4. MILF-schooled (male, 27)
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.
