Autumn

Story Info
hearing her screams and watching her wiggle on my lap.
3.2k words
4.36
15k
11

Part 1 of the 2 part series

Updated 05/21/2023
Created 05/18/2023
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Prologue:

I'm Cheryle "Cheri" an Irish Catholic, Attorney, Singer-Songwriter thirty year old bi-sexual woman-💋 I try to keep my professional life separate from my personal life never the two should mix.

Chapter One - The Music Scene:

The culturally diverse uptown Chicago neighborhood has been an entertainment hotspot since the Roaring Twenties. It's home to some of the city's most beloved music venues and one of Chicago's oldest jazz clubs.

When the Byline Bank Aragon Ballroom was built in 1926, it was one of the most elaborate venues of its time. Today, the opulent interior stuns me every time I'm there, with intricate mosaics, soaring arches, and ornately decorated balconies.

Legend has it that secret tunnels link the Aragon Ballroom's basement to the nearby Green Mill, a Prohibition-era hideaway and a favorite of Al Capone. I like to sit in Capone's favorite booth, that's what the plaque on the wall says anyway, I love the Green Mill when I'm feeling down for its nightly jazz shows that keep the music going well into the night.

Just around the corner, the Riviera Theatre is a great place to catch popular national acts and indie bands. Built in 1917, it was used as a movie theatre before being transformed into a concert venue in the 1980s. The space has retained its grand interior, with French Renaissance Revival flourishes that create an amazing backdrop for performances by some of today's top musicians.

the Logan Square neighborhood is a hipster hangout that I love for its dive bars, art galleries, coffee shops, and cocktail lounges. It's also where I find the cutting edge of the local music scene, with venues that aren't afraid to spotlight under-the-radar bands and experimental sounds.

I like to walk Milwaukee Avenue a trendy thoroughfare that stays busy long after dark with bar hoppers and concert goers. I'll visit the Whistler, It's easy to miss, no sign, just a front window with rotating art installations and plenty of locals lined up for nightly no-cover shows.

Walking a few blocks down, I'll hit Concord Music Hall. This mid-size venue draws a young and trendy crowd for the diverse concert line-up, from nationally touring bands to up-and-coming acts. On any given weekend, there is a spectrum of artists taking the stage, including punk, electronic, indie, hip hop, metal, and everything in between.

Tucked away from the crowds on Milwaukee Avenue, Rosa's Lounge welcomes new and seasoned blues musicians to their intimate stage. The family-owned spot is one of the city's most beloved venues, and a tribute to the old-school clubs where Chicago-style blues was born.

If I'm looking for a chill night at a neighborhood watering hole, then I head across the street to Cole's Bar. Grab a craft beer, Cole's has great wine and beer selections, and shoot a game or two of pool in the front, then I'll head into the cozy back room to hear everything from cover bands to folk musicians. No matter who's on stage, admission is always free, panties are optional. Live music, comedy & open-mike nights are showcased at this laid-back neighborhood watering hole.

Cole's is a great place to get stage time too, sitting in with musicians/bands I know from the scene or playing a new song of mine on open mic night. That's when I first saw her swaying to a new song I was playing there was something magical in the way she moved. Simple, unassuming, a subtle desire settled in has I played and sang watching her dance.

Her dirty blonde hair framing her gorgeous face with green colored eyes wearing a Grateful Dead tee shirt, ripped faded jeans, and yellow flip flops. My eyes exploring every inch of her a strange fascination setting in. Coming off the stage when my time was over I walked over to the beauty not really controlling my own legs.

"I'm Cheri, I saw you dancing to my songs, did you enjoy my set?" I asked her.

"Very much, I saw you perform once before at the Lakeshore Tavern, I'm Autumn," She said with a big smile of straight white teeth extending her soft right hand. We stood there laughing, chatting and flirting it was an electric moment with Autumn and I was still holding her soft hand in mine. She was slightly shorter then me, with dazzling green eyes. Until what I assume was her date or boyfriend came from the front bar and whisked her away. I drank my craft beer and watched my beautiful Autumn disappear into the crowded bar.

