Innocent Milf Ch. 01

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A young man first meets a naïve but adventurous milf.
5.1k words
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Part 1 of the 12 part series

Updated 04/10/2025
Created 01/27/2025
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Prelude

Everybody says "this is based on a true story" and then proceeds to tell a completely over-the-top story about their wife or girlfriend suddenly turning into a voracious sex monster with hardly any motivation. I know. I get it.

Well, this is based on a true story. Real life is messy and not always narratively satisfying, so I've streamlined some stuff. The names and locations have been altered to protect the horny. Some events have been combined or rearranged in time. Some people have been combined or had some specific characteristics flip-flopped. This story also wanders through various genres and categories, so each chapter has a different tag as it follows the characters.

Everybody in this story is over 18 and of legal majority.

Enjoy!

Chapter 1

I first met her when I was a high school senior living in southern Arizona in 1993.

Jurassic Park was the biggest movie at the box office. Bill Clinton had been inaugurated in January. Everybody was making dumb "Got milk?" jokes. Unforgiven got the Oscar. Whitney Houston's I Will Always Love You was topping the charts. The Dallas Cowboys won the Super Bowl. And the girl of my dreams appeared without warning in my life.

The doorbell rang, and I dragged my surly self to answer it. In the 90's, it could have been anybody—door-to-door salesman, Girl Scouts selling cookies, Jehovah's Witnesses. But it was my friend Jack, and there she was, standing next to him. Hunching forward just a little, as if not certain she should be here, she made me stop short. She looked old enough that I probably shouldn't have been sneaking glances at her tits, but not old enough to call her "ma'am."

"Miss," maybe.

"Hey, we need to borrow a knife," Jack said.

Jack and I were part of a Mountain Man historical re-creation group. Ever since I was a kid, I'd been thrilled by stories about Daniel Boone, Davey Crockett, and Hawkeye from Last of the Mohicans. Once my dad's job moved us to Arizona from Wisconsin, I found that there were people who spent their time sewing buskin trousers, smoking corncob pipes, and learning to whittle—and fight—with Bowie knives.

It took no time at all for me to start showing up to their meetings and Rendezvous, and soon my best friend joined me. One of our favorite parts was knife-fighting. It was halfway between martial arts and playing pretend like a kid—and more fun than I could remember having in most of my life. Bowie knives, navajas, Arkansas Toothpicks—soon I had a collection of them, and Jack and I trained with plastic versions we ordered from Soldier of Fortune.

Now I found myself ogling the lady next to him as he stood on my porch, asking to borrow an extra. Auburn hair, gray eyes, heart-shaped face, shorter than me by a head, and shapely enough to get my high school heart pounding, she smiled as if embarrassed and nodded silently at me.

"This is Matt," Jack said. "He's the guy I told you about. Matt, this is Cary."

"Like the Stephen King movie," I said in recognition.

Her smile wavered. "Sort of. It's spelled with one 'r' and a 'y'." She stood up straighter, and the fabric of her Goo-Goo Dolls T-shirt stretched alluringly over her chest. To cover the fact that I had glanced back down, I asked, "Cool. Did you get that shirt at a concert?"

Her smile returned, and this time it lit up the corners of her eyes. "I don't get to go to many concerts, so I splurged."

"Come on in," I said. "I'll get the knife." I jogged upstairs to my attic room and rummaged through a bag full of plastic knife trainers and extra rawhide straps. All the time, my mind was racing. A girl! A girl wants to come do knife-fighting with us! Of course, at the time any girl was enough to draw my gaze. But I already liked this one; anybody interested enough to come to a complete stranger's house for knife-fighting had my attention.

By the time I had found a couple of extra practice knives, Jack was sitting on the stairs chatting with Cary. He was always more outgoing than me, better at making friends. I was better at keeping them. He was always a bit beefier and stronger than me, but I was always quicker and had more endurance than him. We made a good team. Between my handful of bluegrass friends and his handful of paintball friends, we had enough of a social buffer against the hardships of high school that neither of us hated being there, even if we weren't the most popular. He was currently engaged in one of his favorite past times—listening to himself make fun of me.

