Relaxation is key and also making sure you're lubed up. "Like first timers, I mean really wet and slippery trust me sometimes that's the number one problem! The best sex position I've ever felt it in was laying on my stomach and he sneaked it in between my cheeks, laid down on top of me and rubbed my clit with one hand while supporting himself with the other, and whispering dirty things in my ear while nibbling on it," says Jillian Janson, an award-winning adult star.
The human papillomavirus (HPV)  is a sexually transmitted disease that causes anal warts. They grow inside and around your anus and may spread to your genitals. Itching is a common symptom. If you think you have anal warts, see your doctor. Without treatment, they can grow large and more may show up. Untreated warts can make you more likely to get anal cancer, too.
Stimulation from anal sex can additionally be affected by popular perception or portrayals of the activity, such as erotica or pornography. In pornography, anal sex is commonly portrayed as a desirable, painless routine that does not require personal lubricant; this can result in couples performing anal sex without care, and men and women believing that it is unusual for women, as receptive partners, to find discomfort or pain instead of pleasure from the activity.[6][38][39][40] By contrast, each person's sphincter muscles react to penetration differently, the anal sphincters have tissues that are more prone to tearing, and the anus and rectum do not provide lubrication for sexual penetration like the vagina does. Researchers say adequate application of a personal lubricant, relaxation, and communication between sexual partners are crucial to avoid pain or damage to the anus or rectum.[2][13][41] Additionally, ensuring that the anal area is clean and the bowel is empty, for both aesthetics and practicality, may be desired by participants.[21]
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.

27.“From a straight guy’s perspective: Like a lot of the previous comments, there’s an element of the taboo involved in it. Anal isn’t quite as accepted in ‘mainstream’ sexual discussions yet, and as such remains a bit out of reach for many curious individuals. Having already done anal on occasion with my girlfriend, the taboo is still there but has been transferred from a ‘mysterious and unknown’ sort of taboo to a ‘so rare as to be mystical’ taboo. On the pleasure side of things, it provides a nice change in sensation from vaginal, oral, and manual stimulation. And while it may not provide as much physical pleasure, its infrequency offsets that since it’s not something you’re typically used to like one of the above three. Also, the intimacy factor can’t be overstated. Because it’s such a rare occurrence for most guys (myself included), it carries a lot of weight when your girlfriend/wife/FWB/etc. gives you the opportunity. It requires more trust and communication than regular sex, and oftentimes your SO is sacrificing some of their comfort (and possibly dignity) to give you pleasure. It’s honestly both thrilling and humbling.”


For some women out there, anal sex is the cherry on top of a sexual sundae: a little extra treat that elevates something that was already delicious on its own (duh, talking about sex here). But for others, it's more like pâté: intriguing enough, worth a try, but absolutely not up their alleys (as in, a penis will probably not be going up that alley ever again).

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]
Most cases of anal cancer are related to infection with the human papilloma virus (HPV). Anal sex alone does not cause anal cancer; the risk of anal cancer through anal sex is attributed to HPV infection, which is often contracted through unprotected anal sex.[75] Anal cancer is relatively rare, and significantly less common than cancer of the colon or rectum (colorectal cancer); the American Cancer Society states that it affects approximately 7,060 people (4,430 in women and 2,630 in men) and results in approximately 880 deaths (550 in women and 330 in men) in the United States, and that, though anal cancer has been on the rise for many years, it is mainly diagnosed in adults, "with an average age being in the early 60s" and it "affects women somewhat more often than men."[75] Though anal cancer is serious, treatment for it is "often very effective" and most anal cancer patients can be cured of the disease; the American Cancer Society adds that "receptive anal intercourse also increases the risk of anal cancer in both men and women, particularly in those younger than the age of 30. Because of this, men who have sex with men have a high risk of this cancer."[75]
"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.
Anal sex can exacerbate hemorrhoids and therefore result in bleeding; in other cases, the formation of a hemorrhoid is attributed to anal sex.[3][92] If bleeding occurs as a result of anal sex, it may also be because of a tear in the anal or rectal tissues (an anal fissure) or perforation (a hole) in the colon, the latter of which being a serious medical issue that should be remedied by immediate medical attention.[3][92] Because of the rectum's lack of elasticity, the anal mucous membrane being thin, and small blood vessels being present directly beneath the mucous membrane, tiny tears and bleeding in the rectum usually result from penetrative anal sex, though the bleeding is usually minor and therefore usually not visible.[16] By contrast to other anal sexual behaviors, anal fisting poses a more serious danger of damage due to the deliberate stretching of the anal and rectal tissues; anal fisting injuries include anal sphincter lacerations and rectal and sigmoid colon (rectosigmoid) perforation, which might result in death.[5][93]
Anal sex has never been a pleasant thought to me…till last night my boyfriend and I decided to try it out. We had a few drinks together and had sex the usual entry whilst that, we were having so much fun that I insisted we try anal and of course like any other guy wouldn’t disagree, we did. WOW! It was amazing! I had 3 orgasms consecutively! Something i have never done before! What better way to enjoy your sex.

