Hopefully it is clear that you should ask and communicate. 😀
With a little lubricant it is definitely easier and more fun. If I do it myself while jerking off, then the finger goes in quite well without lubricant, but if the woman does it, please do so with a little moisture.
Playing at the hole is also very exciting and you don’t always have to push something in.
Just ask first 🙂 don’t go all “no one expects the Spanish inquisition!”
Issue I’ve run into is partners don’t realize they need lube to do that. Spit kinda works but not really.
You can even just play with the hole and not put anything in and it’ll feel nice.
Hopefully it is clear that you should ask and communicate. 😀 With a little lubricant it is definitely easier and more fun. If I do it myself while jerking off, then the finger goes in quite well without lubricant, but if the woman does it, please do so with a little moisture. Playing at the hole is also very exciting and you don’t always have to push something in.
I have other things I can push in for you too, big guy 😉
I’m sure you have other things for that 😬