Autumn My Intern

Prologue:

Listening to reader feedback I changed the ending for all the romantics out there, thank you for reading my stories all feedback welcome love hearing from the readers.

I'm Cheryle "Cheri" an Irish Catholic, Attorney, Singer-Songwriter thirty year old bi-sexual woman five foot-two 102lbs. with long red hair and cute little feet-💋 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 stayed there licking soothingly, finally crawling up her body slowly, finding her lips we kissed fervently.

Chapter Six-Sex at the Office

Autumn on her knees under my large oak desk she starts on my cute little feet teasing me licking and kissing them. Sucking on my toes driving me wild from under my large oak desk. Her hands reaching up under my Devinci skirt pulling my red lace panties down over my smooth legs. Moving her face into my red bush, eating my wet pussy with her long tongue. Grabbing her hair pulling her in, biting my lip to hold in my delight, has her long tongue works it's magic. On her knees under my desk bringing pleasure, a much needed release from my young intern, Her face and tongue buried in my wet cunt.

My legs trembled and shook, my head was spinning, it was similar to my body falling off a cliff into a pile of tingling ecstasy. It's was a sense of sensual release that I fond myself having no control over and letting myself go because it's was just too damn good. An earth-shattering orgasm at work breaking into a million little pieces. Not thinking about anything else besides my own pleasure all-consuming and euphoric electric dominoes falling down in different directions under my skin.

Chapter Seven-The Affair

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. In the mornings we would run along the 18-mile Lakefront Trail. one of the most spectacular urban runs in the country, gorgeous views of Lake Michigan and the Chicago skyline, urban beaches, marinas, and beautiful parks, passing by some of the city's famous and beautiful cultural institutions. The trail is lit making it perfect for pre-dawn runs while it is still dark.

My favorite run is Chicago Street at Navy Pier to McCormick Place Convention Center, seven Miles in length. This beautiful trail parallels the heart of downtown and the Magnificent Mile, and includes sights such as Navy Pier, Grant Park, the Museum Campus, and Soldier Field where my favorite team plays, the Chicago Bears. Lots of great sights, but the trail can be crowded on a nice day, that is why we run in the early morning. The trail is particularly spectacular around the Museum Campus, where we can pop off the main trail and do a spectacular loop around the tip to the Adler Planetarium.

There are even additional trails along Northerly Island Park. Edgewater Beach to Navy Pier seven miles in length. The northern terminus is at Edgewater Beach, and runs along the water passing Foster Beach, Montrose Beach, and Lincoln Park. A little more bucolic with a gravel running path in parts. McCormick Place to Rainbow Beach Park, eighteen miles. South of the Convention Center area are several gorgeous miles with wonderful waterfront views, featuring Prairie Shores, Burnham Park, and Promontory Point. There are some fantastic skyline views headed north from Promontory Point. Trails in Jackson Park, paths around the University of Chicago Campus, Midway Plaisance (59th St.) west to Washington Park.

We run and talk taking in the sights and sounds of the beautiful lakeshore. A great way to start my day before heading to the office or court. Of course are runs always end with a hot soapy shower for two. A great morning workout routine, turning on the hot water, I sat on the toilet to pee, as the bathroom filled with steam.

Autumn walking past me, her gorgeous young naked body, flowing blonde hair, amble breast, a heart shaped ass and her cute little feet. Climbing in the hot shower, soaping her body, what a beautiful site.

Climbing in with her, washing Autumn's back with my soft soapy hands, reaching around washing her breast with the hot soapy water, I tease with her hard soapy nipples, taking my time, as I let my hand slide down slowly over her flat stomach over her smooth pussy to her soaking wet pussy lips.

Rubbing softly, caressing, washing, the soap so slippery, making love to each other, letting my wet soapy fingers play with with her swollen clit, rubbing softly. Inserting one then two fingers inside her, kissing as she does the same things to me. Slowly moving in and out, our desire growing with each thrust. Our soapy fingers making a slurping sound as my fingers thrust in then out. The hot water, the steam, lust, mixing to make a beautiful morning.

