If it doesn't feel good, don't do that! I've only ever done it with my husband, and we'd been married a few years before we tried. It's best if the woman can directly do the pushing. Not for anyone for any reason. If he has a small penis, deep penetration might be fine, but if he has one on the bigger side, he might only get halfway in before it starts to hurt, and that's fine. I told him we'd try and if it hurt, I'd tell him to stop. Via Getty Anna Breslaw Writer.
Kyleigh. Age: 32.
So make sure you're really turned on beforehand and that you're not just doing it for your boyfriend.
Zaria. Age: 30.
How This 39-Year-Old Mom Has Orgasms From Anal Sex
Especially when you're a parent, anal requires good luck, good health no tummy troubles , and good timing. I can definitely orgasm with only anal penetration, but sometimes I get the double orgasm when we add in clit stimulation. Because really, does he want to get a little piece of shit in his urethra?