b : of, relating to, or characterized by personality traits (as orderliness, frugality, and obstinacy) considered typical of fixation at the anal stage of development : anal-retentive —often used in nontechnical contexts to describe someone as extremely or excessively neat, careful, or precise — compare genital sense 3, oral sense 3, phallic sense 2
3. Once you are both used to it, I find that often her lubrication coming out from vaginal sex and all over my penis when I pull out is all I need for anal penetration. (Tried the first time after 5-6 regular anal encounters.) Just warn her before you switch, or make sure you know her body enough before you try this without a warning. Depending on gravity and how excited she stays, I often find that she stays almost as wet in the back as the front… but she REALLY likes it as she can have multiples “back to back” in either entrance!!! Before we met, she was 35, she had tried anal once and hated it, and had only had 6 orgasms total during intercourse in her life, now she has 6 in a row or more just during the anal part of things.
Although people tend to think that having an orgasm is the goal of sex, you can get lots of pleasure from doing sexual things even if you don’t have an orgasm. In fact, putting a lot of pressure on having an orgasm can make you or your partner anxious, which can make sex stressful and less enjoyable. Relax, and remember that pleasure, not orgasms, is the goal.
It's important that we talk about all kinds of sex because not everyone is having, or wants to have, "penis in the vagina" sex. If you do have "penis in the vagina" sex and are curious about something else, or are finding that that type of sex is not for you and you'd just like to explore other options, it's helpful to know the facts. Even if you do learn more and decide anal sex is not a thing you'd like to try, it doesn't hurt to have the information.
Unfortunately, there’s a bit of a catch here. When you poop, your body should expel all the stool in your rectum, but some fecal matter might get left behind. While you probably don’t have to worry about pooping on your partner, you should know that they may be exposed to some visible or invisible fecal matter, Dr. Chinn says. No one needs to panic. It’s as simple as washing it off with soap and water (or changing the condom), washing your hands, and continuing on with your life, whether or not that means getting back to anal sex. But it’s definitely something that all parties should be aware of before you start.
In case you hadn’t noticed, hetero anal sex is, like, huge right now. Just a few decades ago, outside of queer circles, it was seen as a taboo act that only about a tenth of men and a quarter of women would cop to researchers to having tried at least once. Now, anal is a fixture of mainstream pop, not to mention porn, culture. In truth, not many hetero men or women try it, much less on the reg. (CDC data shows about a third of hetero women have ever tried anal; the number who regularly engage in it is unclear, but likely much lower. Data on hetero men experimenting with anal stimulation is hard to find, although prostate massager sales have grown rapidly of late and some reporting indicates rising interest.) Still, many sexually active folk, especially hetero women, reportedly feel pressure to dip a toe into butt stuff.
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.
Take things slowly, use plenty of lubrication, and stop if it becomes too painful. Don’t aim to have full penis penetration your first go-round. Try using a finger, and then upgrade to two or three fingers. A toy might be a good option, too, as you grow more comfortable with the sensation. After the first time or two, you and your partner will likely find that the pleasure trumps any initial discomforts.