The best:
Age 20 (of course) and my second girlfriend who was 32 at the time. Kind of a Mrs. Robinson thing, a waitress and single mother of two who worked at the restaurant where I washed dishes while home from college over the summer. Sexy lean body, Mediterranean ancestry so always tan, and she was the tightest juiciest snatch I've ever been in before or since, bar none. Even she said we fit well together. The best part: she'd had a hysterectomy so I was in condom free hog heaven. The first time we fucked we came at the same time together. It was always the same location and time - the back seat of the family station wagon parked behind the restaurant after closing, typically around 2AM. I knocked the bottom out of that ass the whole summer.
The best-worst:
Make-up sex with another ex that resulted in her becoming pregnant. This was deep into our 40s. She still looked great - pretty face, about a 7/8, huge rack, big beautiful derriere (I like that , not sure why) and she knew how to dress right, another weakness of mine. We did the traditional mutually respectful classy dinner date, you know "to talk over things." Coat and tie, nice steak dinner at an old school club, couple of drinks, then back to my place, again to "talk." She had been rubbing up against me the whole night, sitting next to me with no air gap, touching me on the arm, the textbook run of womanly wiles. By the time we sat down on my couch I was rock hard - that kind of occasional hardness that is so hard, it's actually painful. The proverbial blue-veiner (side topic: is there a female equivalent to this?). No Viagra involved either. An all-natural female induced boner.
We kissed. She noticed the Washington Monument in my pants and actually used the famous Mae West line, "Is that a gun in your pocket, or are you just happy to see me?" Game on. To the bedroom, strip, dive into bed, oral on her to climax, then missionary and I came in about 45 seconds. No condom, she'd been on the pill for years.
I had viewed it as more of a hook-up than a reconciliation and she got a little pissed the next morning. I knew I didn't want to date her, and I admitted I just wanted to fuck her - and potentially become friends with benefits - because well, she was a fantastic lay. That didn't go over well.
Six weeks later, I got the "phone call." Of course, knowing she was kind of a 'popular girl' and had more than one male acquaintance at the time, I immediately lawyered up. Thankfully, six weeks after that I got the other phone call, where she told me she'd had a miscarriage (expected by her doctor, given her age and fibroids, so she said).
False pregnancy mind fuck as pay-back for using her (trust me, the using was waaay more deserved than the pay-back)? Possibly. Friends advised me as much. But maybe not. Anyway, that was six weeks of hell I never, ever want to relive. Great sex for 45 seconds, then a potential lifetime of regret, and certain financial ruin. All at the hands of a cunty, spiteful woman.
Be forewarned boys: Act in haste, repent at leisure. Wrap it up (and flush it afterward), or get a vasectomy. And never fuck a Catholic woman you don't wish to knock up. Be in charge, be in control. Always.
Honorable mention: handjob from a certain masseuse with a Mt. Rushmore size rack. Somehow this gal would incorporate those fun bags into The Finish and I would spout a geyser I never thought possible. Thanks Rhonda!