Other helpful discussions on Prostate massagers:

Spotlight on the We-Vibe 3 (and a giveaway)!
The We-Vibe 2 has become one of the more popular couple's toys out there, and for a good reason! It can easily stimulate multiple areas at once!...

Guys, what does your partner use?
What does your partner use to for anal play.

Ever heard of the A-spot?
I've come across this in a couple things I've read and while initially skeptical, I think it exists and I think I've actually been stimulating it more...

LOST!
I have started exploring & cannot seem to locate what I have been defines as my prostate... I know it's gotts be there cause I can stop peeing, LOL....

Have you massaged your prostate?
Just curious to see how many men do it. Keep in mind it doesn't make you gay.

I'm a big fan of Maximus water based lube for almost everything.

It's not a matter of enhancement, it's like a different kind of orgasm. I think the best relation could be a clit orgasm vs. a g-spot orgasm.

Maybe just start with your finger during your normal play/foreplay and then suggest a toy after that. Some (maybe a lot) of guys are intimidated by the idea at first, but probably will be more open-minded when they figure out how pleasurable anal play can be.

I have tried to talk my man into external anal stimulation, alone, and this is a no no. In all the years we have been together I have never seen his hole or touched it.

I think it is because he is very self conscious of this area of his body.

I have talked to him about it and tried to go there smoothly with my hands but I have never touched it because I respect him too much to go against his wishes.

I think that nagging and constant mention of wanting to do something might become annoying and be a deterent. I think that in my personal experience my man will have to come forward and ask for it when he is ready.

He is open to some play but I was just wondering what toys or lubes are good for this.

I'll second JR on using Maximus...it's the best, most comfortable and non-irritating lube we've found for anal on my partner. Right now we mostly use the TitanMen Master Tool and a glass prostate massager I couldn't find on this site. But neither of them are for beginners at all. You'll want to start with something smaller and not-so-rigid. And anything in silicone is great because it can truly be sanitized after use.

Maximus is good but it can be a problem if he has chemical sensitivity - then it burns. I use Probe Thick and Rich, and I've heard from others with chemical sensitivity that it seems to be pretty neutral. It's not quite as thick as Maximus and it's a bit stringy (takes some getting used to), but it works well.

Choose something small and non-realistic to start. Bootie, Little Flirt, Slim Pleasure #1, Buddy and Encore would be good plug choices, since they're small and can be used for both static put-it-in-and-leave-it play as well as for some thrusting.

A toy such as the Tantus G-Force can also be fun. It's small and not too threatening, and it can be used by both you and him anally or vaginally (it's silicone so you can disinfect it).

A small smooth dildo could also be used. I wouldn't recommend a prostate massager unless he expresses an interest, since they're more special-purpose and some men find that they don't work on them.

Start with the finger, definitely, and start outside. For everyone I've discussed it with anal/prostate play does change the orgasm, but it's different so you might need to try it out several times as a couple for him to start to appreciate it.

Don't worry - he'll still like other sex play as well.

to answer your last question, yes, i cum huge after anal penetration and massage, huge

Blush and tell him you want to buy a butt plug or two to try yourself. Have him pick some out with you. When they arrive make an evening out of it. Take a bath, Out to dinner, drink some wine, come home, have him put one in you and have sex with it in, than tell him you should both have one in to have sex with, make sure lights are dim, and its all down hill from there.. Thats what happened to me atleast.

We like to use Climax Bursts Anal lube for me, we've yet to experiment anally on him. I've heard a lot of good about Maximus as well.

There's no way to really "talk him into it". Some men are just not open to this. Period. Nor will they ever be. It doesn't make them bad or homophobic. It's just preconceived notions of "that's a no-no".

My man could care less about his P spot. He just doesn't want anything up his butt, and like NaughtyStudent said, I respect his wishes and will NEVER nag him or beg him to do something he isn't comfortable with. No one wants to feel like they're being pressured into a sexual act.

Start with a finger, if he's game go from there.

My suggestion for any woman to get a man open to trying this experience is work into it slowly. Try many situations with external stimulation in the perineal and anal regions. There is so much enjoyment down there that he will eventually open up to the "SURPRISE" slip-in of the pinky finger. (No long nails, please). Once he has the experience then work from there. I think many men have an emotional barrier of having enjoyment in "that" area until they realize the wonderful feelings they can have other than their usual "slam-bam thank you mam" past experiences.

Lead by example is a good start too!

For the "I'm not gay talk": try to reassure him telling everything he does with a woman can't be gay, because he's doing it with a woman.
For the rest, I don't know. Some older generation men have been traumatized as children by suppositories and will be left with major problems in accepting any pleasure from that area. Follow his rythm, it's his anus, afterall.

Desensitizing anal lube is great. Try to avoid glycerin-based lube, they hurt like fuck because they tend to burn when they rub. Also, flavored lubes (if you can stand the glycerin they're packed with) cover the embarassing smells that could irradiate form your love-making.
Good luck.