am an attractive 25-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 you feel like it was a huge mistake
afterwards 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?
in San Francisco
first suggestion would be not to 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.
OK, 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.
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
not to 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” creme
I saw while at a sex toy party. How do I get him to last longer?
Need a Bigger Dick or I’m Leaving
not big enough or freaky enough for you, and he won’t go down
on you. Guess what, INABDOIL? No amount of “numbing” creme
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!
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 Web site 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?
Rights Over Sold
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