Ask the Sex Doc 20: Hotdog in a keyhole, "The Orange Trick," and friends-with-bennies


Oh, are you new here? Here's the run-down: One IU Kinsey Institute Ph.D., one smartass, once a week. Got a burning question? That's how we keep this crazy train chugging along, so send 'em in! or use our magical anonymous Tumblr inbox. 

Keyholed V Hole

I'm a fella who's on the larger side and am currently dating a petite young lady. Even after engaging in all of the normal pre-intercourse fun, she still experiences a lot of discomfort when we begin to have sex. After we're going for a bit, things resolve themselves and she doesn't experience any pain. Besides taking a proverbial shower in lubricant, which we already do, is there anything we can try to make our size differences a bit more manageable?

Sarah: So what you're dealing with here is a kind of hot-dog-in-keyhole kind of a situation, which, many ladies and gentlemen will find an enviable, er, position to be in. My best advice, as I'm sure the good doctor will quickly back me up on, is to go crazy on the foreplay part of the evening (think of it like a game where the last person to orgasm wins). If you are wondering if she's ready to go, throw on an Al Green or Lee Fields record and watch as her hips swirl in a figure 8 pattern under their own steam, separate from the motion of the rest of her trunk. As far as the lube goes, I gotta take a little issue with the shower technique, but I appreciate your thoroughness. What if you played The Contraband Game preceding the intercourse part of the evening? For those not familiar, The Contraband Game is where you pretend his penis is contraband and there are Cock Police in the area. You have to hide the dick, but also stay really quiet as to avoid detection by the fuzz. While you're "stashing," she can get used to your battering ram of a dong (tip of the hat, by the way) and let things just sort of settle and adjust until the coast is clear. Double bonus if you guys wear all-black stakeout clothes.

Debby: Yes! Take advantage of the wonders of the vagina. After sufficient sexual arousal, the vagina often lubricates well on its own and goes through a process called vaginal tenting in which the vagina stretches a bit in length and width, thus making penetration more comfortable for women (Fun Fact: the vagina, in its natural non-aroused resting state, is only about 3-4 inches long so we need all the tenting we can get for comfortable intercourse!). Spending at least 10 minutes doing highly arousing things (whatever that means for her) prior to intercourse may help enhance lubrication and the tenting process. If you're on the larger side or she doesn't lubricate as much as would be helpful (many forms of hormonal birth control can decrease women's lubrication as can some allergy meds, among other things) then adding water-based or silicone-based lubricant can make a world of difference. Water-based is often easier to clean-up but silicone-based lubricant lasts longer so you may want to sample each and see which you two prefer. Adding lubricant to her vaginal opening and to your penis may help as can starting with female-controlled positions, like woman on top, so that she she can control the pace and vigor of penetration until she's feeling more comfortable. Check out Sex Made Easy: Your Awkward Questions Answered for Better, Smarter, Amazing Sex for more tips on making sex more comfortable, less painful, and more pleasurable - as well as managing genital fit challenges.

Orange You Glad She Sucks

My friend told me about giving her fiance a blowjob using a cut circle of orange to jack off the base of the dick and keep it lubricated. Two things that I have to know: aren't oranges really acidic and wouldn't that be bad for sensitive skin? And do you cut a small hole in the slice or a hole that's actually "to size"? I could go on but I won't.

Sarah: Oh jeeze louise, are we about to go through another episode of Cosmo's banana-in-the-pussy fiasco? (For those outside the know, Cosmopolitan magazine, on whom women can blame their sense of sexual inadequacy and men can blame for that weird, fucked up move your woman tried on you recently, once advised filling your vag with mashed up banana for a "treat for your man." God, please die already, Cosmo.) Look, I get it: giving head can sometimes be highly performatory, while at others, minimally perfunctory and we all want to make sure we have plenty of tricks in our bag. I also respect creativity in all forms. Here's a little insider tip, too: if there's a fuckable fruit out there, most dudes have already fucked it before they can legally vote. The chances that you'll be introducing your man to any encapsulated piece of juice and flesh that they haven't at least considered using to turn themselves into sweet human kabob are slim to none. Also, this question seems to have done to this simple sex act what Pinterest has done to pizza: made it way more fuckin' complicated than it needs to be relative to its function in my life. Yes, it is neat that you can make tiny, individual deep dish pizzas in a muffin pan - but if you just want some goddamned sauce and cheese and crust because it's fucking pizza, roll that shit out in a fuckin' circle like a grown-ass American adult. Sorry. I get heated when people try to make food or sex harder than it has to be. You know what? Suck your dude's dick with an orange. This is America. Chase your bliss.

