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Jessica, 27
Are there sexual advantages to being unemployed?
I'm a big fan of telling someone, "Hey, I don't have to get up in the morning."
When is it okay to break up with someone over the phone?
Depends on how long you've been dating them. If it's a very casual relationship, or you don't really like the person and you've been in it just to sleep with them, then over the phone is completely okay. If you've been dating someone for more than a month, you should break up with them in person. I've never really done that. I'm not really a break-up-with-you kind of person. I'll just stop calling and, um, won't answer your phone calls.
What is the best way to tell someone I want to be dominated in bed?
I always say, "If I didn't get bruises, I didn't have fun." That usually gets the point across.
What's the worst way someone's attempted to pick you up?
That guy over there (points) just a few minutes ago! He all came up and was like, "So, tell me — who did your tattoos?" And then, of course, he wants to show me all of his tattoos. That's the most annoying, generic way to go about it. Oh, it's also sort of a dead end when guys ask me, "So, tell me — what do you do?" I'm like, "Uh, I don't do anything. I'm unemployed."
You're good friends with both the male and female halves of a couple. You find out one is cheating on the other. Do you tell?
I'm a firm believer in minding my own business, because that shit will come back to haunt you. If you break that couple up, they will get back together and they will both end up hating you.
I've cheated on the person I'm dating. I still care about them and it was a one-time indiscretion. Should I tell them?
Don't tell them! That will only alleviate your guilt. If it really was a one-time thing, telling them will only make them feel awful. But you do have to cut all ties with the person you cheated with, otherwise it'll happen again.
Which deserves more attention, the clitoris or the g-spot?
It's not good to concentrate on one thing. You've got to use the whole area.
Any words that should never be used to refer to the genitalia ("bearded clam," "piece of pork"?)
Don't say "penis" or "vagina." Terms like that are completely clinical and they make me think of being at the gynecologist, which is pretty much the last thing I want to think about during sex. Other than that, stay away from "box" and "slit." A good rule of thumb for the boys: if there's a phrase for female genitalia that makes your other guy friends laugh, there's a good chance women won't find that particular phrase flattering.
Pete, 23
Christian, 24
 Are there any sexual advantages to being unemployed?
Christian: Yeah, when you don't have to work you can spend more time with the person in the morning. Actually, that's not necessarily a good thing.
Pete: That's only if they're unemployed also. I prefer going after them job-having girls. That way they can take care of you.
When is it okay to break up with someone over the phone?
Pete: Whenever you don't feel like dealing with them anymore! I dated a girl for four years and broke up with her over the phone.
Christian: I don't think you necessarily owe a person a face-to-face breakup. Anytime you're not feeling it, you should just be able to pick up the phone and end it.
What is the best way to tell someone I want to be dominated in bed?
Pete: I've had a few girls come right out and ask me to choke them. But I've said no. I didn't wanna accidentally kill them. So I had them choke themselves. You know how some beds have that railing at the foot? I sort of put her on all fours and had her lean her neck on that railing. That way if she died, it totally wasn't my fault.
Christian: Don't use words. Just put your ass up in the air. He'll know what to do.
My boyfriend is a little shy about having sex while I've got my period. What should I do?
Pete: Your boyfriend is a douchebag! I so play on that field. If you want him to get past it, you're going to need to understand why he feels that way — is it because he thinks it's dirty?
Christian: You need to help him understand that you like to have sex during your period and help him get comfortable with it. Have him wear a condom, and hop in the shower afterward.
What's the biggest mistake women make in bed?
Christian: Not being open and receptive. Being a cold fish who's all, "Ew! No! I'd never do THAT!"
Pete: Sucking my toes. It happened to me once, and while she was doing it, I pretended to fall asleep. Then as soon as she'd fallen asleep, I gathered my shit up and snuck the fuck out of there.
In a long-term relationship, how can you keep sex interesting?
Pete: Dildos!
Christian: Movies!
Pete: New places!
Christian: Explore fetishes!
Pete: Openness…
Christian: Ass slapping!
Pete: Lubrication!
Christian: Lubrication?
Pete: I dunno. Sorry.
How do you coax your friends into group sex?
Christian: Drugs. Go with dormies. They're like sleeping pills, except really strong. You give someone a quarter and they totally pass right out.
You know I'm asking about consensual sex, right?
Christian: I took them with a friend once and we both totally ended up getting naked immediately. You can also go with other drugs.