"And that's when I saw Matt in his full-on Lewis and Clark getup," Jack chuckled, hitching a thumb at me. "I wasn't sure whether to stop hanging out with him for good, or get a dumb racoon hat of my own."

"He chose the hat," I replied, tossing them the black plastic knives. Cary giggled—a really girlish sound. It made her nose crinkle up and her shoulders squeeze forward. I took a breath. "So what about you? How did you find out about this? You already know Jack?"

Cary had settled on the piano bench directly across the bottom of the stairs. She bounced a crossed leg and hooked an auburn curl behind her ear. "Oh, Jack did a talk about pioneers at my son's elementary school. Came in costume and everything. The kids were hanging on his every word. He mentioned at the end that he was part of a group, and that his friend made the powder horn he was wearing."

Jack nodded. "Extra credit for Mr. Jefferson's class," he added.

"Technically the cow made the horn," I said. "I just learned how to hollow it out and make my back yard stink."

Cary giggled again, and I felt my pulse speeding up. She hefted the practice knife experimentally as she talked. "I always liked Last of the Mohicans, and I wanted to go exploring in the woods with a tomahawk ever since I was a little girl." She shrugged—prettily, I thought. "Luckily I was helping out with snack time when Jack came to do some extra credit."

My brain was firing on all cylinders. So she has a kid. She's a mom. No way—she looks like she could be the same age as my big sister. Is she married?

"Did you go see that movie last year?" I asked. Jack and I had liked Last of the Mohicans enough to see it twice in the theater. I expected her eyes to light up again, but a sad expression passed over her face as she shook her head, making me feel weirdly guilty for asking.

"No, I . . . I didn't get a chance. Maybe I can get it on video."

"I've got it!" I blurted. "I picked it up a week after it came out."

"Yeah, hang out with us and work on rawhide laces next week and we'll watch it," Jack offered. "Matt eats too much popcorn, but he's not bad at sharing if you remind him."

"Dick," I smirked.

And that's how Cary Woodley started hanging out with us.

* * * * *

Over the next several months, she became an unlikely friend. She wasn't just old enough to be my big sister—she was nearly old enough to have been getting her driver's license when I was born! She didn't look it, and she sure didn't act like it. She might have graduated from high school last year for as much as she laughed at my dumb jokes and liked the things Jack and I liked.

We hung out a surprising amount. Whether going to the arcade, hiking and then stopping at Wendy's afterwards, or knife-practice, it was always us Three Musketeers. We rotated between our three houses every week to watch some movie. Sometimes it was classic mountain man movies like Jeremiah Johnson or Grizzly Adams, and sometimes it was just fun stuff like The Terminator or Conan the Barbarian (those were usually at my house). My parents gave Cary a few strange looks when she started coming over, but they got used to her so quickly, it barely seemed like they noticed the age difference either.

Whenever we watched movies at Cary's house, it always had to be PG-rated because she had kids. Not that it was bad—although sometimes it was a little corny. Still, I had never seen the Randolph Scott version of Last of the Mohicans until she showed it to us. And I found out that she really liked going for walks and talking about stuff. Books, movies, music, TV—whatever. Jack sometimes bailed on the walks—his patience for the sort of long, rambling musings I got into was limited. Cary seemed to thrive on them, though, and often went off on her own long tangents.

Cary talked about her kids all the time—she had two, and they seemed like the most important thing in the world to her (although painting was a close second). She never mentioned her husband except when also talking about her kids. We only ever saw him once or twice at movie night, and he always seemed sort of annoyed. Once she called his office from a payphone to ask if he could pick up their daughter from soccer practice because Bowie knife training was running long. Even though we couldn't hear everything she said, she came back from the payphone with the same sad expression she'd had when I asked about seeing Last of the Mohicans in the theater.

She was good at Bowie knife—after I got over my misplaced sense of chivalry in trying to take it easy on her during practice, we had a ton of fun sparring. A lot of the older guys in class made it a point to ask if she wanted to practice with them, or offered to carry her gear bag. It always made my heart sink, but she would usually just smile and shake her head. After a few weeks, I think that the rest of the Mountain Man group thought that she had adopted Jack and I somehow, but it never felt like that to us. We were just the Three Musketeers (or sometimes the Three Amigos).

