Sex Advice From Bloggers

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Lindsay, 28

What’s the best fake story to tell your friends when you’ve met your new significant other online?
Say that you were walking down the street with a bunch of parcels, and that you dropped the parcels all over the place and your significant other stopped to help you. And cross your fingers that whomever you’re talking to hasn’t seen the movie Green Card.

What’s the biggest mistake people make with online dating?
Probably the same they make with regular dating — not being cool. Everyone should just relax and chill out and stop expecting and analyzing everything. Also, everyone really needs to stop doing that thing where they meet someone and automatically decide that that person is everything they’ve ever wanted or needed. It’s healthy and natural to take time to decide how you feel about someone. It’s something that people with self-esteem naturally do. You can be open and still respect boundaries.

I am a guy who wants to have a MMF threesome. I wouldn’t mind incorporating a friend of mine. How do I suggest this to him, and how can we approach a girl we’ve already established we both like? I don’t want to do it drunk.
Get a hot girlfriend, make sure she’s into it, and then one day say, "Hey dude, Jane is dying to fuck your brains out, so if you guys want we can have a threesome." See? That way you have something he wants, and the threesome part is the price he has to pay to get it.

I’m a guy whose female roommate walked in on him masturbating last week. I’m humiliated. Things are weird. We haven’t talked about it since it happened. What can I do to relieve the tension? (We know what I can’t do).
It sounds like she walked in on you in a common area of the house, not your room. So the next time you’re home and she’s out, put a "Do Not Disturb" sign that you’ve stolen from a hotel on the front door. Wait for her to come home and greet her at the door with a drink and say "What do you think of my new sign system? Just kidding!" and then get drunk together and screw or something.

My boyfriend’s in a band that travels a lot. We have an open relationship, but we’re in love. When and how should I inform prospective hook-ups of this situation?
I’m so incredibly qualified to answer this! Here’s the deal: if you have an open, long-distance relationship and you want to hook up where you live but keep it casual, you are 100% guaranteed to get into a big huge intense relationship with someone and break up with the old boyfriend for him. Or string both of them along until one of them gives you an ultimatum. (It’s okay, boys don’t have feelings. Have fun!)

How soon is too soon to tell someone that you love them?
Before a guy says he loves you, he drops a lot of hints to test the waters. I don’t know if it’s the same for girls, but probably, so I would suggest waiting at least until the person has said a few "You’re amazing"s, and maybe an "I feel so good when I’m with you" or two.

What’s the best way to get a blogger to go home with you?
Tell her you’re not attracted to her, but buy her tons of drinks.

"Perez Hilton," 27
Page SixSixSix

What are some tips for leading a sex life more like a celebrity’s?
Always have a camera handy. Always have a few lesbians programmed in your cellphone. Or bisexual girls, they’re interchangeable. Make sure your drug dealer delivers. Have your Viagra — fuck Viagra, that’s for losers — have your Cialis prescription by the bed.

So Cialis is the new Viagra?
Oh yeah, yeah. [In commercial-announcer voice] With Cialis you can stay hard for twenty-four hours . . . and girls should try it too.

What are some tips for making a home video worthy of being leaked on the internet?
You need to have more than one scene. It’s got to be somewhat professional, you know? Professionally amateur. If you look at the Paris video, the Chyna video or the Pamela Anderson video, there were several scenes strung together. You really have to commit to it. If you could even afford a director or cinematographer to help you, that would be great. Craigslist comes in very handy.

Is kissing and telling just trouble? Has it ever gotten you in trouble?
Oh boy. Don’t ask me, ask Clay Aiken.

Is it really over between Nick and Jessica? Okay, that’s not an advice questions, but just tell me. Wait, I can make an advice question: how can two rich, very tan, conventionally attractive people keep their marriage together?
I think Jessica is very conservative. She’s a good little Christian girl her dad used to be a minister. I think she needs to spice it up in the boudoir a little, maybe put on some kinky fetish outfits, role-play… Wouldn’t you want to see her in a nurse outfit, bent over, Nick holding a riding crop spanking her? You know Nick is into the kinky shit, he’s all tattooed and steroided up.

What’s the best public place to get busy?
The roof of your apartment building. Everybody’s done that. If you haven’t done it, you’re missing out.

What public place is cliché?
A taxicab. If you’re gonna do it in any moving vehicle you might as well do it in one of those carriages in Central Park. At least then you could incorporate the horse in it somehow.

What’s the best way to get a blogger to go home with you?
Tempt them with some advertising. Seriously.

