Jessica and Her Five Brothers


Dad always did have a soft spot for helpless strays; stray dogs, stray cats…and stray women.

I remember the day he brought Amber home to ‘stay with us a while.’ The lithe woman with a pretty face and long lush hair couldn’t pay my father for the repairs he’d made to her car. She’d been evicted from a cheap hotel so she came to stay with us. She entered our little stucco house on a cooling summer night with a backpack and a baby tucked away in a baby seat.

Jessica Day Osborne entered my life as a wide eyed wiggling bundle in a pink fleece onesie when I was six years old. A few months later, dad and Amber got married in Las Vegas and we all became a family.

I remember Jessica toddling around, always happy and laughing and later, when she was older, I’d catch her poking around my room looking for what, I don’t know. Being a rough boy, Jessica fascinated me with her cute innocence. To me, she was my precious kitten. She was too innocent to sense the tension building between my father and his second wife.

Amber had become restless. Saddled with two kids and my father’s demands that she be a respectable housewife were more than she bargained for. I think she was eager to get back to her stripper alley cat life as dad tried to set her right.

The day my stepmother Amber drunkenly popped the curb as she came to pick me up from school is still etched in my mind. She wreaked of alcohol. She yelled at me to get in the car. Feeling protective, like a big brother should, I opened the back door and removed five-year-old Jessie from the car seat and told her that we’d walk home. She kept yelling at me to get my ‘stupid little ass in the car’ and I kept saying ‘go home, you’re drunk’. And when the pick-up monitor began to approach the drama unfolding in front of school, Amber angrily squealed off. Jessie said she was hungry so I took her to McDonalds and spent the last of my allowance on a cheeseburger. She ravenously bit into the burger. I asked her if she’d eaten all day. She shook her head no, eating so fast I thought she would choke. When dad got home from work, I told him about a drunk Amber not feeding Jessie. It was their last big fight. After Amber signed the divorce papers, she packed her belongings and drove off with Jessie to Florida and moved in with her mom. Months later, when Amber took off on the back of a Harley with some biker, her mother got custody of Jess. I wanted Jessica back but dad said its best that girls be raised by a female. And when I begged him to go and get her, he snapped at me, “she ain’t blood, boy. We ain’t got no rights to her.” That was the end of that.

When Jessica’s grandmother’s health failed, Jess went to live with an aunt who lived a few miles away from Amber’s mom. Occasionally, dad and I travelled from Arizona to Florida to visit Jess. We’d collect her and take her to Disney World and other amusement parks for a few days. But when she became fifteen, she had her own life to lead with little time for us. Saturdays at the mall with girlfriends became her world. The visits stopped but we continued to exchange Christmas cards and continued to keep in touch.

I ended up going to community college where I majored in aviation flight technology, and landed a job in Vero Beach, Florida installing navigation and radio equipment into small aircrafts. Jess and I now live less than one hundred miles from each other. She’s going to college and works part time as a lifeguard at a waterpark and part time at a student job. And though we lived close to each other, we never visited each other. So, it came as a surprise when she contacted me on social media and invited me to a party she was throwing. She practically begged me to come. And though I said ‘yes’, she contacted me twice afterwards to make sure I was coming. I could never tell her no.

With a six pack of beer in my hand, I knocked on her apartment door. Jess answered.

With a bright, white toothy smile and her big sparkling sky blue eyes, she exclaimed, “Luke!”

“Hi, Jessie.”

She threw her arms around me and I returned her hug before standing back at arm’s length to take a look at her. Like her mother, who was a beautiful woman with long legs and high cheek bones, Jessica had grown into a very attractive young woman. She wasn’t willowy slim like her mom. She was shorter, curvy and busty. She had shapely legs, honey blonde hair and looked pretty in a blue mini-dress that fluttered mid-thigh. I was a bit surprised she looked so wholesome like a fresh faced cheerleader without an ounce of skank.

All I could say was, “Wow, look at you. You’ve grown!”

“I’m an adult now,” she replied with a bubbly smile. “Come in, come in!”

I entered her apartment to see two surfer looking blond haired guys sitting on her couch playing Fallout 4 while another one, sitting in an oversized chair, was scrolling and texting on his phone. Another stocky guy, in jeans and a t-shirt, emerged from her bathroom. The music was playing, candles were lit and bowls of chips sat out untouched, but other than the six of us, there was no one else in the apartment.

“Gosh it’s good to Side Escort see you,” she said, leading the way to her little galley kitchen. “You can put your beer in the fridge.”

