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Groupie MILF: Chapter 1: Jake Python

"A recently divorced, single mother, embarks on a lusty Rock and Roll adventure"

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Author's Notes

"Melissa, known in her youth as "Easy Issa," is a recently divorced, single mother, recovering her life and self-respect. Chaperoning her daughter and her friends to a rock concert, her life is about get interesting. A huge shock rooted in her past, awakens the passion and perverted lust that used to consume her. Special thanks to all my friends that helped me with some rough patches and to Gladetheshade for writing the lyrics for me,"

“But, mom, you just have to!” To my “mom-ears,” it sounded more akin to, “Ba-hut, ma-homm.”

“I don’t think so, Jen,” my even, empathetic tones sounded motherly. “I’m very busy these days, what with your father no longer in the picture and all. I just don’t have the time to do anything other…”

She cut me off, her tone accusatory. “What? Drink a bottle of wine while you cry, and then masturbate with your vibrator all night? You’re better off without that cheating asshole, anyway.”

Cheating Asshole? That was actually a fitting name for my ex-husband. Both descriptors were accurate. I wasn’t certain about being better off, though. Richard and I had married, due to pregnancy, while I was very young. At six months separated, and three weeks divorced, I was a thirty-four-year-old single mother. I had an amazing, beautiful, brunette daughter and a shitty secretarial job, working for a lecherous boss who spent his entire day telling me about his sexless marriage, along with creepy implications that I could help him with that. At least I got the house—along with the mortgage payment, all the bills, and no real way to make ends meet. To make matters worse, my ex, Mr. Cheating Asshole, himself, ran off with his younger, more buxom, slutty, blond secretary. My entire life had become a cliché.

Stifling a chuckle at her brazenly-spoken truth, which included the crying into my cups and then blasting off with my battery-operated-boyfriend parts, I, instead, adopted my “mom-voice.”

“Don’t disrespect your father like that, he’s a…”

“Fucking cheating asshole that deserves to have his dick gnawed off by rabid weasels.” I couldn’t suppress my smile.

I knew where she was headed with her platitudes. She continued. “You’re the coolest, hottest mom, ever, and I hate him. Please tell me you’ll go.”

She adopted her sad, soulful, pleading face, her sparkling blue eyes eroding all my resolve. “Cindy’s mom can’t go with us, and you know they won’t let us into the arena without a parent, since we’re still underage. You have to, mom! It’s Chaos Dojo.”

“Can’t one of the other moms take you and your friends? I’m far too old to go to a rock concert.”

“Mom, you’re not old. All my teachers thought you were my sister.” She knew how to lay it on thick. “Puh-lease?”

The last time I’d been to any type of concert was a little over eighteen years and nine months ago, the night I got pregnant. I was a slutty hellion, exactly the type of girl I prayed Lisa would never become. Melissa is my real name, but most people call me, “Issa,” or, “Lissa.” In high school, before I dropped out to be a mother to Lisa, I was known as “Easy Issa” and “Lay me Lissa.” I’m not proud to say that the nicknames were well-earned.

In the back seat of Richard’s car, after a drinking and smoking binge at a rock concert, she had been conceived. I dropped out of school, raised her the best I could, and tried to be a good, loving wife. I was proud of her, the one thing in my life I didn’t fuck up.

He found good work, became a department leader in the sales force, and was soon married to his work. The sex stopped; the arguments began. After more than a decade of misery, I was now alone, destitute, and feeling lost and helpless. I had signed the papers, ending the verbal abuse, the fights, the crying over him sticking it to his secretary rather than me. No alimony or child support was assigned by the court, leaving me to fend for my daughter and myself. I hadn’t left the house for anything other than work, grocery shopping, and divorce court for months.

Maybe I could use a night away from my woes, feeling out of place among a sea of unruly, teenage rock fans. Most of my life had been spent trying to raise my daughter correctly, to keep her from repeating my mistakes. Being thirty-four, divorced, and with an eighteen-year-old daughter isn’t exactly a recipe for success. Karma ensured that I paid for my youthful wildness, a tithe I’d spare her from, if I could.

“OK, I’ll chaperone you and your friends, but, no booze, you’re underage.”

