ownherhardxxx: i wanted to ask in the event that you’re a male who has a good female friend, and you want to go about trying anal with them, what would you say is the best way to bring it up? theres a girl i know who is as good as they get and weve been friends for a while, fucking whenever were in each others company. id love to try anal with her but im quite nervous how i should go about it.

You could always just ask if you can rub or finger her asshole during sex or oral. Or depending how close you are and how open-minded she is, you may be able to just try external rubbing (with a wet/lubricated finger) and see how she reacts. (Do not attempt any sort of anal penetration without asking first.)

If she likes it, you can go from there. I’ve talked multiple times here and on my other blog about the process of anal training to work up over a period of time to where she’s ready for you to actually penetrate her with your penis—never just shove it in and think it will work, she needs to gradually work up in size with a variety of different sized objects first.

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