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.
Even if the anal they do on screen is hardly realistic for most people in everyday life, though, porn stars (like other sex workers) still have gobs of experience with back door play. (“I know my insides pretty well,” the anal queen Mandy Muse told me, “considering I’ve gone pretty far up and touched them.”) Sure, they sometimes have nasty accidents, or suffer horror stories. And, barring one or two like Kelly, who says that in her personal life she likes to “be ripped around and stretched to the core in an anal Olympics session” like she is on screen, most say they don’t do it nearly as often in their personal lives, and certainly not as hardcore or for as long as they do in scenes. But they know anal, and are happy to share tips for how to do it well.
First, I’m going to talk about some of the fundamental tips for having great anal sex, then we’re going to cover the actual anal sex techniques and positions you should be using during the act. If you want to skip straight to the anal sex techniques and positions section, click here. I have also created a separate guide here on how to full prepare your body for anal sex (hygiene, etc.).
If you're playing with silicone-based toys and need a water-based lube, Sliquid Sassy is a great option that's specifically intended for anal play. It's got a thicker texture than many water-based lubes as a result — almost gel-like — to offer you all the lubrication you need. As with all water-based lubes, it'll dry out faster than silicone, but a little bit of water splashed on the right area will "re-activate" it if you need a boost when it comes to the slippery factor.
"I tried it once a long time ago. The guy I was seeing wanted to do it, and I was resistant but eventually gave in. He tried to put it in, but it just hurt too much. I don't think he used lube, and it's just really tight. Maybe I'd do it again with the right person if I had a lot of trust in him. Either way, it's not something at the top of my list." —Clara A.
The term buggery originated in medieval Europe as an insult used to describe the rumored same-sex sexual practices of the heretics from a sect originating in Bulgaria, where its followers were called bogomils;[123] when they spread out of the country, they were called buggres (from the ethnonym Bulgars).[123] Another term for the practice, more archaic, is pedicate from the Latin pedicare, with the same meaning.[124]
Anal sex or anal intercourse is generally the insertion and thrusting of the erect penis into a person's anus, or anus and rectum, for sexual pleasure.[1][2][3] Other forms of anal sex include fingering, the use of sex toys for anal penetration, oral sex performed on the anus (anilingus), and pegging.[4][5] Although anal sex most commonly means penile–anal penetration,[3][4][6] sources sometimes use anal intercourse to exclusively denote penile–anal penetration, and anal sex to denote any form of anal sexual activity, especially between pairings as opposed to anal masturbation.[6][7]
“The truth is that our minds have this incredible way of making things less enjoyable for us, if it’s something that we’re not totally into,” Levkoff says. “If we’re nervous or uncomfortable our body shows it — our muscles tighten, we start to clench, we feel anxious, we’re not relaxed and ready anymore, and that means we’re less likely to feel pleasure.”

The anal sphincter acts as a bit of a gatekeeper for the rectum. For anal sex, however, it’s important that this muscle relaxes. Not only does it make the experience more pleasurable, it reduces the risk of tearing or discomfort. Relaxation involves patience, both at the time you’re attempting penetration, and as you become more accustomed to anal sex.
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