If at first you don’t love anal, give it a second chance. If you’re brand new to anal play, I strongly suggest playing with a butt plug prior penetrative anal intercourse with a penis or strap-on dildo. (You can do that by yourself or with a partner.) It will get you used to the feeling of being “stuffed,” in addition to assist loosen up the sphincter. “This is a good position for couples who are new to anal sex,” says Margo. Lie on your sides, with you on the within and your partner curled round you spoon-style. As you play little spoon, your partner can slowly ease inside you inch by inch.