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Because giving anal sex is my primary form of penetrative sexual expression, it became essential for me to make it easier and pleasurable for others. 

Coaching someone who is receiving anal sex is more an art than a science, but there are certain skills that are useful. You can also coach yourself while you’re receiving anal sex, something I do frequently given my experience coaching others.

Another skill I forget to mention in the episode is using one hand (or two) to hold the shaft of the insertable be it a dildo or a penis to shorten it. It’s a great way to control penetration depth on the road to full insertion. The other option if you aren’t using a penis is to use smaller insertables at first. I find the interruption of changing insertables though to be maybe too disruptive of the experience for me, so I currently prefer a bigger insertable with a hand around the base for when I want more.

There is also such a thing as too deep in my experience giving and receiving. Some recta (or rectums) are only so long. If your insertable (or penis) is too long for the butt you’re inside, it will only quote unquote “turn pleasurable” for a certain length inside before it’s just uncomfortable. That can be sexy in the context of enduring something uncomfortable for someone else as a fetish, but isn’t a best practice in my honest opinion. Ideally you want to be sized for the person you’re fucking or if you have a bio cock like I do, you can adjust their position to change the shape and length of the rectal canal. On their back with their legs up will be shorter inside than on their stomach with their legs along the floor.

Jazz Goldman returns in this session to discuss pegging as well – that is to say strap-on sex in the bum. Since we’ve both given and received anal sex with each other, we have a lot to say about the experience. Enjoy!