Trent, 30 ("And I hate to admit that.")
Pink is the New Blog

What’s the best public place to get busy?
Now this is going to sounds really bad, but public restrooms. If you’re with someone, you’re comfortable — maybe you’re not with someone you met at the club that night . . .

So not quite George Michael waiting in a bathroom.
Right. You’re with somebody, and you’re out having fun, and there’s all this excitement and you kind of don’t want to wait to get home. Find a stall.

What public place is cliché?
The car. Or in Central Park behind bushes. When they do it on Friends, it’s pretty much cliché.

My s.o. of two years just started working out, dressing differently and initiating more sex. I think this makeover was inspired by a hottie at work, and I just happen to be reaping the benefits. Should I just take them with a smile? Should I ask about it? Should I do anything else?

I would definitely ask about it. And I would try and use my advantage; say "What’s going on? And what can we do to make it about us? If there really is someone else, what can I do to make it about us?" Do not let behavior like that go, because that’s how you end up getting cheated on and dumped.

I admit that I’m somewhat of a jezebel. But I have a serious crush on the friend of someone I had a very casual fling with. Any tips on an approach that will let him know a) I’m interested; and b) I’m interested in something with a bit more substance?
I would advise her to take the jezebel down a couple notches. If you’re really interested in the person, they have to know that. Don’t play up to your reputation, unless you think that’s what’s going to work for you.

What guidelines should I set up before I make a sex tape with my boyfriend?

I don’t think I would say, "Well, I get the tape if we break up."

He’ll just make a copy immediately.
Well yeah, and that’s just not the way to start.

What’s the best way to get a blogger to go home with you?
Compliment their length of post. "That was a great long post. That was the longest post I’ve ever seen. And it was funny and it was smart and I’m coming back for more."

Jessica, 25

What’s hotter: snarkiness or detached irony?
[Laughs] Let’s say detached irony, because if I hear the word “snarky” one more time I’m gonna like slit my wrists and spray my blood all over Manhattan. I cannot stand that word!

I approve of that answer. Does detached irony work equally well for men and women?
Well, you know, detached irony in men becomes this disaffected-disillusioned-guy thing — misunderstood, angry poet-man, or whatever. I’m not sure it comes off the same way. But there’s something kind of sexy about a jaded woman. But not a worn woman.

How much sharing is over-sharing on a date?
I had a friend who would basically dump her not-so-attractive life story out on the first date. And, come on man, it’s just dinner. Just get to know each other and talk about pretty things.

What are some tips for making a home video worthy of being leaked on the internet?

First of all, be as unattractive as possible, because people LOVE that. They have to see you looking your worst. It’s sad, but it’s true. Make sure you’re holding the handheld yourself. People tend to want that angle. Talk a lot. Say a lot of really dumb stuff — the more embarrassing it is, the better it is for the internet. Also, make sure your partner (if you’re the more famous person) is totally anonymous. So everyone’s like,”Who the fuck is that?” And have lots of really nasty close-ups.

My boyfriend is freaky-tall and I’m freaky-not. Is there a sex position that would put us crotch-to-crotch but also face-to-face?

God! Um, you know what? I’ve always had a problem with that because I’m really short and I’ve always dated really tall guys. Face-to-face and crotch-to-crotch, I think probably the best thing is him sitting on the couch and you getting on top. That’s probably the best you can do.

My roommate just had her first drunken sex with a stranger (break out the champagne). I’m not president of the sleeping-with-strangers club, but she’s too ashamed. This guy was nice. How can I convince her this was fine?
[Laughs] Well, you can always use examples of hook-ups that have gone the wrong way, like “Hey, it could be worse, you could have herpes.” I also think you have to gently explain to your friend/roommate/whatever how it is these days. People do just hook up, and people do just have sex to have sex, and as long as you’re safe and no one gets hurt, and everyone’s honest about it, then it’s no big deal. And if she’s feeling really shitty about it, just rent Pretty Woman and ride it out with her, I guess.

I have a serious crush on the friend of someone I had a very casual fling with. Any tips on an approach that will let him know a) that I’m interested and b) that I want something with a bit more substance?
That’s kind of like the perfect situation almost.

The friend of a former hook-up?
Yeah, the friend of a former hook-up, especially if it was a casual fling, because that implies that there are no hard feelings, just whatever. So this friend, the object of your new affection, obviously knows you’re attractive in whatever way, so that works in your favor. I would take it slow, like have some sort of group function, a “group hang.”

