Manic Monday

Caution: This Erotic Sex Story contains strong sexual content, including ft/ft, Teenagers, Consensual, Hermaphrodite, White Female, Oriental Female, Oral Sex, Anal Sex, Pregnancy, Cream Pie, BBW, School, .

Desc: Erotic Sex Story: Manic Monday - Sunny Skye is set to became a rich and powerful heiress on the night of her 18th birthday. The one stipulation she faces is that she must marry one of her current seven girlfriends in order to receive her full inheritance. With her birthday less than 2 weeks away, does Sunny have time to find true love while keeping her undying desire for sex satisfied? Probably not. But you might have fun watching her try.

"Monday..." I groaned into my pillow. "Who the fuck has ever actually liked Monday?" I always seem to enjoy the most pleasurable dreams on that first morning of the week but by the third punch of the snooze button, the memories are so foggy I can barely remember them. Though the memory had faded, the rigid evidence of my arousal remained. I was having my way with someone; A teacher—a cheerleader—maybe a tennis player. It's of no real consequence whom. All that mattered now was at 6am, the alarm was blaring again and I was debating with myself between going back to bed or finishing myself off manually and soiling my sheets.

I rolled over slightly, firm buttocks bracing me as I glided my petite first between my delicate thighs and gave a squeeze. A smile flexed away my early morning grimace as my flesh I fondled began to pulse in reaction. "Ah!" I folded my legs and clasped them shut. My heart throbbed as I stroked myself—maybe Monday wasn't going to be so horrible after all.

"SUNNY!" the unmistakable shrill of Emmy the housekeeper wilted my pleasure. "SCHOOL!"

"I hate Mondays." I growled under my breath as I buried my face into my long blonde hair.

I'm probably getting ahead of myself—I'll start over while I get ready for school. My name is Sunny Skye—isn't that horrible? I'm neither a professional wrestling valet nor burlesque dancer. It also makes me seem perkier than I really am ... even if I'm captain of my cheer team at my high school. Wait a minute—scratch what I said before. My name is PERFECT.

Speaking of perfect; so is my future. My 18th birthday is in two weeks. At that time, I will come to inherit the prestigious Cloudy Skyes Candy Company. At 65 years, it's one of the oldest businesses around, and sorta an institution here in Pom City. Personally, I'm pretty stoked to be the 5th generation of the Skye family to hold the reigned of the million-dollar business.

I paced through the foyer of the Skye mansion and had to cover my face as those horrid ultraviolet rays pierced through the sun-lit glass ceiling. Despite the alliteration, I actually hated my namesake—especially on Monday. Sweat beaded on my brow instantly as the sun scorched my fair scalp. Through this terrible inconvenience I stepped lightly, the pleated skirt of my school uniform made audible swishing sounds as I scurried to the town car.

"Thank you, Manfred." I murmured as our family driver held the door ajar for me. He's a gentle, kind, older man that had served and kept the Skye family's confidence since before I was born. That may seem like an easy task, but we are no normal family.

I slid into the backseat and fanned my thighs. An uneasy sigh drained from my lungs. The morning's severe lack of privacy had taken its toll. "Manfred," I called through the tinted glass that parsed us. "I wish to be alone once she gets in."

"As you wish, Miss Sunny." Manfred was always the first to sign-off on my impulsive flights of fancy. That's why I love him. I thanked my driver with a smile as the car slowly rolled from the driveway past the decadent estates of our neighbors. They were philanthropists, politicians, and pillars of industry—the tangible representation of keeping up with the Joneses. It would all be my destiny—very soon. I was to be a pillar, rigid and firm, with the weight of the world to be on my shoulders alone. Another uneasy sigh rattled my tiny frame. To be truthful, sometimes I thought it would all too much to bear by myself.

I guess that's why my parents added "Sunny's Sunset Clause" to their wills. I guess it was a failsafe incase I was ever orphaned like I was. I wish I could thank them for that one day. Hold on. I haven't mentioned the clause yet? God, this really IS Monday. Don't worry; I'll get to that later today.

The clanking and booming outside the window jerked me from my parental daydream. Construction and traffic horns told me we had made it to the city. This route we traveled daily, full 30 arduous minutes out of our way. It was usually worth it, however. Especially today.

Her frumpy curves caught me eye at the car edged the curb. She awkwardly slid in when the vehicle halted, carefully keeping her thick legs pressed together when her uniform skirt made its obligatory ride up her ass. I giggled to myself as she pulled the fabric back down again. I don't know why she always insists on being so modest.

"Good morning, Miss Skye." Cassidy Black settled herself next to me on the wide seat, pushing her slipping dark-rimmed glasses back up on her pudgy face. "Did you have a good weekend?" She swung her backpack to the floor before slamming the car door.

"Good weekend," I confirmed as I unbuckled my skirt. "Bad Monday." I crept the bottoms down around my shapely hips as I went on. "As usual, I was unable to afford myself time for refocus this morning." A chill from the car's AC raced down my bare legs as my blonde pubes were exposed to the brisk air.

