Another thing that could help (like others have mentioned) is using smaller toys.
But with a twist. Most anal enthusiasts have a small plug they lube up and put in in the shower.
The bigger the end goal toy, the more “stepped up little toys,” they do this with until they are not only pre stretched but pre-lubed as well.
This is what I do, and it always puts my mind at ease because I know that there is no “uhoh what if it’s gross factor,” and to worry about as well. That’s always my biggest fear.
Some other tips that might help. And also might sound counterintuitive. When you’re being entered don’t tighten at all.
The more you tighten the more it will hurt. This may sound gross but it’s a visual you’ll understand when you read it.
If you “push” like you’re using the bathroom (lightly, not with all your effort ), it’ll actually make your anus not only relaxed, but “opened.”
As many others have said it’s an inch at a time process or it’ll hurt. Unless you’re pre-stretched and pre-lubed.
Just know that the deeper/bigger you go, the slower you need to go until it’s totally comfortable. Too fast too big too hard will always equal pain. Pain is not what you’re supposed to feel.
If you feel pain, slow down, take time to acclimate (and you literally can acclimate to any “size” but not all “depths.”)
Maybe do some Reddit research with videos to see the outrageously huge long things people can put inside themselves at the same time.
It’ll blow your mind. There’s one German Woman who’s pretty much the undisputed size queen. To the point it’s gross. But. Let’s just say we are talking baby sized (and shaped), dildos with cantaloupe sized sex toys as well as more than one of each at a time that she pops out. Like I said it’s gross, but it proves my point that there is no limit I once you’ve broken certain anatomical barriers.
There’s one guy that’s equally famous that I’ve talked to, he daily takes 22-30” plus sized “horse dildos.” I asked him how he got to that point and he said with a lot of practice. And that quote “He’s pretty sure if an x-ray was ever taken of his intestines it would be a straight line to his stomach.”
This is obviously an exaggeration he’s stated, but a funny one, nonetheless. As the small intestine is almost 2 feet long and the large intestines are around 5 feet long. But I still don’t understand how he’s managed to navigate all those internal twists and turns to just slip them right in with little to no effort. And neither does he other than lots of practice. And very long flexible skinny anal toys to “lay the groundwork,” to taking bigger longer harder toys.
If you’re having sharp pains no matter how much preparation you do in advance you could have certain medical issues internally that you might want to get checked.
If it’s short into the entry point, you may have hemorrhoids. If you do you’ll normally see bright red spotting.
If it’s dark black (like dried blood, or a sticky tar like residue), it could be a few different things. And those I would advise you to be checked by a doctor for sooner rather than later. Polyps. Fissures. Tears. And even cysts can be lining your anal canal that are all not normally there and should be checked.
If there’s no blood, then it’s probably just a case of taking it much slower/with more pregame preparation, and the more foreplay you get the better off you are.
Just like with Vaginal penetration, only the inexperienced go “straight for the goal.” So. Have your partner “Play, tickle, kiss, and tease you first,” and this will also relax you a lot. The general colloquialism is, if it’s winking at you, it’s ready for more than just foreplay.
The anus has a whole lot of nerve endings in it that most people never feel the wonder of. You’ll see that it’s incredibly pleasing with no penetration if your partner tickles, rims, touches, kisses etc. After all that has been done you’ll probably be like most people and actually desirous of being penetrated.
Generally speaking the side spoon position is best so that you are in control of the speed depth force etc rather than the penetrator as they simply aren’t able to feel what you are inside your own body.
I hope some of this helps you.
And the last word of advice I can give you that may be the single most helpful. Play with a toy by yourself in the shower so you not only learn what it’s supposed to feel like. But what you actually like as well.
Every one is different. If you find out your “style,” by yourself when you’re in complete control. You’ll be able to direct your partner to giving you what you like, while they get what they want at the same time.
And that eases the apprehension of vulnerability of neither knowing, nor being in control of the vulnerable environment you may be feeling you’re in during these conversations.
In my experience, it’s as much mindset comfort level as it is physical comfort level that matters. This is definitely a good way to remove the mindset “discomfort,” level and give you the confidence to enjoy the experience with your partner.
Hope some of this has helped. Don’t give up on it. There’s all kinds of amazing things that can “come” as a result of a willingness to explore this part of your body that you’re completely not expecting.