When you're young, life seems to bunch milestones together. It's like a never-ending parade of firsts and lasts. Losing your first tooth and having your last kiddie haircut. Kissing your first girl and losing your virginity. For some people, graduating high school is a seminal event--even the cardinal event of their lives.
For me, it was a "last day" milestone. A last day of childhood, with a door opening on the other side. I know people who only look back at that day, wistfully thinking it end of something great. I slammed it closed behind me.
It wasn't that I had a terrible childhood. But to me it was like getting the training wheels off my bike when I was five.
I graduated in early June and my eighteenth birthday was two weeks later. When that milestone arrived, I was on a hiking trip in the Trinity National Forest. It was my last camping trip with my Boy Scout troop. On the peaks, the sun was hot. In the valleys, among the redwoods, it was cool, even chilly.
I was one of just a few older boys. Our scoutmaster's son, Vin Sampson, and I were good friends. He was some months older than I was and we'd done most of the planning--choosing the route, marking the maps, organizing the means. The rest of the troop was made up of middle schoolers, freshmen, and sophomores. I knew them all, of course, from previous trips and our weekly meetings. Most kids give up the Boy Scouts early in high school though: it's not cool. I'd stuck with it, earning my Eagle. I loved the outdoors and the activities.
When we came down into the last parking lot at the end of the trip a few parents' cars were there to pick us up. We were hot and dusty, sunburned, and footsore--and happy both with our accomplishments and to be headed for civilization. We'd trekked seventy-five miles in two weeks, and it was unforgettable.
We expected the drive home to take most of a day, so we loaded up into the various cars, shook hands, and took off. I went in an Audi wagon with three of the youngest scouts, the twins David and Cliff Scoresby, and Bobby O'Neill. It was Bobby's mom, Eileen O'Neill, driving. The car was cramped, but, since I was taller and bigger, I got the passenger seat up front. Besides the legroom, I was glad for the arrangement because after two weeks, I was done with fart jokes.
We hit an A&W on the way south. Let me tell you, no five-star gourmet meal tastes as good as a root beer float when you're just off the trail. When we hit the road again, I struck up a conversation with Bobby's mom.
"You missed your birthday," she said.
"No, I was there," I laughed. "It was everyone else who bailed. These guys made it fun, though and it's not like turning twenty-one or something. I didn't really need a party or something."
"What about a special someone?"
"Nah, there isn't anyone, you know, like that." In fact, I was still a virgin. I hadn't had as much success dating in high school. I wasn't unpopular or anything, but I'd focused on school. I'd had a job and a car. And girls were still kind of a mystery to me.
"That's too bad. You must have to beat, uh, dodge lots of gals," she replied. I laughed at her avoiding beating anything off, given the backseat audience--not that they were listening.
"Not as such." Our conversation turned to post-high school plans. I was headed for Berkeley, and we talked about what I expected it to be like.
Eileen was a big woman with long dark hair, pulled back in a loose French braid. She'd always seemed friendly but didn't really stand out in my mind from the general category "parents" in my young mind. Just over the threshold of adulthood, I wasn't prepared to look at her in a different light yet.
In retrospect, she was a hair over thirty, which is still a significant age gap, but not old in any real sense of the word. And it dawned on me incredibly slowly (since I was completely unaware of the
possibility
of any such thing) that she was subtly flirting with me. Like many big women, she had capacious boobs, which she seemed to flaunt in my direction. At the A&W, she'd been behind me in line, and brushed one of them up against my arm. It could have been a casual thing, an accident. But it felt deliberate. Here in the car, she spread her knees somewhat so that her skirt rode up some. That way I could look at her naked lower legs and the inside of her knees. In our chatting, driving with her left hand, she'd touch my hand or arm sometimes. And there was a definite double-entendre moving through what would otherwise seem to be innocuous topics.
I was an innocent: I
got
the flirty dirty stuff, but my pea brain didn't connect that with any
actual
interest on her part. I was a Boy Scout, for Christ's sake. Older married mothers didn't do that sort of thing, so it must be harmless fun.
About halfway home, we stopped for gas. The three boys ran into the Jiffy Mart to buy candy or such. Eileen asked me if I could fill the car with gas.
"I need to use the restroom. I'm weaning our daughter and all the conversation with you is making me leak," she announced. Indeed, the front of her blouse was soaked on one side. I recalled her being pregnant maybe a year or two ago, when Bobby had first joined the troop. Now she rustled around for a sweatshirt to cover her embarrassment.
"What about our conversation brought that on?" I asked, honestly innocent. But she took it as a deeper flirtation.
"I don't get to talk to many big handsome lads. When I do, sometimes things get... wet."
That's when the pump went 'clunk' and shut off, distracting me. The boys came running back and I finished up with the fueling. We hit the road again.
When we finally arrived home, we dropped off Dave and Cliff first. Then, surprisingly, we dropped Bobby off. He dragged his pack into the house, where his father was waiting to help. I could hear the wailing cries of their young daughter. It was bit before ten p.m.