Chapter Two-Going Home

Arriving at my tenth floor apartment I put on some Grateful Dead music, lit some candles, took of my clothes and laid on my bed starring at my little naked body in the full length bedroom mirror. The candles giving off just enough light I was already in the mood starring at my naked body in the mirror thinking of Autumn. My hands found my breast pinching my delicate nipples caressing and squeezing them, pinching. Bringing one of my breast to my mouth I teased with it flicking my long tongue over my hard nipple. Taking my time enjoying the show as I let my hand slide down slowly over my stomach through my neatly trimmed red pubes to my waiting wet pussy.

Rubbing softly, caressing, making love to myself, letting my fingers playing with with my wet pussy lips. Inserting one then two fingers inside me slowly, so wet, moving in and out my desire growing. My other hand following the same path to find my tiny clit rubbing it gently the whole time watching the scene play out in the mirror. My juices making a slurping sound as my fingers thrust in then out pictures of Autumn dancing in my head.

Tingling all over, legs spread and up, knees bent, what a great view of my sexy body in the mirror. Moaning, rising off the bed to meet my fingers plunging into me. My body dancing with pleasure, a magnificent feeling, my scent filling the room. Thrusting in deeper. Then out, then in, adding another finger and a third driving hard pounding my pussy.

Screaming, moaning, grunting, panting, pleasure exploding throughout my little body, my wet juices covering my hands and bed sheets. The sounds coming out of my mouth surprised me, grunts, moans, screams. Something primal taking over, losing all rational control, plunging my fingers in hard, deep ready to cum for Autumn.

A shattering orgasm shaking my little body, my cute little toes curl, screams and moans escaping my lips. Screaming her name, AUTUMN! pleasure radiating out through me.

Chapter Three-Chance Meeting

Sitting behind my big oak desk in my office at the law firm working on some legal motions I needed to file with the court later in the day. A knock on my door breaking my concentration.

"Come in," I said only minorly annoyed.

"Cheryle this is our new intern, A law student at Northwestern, Autumn," the senior attorney continued, "We thought she could learn a lot working with you."

"Of course, Sir, my pleasure," I said then turning to Autumn and extending my hand, "Nice to meet you." neither of us letting on like we had met before at Cole's bar. Her blonde hair pulled back wearing glasses and a business skirt hand heels. Over the next few weeks and months we established a great working relationship and any thoughts I had of a sexual nature were pushed aside I was now her boss and mentor she was my young intern. But she is great to look at her gorgeous body, her cute pampered feet, those dazzling green eyes.

Sometimes I felt like she was flirting even teasing me, crossing and uncrossing her legs, leaning over my back to look at documents. I dismissed those thoughts, although her image became a regular friend at play time.

Chapter Four-The Lakeshore Tavern

Setting up for my regular Saturday night gig, doing a quick sound check, a couple of hours before I was set to perform. I looked out from the stage at the empty bar only a few regulars playing darts and drinking. There was Autumn swaying like before in her Grateful Dead tee shirt, ripped faded jeans and those yellow flip flops.

She waved and I smiled at her but my mind was thinking this is going to be trouble. When I finished my preparation I got my favorite craft beer from the bar and ducked into the green room. Longing on the sofa legs up, shoes off, sipping my beer there was a knock on the door and in walked beautiful Autumn.

"HI, you here with your boyfriend?" I asked hopefully.

"No, we had a fight," she continued, "so I thought I would come hang and watch you play."

Like I said trouble with a capital T. "Have a seat sweetie," I said without really thinking or maybe Cheri was doing the thinking and not Cheryle. Autumn slipped of those cute yellow flip flops and sat facing me on the sofa. I had been here before this scene as always turned out and burned out the same. Lost in desire or lust or maybe I was just horny we were soon making out on that old cruddy sofa.

Driven by her beauty stroking her cheek as my other hand slip down her body over her braless breast lower still unbuttoning her faded ripped jeans. Sliding my hand inside her jeans to find her thong soaking wet. Fingers finding there way inside her wet pussy playing her like a fine instrument hitting all the right notes, fingering the cords.

