first ass play

My GF trained me

Well, actually I used to finger myself, used different objects from tiny to larger, enjoyed all.
One day my GF slid her finger in me which I loved. The next GF started fisting me that I loved a lot.
Another one used a very large dildo. That was a bit hard. It was possibly more than 12 inches and very thick. She did it but took long time to plow in to me.
Try things as you progress try thicker and longer toys
 
Start off slow

Gentle is the first thing that comes to mind when playing with a virgin ass. Play with your partners cheeks, rubbing and caressing then stroking gently. Sometimes I put myself in the 69 position with me on the bottom. That generally places my nose close to my partners asshole (not trying to be crude but let's call a spade a spade!). After some fun sex play (i.e. with a man sucking his cock or licking/sucking his balls for awhile - with a woman burying my tongue in her pussy and licking with my tongue/lips) I'll move my tongue to his/her asshole and gently kiss and tongue relaxing my partner. One can tell if your partner is not going to enjoy inserting your finger(s) in their ass if they don't enjoy your tongue. If they are enjoying your tongue they will typically (hopefully!) reciprocate and begin tonguing your asshole. Have some lube on hand and move into a position where you can caress your partners ass and gently insert a "lubed" finger. I have found that once my partner is pretty "horned up" (whether fucking them or eating them) it is a good time to insert my finger(s) into their ass fucking their ass slowly and then matching their movement. If successful, their climax should be even greater than what may be typical - especially if this is the first time with anal play. Gotta go, this is getting me horny and I need a release!!!
 
Slow, gentle, and lots of lube!

If you use a toy or makeshift toy, keep it smaller than your normal bowel movement and there will be no pain. Make sure that all toys are unbreakable, smooth, and without sharp edges. Wash and sanitize all toys before and after play. And finally, keep all anal toys separate from vaginal toys, you don't want cross contamination.
 
I started with a pen. Graduated eventually to my wife's dildo.
It is good. Very good...
 
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