“WHEN HARRY MET SALLY” - COLUMBIA PICTURES
You’re out to brunch with your girlfriends, how long does it take for the conversation to turn to sex? Not long, amiright? It’s not just the ladies on “Sex and The City” who love to talk about sex—it’s most of us. We talk about it with our friends, our partners, and depending on how self-conscious you may feel, complete strangers. We talk about our true sex stories wether it be the amazing sex we’ve had, the comical, the sometimes strange and unusual, and even the not-so-great sex.
For many of us, we learned more about sex from our friends than we did from our parents or sex education class. It’s fun to share our sex stories—if it wasn’t, there wouldn’t be live storytelling shows, podcasts, books, TV shows, or movies. Fantasy has its place, but the stories that resonate the most with us are the true stories, those that actually happened.
I AM & CO put the word out that we were looking for true sex stories and we received a very diverse response; stories from various sexual preferences, practices, and levels of sexual experience. All of these true sex stories are ones you have to read to believe.
12 True Sex Stories Guaranteed to Raise Eyebrows
“Not Friends, No Benefit”
Comedian Shalewa Sharpe, creator of "So You Just Out Here?"
I ran into my one-night-stand guy at the club. Now, some people might call that a “friend with
benefits” but that term suggests that the two parties are friendly enough to schedule a benefit.
This guy and I were not friends. Our benefits only happened if we ran into each other at the
club. So, we made out for a minute, then he suggested we take this party to my car. This
was how I ended up parked behind a grocery store, attempting to have sex with this guy in my
1988 Honda Prelude—a sports coupe, with bucket seats. Have you had sex in bucket seats? If
so, a follow-up question: are you double jointed?
The guy and I struggled for a bit, then his face fell. “Oh, this sucks,” he moaned. “It’s because my dick’s too small.” I had to console this guy while also keeping an eye out for the cops. If you find yourself in this predicament, don’t end up saying what I said: “Hey man, we’re in bucket seats—this ain’t gonna be easy.” A real mood-killer. We threw in the towel, I dropped him off back at the club and went home. Later that night, my roommate, who was the club’s doorperson, mentioned that she saw the guy with a weeping woman at the end of the night—they were walking in circles around the parking lot, then they hopped on his motorcycle and split.
The next day, as I was furiously scrubbing and vacuuming my car, I found a driver’s license for
a young woman wedged between the front passenger seat and the middle console. I guess it
fell out of one-night-stand guy’s pocket during the, uh, festivities. I scratched out the ID’s info,
punched a hole in it, and hung it on my rearview mirror as a cautionary tale.
“It’s Part Of It”
Jason, Columbus, Ohio
We were both in college and had been dating for a while when she decided to take it to the next level.
“Tie me up,” she demanded.
“Okay, um, I’m going to tie you up now,” I said and went to get some scarves that were conveniently strewn about and set to work.
“No!”
“Oh, my God! I’m so sorry! I thought that…” and I began to loosen the bonds.
“No, it’s part of what makes it so hot.”
“Oh, right,” I said and went back to doing Boy Scout knots such as the square knot and the sheepshank. I wondered if I should go with the trucker’s hitch? Nah. Too much.
“I’m going to f*ck you now,” I said getting into it.
“Let me go!”
I immediately stop what I’m doing.
“Oh my God, I am an idiot. I am so sorry. I didn’t understand. You see, when you said you wanted, what I thought was, but in reality, I see… Oh no, I’m so sorry.” I quickly start to untie all the knots.
“No, it’s part of it.”
“What Goes Around, Comes Around”
Ashley, Raleigh, North Carolina
I paid my boyfriend for sex the first summer we were together…11 years later, he’s paying me for sex.
“The Hook-Up Room”
Comedian Anita Flores, host of I'm Listening: A Frasier Podcast with Anita Flores.
I’m at my first high- school party, and it’s not going well. Between my social anxiety and the fact that I only know the host, all I can think about is how I’m going to escape. I can’t actually leave, or else I’ll seem “uncool.” Fortunately, I come up with the next best solution. After making some light small talk with the host (Cassie) about her impressive selection of snacks, I ask, “Is there anywhere I can take a nap?” At the time, this seemed like a normal way to still be at the party without having to speak to anyone. I can’t say that Cassie agreed. After a long pause, she replied, “Uh, I guess in my attic.”
