As I would love to be bottomed and properly satisfied (my previous attempts were fairly disastrous) I am wondering if it's worth inserting ever increasingly large objects to stretch my opening? I have managed to insert a couple of fingers successfully so far but I'm wondering what's the largest any of you have managed to fit inside? I have heard about anal fisting but I really don't believe that's possible is it?
Have you tried working your way up? Start with dildos that are smaller than the average penis so you can get used to the stretching. Then you can keep going larger and larger each time.
Yes, that's a good way to get used to bottoming. There are even kits available that have a range of sizes. Start small and increase over time and experience. A disastrous result with anal sex is usually from attempting intercourse without proper preparation. Using lots of lube (lots and lots!), starting with digital penetration, just one finger inserted slowly, and waiting until any discomfort eases and the finger can be moved in and out with no discomfort, then work your way to two fingers until that is also done without discomfort. Penile insertion will be ready by then. Again, lots of lube! It is certainly possible, and many people enjoy the experience. This sexual act, though, carries a lot of danger and risk. If you are curious about it, I would highly recommend doing a lot research about it before even attempting it. Even then, experimenting with fisting is best done with someone very experienced at doing it.
Yes, 1, 2 then 3 fingers, smaller then larger dildos are a great way to go and, LUBE, lots of it. If 3 fingers is comfortable, then penetration should be no problem. As for fisting, yes it is possible but, that's a kink some enjoy, definitely have to work up to that one.
Well I'm OK with the fingers. Can I ask what's the biggest (ie. size wise) that anyone here has inserted? Just so I know not to be too ambitious