Move over, Movember. There’s a new sheriff in town. And she doesn’t have (much of) a mustache. But she does want you to grow. In knowledge. What does that mean? It’s Butt Stuff Month. Okay, that’s not a real thing. Until now! When the butt questions beckon, one must take a crack at it. Booty calls. Got a sex or dating quandary of your own? Hit me at redeyedating@gmail.com. All questions are anonymous and all advice is shame-free. Plus, you know, free-free. (But not pun-free.)
Dear Anna,
I want to try anal sex with my boyfriend but all these websites and articles about enemas and douching and laxatives are making me nervous. Are these things really essential? — Boy Underestimates Trying This
Dear BUTT,
You don’t need to douche or use an enema (which are both of a similar aim). A laxative is probably going to do way more harm than good — unless you have that particular, messy fetish. The only thing you really need to do is make sure you’ve had a bowel movement that day. Shower-fresh booty is always a nice perk. And realize that even with the best plans and intentions, s— does happen. Otherwise: Use lube! Go slow! Stop if it hurts! And have fun.
Dear Anna,
I’m a queer woman in my 30s. I want to ask the new girl I’m dating if she’s into butt stuff — rimming in particular — but I’m shy! How do I broach the topic? — Should Help Yourself
Dear SHY,
The best way to get what you want is to ask for it! If you’re really shy you could broach the subject via text. But it’s a good idea to practice in person, since communication is important in romantic relationships (and all relationships). Whatever route you decide to take, ask some gently probing (sorry) questions about what your new person likes in bed. Keep the conversation lighthearted, be curious (not judgmental), and don’t forget to reciprocate. (This is a similar formula for having good sex in general.)
Whatever you do, don’t make fun of her if she likes something unorthodox. It’s hard to be vulnerable! And remember that the sooner you find out about your sexual compatibiltiies, the sooner you’ll be having the kind of sex you really really want. Win win. (Rim rim?)
Dear Anna,
I am a trans woman interested in anal masturbation. I’ve never tried anal play with a partner or alone. Nipple play isn’t really doing it for me and I do not want to touch my penis. Will anal masturbation help? — A New Awesome Like
Dear ANAL,
It might! And it might not. Everyone is different. But I’d encourage you to give it a try and see how it goes. In particular, you might benefit from prostate play and exploration. If you’re unfamiliar, the prostate is a nerve-packed area a few inches inside the anus. Get yourself a small prostate toy for this purpose, some lube, some candles and your favorite music. (The last two are optional.)
Aneros is probably the most well-known brand for prostate toys — they also have forums with thousands of members, some of whom might be helpful on this journey. But see what’s out there that might work for you. Some vibrate, some are remote-controlled, some are big, some are small.
If investing in a toy is too labor-intensive, you could start with a well-lubed finger. But know that some prostate-owners can’t reach their prostates with their fingers, due to mobility issues or simple physiology, which is why toys can be helpful. You can lay on your back with your knees up, get on all fours, or try inserting it while on your side, if you can reach. But your penis does not have to be involved in this exploration and play. (I wrote a much more in-depth look at prostate orgasms recently if you’d like to read or learn more.)
