You’ve often come to the aid of many a sick, demented fetishist, which has inspired me, a 23-year-old overweight brown-skinned dude who has never gotten laid, or for that matter even achieved the least intimacy with a lady, sexy or otherwise, to beg your help in locating some kindly lady who might be willing, so to speak, to ignore a poor psychologically castrated fellow’s faults and instruct him in the ways of physical love. To be fair, I should say that I’m not a perfect retard, as I did attend a bullshit Ivy League institution, I’m actively pursuing plans to obtain a professional degree, I do have a decent sense of humor, which, unfortunately, is sorely unapparent in this message, and I do not like to eat my own shit.
So please, Dan, if it is within your power as Hero of the Perverse to provide this craven bastard with an introduction to a gentle muse aged 19-35, please, please do. Interested ladies can write me at my E-mail address, email@example.com.
–Porn Really Is a Poor Unholy Substitute
Did you flunk basic composition at that bullshit Ivy League school you attended or are you on a mission to rehabilitate the run-on sentence? Christ, PRIAPUS (nice acronym, by the way–very Ivy League), there are periods on your keyboard for a reason. After good personal hygiene and a left-leaning voting record, nothing turns on the ladies like concision. If you speak the way you write, PRIAPUS, how can any woman who wants to fuck you possibly tell you if you never pause to take a breath?
I’m happy to print your E-mail address–there it is–but I wouldn’t waste much time sitting at home by the computer if I were you. With a creepy E-mail address like “firstname.lastname@example.org,” you’re probably not going to get a lot of mail from my female readers. So why not bite the bullet and see a whore? No one can fault a hard-up virgin for seeking professional help. My advice for you? Call up a few escorts, tell them the truth about your situation (miserable virgin, socially awkward, comma addict), and make an appointment with the first one who seems like a nice person. I’ve known plenty of whores in my time, and, without exception, each regarded deflowering male virgins as an almost sacred trust. Be clean, be respectful, wear a condom, and tip the lady.
I am a pretty experienced girl who settled down with a sweet, attentive, funny, wonderful guy. He’s the son of two ministers, was a virgin when I met him, and I’m his first serious girlfriend. I’ve gotten him to accept oral sex as part of a healthy sex life, and tried to introduce new things into his very limited repertoire. The last time I gave him a blow job, I got him up to a fever pitch and then slid my free hand between his cheeks and began rubbing his asshole. He went nuts and had one of the best orgasms of his life. I know full well that had I asked for permission to touch his ass before I went and did it, he would have said no. So my question is this: Is it ethical to go sticking one’s fingers in unexpected places when the other person is too aroused to stop you? Should I ask my boyfriend before I try any other little things on him, or should I trust my judgment?
–Apparently Too Experienced in Unusual Things
As a general rule, it’s only ethical to stick fingers in unexpected places if you have reason to believe your partner will enjoy the experience. If you’re reasonably sure your partner would dig having a finger up his butt, for instance, there’s nothing unethical about surprising him, so long as you’re prepared to withdraw that finger if he asks.
On the basis of that blow job, your boyfriend should be willing to defer to your superior sexual judgment in the future. If you’re at all concerned about going places without an OK from the preachers’ kid, well, then ask him for blanket permission to poke and prod. Have him repeat after you: “I probably wouldn’t have given my girlfriend permission to play with my ass, which I actually enjoyed very much. Since my first impulse when it comes to new sexual experiences is to say no, and since I recognize that saying no in this case would’ve deprived me of a mind-blowing orgasm, I hereby grant my girlfriend permission to do what she wants, when she wants, and where she wants, within reason.”
When he’s finished swearing the above oath, promise him you won’t do anything crazy, that you’ll do your best to read his physical cues, and that you’ll drop whatever you’re doing if he asks you to. Then have at him.
I’m a 27-year-old gay man who is only attracted to straight men. I do find some types of gay men attractive, but usually as soon as they open their mouths I lose interest. While that is a problem, I’ve accepted the fact that it’ll just take me a little bit longer to find that Mr. Right. Here’s my question: How do I let my straight roommate know that I will gladly assist him in his search for erotic no-strings foreplay? I’m not asking him to let me fuck him or become his lover; I just want to occasionally suck his dick. I’ve just noticed that he’s always fondling himself and he’s not getting any. So, how do I manage to make a pass at my straight roommate and keep a comfortable home?
The only way to make a pass at your straight roommate and keep a comfortable home is to get your straight roommate to make a pass at you. Here’s how it’s done: Get drunk with your roommate, but make sure he’s a little bit drunker than you are. Steer the conversation around to sex. Bring up blow jobs. Like most straight guys, your roommate will probably confide to you, his gay friend, just how depressing it is that most girls really don’t really like giving blow jobs. Tell him that’s too bad, and then tell him how much you love giving blow jobs. Then laugh, punch him in the shoulder, and tell him that if he’s ever horny for a blow job and there are no girls around, well, you’d be happy to help him out.
Do not get suddenly serious; that will make him think you’re making a pass. When he says, “No way, dude,” and laughs, you laugh and say, “You just lean back and think about girls, or watch straight porn, and I’ll take care of the rest.” Then laugh some more and change the fucking subject. Now here’s the really hard part: Do nothing. You shouldn’t try to get in his pants the same night. In fact, you shouldn’t bring the subject up ever again. If he ever takes you up on your offer, it’ll be after he comes into your room drunk one night and says, “Were you serious that night you said…?”