Start with fingers and see if he likes the stimulation. If he likes it, start playing more so he learns to relax his anus. After he can do that get something in the 1.25" range made out of silicone with a curve for better prostate stimulation.

Your first stop should be a trimmed well lubed finger. Learn the come-hither motion and find his p-spot. Done during a hand-job or BJ, you should notice a huge increase in the intensity of his orgasm.

The next step for us was to use some smaller glass or metal (Njoy) toys. The smooth fitm texture makes penetration (with lube) very easy. After penetration pause to allow him to adjust to the pressure - then watching for his reactions you can begin stroking the toy in and out. This provides great p-spot stimulation for me. Starting toys in the 0.5-1" diameter range worked for me. I like the 1.25-1.5" now.

After that, there are a ton of options. Good luck and enjoy the new fun!

I can't really add anything beyond the advice already given - it's great advice! As for a first toy, I really think Pleasure Pearls is a wonderful starting point. I agree that glass or metal make a wonderful first toy because they glide and insert so perfectly with lube. Just start nice and small, and then work your way up to something larger over time. Best wishes!

Thanx! I tried the fingers and he liked it so I will look into toys that size!!Thanx again for the advice!

The three toys that got Alan started were the Tantus silk dildo (I held a bullet vibe against its base), the Protouch Plug, and the Naughty Boy. He still likes the last two.

That Sinfonia looks really nice. My hubby was given the Lelo Billy by our g/f last Xmas and loves it. And even though it hasn't got a vibe, the Tantus Silk Small makes a great introduction for male anal play, just be aware that it's a bit bendy.