No matter which way you do it, most 69ing is awkward. Different heights, weird angles, and getting too wrapped up in how good you feel that you forget you're supposed to be actually participating — it happens to everyone. Here, six women share their extraordinarily embarrassing 69 stories.
1. "I squirted in his mouth and he told me that I almost drowned him.""I was once hooking up with this guy and he wanted to 69 and I was like, "Uh, OK, sure why not?" So we started really getting into it, and sometimes when I orgasm I have the tendency to squirt. Clearly this guy was not well versed in squirting, and began sputtering and asked if I had 'just peed in his mouth' and exclaimed that I had 'almost drowned him.' Super awkward." —Carrie
2. "I was staring into his butthole and noticed something was coming out of it.""When I was 20, I was making out with my boyfriend and when things heated up, we took a turn down Route 69. I was staring into his butthole and noticed something was coming out of it. I didn't say anything, because there is no polite way of saying, 'Yo, something's up with your butt.' Later, after heavy Googling, I realized that it was hemorrhoids. Like, a lot of them. It was as if his butthole was an '80s music video where Nena was standing inside it just out of sight holding onto a fistful of 99 angry red balloons. We dated way longer than we should have and finally broke up because he got a rare skin infection from only bathing once a week, like a 15th century explorer. Cool." —Cassie, 32
3. "I thought 69 was what I would later learn was Reverse Cowgirl.""When I was in high school, I decided I would wait for the perfect guy to lose my vaginal virginity to, but oral sex was a different story. One time a guy asked me to 69, with me on top. I knew 69 was a sexual term, but I didn't know what it meant. I had seen Body of Evidence with Madonna, so I thought I was better versed in sex than I actually was. I thought 69 was what I would later learn was Reverse Cowgirl and I said, 'No, I'm not ready for that. You know that.' And he said, 'You are OK doing what we have been doing as long as it isn't simultaneous?' I paused and then asked for clarification. He told me he wanted me to sit on his face while going down on him and I was like, 'The closest Madonna got to that was standing on a car while Willem Dafoe ate her out.' And he said, 'Megan, you need to stop comparing your sex life to Madonna's from Body of Evidence.'" —Megan, 34
4. "I finally get my mouth around it at the same time that he hits a really sensitive spot down there, and I bit down. Hard.""So my boyfriend and I are getting it on, kissing and touching each other all over, when he goes down on me. I obviously love it, but I guess he was feeling a little jealous because he suggested that we try 69ing. I said sure, since I'd heard about it and thought it was pretty hot, but neither one of us had ever actually done it. So we get in position with me on top and he starts going to town. Well, I quickly realized that it takes a lot of neck strength to be able to raise and lower at that angle, so after a lot of actually missing his penis with my mouth and it literally bobbing at my face, I finally get my mouth around it at the same time that he hits a really sensitive spot down there, and I bit down. Hard. Around the head of his penis. We haven't 69ed since." —Hannah
5. "Anytime we would 69, all of a sudden I became 'D-Money.'""I was seeing this guy for a few years who happens to be an NBA player (and someone I had known for years). We started dating and it was like magic. Everything was perfect, until it was time to, uh, share the ball. Anytime we would 69, he would start to act like I was a teammate and all of a sudden, I became 'D-Money' as in, 'Yeah, D-Money!' or, 'Let's get it, D-Money.' It's like we were on the court during the Finals trying to finish strong for the win. But the funny part was it was only during our 'double assist' time together that he would do this. Needless to say I had a lovely time addressing the inspirational words of wisdom with him after a few times of pure puzzlement. Oh, and did he try to high-five me after? Obviously. Teamwork makes the dream work." —DJ, 28
6. "We forgot that the window beside the front door looked right into the living room and the lights inside were on, giving his parents a perfect view.""I was 69ing with my boyfriend, in the living room of his parents house (we thought they were out to dinner). Just as we were both finally getting into it we heard the front door start to open and madly scrambled to cover up our dirty deed. However, we forgot that the window beside the front door looked right into the living room and the lights inside were on, giving them a perfect view. His dad later told him it looked like we were really getting busy!" —Lane, 23
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Lane Moore is an award-winning comedian, actor, writer, and musician. She is the creator of the hit comedy show Tinder Live and author of the critically acclaimed book How to Be Alone: If You Want To, and Even If You Don't. Moore is the front person and songwriter in the band It Was Romance, which has been praised everywhere from Pitchfork to Vogue. She has written for The Onion, The New Yorker, and was previously the Sex and Relationships editor at Cosmopolitan.
