Q I'm gay and a junior in high school, and I've had a boyfriend for a year. (He's one year older than me, Dan, so relax!) We are out to our parents and everyone is supportive. We are not bullied or suicidal or using drugs. But we are frustrated! We had sex education in our schools, but they didn't cover gay sex. (Big surprise!) I tried to talk to my mom about gay sex, and all she said was "please use condoms." We tried and we used condoms, but I think we must be doing something wrong because we can't do it. We are ready to start having real gay sex---with me on the bottom, at least for now!---and we are frustrated and feel like failures as gay men. Any advice? --Tell Us Something Helpful
PS: Do we really need to use condoms? We are both virgins and each other's first boyfriend.
A You and your boyfriend aren't failing gayness, TUSH. Gay men and boys can be successes in life, in love and in the sack without acing---or even enjoying---anal intercourse. Anal doesn't define you as gay men and it certainly isn't all there is to gay sex. There are so many ways that you and your boyfriend can get off together---mutual masturbation, oral sex, frottage (AKA "wet humping") ---that are just as pleasurable, just as "real" and just as gay as anal intercourse. But if you and your boyfriend want to give anal another go, TUSH, here's a crash course in anal sex-ed.
First, experiment on your own. Use fingers and toys and lots of lube. I recommend that you get your hands on a butt plug, get your ass on that butt plug and get yourself off with that butt plug in your ass. Exploring anal penetration solo will allow you to experience anal pleasure without any pressure or expectations, TUSH. You can really take your time and you won't feel like you're disappointing your boyfriend if you have to bail.
Your boyfriend should do the same. I don't care if your boyfriend is a top---or thinks he is, or is topping because you want to bottom---your boyfriend will be a better top if he knows what it feels like to be penetrated and enjoys penetration himself.
OK! So you've both done some exploring on your own---jacked off with fingers and toys---and there you are, just you and your boyfriend, hanging out. Your butts are squeaky clean and, hey, you've got the house all to yourselves...is it time to fuck? Not yet. Now you're gonna spend some time sticking fingers and toys in your butts and jerking off together. For extra credit, you can experiment with rimming, if you haven't already, as nothing relaxes anal sphincters quite so effectively. (Once more with feeling: squeaky-clean butts!) The point is for you to do anal a few times with the boyfriend and for both of you to get off---you and the boyfriend---without his dick going anywhere near your ass.
Now you're ready to get fucked.
You're going to need lots of lube, TUSH, and lots of patience. Have your boyfriend apply lube directly to your hole; he should gently rub your hole for a bit, to help it relax, before using a finger or two to push some lube just inside you; you can apply the lube to his dick. Move into whatever position feels most comfortable for you---him on top, you on top, face-to-face, doggy-style---and point the tip of his hard cock directly at your hole. He should apply some pressure: uniform, constant, gentle pressure. You'll feel your asshole begin to open as the head of his cock enters you. Keep breathing as the rest of his dick slowly---a fraction of an inch at a time---slides into you.
Once he's all the way inside, TUSH, your boyfriend may be tempted to start banging away, porn-star style, but that would be a huge mistake. Your boyfriend should instead stay perfectly still for the first minute or two while you breathe and relax. Kiss your boyfriend and stroke yourself during the brief lull before the fucking starts. Then he starts moving inside you---very slowly. He pulls out an inch or two and slides back in, you keep breathing and stroking, he pulls back an inch or two more and slides in. With each successive thrust, your boyfriend will be able to pull out a little farther, TUSH, and before you know it, he'll be fucking the hell out of you. The whole process (the hole process?)---from patient foreplay to full-on assfucking---takes 30 minutes at least.
PS: You don't have to use condoms, but you should. Using condoms is a good habit to get into, TUSH, and if you have any concerns about cleanliness, well, a condom is your best friend. There are lots of gay guys out there---including guys as young as you---who got infected with HIV by boyfriends, including first boyfriends, who lied or didn't know or fucked up. So listen to your mother and use condoms, TUSH, along with a water-based lubricant.
Q I am an intern at the health and wellness center at my university. This is safe-sex-awareness month on campus. We got donations from some sex toy companies. Among the products we received is something marketed as Desensitizing Anal Wipes by a company called California Exotic Novelties.
We gave away these samples at our recent expo. After the fair, a student came up to my boss and me. As a young gay man, he expressed concern that desensitizing anal wipes were not safe to use, as masking pain could in fact lead to engaging in activities that you may not otherwise. I am assuming that what he meant here is that if you are experiencing pain during anal sex, you probably shouldn't proceed. I know with anal you need to take things slow, use lots of lube, and work your way up to it, but that's about the extent of my knowledge in this area. But I'd like to know what the Dan Savage take is on anal desensitizing wipes. Yay or nay? --A Sensitive Subject
A Googling "desensitizing anal wipes" got me this: "...perfect for using before anal sex to reduce friction pains and ease entry."
Anyone who's too stupid to use lube for anal sex---or anyone who is using lube but somehow doesn't realize that reducing friction and easing entry is what lube is down there to do---probably won't be harmed by a "desensitizing" moist towelette that retails for $3.99. I don't know what the active ingredient is, ASS, but I can't imagine it's a pharmaceutical-grade topical anesthetic. So I doubt that anyone who uses a DAW is going to wind up with an ass so benumbed that he won't realize he's being torn to shreds until after he sees blood and santorum all over his sheets.