21. “I had anal sex with my boyfriend for the first time a month ago. It was my five-year anniversary gift to him and it wasn’t great for me, but I let him keep going because I’m good for my word. When he pulled out after what seemed like a decade, a little poop came out. I was pretty mortified, but my boyfriend made me feel okay about it. I don’t think we’ll be doing it again any time soon, but the experience brought us closer together.” — Lilly, 29

Nope. Not a great idea. You need to start slowly. The anus is a muscle that needs to be worked up to having larger objects inserted. Start with finger or a small (I do mean v. small) butt plug and either warm yourself up or have a partner help. To do this, lube up your finger or toy and gently massage the anus. As you feel more aroused and comfortable, work the object inside. Gently move it around to loosen up the area.
4.“Tight almost to a fault at first then…. nothing. Personally for me it’s just mental, PIV feels much better, like 500% better but sometimes it’s nice just to have that visual and mental that comes with anal. Since it’s a bit uncomfortable for her, i.e I can’t stroke like we do with PIV it’s hard for me to orgasm during anal so if we do it it’s the last 5 minutes or so of a session.”
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.
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.
39. “Many factors. Anus has a different texture and feel to it. It’s another option besides oral and vaginal. Sometimes you just want to mix it up and it’s nice to have a third option. The woman willing to take on pain for your pleasure is incredibly selfless and sexy. It doesn’t always hurt but it can even with proper technique and lube. Her willingness to do that for you is a big turn-on. It also means no chance of babies either. So less tension of things possibly going wrong and having a major life change.”
So depending on the amount of semen, umm.. how “open” it is either from earlier sex or just being able to very easily take almost any man (was that a politically correct way to say that? lol), how you wipe (STILL FRONT TO BACK), or if you get dressed quick and it all spills into your panties and then your “lady parts” are rubbing all in it as you move and walk. It is possible for enough semen to get in the vagina to result in pregnancy.
A tiny mite nicknamed the “human itch mite” causes this rash. The bugs burrow into the top layers of your skin to feed. People usually get scabies from skin-to-skin contact. It spreads quickly where people spend a lot of time close together, like in day-care centers, dormitories, and nursing homes. Sharing clothes, towels, and bedding can spread it, too. Like pinworms, your doctor may suggest treating the family if one member has it.
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.
Glickman recommends starting with your face looking down at the bed and getting on your elbows and knees, rather than hands and knees, because you want your hips higher than your shoulders, so the penetrator has easier access. He also recommends trying the position where the receiver is standing and bent over the bed, or doing cowgirl/cowboy with the receiver straddling so that they can control the depth and pace.
The anus lacks the natural lubrication the vagina has. Penetration can tear the tissue inside the anus, allowing bacteria and viruses to enter the bloodstream. This can result in the spread of sexually transmitted infections including HIV. Studies have suggested that anal exposure to HIV poses 30 times more risk for the receptive partner than vaginal exposure. Exposure to the human papillomavirus (HPV) may also lead to the development of anal warts and anal cancer. Using lubricants can help some, but doesn't completely prevent tearing.
That depends on the toy. You want something with a flared base that’s not going to get lost in there, so stick with things marketed for sexy times, not household items that double as sex toys. (It happens.) A toy can be a great warm-up for the main event; you’ll want to use something that’s easy to wash and will stimulate you in the right way. There are so many fun toys on the market – shop around and find the perfect one for you and your partner.
8. Try it on your own first. You know how it's basically impossible to tickle yourself? This isn't the same, but trying out anal foreplay on your own is informed by a similar mind-set. You won't be surprised as much by your own, um, touch. It won't be the same as it would be coming from a partner, but it's a good way to feel out if you're into the sensation.
Male-male anal sex was not a universally accepted practice in Ancient Greece; it was the target of jokes in some Athenian comedies.[106] Aristophanes, for instance, mockingly alludes to the practice, claiming, "Most citizens are europroktoi (wide-arsed) now."[107] The terms kinaidos, europroktoi, and katapygon were used by Greek residents to categorize men who chronically[108] practiced passive anal intercourse.[109] While pedagogic pederasty was an essential element in the education of male youths, these relationships, at least in Athens and Sparta, were expected to steer clear of penetrative sex of any kind. Greek artwork of sexual interaction between men and boys usually depicted fondling or intercrural sex, which was not condemned for violating or feminizing boys,[110] while male-male anal intercourse was usually depicted between males of the same age-group.[111] Intercrural sex was not considered penetrative and two males engaging in it was considered a "clean" act.[106] Some sources explicitly state that anal sex between men and boys was criticized as shameful and seen as a form of hubris.[110][112] Evidence suggests, however, that the younger partner in pederastic relationships (i.e., the eromenos) did engage in receptive anal intercourse so long as no one accused him of being 'feminine'.[113]
Anal sex can expose its participants to two principal dangers: infections due to the high number of infectious microorganisms not found elsewhere on the body, and physical damage to the anus and rectum due to their fragility.[14][16] Unprotected penile-anal penetration, colloquially known as barebacking,[73] carries a higher risk of passing on sexually transmitted infections (STIs/STDs) because the anal sphincter is a delicate, easily torn tissue that can provide an entry for pathogens.[14][16] The high concentration of white blood cells around the rectum, together with the risk of tearing and the colon's function to absorb fluid, are what place those who engage in anal sex at high risk of STIs.[16] Use of condoms, ample lubrication to reduce the risk of tearing,[2][41] and safer sex practices in general, reduce the risk of STI transmission.[16][74] However, a condom can break or otherwise come off during anal sex, and this is more likely to happen with anal sex than with other sex acts because of the tightness of the anal sphincters during friction.[16]
5. You're gonna wanna be vocal during this process. Even if you're normally very quiet during sex, this is a time you'll wanna speak up—especially your first time trying it out with a new partner. Tell them if they're going too fast (or too slow—see point 10 below), if you feel like you're literally about to poop everywhere, or if you're experiencing pain/discomfort. Also, tell them if it feels good! If you're feeling nervous, chances are your partner is, too. Positive feedback—we love it!
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