Lisa was a good girl, graduated with honors, was never in trouble, and, also, not pregnant before her sixteenth birthday. I could suffer through some loud, obnoxious music and throngs of screaming idiots for one night. I suffered through one screaming idiot for over seventeen years.

“You’re the coolest mom, ever,” she exclaimed, throwing her arms around me. “I already told the girls that you’d do it. They’ll be here any minute.”

“You did, what?”

“Coolest mom, ever,” she ignored my motherly scolding. “Second row! I can’t wait.”

Minutes later, her three friends, Janet, Aubrey, and Cindy, whom I mentally dubbed the slut-sisters, arrived. Barging in, the formality of knocking abandoned when they still thought boys were icky, they thanked me and addressed me more as a friend, not a matriarch.

“I wish you were my mom.”

“You’re the coolest, Issa.”

“Don’t worry about ‘cheating asshole’. All my guy-friends think you’re a MILF.”

I broke up their platitude party with a sigh, wondering what a MILF is. “When are we leaving?”

“Whenever you’re ready,” Cindy, the blond one, said.

“I’m ready.”

“Seriously, mom? You can’t go like that.”

“For sure,” her friends chimed.

“What’s wrong with what I’m wearing?” I was dressed in comfortable flats, sensible slacks, and a nice blouse that didn’t show off too much cleavage in order to avoid unwanted attention. The subdued gray and brown tones gave me a sensible, conservative appeal.

“Duh, like everything,” Aubrey, the redhead, said, rolling her eyes. She was dressed like a cheap hooker in a skintight, black mini-dress and high heels under slutty stockings.

“Come with us, mom,” Lisa instructed, emulating my no-nonsense tone.

“Makeover!” they shrieked in unison.

Twenty minutes and two-hundred protests later, my slightly-slutty, brunette daughter and her more-than-slightly-slutty friends had me “rock concert ready.” My blond hair was released from its sensible, motherly bun and teased out to slutty frays. My conservative, light makeup was replaced with harsh, dark rogue; glossy, whore-red lipstick with black outlines; and heavy highlights all around. My comfortable clothes, decried, “too frumpy, burn them,” were cast aside in lieu of a black fishnet top over a silvery, cleavage-enhancing push-up bra, a skirt so short that it was more of a broad belt, and strategically-ripped, black, thigh high stockings. My black, “date night,” stiletto heels, never previously worn because “cheating asshole” always forgot, matched the studded biker jacket I didn’t even know my daughter owned. For the sake of false modesty, a shimmery metallic-silver thong covered my promised land.

“There you are, Issa. Now you look super sexy, perfect for a rock concert.”

“I can’t go out like this. I look like a cheap whore.”

“No, mom, you look hot. Let’s go.”

Luckily, the two inches of makeup caked onto my face hid my embarrassed blushing as we walked to my economical, mundane, suburban-mom, four-door sedan. The ride from the mediocre suburbs into the dilapidated industrial zone was interesting. The girls chattered, excitedly.

“I can’t believe Chaos Dojo, the hottest band in the world, is playing our town.”

I had never heard of them.

“That’s because Jake Python grew up here. He wanted to come back and visit his hometown.”

“There’s no way anybody that sexy went to school here.”

“He did! He graduated from our high school.”

“Issa,” Janet began. “I read last night that Jake Python is almost as old as you. Do you know him?”

“Almost as old as me?”

“I didn’t mean it like that, you old crone. Did you have classes with Jake Python? Did you fuck him?”

“Janet!”

“Come on, mom. He’s super sexy. Look.”

I kept my eyes on the road, barely shifting my gaze to view the CD cover she proudly held up like a trophy. “I’m driving, young lady.”

“Issa, his real name was Monty Jacobs. He’s a year younger than you. Did you know him?” Aubrey asked me.

“Listen to them play, mom; he’s so hot.” Lisa crammed her prized Chaos Dojo CD into my cantankerous stereo. It twanged to life, not even groaning its usual skips of protest.

