Joe Newton

I'm a 17-year-old breeder chick. I really love guys. The problem is, I want to be the one with the dick. I've heard of guys who will let their wives fuck them up the ass with a strap-on. What I've never heard of is a teenage boy who'll let me fuck him up the ass. I can't place a personal ad because I am not 18, and I'm not interested in some 30-year-old guy. There's also the problem of getting a strap-on. I look more like a 12-year-old than a 17-year-old, and I'm always kicked out of sex toy stores. I can think of a few substitutes for strap-ons (cucumbers, bananas) but I can't think of a single substitute for a willing guy my own age.

Kinky Seattle Teen

Oh, lord....

Whenever I run a question from a woman who wants it -- whatever "it" might be -- the mail pours in from guys offering to give it to her. A few weeks ago, a woman wrote in complaining that her boyfriend wasn't into eating her pussy. As of today, 384 letters have arrived from guys volunteering to eat her pussy -- sight unseen, crotch unsniffed. Four years ago, I ran a letter from a woman into exactly what you're into, KST. Dozens of straight guys who were into having their asses plowed wrote in, some sent pictures, and all offered their asses up to the woman whose own boyfriend wouldn't let her go there."

Rest assured, KST: There are guys out there who would be thrilled to bend over for you. Some of these guys have probably already started composing letters they'll beg me to forward to you. Guys: Please don't waste the stamp; don't bother clicking "send". As much as I want to see every straight man in America, especially straight men in Iowa, get fucked in the ass, I do NOT forward kinky mash notes to minors. There are grown women out there, guys, women who'll fuck your asses for love or money, and I suggest you find one, buy her a drink, and beg. But don't waste your time asking me to set you up with KST.

Now, KST, how can you get your hands on a guy your own age who'll let you stick things up his ass? By creating one. If there are guys at school, at work, or at the mall who're into you, date one of them. If you decide you like your new boyfriend well enough to be sexual with him, well, it was my experience at 17 that most 17-year-old guys (even the straight ones -- especially the straight ones) could be talked into anything. Since most 17-year-old straight boys, even the sexually liberated ones, will need some time to learn that anal pleasure won't turn them gay, not being able to get your hands on a strap-on early in your new relationship is a good thing. Take things slowly, moving very carefully from fingers (trim those nails!) to tongues (make 'em shower!) to cucumbers (never bananas, trust me, KST, never bananas). By the time he's ready for a strap-on, you'll probably be old enough to walk into a sex shop and buy one. Get some lube, too, be gentle, and send me pictures.

But... if by the time you're 18 you've failed to find a straight boy you can bend to your will, write me. Knowing straight guys as well as I do, I predict that several hundred letters are going to arrive for you regardless of my having asked straight guys not to write. I'll hold on to these letters. If when you're 18 you haven't had the chance to be "the one with the dick," send me proof of your age (a photocopy of your driver's license will do), and I'll forward all the letters for you from guys in Iowa.


I'm a college student with a crush on a TA (Teaching Assistant). He seems interested in pursuing this further, but I'm a bit hung up on the whole age/authority thing. He's 31; I'm 18. And could this messing around possibly get him into deep shit? Can this possibly work out?

Giddy Schoolgirl

If fucking students got TAs in deep shit, every TA in North America would be walking around campus covered in flies. Fucking students is one of the perks of being a TA. Hell, it's the only perk. Why are TAs content with their miserable lot in life? Is it the thrill of grading papers by sub-literate freshmen? The warm feeling they get working for senile, tenured professors who refuse to retire? Access to dorm food? No, no, and no. What keeps TAs on campus is the promise of hot, sweaty sex with willing, sub-literate freshmen whose papers they have to grade. So by keeping one TA happy, GS, you're just doing your part to support higher education.

As for your other question -- can this possibly work out? -- that depends on what you mean by "work out." If you mean will you two fall in love, get married, and grow old together, then -- not going to work out. If you mean that you two will have some fun and enjoy the time you have together (you enjoy his maturity and experience, he enjoys your youth and orifices), then, yes, it's going to work out fine.

I'm a 19-year-old bisexual student at an all-girl college which is seemingly chock full of lesbians/bi girls. However, I can't seem to get any. What's up with this? Why are none of the girls here into me?

Ready for Lovin'

I get letters like this all the time. Why aren't people into me? Why can't I get laid? Why am I all alone in my apartment/dorm/office masturbating? People who send these letters usually blame the place they live ("The people in New York/L.A./all-girl colleges/maximum security prisons are so stand-offish"), or the kind of people they're attracted to ("Straight men/straight women/gay men/lesbians/TAs/cellmates are all psychos"). But this sort of problem, like most sorts of problems, is usually the complainer's own fault, and not the fault of where they live or who they're into.

Unfortunately, a letter or an e-mail doesn't give me the kind of information I need to tell someone precisely what their problem is. For instance, there's RFL. The only way I could figure out why she's striking out would be to spend some time with her. If we spent time together, I might be able to tell her that her breath stinks, or her butt's enormous, or her personality grates. Then I could advise her to floss, or hit the gym, or stop boring everyone with tirades about the World Bank. But it's not possible for us to spend time together, so I'm afraid I'm not in a position to help you, RFL.

Your friends, however, are in a position to help. Ask a friend to give you a blunt critique of your social skills and personal hygiene. If your close friend tells you you're fine, ask yourself if she's got bad breath, a big butt, and an annoying obsession with the World Bank. If she does, then you might want to get a second opinion, and a third; weigh the evidence against yourself, and then make some changes.