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.
 
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