A taboo for many guys is anal, as in receiving. Most guys want to give it, but not as many want to get it in return. I’m not talking about guys fucking them, I mean as in a woman using a strap on on them.
A guy just tonight called and said he didn’t have a toy, but he wanted instructions on what to do with his ass. I told him a cucumber might suit his purposes. A cheaper answer than a toy to see if anal was for him. I felt ridiculous telling this man to use a vegetable on himself, but, amazingly, he made himself cum with it without even touching his cock.
He emailed a few times asking for instructions, he went out and got the requested vegetable, then called up, veggie and lube in hand and then with my guidance slowly inserted the cucumber up his ass. I had a guy call once that used a carrot, but somehow a cucumber seemed more appropriate in this case, so perhaps now he will either get an actual dildo or we can graduate up in size to progressively larger cucumbers.
Many men can cum very hard from anal toys without even touching their cock. The prostate can give them explosive orgasms that can be induced by toys, or with fingers. So if your guy is a bit shy, don’t show up sporting a strap on, suggest fingers first and then if that goes well, suggest a small toy for the next step. Your guy may never graduate to a strap on, but can find pleasure with his “man pussy”!