Digger
by Emerson Laken-Palmer
Copyright© 1999 by Emerson Laken-Palmer
Erotica Sex Story: An eighteen year old virgin finally gets the chance to lose his cherry. Will it work out?
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Consensual Drunk/Drugged Fiction Oral Sex .
For Amy and this memory...
It was 1967, the psychedelic "summer of love" and free sex, and I had just turned 18.
I remember that, as a teenager, girls were something that I had on my mind constantly. I wanted a girlfriend desperately back then. But how to get one had completely eluded me. Being in the presence of a girl, in those days, made me goofy and tongue tied.
I didn't consider myself a total dork though. I had "fooled around" with a few girls, when I was younger, but nothing past the exploratory, kissy-feely, "spin-the-bottle" type of thing that you do as a kid.
Looking back, at photographs of myself at that age, I had nothing special going (in the looks department) that would attract any girls to me. I was lanky and thin, with my unkempt brown hair hanging down to my collar.
My sudden shyness at talking with girls really hadn't presented me with too much of a problem though because the girls, in my neighborhood and at my high school, had all seemingly conspired to ignore me completely.
Late that summer my family went on vacation to a rental cottage in (what was then) a resort area of Canada on the shores of Lake Erie. We were going to be there for two weeks. My parents allowed me and my little sister to each invite a friend with us. I brought my buddy Mike and Bess brought her little girlfriend Laurie.
Me and Mike had a lot of fun swimming and laying on the long, sandy beach and playing ball but what we were REALLY looking for was (as always) PUSSY.
I had specifically brought Mike with me because I knew that he had a way with the girls. He wasn't nervous or shy around them (like I was). He had gotten laid (many times) and seemed to know how to get what he wanted from the opposite sex. They all seemed to want him too. He was eighteen and dark and had a James Dean like quality about him that made him popular at his High School. I figured he could get us into the sack with a couple of vacationing cuties and make this a summer for me to remember forever.
This (as I had it figured) was going to be my opportunity to finally lose my virginity!
Mike knew what was expected of him and he did his best for me. Whenever we were at the beech, he would walk up to pretty, bikini- clad gals and try and get us lined up for a night of sexual bliss but (for some reason) none of his charm or appeal seemed to be working.
Maybe (I assumed) it was because they saw, as he talked with them, that he was saddled with me.
Mike always came away saying the girls had told him that they had to go home or that they already had dates for later.
The first week of vacation went by disappointingly and then most of the second.
The day before we went home, me and Mike decided to walk around down in the little town of Leamington and see if there was any action there. It was the average, sleepy little town, with it's main street of grocery stores, hardware emporiums, theatre, bakery, drug store, clothing stores and hotels (because there were no bars in Ontario then - you had to have a hotel to serve liquor).
We were just leaving the drug store when we met a gang of local teens. There were about ten of them, just wandering around like we were. They looked like the Canadian equivalent of early punk- rockers. They all wore leather and tried to seem like tough guys. They asked us for cigarettes and we gave them some. Guys like these would have taken all my smokes and kicked my ass but they seemed to like Mike, as he stood and talked to them. They were Rolling Stones fans and Mike was too. They talked about how Mick Jagger and Keith Richards could easily beat the crap out of John Lennon and Paul McCartney (in a fair fight) and how GET OFF MY CLOUD was ten times the song that STRAWBERRY FIELDS was and then we got to walking around the town with them.
There was a girl hanging out with the gang. She called herself "Digger" and she was about eighteen and tall and skinny. She had shoulder length, bleach-blond, over-permed hair and a cute, upturned-nose kind of face. She had two rows of perfectly aligned, white teeth behind the full lips of her pert mouth. She looked like the actress Meg Ryan would have appeared as a teenager. She wore a white t-shirt and a black, leather jacket with lots of silver zippers and tight, over-worn, black, denim jeans and black, high-heel shoes with straps at her exposed ankles. She walked, with her hands in her jacket pockets, in an easy, graceful gait that made her ass sway slowly and seductively.
