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I remember a week before I first started expirementing with an anal toy my gf tried to massage my prostate with her finger, and I recoiled instantly and loudly proclaimed I didnt like it.
However I felt for more comfortable expirementing on my own.
So this is a unique way to introduce him to anal play. Buy a small butt plug under the premise that its for yourself. This of course does mean you have to try it, but if you dont like it who cares you only have to say that once right? and if your trying it first without shame its kind of a follow the leader mentality.
Now you leave the toy in his possesion and give him a month of the same old boring masturbation and allow his privacy and curiosity to do the rest.
Dont bring it up or ask to use it on him, or use any toys at all. Then after some time has passed bust out all your toys as if your going to have a sex party and this is your opportunity to grab the butt plug and ask him if he would like to try it.
I believe a portion of straight guys are far more afraid of people knowing they stick toys in their ass than they are of actually sticking a toy up there. Once they can act in the cover of secrecy the pleasure they will discover should destroy most of their bashfull insecurities.
Its just a weird vulnerable like act for a some straight men and team work is not always the best approach some paths simply need to be started alone.
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