I'm in my forties now and seem to be finally settled down somewhat with a passionate wife and a young healthy son and daughter. But when I think back to all the true loves and tempestuous affairs and quick flings with strangers I've had, I'm relieved to find I don't truly regret any of my sexual adventures. Oh sure, I've woken up next to more than my share of women that didn't look half as beautiful or seem a quarter as interesting as the night before. And I usually made some lame excuse and slinked off with no intention of ever seeing that person again. But I'd rather have ended up there than have gone home early that night or played it safe and careful. As my Grandfather told me once: “The worst pussy I ever had...wasn't half-bad.” That's my Grandpappy, passing his wisdom on to the next generation. I can't wait to tell my grandkids about all my favorite liaisons from my checkered career. Now, I'm not really one to keep score, or brag about my conquests, or favor quantity over quality. But I will brag now that I've bagged well over a hundred chicks. Stuffed 'em like turkeys. Parked my big yogurt truck in their garages. Done the horizontal tango. Rogered them furiously. Shagged them silly. Tossed their salads. And they've all wanted more. Yeah, I know. For many guys, a hundred notches on their proud member is no big deal. But you have to understand, I'm not one of these players or Don Juans, smoldering with self-confidence or a refined technique with women. Generally, I come across as a soft-spoken introvert, especially when I was young, shy and tongue-tied around females. I was always tall and lithe, toned from many years of swimming, but not muscle-bound or over-sized. Many women find me attractive in a boyish way, but I'm afraid I don't obviously exude testosterone. In many ways though, I like to think of myself as the guy that you're not expecting-- the surprise, or sleeper that produces his best effort just when it's needed the most. The point is, I certainly don't seem like one of these macho studs, struttin' his stuff at the pickup bars, seducing with smooth lines and over-powering pheromones. But I have my appeal, at least with certain kinds of women, and eventually I learned how to use it with effective results. In high school, I got tagged as a nerd pretty easily. I swam competitively, but in the rural Midwest, that made you more of a loser than a jock. I was also young for my grade and going through puberty later and a little more gawkily than most. Potsie from Happy Days got more ass than me. But that really changed my senior year when my family moved to the Bay Area in California. My Dad wanted to take a sabbatical from the college where he was teaching and got a grant to do research at Stanford for a year. We'd lived there for a year a few years earlier, and I liked living in sunny, liberal, northern California much more than Hicksville, Ohio. And, like many, my senior year was my chance to shine. I'd actually lost my virginity during my junior year while still in Ohio, but that didn't mean I hadn't tried to lose it earlier. I had one girlfriend my freshmen year-- Jan that lived just down the street. Her father was a college professor too and she seemed to like bookworms. She dumped me within a month because she thought all I wanted to do was make out with her. It was nothing more than kissing, occasionally with the tongue-- definitely no feeling each other up. But she was probably right, all I wanted to do when we were alone was mash. I found another girl who would mash my sophomore year. Lisa was on the girls swim team so we got some chances to check each other out in Speedos. She had a nice trim body and tits with noticeably large nipples I was just dying to touch. But every time we'd kiss for awhile and I'd try to move my hands around from her back to the front of her chest, she'd stop me. My junior year I was finally able to hook up with this kind of slutty girl, Darcy, a senior. She was a grade above me and almost two years older, as I was slightly young for my grade and she was a little older than most in hers. Her butt had grown noticeably since her junior year and her big, swept-back Farrah Fawcett-style blonde hair annoyed me a little, but she had nice plump titties and she put out. Her Dad hadn't been around for a long time as far as I could tell and her Mom and older sisters all worked as cocktail waitresses or something, so we had the house to ourselves most evenings. We would fuck all the time. I hooked up with her at a house party after flirting with her for months. I'd just turned 16 and gotten my driver's license. My cautious father unusually gave me permission to take the car out that night so I took advantage of the opportunity to offer Darcy a ride home from the party. She'd been drinking Barcadi and Dr. Pepper all night and I'd had a couple Miller High Lifes. We got to her empty house and started making out on the living room couch. She let me not only squeeze her big knockers but I got to put my hand in her crotch. It was an amazing breakthrough. The second date I brought some condoms I'd stolen from my big brother's drawer and kept my fingers crossed. After some stupid movie at the local theater where I held her hand, I drove her home and followed her into the house. Once again, I was in luck. No one else was home. We made out on the couch for a while and I started mashing her tits, squeezing them like I was trying to make orange juice out of them or something while she pushed her tongue down my throat. I wriggled around and got my crotch between her legs and started dry humping her. I'll never forget the look on her face as she broke off French kissing me and her eyes got really big and surprised. "Wow. That's...that really feels like something." She pushed me away from her and stared directly at the cantilevered bulge in my Levis as if she had x-ray vision. Then she took me by the hand and led me away from the living room couch into an adjacent bedroom. "I want to make sure we're not interrupted while I see if this is really true." She sat down on the edge of a big bed, eyes level with my my throbbing hard-on which felt bigger now than it ever had in all my sixteen years, almost popping out of my waistband, straining to be free. Then she pulled me closer by my belt and started to undo the buckle. "You've got a mean one, and he's ready," she said, matter-of-factly, then pulled my jeans down, and managed to slip my boxer shorts over my raging erection, her eyes getting bigger all the time. When my full glory sprang out, pointing above her head at an angle to the ceiling, she let go of my shorts like they were red-hot and both hands flew to her mouth as she gasped. "I don't believe it!" she almost shouted, then stared at my proud flag pole for a wonderful silent moment. She lifted her eyes to mine and smiled like some fiendishly delicious idea had just come to her. "I feel like I just won the lottery." I knew I was bigger than most guys, maybe all the guys in my grade at school. But I didn't expect such an obvious reaction, and was flattered and excited by her attention, especially since I knew she'd already been fucked by about ten guys, all older than me. I was so turned on I felt light-headed. Darcy pulled off her clothes faster than I would have imagined possible, and I stepped out of my pants and almost went into a frenzy. Her boobs were fat and pert and just as tempting as I had fantasized, and her pink little slit was glistening with moisture and framed with light brown fringe. My instinct was to jump right in and start ramming her, but I forced myself to go a little slower. I wanted to do all those things I'd only read about before, and gently pushed her back onto the bed and snuggled up against her. I started kissing her fantastic breasts, making circles around her big, brown abstract areolas, sucking on her stiff nipples, while I squirmed my body on top of hers. I could feel the dampness of her pussy on my stomach, and my cock strained upward, almost reaching her pussy lips. "Oh, I love your big dick! Fuck me with your big dick!" she moaned and grabbed my wrists and tried to pull me up into her. "Wait," I said, and drew back from her. " I gotta put something on," and fumbled for the condom in my pant pocket. I opened it and tried to slip it over the end of my pride and joy, but it was like a too small tourniquet for my blood-engorged love pole. This was 1981, and if there were Magnum XL condoms then, I didn't know about them. I couldn't even begin to unroll the thing over the purple helmet of my upright soldier, standing at attention in full glory. "It's alright. I'm on the pill," she informed me, and pulled me back down on top of her. I propped my self up with one hand, then took the object of her affection with the other and slowly drew it across her labia several times, feeling her wetness on the end of my cockhead. I didn't really know much about the clitoris or anything, but I wanted to imitate all those great penthouse forum stories and really tease her into submission.