Search Results: how to bring up sex

I used to make these all the time in Reddit's /r/6perks, but they always whine and b*tch over on Reddit, so... I'm bringing them here! Which one of these would you want as a Winggirl?

1. Marla Rivas is a quintessential city girl in a leather miniskirt with a Mid-Atlantic accent who works as a bartender while pursuing a law degree. She's street smart and savvy to how people work but behind that cool as ice exterior, she's really insecure and it's all a facade.

2. Kessandra/Kesi for short, is the socialite who knows the upper class lifestyle and is your golden ticket into how the elite and super-rich party. She'll connect you with the big wigs. However, she's a bit past her prime and getting a little too old for this sh*t, but can't admit it.

3. Kyung/"K" is the laid-back feminine tomboy who looks pretty, but acts like one of the guys and has some of the filthiest sex jokes you've ever heard. But, she comes from a really racist family who want nothing to do with you and will only hang out with you in secret.

4. Holly, the sweetheart Christian girl-next-door who doesn't like partying, but has a semi-famous rapper brother who's cool and often likes to invite her out to various events and parties. He's generally nice to anyone his sister likes, but you'll never really be in the inner circle of her brother's crowd. Just a "guest."

5. Miami Millie is a whole lot to deal with, and lives the hard rock and roll lifestyle when not doing exotic dancing as a job. She's friends with some of the hottest sex industry workers in town and can hook you up for free, but she's also on the verge of catastrophe with the hard partying she does.

6. Kharisma/Khari is an Indian immigrant pharma grad student and D&D nerd and likes to play board games and card games with friends. She loves superheroes and has a decent size community of nerdy online female friends who live close by. While cute enough for your tastes, Khari is not at all attracted to you as a lesbian.

I asked a question about something similar to this before.

A while ago she told me her and her best friend used to have history and have “fucked around before” (she said didn’t they didn’t have sex but he’s grabbed her boobs and I’m assuming made out or whatever)

and at first I was a little nervous that she’s best friends with a dude she’s done shit with before. But I trust her, and I decided I was being a little insecure due to being cheated on in my last relationship. So I forgot about it.

Today I was walking home with her and we were going back and forth with the little roasts/jokes we do. (We’re both sarcastic people, we’ll poke fun at each other sometimes)
And one it her responses to me was something along the lines of “Okay, I’ll kiss my best friend in front of you”

she was joking around but it was just a joke that was too real for me considering I already had concerns about her being attracted him..

And it was very out of nowhere. I don’t remember what I said but I remember not understanding the correlation of why she would bring him up.

I didn’t get mad at her or anything because I felt it was just something stupid I was overthinking about.
I just get nervous because my ex used to make “jokes” about having a second boyfriend and it turned out to be true...
So am I ignoring red flags or just being insecure?