My first husband wanted anal sex, so we tried it, and it hurt so much I said never again. That was 20 years ago. Now I’m widowed and in a new relationship and my new man is asking about anal. I told him what happened last time, how I tried it and swore off it. He’s 61 and says he can’t get hard enough for anal intercourse and just wants to finger me. I want to please him, but I’m phobic about any anal. Help!
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If you don’t want to do anything anal, you’re under no obligation to. No one should ever feel pressured or coerced into being sexual in ways that turn them off.
That said, there’s a big difference between penis-anus intercourse and other types of anal play. From your description, I’m guessing that your first husband just pushed himself into you. Even with lots of lubricant, that can hurt. However, the anus is sexually sensitive and many people find gentle sphincter massage or fingering very erotic. Among couples who engage in anal play, penis-anus intercourse is the least popular variation. Most lovers confine themselves to sphincter massage or fingering.
My suggestions: First decide if you’re open to any anal play. If so, then you need to learn a little about you anal anatomy. Few people know that we actually have two anal sphincters, the visible one, and another ring of muscle about an inch inside. The outer sphincter is easier to relax, but with time, patience, and gentle, well-lubricated play controlled by you, the recipient, the inner sphincter may also relax enough to allow enjoyable fingering through it.
Initially, explore your anus by yourself in the shower. Use lots of soap as a lubricant. First, gently massage your outer sphincter. If that feels enjoyable, then gently insert one finger until you encounter your inner sphincter. You don’t have to go any further. But if you’d like to, then very gently press your finger against your inner sphincter, and if that feels okay, you might slip your finger through it. Or not, it’s up to you. If you’re into experimenting with anal, finger yourself repeatedly over several weeks to get used to how it feels. You might also keep your lover updated on what you’re doing and how it feels. I bet he’ll be very interested.
If you decide you’re open to anal play with your new lover, insist that you be in control of it. Ask him initially to limit things to gentle caressing of your anus with a well-lubricated finger. If that feels okay, then invite him to insert a well-lubricated finger through your outer sphincter, but not the inner one. That means that he would insert his fingertip, nothing more. Over time, if that feels okay and you want to take the next step, position yourself on your hands and knees, invite him to finger your outer sphincter, and then tell him to stop. Then you move yourself back onto his finger. You should be in control of any play with your inner sphincter. After a while, if that feels, okay, then you might invite him to finger your through both sphincters.
For more on anal play, including hygiene issues, read the chapter, ‘Anal Play Without Pain” in my book, Sizzling Sex for Life.