Revealed!! Your Most Embarrassing Sex Stories

Sex is a lot like life, isn’t it? Things never really go as planned.

Published December 28, 2020

Esther Aarts

My first-ever kiss was a total disaster. At 12 years old, I had no desire to kiss the boy I was “going out” with, but an unexpected game of truth or dare left me feeling like I had no choice but to pucker up. When he went in for the kill, I was shocked and unprepared. In a moment of vulnerability and in an effort to protect my personal space and boundaries, I pushed him off of me, screamed “Ewww, gross” and aggressively wiped my mouth off with the back of my hand. Needless to say, he dumped me the next day. My first experience of physical intimacy with a boy left me humiliated for months, and I swore I would never kiss again.

Whether it’s a first kiss, your 12,000th time having sex or a nonsexual moment of closeness, intimacy requires vulnerability, self-love and acceptance; it requires the ability to roll with the unexpected punches, which we are likely to find. Intimate moments lend themselves to embarrassment because we are vulnerable in these moments. Furthermore, we often carry unrealistic expectations for ourselves.

Megwyn White, clinical sexologist and director of education at Satisfyer, points out that in the case of sexual encounters “we’re conditioned to think that all sex not only needs to be good, but also [needs to] meet the ridiculous standards of an airbrushed world.”

This expectation is obviously unrealistic. Sometimes, intimate moments are awkward and embarrassing, and can even feel humiliating. And while it is probably impossible to prepare for these awkward moments, it is possible to get through by embracing them as moments of connection. White says that these moments “invite us to embrace our human nature … [and] witness each other in the multiplicity of our expression.” We can remind ourselves that if we have dared to get close to others, then we likely have an embarrassing story or two of our own. Hopefully we’ve learned to look back and laugh at these stories —as is the case with the individuals who shared their stories, below.

A case of mistaken identity

“I was grocery shopping with my girlfriend when I lost her in Walmart. She had my wallet [so I had to find her before I could pay]. I saw her figure, thanks to her distinctive yoga pants. She was busy rummaging for something on the shelves and I slapped her bottom really hard only to find out it was another lady. I ended up getting kicked out of Walmart that day.” — James, 29, California

A breathtaking encounter

“I was having sex with a partner and our rhythm got out of sync and his forehead connected with my nose — there was an almighty crack and he asked if I was OK. I thought I was, so we kept going. The next day I had two black eyes and couldn’t breathe through my nose — I had broken my nose and needed surgery to repair it.” — Lori Beth, 57, United Kingdom

Grooming gone wrong

“[In preparation for my first time, a few friends] told me that I should do some “pruning” down under, but no one prepared me for the devastating razor burn that resulted. When my boyfriend got a good look at my landscaping job, he immediately froze. He stopped everything and tried to get us to watch a movie instead, but I was too upset to stick around. I had him drive me home and was promptly ghosted. Years later, I ran into my failed-first at the grocery store and ambushed him with the giant WTF I had been waiting to ask since this traumatizing event occurred. He [said he] had seen my admittedly horrific razor burn and thought I had some sort of STI.” — Anna, 43, Massachusetts

Too hot to handle

“I had just started [to embrace my sexuality], so I made some purchases. Nothing too raunchy, just a readily available supply of condoms and some lube to make things go smoother (pun intended). The lube ended up everywhere and we had a bit of fun [until] my lips started to burn, my tongue felt thick and heavy in my mouth, and the need to breathe became a bigger priority than sexy time. Long story short, my partner rushed me to the emergency room, where a whole host of medical personnel got to learn my embarrassing blunder while my potential lover fretted over whether or not he had inadvertently killed me with his you-know-what.” — Katrina, 33, Arizona

A slip of the tongue

“One time a man complimented my breasts during sex and said, ‘You don’t know how perfect these are.’ And I said, ‘Thanks, I got them from my mom.’ — Morgan, 20, New York

Caught in the act

“My husband and I lived overseas and were visiting my parents’ home as young newlyweds. We retired to our room for the night, but we hadn’t planned to go to sleep right away. My mom surprised us by popping her head in the door to say goodnight. We were (fortunately) covered. My husband was hovering over me while I pretended to be sound asleep. Made him look super creepy!” — Maryanne, 46, Connecticut

Sex is a lot like life, isn’t it? Things never really go as planned; there are good times and bad, tears and laughter, mistakes and solutions; and there is always so much more to learn. White says, “Sex is something that is a lifelong learning process. No matter how many times you’ve done it there are always new things to learn. Avoid fixating on your performance and instead tune into what you’re learning about yourself and your partner.” Remember that moments of intimacy call for us to relate with vulnerability, self-love and acceptance, and from this place to witness and accept our variety of expressions, as well as those of our partners. Humor helps. And don’t forget to go to the ER if needed!

Suzanne E. Hayes is a freelance writer based in Simsbury, Connecticut, where she’s raising three children and finding plenty of real-life inspiration along the way. Her work explores family, identity, and the beautifully messy moments of modern womanhood. Suzanne’s writing has appeared in Working Mother, Woman’s World, Kveller, Guideposts, Under the Gum Tree Literary Magazine, and more. With honesty and heart, she brings stories to life that resonate long after the last line is read.