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I happened to be in a local store and wandered over to where they keep condoms. I had no idea there are so many different kinds! Where does a beginner start? Are women responsible for buying condoms? What about latex allergies? And lastly, what should I keep in my nightstand? Do I have to buy various types and sizes since I’ll have no idea what my date may be into?

Help! I’m so lost.

—Karen

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Q: DEAR EMILY,

Dear Emily,

I’m very educated about sexual health and open-minded sexually, but I have a hard time accepting my boyfriend’s porn habit. We have a great sex life and try new things, but he still watches porn. I can’t help wondering…aren’t I enough?I’ve seen porn before, and I know most guys watch it, but I can’t help feeling a little insecure. Is he comparing me to these women? Is that how he wants me to act? It isn’t fair for me to ask him to stop, so how can I get used to it?Please help!

Janine, 27, Iowa

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Q: DEAR EMILY,

Stocksy

I recently started seeing a guy, and although his penis is magnificent and huge, it’s an even huger problem. I’m a petite woman, and so far sex with him has been very painful. I’ve managed to get through it multiple times, but I’m always incredibly sore afterward.

Is there anything I can do to lessen the pain, or is the fact his penis is too big something I’ll have to get used to?

Thanks!

Penelope, age 22

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Q: DEAR EMILY,

stocksy

Long story short, I’m soon to be divorced, and a big portion of why we’re getting divorced has to do with not having sex for close to three years. I’ve recently started seeing someone and am feeling like a virgin all over again! What advice do you have for someone who’s ready to get back in the saddle, but is so nervous about not being good in bed?

Please help!

Lindsey, 28, North Carolina

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Q: DEAR EMILY,

Getty Images

I’m just gonna dive right in. When I was 17 years old, I had never orgasmed, despite having had one or two sexual partners. So I did some research. I read that placing your clit right underneath running water is a way to reach orgasm! So, I tried it. And to this day, it is the only way I can climax.

I have a serious boyfriend now, who I have amazing sex with, but I don’t orgasm with him. What do I do? Am I doomed to only come in the presence of running water?

May, age 19

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Q: DEAR EMILY,

I am a 23-year-old lesbian, and my dating pool seems more like a puddle. I’m shy, so walking up to a woman in a bar isn’t really my thing. Conversely, I’m very feminine and have been told that women can’t easily tell that I’m gay, making me unapproachable for women who are too scared to ask.

Last but not least, I’ve noticed that I’m attracted to older women and find myself being intimidated by them because I’m not very sexually experienced.

Basically, I need suggestions on where to meet women and how to be more confident and put myself out there.

Please help!

Cassie, 23, Kentucky

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Q: DEAR EMILY,

Photo: Stocksy

My sex life with my husband almost exclusively revolves around nipple play. He and I both love giving and receiving nipple stimulation, and it’s our primary foreplay (usually a nipple-69).

In an effort to keep things new and fun, I’ve researched nipple toys but can’t seem to find any with consistently positive reviews. We’ve talked about clamps, suction toys, and even pumps, but we aren’t sure what is reliable, pain-free (we like teasing and pleasure, not pain), and useful for both women and men.

Do you have any advice for what toys or techniques could enhance our somewhat unconventional—but very satisfying!—routine?

Mallory, Age 40

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Q: DEAR EMILY,

Image via: Stocksy

This has always been a huge insecurity of mine: moaning and noises during sex. The only sound I make is if my breathing picks up naturally.

I never moan during sex and try my hardest to let out a noise when I orgasm, but it just feels so forced and fake to me. I’m so focused the whole time that if I think about it, I just end up feeling insecure. My long-term boyfriend has always told me he doesn’t care that I don’t, but do guys really mind pretty much silent sex?

What are your thoughts?

 Thanks, 
Hailey, 24, NY

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Q: DEAR EMILY,

While I have been masturbating since the beginning of high school, I’ve never had sex. The thing is, I rarely fully get off. I think the only time I have was while using a shower head. I use the Touch by We-Vibe, but once I can feel an orgasm coming on, it becomes harder and harder to get there because my clit becomes too sensitive.

Do you have any tips to help overcome this?

Thanks,

Rachel, 24, NC

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Q: DEAR EMILY,

Hi Emily,

I have recently started seeing a new man. And I have a terrible gag reflex. Like it’s honestly terrible. I gag every single time he goes too deep, and I don’t really love the taste of semen. Between the depth and worrying about the taste, I get so tense. All I want to do is finish the job without looking like an idiot. Is it all in my head, or is there a way to fix this issue?

Emma, 22, Indiana

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