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

[fetishgear]

I think when you first take cock, you ideally want a true versatile guy (who has taken cock and fucked).  Unfortunately my first guy tried to go straight in with only a bit of lube, and didn't spend time opening me up slowly, so unsuprisingly it hurt a bit.  The next few times it was like "wow, this is amazing!"

Things I wish I was told before bottoming: 1) understand what douching is and do it, 2) plenty of lube, 3) put the tip of the cock in and wait, it'll magically open and be let in, 4) take it slow to start with, then the top can go as he likes... 😉

[Rawprv89]

I was 12 and I was already using objects and fingering myself regularly so the first time I took a cock it was pure bliss and pleasure.

[jagmanaz]

Was newly out and had mostly topped.  Met this huge black guy (9" easy and thick) at a bar and thought I could handle.  Nope, hurt like a mother.  30 years later, could take it, but still would take a few minutes to relax into it.

[WillingRawVerse]

This older guy wanted to play. I was 26 and curious about bottoming, didn't use any enhancements, hoping that the top knew what he was doing as I did tell him that I've only played with my fingers and a thin dildo. He told me not an issue. Fell into false trust. All he did was eat my hole for a little bit to get it all sloppy with spit, which he did. Then he roughly shoved two fingers in that were covered in lube. He fingered my ass briefly before shoving his cock balls deep in one thrust. I yelped and tried to pull off, but he was strong and kept his hips pressed up against my ass.

I felt helpless. Then after a few short minutes, he pounded my ass relentlessly until he came in the condom. He abruptly pulled out and I took a minute to compose myself. I flipped over and asked him to suck me off. He said nope. After I cum, my fuck switch turns off. I felt so used. Disposable. Worthless. By the time I got home, I was titanium hard. Shot 4 huge loads in 25 minutes.

And looking back, hindsight is a bitch, that started me on my journey to be used by older men. Just a warm, wet, tight hole to dump their loads in. Which I found out is my biggest turn on. Especially now with enhancements. My Daddy said the other night that I was just a cunt to him (when playing). Thinking about it makes me horny.

[Johnjohn]

It was at school in a toilet and the boy who penetrated me had, for his age, 14, a very big uncut cock. It was painful but I came back for more.

[ktopper]

I have talked about my first time in other posts so will stick to the pain factor. I was 25 at the time so not a kid. The guy who broke me in was around 35 and experienced. He was also a nice guy and very attractive so that helped. He knew that I had never done anything gay before. The only lube we used was saliva, his and mine. He used his slicked up fingers to to prep my hole and then I sucked his cock to get it nice and wet. He positioned me on my back and when he first tried to enter me it hurt so he stopped. He told me to relax and push back against him. He kissed me while he pressed into me and there was a slight bit of discomfort until he opened up my anal ring and then sheer bliss as his cock entered balls deep and pressed against my prostate. I didn't know there was such a thing as prostate orgasms at the time but I did know something very enjoyable was happening. We fucked twice before I left to rejoin my GF. I was a little sore the next day, not real painful but just enough to remind me of what I had just done, more erotic than anything. The psychological pain was the worst, I had always considered myself 100% straight until that life changing afternoon. I came to terms with it and knew I wanted more. And it wasn't long before I  got more. A trucker I knew sightly fucked me in his sleeper cab which turned into a regular thing. A couple of years later I topped a guy a few years younger than me and that was my path forwards. I do not think I would enjoy topping nearly as much as I do if I had not started as a bottom.

In retrospect, my first time taking dick was perfect, a blend of pain and pleasure, with exactly the right guy. If it would have been overly painful, or if he had acted like I was just a disgusting faggot I would have probably turned my back on gay sex forever. What a waste that would have been considering how much I have enjoyed my gay side over the years.

[Falls727]

It was a cold winter’s night and I had invited this older guy over. I had only tried bottoming once before and stupidly I did not use lube. It was so painful. This time I was prepared. When he entered the bedroom I got straight to work devouring his cock and balls. He wasn’t very thick and average length. He put me on my back and slowly entered my well-greased hole. Holy fucking shit! This was not like the last time!! As he slid in and out I felt an electric charge race through my body. I was in ecstasy. I could see stars and I never wanted this to end. His breathing increased and his thrusts became deeper, faster. He looks me deep in my eyes and yells at the top of his lungs, “fuck! I’m coming!” He came so much I was leaking everywhere. As he pulled out, he scooped me up in his arms and we kissed for the longest time. This was a regular thing for us until he moved out-of-state a few months ago. He will always hold a special spot in my heart!

[Orionxxx]

As I've mentioned in other posts, I lost my cherry at 14 to my 16 year old best friend who lived next door. After first getting me to play with his cock and suck him to completion, he spent a few weeks getting me accustomed to the idea of being fucked: eating my ass, fingering me, and dry humping my crack. The first few times he actually tried to penetrate me, he went too hard and fast (no surprise) and I made him stop. Eventually, he made me take a few shots of his dad's whiskey, lubed his cock and my ass up with KY, and shoved his thick cock all the way up my butt. I think he probably wanted to be gentle but being 16 he went hard and fast, ignoring my yips of pain and blowing his load in a few minutes while I cried face down into the pillow. I went home with a sore leaking ass, feeling very weird about everything; but in a day or two, I was back over at his house getting fucked again in the basement playroom. He fucked me regularly for the remainder of summer vacation and though it became less painful with time, I never found the act itself pleasurable. Yet, at that impressionable age, my brain began associating my partner's need to penetrate me with my basic sexual identity, so that even the pain was intrinsic to sexual play and desire. To this day, though I have often topped (on request), my sexual self-concept is very much as a willing hole to be penetrated.

