1. Jerking around in-flight
My college girlfriend had an insatiable appetite for sex. So an hour before heading to the airport to catch a flight to Italy in 2002 (the trip was our graduation gift to ourselves), we had sex. By the time we were boarding, she was already ready for more. Naturally, we checked out the plane’s bathroom, but we agreed that it looked too cramped for a mid-air romp.
Undeterred, my gal summoned a flight attendant shortly after takeoff and requested two blankets. Then she draped the navy blue polyester throws over my lap, slipped her hand beneath the makeshift barrier, withdrew my dick, and massaged me to erection. Bear in mind that we were in a three-seat row. She was by the window, I was in the center, and a middle-aged European dude neither of us knew was sitting near the aisle.
While jerking me off as slowly as possible so as not to raise suspicion, she whispered in my ear that she wanted to make me come. It was odd being shoulder-to-shoulder with a complete stranger, and it wasn’t easy to muffle my increasingly heavy breathing, but it was incredibly hot to do something so daring out in the open. After about half an hour, I came, smiling wide, aware that I would never forget that less-than-innocent hand job.
The Spring Fling concert is a major campus event at my small liberal arts college. So when the famous rapper we’d all been looking forward to seeing for weeks singled me out and pulled me up on stage mid-performance, it was a big deal. Dancing alongside a verified celeb in front of the entire school, I inevitably got a little drunk on my five minutes of spotlight. I decided right then and there that I was DTF (down to fuck).
But what transpired between us wasn’t the wild, disconnected sex I anticipated. To start, the dapper rapper nibbled on my toes. He followed that intimate gesture by caressing my body tenderly all over. Then he told me he could love me, and offered to pay for my college education! The next morning, he invited all my friends out to brunch.
As soon as he left town, the reality that he was twice my age, lived in Atlanta, and traveled constantly set in. When he texted a few days later, I was shocked he hadn’t forgotten me already. My ego begged me to respond. But rather than draw the whole thing out and make myself vulnerable to disappointment, I chose not to taint a precious one-night stand. Hopefully the disappointment didn’t kill him!
3. Suddenly single, seeking sex cure
As soon as my divorce became official a few years back, I took a job working as a television producer that required traveling across the country with the show’s cast and crew. As I interacted with more and more new people for a few days at a time, I formulated a theory: The only way to cleanse my sexual palate of ex-husband residue was to sleep with a total stranger.
I was unwinding at the bar of a cheap, cozy hotel in the middle of America one night when a handsome traveling salesman started flirting with me: The perfectly clichéd opportunity to regain control of my sex life, right? Then I noticed his wedding ring. At the risk of wasting erotic energy, I addressed the issue directly.
“My wife and I have an understanding,” he said.
Upstairs in his hotel room, we stripped off our clothes and attacked each other. We went at it three times in a row, and with each orgasmic round I shed a layer of the post-divorce blues, just as I’d hoped.
The next morning, my healer of a salesman and I woke up to a call from his wife and his guilty tone revealed that his marital “agreement” was probably one-sided. Honestly, though, I didn’t feel bad. I needed to get laid, and I was grateful to be cured.
At 21, I caught an older, beautiful, fit, blonde woman staring at me from across a club in downtown Fort Lauderdale. Soon enough, she asked me to dance. We didn’t hook up that night, but she gave me her number and I pledged not to let the opportunity slip before leaving for school in two weeks.
That Friday night, she scooped me from my parents’ place in an Escalade and drove me to her suburban McMansion, where two other badass cars were parked in the driveway, and, apparently, two young kids were tucked in bed.
“My ex husband’s a baller,” she explained.
I didn’t ask questions.
After the babysitter showed up, my MILF and I headed to the nearest strip club—her choice, not mine. A dozen lap dances later, around 5am, we checked into a hotel. As soon as the door slammed behind us, I started kissing her and fondling her breasts like I would with a woman my age.
“Don’t rush,” she said.
I took the cue. By the time I climbed on top of her, the sun was rising. Finally! I thought. I entered her eagerly, and she moaned loudly. Overwhelmed by the excitement of pleasing an older woman, however, I blew my load in seconds. The upside to being young is that I was erect again in minutes, and I managed to prove myself during round two. On top of checking off an important bucket list item, I learned something about pacing, and redemption.
5. It’s good to give
In my late 20s, I traveled all over Europe with a close girlfriend. It was our last day in Bulgaria when an impressively well-built guy with really thick dark eyebrows walked into our hostel. I was more physically attracted to him than I’d been to anyone in a long time, and after months of backpacking without hooking up, I was downright thirsty for sex. Looking around the tent, I could tell I wasn’t the only interested party. I’m not aggressive by nature, but I knew I had to trample the competition fast—or miss my chance.
Once my target set his bags down, I grabbed him by the arm and ushered him outside. We chatted for two minutes in the dark, during which time I learned two things about him: He was a British-Indian amateur boxer, which explained the toned body, and he was seven years older than I was. That was enough for me to yank his belt off and pull his pants down. Right outside the packed hostel, I gave him a blowjob with more gusto than I’d ever devoted to oral sex. The moment demanded impromptu action, and it was worth it. Who knew it could be so damn satisfying to be so generous?