I am an attractive25-year-old female and I often fantasize about having sex with two men at once. The guys I've dated wouldn't even consider it. But perhaps it is best to do this with strangers in case I feel like it was a huge mistake afterward and never want to see them again. I am thinking about taking an ad out in a local paper, but what about safety? The boys might get carried away, and I doubt the police would be sympathetic when they learned I was fucking two strangers I'd only just met in a hotel room. Do you have any suggestions?
-Horny in San Francisco
My first suggestion would be to not put yourself in a vulnerable position with a pair of guys you've only just met. Which is not to say that you can't realize your fantasy with a pair of strangers--you can, HISF, you can. But if you're concerned about safety, well, then you'll have to take some precautions.
But before I walk you through the plan, I wanna clue you in: While none of the men you've dated were into this three-way, rest assured that there are men out there who fantasize about boy-girl-boy three-ways. (Think bi guys, gay couples curious about women, and straight buds who enjoyed Y Tu Mamá También a little too much.) While very few men are into boy-girl-boy three-ways, even fewer women are into them. So you're going to be in demand, HISF, and that means you've got the power, and that means you'll be able to make demands on the guys who answer your personal ad. Shit, you can make 'em jump through hoops and crawl through glass.
Okay, here's the plan: Place a personal ad, sift through the responses, and then arrange to meet the men who interest you. For your own safety, tell them you're going to need their full names and both their home phone numbers. Do NOT invite them over to your place, do NOT give them your name and phone number, do NOT make plans to have sex at your first meeting. Your first meeting should be a short getting-to-know-you session that takes place in the middle of the day and in a public place. If you click with a pair of guys, call them back after your meeting and tell them to book two hotel rooms. Why two rooms? Because on the night the big three-way goes down, a friend of yours will be staying in the hotel room across the hall. "I got a great feeling from you guys when we met," you should tell them, "and I feel like I can trust you. But just to be on the safe side, I want my friend to be there. One loud 'help' and she'll call the cops."
Will any cops you wind up calling to your hotel room be sympathetic? Probably not, but since your speech, the plan, and your pal will scare off any men with plans to rape or murder you, it's unlikely that the police will have to get involved at all.
Good luck, grasshopper, and have fun.
I usually don't need advice in this area, but I'm a little concerned that I may have to get rid of this guy I'm currently dating. He just isn't hittin' it in the bedroom. When we're doing it, it feels good for the first two minutes, then all of a sudden he comes, usually after four minutes or so. Plus he hasn't gone down yet. It's been almost a year since we first became sexually active and he hasn't done any of the freaky stuff I like. I guess I'm used to "brothas" who have larger, longer-lasting "equipment." He is white and constantly says, "You probably are like, 'Why am I with this white boy who can't keep it up.'" I just keep my mouth shut in order to not hurt his feelings. I like him a lot, but I am afraid that if we get into a serious relationship, I won't ever be satisfied. I'm afraid to ask him to use this "numbing" cream I saw while at a sex-toy party. How do I get him to last longer?
-I Need a Bigger Dick or I'm Leaving
He's not big enough or freaky enough for you, and he won't go down on you. Guess what, INABDOIL? No amount of "numbing" cream is going to solve your problems. Break up with this boy and go find yourself a long-lasting, big-dicked, freaked-out brotha.
So voting for the tighty-whitey contest was supposed to begin this week, and yet there was no mention of the contest in your July 4 column! What's the deal? Don't tell us you're canceling yet another contest, Dan!
No, I'm not canceling the "My Man Sure Looks Hot in His Tighty-Whities" Contest--God forbid!--but there were some unexpected complications. First of all, my lawyer tells me I just can't slap the pictures I've been sent up on a website for all to see (and download). What if someone sent in pictures without the permission of the person in the pictures? What if someone who entered the contest is underage? So... before I can put anyone's pics up online, I have to get signed releases and have "proof of age" on file for each and every subject. This, of course, is going to take some damn time. Rest assured, TW fans, that the pics are in, and as soon as I have the paperwork done, they'll be going online, and you will all have a chance to view the pics and vote for your favorites.
I realize I'm too late for your "answering some personal questions" column, but if you could squeeze me in, I'd appreciate it. If you could have any three people alive today over for an intimate, leisurely, conversation-filled dinner party, whom would you invite? If you could have any three people alive today over for a wild sex party that would begin immediately after the dinner party, whom would you invite?
What I'm curious about--and I've put this question to all of my friends and most of my family--is if there's any overlap. Are you sexually attracted to the people you want to converse with? Or are these two groups distinct, separate, and unequal?
-Erotic Rights Over Sold
Dinner party: Paul Krugman, op-ed columnist for the New York Times; Florence King, columnist for National Review ("Misanthrope's Corner"); and Katha Pollitt, columnist for The Nation ("Subject to Debate").
Sex party: Ashton Kutcher, star of That '70s Show; Brian Standeford, lead singer of the Catheters; and Pontus Farnerud of the Swedish World Cup soccer team.
Okay, so there's not a lot of overlap, and I suppose that means I'm a desperately shallow person. In my defense, EROS, I would point out that Florence King and Katha Pollitt are both women, which disqualifies them from attending any sex party I might host. As for Paul Krugman, well, I've never actually laid eyes on the man. For all I know, Krugman is my type--skinny, tall, boyish, old enough to vote--but somehow I doubt there are many prize-winning economists out there who look like Ashton Kutcher. However, if Krugman does look like Kutcher, he's more than welcome to stick around after dinner.