Cassidy nodded with straight lips. Her fingers were about to buckle the seatbelt when she let the strap retract. She knew she wouldn't be needed any restraints other than me. "I was anticipating such a morning for you, Miss Skye." She rose to her knees and hovered over me. "How would you like me today?"

I flashed a Cheshire-sized grin for the first time that day. "On your side, if you don't mind." My heart pounded. I was a kid in a candy store (if you'll excuse the pun) as I watched Miss Black recline and hike up her skirt. Sweet! Her plump loins glistered with excitement. She was always so prepared ... slick, pantyless, and freshly shaven. Cassidy never fails to please ... my most trusted personal assistant and confidant. I finished sliding off my own skirt and gripped my erect 'secret' with a firm hand. My blood swirled and boiled now—no more chills as I pushed my pulsing member into my friend. A satisfying moan gargled from deep within my throat as her warm wetness wrapped about me.

Cassidy grunted as she cocked back one of her meaty legs and winced only slightly when my bulging cockhead penetrated her. I wouldn't say I'm gargantuan or anything, but my 7 inches often proved overwhelming to my many girlfriends—but never Cass. With shuteyes and pursed lips she took each thrust and even pushed back with lustful conviction. She dug her nails into the soft leather of the backseat each instance I slammed into her deeper. Each lunge thereafter sent my swollen family jewels slapping against Cassidy's doughy inner thigh and I could feel every blubbery jiggle through my own muscular legs. 'If we did this more often, ' I thought to myself between darting humps, "I'd have you in shape in no time."

Soon, Cassidy's grunts became groans. As the liquid evidence of her excitement coated my flesh, her throaty groans became high-pitched yelps—borderline screams. She was losing control—slowly but surely. I would have noticed sooner if not for my own deep panting. Good on Manfred for not running off the road in spite of the distracting carnal symphony playing behind him! I rolled my lover onto her belly and continued my assault. Now my smooth, hairless sac was free to box at her engorged clitoris.

"Miss. Skye. MISS. SKYE!" Cass' voice climbed higher each attempt of her broken speech. The way her tightness graduated from caress on my shaft to a violent spasm, I knew my assistant was having a cum. She shaking girl grinded her legs together and kicked off her shoes. I turned back to watch her cute toes curl and flex in ecstasy. Bringing out the foot fetishist in me brought a greatly welcome tingle to my loins. I wasted no time in quickening my thrusts. Cass was just cumming down from her climax when I grabbed two handfuls of her chunky globes. I spread her cheeks wide and to my eyes' delight examined her sopping hole was oozing with her cum. Tiny strings of her schoolgirl jism connected the sides of her pussy like telephone lines.

"Oh. God. You. Slut." I hissed with a stutter. "I know you feel my cock twitching inside you."

"mmhmm..." Cassidy murmured. She had buried her face in the seat as she came to screaming conclusion.

"You're—" My breathing was so erratic I got light-headed. "You're so messy already you shouldn't mind if I—ah! AH! FUCK!" I meant to announce my orgasm—really, I did. But the seed boiled up my shaft so quickly it couldn't be helped. I slammed into Cass' body with finality and allowed a few ropes of my purebred jism to squirt inside her. Then I frantically ripped my cock from her just as quickly and jerked it toward her well-fucked opening. The next half-dozen jets glazed her slit—then the next six her thighs—until gobs of my baby batter dripped from her thighs to either side of her crotch. I drooled and smiled at my handiwork. She was a complete fucking mess, inside and out. "Manfred," I panted as I cracked the window slightly. "How long until we reach school?" I squeezed the remnants of cum from my cock onto Cassidy's limp foot.

"About 10 minutes, Miss Skye." He announced in monotone. How could he be so calm?!?

"Perfect..." I sighed. "Thank you. Plenty of time to recover, Miss Black." I rubbed Cassidy's round calves until she came to.

"Was that really such a good idea?" Cassidy slowly gathered herself as she reached into her bag, pulling out her trusty PDA and table. "Your clause week starts today."

"I know. I know." I rolled my eyes and fixed my skirt. "Don't worry about me, there's plenty more where that came from."

"I'm aware," Cassidy tried to wipe most of my seed from her slit with a nearby towel. "But Monday is most important." She tapped the glass screen a few times. "Today's date with Sara will set the pace for the week. Plus," She paused as she waddled up her skirt. "I know she's your favorite."

I smirked. She was right. Sara was my favorite by far. I have many lovers. Seven total—one for every day of the week. Thought it sounds crazy, it's actually the perfect position for "Sunny's Sunset Clause."

(See? I told you I'd get back to it).

My parents died when I was very young. Meanwhile, proxies have run the business for a over a decade waiting for me to come of age. I am the sole beneficiary with one peculiar caveat. I have to be married by the time I turn 18. The heir to the Skye empire requires a strong, intelligent, partner to help her make decisions. They should also be prepared to have plenty of sex ... this cock of mine can be VERY distracting if I don't take care of it regularly. Cass knows that more than anyone. If I'm not married before midnight on my birthday, the proxies will continue until I'm 30 ... I might as well be 100 by then!

So here I go—seven dates and spending nights with seven sexy suitors. Then I'll make a decision that changes all of our lives forever. No big deal, right? Right...

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