13 Women Share Their Biggest Sexual Regret (So You Don’t Have To Make The Same Mistakes)

Twenty20, isaiahphoto
Twenty20, isaiahphoto

1. “Tirelessly blowing my first boyfriend without ever asking for head in return. Throwback to when I was young and too insecure to assert myself in bed. Now I won’t sleep with a guy again if he doesn’t go down on me the first time.”

— Marlo, 25

2. “Giving my ex a rim-job. I don’t regret doing it—it was actually super empowering and hot for me, lol—I just regret doing it to him. He was such an insecure little bastard that the next morning, he turns to me and goes, ‘I can’t believe you touched my asshole last night. Gross.’ Sorry you’re too sexually frustrated to admit you actually loved it, babe. Moans like that don’t lie. ;)”

— Nellie, 23

3. “Sleeping with a random guy on vacation without a condom, and then dealing with the anxiety of thinking I had an STD (don’t worry, I don’t) all summer, because I was too scared of the results to get tested in a timely fashion. It was miserable.”

— Simone, 21

4. “Anal.”

— Farah, 20

5. “I definitely didn’t sleep around enough while I was single. Now I’m married, and I fantasize about other men constantly because I didn’t experiment enough while I could without it being considered cheating.”

— Tasha, 29

6. “Drunkenly sleeping with my best friend’s crush in college. She forgave me, but three years later, I still lug around the regret of screwing her over like that for one night of totally mediocre sex.”

— Lucy, 23

7. “The sorry motherfucker I kicked out of my dorm room immediately after he said, ‘I’ve never hooked up with a black girl, but you’re so hot I couldn’t resist.’ Always scan for douchebags before inadvertently taking one home.”

— Valerie, 21

8. “Never actually trying Netflix and chill.”

— Janie, 26

9. “Turning down a threesome with my hot best friend and her ex, who was also hot. I was afraid we’d regret it/that she’d be weird to me afterwards, but we were both too mature to let it fuck up our friendship. It would’ve been wild.”

— Delilah, 22

10. “Trying an open relationship with my long-distance ex-boyfriend. The stress of it eventually broke us up, and the one time I actually took advantage of the arrangement, the sex was incredibly awkward and not pleasurable at all. It just felt wrong. Do not recommend.”

— Sasha, 27

11. “Vegas. It actually would’ve been a fun night of clubbing and debauchery if that Italian hipster hadn’t kicked me out of his hotel room and made me pay for my own cab. He made me pay for the cab because I would’t suck his dick. That fucking cab fare overdrew my bank account. Lesson: Never go to Vegas. And don’t fuck hipsters.”

— Jenna, 23

12. “I regret pretty much every time I had sex till pretty recently. Maybe I’m alone in this, but before I started hooking up with a guy who actually cared about making me come, I was just going through the motions, letting every guy I banged just pump and pump and then finish, clueless of whether or not I was genuinely enjoying it. Meanwhile, I’d be suffocating on the bottom, faking the pleasure of the whole experience. Sex should be fun. Not a chore.”

— Zaida, 22

13. “Honestly, my virginity. It sounds corny, I know, but it’s the truth. I always told myself I’d wait for someone I cared about, but then sophomore year of college came around and I was still a virgin, so I caved and did it with a random guy who had a reputation for screwing anything that moved. The sex was horrible. Thinking of that dude sweating and grunting on top of me makes me want to hurl.”

— Mer, 26 Thought Catalog Logo Mark

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