Since STDs can still be spread through both anal and oral sex, it is a good idea to use physical protection such as a condom to protect both yourself and your partner. Since the skin of the anus and rectum is thin, prone to tears, and not well lubricated, it may also be a good idea to use a water-based lubricant to protect these delicate regions from tissue damage. A lubricant cannot, however, completely prevent tearing or injury. With oral sex, no lubricant is suggested because most brands are not safe to ingest.
For your first time, Hutcherson says spooning is better than doggy-style. “For those just starting out, I think getting on all fours might be a little too intense. Lying on your side in the spooning position won’t allow penetration that’s as deep. It’s also a more relaxing position. When you become more comfortable, the doggie is the easiest way for a woman to orgasm.” And don’t forget to breathe. Says O’Reilly, “As you breathe deeply, your inner sphincter muscle will relax to facilitate penetration.”

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Yes, you can still contract or transmit STDs through anal and oral sex. Anal sex can more easily damage tissue (tears in the lining of the anus or rectum) than during vaginal sex because the anus is not designed for insertion. Therefore, the skin barrier that often protects against infection is broken and STDs can more easily enter the body. This means that transmitting or contracting an STD is more likely from anal sex than with vaginal or oral sex.
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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