Pleasure Activist

Hey, it’s still anal pleasure month!

Last week we left off in the middle of an interview with sexuality educator, Jessy Schmidt. In honor of Anal Pleasure Month, she will be facilitating a discussion-based workshop about anal sex this Sunday, August 16 from 6:30-8 p.m. at Jellywink Boutique, and you can reserve your spot on Eventbrite.

Schmidt’s particular angle is pegging and so we’ll continue where we left off:

Ally: I remember reading that companies who manufacturer strap-on sex supplies get most of their business from heterosexual couples. That’s why I find it ironic when people refer to strap-on harnesses and double dildos as “lesbian” toys.  What advice do you have for guys who want their girlfriends or wives to peg them, but are worried about how to bring it up?

Jessy: Many folks still think men who want to be penetrated must be gay or will become so. Like there’s a magic butt button that turns on a gene somehow. It’s understandable why some would be worried about bringing it up. Activities men do with female partners do not make them gay. Actually, as a ‘gay’ activity, anal intercourse comes in third as the most popular activity between same sex male couples, after oral and manual. Also, hetero couples are just as likely to engage in it as any other kind of couple. Getting penetrated by their female partners might do lots of things for men, like provide them with an ecstatic experience, or give them some great perspective on what it’s like to be the receptive partner. It does not make them gay.

Some general ways to probe pegging possibilities? Bring it up directly over dinner, “Darling, I would like you to peg me.” Or, “You know how you’ve been asking me if we could try anal? Will you do me first?” Make sure to have lots of good information on hand. Folks could also try hinting, by mentioning articles about other people doing it, suggesting reading material, or (consensually) bringing a date to my workshop! 

Ally: As you just mentioned, not all gay men engage in or like anal sex. What are some other myths based around anal sex?

Jessy: That it will break your butt. Betty White put it best, “Why do people say ‘grow some balls?’ Balls are weak and sensitive. If you wanna be tough, grow a vagina. Those things can take a pounding.” This is also true of butts!! Both vaginas and anuses are made of fantastically stretchy, pliable, strong stuff. This doesn’t mean you don’t have to be careful with them! They can certainly sustain damage if they are rushed or forced. When trained and treated well, however, they can both open and close for practical and pleasurable reasons. Many report a better connection with their bowels, and better function, with some kind of regular anal stimulation. This doesn’t necessarily mean intercourse all the time. There are plenty of other activities to enjoy back there.

One other myth that I would like to address everywhere all the time is the idea that folks should expect anal intercourse to hurt. Anal play should never hurt. (This is also true of vulva/vaginal play!) If it hurts: slow down, add some lube, back up, or stop. Pain is our body’s way of telling us something is not working. Sex is not something people need to “get used to.” We might need to warm up, as in kiss or stroke on other body parts for a while in order to get the juices flowing, so to speak (this is often called “foreplay.” I would like a less dismissive term... “sexing the whole body?”). We might need to size up, starting small and growing bigger, over time or in the same session or both. That’s OK. We may need to take some time to figure out positions or particular activities that really get us going and that may be uncomfortable or awkward for a little while. That’s OK too. Pain is something else altogether and not something to expect or tolerate. This is about pleasure! Enjoy it!! 

Ally: It always breaks my heart when someone tells me that they hate anal sex because their first and only time was painful. I hear this from both women and men.  And you know, that is a straight-up legit reason to not like something after that.  But it makes me sad that that’s how they were introduced to the activity.  What advice do you have for those who are introducing anal sex into their relationship?

Jessy: Take it ssslllloooowwww.  Do things that feel good in the moment. I recommend starting on one’s self first, exploring the multitude of lovely nerve endings with fingers and/or anal toys. Once you know what feels good to you, you can share that more easily with others. Remember to relax, take it slow, breath deep, long breaths, stop or switch it up if it hurts, and enjoy! If you are using toys, make sure to have something with a flared base. The internal sphincter in your anus is strong and liable to pull things in when excited. 

Ally Booker is a pleasure activist, passionate about educating herself and others on sexuality, communication, boundaries, sex toy use and safety and all the other mechanics of pleasure. You can often find her at her Tucson shop, Jellywink Boutique, 418 E. 7th St.. You can reach her at 777-9434 or

About The Author

Ally Booker

Ally Booker is a pleasure activist. She is passionate about educating herself and others on cool sexuality related things like communication skills, creating and respecting boundaries, sexual self-determination, destigmatization, gender and sexual expressions, sex toy use and safety, and all the other mechanics...
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