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18. “OK. Imagine that you are a kid at school, and you get your school lunch every day. Every day the lunch lady gives you an apple and an orange, and then tells you not to eat the orange. So every day, you eat your apple, and leave your orange sitting on the tray. You love apples. Apples are fucking amazing, you love eating them every day. But every day, for weeks, for months, for years, while you’re eating that apple, there’s an orange right there, inches away, staring you in the face.You’ve never tasted an orange before, and you wonder what it’s like. Is it as good as an apple? Is it different or the same? Around you, you can see that a few other kids are eating their oranges; they seem to be happy about it. You have a friend who’s always going on about how awesome oranges are, how the orange he ate last week was spectacular. And you love your apple; you really do. But after years of that orange staring you right in the face, of watching other people eat their oranges and love them, you just want to eat the fucking orange and see what all the fuss is about.”

If you’re using a sex toy with a partner, it’s important to have safer sex to help prevent STDs. If someone who has an STD uses a sex toy, the body fluids on that toy can spread the infection to another person who uses that toy. So wash any sex toys with mild soap and water after you use them and before they touch another person’s genitals. You can also put condoms on sex toys to keep them clean and prevent the spread of STDs — just change condoms before the toy touches another person’s genitals. And never put a sex toy that’s been in a butt into a vagina or mouth without washing it or changing the condom first. Butt germs can cause STDs and other infections.
For comfort in entering anally, it works to be really turned on before anal entry. Deep kissing, squeezing nipples, rubbing the vulva and having vaginal sex for a few minutes first really helps to relax the anal muscles. Using lots of lubricant, the penis can push slowly, and if there is any tightness at all, withdraw and wait until the woman feels ready to do it again. The second time again entering slowly will be more relaxed and ready. If the woman rubs her vulva hard as entry happens it will more likely be pleasurable . If not, withdraw and try again when ready. Certainly it helps to have a caring partner who you can trust to be gentle. Once you are warmed up you can go pretty hard and it’s likely to give you a really great orgasm, more than you get vaginally.
Fortunately, sex educators have met this rising demand with a wealth of how-to guides and things to keep in mind for those exploring anal. Unfortunately, many people dive right in without doing much research. That means, what little anal education many first timers have often comes from porn, where anal is often portrayed as easy: just shove an unlubricated toy or peen up an asshole, with no preparation, and pump hard for, like, an hour.

So you want to try anal sex. That's great! Anal play can be lots of fun — if you're ready for it. Unlike other types of sex, which most people can fumble their way through when they don't have much experience, anal sex takes some research. (And, to be clear, it's always better to think and talk through any new sexual experience before you try it with a partner).


The most common perception of anal sex is when a male inserts his penis into another person’s anus, which is mostly what this article covers. However, it can also include penetration of the anus with sex toys or fingers or stimulating the anus with the mouth or tongue. It is still considered anal sex if insertion happens, but ejaculation or orgasm does not occur.
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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.
If you’re in a committed relationship and you’ve both tested negative for sexually transmitted diseases, you might want to forgo condoms. But you also might wonder if it’s okay for your man to ejaculate inside you during anal sex. Wonder no longer: doctors say it’s perfectly fine. But again, make sure you’re monogamous and healthy, as it’s easier for the anus to sustain small tears during sex, leaving you more susceptible to infection.
So you want to try anal sex. That's great! Anal play can be lots of fun — if you're ready for it. Unlike other types of sex, which most people can fumble their way through when they don't have much experience, anal sex takes some research. (And, to be clear, it's always better to think and talk through any new sexual experience before you try it with a partner).
Oil Based Lube – Oil based lube feels a little smoother and silkier than water-based lube. It also lasts for ages, so it’s perfect for anal sex, but there are some significant drawbacks. It’s much harder to wash out of linens. More importantly, oil-based lube degrades latex condoms making them tear and rip. Bottom line, if you don’t want the condom to tear during the act, then don’t use an oil-based lube.
17. It feels best when there's some additional stimulation going on. Vaginal, clitoral, nipple-centric—whichever feels best for you. While some women only need butt play à la carte, most women can't come from anal stimulation alone. "The anal part is something that's an accent. It adds to the overall experience," says Ian Kerner, sex expert, researcher, and author of She Comes First: The Thinking Man's Guide to Pleasuring a Woman. (Incidentally, women who have had anal sex report more frequent orgasms than those who haven't.) That being said...
2. Create a chill anal play area. Listen... All sex can sometimes be messy, and anal sex and foreplay is no exception. If this is gonna stress you out to the point that you're unable to relax and enjoy yourself, try prepping your space ahead of time. Like, maybe strip the fancy sheets off your bed or cover your comforter with a soft, washable blanket.
FYI to any haters she likes being tied up, handcuffed, slapped, called slutty names and choked even when sober so no comments about how I took advantage of her drunkenness. I think if she gets into anal she’ll probably want all that and and solid anal pounding. I’m not the one into the choking or pain that’s all her fetish. I just like a good morning blow job I’m actually a bit of a prude other than anal haha but I oblige her, you gotta give to get 😉
6. Throw other stimulation into the mix. Listen, they don't make those wild-looking, three-pronged sex toys for nothing. Once you're in the groove of things, add in some clit stimulation, some vaginal stimulation, or heck, all three. Some women say this combo feels overstimulating in the best way. In any case, most women need some combination of stimulation to orgasm—whether that's clit/vaginal, or anal/clit+vaginal is totally subjective. But isn't it fun to learn new things about your own orgasms?
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