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Fretting Over My First Time


I’m a 17-year-old virgin. My partner and I tried having sex, but we couldn’t get it in. I went to the doctor for contraception and I asked her why we couldn’t get it in. She said that I needed to relax; how the hell do I relax?! During sex (or trying to) I wasn’t worried. I was a bit daunted by it because I had no sexual experience — none, nada, nothing! Do you have any advice on how I can relax?

Secondly, I’ve never given oral. I want to try everything at least once. In my head I think, “I can totally do this, I’m fine, I’ll just go for it,” but when I was in the situation where I could give him oral, I couldn’t do it. I think at best, I’m worried about the taste. I’m also worried about whether he’ll like it or not, or whether it’ll accidentally brush against my teeth. Do you have any advice on how I might overcome this? Or any advice on giving head?

When I’m not writing this column, I’m teaching workshops about sex and consent. Teaching these workshops to youth has made one thing clear: Teens are getting a lot of confusing and inaccurate information about sex. Most problematically, movies, porn, and music rarely portray anyone talking to each other about the sex they’re having.

So, you’re taking great first steps towards your first time by including visiting your doctor, discussing contraception (Please also discuss STI/STD protection with your doctor and partner), voicing your worries, and seeking reliable information.

Here’s my best advice for all your questions: Talk with your partner. This sounds simple, but it works wonders and is No. 1 on the list of things-I-wish-I’d-done-differently-my-first-time amongst adults…continue reading…


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Couple Seeking Toyfriend

Straight guy here in a monogamous relationship. We’re looking to add some toys to our routine and would love to hear your opinions and suggestions on items that we could use together. We’ve been eyeballing the Oden 2 from Lelo [a vibrating, rechargeable, remote-controlled cockring priced around $180], but have no idea if it’s worth the investment. Maybe there are simpler, more cost-effective ways to start?

If I had a dime for every question I got about “couples’ toys”, I’d be able to buy you 100 Oden 2s from Lelo. I wouldn’t though, because it would probably be a waste of my money, but we’ll get to that in a minute. I totally get it: Trying to find a sex toy that physically pleases everyone simultaneously is worth searching for. The efficiency! The cost-effectiveness! The false reassurance that everyone’s needs are getting met!

When people say “couples’ toys” what they tend to mean is a toy that is actively stimulating both partners during sex and by “both” partners we tend to mean one woman and one man and by “during sex” we tend to mean penis-in-vagina. Really though, all sex toys have the ability to be “couples’ toys” based on the basic concept that being present while your partner gets his or her rocks off is also sexually pleasing to you.

Looking at it this way, CST, your options are wide open for your new couples’ toy…continue reading…

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Getting What We Came For: How did that advice turn out?

If four years of writing a sex column have taught me anything, it’s that there’s nothing more important than honoring feedback from those you get down and dirty with. Well, and that masturbation is key. So, in keeping with best sex practices, I present you with some feel-good, masturbatory feedback from this year’s V-Spot question-askers:

“New Mom Needs to Get Some”

This article was so great. My husband finally got to read it tonight. You opened a great dialogue between the two of us tonight; so thank you.

“Hopin’ 2 Open”

Thanks! Your answer is both hard to read and, of course, what I should do. (Why is the right way usually the hard way?) I will refer back to your answer for a long time to come. Why don’t you live in NYC and why aren’t you licensed to practice sex therapy yet?! ‘Cause I’m sure we will need more guidance on the road to follow.

“Bi-Curious at Bedtime”

I really want to thank you for your wonderful advice in this week’s column.

I never felt comfortable telling [my boyfriend] about my girl-on-girl erotic dreams or attractions before because I didn’t want him to feel uncomfortable about it. I was just afraid how he’d react or if he would think differently of me. I’ve felt attracted to females and have been experiencing erotic dreams like this long before I met him. So, I always felt like I was keeping a secret about my sexuality from him.

Your column inspired me to finally have that conversation with him. I feel better knowing that he knows. I just felt weird about having pretty regular dream sex with ladies while he thinks I’m only attracted to men. It felt dishonest.