Eileen came back out to drive me the final miles to my house. My parents were divorced. I lived with my dad, and I knew he'd probably be up, waiting. Instead of going directly to the house, though, Eileen drove to a nearby overlook. Not really a "lover's lane" kind of place, but it was private and quiet.
She turned off the car.
"So, you're going away in a few weeks. Will you be back at all?"
"Maybe in the summers. I need to make money then to cover my expenses and stuff."
"I hope you'll check in any time you're home," she said. "You know, I've never set up here with a man and not had him touch them." She put her hand on my knee, while turning to face me.
"Touch what, Eileen?" She'd asked me to 'stop with the Mrs. O'Neill' hours ago.
"My boobs. Don't you want to touch them?"
"Um..." I really hadn't thought about it. But I reached out to tentatively prod one. It was warm and firm. In addition to the sweatshirt, she was wearing a blouse and a capacious nursing bra. Thus, I didn't really have a sense of "touching her boob". It wasn't the first time I'd touched one, but certainly the first time I'd be brazenly invited to do so.
I moved my fingers and thumb around, until I located a nipple longing for attention. As I did so, she leaned in towards me. I couldn't mistake this. I kissed her.
Her mouth was moist. I closed my eyes. Our mouths opened and moved together. I pulled back. She had a tiny cherubic smile to match a hot little kiss. I dropped my hand and pushed it up under her sweatshirt as I leaned in to resume our embrace. Her shirtfront was soaking under my fingers.
Her hand reached over my shorts and found my youthful enthusiasm had flowered quite nicely in response. As our lips touched and parted and touched again, her fingers deftly outlined my profile and began to gently, gently nudge and tug me.
Her breath came faster; she moaned slightly between kisses. I lowered my hand and touched a knee. Her thighs jerked apart; the invitation clear. I blew into her ear as my hand reached the point just below her panties where her thick legs were slowing my progress. Her dark eyes looked over and I could read desire there. Her legs parted slightly. My fingers reached out. Reached and touched the silky gusset of her panties.
"Oooh," she sighed, as I worked my hand up to do more than brush vaguely her forbidden fold. Then she opened her eyes again. It was like I could see her thinking what people would say if they knew what we were doing. "That's not fair. And probably not right. Focus on your birthday present."
She gently pushed my hand away with one hand, while her other stroked and jerked me. Undistracted by the feel of her lips, the scent of her skin, the novel joys of fingering her panties, I was suddenly and seriously focused on the growing tumult in my shorts. My cock was firm and hard, unused to the attentions of a mature, experienced woman.
"Yes, yes," she urged. The coquette's smile returned as she guided and coaxed me. She leaned over and whispered in my ear: "I want you to cum for me. Cum for me, baby."
I had lost all sense of where I was, sitting in a car with an older married woman. I was consumed by the fabulous feelings emanating from my groin. I was dimly aware that my hips were bucking in the seat. Her gentle massaging melted into grasping yanks. Balls tight, shaft thick, control lost. My urgency boiled over and I flooded my underwear with a torrent of hot cream.
"Next time," she whispered. "Next time, I want that inside me."
She started the car and took me home. I don't recall how I managed to hide the wetness in my pants until I could step into the shower.
And... then a thousand
other
things happened. I went away to college and there was no "next time" that summer.
Berkeley was a new world to me. The campus is huge and classes were large. You could be completely anonymous. Yet into that, there was every kind of opportunity to make friends, connections, delve into experiences. I joined study groups, went to lectures, tried things. In the spring semester I had my first real girlfriend--and lost my virginity. It was a short-lived experience, but it gave me more confidence. I dated a little.
I went home that summer to work. I had a job with a family-owned company. They operated a couple of strip malls and four chain restaurants. I ran inventory for the restaurants, loading and unloading supplies, checking and tallying usage reports, weighing food, catching for (let's face it) theft. It was active work, physically and mentally. I might have made more waiting tables--and had more free time, but this felt more my speed.
My dad nagged me to take a Wednesday evening and to see the scout troop, but I kept putting it off. I still probably knew most of the guys, but it would be different. Younger guys would have stepped up by now and it was their show. They didn't need someone to come stare over their shoulder. So I didn't go until two weeks before I was going to head back to school.
It was exactly what I feared it would be. I just kind of stood off to the side and let them do their thing. The new scoutmaster was happy to see me, but I bowed out after saying hello.
When I went out to the sidewalk outside the Elks lodge where the troop was meeting, Eileen was sitting in her car. She called out to me as I was walking past and, in a flash, my mind snapped to the last time I'd seen her. I had played out that session in my mind all year. She was my "go to" fantasy when I needed to rub one out. I couldn't say why, when I'd been with a couple of pretty hot gals since. Maybe it was the forbidden nature of it? A young Boy Scout, barely legal, being stroked off by a mature married mother? That is not the definition of a daily Good Deed.
She didn't say anything about it. She didn't need to. Instead, she indicated the empty passenger seat in her car.
"Come sit. I'd like to talk to you," she said. I went.
