“With his taint (more properly known as the perineum). This is the entire zone between his anus and his balls (if it ain't the balls and it ain't the anus, it's the taint). It’s not an area that typically gets a ton of attention, but there are a number of nerve endings there. Plus, the sensation some…”— Vanessa Marin, bustle.com
“Start with the old hand-in-the-back-pocket move when you guys are hanging out at home, and give him a few squeezes.”— Vanessa Marin, bustle.com
“Perhaps he would feel more comfortable if he knew that you promised not to tell anyone about it (not even your bff), or if the two of you explored in the shower (for easy, unembarrassing clean-up).”— Vanessa Marin, bustle.com
“Be up-front and open about what you’d like to do. As shocking as this may sound, not everyone enjoys giving or receiving a rim job, so talk about it in advance.”— Ross Benes, nymag.com
“Go easy. It’s also worth noting that rimming doesn’t have to involve super-deep tonguing.”— Ross Benes, nymag.com
“Spit. Spit is magical. Since anuses don't self-lubricate I think it's best to start with spreading the cheeks with your hands and letting spit fall just above the hole and letting it run down.”— Levi Michaels, buzzfeed.com
“Make sure the receiver is totally comfortable. Lay him down and let him relax. Then spend some time exploring.”— Levi Michaels, buzzfeed.com
“Rim jobs aren’t just a gay thing. Gay guys are rimming each other, sure, but girlfriends are rimming girlfriends, boyfriends are rimming girlfriends, and girlfriends are rimming boyfriends.”— Madison Moore, thoughtcatalog.com
“You can still get STIs and infections hepatitis A, B, C, and HIV from rimming, so use protection.”— Lane Moore, cosmopolitan.com
“It might take a few tries to feel really comfortable with the whole BUTT thing.”— Lane Moore, cosmopolitan.com
“Unless you are using a dental dam or a facsimile, once your lips and tongue have touched the anus, you don't want to put them anywhere else until you're done.”— Selena Kitt, literotica.com
“It's good to start with kisses. Just feather little kisses around the anus. Pay attention to your lover's response. If they back away, start wide and circle in again. Sometimes you have to build up to it.”— Selena Kitt, literotica.com
“If you're both curious and interested, just not sure how to proceed, then talk about it. Who wants to give? Who wants to receive? Sometimes it's both of you, sometimes it's just one of you.”— Selena Kitt, literotica.com
“If you are curious about anal play but find rim jobs intimidating, you may want to start with fingering, anal massage, or using butt plugs.”— Keeley Rankin, bettersexed.org
“If you’re really talented masturbate the other person or use a vibrator while you perform the rim job.”— Keeley Rankin, bettersexed.org
“No, it doesn't taste bad. As long as it's clean, at least. The anus has no different of a taste than other parts of the genital area.”— Lane Moore, cosmopolitan.com
“While rimming can be orgasmic, it doesn’t actually give an orgasm. However, it can be that extra oomph that makes an O ecstatic. It is also essential step if you’re gonna shove anything bigger than a finger up there.”— Doctor V., thefrisky.com
“Make sure he thoroughly wipes up with soap and water or uses an enema a couple hours before the RJ (rim job). A sexy way to incorporate this into sex is by taking a bath or shower together and soap up his booty yourself.”— Doctor V., thefrisky.com
“If you are much taller than him, put some pillows under his knees to raise him up. That is much better than if you stoop down because your own comfort will help you maintain your enthusiasm.”— Mark Lazer, literotica.com