The three of us usually carpooled together to practice on alternating Wednesday nights; whoever drove chose the music. It turned out that Cary liked bluegrass when I tuned in to our local AM station that played it—even though she had not listened to it much. When it was her turn to drive, I was delighted to learn that she not only liked the Goo Goo Dolls, but also a bunch of the obscure prog rock that I also liked. It wasn't long before we bonded over King Crimson, Kansas, and Rick Wakeman.

Sometimes she would show up to practice with a hard look in her eyes as if she were angry. Jack and I usually made it a point not to press too hard on what was bothering her, but it was obvious that she wasn't happy at home. On those days, I was more than glad to bow out and let one of the older guys spar with her—and for them to go home with a veritable rainbow of bruises on their forearms and ribs.

Once in a while, she would come to training in a getup that looked more like something from an aerobics class five years ago than her usual jeans and sweatshirt. In her headband, tights, legwarmers, and wide-necked sweatshirt, we soon took to calling it her "Flashdance" gear. I couldn't help the longer than normal glances when her extra-wide sweatshirt neck drooped down over a bare shoulder and revealed what little cleavage her sports bra allowed.

As the autumn passed and winter approached, I never got over my initial attraction to her, but at least I was able to successfully hide the occasional stiffness when she would bend over to pick something up. She came to my bluegrass band gigs, went to Jack's Eagle Scout ceremony, and we both went to her art shows. She was an assistant curator at our town's tiny little art gallery, and occasionally sneaked a few of her own paintings into the displays.

They weren't Dali or da Vinci amazing, but I loved the colors. She had a great eye for color and the little details that made things seem real. Sometimes they were abstract and strange, but still made you feel something. They seemed like the sort of paintings you would see in a successful businessman's house. She had a whole room in her house that was devoted to painting. It was draped with painters' cloth and had half a dozen canvasses kicking around in various states of completion. Her old, paint-spattered tape deck was always playing something different whenever we came over for movie night and caught her still working.

We all independently dressed up as characters from movies we had watched for various Halloween parties that we had been invited to, without knowing that the others were doing it. We all laughed at the next knife practice when we talked about it—Jack as Conan the Barbarian at his paintball club hangout, me as Connor MacLeod the Highlander at my buddy Ty's fancy party, and Cary as Catwoman for her husband's office party. I would have paid money to see that.

As the year finished up, she invited us to her Solstice Exhibition—an event that featured more of her art than she usually showed. It was a big deal for her, so Jack and I agreed to go. My parents had long since ceased to express concern about my hanging out with an older lady, and started hinting about trying to make connections for my college application letters with what passed for the artistic community in our town.

Going to Cary's exhibition was the first time I saw her in anything but old grubbies for knife training or regular T-shirt and jeans for grabbing tacos and coming to the bars or restaurants where I played with my band. I guess it was the first time she had seen me in a suit, too. I had gotten it—partially with my own money—for senior pictures. A blue three-piece suit with a silver tie and shiny black shoes. I guess it looked pretty good on me, for being a gangly 18-year-old. I certainly thought so at the time.

But Cary—I had to sit on a bench in the entryway and breathe for a moment when I saw her in her little black dress and rhinestone choker. I had the idea it was called a "cocktail dress," and it hugged her curves, scooped open around her cleavage, and left her arms bare. I was so jealous of her husband, it stung the back of my throat. I'd had a couple of semi-serious girlfriends before, sure. But seeing Cary dressed like that really made me put them mentally in the "girl" category.

"Matt! Jack!" she called, bouncing on her toes a little as she waved. As she did so, one of the straps of her dress slipped, revealing a spaghetti-thin strap for a burgundy-colored bra. Even that was enough to make me stick my hand in my slacks pocket in what I hoped was a debonair manner. She trotted over to us, excited as a kid showing off a macaroni craft. Behind her glowered the sandy-haired man I recognized as her husband.

He looked angry. As I had begun to find, he was often angry-especially when he couldn't control what Cary was doing. I didn't realize at the time what a piece of shit he was, but even as a clueless self-absorbed teenager I could tell he made her tense and anxious. She gave both Jack and I a quick hug and thanked us for coming. I savored the fractions of a second her body was pressed against mine.

"Wow, you look totally respectable!" she said to Jack, and then turned to me, "And I love your suit, Matt!'

