What's the best way to get a guy to let me use a strap-on on him, and for him to enjoy it too!

Straight forward and up front. You would be surprised how many guys would be okay with this. But as said before, and from personal experiance giving anal to a woman, go with one finger, then two, and work it gently. When it seems like it would be okay to use the strap on, enter reaaaaaaaaaaally slowly, and leave it in for a bit before you start pumping. And always use lube. Lots of it. You can't use too much.

Also, don't forget the reach around :D

update - I've found the best way is to ASK HIM . . . I told him if he wanted anal with me; him first. To my surprise he said he would be willing. First to help relate to what it feels like to be in the position of receiver, and second because it is an enjoyable part of sharing sex. He says the small vibe we have used so far feels great on his prostate, and he has the Most intense Orgasms he has ever had. Man - Sex is soooo fun!!!!

You ask this question as if there is a way to convice him to try it. That is something that he has to be willing to try and if he is not today, then he most likely will not be tomorrow. You may want to try to use your finger on him when he is about to climax. This may excite him enough to try something else. Using a strap-on on a man is a scary thought to most, I would assume. It makes them feel vulnerable and to be honest, like they are with a guy. Try something smaller first like your finger and see if he likes it. Good luck

start slow, fingers or small vibe bullet. once ur in he'll beg for it. it feels so good, i'd pay for it right now!!!!!

Its all about being open, sit down and talk about fantasies and build up to that one!! say something like "since you always want to and do my ass I would love to bend you over and do the same to you" and you will know right away if he is up for it .... I bet when he asks you to do anal if you say no he will keep asking lol .... so just keep asking and be joking with him etc !!

As with anal sex with anyone,start slow. this might mean useing a finger for a few days or even weeks. however,if he doesnt like the finger[with alot of lube]and your starting it slow after you play with him,he might never like it.i'm not busy though!

how can i contact or call you

You've got it all figured out now. But in retrospect, the best way to approach any issue or desire sexually is to address them. Talk about everything. Don't keep sexual secrets from your lover. If you do, you may die before you can do the things you most deeply want to do. If you tell your partner all of the sexual things you want to do, they will be more comfortable and more inclined to tell you all of theirs.

<<Climbing down off of soap box>>

call me and i will let you do it--i have always wanted to try this and would want to soon