I use some of mine almost daily.
The largest plug I have is 3.3 inches in diameter (833mm)
It took a lot of practice to work up to that size, but when I finally managed it, it did hurt quite a lot, and it hurt as well getting it back out past the widest part.
I eventually got used to it, even though it still hurt getting it passed the widest part.
It holds itself in really well, and I have been to the local shops with it inside a few times.
I have even gone to sleep at night with it inside.
I really only use that when I'm extremely horny, and my usual day to day plug, is a prostate massaging plug that I wear all day.
I do have a 14 inch long steel dildo with a 50mm wide head that I use now and then..I can just get 12 inches inside before it cums to a stop.
It was bought for my wife originally, but one night, I let her try it on me..
I told her to take it very slowly and carefully.
She lubed up both my butt hole and the dildo, and started pressing..It would only go in so far.
She decided a good hard push might work, and the neighbours must have heard my scream.
I had never felt such pain, but she laughed and said at least its inside now.

I will use my toys when the opportunity presents itself. I usually start off with my double headed,12" long dildo. I can get it all the way in so that just the head at the other end is sticking out. I then lube up my 6" penis shaped butt plug and slide that in next to the double dildo. I like to rock back and forth while sitting on my office chair with both toys in me at the same time. I've had my double dildo slip completely into my boipussy once. That scared me a little but at the same time, excited me as well.

I am much more of a top, so I do not do much ass play on myself. My anus is quite tight, and any insertion is uncomfortable. This week, I brought home a small and rather thin dildo and gave it another try. I was able to get it inside my anus but was unable to really enjoy it. I envy you.

Happy to report that on Sunday I was able to take at least eight inches ( +/- 20.5mm) of a beer bottle inside my sissy pussy. The bottle is 2 3/8" circumference ( 6 mm) and it went in quite easily. Of course i used plenty of Crisco lube and took my time. No matter what brand since all bottles are basically the same. So proud. A real accomplishment for me.. Will probably do it on chat video just to show off.

Happy to report that on Sunday I was able to take at least eight inches ( +/- 20.5mm) of a beer bottle inside my sissy pussy. The bottle is 2 3/8" circumference ( 6 mm) and it went in quite easily. Of course i used plenty of Crisco lube and took my time. No matter what brand since all bottles are basically the same. So proud. A real accomplishment for me.. Will probably do it on chat video just to show off.

I use it almost everyday. Do not know how harmful it is for my ass but I enjoy dildoes so much. Every time I use it I know that this time I'll be happy anyway. So I cannot stop using them when I have a free time

For me the best toy is my raccoon butt plug. I started small but gradually got bigger thicker toys. Actually fucking my self with it makes the masturbation wonders. A big surprise it was but now I an hooked. https://www.lovexxo.com/collections/raccoon-tail-butt-plugs

I don't own a butt plug, I'm scared in case my Mrs finds it. I use my wife's toys, obviously when she's not around lol. I can only manage the skinny vibrators sadly.

My biggest to date is now 3 3/4 Inch diameter ! Its a struggle to get it in but a few times in and out loosens thing up good ! I just set it on a stool and sit down on it ! Takes a few minutes and some weight on it to stretch my sphincter enough to let it pop in ! Hoping to work my way up to 4 inch !

My biggest to date is 3.75 inches diameter at the widest ! Takes a while to work up to it but about a half an hour and it will pop in !

I can only handle small dildos. It's too painful if I try anything but the most slender. I wish others would explain exactly how you move up a to a larger one. I need coaching lol. Anyway I wish I could handle a big one and that it would stay in so I could go out with it. My goal is to take a big cock some day. That would be transformative.

I have a fairly extensive toy collection that consists of numerous dildos, leather restraints, ball gags, floggers, a riding crop, lots of rope, two homemade spreader bars, several cock cages, two inflatable butt plugs, a Hitachi Magic Wand, and a fucking machine. Yes, I'm very much into BDSM!!! I have an extremely large dildo that is thirteen inches long and three inches in diameter that took forever to work up to and even then it hurt like hell, but OMG what intense assgasms it produces! That's where the inflatable butt plugs come in handy for training. Also, I would point out that the kind of lube you use (and lots of it), is really important. My personal favorite is Xesso water-based (it's unscented; looks and feels like real cum, and last forever for extended play periods. That said, my favorite dildos are a horse dildo (11 inches by 1-3/4 inches), a six-inch G-Spot vibrator, and the one I call the purple monster (a realistic 9 inches long with a nice curve and all sorts of wonderful ridges with 10 vibration speeds and patterns and it's also waterproof that make taking a bath a hell of a good time! I also have a Lovense Lush 2 for on-the-go fun in the car, the grocery store, or lingerie shopping.

not often enough, apparently. today I only got about an inch and a half of my 6" dildo up my ass. it's barely an inch in diameter and I used lots of KY but it still wouldn't go (but it felt good enough to get me to cum once)
so clearly, I need to get back to sitting on it 2-3 times a week.

It has goten to the point i find it very hard to cum unless i have a toy in my ass normlay i like a long thinner plug but at times want somethign thick to strech me and as i bounce on it i cum so much harder then normal

I currently have 5 plugs and 2 dildos. Over the years I have had many, many toys of all sizes. I love having something in me all the time.

I kind of go in spurts. Currently I'm working my hole every day with my dildos or plugs. It's mainly because I've found a few cocks that use me regularly.

I love the feel of a nice butt plug going in slowly and coming out but my problem is it keeps coming back out if I want to wear it all the time. Any suggestions how to keep it in? Also I guess it don't sound much but I'm in an inch and three quarters and one to get bigger but my tight ass won't allow. What's the best way to really enlarge your hole slowly to get maybe two inch or two and a half inch? Thanks sorry about all the questions

A couple suggestions. Look for a plug with a thin neck. The more you can get your rectum to close, the better it will stay in. I have also used a snug fitting thong to help hold it.

As far as stretching your hole. Try to find a tapered dildo and use it frequently. The more you use it and the deeper you get it inthe more you will stretch. Of course, there are limits to how much one will stretch.

I don't have a problem with stretching enough, but my bone structure back there seems to limit the size I can take. I've seen guys using huge items and I just can't get anything over about 2" to 2 1/4", and then it needs to be squishable. No bottles, cans or ball bats for me, unfortunately. Hope this helps

I use my 8" dildo nearly every day

I've recently started using tapered training hoses that come in a variety of sizes. I also like to use a larger plug that opens me up a little more and it has a hole going thru it. I have to use lots of lube but when I get the plug in, I then take the larger tapered hose that measures 19 1/2" long and slide it thru the plug , into myself. It a wonderful feeling having that tapered hose sliding in and out of me. Some of the best organs I've ever had. Now I just need to find someone to play with me!