How long to get used to anal

My only experience of having something inserted in my arse is the Dr's finger for a prostate exam. I've had few of those recently because of a cancer scare (turned out to be no cancer thankfully). I found I really quite enjoyed the sensation. I would seriously like to experiment with anal sex but i think I'd start with something finger sized, with pints of lube, and gradually build up to something around normal/average penis length/circumference. I don't anticipate that I'd go any larger than that. As I'm not keen on doing this alone and as my wife is not interested I need a buddy to play with.
 
This is probably the wrong forum, but who cares eh?
My wife decided, unplanned and undiscussed to use the largest of her butt plugs in/on me.
It's the first time I've ever had anything up the back door, and 24 hours later I can still feel it.
I enjoyed it (even though it was painful at times).
So, my question is...will it feel like this every time if we carry on (I'm already considering buying her a pegging kit), or do you get used to anal and don't feel like your butthole has been turned into a train tunnel?
Usually women feel uncomfortable before fluid comes out of the anus, but once it comes out, everything becomes enjoyable.
 
Inflatable butt plugs are excellent for starting small and stretching for more in a short period of time. A few pumps at a time, little breaks to relax in between. Its how I started out stretching for our Hismith machine. Wasn't long before I didn't need the inflatable anymore.
 
You've got to get out of the big is better mindset when it comes to anal. Leave your ego at the door and stick to natural sized toys, if you're not enjoying it you probably need smaller not bigger.

Any pain you felt was down to not being fully relaxed and hurrying the preparation time. You've got to feel when you're ready, it's not just a matter of working up from small to ginormous. Even a tiny dick will hurt an experienced ass if it's not ready.
 
Like a lot of things, the more you do it, the more you get used to it.
Mistake using a large butt plug for your first time. You could have done some serious damage, especially without lube 😱
My wife pegs me regularly, which makes it easier each time. I love it and often cum hands free.
 
Anal is not hard. Just start slow and use plenty of lube and start with a average cock or dildo. The first time for me went really well. I was well lubed and really horny. He was gentle pushing in and god it felt so good when he got it all in. I came quicker than I would have liked but was still able to let him fuck me and ended up hard again before he finished.
 
Physically, I think it takes quite a few goes to get used to the initial penetration. Even if you prep well, it can be a bit of a jolt when he enters. With practice, you learn to relax more and open up, but it's always the worst part.

Being filled the first time didn't hurt, more a queasy, achy feeling inside. There's a dick in the wrong hole. You gotta expect it to feel weird. But there's a satisfaction you took it and you feel connected to the other person. That's never going to change.

The actual sex, well, that's a toe curling experience the first time. Again, it didn't hurt, more an ache and a churning sensation. You don't like it yet you do, and all you can think of is that slow rhythmic probing deep within. It's scary, yet you trust him. You know you've got to take it. You just don't know if you can. It's a confusing internal commotion yet weirdly pleasurable. It takes 3 or for sessions to get fully confident with the sensation and your own bodies ability to handle it. Trust me, leave getting fucked to experience assessment, first few months stick to gentle lovemaking.

As for his orgasm. You've surrendered your body largely for his pleasure, and it's clear he's getting a lot out of that final moment. You cling on to his stiff shaking body, feel his cock judder as he temporarily loses control, you grit your teeth and take it. Being cummed in is physically underwhelming, (you hardly feel the splash) but emotionally rich, it's not an ending you ever want to get used to and I don't think a dildo can ever replicate the level of shared intimacy.
 
Oh my, we have sorta the same experience. My wife is turned on by butt play and we have dabbled. I have recently been more … interested isn’t the right word, curious? (We are playing with others now and I/we want to have more of an “anything-goes” policy, so I’m curious.) She has always said that it is uncomfortable and even painful at first, but that goes away and then it’s very enjoyable for her. I bought a butt plug training set with four sizes, over a couple weeks I was able to take all but the largest size. At no time was it enjoyable, only uncomfortable and painful. One night I told her I was ready to have her play with me - back there - thinking she would use one of the butt plugs, or another small dildo we have played with in her butt. I should have been clear; unbeknownst to me she had been watching pegging porn occasionally. She took out our one strap-on, a huge 13” PVC monster, put it on, one pump of lube and tried to thrust it in my ass in one sharp move. It went nowhere and hurt like hell! That lead to a bunch of yelling and her vowing to never try to do anything with me anally again.
 
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Oh my, we have sorta the same experience. My wife is turned on by butt play and we have dabbled. I have recently been more … interested isn’t the right word, curious? (We are playing with others now and I/we want to have more of an “anything-goes” policy, so I’m curious.) She has always said that it is uncomfortable and even painful at first, but that goes away and then it’s very enjoyable for her. I bought a butt plug training set with four sizes, over a couple weeks I was able to take all but the largest size. At no time was it enjoyable, only uncomfortable and painful. One night I told her I was ready to have her play with me - back there - thinking she would use one of the butt plugs, or another small dildo we have played with in her butt. I should have been clear; unbeknownst to me she had been watching pegging porn occasionally. She took out our one strap-on, a huge 13” PVC monster, put it on, one pump of lube and tried to thrust it in my ass in one sharp move. It went nowhere and hurt like hell! That lead to a bunch of yelling and her vowing to never try to do anything with me anally again.
Sorry dude. I shouldn't have laughed, but that was funny
 
Take it from somebody who’s been pegged a few times

And I’ve had both good and bad experiences

If you know a session is coming up start with something small lots of lube

And progressively get bigger as the day goes on and leave it in

Then you can get cleaned up before the session starts

As great as it is to be pinned down and have a woman hammer you with a strap on

I’ve always found that certainly off to start. It’s better and more passionate to be on top where I can control and ride it and look in her eyes as I fuck myself with her strap on.
 
Take it from somebody who’s been pegged a few times

And I’ve had both good and bad experiences

If you know a session is coming up start with something small lots of lube

And progressively get bigger as the day goes on and leave it in

Then you can get cleaned up before the session starts

As great as it is to be pinned down and have a woman hammer you with a strap on

I’ve always found that certainly off to start. It’s better and more passionate to be on top where I can control and ride it and look in her eyes as I fuck myself with her strap on.
Just off to the pub, so I'll stick a plug up the back passage before I go 😂
 
I started playing with my butt in my teens. I kept finding more and bigger things to use on myself. Eventually I started driving and bought a dildo at the ABS. Did not take very long to learn to love anal sex. I think it was the third time I shoved something up my ass that I said, Oh now I get it, this is good mmmm so good.
Now I can take a 7 inch cock or dildo no problem, I even like it when they shove it in all at once, no easy penetration. As long as there is lube involved. I want to find a guy or trans with a big cock like 9 or 10 inch
 
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