Although anal sex alone does not lead to pregnancy, pregnancy can still occur with anal sex or other forms of sexual activity if the penis is near the vagina (such as during intercrural sex or other genital-genital rubbing) and its sperm is deposited near the vagina's entrance and travels along the vagina's lubricating fluids; the risk of pregnancy can also occur without the penis being near the vagina because sperm may be transported to the vaginal opening by the vagina coming in contact with fingers or other non-genital body parts that have come in contact with semen.[82][83]

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]
11. “Probably my favorite part of anal is the initial insertion. With a vagina you can find the entry in the dark and it’s usually the easiest thing to slide in there. With her ass.. well, there’s the preparation involved which at a minimum should include lubing it up. It’s an awesome visual for the guy. I’ve had my penis bounce off her asshole when trying to insert it sometimes. It’s fun. I think also since I like having my ass played with, it’s a relatable experience.. I kind of put myself in her place during the act. It’s also really naughty to think of cumming inside her that way and it oozing out. The girls I have done anal with all wanted it at least a second time.”
9. “My old boyfriend actually broke up with me because I asked him to try anal. It’s okay because he sucked in bed anyways and he wasn’t open to ANYTHING. I’ve heard a mix about it, but I’ve always been open to trying new things in bed to keep my sex life interesting. Apparently he thought it was weird, which is fine because my current boyfriend and I love it.” – Bella, 31

Take things slowly, use plenty of lubrication, and stop if it becomes too painful. Don’t aim to have full penis penetration your first go-round. Try using a finger, and then upgrade to two or three fingers. A toy might be a good option, too, as you grow more comfortable with the sensation. After the first time or two, you and your partner will likely find that the pleasure trumps any initial discomforts.
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