I have tried bottoming many times, but every time I didn't enjoy it all.
Nothing done to my back door gets me going or is enjoyable, but I still find myself desiring about bottoming.
It's not the tops' fault since I've shared a couple with friends that loved what they did to them.
Am I the only one?
Used to feel the same way until I unlocked that achievement and now I love bottoming most of the time.
My personal history here was that I'd always liked the idea of bottoming. First tried it when I was in my early 20's. Picked up some bloke at an adult theatre in town and took him back to mine. Lots of oral. Guy was pretty well hung - I was young and completely inexperienced and so went straight for the just put it in no lube or prep option and - man that hurt more than there are words for.
Fast forward to years later and was seeing a married bloke on the regular (weird situation) - he only liked topping, wasn't super hung but had a big mushroom head - still always hurt but more importantly, always felt weird/ uncomfortable/ too invasive..
Then hooked up with a fella who had made some porn, average hung with normal dimensions. In the middle of fooling around he slipped in it and it felt great - finally.
Every time I tried it after this it still felt wrong until just recently when I bought a set of trainer but plugs and started using lots of lube.
Had a guy over who was pretty well hung who took his time rimming me - then fingering a bit to relax the old twitchy sphincter - then slipped it in without warning. No immediate pain as I've had before - still felt really uncomfortable - in a weird "need to take a crap, still feels really invasive" sort of way - then it was all about just relaxing into it, getting into the right head space - taking a couple of breaks - swapping positions and now that I feel I know what to expect, how to react to it and what to do - its a whole new word.
So, in my experience, its almost now all about head space and letting that initial feeling of "what the fuck is happening to me" pass and relaxing to the point where it doesn't hurt and you can focus on what you like about it rather than the whole "somethings in my butt and it doesn't feel right" thing