I failed to comprehend how being “hot” made for good music; nonetheless, the music was surprisingly good. While it was hard rock, the music had excellent structure, interesting dynamics, and the lyrics were heartfelt, profound, and had a depth and sincerity that I liked. I turned up the music, only partially to drown out the teenage, fan-girl wailing.

“Wait, girls, I knew a Monty Jacobs. They called him Monty Python. He would write poetry all the time, and was picked on by the jocks, including your father, Lisa.”

I smiled, remembering the shy, cute, introverted boy. I liked him. He wasn’t exactly a friend, but he was always sweet to me, showing me his poetry, holding deep conversations, and listening. Men who listen are so rare.

“We would have lunch together, occasionally, because he was one of the few people who didn’t call me…” I stopped, remembering my daughter was sitting beside me, “…who didn’t tease me.”

“You mean call you ‘Easy Issa’?”

“Lisa!” Four teenage girls laughed at me.

“No, it couldn’t be the same guy.” Could it?

We arrived at the large concert hall, a place called Diablo’s. A crumbling, brick, converted factory, it became a live music venue several years ago. Still looking as if it were about to fall over, the newer neon sign, a devil with a pitchfork underlining the name, blinked, a little neon flame blinking at the end. The parking lot was packed; multiple groups of teenagers, as well as older people, all dressed in lace, leather, and denim, milled about.

As nervous as I was about being dressed like poorly used sex-trash, I fit right in. Dressed in leather, denim, satin, and showing generous amounts of more skin, I was far from the sluttiest woman, or girl, there. Because we had VIP tickets, after two months of me scrimping and saving, we passed the long, but oddly well-behaved, line of general admission ticket-holders. I could feel teenage and young-adult eyes roaming up and down my body. It being so long since I was stared at with abject lust, I enjoyed the attention, even adding some extra sway and bounce to my gait.

Some lewd, but appreciative, comments came to my ears. “Girls, what’s a MILF? Some young man just called me that.”

Giggles and titters followed.

“Mom I’d Like To Fuck,” Aubrey laughed out.

“Oh, Aubrey,” Cindy exclaimed. “Remember when you caught Tommy whacking off to Issa’s bikini picture?”

“What?” I stopped and turned to them.

“Yeah,” Cindy continued as if it were nothing. “Aubrey’s ex-boyfriend, Tommy. Remember, last summer when we all came by to use your pool, and you were out there in your bikini? He took a picture of you, and she caught him stroking to you!”

The four girls laughed; I was mortified. “Wait. What? How?”

Aubrey guffawed. “We were fooling around and I came out of the bathroom and there he was, his little pecker out, wanking over you.”

Luckily, we reached the door, saving me from further embarrassment. Tall, muscular, rugged security guards scanned our tickets and gave us a quick pat-down to check for concealed weapons. Checking our IDs along with our tickets, the back of my hand was stamped with a sexy, female devil, her tail probing a provocative place. The younger girls’ hands were stamped with a smiling, male Satanic face.

“You can drink,” the handsome neanderthal said to me. His eyes roamed up and down my body, stopping at crotch level, where the hem of my too-short skirt revealed most of my shiny panties. It had been so long since anyone, man or woman, looked at me with open lust that my skin reddened with sexual heat.

“Come on, girls, let’s get to our seats.” I pulled them inside with me before I embarrassed myself.

Maybe it was all the needed attention finally being paid to me. Maybe it was finally getting out of the house with the intent of possibly enjoying myself. Regardless of what it was, I felt an extra spring in my step, an extra wiggle in my walk. I felt the eyes upon me, imagined their lusty thoughts, as I passed the other concert-goers. I liked it; feeling like a desirable woman, once more, was extremely arousing.

We found our seats in the partitioned-off VIP section. I was shocked to discover that while we were in the second row, I could almost reach out and touch the stage. Even more surprising was the fact that VIPs had wait-staff. I quickly took advantage of that and ordered three whiskeys, plus soft drinks for the girls.

The interior of the venue was impressive. As dilapidated as the exterior seemed, the inside had been renovated into a large concert hall, everything pristine. I people-watched, taking in the various outfits and youthful posturing going on. The venue was filled beyond capacity. I was into my third drink when the lights dimmed. The unruly but respectful crowd hushed as a lone man, a DJ from the local hard rock stations, strolled up to the microphone.

