I don't know. I've tried numerous times. I've had butt plugs, dildos with lube and attempted it when inebriated, sober and once with muscle relaxers. I can't ever seal the deal. I guess my booty is too tight. Originally Posted by Allie_KatI have schooled a few in the pleasure of this and by far the best way is to be on your back, not knee's. Slow, slow, slow, breathe, relax, breathe, relax use a vibe on your clit. I could show you in person and would give you a $200 an hour discount for being an eccie member!