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Ask Emily

Hi Emily,

I’m 24 years old and the guy I’m dating is my first sexual partner—so I’m a newbie at everything but I’m pretty open to learning and trying new things. I know he really wants me to give him a blow job, but I don’t know how! I have a ton of fear around it. I really want to try it, but I can’t get over that scared feeling I get when I think about doing it, partly because I don’t know what I’m doing but also because I want us both to enjoy the experience.

What can I do to get over the fear and become more comfortable with giving him a blow job? And how can I make it a good one?

Mimi

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238d8b3c992f2b066532a21ef27a0430Hey Emily!

I’m a 20-year-old girl from England. As far as I know, I’m completely straight and in love with my long-term boyfriend. (OK, there was one time that I hooked up with a girl, but I decided it’s just not for me.)
Here’s the thing: When I masturbate (and even sometimes when my boyfriend is going down on me), I think about girls having sex with girls. Mainly, I imagine situations where a girl is having lesbian sex for the first time. Am I normal?! Am I even straight? There are absolutely no issues with my boyfriend and I really don’t think I’m gay. Am I maybe bisexual? Am I alone?

Thanks,
Bi-Curious Britney in Britain

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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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packing-suitcase-57284943Hi Emily, My fiancé and I have a great relationship and one of our favorite things to do is travel. My question is, what are the rules for flying with sex toys? We fly a lot and have been talking about purchasing a few toys to bring with us on our adventures, we just haven’t been sure how to go about it. What toys travel well? What might get us busted and embarrassed in a long airport line?

For example, I’ve had my eye on the Magic Wand for a long time. This may sound silly, but I’m not sure if I can only fly with it in my checked bag or if I can carry it on with me. I checked online, but couldn’t find much on the TSA website (no big surprise there). Can you help us get more pleasure out of our adventures abroad?

Thanks,
Elizabeth

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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.

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