20 more things I learned from having sex with 20 people

PART 2 bcuz I had more sex and learned more things <3

On July 15th of 2025, I published an article on Substack that would become the story I’m most known for today. It was titled, “20 things I learned from having sex with 20 people.”

The content of this piece is quite self-explanatory, though I opened with an introduction that described my personal experience with body count—being a young, horny teenager and wishing it would be higher than zero, being a slutty adult woman and worrying, is mine too high?

When I first realized that I had slept with 20 people (I hadn’t been actively keeping track, but got curious one night and decided to calculate), it felt like a big number. And a chatty number. I had the lingering sense that the number 20 said a lot about me—behind my back. I pictured it telling all the lower numbers, “she thinks she’s slutty in a fun and free way, but really she’s just easy to get in bed.”

Before this article was published, misogynistic hate was already flooding my Substack. There was a time when a day wouldn’t pass with someone calling me a whore, a sperm bucket, or something a bit more creative but equally offensive. I’m not sure I ever really believed it—but there were times when I certainly worried it was true.

But then I remembered—shit, I’m a sex writer! Thank god I’ve had my fair share of sex, because otherwise I would have literally nothing to talk about or advice to offer! And while I’m at it, body count and virginity both mean nothing, and numbers can’t talk. But I know someone who can. (It’s me. I’m chatty as fuck).

So, I shared 20 things I learned from having sex with 20 people. Some were quite meaningful to me, “1. Sex isn’t supposed to hurt. Like, at all.” Others were less serious but equally valuable, “6. The key to the best blowjob comes from Ms. Frizzle.” But together, they caught people’s attention.

The story garnered over 400k views, 13k likes, and 500 comments with incredibly mixed feedback. Lots of men still called me a whore, some people were concerned for the state of the world, and others complained about my use of the word “incel” (probably incels).

For a while, I studied this story, wondering why it performed so well (even though my Substack was and probably always will be 2% strategy, 98% vibes). Was it because it was polarizing? Did the headline feel like clickbait? Did people like to hate on it?

But as I dove deeper in the comments, the outpouring of positivity was unmistakable. And what I loved most—which made me pinch myself with glee—was that people, especially women, seemed to find the story helpful. It sounds simple. But it was legitimately my dream come true.

Someone named Rachael De Marchi commented, “Honestly healing to read. This gives me hope for when I get back on the horse again.”

Nina Barufaldi replied, “Thank you. I just sent this to my daughter.” Arlene Phillips Montalvo said, “I’ll be sharing this with my nieces. I think all young women need to read this.” I couldn’t ask for anything more. That is exactly why I started Railed, and it’s these women and the supportive new subscribers I gained from that story that have truly propelled Railed into what it is now: legit (?).

With that, I sit here a year later, ready to publish Part 2—20 more things I’ve learned from having sex with 20 people. I didn’t have sex with 20 more people, but I do have 20 more things to share. My body count has increased a bit since Part 1, but it hasn’t gone up by 10 and I feel like something like 24 things doesn’t have a good ring to it.

So, whatever. I had sex with more people and learned more things and remembered past lessons and I hope that you find this helpful and worthy of your nieces groupchat <3

---

20 more things I learned from having sex with 20 people

1. You have to try really hard to not get sexually assaulted. Sorry for starting off so incredibly strong, but this is maybe my number 1 takeaway from all my experiences. Sexual assault is so nuanced and can happen to so many degrees, and it is very easy to find yourself in uncomfortable or icky situations (maybe you don’t even realize it’s uncomfortable until after!!). I’m not saying this to scare you, but to remind you that sex is casual and fun but also serious and should be handled with care. With every experience, make sure to check in with yourself and confirm you feel safe and happy.

2. While we’re at it, the most important word you need to learn to say during sex is “STOP.” In the moment, it can be shockingly hard to actually use this word. If you think the other person is enjoying it, or you don’t want to make them feel bad, you might just let it keep going despite feeling pain or discomfort (I used to do this a lot!! Don’t be like me!!). But once you learn how to say “STOP,” you’ll never go back. Sex is hurting? STOP! You changed your mind? STOP! You’re having a great time but just want a break? STOP! I’ve found that other words can be misconstrued for pleasure. But STOP is loud and clear.

3. You never have to go on top again if you don’t want to. I honestly just don’t love going on top. It’s not for me. I just stopped doing it. Turns out, no one cared!

