Message: Girlfriend and I Want to Try Anal This Weekend
jasonxgilmore: My girlfriend is open to anal and I want to try it with we this weekend when we go stay at a cabin. Advice on how to start?
It’s best to start slowly, often with fingers, toys and lots of lube. She should have a moderately small butt plug (1 – 1.5 inch diameter) that she begins experimenting with, both during oral or vaginal sex and on her own. She should wear this for increasingly longer periods of time until it’s comfortable to keep it in for 15 to 20 minutes or more no problem.
Before attempting actual anal sex, it’s really best for her to be able to comfortably fit something the same diameter as your penis into her anus, but people do successfully go more quickly, so it’s really whatever works best for each couple. When starting out, always use lots of lube and go as slowly as you need to avoid pain on her part. At the very least, start with one finger, then add another when she’s ready, then a third.
There are many other more broad anal sex guides out there as well, including some posted on this site.