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Wasted Youth

November 18, 1999

I am an 18-year-old college student. It's been said that college is the time in your life when you can get the most ass. My question: WHERE'S MINE?!?! I'm not some 300-pound Dungeons & Dragons-playing dork. I'm your average 6'2", 135-pound recovering drug addict. There was an article about me in the school paper and my struggle to get clean and how I'm a better person because of it, but no dates came as a result.

I don't know what the problem is with the bitches here at my university. Goddammit, I'm from Long Island where people are normal and not like these goddamn rich bitches on campus here in Buffalo. What the hell is in the water in places like Levittown and Great Neck that makes the women into tube-top-wearing snobs?

Lounging Around, Longing for Ass

Gee, LALA, I don't know what's wrong with the bitches at your college. Most women can't resist scrawny teenagers who happen to be recovering drug addicts. And, hey, in addition to all that, you're also a budding misogynist prick with a terrible attitude about women! I can't for the life of me understand why hot college babes aren't kicking down the door to your dorm room.

Ahem. Listen, king dork, nowhere is it written that you have to weigh 300 pounds and play Dungeons & Dragons to be a dork. Indeed, there are probably fat boys with good social skills and positive attitudes about women -- even fat boys who play D&D -- all over your campus gettin' more ass than you ever will. Certainly more ass than you'll ever deserve.

And while most people get a lot of ass in college, they usually don't get much as pimply 18-year-old freshmen. From the second half of your sophomore year till the end of your junior year you'll get loads of ass provided you're not acting like an asshole. Unless you're on the football team you can't be a total asshole and expect to get much in the way of ass -- or any other orifice for that matter.

My girlfriend, older and more sophisticated than I am, used to bring home another girl every once in a while and we would have hot threesomes. But for the past couple of years, this stream of pleasure has completely dried up. It seems she wants a stable, normal, two-person relationship. I really love her, and she's certainly more to me than a provider of sex, but threesomes rule, especially two-girl blowjob sessions! What can I do to jumpstart the hot multi-party lovin' without making my lady feel like she's not the center of attention?

Three Two One

Perhaps your girlfriend could be tempted into having threesomes again if you arranged for another man to join you two in bed. It would seem likely that while you were enjoying all those two-girl blowjob sessions, your girlfriend may have been fantasizing about two-boy pussy-licking sessions. Your thoughtlessness in failing to arrange a two-boy PLS for her may have something to do with her putting an end to all those two-girl BJS. Make amends.

I'm a 26-year-old fag with a common problem. When I was an infant, I received radiation treatments to my pelvis to prevent the regrowth of a cancerous tumor on my tailbone. Because of the radiation, the growth of my pelvis was stunted. I'm sure you can see where this is leading: My dick is really small. I'm well aware that there is a large range of dick sizes for men, but I'm only about two inches when erect.

More than once I've been laughed out of bed when I got my clothes off. In my experience, gay men are much more hung up on size than straight women. Because I'm also short and look like I'm about 15, it seems that the guys who are interested in me tend to be borderline pedophiles who like the fact that I look young but won't get them sent to prison. If I could get into it, then I suppose a small dick would just add to the fantasy, but the whole daddy/little boy thing turns me off big-time. What's a horny fag with a little dick to do?

Boy Wonder

Get used to it. Your looks are your looks and your cock is your cock, and if you rule out or resent the men out there who appreciate your small dick and pedoriffic bod, well, you're not going to get much sex. And if a guy comes along who's attracted to your adolescent body and your little dick but can still relate to you as an adult then, hey, you win.

Look, with that dick and your bod you're never going to attract guys who are into lumberjacks and hockey players. And even if you did find a lumberjack-lover who'd sleep with you, the prospects are pretty grim for anything long-term. How would you feel going to bed every night with a man who didn't find you at all physically attractive? It's far better to have a boyfriend who's into what you got (tiny dick, boyish bod), than a boyfriend longing for what you don't got (massive cock, beefy bod).

I am a 19-year-old university student. When I was 15, I had a lover who was 28. He was absolutely ideal, and we used to meet after I got out of school, several times a week, to engage in sex play. Neither of us told anyone because of the huge age difference and my being a minor. This went on for six months, until my dad found my diary. (Oops!) The man moved out of state for fear of prosecution. I have since grown up and always look back on this man with fond memories. I would like to see him again to tell him so. I know the city where he lives, which is several hours from my university. My question is: Should I pursue this, or just cherish my memories and move on?

Former Lolita

Should you give him a call? Hm... that depends. When does the statute of limitations for statutory rape expire where you live? If your father finds out you contacted the ol' creep and gets pissed off he may call the ol' cops. In your shoes, I wouldn't contact my fondly remembered old boyfriend until he was no longer in danger of going to prison on my account.