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“Ladies and gentlemen,” he began. “W.H.O.T, the hottest radio station in the world, is pleased to present a very special performance by the hottest band in the world. I present to you, the one, the only,” he paused dramatically, smiling, “Chaos Dojo.”

The lights blinked off with a sharp clicking sound. The sea of youth-gone-wild began chanting, “dojo, dojo,” over and over, stomping and clapping. Smoke, glowing from the bright-colored lights behind it, poured out onto the stage. Behind the curtain, haloed in blinking strobes and lancing lasers, silhouetted figures could be seen, picking up instruments, casually leaning towards each other as if conversing.

The dark figures took their positions and waited; for eternity, they waited. The crowd verged on hysteria, my energy and excitement peaking along with them. A bass drum thumped out a heartbeat rhythm, “pulse-pound, pulse-pound.” The house lights kicked on, into overdrive, searing whiteness and bright as an explosion, as a heavily distorted electric guitar screamed out an incendiary power chord.

The wave of energy erupting from the audience was irresistible. Caught up in the moment, swept onto my feet by the joyful current, I screamed and hollered along with the rest of them, my eardrums already rattling from the rowdy cacophony. As the blinding lights dimmed, leaving white spots in my vision, the sheer curtain raised. The show lights erupted, washing the band in rays of color and mystical auras; the lead singer, Jake Python, looking sexier than any man I’ve ever seen, a guitar hung low by his waist, shouted to the audience.

“Hello, Subtropolis. So glad to share this night with you. Are you ready to rock?”

It was him! It was my old classmate, Monty Jacobs. He had changed for the better. Stomping about like a god, full of sexual charisma and swagger, he had grown his hair long, grown lots of sinewy muscles, adopted pants so tight that I could tell he was circumcised from where I stood, and grew into a handsome, attractive man. He was most definitely no longer the reserved, timid boy I knew.

The show was spectacular. Not only was the music energetic, anthemic, and surprisingly deep and complex, but all the band knew how to keep the audience in a stupor. Although I didn’t know the music, I got caught up in the atmosphere, forgetting about “cheating asshole,” and having a fantastic time.

Sometime later, still enthralled with the concert, Cindy tugged at my arm. I turned to see her smiling at me, her eyes wide.

“Jake’s been staring at you all night.”

“No, he hasn’t.”

“Mom, yes he is,” Lisa screamed to me. She had to yell, two inches away from my ear, for me to hear her. “Is that him? Is that the guy you went to school with?”

I nodded. My daughter and slut-sister friends shrieked, then went back to enjoying the show. After that, I paid special attention to him. I didn’t believe my daughter and her friends until he locked eyes with me, smiling.

“Issa?” he mouthed between lines.

I freaked, nodded, then freaked some more. He somehow remembered me. Then their song, a teenage anthem of angst and hope, ended. Jake addressed the audience.

“Thank you. Thank you, everyone. You know why we did this show, right here?” he paused to let the audience shout back. “That’s right, I’m one of you. I went to school here, graduated at Keaton High, like most of you.”

He paused, working up the crowd, then continued. “What you might not know is that I wasn’t always the rock-and-roll sex-god you see before you. I was shy, bullied, and wrote poetry, which we all know is a surefire way to get your ass kicked.

“That’s cool, though. It’s cool because it brought me right back here, right to this stage, so we can rock our faces off together. It also gave us our first hit single. In all the school, there was one girl that treated me like an equal, sat with me at lunch, so I wouldn’t be alone, and listened to me. Her name was Melissa, and she didn’t know it, but I had the biggest crush on her. Still do.”

The band began a slow, soulful, electric ballad.

Jake continued. “I wrote this in study hall, but never dared to let her see it. From our first album, Chaos Unleashed, this one’s called 'If Only I had You'. This is for you, Melissa.”

Oh my God, he’s staring right at me, I thought to myself.

“Oh my god, mom!” my daughter screamed. “He’s staring right at you.”

Fuck!

The song was a touching song of unrequited love, all the passion and desire of youth intertwined through the music and lyrics. When he hit the chorus, it seemed as if he were singing solely to me.