Tingling all over with sensory pleasures, legs spread hot water trickling down my ass crack sending shivers up my spine. Teasing, playing with each each other, nearing a shattering orgasm, moaning, pulling back, moving my hips to meet her soapy slick fingers plunging into me. My body dancing with pleasure, a magnificent feeling, our scents filling the bathroom. Slowly dropping my wet fingers down the crack of Autumn's ass to her little brown flower rubbing my soapy fingers on her tight little asshole. Probing the entrance, gently, poking one wet finger inside her ass thrusting so deep, she lets out a audible sigh. Then out, then in, adding another wet soapy finger and a third driving hard pounding her ass, which she loves, deeper and deeper. Autumn's fingers rubbing my wet soapy swollen clit as the first waves of sheer pleasure start encompassing me.

The hot water, a bathroom full of hot steam, our own little sauna. The pain and pleasure, the depravity, of fucking her sweet ass. The dirty little blonde slut I love so much, as Autumn screams in delight, I drop to my knees for a taste.

Autumn is so wet my long tongue exploring her sweet insides. Curling, dancing, tasting her juices with my long tongue. Autumn grabbing my head, legs trembling. knees buckling, "YES! Cheryle YES!"

Squirting in an erupting orgasm all over my face I linger there savoring her taste. A great start to my day. An out-of-body experience I can feel my clitoris on a roller-coaster ride but my soul and mind are on a whole other level of connection taking over my body with my gorgeous Autumn.

Chapter Eight-The Beautiful View

Two to three nights turned into six or seven Autumn had woven herself into my life, my thoughts, I was falling in love with my young intern. On the balcony after a Thursday day in court. Hands exploring her tight young body, rubbing, caressing, a building heat between us. A sexual lust in the crisp lakeshore air passionately groping each other laying on one of my zero gravity lawn chairs on the tenth floor balcony.

Arms, legs, fingers and feet converging into one package of playfulness and fun. Shedding our cloths two naked bodies making love in the brisk Chicago lakeshore wind. Kissing passionately tongues intertwined in an erotic dance her wonderful tongue. Rubbing her breast, teasing, playing with her hard nipples, lowering my mouth to bite her nipples playfully.

Pinching Autumn's hard nibbles as she rubs my swollen clit a fun, playful, erotic game. Exploding with a sexual lust playing out the wonderful moment with her sweet moans drifting out over Lake Michigan floating out in the night air. Two becoming one in a magic moment of crazy wild fun.

Swinging around, to find Autumn's beautiful warm wet pussy inches from my mouth, straddling her sweet face, lowering down on her mouth, feeling her long tongue on my wet pussy, her nose in my soft red bush, sweet sixty-nine a sensory pleasure. Her scent is intoxicating driving my wild lust, tasting her wet cunt, sweet pussy juices covering my face, grinding into Autumn's mouth a sensory delight.

Feeling her hands grab my ass cheeks pulling me down into her waiting warm mouth, Muffled moans filling my ears, raising her hips to meet my long tongue, our sex sounds filling the night air, my long tongue deep inside Autumn's wet pussy curling, twisting, my fingers playing her clit like a fine instrument strumming the cords fingering the strings bringing her sweet cries of extasy.

Working in unison for our mutual pleasure, giving, receiving, a beautiful rhythm coming together. The smell and sounds of sex surrounding us in a whirlwind a tornado coming. Bucking and grinding enjoying the sweet ride her tongue plunged deep inside my wet insides.

Come with me sweet Autumn my young love, the big climax, follow my lead, time to fulfill are sexual needs. Orgasms crashing over us like the waves of Lake Michigan crashing on the shoreline. Faces dripping with pussy cream, cries and screams of delight, bodies shaking, cute little toes curling, pure pleasure radiating throughout us.