Message: Progress Towards Anal
Anonymous: My girlfriend and I have tried jumping to anal rather quickly because she wanted to try it, I had penetrated her ass a few times but she made me stop within the first few seconds but she’s determined to make it work out so she told me she wanted to try a butt plug, so I bought one and have tried it three different times we had vaginal sex and she loved it all three times, she plans on wearing it during her work shift tomorrow so I’m excited to see the progression we make in the coming weeks!
Nice, that’s great that she wants to stick with it. I definitely encourage slowing it down and working her up gradually and making sure she’s always enjoying it rather than trying to push towards having anal sex immediately. Using a plug and wearing it regularly is a great step towards that. As she gets comfortable with that more regularly, try advancing to a dildo as well. If the two of you stick with it, I’m sure you’ll both be enjoying anal sex soon.