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Four Pressing Sex Questions | A Cup of Jo


Ask an Expert, Alex Fine

On this chilly February day, let’s talk about something fun, shall we? Today, one of our favorite experts, Dame co-founder and resident sexologist, Alex Fine, is answering four very intimate reader questions…

Q. How do I start exploring my sexuality? For religious reasons, I plan on saving myself for marriage. But that leaves me a 31-year-old virgin, with no idea where to start. Masturbating is so intimidating!

A. If masturbation feels intimidating, but you have an interest in it, then make time to honor that feeling, acknowledge it, and work through it. Then, set some time aside to explore your desire for pleasure.

If you don’t know where to start, my suggestion would be…watch Outlander! Everyone is feeling Bridgerton right now, other people liked Fifty Shades of Grey. These are obviously very heteronormative examples, but what I am saying is to find content that has romance and sexuality, and see how that feels. What are you interested in? Is there something about connection? Is there something about commitment? Is there something about physical touch? Is there something about desire? Let that spark your imagination in terms of what you like.

You know how when you hear a foodie friend wax poetic about a certain food, it makes you want to try it? When you see or hear someone else vocalize a desire, it makes you feel comfortable asking for the same thing.

Physically, you can start slowly by going over your underwear or clothes. Also, touching doesn’t have to mean genitals; it can mean just gentle touches on your arms and seeing what feels good. As for toys, Fin and Zee are great toys for beginners as they are super simple and not intimidating.

My own experience with discovering sex was eye-opening. I discovered that my body can do incredible things! It opened up a world of creativity and desire. My sexuality also made me feel connected spiritually. I hope that by sharing this, it might help you feel less intimidated and more excited about that many aspects of pleasure. Finally, know that many people feel the same way you do! Just by expressing your interest, you are already on your way.

Q. I’m in a new relationship — two lonely nurses during a pandemic, yada yada. Great guy. Good chemistry. Nice kisses. He is the kindest guy who has ever liked me. Unfortunately, the sex (penetrative sex specifically) isn’t very good. (His penis is smaller than I’m used to, and we’re working through some erectile dysfunction.) He’s worth the extra effort. But how can we optimize our sex life? Any position recommendations? Props? Toys? I’m listening!

A. If I had to choose which is more important, a good partner or passion, I would pick a good partner, any day. Sex is something you can work on. The the first step is understanding what you and your partner each want. Spend time being honest with yourself about what turns you on, whether it’s a scenario, a certain touch or act, a visual cue, dirty talk, or whatever rings true for you. Once you uncover it, getting to a place where you can say “What turns me on is okay!” Owning it and expressing it, to me, is the most important piece. (For what it’s worth, even though I talk about sex all the time, I still struggle to communicate exactly what it is that I want.)

The good news is, as far as toys go, there are SO many products to help you! It ultimately comes down to what you like. One of our favorites is the Eva, which you can wear to provide clitoral stimulation during penetrative sex. If you like something squishier, Pom is also great, because it’s easy to squish between you and feels good if you’re moving around. If you’re looking for additional penetrative pressure, there’s Arc, a G-spot vibrator which is fantastic.

As for positions, a lot depends on angles. Penises and vaginal canals curve in different directions, so it’s not just about size, but also the curvature of both parties. Experimenting with a pillow can be very helpful. You can try any pillow, or there’s also Pillo, which is designed to provide different angles. Some people find that sex from behind provides more pressure and feels great for both partners. Keep experimenting until you find what works for you.

Q. My dream is to have a threesome, but I’m so shy. How do I seriously transition to bringing in a third? Maybe on vacation? Through an app? Does this person come into my home, with kid toys all over the floor (OMG)? Do we meet at a hotel? How does this work?

A. Full disclosure: I don’t have a kid yet. But I have had a threesome. And in my personal experience, there are certain things that live better in our heads than they do in reality. However, that is what rings true for me; it may not be the case for you. If this is your fantasy, explore it! If you decide you want to follow through, my advice is: thoughtful is the way to go.

When it comes to finding a third, apps are great. They’re a fun and intentional way to find someone who is after the same thing you are. I do imagine meeting somewhere besides your house may be better — not because of the kid stuff, but because being in a different environment will likely feel like a safer place to have this new experience.

Before moving ahead, communicate with your partner: Why do you want to try this? Why does it turn you on? What are you after? The more details, the better. With three, it can be tricky to feel like everyone is getting the right amount of attention. So, I also think it’s best to be clear about ground rules from the beginning. Do you want attention from two people, or to be part of the group? Are there certain boundaries that are important to you (no kissing, or no penetration)? Defining these boundaries, and then clearly expressing them to the third, is really important. But I say, go for it! Take the steps to see how you can make it a reality.

Q. I’ve only ever been able to climax via clitoral stimulation. Is there a way I can orgasm via vaginal intercourse? Any advice would be appreciated!

A. First, some statistics: Only 30% of women report being able to have an internal orgasm, or an orgasm via vaginal penetration. Furthermore, only 4% of women report that as their main route to orgasm. What this means is that 96% of women are climaxing via some form of clitoral stimulation. In every movie or TV show we watch, we always see orgasms — simultaneous ones, at that — happening pretty quickly. We’ve all been brainwashed to think this is how you’re “supposed” to orgasm. But the truth is, it’s not. It takes time, and it often doesn’t happen by penetration alone. Knowing that is really important.

That being said, trying to orgasm via vaginal intercourse is certainly worth exploring. If you want to explore inside of you, Arc, a G-spot vibrator, is amazing. It can help you find different pressure points inside your body, and to learn exactly which spots feel best for you. It can also help you learn how far up you want to go.

Beyond that, I’d say it is certainly possible to have an orgasm by experiencing internal penetration AND clitoral stimulation at the same time. Most people report those orgasms feel more intense, because you’re applying pressure from multiple directions. So, I suggest having sex in a way where you can have both internal and external stimulation at the same time.

If you’re interested in toys to incorporate during penetrative sex, Fin, which you wear on your hand, is a great one, since either you or your partner can use it to touch you. Personally, I really love squishy products, so I like Pom. For me, clitoral stimulation helps everything feel better. And reaching orgasm has so much to do with my mental state — more than anything else — so the biggest part is to relax and enjoy.

Thank you so much, Alex! We love you.

Dame Products

Obviously, we are huge fans of Dame, the company founded by two women who want to “make the world a happier place, one vulva at a time.” Through research, smart design and plenty of empathy, Dame aims to close the pleasure gap with toys that are beautiful and functional (like this new one, which sounds amazing). We love their mission and highly recommend them.

Great news for all readers: Dame is offering 15% off all first-time purchases with code CUPOFJO15. Thank you so much!

(This post is sponsored by Dame, a brand whose products and mission we love. Thank you for supporting the brands that help keep Cup of Jo running.)



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