The stocky guy joined us in the kitchen to open the fridge and take out a beer.

Jessie said, “Luke, this is Trevor. Trevor, Luke.”

We exchanged a quick ‘hey’ before Jessie left us alone. I placed my six pack in the refrigerator and grabbed a bottle before closing the door. Trevor popped open his beer and handed me the opener.

“Thanks man,” I said, popping open the beer. “So how do you know Jessie?”

“I’m her brother.”

“Me too. Well, step-brother.”

“Yeah me too. Her mom was my dad’s second wife.”

“Mine too. God, Amber was a piece of work. Wonder what ever happened to her.”

“You didn’t hear?”


“Amber is serving time.”

“What’d she do?” I asked, not a bit surprised.

“What didn’t she do. Her shit head boyfriend robbed a gas station in Georgia while she was waiting in the car smoking meth. There was a high-speed chase with cops and they crashed into a minivan full of kids. She was convicted of robbery and drug possession. She had prior convictions of drug possession, burglary and writing bad checks, so she’s serving time. Hag got five to seven.”


“She deserves it. She was a total bitch to me and my dad.”

“She wasn’t a bitch to me. She just didn’t care. Its amazing Jess turned out so straight.”

“No shit,” he replied as we admired her from a far. She was bubbles and sunshine.

Trevor smirked and said, “I hope they keep Amber’s ass locked up.”

“I hear you, man.”

We clinked bottles, toasting to our step-mother’s incarceration and drank. We looked around at the other two guys, jock looking dudes flicking their fingers over the controllers while the other, a collegiate looking guy kept his gaze upon his phone.

Trevor said, “Man, I hope some chicks get here quick.”

I nodded. I wouldn’t mind making friends with a hot girl or two.

Jessie returned to the kitchen to refill her cup with wine as Trevor left to take a seat in the living room. After sipping her drink, she looked up at me and said, “I remember I always nosing around in your room. Sorry if I was a pain.”

“You weren’t too bad.”

“You saved my life. Going to live with aunt Krystal was the best thing that could’ve happened to me…other than you and your dad. How is he?”

“He’s well. He still has the auto shop but he’s thinking about selling. He’s ready to retire, buy a bigger boat, and fish his days away on Lake Havasu.”

“I loved going to Lake Havasu. Boating with you guys were some of the best days of my life.”

A buzz erupted from her intercom.

“Excuse me,” she said as she left to answer it.

She buzzed in her guest and answered the knock that soon followed. A guy entered the apartment. He looked a bit rough, lanky with scruffy black hair and wary eyes.

“Shane!” she exclaimed as she gave him a hug he didn’t reciprocate.

He scanned the room, sizing up the guys to see if he could best them in a fight. Shane entered and set his beer down on a side table. They exchanged a few words as they separated and she left him to rejoin her other guests. He ripped a can from the six pack rings and popped it open. Jessica turned off the music and then the TV.

She stood in the middle of the room and said, “Okay, everyone is here. Whew. Alright. I can’t believe it. All of my brothers in in room.”

We all glanced at each other.

“Half-brother, cousins, step-brothers,” she stated. “It doesn’t matter. You’re all like brothers to me.”

Shane said, “So what is this? Some kind of family reunion?”

She giggled. “Something like that. See, you’re the only guys I trust. See, I have a secret fantasy I want to do with you guys. I want to have a gangbang and I want it to be with you guys.”

Our collective mouths dropped in that deathly silent room. Then, with a big goofy smile on his face, one of the guys on the couch pointed at her and said, “Ha! April Fools! Good one, Jess.”

“No, Cody, I’m serious, you all. I actually forgot it was April Fools’ Day. Anyways, I want a gangbang with you guys like those porn videos where a girl is on a table and takes on everyone.”

Shane said, “What? Like all at once or one at a time?”

“I said ‘gangbang, not pull a train. What? I know the difference. I want like double penetration. That really turns me on. I want you guys to treat me like a piece of meat.”

I’m ashamed to say I was chubbing in my pants listening to her describe porn. I glanced around at my distant relations. Their eyes were glazed over, enthralled by Jessie about having all of her holes filled at once.

“Shane, Cody, Drew, Trevor, Luke; I trust you guys. It’s not like I can get on Tinder and ask a bunch of strangers to fuck me at once. They might kill me or sex traffic me, rob me or something. So how about it?”

She untied her dress’ sash and the wrap-around dress fall open. I was surprised to see she wasn’t wearing Side Escort bayan panties or a bra and that her tits, topped with pale pink areolas, sat up like that naturally.