Her pleasure sounds filling my ears in a beautiful melody. The playful act of two women making love our cloths coming off two gorgeous naked bodies coming together as one. Laying on the sofa in a beautiful sixty nine position. Tasting Autumn as she taste me our sex sounds filling the room, Auralism at it's best, a beautiful melody of sound.

A perfect moment months in the making since that first night at Cole's bar life is beautiful in it's randomness. This would change things forever between us a beginning an a end. My pussy grinding into her tongue as my long tongue strained to go deeper inside her smooth pussy. A grand crescendo coming, panting, moaning in a sexual delight.

'Knock Knock' "Cheri five minutes," came a voice from outside the door. Shit, how long had we been at it? Dressing quickly, taking the stage, barefoot, Autumn's pussy juices still on my face. Called to the spotlight again for the best set I ever played. Autumn watching me perform swaying has only she can move.

Chapter Five-After the Show

laughing, giggling, drinking, on the sofa in the green room her smooth legs stretched out her gorgeous feet finding my lap. I caressed her smooth legs finally working her feet I prodded each cute foot, digging into the soft balls of her feet. Knuckles enclosed around her soft toes popping them lightly. Sucking each toe in my warm mouth working my tongue around them. Her moans telling me I was on the right track.

I was loving every minute of servicing her lovely feet, reading my mind, she removed her top exposing her gorgeous breast. Her hands sliding inside her pants pushing them down exposing that beautiful hairless pussy I needed to taste again. I crawled between her legs, licking my way up, flicking her clit with my tongue. She manage to free her legs from her pants wrapping them around my head, pushing me down, fucking my face, my long tongue exploring her insides. Her smooth pussy felt wonderful, her scent filling the air, her moans grew louder.

Her hands in my long red hair, her pleasure flowing through me, my tongue straining, juices dripping down my chin. Her body shaking in delight, I lingered there, finally crawling up her body slowly, finding her lips we kiss fervently.

Chapter six-Life at the Office

After crossing the line with Autumn we carried on a torrid affair. She would spend the night at my apartment two or three times a week. I tried to keep things professional around the conservative law firm but Autumn was becoming more brazen. I knew the affair could not continue so I set a late meeting with her in my office after everyone would be gone.

Better to do it in the office keep it professional then risk doing it at my apartment and backsliding. Sitting at my large oak desk I waited for her running over my words in my head.

"Take a seat Autumn," I offered waiting for her to sit before continuing, "Autumn I have loved the time we shared together but I have noticed it is affecting our work," pausing for effect, "my job is to help you become a good attorney and I'm failing you in that department."

"No, Cheri, you have been great," she whimpered tears in her green eyes.

"This is what I am trying to say a subordinate should not address me in such a manner," starring at her sternly I continued, "so it would be better for both of us if we end our sexual relationship and went back to a strictly professional relationship."

"Pleas no," she whimpered, "I'll do anything you say, I love you."

In that moment something stirred inside me a lust but more then that power. A strange feeling for a lady still recovering from an abusive relationship and break up.

"Stand UP!" I ordered in a stern voice not sure where I was going as she stood up standing on the other side of my desk, "Remove your panties SLUT!"

Autumn followed my orders reaching up her skirt and sliding her red panties down her smooth legs and stepping out of them. I walked around my large oak desk picking up her panties, "open your mouth slut," cramming her own red panties in her mouth has she opened it.

Her green eyes wide open tears trickled down her face as I starred at her with a mixture of disgust and lust. Bending over my large desk pulling Autumn's skirt up exposing her bare ass cheeks. I smacked her ass hard leaving a bright red hand print smacking her again again till her ass burned red. Her muffled cries exciting me as leaned forward whispering in her ear, "will you respect me around the office now?"

She nodded her head but I wanted a verbal response so I removed her red panties from her mouth. "Yes!" She screamed

Smacking her ass again I screamed "Yes What!"

"Yes MA'AM," Autumn answered me, "I worship you teach me."

Chapter Seven-Excepting My New Role

Our late late night meeting had not gone as planned but had a wonderful effect on Autumn. Her behavior was strictly professional again she is a very intelligent young woman and was a valuable asset to my practice. Her visits continued to my apartment as I excepted my role as her mentor and teacher taking us both to new dark wonderful places.

