>>11248795Just anal masturbation feels usually awkward at first.
Try getting that knuckle or two in and then stroke your clit with the other hand.
Better yet if you tend to get very wet or have some lube handy, you can try to master the clenching and release of your butthole to achieve optimal pleasure when you feel like it.
Then, when you're getting used to fingering your ass while you rub one out, do it during sex.
You'll come tsunamis, you'll get the message across, you won't have said a word and you'll be physically ready to take him in if he wants to.
Remember that some men are really dumb and can't take a hint. He may have thought you were joking. He may have thought you were forcing yourself to sound cool, he may have though any number of things that got him the wrong answer.
So if you're shy, it's okay. Just get to know your body on the side and show your work.