
Dear RLL,
I have always wanted to try anal but I am afraid to bring it up with the wife. How can I find out if she likes it without freaking her out?
Wildly Shy
Dear WS,
I’m so glad you asked! Anal is awesome, and it still has a reputation to contend with, so anything I can do to open the doors, so to speak, is my pleasure.
If you feel like you can’t bring it up in conversation outside the bedroom, which is the least pressure way to broach new sexual subjects for the most part, then I would suggest playfully approaching the back door and asking politely if you may perhaps inquire as to whether or not it is acceptable to ring the doorbell.
By this I mean you are not to ask for anal sex, in word or gesture. What you are asking is if that concept is open for discussion. So insertion of anything into anywhere is off the table for the moment. Think stroking, teasing, playing. Treat her little starfish like a nipple. Wet your finger and rub it a little, see how that goes. If you are feeling really adventurous try taking a trip south when you are going down on her, licking lower and lower and see if she stops you. This can also be really fun to try in the shower.
The taboo is strong, but it also makes it really hot. Go slow, use lots of lube and if it hurts you are doing it wrong. Depending on how you interface physically anal sex may never happen for you, but you can still have a lot of fun. Let her play with you a little bit, see how that feels. Show each other what you like. This could be a whole new world for you two, but don’t be disappointed if it doesn’t work out right away.
One option if you are just too big for her to take is to put a harness and strap on over your pants and do her with a tiny dildo. No, it’s not the same, but boy it is still fun! Take your time, relax, read up on the topic together, watch videos (Tristan Taormino is the best) and explore. You may have grown up thinking a butt plug was hilarious but if you try one out you might not be laughing. Turns out they kind of rock.
Have a question? Send it here! ducttapediva@regynalonglank.com
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