"No no..." I yelled in a commanding tone. "Crawl Bitch!"

Autumn dropped to her knees moving slowly with her naked rear end in the air she crawled slowly toward me. I was in control of young intern living out my darkest fantasy. I presented my cute little left foot to her mouth, ridiculously slow, her tongue began tracing the tips of each of the toes on my foot I watched in amazement as my she serviced my cute little foot. I'm not even completely certain as to what she did with her magic tongue It was that good. At some point, her tongue swirled around each toe and she sucked my big toe into her mouth all the while flicking it gently with her tongue.

"That's perfect, Bitch, clean my feet!" I encouraged.

When her teeth sank gently into the arch of my foot, a searing white light of heat pulsed through me and I was growing incredibly wet. Autumn reached up as my knees parted and her fingers found their way to my wet pussy. The entire area was throbbing and exploding with pleasure.

As her middle finger stroked my swollen clit, I stared down the sweet little blonde submitting to my kinky desires. She stared back with her big green eyes, pure lust written on her face. Setting my left foot down, she turned her attention to my right foot, picking it up, she began teasing and torturing my toes with her sweet mouth much in the same manner as she had the left.

I lifted my left foot and slipped it between her legs. My toes found Autumn's hairless pussy. My foot began to rub her and I marveled that she was as wet as I was. She gasped as I felt her hips move against my foot. Ah, so that was what she wanted the dirty slut. I smiled and began to retract my foot. She moved with me trying to keep contact and I continued to retract. I pulled my right foot away from her mouth and she looked up, completely confused.

Standing and turning around, "Lick my Ass! Bitch!" I command.

I felt Autumn's tongue flick at my tight asshole, I was so turned on exerting my control over her, slightly surprised by her compliance and willingness, did she want this along? Standing in front of my full length bedroom mirror, seeing her knees behind me, sending shivers throughout mt body.

She eagerly attacked my ass with enthusiasm, I felt her tongue licking my asshole, spreading my cheeks with her hands. She poked her tongue inside probing my tight ass, while I watch the whole thing play out in the mirror, she fuck my dirty ass with her tongue. My fingers finding my swollen clit, rubbing, watching her eat my dirty ass, orgasm building. My body began to shake, as her tongue explored my bowels. screams escaping my lips, body shaking my legs thrusting my ass into her face.

Pulling away I sat on the bed breathing heavy Autumn moved up between my legs, her tongue tracing wet trails along my thighs. I was certain I would burst when she finally touched her tongue to my swollen clit. The initial shock was so powerful my intern on her knees naked licking my swollen excited clit as I jerked uncontrollably in pleasure. Autumn continued, my hips began moving with the rhythm of her tongue. It was an incredible experience. She was so soft and gentle and yet so passionate and eager. When she slipped her finger inside of me while her tongue continued to tease my clit, I exploded with an earth moving orgasm so intense that I thought I might burst into a million pieces.

She continued to lick and suck soothingly as I came down from the cloud of orgasmic bliss I had ascended to and looked up at me like a puppy that had just obeyed a command and was now eagerly awaiting a reward. I pulled her up on to the bed so that she was straddling me and I took her face in my hands, kissing her softly and loving so that I could taste myself on her lips.

"Stand up you stupid Bitch!" I told her.

Laying her naked little body across my lap caressing her ass cheeks tenderly. teasing Autumn, before beginning her spanking. Hearing her screams and watching her wiggle on my lap as my hand strikes down hard on her beautiful ass with force turning it bright red.

My secrets revealed.... Thank you for reading my story.

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4 Comments
lostopportunitylostopportunity11 months agoAuthor

Thank you for the feedback I love hearing from the readers Cheri XOXO

AnonymousAnonymous11 months ago

Yeah didn’t care for the switch either. Could you rewrite perhaps a different ending? Us romantics are longing for one …

PappasleazePappasleaze11 months ago

good story, well written. I personally would rather seen Cheri summit to her intern, but isn't my story to tell. thanks for another good one.

AnonymousAnonymous11 months ago

It was going really good, till the abrupt switch....

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