I couldn't keep my eyes off of her. She was pretty and brash and loud, bending and laughing and grabbing the guys and smacking them as they all walked and talked, in sexual innuendo, about her thin but curvy body.
"Digger's got the hottest little ass in Canada," one boy laughed as we slowly passed the bakery on Main Street.
"But not for you, Arnold," she giggled, putting her hands on her hips and shaking her round behind at him. Her black jeans molded perfectly to the cheeks of her ass as she wiggled it.
Everyone laughed.
"Do you spit or swallow, Digger?" asked another.
"Yours I'd spit, Ricky. But only after I bit that little fucker off for you!"
Ricky assumed a painful expression and clutched his crotch and she growled in mock anger and playfully punched the red-haired boy in the stomach as everyone laughed again.
"Digger swallows," stated the tall, muscular, older boy, who seemed to be their leader and he put his hand in her open jacket, as he walked beside her, and grabbed the bump of her small, left breast and squeezed it adding, "at least, she always swallows it when I cum in her mouth."
"Ohh!" the gang members sang, in unison, respectfully to their leader but, at the same time, tauntingly toward Digger.
"Yeah," she said, pulling his hand out of her jacket and walking backward as she turned to look at the group, "and, I bet, all of YOU swallow, when he comes in YOUR mouths, too!"
"Ohh!" they all taunted again, but knowing that she had bested them.
But one of the boys wasn't going to let that insult go unchallenged. "And YOU don't like to eat pussy, Digger? That's not what I hear, eh? I hear that you and Sandy Johnson stripped off your suits and made each other cum, on the beech past Seacliff Park, the other night. I heard it from her brother! He was watching you two from the edge of the grass!"
"Yeah, Lee," she replied now, looking back at him, "and Sandy Johnson won't let you even near her. Does that mean that she knows that my little tongue is longer than your cock?"
Everyone laughed again. Except Lee.
After a time, I joined in with their raunchy talk, commenting approvingly about her sexy body but not in an insulting way. Digger wasn't smacking me for what I was saying (though I wanted her to touch me). She just smiled at me (and what I was saying) and she looked at me in a way that other girls, I had known, never did. It was as if she was appraising me for some unknown purpose.
After we had walked around for a while, we ended up by the lake, at the edge of the town's residential area. Old, asbestos-sided houses and side streets took up one side of the road that overlooked the rise leading down to the beech. The other gang members had split off and gone home and it was now just Digger, Mike and me.
I stood next to the dilapidated, wooden fence that was supposed to keep people from walking down, past the private cottages, to the beech below and watched Mike and Digger as they stood together in the middle of the blacktopped road. I was waiting for him to start talking to her and working his charm on her. Hoping that he could get her to maybe do something with us. She had her hands in her jacket pockets again and they were now toe-to-toe in front of a green house with a screen porch.
"So," Mike said to her, after they had just stood there for some time, "if I told you that you had a beautiful body, would you hold it against me?"
Digger looked up at the sky and snorted and then she took a step back, cocked her head at him, bent in amusement and yelled, "Jesus God! Is that the kind of bullshit line those bad-ass Detroit girls go for?" She shook her head and laughed at him. "Does that lame kind of shit really get you into THEIR pants?" she scoffed as she backed away from him and stood, by the fence, next to me.
Mike seemed uncharacteristically embarrassed and mentioned that it was getting late and that my mom would have supper about ready. He turned and went back to the cottage leaving me and Digger alone.
Digger looked out into Lake Erie as I stood close beside her and listened to the gulls and the wind and the waves coming from down on the beech. I noticed that her heels and her long, sexy legs made her stand almost as tall as I was. I could feel her body shiver next to me and (summoning courage) I took a chance and put an arm around her soft, thin waist. She turned abruptly to me and, without warning, wrapped her arms around my neck, softly pushed her pretty mouth to mine, and kissed me in a sexy, tongue probing manner that I was unused to but thrilling me to my toes as I closed my eyes and tasted the sweetness of her warm, agile mouth.
Just then a young, dark haired, bare-footed boy approached from up the road and hollered, "Amy! You gotta' get home! Mom's lookin' for you!"
