Not sure how to proceed...

I'm a happily married man of 16 years.my wife and I enjoy a great sex life and have always been open to each other about what we enjoy...except for one thing. I have been curious about anal for sometime now and I just haven't thought of a way to ask her. I have told her how much I love her ass (as well as the rest of her) and she responds positively. I have drifted south while going down on her and she enjoys it. Oh...and she has taken to grabbing my ass as much as I grab hers. I want to let her know I'm down for more ass play (mine to) but assure her that I'm willing to go at whatever speed she wants...if she wants. Any tips on how to proceed?

Think I'd been married to my wife for 6 or 7 years before we started. Her stance was always, no anal, even though she said she'd never tried it with a previous partner.
Think it started with us during massage. I'd just tease round there with a finger and never got stopped, obviously as she was enjoying it. Over time I just went a little further and started playing round her hole during sex, this often made her climate very quickly.
One night, she'd had a few drinks and I asked if she was up for anal sex, and she said yes. It's still a learning curve now but it takes time.

It was very much the same for us, just a little bit at a time and once the person in question realises that they actually like the feeling of Anal Play, it makes it easier to have that next step talk.

You need to discuss your fantasy with her, I would suggest both writing down somethings you are wanting to experiment, and then discussing the lists together you never know you might have some that are the same! Once you both know what each other's wants to try you can agree/ compromise or discount.

Discuss it with her we have recently gone through the same , my oh recently told me he wanted to try and its opened up a whole new sexual experience for us both , and is now something we do without even thinking about it .

And I have to say I find it a massive turn on . Thanks to lh we have purchased quite a few things to assist in making his fantasy reality .

Good ol honest communication is the key. Always so much taboo etc surrounding Anal. Yet at the same time thats what makes it so very kinky.

Talk to her openly, and sincerely. Best way to start :)

I agree, communication is the key as well as taking it slow.

Why not bring it up when relaxing together and you bring up a dicussion what things you two would like to try in sex? She can give you some ideas and you can bring the anal topic up. Maybe if she agrees, just start with one finger teasing her there, to see her reaction. Some people are not comfortable with that, but by just using finger, without pushing insde her, you should be able to judge her reaction.

If she agrees to it, then going slowly would be the way to go, slowly getting her used to the sensation as well as slowly preparing her.

I guess I am very open and when my lover asked me about anal, I told him that I do enjoy it. There was no embarassment on either part, but we were rather open.

start with prostae play maybe a finger or plug

Sounds like you have the groundwork already laid out, if you already stimulate her anus during oral and she's reacting positively to it.

You have two options, really. You can try and move things forward spontaneously, in which case I think the massage sounds like a good idea. An erotic full body massage gives you a good opportunity to gently rub and caress her anus and see how she reacts. Incorporate simultaneous clitoral and/or vaginal stimulation with your other hand/mouth, etc. This should help her to become fully relaxed as well as turned on... the best time to try something like this for the first time as a "surprise". If you think it's going the way it should be, you can then try a very slight and very gentle penetration with a finger. At this point it will become obvious if she's ready/willing or not based on her reaction.

Your other option is to just straight up talk to her about it. If what you say is true and you're happily married with a great sex life and are both open and honest about sex then it should be a straightforward conversation. Just tell her how much you enjoy going down on her and stimulating her anus, that you're curious about taking it further and seeing what other pleasures you can both give and receive by exploring it. Make it clear that you're more than willing for things to go both ways and at whatever pace she needs/wants, and I think you'll be golden.

This all looks like great advice and I thank you...but I am leaning towards talking about it with her letting the chips fall where they may. Oh...and I have done plenty of research and some 'self-exploration' of my own and I am most definitely down for receiving!

Good luck and let us know how you get on.

So I had the discussion with her last night. She said no initially. ..but has since said that she may reconsider. She wants to do some research of her own. I plan on helping her in whatever way I can...