With a wry grin, she asked, “You guys up for a little fun?”

Trevor said, “You’ve got some issues, Jessie.”

“Maybe,” she replied. “You can leave if you like. No one is keeping you here.”

She got down on her knees. Looking up at him she said, “You can leave or you can stay and have your dick sucked. I saw you watching me sun bathe and beating off in your bedroom.”

We all glanced at each other again but no one made a move for the door.

She asked, “Want me to get it started?”

She reached out to the nearest guy, Shane, and unzipped his pants. She took out his dick and began to suck it in slow languid pops. Then she let go of it and crawled over to the couch where she unzipped Cody and Drew’s pants. They shifted to make it easier for her to get to their dicks and she took then out, sucking one while jacking off the other while the rest of us watched. She went back and forth between the both of them until their dicks were glistening and hard. When she let go, they took their dicks in their hands to stroke themselves as she crawled over to Trevor. He just stood there as she sat up to unzip her pants. I was mesmerized by her behind; the roundness of her butt cheeks and the slit of her pussy lips dusted with cashmere pubes. She took out Trevor’s semi-hard dick and put it in her mouth. Her head bobbed back and forth and his hands went to stroke her silky hair. When she released him, she looked up at me. Something told me to stop her, but I couldn’t. She unzipped my pants and reached in. My dick lurched as her fingers grasped it to pull it from my clammy underwear.

She said, “I can’t tell you how much I love having dick in my mouth.”

She opened her mouth and slid her lips down my firm shaft. Her firm but yielding tongue felt incredibly good as it caressed my shaft in velvet. I looked around to see everyone staring and stroking their dicks. Then I looked down at her to see my hard dick stretching the corners of her little mouth. Her lips released me with a slurpy pop. I wanted more.

Shane approached. Cody and Drew got off the couch to join us. She took Shane’s dick in her mouth. Her hands instinctively reached for the nearest dicks on either side of her, grabbing Cody and Trevor’s in her hands where she pumped her hands back and forth. We surrounded her and she went around and around to suck us. Then she stood up.

“I want you to wear these ski masks when you come in,” she said, holding up the black knit hat before placing it back on the pile. “There’s one for each of you. It’s part of my fantasy. And don’t cum in me. You can cum on my face or my ass or on my tits, okay? Good.”

She sashayed into her bedroom, leaving us all standing there glancing around at each other, wondering if one, two or all of us would enter or leave. Without a word, Shane stepped out of his basketball shorts, pulled the balaclava over his head and walked into her room.

Pulled into the room by lust and wonder, I picked up a balaclava and slid it over my head. Adjusting it over my mouth, eyes and nose holes, I kept repeating, ‘I’m just going to watch, that all’ as I stepped through the door.

Jessica laid on top of her comforter face up as the guys, naked from the waist down, looked down at her while masturbating. I noticed a vibrator and a bottle of lube on the nightstand beside her bed. I stepped out of my jeans and underwear to join them beside them. I gazed down upon her nakedness. She was ready to party.

With her innocent eyes set upon us, she asked, “Well who’s going to get the party started?”

We all glanced at each other, standing their masked like a bunch of pervs.

When no one moved, she said, “Okay.”

She grabbed the vibrator from her nightstand.

“I’ll start the party myself,” she said as she turned it on. It’s buzz filled the room. “You can stand there pulling your puds all day if you want. I’m going to get off.”

She slid the long vibrating bullet between her thighs. Pressing it against her clit, she closed her eyes and moaned as she rode the vibrations.

Shane moved over to paw her tit, rubbing it and pinching her nipple. I watched it stiffen beneath his fingertips. He grabbed her face by her cheeks to turn her mouth to the side. She opened her mouth and he stuck his dick inside and moved it in and out a few times before he finally, pulled it out. He moved his body on top of her then pulled her legs apart by hooking her legs under her knees. She tossed the vibrator aside and waited with wide open eyes. He took his dick and prodded her pussy lips with its head before shoving it in. She moaned in pleasure as Shane began to fuck her. I stood there, my dick tightly gripped in my hand as I watched.

Shane flipped her over on her hands and knees and the bed rocked as Cody crawled onto it. On his knees, Cody position himself in front of Jessie’s face. Pointing his hard dick her way, she readily opened her mouth Escort Side and accepted it all the way in. Shane grabbed her ass as he stuck his dick back inside her. She groaned a bit as her pussy and face got pumped by two dicks. After a minute or two, Shane pulled her off of Cody, flipped her onto her and after straddling her torso, he furiously jerked his dick over her face. She opened her mouth and grabbed her own tits, pushing them together, to tease him. As he continued to jack off, Drew moved closer. He slowly stroked his dick as he stared at her pussy. Then he slowly slid in one finger into her wet pussy only to withdraw it to slide in two.