[Orionxxx]

12 hours ago, Johnjohn said:

It was at school in a toilet and the boy who penetrated me had, for his age, 14, a very big uncut cock. It was painful but I came back for more.

That's what's striking to me in retrospect, how painful my first time was and yet how I returned for more almost immediately. The whole experience was just so intense, it's as if I needed to keep reliving it, pain and all

[Orionxxx]

On 3/4/2023 at 5:13 PM, Bimarried001 said:

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. 

Same. There wasn't some magical threshold when the pain stopped and bliss began: it just hurt like hell the entire time and left me very sore the next day. The entire experience made me feel degraded, but in a way my young self could never have really understood, the degradation itself became a thrill that I would actively seek out.

[Orionxxx]

On 3/4/2023 at 11:47 AM, bbslutuk said:

In short, yes, the first time hurt a little bit, specifically at the beginning. I was 17, limited options on getting lube or a dildo, so before I met up with the guy, I was just using spit and my fingers to prep for taking an actual dick. 

 

However, I was very lucky that my first time was with an older and experienced top, he quite quickly picked up when he slid inside me that it wasn't feeling too great for me, helped me with more foreplay and ate my arse, then once he tried getting inside me again, we took it very, very slow whilst fucking.

 

It did hurt the first couple of times, but after that I found it was pretty much fine. Obviously dick size plays a factor as well, it's easier to take a 6 inch average girth dick compared to a 10 inch, heavy girthy bastard lol! 

 

My personal advice to those who are brand new to bottoming would be: 

1. Practice in advance by yourself, get used to the feeling of your fingers or a dildo inside you 

 

2. Use lots and lots and lots of lube, there's never too much! My personal favourites are called 'Spit' and 'Spunk' and both are affordable (I literally used the 'Spit' lube at a sauna in Blackpool this weekend when receiving anal and it's a great lube)

 

3. If you're able to, get some buttplugs and work up the sizes, you'll find your butt gets way more used to them if you practice semi-regularly 

 

4. Tell the top if it's hurting, be honest with them, take a break, lube up more and use some toys first before they get inside you 

Super tight bottom here, this is great advice, would just reemphasize relubing often if the fucking continues for an extended period.

[WillingRawVerse]

On 3/4/2024 at 5:57 AM, ktopper said:

I have talked about my first time in other posts so will stick to the pain factor. I was 25 at the time so not a kid. The guy who broke me in was around 35 and experienced. He was also a nice guy and very attractive so that helped. He knew that I had never done anything gay before. The only lube we used was saliva, his and mine. He used his slicked up fingers to to prep my hole and then I sucked his cock to get it nice and wet. He positioned me on my back and when he first tried to enter me it hurt so he stopped. He told me to relax and push back against him. He kissed me while he pressed into me and there was a slight bit of discomfort until he opened up my anal ring and then sheer bliss as his cock entered balls deep and pressed against my prostate. I didn't know there was such a thing as prostate orgasms at the time but I did know something very enjoyable was happening. We fucked twice before I left to rejoin my GF. I was a little sore the next day, not real painful but just enough to remind me of what I had just done, more erotic than anything. The psychological pain was the worst, I had always considered myself 100% straight until that life changing afternoon. I came to terms with it and knew I wanted more. And it wasn't long before I  got more. A trucker I knew sightly fucked me in his sleeper cab which turned into a regular thing. A couple of years later I topped a guy a few years younger than me and that was my path forwards. I do not think I would enjoy topping nearly as much as I do if I had not started as a bottom.

In retrospect, my first time taking dick was perfect, a blend of pain and pleasure, with exactly the right guy. If it would have been overly painful, or if he had acted like I was just a disgusting faggot I would have probably turned my back on gay sex forever. What a waste that would have been considering how much I have enjoyed my gay side over the years.

IME it takes bottoming to enjoy being a top. As a Bi guy, I'm sub with men and top with women and trans. But I want to bottom for a sexy trans as well. Sometimes with the right guy, we'll flip fuck. But thats a rare thing. So I know from bottoming how to top with a mix of pleasure and pain without injury.

[chiilfuck]

Hello,

For me, no pain whatsoever. I wanted it so badly; my hole was wide open!!!!!!  😊😊

chiilfuck

[KindaBasic]

It actually quite wonderful. 

[KylerIsTrash]

The first time didn’t hurt at all. I wanted as much of it as I could get. Since then I’ve found pain or discomfort is inversely related to how attracted or horny I am to the situation. If I’m real into it, the 13 inch shampoo bottle of a dick slides right in with me begging for more. If I’m not into it, the 3 inch chapstick dick kinda hurts. Also, since  I started partying, anything sober is usually some sort of uncomfortable. Enhancements kinda ruin sober sex.