Yeah, you definitely should start with flared buttplugs. Start small and work your way up. There's some starter kits out there. (It's very important that the base is flared so you won't end up at the hospital again if it gets stuck.)
A little alcohol can help, but don't do too much because you'll want to make sure you don't ignore any serious pains. I always strongly recommend a safe word!
So my partner is 7.5 x 5.5. I had to work up to it. Once I got used to, could take it like a champ. But I really had to work on my own. Amazon has a trainer set that really worked for me. The issue I had with other plugs was that I need the diameter to remain consistent. These help so much.
I did find out recently that I am the type that needs to bottom consistently or it’s like going back to start.
Honestly, it sounds like the issue wasn’t so much your size, but a lack of communication. You and your partner should be able to openly talk about stuff that. Maybe you guys can’t make it work, but take this experience and in the future normalize talking about sex with your partner.
Look for things with large necks I used this Master Series 5 Piece Anal Trainer... https://www.amazon.com/dp/B00AU8HZC8?ref=yo_pop_ma_swf the only one that really helps is the largest the others help you work towards that if you can’t take it at first
Perhaps it's less the act and more the actor? If you're new to any sexual experience, wouldn't it be better to meet someone who is very patient and understanding to help you explore the feeling? Also, have you tried anal trainers? (https://www.amazon.com/Master-Piece-Anal-Trainer-Black/dp/B00AU8HZC8). To be honest, my anal experience has been topping or with women, but comfort is a huge factor. If your partner is not in the right frame of mind, the sex will be awful no matter what.
If I were looking to explore bottoming for someone, I would first use trainers to get confident I could take a cock comfortably and ensure I have an enema and lots of lube. However, there are millions of folks on reddit who know way more about anal than I do.
I think it is important to have a partner you trust and feel comfortable with when starting out...for any sexual act. It takes a lot of practice to get good at anything. I'd rather take a good friend in the ass and get comfortable with the experience before I move on to strangers or kinkier situations.
As other said be careful of semen dripping out into you vagina.
Now regarding the training I can only recommend this set https://www.amazon.com/Master-Piece-Anal-Trainer-Black/dp/B00AU8HZC8 it start from "how that look easy" to "that will never enter" put one after another regularly, stop at the one that is the most uncomfortable (try to keep it in 10sec). Start your session with the largest confortable size, then move to the next.
It takes time but at the end you'll the last one as a starter for your training session with bigger stuff. Also the last one is roughly the grit of a normal dick.
Use lot of lube, I use this it is cheap https://www.amazon.de/-/en/Kerbl-Vet-Slide-Slime-1000/dp/B076TCBGZM you may use this https://www.amazon.de/-/en/J-Lube-Water-Based-Lubricant-284g/dp/B00TFFEVVA You'll have litter of it or this https://www.amazon.de/-/en/Just-Glide-Anal-50ml-6239460000/dp/B00AOGB66W it numb a little bit (I would not start with this as you may damage yourself)
Good luck and have fun :D
Buttplugs are not good for anal training except for using one larger that you can fit to widen your sphincter without actually putting it in all the way.
Instead I recommend you get one like or similar to this.
https://www.ebay.com/itm/232827018132
You use it to gradually and slowly stretch your sphincter for example while touching or perhaps watching a movie. A buttplug won’t stretch your sphincter while in place and when you actually want to put something in it does not matter if you have “only” stretched the inside.
If you want to be able to take larger stuff fast invest also in a dilator kit like this one.
This will train both inside and outside and meant to be simply put in place and left there for your body to get used to it.
After stretching remember you can’t just go straight to anal sex even if putting it in now is easy. It also takes a while for your ass to get used to thrusting. Take a small dildo and start slow and go faster and if does not hurt keep increasing the size.
Take it slow since going fast and pushing to hard equals pain and often ruptures that can hurt like a bitch and keep you of anything anal for a couple of days. Using to large of a buttplug showing it in and out will get u hurt so once again stay away from buttplug when it comes to training your ass.
Plugs definitely help! I used this set https://www.amazon.com/dp/B00AU8HZC8?ref=ppx_pop_mob_ap_share
The thick necks keep you stretched, but you need a thong to make sure they don't slip out. The largest one is MASSIVE but allows my domme to peg me with her biggest strap.
Pic with tomato for scale. https://imgur.com/a/nGBoi09
I hear ya. The only dilators I've found is the set of 5 TPE plugs that are ubiquitous, EG https://www.amazon.com/gp/product/B00AU8HZC8/. NGL, I do have a set and they do the job, but I'm worried about long term use.
I'm glad you posted this, I was going to post the same question at some point soon.
I would really like to find a good set of silicone or surgical steel anal dilators. I have found some properly bodysafe dilators designed for vaginas, but they look a bit too long and don't have any 'head' to help keep them in place.
City or not, Amazon exists and I can recommend this set.
https://www.amazon.ca/dp/B00AU8HZC8/ref=cm_sw_r_cp_awdb_imm_t1_9zTuFb38JZAE8
You could get a buttplug set, or some hard plastic dilators. After a while stretching out becomes very addictive. In a good way of course.