“Fuck!” Shane yelled as he jacked his hard dick. He threw his head back as jizz spurted out from him to land in viscous white threads on Jessica’s forehead and hair.

Shane stroked out dribbles and spurts of jizz before collapsing on his back beside her while holding spent dick. Jess wiped the cum off with a nearby tissue and tossed it aside before reaching out to grab Trevor’s dick. She jerked him for a little while before he reached for the lube and squirted some on his dick before letting her go at it again. She didn’t let go when Cody pushed her knees up to her breast before sticking his dick into her open pussy. His pelvis slapped against the back of her thighs as he pummeled her with punishing hard thrusts. Jess took it like a pro, still jacking Trevor’s hard dick from base to head. Then Trevor leaned into her face. He grabbed a handful of her hair and jerked her face towards his dick. She leaned into his crotch, taking his stiff member into her mouth. Trevor held her head in the awkward position as she bobbed her head over his hard flesh.

By now, my dick was heavy and throbbing for release.

When Cody finished, cumming on her tits, I pushed her aside to join her on the bed. I laid back before lifting Jess up by her waist to straddle me. She took my dick, aimed it up and eased herself onto it.

“Arwwww!” I groaned as her warm moist tightness enveloped my hardened flesh.

Eyes closed, she moaned with pleasure as she rode me, bouncing up and down on top of me a few times before Drew crawled behind her and forced her forward. Her boobs mashed into me and I remained still as I heard the gloppy sound of squirting lube as Drew squirted some into butt hole. Jessica’s opened mouth uttered no sound as he pushed his dick into her tight anus. The pressure threatened to push mine out and took some might to keep myself deep inside her as Drew pushed further up her tight bung hole. Jessica’s cheeks were flushed a rouge pink and she held onto me as Drew thrusted in her tight slippery hole. My head lolled to the right to see Shane watching us and playing with himself as we lay shoulder to shoulder.

“Oh, oh, oh,” slipped from her mouth each time thrusted into her.

His dick rubbing against mine separated by a thin membrane of thin slick skin felt like nothing I’d ever felt before. I held her tight enjoying the weight of her boobs smashed against my chest.

“Oh God,” she said. “I’m going to cum. Oh. Oh. Oh yes.”

Drew exclaimed unintelligible words as he jammed it all the way up her ass. I felt dick pump and throb as he came in her ass. Then Jess ripped off my mask and as we gazed into each other’s eyes, she kissed me with her hot open mouth. I almost blew my load as Drew ripped his dick from her. Drew stumbled aside and I lost sight of them all as I closed my eyes while Jess and I kissed. Our tongues moved in a frenzy against each other before she broke away. I opened my eyes to see Trevor haul her up off of me to position her onto her hands and knees once more. Getting on the bed, he shoved his dick into her mouth. I maneuvered behind her. Just the sight of of jizz dribbling from her ass made me feel so nasty. I entered her once more. Slapping my hand against her butt cheek as I pumped her wet pussy from behind like a mad man. My balls tightened. I couldn’t hold it in another second. I withdrew from her pussy before easing my dick into her little asshole. It was still so tight, constricting my dick when I was all the way in, and my hard-on just exploded inside of her. I growled as my hands gripped her hips. i rammed it in balls deep and came inside her, pumping hot jizz which had nowhere to go and its warmth welled around my dick. When i was spent, i withdrew and got off the bed. I backed up, still watching as Drew pulled up behind her, rubbing his limp dick against her pussy lips.

I needed fresh air and stumbled out of her room. I grabbed a beer from the fridge before collapsing on the couch to cool down. I opened the beer and began to chug it, looking over my shoulder at the bedroom of sin.

It wasn’t until a little before midnight when Jessica finally said, ‘no more, I’m done.’ We all left her lying face down on her bed.

Trevor ripped off his ski mask, put his pants back on, swigged down a beer, checked his phone and left without saying a word. We all sat around in the living room drinking beer. Shane pulled out some weed and rolled a joint, turning on the tv to play Halo 4. Cody joined him while Drew checked his phone. I pulled on my pants and for some reason, I was concerned about Jess. She didn’t’ come out to join us so I got up to check in on her. She was where we left her, naked, face down in her pillow. Bruises were starting to form on her ass and hips.

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