The first thing to remember is that any kind of unwanted or unexpected anal penetration can be very painful, even traumatic for the recipient. Most people who enjoy and/or desire anal play to be fully aroused before it will actually feel good.

You could get him interested by doing a quick google search of "prostate massage." There are tons of articles by men attesting to the great pleasure they receive from a prostate massage, not to mention the health benefits. You could also try pressing into his prostate from the outside (doesn't work for some men) the next time you're going down on him to see if he likes it. To do this massage the area below his balls in a circular motion. Only proceed to the next step if he's interested.

Some tips for making it a pleasurable experience for him:
-Give him a body massage before hand, so he's nice and relaxed
-Have him bring his legs up towards his chest, this makes it easier to reach his P-spot.
-Be *very* liberal with lube & begin by lightly rubbing the outside of his anus
-Never insert anything up his ass that doesn't go in easily. He'll loosen up when he's ready for insertion.
-Enter slowly, & use very gentle strokes at first (use the "come here" motion upwards towards his penis with your finger to locate the prostate)
-Ask him a lot of questions about what feels good once you're inside of him.
-Jack him off, or have him rub himself while you're giving the massage

If he doesn't like it, or doesn't want it don't worry about it. Some men find it difficult to maintain arousal while being in such a vulnerable position. Some men simply don't enjoy the sensations. I've come across men absolutely who love it, and men who absolutely hate it. It's really just a person preference kinda thing.

Oh yeah, I was the first person to play with my boys anus, and he likes the naughty boy. I like using it on him too because I don't have to do as much work.

Thank you so much for the advise. I will keep it all in mind.

My fiancee has absolutely no interest in receiving anal from me...but I love getting anal play from her. I initiated the whole idea, and we started out with some easy play with fingers and then (quickly) I wanted more, so we started with small vibes and a butt plug and it's gone onward and upward since then.

I'd suggest exploring with your finger a little during a regular play session and see how he responds. Then ask him how he felt about it. There are plenty of small butt plugs that are totally easy to get started with. If he's receptive right off the bat go that direction, otherwise ease into it with just your hands and then work up to a toy.

I absolutely am thrilled to have play in that area, but not everybody is just like me.

There are many men who really enjoy it! I would suggest talking about it first. If this is something that really excites you, I would just mention it sometime when you are not getting sexual. See how he responds. Maybe even start off by saying something like, "I've been thinking a lot about prostate massage and it REALLY turns me on." Then you can kind of go into detail about what excites you about it, etc, etc.

If you've just been wondering whether or not he would like it, I would just open some conversation about it. After all, the prostate is like our G-Spot, so it can bring them a lot of pleasure.

The main thing to remember is to really take your time and go slow - it should never, EVER hurt. He may not even be comfortable with an entire finger inserted. You should start off by gently rubbing the area and inserting just the tip of your finger. Once he's comfortable with that, you can insert more. Once he's comfortable with more, you can insert your entire finger, etc. The idea is to work up to toys over time. Take days, weeks, months, if you have to. The end result is very worth the effort!

Always use lube and lots of it, too.

i first brought this up to my wife a couple years ago int he form of prostate massage. with some experimentation we moved up to toys, mainly becuase of her finger getting tired ;-)

there are plenty of small smooth toys for your man that might work

try the pro touch plug, its shaped like a finger

also, this shape isn't a penis. a phallic shape may be weird for a guy, so probe or figner shaped (like the pro touch) might be better suited for him, mentally

hope that helps