I guess I don’t really know if I’m straight or not and I haven’t for awhile. But it’s okay because now I feel like I have the freedom to figure it out and talk openly about it with my partner, who means so much to me. If not for your column and advice surrounding this topic, I don’t think I ever would have told him. Thank you for that, Yana. I feel like I’m being more honest with myself and my partner.

“My Married Sex Life, For Better or Worse”

Thank you for your advice. We definitely had one of those first date kind of talks about this tonight. Ha! Thanks again!…continue reading…

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Why Don’t I Want Sex With My BF?

I’ve been with my boyfriend for six years and he was my first and only sexual partner. Sexually we struggle. Well, I struggle. The thought of having sex is like a chore. I try really hard to do it even when I don’t want to because I know he needs that and it’s a necessary part of our relationship. He isn’t forceful or anything; I just feel bad. Once I can get myself past the initiation of it, it can be enjoyable. I’m career-oriented and my focus isn’t on the relationship. The sexual aspect of it just isn’t important to me and I don’t want to do it.

However, I think about sleeping with other people all the time and I even told him that. He told me if I wanted to have a one night stand I could if I never saw that person again.

This idea is appealing because I sometimes think I might be taking my boyfriend for granted, but I just don’t have much to compare him to. I don’t know that I could actually go through with it though. It’s basically an okay to cheat! He also says I couldn’t be mad if he does it as well. I might be fine with this because I know I don’t fulfill his needs as a man.

We love each other and talk about long term. So, why don’t I want to have sex with my boyfriend? Does sleeping with someone else put me in an open relationship or is that just a hall pass? Will it work or ruin everything?

This is A LOT! So here’s some quick-and-dirty advice:

1.) Open relationships can be great! But I don’t think it’s a viable option for you two at this time as there’s other work that needs doing here.

2.) Stop having this chore-sex that you outright say you don’t want to be having. Sex doesn’t need to be forceful in order to be nonconsensual, BotC. Being together for six years does not negate the need for consent — meaning, you and your boyfriend both saying an enthusiastic “Yes!” to the sex you’re both enjoying together and actively negotiating until you can get there.

3.) No one has ever died of blue balls and your boyfriend’s penis doesn’t need you. This antiquated, sexist, bullshit reasoning that women need to submit to men because men need to get off is a social set-up. In many ways it works against both men and women and certainly against consensual, loving, good sex and it’s a set-up that your boyfriend is (subconsciously or consciously) using to his benefit…continue reading…

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Hell-Bent on Bending Over

My boyfriend and I think anal sex is super hot and are determined to be pros at it! We’ve played with fingers and anal toys and managed to have a pretty successful penile-anal penetration experience once, but it hurt so much that now I’m afraid to do it again.

I’m not against anal sex or anything mentally, but I think my body might be against it physically? Where do we go from here? Is there a way to make this work or are we doomed to a life of plain ol’ vaginal sex?

Anal sex with your boyfriend’s penis, like Rome, wasn’t built in a day, but was rather built stone-by-lube-slathered-stone and with a lot of patience. You won’t be building an entire, tourist-packed city of pleasurable anal sex in one night.

It sounds like you’ve done some good — ahem — “leg” work here what with feeling mentally engaged and turned on by anal sex, which is an often-overlooked but super-important initial step. That giant sex organ called the brain is too-often neglected, especially with anal sex. When we feel afraid what does our butthole do? It tightens right up, making penetration difficult and painful. Being genuinely mentally into the sex you’re having is very important.

However, as you’ve learned, your body can’t always work as fast as your brain. Fantasizing about letting your boyfriend’s number one celebrity kick through your VIP backdoor entrance like some kind of anal sex rockstar doesn’t make it so. You say you’ve worked up to this shining, lubey moment by playing with fingers and toys (small buttplugs, I’m assuming) which is great.

But are you taking the time to warm up with these familiar friends-of-your-fanny directly before penile penetration? Or are you banking on that one time you used a buttplug last week to tide your tushy over? Just because you managed your biggest booty plug that one time doesn’t mean your butt is now open and available to you throwing whatever you please in there…continue reading…