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

[slzyfckr]

It was first time I did chems. I was in mid-30s. Always a top before that but T and G made me want to get my hole used. The guy really went for it and it was sore but I loved that. Still do.

[Oldercumslut]

I think I’ve said it before on here.  

 

My 1st was 8” and there was no pain at all.  He played and prepped and when it was time, it slid right in.  Now the second guy was a pencil dick and he hurt like hell.  Just lubed, shoved it in and jackhammered away.

[BackForIt]

Guess I'm one of the lucky ones: First time I tried taking a cock in my ass was as a teenager—and there was no real pain or discomfort, I just wanted MORE cock and cum . . .

[Guest]

It went so great the top could not believe it was my first time. Before that I had fingered myself before but had never taken anything dick-sized. He ate my ass for a bit, introduced his cock and I had no pain. He didn't find it hard to move his dick either, so I wasn't too tight. I think that night he told me "there's no way you're a virgin" like 6 times. Maybe some of us really are born to be fags 😛

I'm also proud of the fact I have no memory of his name or face (I think it started with F?), but I can easily remember the shape of his cock. 

[Bruce999]

I was caught jerking off by the school janitor. He told me if I suck his dick he would not tell on me. For the next few weeks, I suck his dick. The first time he fuck me it hurt and he left me bleeding. I was scared but he said it's your pussy being broken in. By the third time, I did not bleed anymore and I started to enjoy being fuck in the ass. 

[Lily95]

my first experience i was very young and i was forced. so it did hurt because i wasnt ready nor did i want to do it. but once i was 18 i had sex and it didnt hurt i just felt super full and was breathing heavy.

[Guest]

I remember it hurting and the guy telling me to relax. He said once it's past your sphincter you'll be fine. My desire to be fucked was stronger than my desire for the pain to stop. He was right. Once he was fully inside and fucking me gently it was fantastic. 

[jmw003]

It wasn't painful at all. We used lots of lube and since we were both in middle school his cock wasn't big. Plus I had been fucking myself with candles and spoon handles.

[Bibttmmiami]

On 3/6/2023 at 3:49 AM, Bttm2go said:

No pain at all. I played with a lot of toys, so I was pretty open already.

Same for me. 

[Phallarchist]

I wish that it hurt, or that anything of note had occurred. Out of a kind of clinical curiosity, I had rushed into rectal copulation with a thoroughly mediocre specimen. I felt nothing but boredom. Regret soon followed. I should have waited for a competent, worthy male to set his sights on my undefended youth and perpetrate the bodily transgression necessary to annex my fertility to his manhood. Virginity is the object of powerful male instincts, and I had discarded it like an unwanted coin in a beggar's bowl.

The pain or pleasure of a rectal initiation with a man of real substance would likely have been immaterial. Men have hurt me sexually on occasion. Some had marvelously brutish penises and some were simply brutish by erotic nature. They all deployed their abundant phallic energy to compel me to female function and complete themselves as men inside me, so I have only profound gratitude for their attention. Memories of pain faded and the spiritual satisfaction of being complementary to their reproductive needs remained.

Rectal receptivity is a sexual service that I owe to men of excellence, and I consider my experience of penetration to be strictly secondary to theirs.

[norcalraw]

Having already been exploring putting things up my ass as a pre-teen, like cucumbers, bananas, candles, cock sized wooden dowels, my hole was somewhat prepped for taking cock by the time I took my first.  It still hurt, but it was also extremely pleasurable. I remember having my first anal orgasm when I got fucked. Let my flame and I have craved cock ever sense. 

[horndoggy]

It wasn’t too painful for me because I had been practicing for a few years on my own with various objects starting with just the thin handle of a hair brush (which was so painful I had to take it out immediately) until I finally graduated to a zucchini. My man who took my cherry (I was 21, he was in his 30s) had a large dick, and a huge mushroom head that was a hell of a lot wider than a zucchini.

The experience was only marred by my need, mid way through, to jump up and go to the bathroom. 

The only discomfort I felt during the act, and I really continued to feel for the subsequent 15 years, actually turned out to be an irritation caused by condoms. It wasn’t until I started getting barebacked that I started to enjoy getting fucked.

[hotguy02]

Very painful he was hung 8.5x5.  Top Daddy 30 years older than me I was 19.  First gay experience.  I got addicted then.   Became his complete bottom boy cocksucker

[hotguy02]

On 3/8/2023 at 2:13 PM, BobBob214 said:

I remember it hurting and the guy telling me to relax. He said once it's past your sphincter you'll be fine. My desire to be fucked was stronger than my desire for the pain to stop. He was right. Once he was fully inside and fucking me gently it was fantastic. 

I was told that same thing lol

[fetishgear]

First time I tried to fuck was when I was 18/19.  The guy didn't use enough lube and just tried to ram it in (wasn't a good top tbf!).  Put me off for a few years, and then I thought I was a top until I got someone who actually knew what they were doing (proper dom Daddy type), who showed me how to take cock, and take it good...!