My first time was sort of painful, sort of pleasurable.
It hurt for just a minute, and then there was this deep burn that felt really good. I had been prepping with a few different vibrators (3, going up in size) and even slept with a butt plug for a few nights prior to my anal cherry busting. Now, I love anal! My Filipina tgirlfriend has a nice brown 7" cock that's rock hard and just perfect!
