Best Way To Loosen a Tight Ass?

I'm a gay man, but I guess this could apply to a woman too. I've mostly been a top but have been getting in the mood to bottom more lately. Problem is because i've rarely bottomed I have a really tight ass. Are there any recommendations as far as fucking methods anyone can recommend to make bottoming for me more comfortable? I have found taking it from behind or riding on top first seems easier. Anything else?

Play with you ass in the shower when things are all slippery and relaxed....1,2,3 fingers up your butt, finger fuck yourself......I can spend hours in the shower workin my ass.....

Another idea and the one I used is to get a bunch of ass toys of increasing sizes. When you're getting used to the small one, move up to the next, and so on. It worked great for me.

I was going to suggest "Johnny Cash Chilli"
Good dosage of halbanero, jalapeno peppers, the usual beans, beef (rancid's OK, here...), onions, spices... a good doseage of laxatives... Loosen ya right up. and... gives you the Ring of Fire...


Oh, wait... that's used to stop thefts of lunches at work.... my mistake...

I like this idea, I volunteer for it to help you out!

give yourself a good clear out before hand, while your doing that use a dildo or butt plug - or even just your fingers and just gradually build yourself up to it.

Obviously plenty of lube helps aswell! lol

Gradually building yourself up with different sized toys - you can take up to all sorts of sizes.

....I've managed to use a dildo with a 10" circumference!