Dear Dan —
I'm a Savage Lovecast listener, but I'm sending this question to your column because my boyfriend would FOR SURE recognize my voice if I called the show. I'm 25, I live in Portland, and my boyfriend and I have been monogamous for five years. His dick is of average size. It's not small enough for him to have dealt with the emotional baggage associated with "small dicks." Yet, I've had sex with big dicks, and I would love to try one of those dick sheaths or extenders or whatever. But my boyfriend is a sensitive guy, and I feel like I'm going to permanently fuck up our sex life if I ask for one. How can I propose this without him feeling like his manhood is insufficient? I've heard you talk about how it's best to share your kinks as if they were added bonuses—and not as if they were terminal cancers—but I can't figure out how to talk about this without hurting his ego. Advice?
— Sincerely Loves Average Man
"Getting a sheath onto her boyfriend's dick without hurting his feelings will be a bit tricky," said Matthew Nolan of OhJoySexToy.com. "No matter their size, lads around the world are brought up with dick insecurities. Having said that, a dick sheath isn't the worst thing in the world for her to bring to the table: It involves her boyfriend as a participant, and it keeps his dick in the loop."
Matthew and his partner, Erika Moen, collaboratively create an informative, subversive, and entertaining weekly comic that focuses on the world of sex—from sex-toy reviews to interviews with people in the sex industry to sharing sex-education lessons. They research and write the text together, and Erika does all the drawing. Why comics?
"Sex education is typically very dry," said Erika. "A wall of text about abstract concepts and then some alien diagrams—it's really hard to relate that information to your own body. Comics are especially well equipped to teach people about their bodies, sexual options, and reproductive choices because they combine images and text together, making subjects approachable and visually appealing. And, hey, adding in a joke or two helps make people feel included in the conversation instead of being lectured at."
In a recent comic, Matthew gave cock sheaths a try. Cock sheaths—for those of you who haven't visited a sex-toy shop in a while—are a popular new sex toy that allows an average dude to be huge, and a huge dude to be ridiculous. They're pliable-but-firm hollow dildos that a guy wears over his dick.
"The dick sheaths I tried weren't the greatest thing for my partner and me," said Matthew. "They dull the senses and turn your dick into an unwieldy mess. Despite owning a few, my preference is to use a big dildo on my partner instead of wearing a dick sheath."
But if it's a dick sheath you want, SLAM, Matthew has some advice about how to get one.
"SLAM should suggest going sex-toy shopping with her boyfriend," said Matthew. "She could tell her boyfriend she's in a filthy mood and fancies something big. She should put the emphasis on wanting him to give her some big-toy fucking and add that this is something that you can both do together. Have him help pick out different toys—like some big dildos—while saying encouraging things like 'Ooohh, wouldn't you like to fuck me with this one?' When you come across the cock sheath, add it to your cart explaining that it would be a perfect sex-toy solution for your mood."
I'm going to break in here for a second: If you feel like your boyfriend might have a meltdown if you start talking about wanting something huge for a change—the implication being, of course, that he isn't able to provide you with that something on his own (how big are his forearms?)—head to the sex-toy shop without any stated agenda and see how he reacts to the cock sheaths on display. If he recoils from them, SLAM, you might wanna steer him over to the body paints and bondage gear. But if he seems intrigued and not threatened by the cock sheaths, ask him how he'd feel about fucking you with one of those. And what do you do if you manage to leave the sex-toy store with a cock sheath and a boyfriend whose ego is still intact?
"Be encouraging about enjoying the extra size and having him fuck you with toys," said Matthew. "When it comes to the sheath, keep it jovial—laugh about it and tell him he's sexy. "
Go to OhJoySexToy.com to see examples of Erika and Matthew's work.