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my boy friend and I have done this, or I should say I've done him... ;-).
I started out with a nice small sized glass dildo, it actually is the best way because it stays lubbed up for a long time ;-)
I put him on his back and I was down between his legs stroking at the same time....within a half hour he was begging for it harder and deeper....then he exploded it was so hot.
We gradually worked are way up to a strap on, but went back to manual glass didlo for the most part that is our favorite. But the strapon is good if you and he enjoy you spank'n that ass. Other than that for the feel the glass was the way to go.
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