5 Sex’perts Share Their Funniest Sex Stories

  • Jan 19, 2026

5 Sex’perts Share Their Funniest Sex Stories

4 Sex'perts share their most hilarious and mortifying bedroom moments—from hammock crashes to disappearing toys. Laughter is the best aphrodisiac.
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When was the last time you laughed during sex?

Not a polite chuckle, I mean a full-on, snort-laugh, tears-streaming-down-your-face kind of laugh where you have to pause and catch your breath.

If you can’t remember, you’re not alone.

Somewhere along the way, sex got serious. It became about performance, technique, and doing everything “right.” And while there’s nothing wrong with being intentional about pleasure, we’ve lost something important along the way:

Sex is supposed to be playful, messy, and yes, FUNNY.

So I asked four leading Sex’perts to share their most awkward, hilarious, and slightly mortifying sex stories. Because the truth is the best sex lives aren’t the ones where everything goes perfectly. They’re the ones where couples can laugh when things go hilariously wrong.

Want more ways to improve your intimacy? Check out our sex’pert advice for having the best sex this year.

Trust me, you don’t want to miss the last story. Get ready to laugh, cringe, and maybe feel a little better about your own awkward moments.

Teledildonics: A New Sexual Frontier

Susan Bratton, bestselling author and CEO of Personal Life Media—known as the “Intimacy Expert to Millions”—doesn’t share an awkward moment. Instead, she shares something that blew her mind in the best possible way.

Susan and her boyfriend recently experimented with synchronized sex tech. A wand called the Pearl 3 for her, and a Kion stroker for him. The twist? They were app-controlled and mirrored each other’s sensations.

“We laid side by side and he had the app that controlled the stroking on him while I had this inside me and he controlled it and they were mirroring each other. So what was happening to him was happening to me.”

When it stroked the tip of him, she felt it deep inside her. For 15 to 20 minutes, she experienced his pleasure journey, complete with valleys, hills, cliffs, and side trips.

“I never had an experience like that before, even when I would use a pleasure tool on myself or even in partnered play. It was the most incredible experience.”

Susan is currently exploring haptics and teledildonics (remote pleasuring for couples), products made by Kiiroo. Who knew the future of intimacy would be so... synchronized?

The Hammock Incident (and Other Adventures)

Kevin Anthony—a Certified Sexologist, Tantra Counselor, and host of The Love Lab Podcast—has multiple stories. And honestly? That tracks for someone who’s made it their life’s work to explore sexuality.

“At this point in my life I’ve had a fair amount of sex and I’ve tried a lot of things especially doing what I do for a living. I’m a bit more open than most people into trying new things and they don’t always work well and you end up with some awkward stories.”

Story #1: The Hammock Crash

Picture Kevin and his girlfriend, in her finished basement, getting it on in a hammock. Everything’s going great until…

“All of a sudden the rope that is holding it to the ceiling breaks and we go crashing to the floor with her on top of me, still with me still inside of her.”

They hit the floor and immediately burst out laughing. Kevin’s solution? “I think I should be the one to rehang this hammock up from the rafters.”

Story #2: The Disappearing Anal Beads

Years later, with a different partner, Kevin learned an important lesson about sex toy shopping. They bought anal beads from a sex toy store without really knowing what to look for. Everything was going well until, wait a minute, where did they go?

His partner was mortified as Kevin had to, shall we say, embark on a retrieval mission.

The lesson? Choose anal beads with a big ring handle, not a tiny one. You know, so they can’t disappear during really pleasurable moments.

Story #3: The Sex Party That Wasn’t

Kevin once attended a sex party where the host asked people to share something deep and emotional as an icebreaker. Noble idea, terrible execution.

“For whatever reason, people shared these really deep, dark things. Like some of these things, I was like, I can’t even believe you said that in front of a crowd of people.”

The oversharing killed the vibe so completely that the rest of the night, everyone just laid around stroking and cuddling each other. At a sex party with dozens of people, exactly one couple had sex. Everyone else was too emotionally drained.

Kevin’s takeaway? “In the immortal words of Larry Flint, relax, it’s just sex. Have fun with it. Try stuff. Some of it’s gonna work, some of it’s not gonna work.”

