How to help my man feel comfortable with anal play

Just don't push it too much... Some guys (including mine) are just not into the idea of anal play, just like some girls aren't.

Massaging his prostate with your finger while giving him a good BJ is a great way to expose him to the intense pleasure that's available to him. Caution - if this works as I suspect - he really will explode - so be ready!

At some point maybe 2 fingers get into the action.

Since my wife has small well manicured nails - finger is OK, but I really prefer when she uses one of our glass toys with silicone lube. My favorites are Lucid Heart link, 4-way cyberglass link and the Silenzio link. The 4-way is a good starting toy, then the Lucid Heart, then the Silenzio - it's my max right now - but I may go larger some day.

I would say go about the idea slowly. Starting right off with a butt plug, according to what you said, may freak him out a bit. Gunsmoke's suggestion was great! Start with finger play during sex, rubbing around his prostate and anus. Take one slow step at a time. The toy may make him feel pressured into doing something he's not comfortable with at the start. Communication is key! Have you told him your fantasy? Maybe if you discuss it together in an exploratory way and have fun with it he may be more open to a slow experimental start. Good Luck!

If/when he play with your anus moan extra load informing him how much you enjoy it. Then when giving him a bj with lubed fingers play with his anus, probably not going in the 1st time unless he wants it. Probably best to do it when he is close to cumming. Or the same while you are riding him in the cowgirl position.

I was in the same boat as you are in exactly! I just kept playing and rubbing his taint every time I would give oral or a hand job. He really liked it, but never really expressed any want for anal.
I suggest kind of planting a little seed in his mind about it, like I heard that men's bums are much more sensitive than women's are and how amazing it already feels to a girl how much better could he feel?. Along with that seed I would get a new plug for 'yourself'(I got my husband a bootie butt plug in black) then 'misplaced' in the bathroom, where he could find it and figure out for himself without judgement or pressure from me.

Basically,educate him about the wonders from your view point. Let him link up whether he really wants to or not. If your guy is like mine he will never ask for it out right, so lay out the bread crumbs and when he picks them up be there to take care of business.
Hope this works out for you and your partner and he comes around(no pun intended), but ultimately if he is doing you a favor by taking a finger for you he won't enjoy it and you won't either, so be willing to accept his ultimate limit.

Gunsmoke has it pretty good. If/when you get to two fingers, break out a 4" pocket rocket some time. once he's letting you use vibrators and getting into it, he'll be ready to consider much more because he's passed a boundery line.

If you aren't doing it already, a little sexual bribery wouldn't hurt in your cause either. Man get more willing if the woman is "Well if you just try this for me, I'll let you _____.(whatever you know he loves the most in the world)" And when you let him do whatever it is, make sure you put full effort into it and show him how hot you got because he let you work his butt. That will increase your chances of him considering it again with more ease the next time around.

Just a suggestion.

i would probably go the blowjob/well-lubed-fin ger route to start off. seems the butt plug is more about the fullness feeling unless it vibrates, which is great. its really about finding and fingering hit prostate and introducing the finger after you have got him really hard and 3/4 of the way there. getting past the psychological part is the harder part. he might like it but feel embarrassed to say so...

i love it, i am on the opposite side of this conversation than you are im trying to talk my wife into anal with her including toys. i have only gotten as far as fingering her when she is on top about to cum and she has allowed me on a FEW SPECIAL occasions [birthday, anniversary first time as a total surprise] to have anal sex.

good luck with it!

Everyone is different of course, but what worked for me/us was:

1) Verbal persistence. I told him how much it would turn me on for him to try it on me and then once I got him there, I told him how much it would turn me on for me to be able to try things with him.

2) Taking it SLOW. It took years before he'd try it with me and another few before he'd consider it. But now he's warmed up. He'd never suggest it, but if I do, he's open to it now. THANK GOD!

3) Not spending too much time right at the opening. It was serendipity really, he was saying that he had some discomfort with a very, very small butt plug and I sneezed when it was just a 1/2 in or so in and it went all the way in and he immediately breathed out and said it felt so much better now that I was past the sphincter! So now we don't waste time at the door, but just go on in once he is lubed up! Try the shooters to get lube in there first, too!

4) I've learned to not focus on his phenomenal ass too much. I will get a butt plug in and leave it and focus on a blow job or letting him play with my tits while I mount him from above and thrust against him without any harness or dildo present and sort of mimic it, but with it stable in his butt. Then we move on to the harness/dildo or sometimes just the dildo.

5) I buy small, slender toys for him and larger ones for me. I find that he's comparitive and mentally things it is okay because while he might normally thing something is 'huge' for his ass, when he sees it in comparison to what I use, he thinks of it as small and easy.

6) Before, during and after I always am sure to tell him how hot it makes me for him both to recieve and to give and that helps...a LOT!

Good luck!!