Dear Jane: My BF Wants Anal; He Even Said I Can Do It to Him, What Should I Do?

Dear Jane, <— if you click this, it’ll take you to Formspring.me.  You’ll be able to ask me whatever you want, and be totally anonymous.  Do it, and do it often; please and thank you!

My boyfriend really wants to do anal, and really wants me to do it to him too. I’m willing to finger/use anal plug/peg, but i think he wants to do it to me first and i’m not exactly comfortable with that. What should i do?

Featured: The Nexus Glide

There a term in the BDSM lifestyle called “Old Guard”.  It is when a true submissive spends time being a Dominant so that they can better understand submission and Power Exchange.  In the long run, it makes them a better submissive and person in the end.  Some people remain a Switch which is fine; it is a learning experience after all. This opportunity also rarely happens in its true form, the term also tends to be archaic.  But, ya know what I think? Carpe diem.

If the occasion arises that you are able to turn the tables like that, do not say you wont try it please. I strongly suggest you try it (thrice).

Tell him you’ll do it, after you do it to him.  He can help guide you, and you can learn how it is done… all the while showing him what anal is supposed to be like.  Tell him to prepare, because it’ll be a night he wont forget.

Use oral sex, analingus, use lube, go slow, relax… make it sexy and fun.  Tease, rub, and fondle.  Use your fingers, start with a small anal plug toy… go slow… and go from there.  Ease it into him a micrometer at a time, allow his body to get used to the intrusion, let his body swallow it and adjust.  Rub his legs, balls, cock. Pat the toy a bit once it is in.  Usually men find the feeling of wiggling or tapping the toy much more than the “in out” feeling.  If you find an angeled toy, aim it for his prostate… his cock might drool, he might even come immediately.

Plus, after you get over being nervous, penetrating a man, is quite a power trip.  If you do it, you’ll understand what I’m saying.  Men are usually the penetrators in straight relationships, women are the receivers – to turn that table. Wow.

If you do it right, he’ll love it, and feel no pain… and hopefully LEARN how to do it the right way from you.  This way, you don’t have a terrible experience.

PS. It doesn’t make him gay.

He also might be willing to let you stick something in his ass, because he wants yours so bad.  If he has never done it and wants to, he’ll say anything to get it. Be careful though, (as I say this, I’m laughing lightly because it has happened to many people I know) you could end up liking it and he might lose interest… then you’re really stuck. Oh no!

I wish you luck with both your anal experience(s), and I hope you both enjoy it.