Dear Dan: My little dick has always held me back. I didn’t date in high school because I couldn’t stand the thought of girls discussing my tiny manhood. That said, I’ve adapted fairly well and become skilled with my tongue and hands. The biggest problem is that my dick is just small enough that the head pokes straight forward and can be seen through my pants. I never tuck in a shirt because of it. Because I am always in oversize shirts that hang past my waist, I never look professional. I’ve tried stuffing with socks and it didn’t work. Do you know of anything that can mask a pathetic johnson? I’d love to move up in the world.
—Physically Embarrassing Nub Isn’t Sufficient
Dear Penis: Have you considered packing? Trans men, drag kings, butch dykes, and even straight cis women experimenting with gender expression will sometimes pack—that is, wear “packing dildos” that create the appearance of a masculine bulge. Packers are modeled on soft cocks, not hard cocks, and they come in a range of sizes and colors. And so long as you don’t engage in false advertising, PENIS — so long as you make it clear to new partners that the bulge in your pants is not a prologue—there’s no reason why you couldn’t pack, just as there’s no reason why you and other guys with small dicks can’t strap on a regular dildo when your partner wants a deep dicking.
Dear Dan: I’m a mid-20s straight woman, and there’s a pattern in my life that I’m trying to break: Since high school, I’ve repeatedly ended up being friends with wonderful men who I shared an obvious sexual tension with at the start of our “friendships.” (Our mutual friends often noted the sexual tension.) Not a single one has ever turned into more than a one-off drunken kiss. Maybe it’s who I’m picking, but I’m starting to think that I’m the problem. An ex of mine (who I met on Bumble) told me that I give off “don’t touch me” vibes. Looking back, I can see that all my relationships started in settings where romantic interest was implied — apps, blind dates, etc. I’ve been spending a lot of time with a classmate of mine. We get along well, and he’s hot and single. How do I (for lack of a better term) seduce him?
—Dreading The Friend Zone
Dear DTFC: Don’t seduce, ask. Don’t put the moves on someone, use your words — or think of your words as your move, DTFZ. Since you give off “don’t touch me” vibes (that’s some valuable feedback from an ex!), and since we’ve asked men to do a better job of perceiving and respecting a woman’s “don’t touch me” vibes, you will have to make your interest clear and unambiguous: “Hey, classmate, we’ve been spending a lot of time together, and I was wondering if you might be interested in going on a date sometime.”
Dear Dan: I have had a very hot, sexy bodybuilder friend with benefits for many, many years. He’s Dominant and into really intense bondage and SM, and it’s fantastic. The harder he goes on me, the more aroused he gets. Sometimes he comes three times in one session, always with me in superintense and painful bondage positions. It turns him on so much — and it turns me on, too. The thing is, he hates my dick. We have so much fun during our sessions, but he won’t touch my dick and won’t let me touch it, either.
—Bodybuilder Is Neglecting Dick
Dear BIND: Ignoring your dick and not letting you come and then seeing you crawl back for more abuse is most likely part of the power trip that turns your hot, sexy friend on, BIND, and he’s unlikely to start lavishing attention on your dick on my orders. And since it sounds like he gives you plenty of hot JO material for after your bondage sessions, it’s not like there isn’t something in it for you, right?
Dear Dan: I am a public-school teacher in the United States. I love teaching, and I want to teach for the rest of my career. I am very good at it, but unfortunately that doesn’t affect my pay in the slightest. After 10 years of poverty, I’m getting tired of going without. I thought perhaps I could do some sex work on the side to help pay off my student loans and get some more money for classroom supplies. Thanks to de facto segregation, all of my students are one specific ethnicity and very poor, so I think I could easily avoid accidentally servicing a parent or relative of a student. But how on earth does someone safely and discreetly embark on sex work as a side hustle?
—Need a Second Job That Actually Pays
Dear NASJTAP: Someone you work with, someone you went to school with, someone you used to date, someone who lives in your apartment building — it’s not just parents and relatives of your students you need to worry about, NASJTAP. Vindictive exes and small-minded, sex-negative busybodies of all stripes can be a problem for sex workers. And since the consequences of being outed as a sex worker are always swift and severe for someone who works with children, you’ll want to find another side hustle. You should also get out there and support — we should all get out there and support — Democratic presidential candidates who are calling to forgive or cancel student-loan debt, like Elizabeth Warren and/or Bernie Sanders. And, yes, it’s possible to support more than one candidate at this stage of the political process.
Dear Dan: My girlfriend and I have been going strong for almost 10 months. She told me that in the past she dated only older men—her teachers, her boss, a police officer, and other older men who were, in her own words, “flat-out wrong for me” (two of them were married). I am interested in your take on why she is dating me now. I’m a couple of years younger than she is—she is 30, and I am 28. She says she sees a future with me and I’m unlike anyone she’s ever met. Can what someone likes change in this way?
—The Younger Man
Dear TYM: You may be the exception — the rare younger man your girlfriend finds attractive — or it could be that she was never attracted exclusively to older men. Just because someone dated a string of one type of person (older, younger, taller, shorter, maler, femaler), it doesn’t follow that someone isn’t interested in other types, too. Someone realizing they’re attracted to more types of people or acting on long-standing attractions to other types of people doesn’t mean they’ve changed, TYM, it means they’ve grown.
Dear Dan: I’m a 21-year-old woman. Yesterday I talked to a 26-year-old guy who won’t do cunnilingus but loves to get blowjobs. My friends judged him harshly. Does this go against the rule that people should be able to do what makes them feel good in bed without being judged? Guys who refuse to give oral sex but want to receive it make us feel as if our pleasure is not as important as theirs. Please tell me what you think.
—Desperate Clitoris
Dear DC: I think there are enough women out there who don’t like having their pussies eaten — some struggle with insecurity and shame, others simply don’t enjoy the sensation — that there’s no reason for this guy to inflict himself on women who do like having their pussies eaten. And if making your partner feel good doesn’t make you feel good — if giving pleasure as well as receiving pleasure doesn’t make you feel good — then you’re a lousy fucking lay. All that said, I agree that people should be able to do what makes them feel good in bed without being judged. But if what you’re doing in bed — or refusing to do in bed — makes other people feel bad about themselves or their bodies, well, then you should be judged harshly.
On the Lovecast, Dan enlists straight-boy help from Michael Ian Black: savagelovecast.com.
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