Digger broke off our sweet, wonderful kiss, stamped her high- heeled foot on the loose gravel and turned to the boy. "Damn you, Kevin!" she yelled. "Can't you see I'm busy?"
"Well," he repled, unflustered by her anger, "get UN-busy and get home!"
The boy turned and slowly walked off and Digger sighed and said, "That's my little brother. He's a pain in the fuckin' ass!"
She snatched a cigarette from the open pack in my shirt pocket and lit it with a shiny Zippo from her jacket, blowing the smoke directly into the strong, warm, August wind that was whipping in from the great lake.
"I gotta' go," she said and she turned and started to walk away, leaving me standing there alone.
"Yeah, I understand." I called out to her.
Digger stopped and turned to me. "Listen," she said and she took another drag of her cigarette, "see that little white cottage by the access road over there?" She pointed to it.
"Yeah."
"I'm baby-sitting for the Miller's tonight. They're from Ohio."
"Yeah?"
Digger flicked her cigarette aside and walked back to me, taking my hands and placing them on her warm sides, at the curves of her hips. She held them there as she looked right into my face with her pale-blue eyes and smiled. "Do you like me?" she asked, her eyebrows raised in query.
I laughed. "Of course I do!"
"Then, do you want me?"
"What do you mean, do I want you?"
She laughed now but then her face became serious as she stared into my eyes. "I mean, do you want to fuck me?"
I had never been asked a question like this before and the look on her pretty face and the feel of her thin, feminine body between my hands and the meaning of her question caused my dick to harden rigid in my pants.
"Y-yes!" I stammered.
"Alright," she stated flatly. "You come to that cottage at ten o'clock. Knock on the door and I'll answer. The Miller's have one kid. She's a baby and she sleeps the whole time I'm there. They're going to dinner and a movie and they won't be back till after midnight. We can fuck in their bed or in the livingroom, on the couch or on the floor. Anywhere you want to fuck me. I don't care."
I just stared into her pretty features, not believing my wonderful fortune as she said those words to me. My mind was reeling with the fact that I was finally going to get laid! That a girl (an attractive, long legged, curvy girl) was actually going to willingly give herself to me!
Her eyes squinted at me, searching my face for a reply. "Okay?"
I gulped and nodded and said. "Yeah!"
Digger pushed herself against me now and kissed me again with even more wet passion than the last time. I felt her put her hand between us, as we stood together and kissed, and she squeezed my rigid cock, through my pants, making it throb wildly. She removed her mouth from mine and put her soft cheek to the side of my face and her lips to my ear and I could smell a sweet fragrance in her blond hair as she said, "I want to feel this hard thing fuck inside me tonight. I want to feel it when it throbs and shoots your cum into me."
I trembled as she squeezed my cock harder and licked at my ear with her warm, wet tongue. She took my hand from the curve of her hip and pushed it up between her legs and then pressed my palm firmly against the jut of her pubic bone at the wide, smooth crotch of her denims. I could feel the outline and the heat of her pussy, through the soft material, as we stood together, wetly kissing and feeling each others' sexual areas, outdoors, on a public street, in the bright, yellow light of late afternoon.
"Amy!" her brother's irritated call echoed from way up the road now.
She pushed herself back from me and gasped, "Shit! I gotta' go!"
Breathlessly I replied, "Yeah. I heard."
"Ten o'clock," she stated as she turned and started walking up the road and she looked back at me as she walked and added, "Don't forget!"
Forget? I was so excited that I can't even remember walking back to the cottage or what was for dinner or if I even ate. I do remember that Mike was quite happy for me, after I told him what was going to happen.
"This looks like it, Pal," he said. "It sounds like a sure thing."
"Yeah," I said, as we stood by the side of our rental cottage where my dad's Ford Galaxy was parked, "but what do I do? What do I say? How do I act?"
"You fuck her, Man! That's all there is to it. She wants you! Just go over there and give her what she wants. Fuck her!"
"It can't be that simple."
