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Anal

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I've tried several times, and never felt comfortable. It was always very painful and I would be sore for days. I've never been able to relax and enjoy. I usually end up topping but don't really enjoy that either. Have been more into frot, oral, and mutual jackoff.
 
I am not sure what question you have or advice to give -

I don't do oral at all - I have had a great sex life even though I don't do oral - so if anal isn't your thing - stick to what you DO like.
 
I've tried several times, and never felt comfortable. It was always very painful and I would be sore for days. I've never been able to relax and enjoy. I usually end up topping but don't really enjoy that either. Have been more into frot, oral, and mutual jackoff.
Since this forum is for both advice and for support, it's not clear which way you want to go in your post.

Do all gay guys have anal sex or enjoy anal sex? No.

Is anal sex a requirement in order to have a happy or healthy sex life? That depends on whether you are able to find someone who has the same feelings about anal sex.

The thing with sex is that it is like a buffet. You don't have to eat everything on the buffet. The more things you're willing to eat, the more likely you are to be able to get a full meal from the buffet.

If you're happy with frot, oral and mutual jackoff, then there isn't a problem, as long as you're able to find other guys who like those things.
 
I do not get anything out of bottoming. If I never had to bottom again, I'd be happy with that. I will do it for my partner, however. You do what you have to, to make him happy.

Anal takes a lot of prep, from cleaning to stretching to lube choice and condoms. Dick size is a factor, and so is whether he's a good top or not. It's possible to hurt the other guy if you don't know what you're doing. A whole lot of guys don't take the proper time with the guy taking it.
 
I feel like I am missing out and/or not being pleasing enough.
 
Well, are you getting dissatisfied customers? You may never get anything out of it. That's not about pleasing, it's about being pleased. I look at it this way, if he's doing what I want, I do what he wants. The rule for hookups tends to be every man for himself. I generally won't bottom for a random guy.

Buy a big bottle of lube, some plugs of varying sizes, and practice. I've never been able to remove the initial pain entirely, and I've never felt what good bottoms apparently feel - but you can train your body not to tense up and make things worse.

When you are about to go for it, take your time and your toys and work up in size to the cock you're working with. If the guy is just trying to shove it in immediately, slow him down and take your time.

LUBE! LUBE! LUBE! I don't care what he says, spit is not lube.
 
I feel like I am missing out and/or not being pleasing enough.
Well, are you getting dissatisfied customers? You may never get anything out of it. That's not about pleasing, it's about being pleased. I look at it this way, if he's doing what I want, I do what he wants. The rule for hookups tends to be every man for himself. I generally won't bottom for a random guy.
You didn't really provide details about your circumstances but if you're doing random hook-ups or NSA encounters, Tx-Beau is correct: your pleasure and comfort is the higher priority. It's cold to say it but it is true: you don't owe hookups a good time. If you're having sex to please someone else, it's time to look at why.

On the other hand, if you have a regular partner, fuckbuddy, FWB or boyfriend and you're interested in reciprocating and doing things that he likes, then there are things that you can do to make the experience more pleasant for you. There's a Sticky in the H&W forum that has suggestions about using dildos and buttplugs to "train" your body to relax and to not associate pain/discomfort with having something in your ass.

 
I've tried several times, and never felt comfortable. It was always very painful and I would be sore for days. I've never been able to relax and enjoy. I usually end up topping but don't really enjoy that either. Have been more into frot, oral, and mutual jackoff.
Some guys use poppers for that, but they steal your erection.
 
I have had a few experiences with bottoming for anal sex. Here's my take: I like a top partner with a medium to smaller cock, it is just more comfortable. My partner just this last Friday has a medium cock when hard. We used his hard Dildo to start, then I went doggy style on the edge of the bed, and he stood and entered me that way. It was perfect; I got to feel his cock inside me, moving in and out. I was in a submissive position; I think I like that now. It was perfectly comfortable, and I enjoyed the "being used" part of it. I'm including photos of me with my Dildo for position purposes.IMG_4289.jpegIMG_3392.jpeg
 
I have had a few experiences with bottoming for anal sex. Here's my take: I like a top partner with a medium to smaller cock, it is just more comfortable. My partner just this last Friday has a medium cock when hard. We used his hard dildo to start, then I went doggy style on the edge of the bed, and he stood and entered me that way. It was perfect; I got to feel his cock inside me, moving in and out. I was in a submissive position; I think I like that now. It was perfectly comfortable, and I enjoyed the "being used" part of it. I'm including photos of me with my dildo for position purposes.View attachment 2893393View attachment 2893394
Practice makes perfect.....don't forget the lubrication !!.
 
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