Debby: Not the orange trick! I read something about this in a women's magazine about 12 years ago and the other women and men I was hanging out with all sort of cringed at the idea. But one person's yuck is another person's yum, so it's all good. Yes, oranges can be acidic but it doesn't mean no one wants them on their genitals. They are also quite tasty to many people. One can theoretically slice a cross-section of an orange and then, yes, cut a hole somewhat close in size to the man's penis, thus fashioning a home-made cock ring one can eat through if desired. Using lots of saliva or flavored lubricant is another way to keep oral sex well lubricated when oranges are out of season or expensive or just not preferred (like if you don't want the bed or sofa to smell or taste like orange). Honestly, most people don't go to these lengths but that doesn't mean people can't (happily) do so. I'm reminded of an old episode of Seinfeld in which George Costanza wanted to have sex and eat a sandwich too - two of his favorite things! Maybe your friend just wants to double dip with oranges and oral sex. Or maybe sex just makes her hungry. Either way, there you are. 

All About the Bennies

I've been friends-n-bennies with a friend for coming up on 2 months or so. We get along great and were good friends long before the sexual part of our relationship began. We enjoy the time we spend outside of the bedroom and all that, but he's newly single after a seriously-fucked, long-distance LTR. I've expressed to him that I don't have an issue with him having other partners as long as he wears protection. We've agreed to let the situation ride until there's a pressing need to end the sex part, but I'm not sure when that is as I don't see myself ever having romantic feelings for him but I also don't see a reason not to stop having sex until he gets into another serious relationship, which could be months or years. Have I stumbled into a weird brand of polyamory, and what the hell happens now?

I AM SO CONFUSED. I CAN SEE NO PROBLEM HERE ONLY EXCESSIVE AMOUNTS OF AWESOME. You, my friend, have stumbled into a interpersonal dynamic that works for you right now, and which you seem to enjoy. If you're cool with him having other partners, maybe it's time for you to have other partners too. If you're with someone who you can have these kinds of conversations with (and it sounds like you've been talking this stuff out, which is awesome), then why not just enjoy it? Frankly, I'm just not sure which part of this you're sweating. Yes, you'll probably end up parting ways eventually for your own organic reasons, but that bridge crossing might be a long way off, so stop thinking about it! And stop trying to like, label it, brah. If it works, it works, and someone coming out of a "seriously-fucked, LDLTR" isn't going to want to hear a lot of noise about the "definition" of your relationship (and let's get real: no one can stand too much of that noise). You enjoy spending time together and bangin' it out, so just keep doing it until one or both of those things is no longer true. You'll know when the time is right to cut it off, and if this dude is really a friend first, you'll be able to state those reasons with a clear conscience. Here's an insider secret from me to you: no matter what "label" you put on a relationship, the thing that makes them "healthy" is a heady combination of emotional honesty and Colbert-level truthiness - both with yourself and your partner. Tuck that knowledge into your ten-gallon and git along to Fuckbuddy Ranch, cowgirl.

Well, yes, you're in a bit of an open situation and, no, you can't predict the future. Just because things seem fine as they are right now doesn't mean you are locked into "years" of friends with benefits sex with him. One of you might grow bored or annoyed with the other, or just not into the situation anymore. Then you act like adults and say, "this isn't working for me anymore, can we go back to being friends/stop/whatever else you two decide?" Regarding safety issues, keep in mind that condoms are mostly protective against HIV, chlamydia, gonorrhea, and some aspects of HPV (for example, they can be protective of HPV contacting your cervix but do nothing for HPV elsewhere not covered by the condom, such as on the mons). Condoms also offer more variable or limited protection against syphilis and genital herpes. Just something to think about given that he may be having sex with others and then you. If you're curious to read more about various forms of open and open-ish relationships, check out The Ethical Slut. 


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