One of my latest sessions involved deflowering an slut his ass. I already knew he was very nervous since we talked a while before he actually dared to come and see me to play. I already briefed him on how to clean and shave before the session so he came prepared.
After some talking I restrained him with his ass up so he couldn’t move but I could reach his tight little hole perfectly. Wearing a latex glove and a lot of lube I pushed one finger in, gently, and whispered “see that wasn’t so hard was it?”. One finger became 2 then 3... I could feel his prostate growing and could definitely see his cock dropping already.
So I put on my smallest strap-on, and yes he moaned and screamed. He orgasmes like a slut in the ass and not with his little dick. Just the way I like it. Can’t wait to use my bigger straps on him.