He entered me almost immediately after my first orgasm, it was an incredible feeling. I don't recall if he made me cum right away or if it was later. He took his assignment very serious and just pampered me the whole night. We were together for probably two or three hours and I probably had three or four orgasms that night. I wasn't really counting, but I remember just not being able to believe how much I had been missing out on up until that point.