Does bottoming hurt?
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Personally I think it depends completely on dick size. If it's big it's gonna hurt.
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It mostly hurts at the beginning but you hole is going to ease pretty fast if you're relaxed. What bothers me the most is the pain of the cock going too deep
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yes - it does!
But that is why I prefer to top! 
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I was bottoming in the beginning (I'm top now) so it hurted me the most first few times, then very soon it was much less (but still uncomfortable and little hurt) but I think all those guys who I was with were not putting enough lube in my ass - sometimes I was having sex without any lube and then 1 guy putted lots of lube in my ass and it didn't hurt me a bit, I was actually really enjoying it - it was magical!, so I think this was the KEY for minimum hurting and maximum enjoyment (but unfortunately I can't say for sure that this is the case cause I stopped bottoming soon after that experience so I think you should definitely try it and see if you'll have same reliefed experience as I did, I'd be glad to hear if that's gonna be a solution for you)!
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the first time, yes!
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I gave a pretty comprehensive overview of the bottoming experience earlier in this thread, but one thing I want to add is that when both of you have a romantic and mental bond, it is such a wonderful experience. I met a guy late last year and we have very deep and loving feelings when we fuck, and I honestly love every time we get together. The look of love and passion in our eyes while we fuck is amazing. Sometimes we stop in the middle and just stare into each other's eyes because it is so special. And I can see in his eyes that I am more than just a guy he hooks up with, which makes it even more special when he plants his seed deep inside — oftentimes more than once in the same session.
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Wish we as a culture would get over the idea that bottoming has to hurt, or that one's first time has to hurt… that creates anxiety in first timers which paradoxically leads to more pain. Fact is, it doesn't have to hurt, not even the first time (didn't for me). Not that it doesn't ever hurt, but if it does, there are other factors involved (too much recent sex, health issues down there, discomfort with partner, etc.)
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It depends… if you bottoming often, don't!
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When you first start, it might hurt a little bit. It is unconscious, but you can't fully relax your anus when you're trying out this new experience. You will always be a little bit nervous.
So, go generous on the lube! REALLY generous! Don't worry about exaggerating, when it comes to lube. At the penetration moment it might hurt, so go slow. Ask for a gentle slow fuck at first. After a while, when you're used to the sensation, then ask your partner to go wilder

If you bottom regularly, you will start to relax more, and your unconscious mind will start to relax as well, and it will not hurt so much anymore.
Best of luck, I hope you'll learn to enjoy bottoming as much as I do

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It never hurt me, even the first time
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When you first start, it might hurt a little bit. It is unconscious, but you can't fully relax your anus when you're trying out this new experience. You will always be a little bit nervous.
So, go generous on the lube! REALLY generous! Don't worry about exaggerating, when it comes to lube. At the penetration moment it might hurt, so go slow. Ask for a gentle slow fuck at first. After a while, when you're used to the sensation, then ask your partner to go wilder

If you bottom regularly, you will start to relax more, and your unconscious mind will start to relax as well, and it will not hurt so much anymore.
Best of luck, I hope you'll learn to enjoy bottoming as much as I do

;D
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I guess it depends on how relaxed you are, how much lubrication you've got going on and of course, how thick he is.

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Link: https://www.advocate.com/current-issue/2017/3/03/shame-free-tips-how-be-better-bottom
Bottoming is fantastic, and more people should open their minds (and their legs) because with the right preparation and the right person, the experience is mindblowingly good. Use plenty of lube and have faith.
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Link: https://www.advocate.com/current-issue/2017/3/03/shame-free-tips-how-be-better-bottom
Bottoming is fantastic, and more people should open their minds (and their legs) because with the right preparation and the right person, the experience is mindblowingly good. Use plenty of lube and have faith.

:afr:
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It does not usually hurt. Even the first time with a school mate when we didn’t know what we were doing wasn’t bad, but then we used over half a tube of lub. It was uncomfortable briefly but soon turned into a great feeling. Just need to relax. If it is a very thick long one I find it better to straddle the guy and lower myself onto it a my rate. Once it is in He can flip me over and pound away without pain just that great feeling one gets. Once the first guy cums in your aass the rest can following using his cum as lube without pain. :anal2:
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It does not usually hurt. Even the first time with a school mate when we didn’t know what we were doing wasn’t bad, but then we used over half a tube of lub. It was uncomfortable briefly but soon turned into a great feeling. Just need to relax. If it is a very thick long one I find it better to straddle the guy and lower myself onto it a my rate. Once it is in He can flip me over and pound away without pain just that great feeling one gets. Once the first guy cums in your aass the rest can following using his cum as lube without pain. :anal2:
The rest?
How many do you have in mind?
:cheesy2:
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It does not usually hurt. Even the first time with a school mate when we didn’t know what we were doing wasn’t bad, but then we used over half a tube of lub. It was uncomfortable briefly but soon turned into a great feeling. Just need to relax. If it is a very thick long one I find it better to straddle the guy and lower myself onto it a my rate. Once it is in He can flip me over and pound away without pain just that great feeling one gets. Once the first guy cums in your aass the rest can following using his cum as lube without pain. :anal2:
The rest?
How many do you have in mind?
:cheesy2:
Whoever is there
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It does not usually hurt. Even the first time with a school mate when we didn’t know what we were doing wasn’t bad, but then we used over half a tube of lub. It was uncomfortable briefly but soon turned into a great feeling. Just need to relax. If it is a very thick long one I find it better to straddle the guy and lower myself onto it a my rate. Once it is in He can flip me over and pound away without pain just that great feeling one gets. Once the first guy cums in your aass the rest can following using his cum as lube without pain. :anal2:
The rest?
How many do you have in mind?
:cheesy2:
Whoever is there
Btw You included your answer in my quote..
You should fix it.. ;/)
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In my case, no.
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without prep: GOD YES
with prep: its okay. i'm like in the heat of the moment "Yeah put it in me" and when he does i'm like "Slow down bitch it hurts…..this is not as fun as porn make it looks"
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