A woman wearing a sheer lace black camisole touches her chest with one hand, holding a purple orchid flower. Sunlight and shadows create patterns on her skin and clothing.

F*ck Around and Find Out with Anna Lee: Don’t listen to Freud

It's cuffing season, and when it comes to pleasure, it's key to listen to your body, not a long-dead Austrian who sometimes made stuff up

Sex education creator Anna Lee.

Henry Wu

Words by Anna Lee

F*ck Around and Find Out with Anna Lee: This is the modern sex advice column you didn’t know you needed, focused on finding confidence in your own pleasure through knowledge and research! Think a fresh reimagining from the days of those pink, star-studded magazine sex advice columns like “10 Ways to Please Your Man” that we all grew up with. In my journey from growing up in a strict, immigrant Korean household, scared of my own body, to my current reality as co-founder of a smart vibrator company and certified sex educator, I realized how much we need to destigmatize the cultural taboo around sexual pleasure. So, hold my hand (if you want to, of course) and together, let’s fuck around and find out every nook and cranny of this sexy world. 🙂 

Have a question you’d like me to answer? Keep ‘em coming by submitting it anonymously here!


As the season begins where we all start scrambling for a decent answer at holiday dinner about why we are not taking dating seriously, it can only mean one thing. We are officially in the thick of cuffing season. So take out those disgustingly adorable hand-holding mittens and sit around my imaginary fireplace while I blather away about sex advice.

Two people wear a single pair of connected black mittens with red heart buttons, holding hands. Their sweaters and pants are visible from the elbows down against a neutral background.

Told you. Disgustingly adorable.

Uncommon Goods

Okay, so I can make myself orgasm pretty easily when I’m alone, but it’s always from touching my clit. When I’m having sex though, I never actually orgasm from penetration no matter how good it feels. Is that normal? Am I missing something or doing something wrong? Like…how do people have vaginal orgasms? HELP - Anonymous

Like very normal. So normal that if we ask every woman in line for the bathroom at a club, 81.6 percent of them would say penetration alone does not do it for them either.

I am going to take this moment to flame Sigmund Freud. I have a deep distaste for that man because he would go around telling people that vaginal orgasms were the mature ones and clitoral orgasms were childish. He just randomly made that up. He also thought women envied penises, so we are truly not taking his sex advice as gospel. Anyway, here is why some people can have what they call vaginal orgasms. It all starts from the beautiful bean, the clitoris.

Most people need clitoral stimulation to orgasm. The clitoris is not just the little button on the outside. It is part of a whole structure called the CUV complex. C for clitoris, U for urethra, V for vagina. Inside, the clitoris branches out like a wishbone and hugs the vaginal canal. So what people often call a vaginal orgasm is actually the internal clitoral structures getting stimulated. The CUV complex might be positioned in a way for some people to get that through penetration, but others might find it impossible. The vagina itself has sensation but it is mostly built for stretch and pressure, while the clitoris has thousands of pleasure-focused nerve endings.

In case you think you’re missing out on something, researchers asked women who have experienced both clitoral and vaginal orgasms to rate them across a bunch of descriptive pairs like deep or superficial, slow or quick, powerful or weak. Here is the chart from their data:

A line graph compares vaginal and clitoral orgasm sensations using 20 descriptive word pairs, rated from 1 (left, e.g., deep) to 5 (right, e.g., superficial). Clitoral orgasms trend toward “quick” and “sharp.”.

Weitkamp K, Wehrli FSV. Women's Experiences of Different Types of Orgasms-A Call for Pleasure Literacy? Int J Sex Health. 2023 Mar 1;35(2):193-208. doi: 10.1080/19317611.2023.2182861. PMID: 38595859; PMCID: PMC10903554.

© 2023 Taylor & Francis Group, LLC

There were some differences, sure, but there was also a ton of overlap. Both types were rated similarly pleasant, powerful, blissful, soothing, and energetic. In real life, the experiences often blend together which makes sense because the CUV complex is one connected system.

So when you orgasm from clitoral stimulation during solo time, that is your anatomy doing exactly what it was built to do. And when penetration alone does not make you climax, that is also entirely normal!

P.S Did I mention that Freud sucks? 

I’ve been with my boyfriend for more than three years and I love him very much. He’s mentioned a few times what I thought about a threesome or going to a sex party. I always kinda laugh it off and say maybe…maybe not. He never pushes me on it beyond that and is respectful of my response. I don’t know. I think it might be kinda hot? But I also can’t imagine watching him touch someone else and feeling good about it. But maybe it’ll be more fun than I expected? I don’t know. What do you think? Am I a prude? Should I go for it? -Anonymous 

Let me be the first person to tell you that group sex is hard work. (Figuratively in this case, but I guess literally too.) It can bring on tough conversations and complex emotions. Your question reads like someone who is turned on by the idea but unsure about the reality, and that is a very human place to be.

Here is the honest bit. I think that anything group sex related only really works smoothly when these things are true.

  1. You and your partner have had deep, honest conversations about boundaries, rules, expectations, and you both always feel safe talking about the awkward stuff.
  2. You and your partner have ways to process emotions that may come up. As individuals and as partners.
  3. You and your partner are in a good headspace. Again, both as individuals and as partners.

Or 

  1. Everyone involved has no sexual or emotional attachment with anyone else participating in the group sex. 

From what you wrote, you and your boyfriend are not quite at that level of clarity yet. That does not mean something is wrong. It just means you care about him and the idea of watching him touch someone else makes your stomach drop, which is very normal. I think it could be worth having a deeper conversation about it with him. Who knows, you might find that he is also just enjoying the fantasy of it and would not actually want to see you touched by someone else either.

And on a side note, if you two ever decide to explore this world, I recommend you start with going to a play party as observers only. Make that explicit agreement. You walk in holding hands, you look around, you see the vibe, you talk about what you feel, and you do not play with anyone. Sometimes that alone gives you all the clarity you need.

Trust your gut feeling and your needs. Good luck!

I promise you that there is truly NO question too unhinged for F*ck Around and Find Out with Anna Lee. Have a question you’d like me to answer for the next article? Submit them anonymously here!

Published on November 27, 2025

Words by Anna Lee

Anna Lee is the co-founder and Head of Engineering of Lioness, the women-led sexual wellness company that built the world’s first and only smart vibrator. Anna was previously a mechanical engineer at Amazon, launching the Amazon Dash Button’s original concept and the Kindle Voyage Page Press Technology. She is a Forbes 30 Under 30 alum and has been covered in numerous publications like Fast CompanyGlamour, and Popular Science, as well as Paper Magazine’s Asian Women Creators You Need to Know and Buzzfeed’s 14 Sex Tech Founders Who Are Changing The Way The World Thinks About Sex. Anna is also a prominent sex education creator on TikTok with nearly 400,000 followers. She is a big advocate of expanding understanding and research in sexual health, and destigmatizing female sexuality.