've ever felt at that time. The guy came and I wanted to keep going....found my self a few days later cutting class and riding someone else's dick. Safe to say a cock slut was born lol. 

Looking back at that, and knowing what I know now...that was def confirmation that I was meant to be a bottom and take dick. It's my absolute favorite thing

[swall0w]

I was a very immature 13yr old and it was very painful, i hated it and he, a teacher at my school used no lube and was very rough, it wasnt until he was arrested for abuse of another boy that I realised how much i loved him and even though anal was always painful with him I still wanted him, it was my next male on male encounter when I realised it didnt have to hurt

[nastypig80]

I was younger but it didn’t hurt at all. Felt natural and amazing. Helped that it was raw and he’d eaten me out to lube me up I guess.

[1hornyjohn]

As memory serves- and it was a long time ago- no problem or pain whatsoever 

[hungry_hole]

3 hours ago, nastypig80 said:

I was younger but it didn’t hurt at all.

I was also young, on my first visit to the YMCA in New York. Maybe the guy wasn't very big or maybe that I knew about lube from   my bottom friend who had recommended me I stay at the Y. I still remember the guy in his 50's moaning, pulling out and quickly leave the room. My first bottoming experience must have been very good because I became hooked to bottoming and taking anon loads.