Pete: I tried to get two friends of mine in bed, and it turned out bad. We were all sitting on the couch watching TV. The two girls were on either side of me, and I reached down and started rubbing both of their legs at the same time. They just sort of leaned forward to look at each other and were like, "There will be none of THAT tonight!" I guess the larger lesson here is, don't get stuck for a night in Providence, Rhode Island.
Male bisexuality: myth or reality?
Christian: In New York City, it's a reality. Elsewhere in America? A myth. In my experience, bi guys aren't gay, they're just oversexed. They don't want anything emotional. They don't want to hang out with you, they don't want to know you, they just want to get off and that's that.
Is there a sexual mistake you'll never make again and want to warn others against as a public service?
Pete: I broke my dick once. She was on top, and instead of going up and down, she started going side-to-side, and I heard this pop. The next day, the bottom two inches of my dick were purple and black. I could hardly walk. So I'd say, none of that side-to-side crazy stuff, okay?
Alex, 34
Did you get more sex when you were gainfully employed or now?
This is going to have to be theoretical. I haven't had sex in the last six months. Come to think of it, most of the time I haven't been having sex, I also haven't been working. Maybe there's a correlation there. (laughs)
Where are some places I could pick up unemployed people?
There's a nude beach in Eugene, Oregon, called Glass Island. Most of the people who hang out there are unemployed, and hey, they're already naked. Less specifically, maybe you could try walking around known residential areas during business hours.
What are some good cheap things you can do for a date that might lead to a person having themselves some sex?
Indian food. If it's raining, an entire evening of movies. Pay for one and then movie-hop from theater to theater.
My boyfriend is shy about having sex while I've got my period. What should I do?
Go someplace together where you can both be naked the whole day. Maybe go camping or something – somewhere where you can hang out with him while you're bleeding. Someplace where there's water. Let him see it. Get comfortable with it. It's a natural thing; he should be able to come to terms with it in the right setting.
Under what circumstances should someone fake an orgasm?
Only if you're getting paid. Never with your partner.
You're good friends with both halves of a couple. You find out one is cheating on the other. Do you tell?
This happened to me with two friends of mine. I kept it quiet. I didn't say a word. Their level of honesty with each other is their business.
How do you coax your friends into group sex?
Two words: HOT TUB.
A sexual mistake you'll never make again and want to warn others against as a public service?
Don't trust the rhythm method. Enough said.
Jess, 22
 Is it easier to get laid when you're unemployed?
I think it's probably more a question of quantity over quality. I'd say that it's probably easier to get laid more being unemployed. If you're working, you probably have less sex, but it's with better people.
Where are some places I could pick up unemployed people?
As far as the day time goes, I don't know. Being out when the sun's up is a rare thing for me. At night, your best bet is to find a party with an open bar.
What are some low-budget dates?
Forget that. You're better off going out on dates with the twentysomething kid who has a fortysomething "boyfriend." And then he can pay for everything with his "boyfriend's" credit card. Oh, or NYU students. They pay for everything.
What the worst way someone's attempted to pick you up?
I've had guys with moustaches just come up and try to kiss me, and that's just gross. It's like being kissed by your father. Most people that have come onto me have been pretty cute about it, passing me little notes with quotes from songs by The Smiths written on them while I'm DJing. Stuff like that.
What's the biggest mistake a man can make in bed?
Have a little hand-eye coordination. Clearly, there are guys that didn't play enough Nintendo when they were younger.
What qualifies as cheating: flirting, kissing, fooling around or full-on fucking?
It's the intent. You'll know if you're cheating. Also, it depends on who the other person is that you cheat with. You have to take into account how the person you cheated with will reflect upon the person you're dating. If someone I'm dating cheats on me with somebody way hotter than me, I get it. I'm like "Oh, I can see why you did that! I'd cheat on me too!" But other situations can hurt – like the time someone cheated on me with someone who had a mullet. Not even an ironic mullet, a non-ironic one. That was awful.
Well, out of those four scenarios, is there a cutoff point? If someone you're dating does one, you'd want to know about it?
Me personally, I'm happy not knowing. When people tell me, then it breaks my heart. I find the harder it is for someone to love, the harder they do love. n°
Interviews by Brian Battjer. Click here for previous editions of "Sex Advice From..."
Sex Advice From... appears every Thursday. Do you have sex-advice questions for the general public? Send them to .
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