I gleefully head to the attic. All the lights are off and it’s strangely warm, but it beats talking to people. I feel around and discover a futon I can pretend to sleep on. There I am lying down when something round and muscular attacks my face. It’s a butt, and it's smothering me! Ever want to suffocate someone, but don’t have a pillow? Just wear thick, non-breathable polyester pants. I hear a low voice. It’s a boy butt. He hears my muffled cries, gets up and exclaims, “Whoa, sorry dude!”
Now there’s giggling. He’s with a girl. Suddenly, I hear what sounds like a lot of teens slurping soup. There are more people in this room than I realized. Cassie sent me to take a nap in “the hook-up room!” Picture “Eyes Wide Shut: The Early Years.” Before the masks, there were braces. By this time, the boy butt and his lady friend have taken the futon from me. I'm standing there feeling left out because no one has asked me to join in. I can’t run away, otherwise, everyone will think I’m a prude! So, I find an empty loveseat, plop down, and close my eyes. Because there’s nothing cooler than ignoring sex. I’ll make sure to tell my future teen daughter that, too.
“There Are Rules”
Michael, Portland, Oregon
I was sessioning with a dominatrix named Vixen when her friend Wendy came over. Vixen blindfolded me and put me in the corner, which I was more than okay with. The minute Vixen’s back was turned, I took off the blindfold, even though I knew (and hoped,) I’d be punished. Vixen took out a strap on from her toy-cupboard and proceeded to f*ck Wendy with it. It was quite a show and later, I was punished severely for watching—it was well worth the tribute that I paid Vixen.
“Don’t Stop Under Any Circumstances!”
Carrie, Chicago, Illinois
My boyfriend and I were having sex one night on my old as hell bed. He was an ex-professional football player and I’m a big girl, so it shouldn’t have been surprising that right when things were getting super intense, the bed broke. He stopped what he was doing, so I yelled, “Don’t stop! I’m so close!” Without moving from the now broken bed, we get back at it and this time we don’t stop until we both cum. If there had been an earthquake or a tornado, I would have made him keep going then, too.
“Side Effects Can Be Embarrassing”
Krysta, Orlando, Florida
I've never been really big into taking birth control, but a coworker of mine mentioned that she was on a pill where she only had a period every three months... I wanted in on that! So, I went to my doctor and got on birth control. I started dating this new guy, who was literally the sexiest human-created. Around him, I tried to be Miss Perfection. Meanwhile, I'm on these new birth control pills and the doctor forgot to mention that they had lactose in them. I'm extremely lactose intolerant, even the smallest bit gives me major gas.
The first time the perfect guy and I had sex was a disaster. Every thrust he made inside of me made me pass gas. It was so embarrassing. We literally had to stop and go to Walgreens to get me some type of gas pills because he and I both couldn't take the noise, let alone the smell. Let's just say, I stopped taking those pills immediately.
“Sex On The Deserted Beach”
Beverly, New York City
My partner and I were having a romantic vacation for my birthday in Newport, Rhode Island, and decided to spice things up by making love on a (deserted) beach in the middle of the night. Unfortunately, this beach was not quite as deserted or private as we had initially anticipated. All of a sudden we saw flashes of bright light, immediately stopped, and became alarmed.
A police officer arrived, trying to hold back a grin, and asked us if we'd seen some "kids swimming" after hours. We said no, he left, and we quickly packed up our things to make a quick exit. We drove home laughing not quite knowing what to make of the experience, but it certainly was a bonding one. It's definitely an evening and birthday I won't soon forget.
“Don’t Disturb Grandpa”
Spencer, Phoenix
I hooked-up once with this guy who was taking care of his grandpa. It was around 10:00 p.m. by the time I got to his house. Whispering, he asked me to follow him and to not make any noise, his grandpa was watching TV in the living room. The guy sneaked me into a bedroom, but I guess that wasn’t soundproof enough, so we went into the closet and had very cramped and uncomfortable sex in there. I don’t think his grandpa had any idea about what was going on.