The Underwear Discovery

Dr. Laurie Mintz, bestselling author of Becoming Cliterate, therapist, and emeritus professor, has a college story that her friends will never let her forget.

These days, nothing can embarrass a sex therapist who’s been in a monogamous relationship for 43 years. But college Laurie? That’s a different story.

The setup: Laurie had a long-term boyfriend on a term abroad. They both promised to stay faithful.

“We both said we would stay faithful. Neither of us did, okay? We were in college. We were not as mature. We were horny, whatever.”

So she slept with someone else. Fine. Then she slept with another person. Also fine, until this person noticed something at the bottom of her bed.

They pulled up a pair of men’s underwear. “Who’s are these?”

Panicked, Laurie said they belonged to Sam, her boyfriend who was abroad.

Their response? “Does that mean you haven’t changed your sheets in four months?”

Busted. She had to laugh and confess they were actually from last week and belonged to someone else entirely.

This story has been retold at every reunion since. Her friends still joke, “Remember when so-and-so pulled so-and-so’s underwear out of your bed and you first tried to lie about it?”

Dr. Laurie’s takeaway? Some embarrassing moments live forever—but at least now they’re funny.

The Anal Sex Reality Check

Amy Rowan, The Suburban Sexologist and founder of Suburban Intimacy, tackles the topic everyone worries about but nobody wants to discuss: what happens when anal sex doesn’t go as planned.

Amy and her husband had talked about trying anal sex for a long time. They prepared properly. They got the right silicone lubricant, communicated, took things slow. Everything was going well until... the thing she’d been most afraid of happened.

“The worst case scenario happened. And a little bit of poop came out, maybe more. I’m not sure. I’m not quite sure how much it was, but I could smell it, which immediately sent me into like, oh my gosh, this is awful. We have to stop.”

Her husband’s response? “It’s fine, it happens. This is just part of it.”

But here’s what made all the difference. He was prepared. He had baby wipes ready, quickly cleaned up, flipped the towel, and said, “We’re having great sex. Sex is messy.”

Amy admits it took her a bit to recover emotionally, but they were able to finish and have a good time. Still, it was a while before they tried again.

Her practical advice? Do a fleet enema beforehand if you’re worried. Have towels and wipes ready. Use the right lubricant. With proper preparation, it can be a pleasurable experience, even if you’re someone (like Amy, a sexologist!) who still cares about these things.

“When you prepare properly, make sure you have some towels, make sure you have some wipes handy, make sure you have the right lubricant, do an enema if it’s something that really concerns you... then with the right preparation, it can be a very, very pleasurable fun experience for both partners.”

The real lesson? A supportive partner who says “sex is messy” makes all the awkward moments survivable.

The Real Story Behind The Stories

Here’s what these four stories teach us:

1. Sex is messy—literally and figuratively. Hammocks break. Things get lost. Bodies do unexpected things. And that’s okay!

2. Laughter is part of intimacy. The couples who can laugh together during these moments? They’re the ones who stay together.

3. Preparation helps. Whether it’s reinforcing that hammock, choosing toys with proper handles, or having baby wipes handy, a little planning goes a long way.

4. Communication saves the day. Amy’s husband’s response to a mortifying moment? “It’s fine. Sex is messy.” That’s partnership.

The best sex lives aren’t the ones where everything goes perfectly. They’re the ones where couples can try new things, laugh when things go wrong, and keep showing up for each other with curiosity and grace.

Speaking of Stories That’ll Make You Blush...

the-taboo-show-book-cover

If you enjoyed those messy, hilarious, very real stories about sex… you’re going to want this on your radar.

The Taboo Show is my upcoming novel, officially launching February 14, 2026.

It follows four women who walk into a sex show and walk out with their lives completely turned upside down. Expect friendship, secrets, laughter, and the kind of uncomfortable honesty that makes you text your friends at 2am like, “OMG you need to read this.”

Fair warning! your book club will have opinions.
The good kind.

And here’s the fun part. Pre-order before February 13th and you’re automatically entered to win a $550+ pleasure gift bundle. Yes, really. And yes, it’s very worth it.

Pre-Order The Taboo Show →

Because the best stories aren’t just entertaining. They make you laugh, squirm, and rethink everything you thought you knew about pleasure.

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