If only I had you.
The world would be mine.
I'd fight a thousand demons
Just to stand by your side.
If only I had you,
Everything would be alright.
I'd love you every single day
And hold you in the night.

I was flabbergasted. The rest of the concert was a total blur to me. All I can remember is that I had an excellent time, felt light and young, and drank too many whiskeys. The house lights clicked on after the second encore, leaving me wanting more, my ears ringing and stuffy. My daughter and her friends kept going on and on about how Jake Python had a crush on me. I ignored their enthusiastic jibing, not because I wanted to, but because I was at a loss for words.

We filed out, marching in an orderly line along with the throngs of others. I was riding high, buzzing from the excitement, adrenaline, and relief from actually enjoying myself. Leaving the auditorium area, stopping by the vendor’s table to buy some vastly overpriced, souvenir t-shirts, we exited the fantasy-realm that was the concert, emerging into the mundane, regular world.

“Look,” Aubrey shouted while pointing, “the entire band is over there signing autographs.”

Possessed of a hive mind, all four of them veered towards the cluster of fans, carrying me along with them. All four sexy band members were there, posing for pictures, talking to both the press and fans, seemingly enjoying the interactions. I waited on the outskirts of the crowd, not wanting to impose. The four youths in my care dove in, trying to push and elbow their way up to the front.

I caught my daughter's eye. “I’ll be in the car.” I turned to go.

“Melissa, wait,” a sultry, slightly raspy man’s voice cried out. I turned to look.

Excusing himself, pushing his way through his adoring fans, Jake Python ran up to me. I saw the boy I once knew in the sexy man before me. Under his sexy swagger, muscular body, and shimmering long, bleached-blond hair were some phantom remnants of the Monty I once knew.

“I’m sorry,” he began. “I hope I didn’t embarrass you. I just saw you in the audience, and…” his voice trailed off, him smiling and looking deeply into my eyes.

“I’m flattered, Monty, or should I call you Jake, now? I just wish I had known back then.”

He shrugged a definitive, rebellious, rock-and-roll shrug. “I didn’t have the courage, then. Now I do. I see you’re still as sexy as ever.” His eyes roamed up and down my body, reminding me that I was dressed like a cheap whore.

“Oh,“ I gasped. “No, this isn’t the normal me. My daughter and her friends dressed me up like this.”

“Daughter? Are you married? Congratulations. Who?”

“Divorced, three weeks now. It was Rick Bartles.”

“He’s a fucking douche-bag. I’m sorry to hear that.” He grew pensive. “Hey, wasn’t he the one who….”

I finished his question for him. “Knocked me up? Yes. He’s gone now, ran off with his secretary. Now I’m a single mom, living in the old Winchester house on Wayward Drive.”

“Boyfriend?”

I shook my head to the negative.

He smiled at that. “May I meet your daughter?”

“Lisa,“ I demurely screamed at the top of my lungs. “Come over here and meet Monty, I mean Jake.” He laughed at that.

My daughter and her slut-sister friends charged out of the crowd towards us, gushing like fan-girls. He was so gracious with them, posing for photos, signing their shirts, and calling the rest of the band over for introductions. I was vaguely aware of, but not concerned over, the press taking photos.

I had Lisa drive us home. Such a fine, motherly example I had set. Drinking myself into a fine state of inebriation and rubbing shoulders with rockers was not setting a shining example. Ears ringing, head buzzing, and mind reeling, we arrived home. I needed to go to bed. My mind was thundering with improper thoughts and fantasies.

“Mom, is it okay with you if we go out and dance or something?” Lisa begged. “We’re so pumped from the concert.”

“Fine, no drinking.” I was in no mood to argue.

“Oh, and we’re all crashing here, okay?”

“Fine, Lisa. I’ll be in bed.”

“I can’t believe Jake Python has the hots for your mom,” one of them tittered on the way out. “Definitely a MILF.”