"Don't make such a big thing out of this. That's why you strike out so much. It IS that simple. She wants your dick. Get between her legs, put it in her pussy and fuck her. That's all you need to think about."
"But what if, by the time I get there, she's not in the mood anymore?"
Mike laughed. "Not in the mood? That kind of girl is ALWAYS in the mood!"
"THAT kind of girl?" I said, with my eyebrows up.
"Oh man! Don't you know ANYTHING? Didn't you see her with those guys? Weren't you paying attention to anything that was said?"
I shrugged.
"She's the town pump! She's a... a... groupie! A tramp. A slut!"
My eyes flashed angrily at him.
"Emerson, you hopeless putz! Why do you like to make angels out of every girl who smiles at you? Wake up! She's a little whore! But don't get me wrong... I mean it in the nicest way. And she's going to give that sweet little pussy of her's to YOU! Get with it! Don't make such a big deal out of it. You're gonna' fuck this girl, not marry her!"
"God, Mike! That's not what I saw. She's a nice girl. I could tell. She just wants friends... people to like her. She just wants love and attention..."
"Love?" Mike laughed loudly now. "You asshole! It's no wonder you never get laid! You know what your problem is? You think with your dick when you're supposed to think with your head and THEN you turn around and think with your HEAD when you're supposed to think with your DICK!"
"That's ridiculous!"
"Yeah?" he challenged. "You THINK yourself out of more pussy than any guy I've ever known! Shit! My little brother is going to get laid before you do!"
I was listening to him but I wasn't listening to him. I was too edgy and nervous to listen or think.
The next two hours were the slowest of my teenage life.
My parents and my little sister and her friend went to the drive- in to see GOOD NEIGHBOR SAM with Jack Lemmon. That left Mike to sit (and me to pace) until quarter to ten.
"Alright," Mike said, calling a halt to my aimless walking around the little kitchen, "this is it. Zero hour of D-Day! American cock versus Canadian pussy. Go get her!"
I had chain-smoked all of my cigarettes so I took one of Mike's and lit it.
"Here," he said, handing me the pack, "you'll need one for after."
I was a bundle of nerves as I thrust the pack of Players into my shirt pocket and walked to the door, hesitating as I grabbed the latch.
"Go on!"
"But how do I..."
"Remember," he coached, "it's the wet, soft, hairy place between her legs. There's a hole there and it smells like tuna. You can't miss it!"
I opened the door and stepped out into the night, listening to the sounds of the crickets and the waves from the lake as I walked, in the warm night air, down the road that led to the rise above the Miller's cottage.
It was precisely ten o'clock when I knocked on the wooden, screen door. I could hear the sound of the television playing the theme from THE AVENGERS as I stood and waited for her to come.
THE AVENGERS theme ended, as I waited on the back porch, and then a commercial jingle for Winston cigarettes came merrily through the screen window.
I knocked again as I listened to the happy tune:
"... it's what's up front that counts
and up front, ahead of the filter,
only Winston has the smooth, fresh taste
that comes from filter blend..."
When I knocked the third time, the TV went silent and, after a moment, I could hear footsteps in the kitchen and then the door slowly opened and there she stood, smiling.
"Hi," she said, in a happy but odd sounding voice.
She was every bit as sexy and pretty as she was this afternoon. She was still wearing the t-shirt and the skin-tight, black jeans but not the jacket and she was bare footed now as she opened the screen door to let me in.
"You're right on time," she said as she took my hand and led me through the little kitchen area to the livingroom and sat down on the couch, smiling up at me and patting the space beside her.
It was a cottage exactly like the one my family had rented. A kitchenette and livingroom with a sofa, one old upholstered chair and a low coffee table. There was a black and white TV on a stand, across from the couch, and a counter shelf with a glowing lamp and an old radio on it. Two doors led to a dark bedroom and a tiny bathroom. It was all done in varnished pine.
I sat down next to her and she leaned to the coffee table and picked up a half-empty bottle of Bombay dry gin and took a long swig.
She looked at me, with her cheeks full of liquor, and then swallowed, wiping her pretty mouth with her wrist and holding the bottle in front of me. "Want some?"
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