The cool kids love a “group hang.”
[In super-laid-back voice] “It’s just a group hang.” If you’re going to be out at a couple of bars, invite him out to meet up with you and your friends. Keep it casual, keep it cool, on a friendly level. Even if you’re drunk and you want to go home with him, don’t. Be respectable and mature.

The new you.

Jonno, 37

I’m going abroad for three months. Are there any guidelines I should follow for carrying on a relationship that I know will be temporary? If I set the temporary status up as a rule, ahead of time — would that work?

Relationship rules were basically made to be broken. I think I’ve been in a relationship for eight years because my partner and I didn’t have any rules from the outset. We just made things up as we went along. So, if you’re going abroad and you meet someone, and you say, “Oh, it’s not going to work” from the outset, you’re already setting yourself up for not being able to deal with the unexpected. Just forget about rules, make sure you’ve had your proper shots, and you’ll be fine.

My s.o. of two years just started working out, dressing differently and initiating more sex. I think this makeover was inspired by a hottie at work, and I just happen to be reaping the benefits. Should I just take them with a smile? Should I ask about it? Should I do anything else?
You should enjoy it, but you should probably also start working out and dressing better. A little healthy competition, if that’s the right word, is a good thing in any relationship. As someone who gained maybe twenty pounds in the first year of my relationship . . . um, yeah, I’ve been there.

How can I disguise or diminish BDSM marks?
I think anything that’s supposed to work for hickeys works for BDSM marks. So, the old cold spoon on the neck.

Really? I’ve never heard of that.
Yeah, you put a spoon in the freezer for a little while, then you press the back of the spoon against the bruise. It’s just another kind of cold compress. But it actually does work. It reduces swelling.

What are the rules on kissing someone after giving them head?

That’s your rule, "yes"?
Yes, I think you should kiss them after you give them head, and they shouldn’t have a problem with you kissing them after giving head.

What about after licking someone’s ass?
Sure. [Laughs.] If you’re interested enough to get in that position, what’s a kiss after it? If you’re going to be grossed out by that, you shouldn’t be in that position in the first place.

What’s the best way to get a blogger to go home with you?
E-mail them naked pictures or buy them something from their Amazon Wish List. That’s always worked for me.

Chris, 21

Is kissing and telling just trouble?
Alright, without going into too much detail, there was an incident with a girlfriend at the time where, ah—I don’t know how to put this—let’s say she took more than she could handle and ended up expelling what she had eaten that day. I ended up relating that story to a friend, ONE FRIEND, and that instant messenger conversation was posted on said friend’s blog. And of course, as all things do, it got back to her. Anytime you don’t want something to get back to someone, it obviously will.

What are some tips for making a home video worthy of being leaked on the internet?
Being leaked on. R. Kelly found that out the hard way.

So it really has to be standout different?
Yeah, I would say if you want to get leaked, you really might literally have to be leaked on.

The last time I was at my friend’s apartment I went looking for a sweatshirt to borrow and found pictures of me intermingled with porn magazines in his drawer. What should I do now?
In high school, I totally was that guy. I’d suggest this person run very fast. It’s not healthy to even keep talking to someone like that if they’re looking for something that’s never going to happen.

What guidelines should I set up with my partner before making a sex tape?
I think a lot of guys, if they have a partner who’s consenting to something like that, might think all bets are off and they can make whatever they’re watching on their computer at night. You should probably lay down ground rules: "Please don’t pull my hair out." "Please don’t slap me in the face with your dick." (Which I think is a favorite.) Stuff like that.

What are the rules on kissing someone after giving them head?
I guess it’s a personal preference. I know dudes who will storm out of the room angry if a girl tries to kiss them afterward. That’s not cool. She put in some work down there.

What about after licking ass?
That might be a little different. But you know, if they’re willing to do that for you, you could give them a little peck afterward.

How soon is too soon to tell someone you love them?
That’s a mistake I’ve made a couple times: jumping into that too soon, and maybe when it’s not appropriate. Within a couple months of a relationship starting, to say that might be somewhat presumptuous. The thing is, I know dudes, and I won’t name any names, but I know dudes who will use that as "the stunner." They might just break it out if maybe on a certain night . . .

"I love you — let’s have anal sex."
Yeah, or not even that, just as a prelude, if they don’t think it’s going to happen — "Oh, and I love you." And that is nothing but trouble.

Interviews by Kate Sullivan. Sex Advice From… appears on Thursdays. Have questions for the general public? Send them to

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