“Male High Club”
Reynaldo, San Diego, California
I was taking a night flight home from Hawaii, as I was sitting down, I turned to see a guy who was so handsome I was stunned. Like a lot of us, he wore shorts and Aloha shirts, but he was well-built and looked more like he’d be a lead on one of those Hawaii detective shows. There was an empty seat near me on the aisle, and the guy asked if he could sit there to stretch out his legs. Other than nodding yes, we didn’t talk. The man grazed my knee with his leg, and all the hairs on my leg stood on end. And he didn’t pull away right away, just gradually. He got up to get a blanket from the overhead compartment which he placed over his legs.
With no talking at all, he made the slightest gesture to offer me some of the blanket. Before you know it, the blanket was spread over both our legs. Then, our hands somehow started to find each other. And for a long time on the flight, that was it…just our hands grasping together, coming loose, rejoining, stroking fingers. I couldn’t believe this was happening. I was rock hard. And gradually, very gradually, all without talking and with this stud of a guy who I did not know at all, our hands gradually started to stroke each other’s thighs, mirroring each other.
And eventually, very discreetly to not get attention or show movement above the blanket, we each found our erections extending out through the bottom of our shorts, and we grabbed each other. Eventually, some napkins or handkerchiefs were brought below, and without making any sound, we both came, and it was pretty simultaneous.
“Kung Fu Fighting”
Carol Gee, Author, “Random Notes ( About Life. "Stuff"And Finally Learning To Exhale)”
A romantic, I fantasized about what it would be like to have sex on satin sheets. My fantasy materialized when my husband and I, two young Air Force sergeants returning from living in the Far East, stopped to visit another Air Force friend and his lady in San Francisco. Invited to spend the night, the lady made the guest room bed up with a brand new pair of red satin sheets. How did she know my fantasy? I couldn’t wait to get my husband in bed to enjoy sex so good that the neighbors in the apartment next door would have needed a cigarette.
I took a shower, smoothed on scented body lotion and got into bed. My husband was already in it waiting for me. On those satin sheets, our lovemaking suddenly morphed into Kung Fu fighting. Taking me into his arms I accidentally poked him in the ribs. Oof! Climbing on top of him I kneed in the thigh. Ouch! Attempting to kiss him I missed his mouth and ended up rubbing noses with him. Then his pillow slid off the bed, mine quickly followed. Instead of holding onto him, I held tightly to the bedsheets trying not to slide off, taking him with me. Not only was the whole thing a disaster, but we also got very little sleep that night for trying to stay in the middle of the bed. Frankly, I'm glad those sheets weren’t mine as they would most likely have ended up as pretty red curtains.
“Girl/Girl Love Lesson”
Sensual Massage Therapist, Jazmin Light
The streets of Zurich were empty as I headed toward their place. The gentleman on the phone had asked me if I would "be" with his girlfriend—while he watched. He said she wanted a woman to show him "what women like." The World Cup soccer games were on, and that night, Switzerland was playing. The air bristled with excitement. All anyone talked about was "Fussball." Everyone's windows were wide open due to the summer heat.
A classy-looking man in his mid-fifties opened the door to a modern loft apartment. Surprised, I wondered, “Shouldn't he know what women like by now?” Behind him, pouring champagne at the high-top table, stood Nadia, perhaps thirty years his junior. In her red La Perla lingerie and matching stilettos. She handed me a glass and kissed me on the mouth. We made a toast. I took a sip, then lifted Nadia's silky blonde hair and kissed her neck. I let my lips and teeth linger, then gave her a soft bite. She gasped.
Suddenly, a roar of voices sailed in through our window and engulfed us. "YAAAAAY!!!” The cheering came from next door, from above us, below us, and from outside. “GOAL!” We laughed as the ruckus died down. I stroked Nadia's hair, neck, and torso. "There are endless ways to please a woman, Manfred," I said, twirling my fingers on her lacy bra cups.
Manfred plopped down on the bed and stared at us, his mouth open. I unsnapped her bra, returning his gaze. "There's much more to women then nipples and—" I slid my hand to her panties, "pearls." Nadia inhaled sharply. "So slow down, savor, discover, and—play!" Nadia groaned, Manfred grinned. New shrieks and cheers exploded throughout the neighborhood.
***
When you share a sex story, it can help you to connect with other people, learn about yourself and others, and it can inspire you to try new things. As humans, we’re always growing and that includes our sexuality.
Sex is part of the human experience and it’s always fun to hear someone else’s stories of incredible sex, confusing sex, or way-out-there sex.
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