Ass o’ mine

Bisexual shaming cuts deep. Your girlfriend has treated your orientation with suspicion and disrespect, and now she wants to gain from it while potentially leaving you twisting in the wind? Mayday, mayday, mayday!

Dear Sasha,
I’m in a happy, loving and committed relationship with a man I plan on marrying. We have excellent open communication and could use your advice about how to add some anal to our sex life.

I tried talking to my doctor about it but didn’t receive any help. He made me feel like some deviant, gave me some pamphlets and told me it was unsafe and unsanitary!
 My problem is that while I enjoy the feeling of having my ass fingered or rimmed, the second he penetrates me with his penis, I’m jumping up in excruciating pain. He says it’s no big deal and that he can be perfectly happy without anal sex, but I know it’s one of his favourite acts and would like to be able to enjoy it with him.

Are there any toys, materials or methods you could recommend? And are there possible medical circumstances that would make anal impossible for certain people?

—Ass Pirate Wannabe

Dear Ass,
Many people experience anal sex this way when they first set out to include it in their private adventures. The ass evolved to expel waste, but it is also an area where you can experience a lot of pleasure if you treat it with respect and care.

There are medical reasons/circumstances why anal sex is difficult or impossible for some people, yes. For example, people who suffer from chronic hemorrhoids might find anal sex an unappealing prospect, and those with IBS (Irritable Bowel Syndrome) or Crohn’s disease may be uncomfortable fiddling around with their ass any more than they absolutely need to.

That said, one of the first things I would do is begin looking for a doctor who is more sex-positive. If your doctor believes that anal sex is primarily unsafe and unsanitary, then he probably also believes that sexual expression can only exist within outdated heterosexist parameters. He will not be a good sounding board for any other explorations you may feel like embarking on in the future.

One of the reasons people may find anal sex difficult when they first try it is because there is a lot of fear and taboo surrounding the area in which it takes place, and doctors like yours help perpetuate this idea. The anus and its corporeal allies (the digestive system, the sphincters, the anal passage) are very emotionally sensitive body parts — they react to stress almost immediately. Perhaps you’ve noticed that when you are nervous or worried, you become constipated or you get diarrhea. The anus is like a five-year-old: you know immediately when it is happy or unhappy.

One thing I have come to realize in all aspects of my life, but most particularly as it pertains to sex, is if I am doing something for someone else, specifically as a way of securing their affection, things almost always go awry. (Oddly, this is almost always made worse by a partner telling you to “do it for yourself” and not for them. Part of you always feels they are only saying this to absolve themselves of any responsibility.)

The stress you are putting on yourself to please your partner will contribute to the pain you are feeling when he penetrates you. You want so badly to do this for him. You expect to fail. Your anus clenches up in anticipation. You feel pain. And yes, that pain is excruciating, so it is certainly difficult to imagine that one day it could transform into glorious pleasure.

I encourage you to look at anal sex as something that truly has the potential to provide you with pleasure rather than as something you must learn to bear in order to please your partner. Get to know this part of your body. Read Anal Pleasure and Health by Jack Morin and The Ultimate Guide to Anal Sex for Women by Tristan Taormino. Look for instructional videos about anal sex that focus on pleasure. Work your way up to something the size of a penis, rather than going from tongue to finger to penis. Experiment on your own with a vibrator and smaller sex toys. Don’t forget to be generous with the lubricant — and, of course, with yourself.


Dear Sasha,
I am a bisexual woman, and my girlfriend is interested in seeing me have sex with men. This is a big change from the beginning of our relationship, when she was quite vocal about dating a bisexual woman and expressed a lot of fear about being “left for a guy.” I spent a lot of time explaining to her that a lesbian (or a bisexual woman for that matter) could easily leave her for another woman, that the fact that I am bisexual doesn’t mean that I can’t be faithful to the partner I choose.

I must admit I am a little worried about this change of heart. I am into group play with her, and we have visited women’s bath houses together with great mutual pleasure. It has been a bit complicated to negotiate, but always proves to be a lot of fun in the end.

My concern is that this will bring us back to a place that was uncomfortable for me and that when she sees me with a man she will begin to express feelings of inadequacy. What do you think I should do?

—Bi, Bye

Dear Bi,
You have every reason to keep a keen eye on the red flags that are flapping and fluttering around you. Bisexual shaming cuts deep. Your girlfriend has treated your orientation with suspicion and disrespect, and now she wants to gain from it while potentially leaving you twisting in the wind? Mayday, mayday, mayday!

Your inclination might be to subtly punish her with the old “but you said…” game while simultaneously forcing her to promise she won’t pull a fast one on you after the fact. You’re in the catbird seat now. Try to move past the desire to slyly gloat or at least recognize that it isn’t very helpful. I know that I might be inclined to twist a knife in just a little bit while I was considering this request. I know that people have done the same to me when my fear and judgment turned to curiosity.

I think this is something you can keep on the table to discuss and explore with caution. Your first step outside of the realm of conversation might be to attend a swingers’ event with the agreement that flirting is on the table, but full contact is only an option for a later date.

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