As soon as I heard the car leaving the driveway, I ran to my bedroom, shrieking like a fan girl, myself. I had never viewed Monty Jacobs sexually during high school. But, reborn as the highly sexual Jake Python, my body came to an entirely different conclusion. Being a recently-divorced, single mother who had wrecked her life, lamenting over what might have been was all I had left. Logic dictated that my best course of action was to shed those slutty clothes, peel off the myriad layers of makeup, and get some sleep. As soon as I saw myself in the mirror, my determination eroded into nothingness.

I looked whorish, slutty, cheap, sleazy, and so fucking sexy. Since I was alone, my torridly racing mind conquered my will. Looking up Chaos Dojo on my phone, I sent the music to my Bluetooth speaker and began to dance. It had been arousing enough to have young men stare and lust over the sight of me. Having a rock and roll star do it had my pussy on fire.

Cavorting about half-drunkenly, my hands moved up my inner thighs as I swayed my hips. My breasts bounced divinely in the thin, silvery bra, making my flesh hot and needy. I stopped my dancing, between songs, to remove the bra, leaving on the fishnet shirt. Now I looked like a porn star, felt like a horny nympho.

Feeling my arousal crest higher and higher, I dirty-danced to the songs, some of them bringing back memories of the recent concert. Possessed by lust, I peeled off my soaked thong, bringing it to my face, breathing in the scent of my arousal. That was enough for me. As soon as the cooler air hit my soaking, dripping pussy, I fell back onto my bed, my legs spreading in anticipation.

My panties, soaked with my creamy nectar, felt delicious caressing my inner thigh as I stroked my body with them, leaving a cum-slime snail trail over my crotch and across my chest. Fantasizing about being taken hard by a long-haired Jake, I pretended that my hands were his as they crammed my soiled, soaked panties into my mouth, muffling my moans of pleasure. A glance into the mirror revealed that Lisa’s mother was long gone; “Easy Issa” had returned, and she needed to cum.

Squeezing and pulling on my hard nipples through the mesh shirt was all the foreplay I needed. My slick cunt was begging for attention, needing something to fill that slicked hole, anything to give me pleasure. Too aroused to stop and grab my vibrator, my two fingers would have to do. Jamming them harshly into my sex tunnel, my ecstatic scream sounded primal through my soaked panties. Sucking on my thong, my orgasmic juices sweetening my tongue, my fingers roughly claimed my dripping cunt, thrusting in until half of my hand disappeared.

Needing more stimulation, my other hand attacked my clit, strumming on it hard and fast, exactly like Jake did with his guitar. I played my clit like he played his power chords, humping my hips to the beats of the drums, spitting out the panties, and moaning to his voice, my fingers sloshing along with the bass.

“Fuck me, Jake. Fuck me like a whore. Please, cum on me; cum in me. I’m fucking cumming; it feels so fucking good. Pound me! Take me.”

I had reached the point of no return and charged past it with wild abandon. My bed rattled, squeaked, and rocked with the power of my orgasm. Wave after wave of rippling pleasure ran over me, started anew, and filled me with burning pleasure. I came so hard that tears poured from my eyes, my soul released its burdens, and I cried out to Jake to do it to me, again.

As the tidal waves waned into gentle pulsing waves of pleasure, the ballad, my song, came on the speaker. I kept on brutally fucking myself, fingering myself to the rhythm. I didn’t know all the words, but I moaned and whimpered, in pleasure, to the beat. Matching the cadence of the song, I brought myself closer and closer to another orgasm as the song played.

I don't have much money,
No fancy clothes or shiny car,
No mansion in the clouds.
I probably won't make it that far.
But I can feel my heart beat,
And I know the reason why,
It beats so much stronger,
Whenever you walk by.

I'm not in your vision,
But when you smile I stand proud,
No arms wrapped around you.
Just another face in the crowd.

If only I had you,
The world would be mine.
I'd fight a thousand demons,
Just to stand by your side.
If only I had you…

Another orgasm ripped through me, calmer, but no less intense. I cried more, felt weightless, delighted that somebody saw me as a real, desirable woman. Exhausted, still a bit tipsy, I barely managed to undress and scrape off the whorish makeup, now runny and smudged from my orgasmic tears, before sleep overtook me. I dreamed of what life would have been like if Monty Jacobs, now Jake Python, had only voiced his attraction.

Published 
Written by krystalg
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