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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
"I was always afraid it would hurt, but anal sex actually isn’t so much painful as it is uncomfortable. But! The discomfort is so extreme for some people that they can barely do it—like my best friend, who’s tried a few times with her fiancé and barely gotten it in, no matter how much lube they use. The key, apparently, is to be relaxed, which you really aren’t gonna be—in fact, knowing it’s about to happen will make you tense up more than usual—unless you happen to love it.
^ Nathaniel McConaghy (1993). Sexual Behavior: Problems and Management. Springer Science & Business Media. p. 186. ISBN 978-0306441776. Archived from the original on May 6, 2018. Retrieved March 25, 2018. In homosexual relations, most men do not reach orgasm in receptive anal intercourse, and a number report not reaching orgasm by any method in many of their sexual relationships, which they nevertheless enjoy.
I’ve had a lot of anal sex before with women who were already experienced and I tried it with my current girlfriend for the first time. She was a bit drunk and on her period and was having a hard time giving me a blow job so she told me to do her wherever I wanted. I asked where she wanted and suggested tits or ass, she said she was down for ass if I wanted it. I told her what I wanted (ass) because it feels so good so she asked where the lube was and I got it.
"I've tried it before and actually learned to relax and enjoy it, but only with one particular guy. He loves anal sex and was very experienced! The difference with him is that he made his priority to make sure I was relaxed, that I trusted him and was having fun. I tried it again with another person and had to shut that down immediately as that level of trust or care was absent. Although the physical dalliance between Mr. Anal Sex guy and I have stopped for a few years, we're still friends who check up on each other!" says Penelope from Los Angeles.
Receptive anal sex is much riskier for getting HIV. The bottom partner is 13 times more likely to get infected than the top. However, it’s possible for either partner to get HIV through anal sex from certain body fluids—blood, semen (cum), pre-seminal fluid (pre-cum), or rectal fluids—of a person who has HIV. Using condoms or medicines to protect against transmission can decrease this risk.
The distance between a woman’s anus and vaginal opening is very short, about an inch and a half. After the male ejaculates into his partner’s anus, his semen can easily drip out, travel across this very short space (known as the perineum), and enter his partner’s vagina. This trace amount of semen is all it takes to get some women pregnant. (Yes, really!)

Ask a girl how many guys she has had sex with and she may say only three or four. That's because most whores don't count all the men who have mouth-fucked them or had anal sex with them in the past. Somewhere in history women convinced themselves that ass fucking is a perverted act, and yet they simultaneously believe that it somehow does not count as sex. You can try and figure out how that logic works, or you can relax your mind and focus your eyes instead on this amazing collection of thousands of anal sex videos from PORN.com absolutely free for your enjoyment!
It's all about getting there in the way that works for you, and then having fun with it. "Anal sex is great when you've been properly warmed up," says Angela White, an award-winning adult star. "That doesn't mean ramming a couple of dry fingers into my rectum and calling it foreplay. The anus is not self-lubricating like a pussy so you need to either use lubricants or provide plenty of spit. Also, if you're not man or woman enough to stick your tongue in my butthole then you're not sticking anything else in there," White says.
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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