9. Between thin water-based lubes (like Astroglide) and thicker ones (KY), go with the thicker ones, because they don't dry out as quickly. In sex educator Tristan Taormino's crazy-helpful Ultimate Guide to Anal Sex for Women, she mentions that Crisco has been a favorite of the LGBT community for a long time, but it's bad to use with condoms because it can eventually poke tiny holes in the latex.
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.
Luckily for butts everywhere, anal sex is no longer the ~taboo~ subject it once was. Which is a good thing! Women who've been there and done that say it's a welcome addition to their sexual repertoire. But just like you must walk before you can run, you must have some sort of anal foreplay before you go for the full monty of anal sex. Or, you know, you can do butt play and leave it at that forever, because it's your booty and you make the rules.
Anal sex, though often stigmatized, is a perfectly natural way to engage in sexual activity. People have been having anal sex since the dawn of humanity. Seriously, it's been documented back to the ancient Greeks and then some. So if you’re a little worried about trying it or are having trouble understanding the appeal, just know that it isn’t weird or gross.

19. If you try it a few times and hate it, don't keep trying it because you think it'll eventually be tolerable. "Assuming you have a considerate lover who's invested in you feeling good, I think you'd know within the first five times whether you like it or not," Kerner says, explaining that this depends on a variety of factors. "I've encountered women who hated receiving oral sex initially but love it now, and it was because they were self-conscious. It depends on your levels of inhibition, your feelings about your partner, your feelings about your body. If all these things are good to go, and you just don't like the sensation, you'll know pretty fast."
These days though, butt play is hot. Whether it’s Marnie getting rimmed on the hit HBO show Girls, or Harvard University offering an ‘Anal Sex 101’ workshop during their annual ‘Sex Week’, anal sex has decidedly outgrown its verboten past. A 2010 study published in The Journal of Sexual Medicine found that some 40 per cent of women ages 20-24 have engaged in anal sex at least once. And more than half have probably played around with oral or digital stimulation, whether on the giving or the receiving end.

Anal cancer forms when a genetic mutation turns normal, healthy cells into abnormal cells. Healthy cells grow and multiply at a set rate, eventually dying at a set time. Abnormal cells grow and multiply out of control, and they don't die. The accumulating abnormal cells form a mass (tumor). Cancer cells invade nearby tissues and can separate from an initial tumor to spread elsewhere in the body (metastasize).
Men who have sex with men may also prefer to engage in frot or other forms of mutual masturbation because they find it more pleasurable or more affectionate, to preserve technical virginity, or as safe sex alternatives to anal sex,[53][55][61] while other frot advocates denounce anal sex as degrading to the receptive partner and unnecessarily risky.[58][62]
While there’s definitely gastrointestinal bacteria in and around your partner’s anus, it’s probably not likely to cause a gastrointestinal illness like food poisoning when you ingest it. The exception is if they actually have a GI issue themselves, Dr. Frankhouse says. It’s a pretty simple rule: If the anilingus receiver has had any unusual bowel movements lately, it’s probably best to take this activity off the menu for now. That includes stool that’s runnier than usual, bowel movements that are more or less frequent than usual, and even irregular anal itching. All of these could be signs that there’s extra bacteria hanging out down there, which is definitely not ideal for anilingus.
Spreading STIs. Infections and diseases that are shared during sexual intercourse — such as HIV, gonorrhea, chlamydia, and herpes — can be shared through anal sex. In fact, anal sex is the sexual behavior for transmitting and getting HIV for both men and women. People on the receiving end (or “the bottom”) of anal sex are more likely to become infected with HIV than the inserting partner (or “the top”).
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