Helping him relax...
 

My boyfriend and I have been experimenting a bit with tantric massage and we've decided to try stimulating his prostate through his anus. Has anyone here tried this before? Any tips on making him more comfortable and helping him relax? This is the first time we've played with the proverbial back door, and I'd like to make sure it's a pleasurable experience for both of us. Many spanks! ;)

Tell him its great. he has no need to worry.

The first time i ever tried it i was in the bath with my girlfriend and she did it to me while wanking me. i shot straight away!!

As much as my man hates anything in his anus, I can usually get a finger or two in there while I am giving him a nice long blow job.

Then he don't notice the fingers as much...:D ;)
He is too busy concentrating on how good the blow job feels! :D :p

I'm usually more comfortable on my back... and make sure he's turned on and well lubed. For me, the closer I get to cumming the easier it is to put things in my backdoor. Go with Diva's suggestion... start licking and sucking his cock, then start to ease a finger into him. Sounds like he's willing so he'll probably enjoy it. Good luck.

3 words - "American Pie 2" :p

lol
 

Haha, Legend, we've actually not seen the movie- I've heard it's pretty funny... Everyone else, thanks for your advice, I'll be sure to use it

there's a part in the movie about "stimulating the prostate". if u watch it you'll know what i mean :)