Jack grimaced. "Hey, why does he get 'love your suit' and I get 'totally respectable?"

Cary's husband stepped closer. "How soon until you do your speech and we can get out of here?" he asked sourly.

Cary's expression curdled. "Not long. Have another drink. I'll come get you."

He walked away, posture surly. I pretended not to notice, and said to Cary, "I can't wait to see what you've got in store this time!" She smiled again, and moved on to say hello to a knot of women in colorful dresses and pantsuits—one of whom was wearing an enormous decorated sun hat inside.

"Dude," Jack muttered as I watched Cary go. I pushed a hand through my getting-shaggy hair and tried to look at home in my suit. I hoped he hadn't noticed how turned on I was from Cary's hug. And her dress. And her slipping dress strap. Hey, I was 18. It didn't take much.

"What's up?" I asked, trying to sound casual.

"Did you get a load of her asshole husband? What a buzzkill. Looks like something crawled up his ass and died." Jack made a beeline for the nearest refreshment table and started to munch down what looked like fancy crackers and cheese. "How did someone as cool as her end up with such a dickweed?"

I'd been wondering about that myself over the past several weeks as we get to know Cary better and better, and to contrast her with the happily infrequent glimpses of her husband we got. I was hardly a relationship expert—both of my serious relationships had ended after only a few months. Still, it didn't sit right with me.

We were standing beside a series of paintings that looked like old Renaissance scenes when Cary came back from socializing with her coworkers from the gallery. She was leading a willowy blonde-haired girl our age, wearing a lacy antique dress and satin gloves. Cary looked delighted. The girl looked nervous.

"Hey, Matt! This is Sascha—she's the violinist I was telling you about the other day," Cary beamed. I dimly recalled a conversation we had had after movie night when she mentioned that there was somebody she wanted me to meet. After a few moments of chitchat about the difference between mandolin and violin, it became obvious to me that Cary was trying to set me up with a friend's daughter. I was more amused than annoyed. Cary had been asking about our social lives outside of knife-fights, hiking, and movie night, and I guess she had decided that it was up to her to help Jack and me find girls.

Sascha was nice enough; she reminded me of sort of a cheerful Wednesday Addams. Once we started talking about hiking, things warmed up. She really liked to go walking in the woods and in the hills at night. She was one of those witchy girls who loved Silver RavenWolf's book and burned incense made of herbs she'd gathered by moonlight; I liked hiking and trying to spot wildlife. Pretty soon we were joking about falling into patches of poison ivy and being surprised by snakes.

Jack wandered off, but circled by a couple of times to see what was up and told some funny stories about his scouting days that made us all laugh. We chatted about the most recent Simpsons episode with Mr. Burns' casino, and I did an impression of him that had both of them chuckling. I kept an eye out for Cary, who strolled by once or twice. She kept giving me encouraging smiles, and I nearly rolled my eyes. Subtle was not a word in her everyday vocabulary. Every time she swung by, her husband hovered behind her, looking like he had just swallowed a lemon. And each time I frowned internally a little more. What the hell was his problem? If he couldn't be happy for Cary's big day, he could at least act like an adult.

After close to an hour, Sascha had found a few excuses to lean on me or slap me playfully with her satin gloves. I wasn't complaining. As Jack returned, looking like he'd had enough of appreciating art, she excused herself and went to talk to one of her friends. They kept looking towards Jack and I, and giggling.

"Man, how is it that you're too scared to say boo to anybody at school, but you get the only unattached girl our age here to talk to you?" Jack muttered.

"What about her friend over there?" I asked.

"Dude, that's Rob Morton's girlfriend," he snorted. "No way."

"Fine." I scuffed my feet a little; I didn't like it when it felt like Jack and I were in competition. "Anyway, Cary basically threw her at me," I answered. As if summoned, Cary appeared nearby and made a beeline for us. Sascha's lacy dress had been pretty, and it really highlighted her cute, slim assets. But as soon as Cary came over to us, all I could see was the sway of her hips under the close-fitting black cocktail dress she wore.

"So?" she asked, gray eyes sparkling. "What do you think?"

I played dumb. "The exhibition is great. Your picture of wildflowers in the meadow is my favorite."

12