You missed a vital piece of information that should be shared with any woman who gets involved with a crossdresser. Despite Ann Landers and Dear Abby and all protestations to the contrary, there is a good chance that when this woman's crossdressing partner gets to be about 40, he will no longer be able to live with his deep inner gender identity conflicts. At this point he will seek therapy and discover that he has really been a transsexual in denial. Then playing lesbian will cross over into real lesbianism as she (formerly he) grows breasts and later has sex reassignment surgery. While this isn't always the case, it has become a common pattern in the '90s as being a transsexual has become more acceptable.


Thanks for writing. No doubt there are many understanding wives and girlfriends out there reading this who, having gotten used to their male partner's crossdressing, are now going to live in terror of their partners announcing they're crossing over into lesbianism. Sorry, ladies.


Commenting was not available when this article was originally published.

Comments (14) RSS

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Mine gets very upset that I'm not bisexual, I can tell you that! It's a lose-lose situation. If I'm attracted to him, then he feels he's failing to be feminine, and if I'm not, then I'm being stubbornly straight, unlike all the other girls in the world who are cooperatively bisexual.
Posted by tinuviel on February 9, 2009 at 9:33 AM · Report this
Cross dressers aren't trannies. What the fuck wrote that?
Posted by 65426543 on January 15, 2010 at 6:21 PM · Report this
I meant, who, not what. But really, that was just dumb.
Posted by 65426543 on January 15, 2010 at 6:21 PM · Report this
this is a really old letter. people are more educatedabout transsecuals these days, thats just an outmoded attitude
Posted by sallybobally on January 17, 2010 at 10:57 AM · Report this
I have a friend who married his third wife and they were incredibly happy. She didn't mind at all that he borrowed her clothes. And now they're still together, even though they are both women. But, it was hard on the wife who thought that cross dressers aren't transsexuals but didn't realize that often, transsexuals first appear to be cross dressers. I've seen many a documentary on transsexuals who secretly wore women's clothes for years before coming out and transitioning. There was a race car driver who had a horrible wreck and was wearing women's underwear, and she is now happily a woman. I don't think the writer's opinion was that cross dressers are all transsexuals, just that some closeted transsexuals cross-dress. Like saying lesbians aren't transsexuals but Chastity Bono was a very vocal lesbian before coming out as Chaz.
Posted by charlie on January 19, 2010 at 8:17 AM · Report this
You can't be a lesbian if you're a man. If this cross-dresser 'grows breasts' and has surgery, he still won't be a woman - just a hormone-addled, mutilated and confused man.
Posted by keepitreal on January 21, 2010 at 9:39 AM · Report this
Or the tiny weenie guy could order some steroids from over the border, grow his tiny weenie another inch or so, then work out and get cut, like Toby Maguire in Spiderman. Just a thought.
Posted by Makenna on August 20, 2010 at 12:33 PM · Report this
You do realize that steroids shrink the penis to epically small proportions, right? That's probably not the best advice to give the guy, Makeena
Posted by MiraMac on October 21, 2010 at 7:59 PM · Report this
BedlamBabe 9
I'm a curvy D&D dork and I get plenty of sex. LALA is a twit.
Posted by BedlamBabe on February 14, 2011 at 6:55 PM · Report this
As a D&D playing chick, I am a hot commodity. In fact, I met my current boyfriend at a D&D tournament.
Posted by Thatonechick on April 5, 2011 at 9:35 PM · Report this
Steroids neither grow nor shrink the penis after adolescence. Stop with the urban myths already.
Posted by cockyballsup on July 7, 2011 at 12:59 PM · Report this
By taking hormones, maybe. Steroids, not so sure.
Posted by Riaan on July 8, 2011 at 4:20 AM · Report this
damn, I read Dan intermittantly from 93-97, and have read every column from 1998 forward. For a guy who is normally so spot on, this is the worst advice I've ever seen him print, most especially to Boy Wonder.
Posted by sweet g on July 9, 2011 at 12:22 PM · Report this
To elborate:

Boy Wonder - Early into meeting people that you're into, you should say "I don't have a big cock, but I give killer head". (Note saying "I don't have a big cock" as opposed to saying "I have a small cock"- same info, but sounds better.)

This statement has the likelihood of getting you laid/dating because, for starters who doesn't like getting killer head? Additionally, there's something compelling about the brassiness of the statement, and finally if anyone is that stuck on being a size queen then you can cut your losses there rather than wasting time and energy and possibly be laughed at during a vulnerable moment when you reveal your cock in bed.

What you should *not* do is settle for would-be pedophiles who skeeze you out because, hey, it's better than nothing.

Former Lolita - The guy isn't going to get busted for the previous underage sex just because you made contact with him. *If* you want to meet up with him (which I didn't get from the letter, but maybe you will) just don't ask to meet up with him in the state where charges might be pending and then everything's fine. Just keep in mind that while he might like to hear from you he also might be married with kids now and might now want to talk. I would just drop him a line on facebook and see what comes of it.

TranZGrrlla - While some cross-dresser are trans, some are trade, and some do it for fun, but the most common text book example is a straight guy whose so into chicks that wearing their clothes makes them feel closer to them.

ta da!
Posted by sweet g on July 10, 2011 at 8:22 AM · Report this

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