4. Eye contact is everything during sex. It might feel weird at first, but it’s the biggest game changer. It makes you feel so much more connected—which in turn makes everything 10 times hotter.

5. Orgasming fast isn’t embarrassing. I love when a guy orgasms fast. I’m like, yay!! So glad that you loved that!! Now go down on me!!

6. Missionary is the best sex position. First of all, it has so much variety. Legs up! Legs down! One leg up! Sort of sitting up! Trust me, there’s no need to ever do a split on his dick (unless you’re dying to do a clam slam) when the old reliable is there. Why fix what isn’t broken!

7. The best sex doesn’t last super long. The narrative that the best penetration is the one that lasts infinitely is so false. Maybe that’s true for men, but not women. Like, whose vagina is staying wet for a full hour? Not moi! I decree that the best sex consists of lengthy foreplay, quick penetration, and some good head to end the session.

8. The best penises aren’t the biggest ones. Bigger penises can be flashy and fun, but when it comes down to it, they aren’t nearly as practical—and pleasurable, in my opinion. This is more false advertising from the patriarchy who want to disguise their secret desires as ours, when in reality, it’s just another narrative that promotes painful sex for women. (I wrote about this more in depth for Playboy! See: In Celebration of Small Dicks and Short Sex.)

9. Just because you can have sex with someone doesn’t mean you should. My Costar actually said this to me and basically read me to filth. It should be common knowledge but it’s really not in this household. Just because the opportunity presents itself doesn’t mean you have to take it! You’re probably not missing out! (PS I’m freaking out that this screenshot was taken at 11:11)

10. The best blowjob comes from someone who is excited to be doing it. One of my most-asked questions is “how do I give a good blow job?” While we can talk through the bells and whistles at nauseum, I stand by the fact that if you want to give a fantastic blowjob, you need to want to be doing it—which means have fun, play around, share your moans, and make it clear that you’re feeling it just as much as the other person. If you’re sucking their balls and thinking it’s super disgusting, they can probably tell. So, if you find it gross, don’t do it! If you like doing it, let that show!

11. You might get attached to the first person you have sex with. Even though virginity is a social construct, feeling close to your first is a real phenomenon. You don’t have to pick your one true love, but do try to pick someone who feels safe—someone you wouldn’t mind being sort of irrationally obsessed with for a period of time.

12. Orgasm pressure ruins even the best sex. Even though it’s fun when people orgasm, feeling the pressure to do so is the biggest vibe killer—and a surefire way to make sure no one finishes. Personally, I like to let new partners know beforehand that I can have trouble orgasming, but that doesn’t mean I’m not having a great time. That way, I can enjoy the moment and not stress either way! I would highly recommend this strategy for women or men who struggle with the same thing.

13. Republicans actually might be worse at sex. I’m convinced this is legit. They don’t respect women or our bodies, so how could they bang us just as well? And in my personal experience, conservative men can be less good at practicing consent and reading body language. Not to say that liberal men can’t also be guilty of this, but we gotta go with the odds!

14. It’s not rude to use sex toys. It’s actually super hot. If a guy thinks it’s weird that you want to incorporate your vibrator into sex, he is probably insecure about his dick being replaced. But it’s not about replacing, it’s about elevating.

15. Never decide ~in advance~ that you want to have sex with someone. Then you end up having icky sex with a random Hinge date where your tummy hurts but you previously decided you wanted to have sex tonight so you did it anyway. Always decide in the moment (or at least closer to the moment)!

16. You can have safe, communicative sex with a one night stand. While a random hookup can get a reputation for being messy, drunk, and uncomfortable, you can totally have a consensual, communicative bang with a one time thing. That’s not reserved for relationship sex!!

17. You can also have unsafe, uncommunicative sex with a long-time partner. Don’t let things slide just because they’re your boyfriend! All sex should be good, safe, comfy sex, no matter who it’s with!!

18. Sexual chemistry CAN improve. You’re not doomed if the first time isn’t great. Sometimes it takes a minute for two people to find their footing! This isn’t fake!! It happened to me before where it was only okay and then got to be amazingggg over time.

19. But sometimes you can be in love and just have bad sexual chemistry. It’s not always there. Maybe it’s an underlying issue, maybe it’s not. I tend to think this is your body telling you that this isn’t your person.

20. Butt stuff isn’t just enjoyable for men. I included this on my last list, but I think it’s worth repeating. I may still be an anal virgin (not by choice), but a finger in the butt does wonders for female pleasure! Who would’ve thought?