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Dear Emily,

My boyfriend and I have been together for 3 years and have been doing the long distance relationship thing for the past year. Luckily, we have the whole summer to spend together! We’ve made a ton of fun plans, including a 12 hour road trip up the coast of California… Which brings me to my question.

My boyfriend has always had a thing for fooling around in the car, and especially loves the idea of “road head”. While I’m definitely not trying to die that way, I’d love to meet him halfway and surprise him with some spontaneous car sex. I know he’ll love it no matter what, but I’m worried it’s going to be kind of awkward. How can I pull this off and make it a pleasurable time for everyone?

Thanks for everything you do,

Hanna
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vibevixen-black-woman-thinkingHi, Emily,

I’ve been listening to your podcast for two years and can’t get enough! Your advice for others has always been spot-on, so now I’ve got a question of my own. I’ve recently started to get serious about dating, and I think I’m finally ready to be in a relationship. I’ve met a couple great guys so far, but there’s one issue I keep getting hung up on: sex. I love sex and am very open, but I think that’s the problem. In the past, I’ve gotten into bed with guys pretty quickly, and it’s never turned into anything real. How long do you recommend dating someone before you start having sex? —Dee

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Dear Emily,

I have been with my boyfriend for 4 years, and love him to bits. He’s great! The only thing that kinda gets me down is that he doesn’t last as long as he used to. He says that he’s just too turned on, which I guess I understand, but he doesn’t try to help me finish. What can I do to help him last longer? And how can I get him to understand that he should be helping ME orgasm too, not rolling over and passing out?

Thank you for your insight!
Miranda from Canada

Okay Miranda, this is a sensitive situation, and not entirely uncommon. Men’s stamina has a tendency to fluctuate over time, so I’m not concerned here—there are plenty of ways you can work together to help him last longer. What I’m more concerned about is the fact that he doesn’t seem to care about pleasing you first. Continue Reading

10-reasons-why-dating-a-coworker-is-bad (1)Can Dating Your Coworker Actually Work?

Hello Emily,

I have really been getting into this girl at work. We keep it professional, but we also find time and ways to flirt and joke around. I’ve noticed though that she also jokes around with a couple other guys in the office, so I am not sure if she is into me or just flirty. What is the best way to approach asking out a girl that you work with? If it turns out she isn’t into me, work will become really awkward and I’m sure gossip and rumors will start. I don’t want to miss out on a chance to take her on a date, but only if she is interested.

Freddy

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91b50bbe1178818d644cb8f8d2be808aTurning Into An Oral Sex Pro

Hey Emily,

I dated a girl for eight years who wasn’t at all into receiving oral sex. Even though I was totally into giving her oral pleasure, she just wasn’t a fan for some reason. We eventually broke up, but because of that long relationship without it, I have no idea what I’m doing down there. Now I’m dating a new girl who is amazing, blunt and honest about what she wants in the bedroom. She recently let it drop that she likes receiving oral. How can I go from novice to pro so I can make her experience a good one?

Mike Continue Reading

10-miscari-sexuale-hot-pe-care-trebuie-sa-le-incerci-in-luna-de-miere-7Begging For A Pegging

Dear Emily,

I’m 21 and have been with my girlfriend for four years. We’re close and she’s pretty open to trying new things in bed, but I want to know how I should bring up pegging to her? She will occasionally finger my back door but she feels a little weird about it. I really don’t know if she will be into it or not and I don’t want to freak her out.

Thanks,

Dean Continue Reading

I don’t want to ruin my chances of finding something serious.

How soon is too soon to have sex with someone you’re into? Is there a magic number? You don’t want to come off eager, but you don’t want the connection to fizzle out either.

Every relationship is different, and your attraction level will vary from person to person. Sometimes you want to jump their bones on the first date, and sometimes you need to feel it out for a little longer. There’s no right answer when it comes to choosing the perfect time to consummate.

In this video, I lead long time listener Debbie to the best way to choose the time that’s right for her. Sometimes all you need is a little reminder of what’s most important when it comes to sleeping with someone new.

best-orgasms-casual-or-committed-relationshipDear Emily,

About 5 years ago, I had a casual sex relationship with a man and it was the best sex I’ve ever had. We went on a few dates, but there was no intellectual connection. Fast forward to now: I broke up with my boyfriend about a month and a half ago and recently texted my old booty-call asking if he is single. Now, I know we don’t have a connection, we will never have a relationship and we’ve both said we’re over the casual sex thing. However, I haven’t been physically satisfied for over five years with anyone except for him.

So my question is: what are the rules here? Will I be using him if I just want sex? I know he probably wouldn’t have a problem with it, but if we are both trying to find something “real”, is this all a waste of time?

Much Love,
Mixed Up in the Midwest Continue Reading

sex-love-life-2013-12-05-woman-on-laptop-mainDear Emily,

I’ve been in a sexual rut, so I’m looking for some fun ways to get excited about sex again. I’ve heard you suggest erotica as a way to get turned on, but I find the majority of porn to be a huge turn-off (especially the kind my guy watches). Am I missing something here? Or is there porn out there that’s better for me? And if so, how do I find it?

Sincerely,

*Angelica

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Did my favorite sex toy make me unable to orgasm?

This is a question I frequently get asked, mostly from women who frequent one high-powered sex toy and worry about it de-sensitizing their lady parts.

Many of us have been there. We find a toy that we love, that nails it every damn time, and give it the starring role in our solo sex life. But then, over time, the orgasms stop coming, and the worrying begins. Maybe the toy was TOO good at it’s job? Maybe it’s ruined me for all other sex toys? Why has my Magic Wand forsaken me? Continue Reading

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