6. Pay attention the butt cheeks too! Just because your ultimate goal is the butthole, doesn’t mean you should totally ghost your partner’s butt cheeks. Sadie Allison, founder of TickleKitty.com and author of Tickle My Tush–Mild-to-Wild Analplay Adventures for Every Booty, recommends starting off with a sensual booty massage. Using lube, “place your thumbs in the creases where the legs meet the butt cheeks and glide your thumbs along the crease from the inner thigh area to the outer side. Lift and repeat. Then, put your palms together in "prayer position," placing them on their tailbone and gliding up and down their buttcrack."

Using a new condom is especially important if you’re switching from anal to vaginal penetration so you can avoid moving bacteria from your anus to your vagina or urethra. Your anus is home to all kinds of bacteria your vagina and related parts aren’t used to—namely, gastrointestinal (GI) bacteria, like E. coli. When this bacteria reaches your vagina, it can cause vaginal infections, like bacterial vaginosis, which can lead to vaginal itching, burning during urination, a “fishy” vaginal odor, and gray, white, or green vaginal discharge, according to the Mayo Clinic. It can also spread to your urethra, where it can cause a urinary tract infection. According to the Mayo Clinic, this can cause symptoms like constantly needing to pee, then a burning sensation when you do, along with cloudy urine and pelvic pain.

It’s a cardinal rule of sex to never go from anal to vaginal penetration without changing the condom (even if the penetration is with a sex toy). This is because introducing fecal matter into a woman’s vagina – even if it’s her own fecal matter – places her at significant risk for developing a urinary tract infection. Women are at higher risk of getting these infections than men because a woman’s “plumbing” is such that her urethra is quite short, making it very easy for bacteria to climb up the urethra and set up camp in the bladder. In some cases, a bad urinary tract infection can even travel from the bladder to the kidneys, which is very serious.
I really want to enjoy anal sex with my husband, but can’t seem to get over that feeling of needing to go to the bathroom. I’m terrified something may come out while we do it. What’s the best way to get past that “gotta poo” feeling? We want to work up to double penetration, but that’s not going to be possible until I can work through this. BTW – I’m absolutely loving your content. Very helpful!

The other benefit of starting slow is that you'll build arousal, Pitagora says. "Use slow and gentle stimulation of the area around the anus, the anus, the area just inside the anus, and of the prostate (if your partner has one)," they say. Being fully aroused makes any sexual experience better, but in the case of anal sex it will also help you relax.
If you’re going ver-r-r-y slowly and using lots of lube, but it’s still not happening, don’t fret. There are plenty of other ways to have fun back there; there’s no need to be too hung up on penetration. But who knows? After a little tongue and finger play, you might just be warmed up enough to try again. You can also try an ‘anal easing’ lubricant, designed to gently relax the anal area for easy insertion, like this one:
"His being exceedingly well-endowed made taking it slowly and using plenty of lube the obvious choice. The oddest thing I noticed was that the initial penetration would generate a tight sensation in my throat, similar to what you might feel after a bad scare. But it was an exciting feeling, not scary at all. It's a slow but pleasantly luxurious sensation of being gently and benignly pulled inside out. It certainly was extremely erotic, and I felt aware of my entire body as an erogenous zone. I discovered I was able to orgasm via anal penetration, and anal play is something I enjoy to this day." —Mollena W.
1. Relax those booty muscles. There are a bunch of li'l muscles around your anus that can be pretty tight if you're not relaxed. And as logic follows, if those muscles and your anal sphincter are tight, inserting anything can be painful and difficult rather than pleasurable and easy. Try something like deep breathing or a relaxing massage with your partner to make sure both you and your bum muscles are sufficiently chilled out, pre-anal play.
In Japan, records (including detailed shunga) show that some males engaged in penetrative anal intercourse with males,[117] and evidence suggestive of widespread male-female anal intercourse in a pre-modern culture can be found in the erotic vases, or stirrup-spout pots, made by the Moche people of Peru; in a survey, of a collection of these pots, it was found that 31 percent of them depicted male-female anal intercourse significantly more than any other sex act.[118] Moche pottery of this type belonged to the world of the dead, which was believed to be a reversal of life. Therefore, the reverse of common practices was often portrayed. The Larco Museum houses an erotic gallery in which this pottery is showcased.[119]
The anus was designed to hold in feces. The anus is surrounded with a ring-like muscle, called the anal sphincter, which tightens after we defecate. When the muscle is tight, anal penetration can be painful and difficult. Repetitive anal sex may lead to weakening of the anal sphincter, making it difficult to hold in feces until you can get to the toilet. However, Kegel exercises to strengthen the sphincter may help prevent this problem or correct it.
1. Don't try it if you don't want to. There's a big difference between "I don't necessarily fantasize about getting a penis enema but I want to blow my partner's mind" and "I would rather die than do this but I guess I can suffer through it because he's been pressuring me." If you're in a mutually caring, healthy relationship (with a guy who goes down on you for half an hour, minimum), maybe you'll want to do it for your partner or you won't. Either way is 100 percent fine, and if he keeps pressuring you when you have made it clear that it is not on the table, tell him to suck it.
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