The Tryouts Begin (Pete's POV)

Author's note: This chapter's on the shorter side compared to the other stuff I've posted on this branch. That's because I thought I'd add more to it, but haven't really been writing anything for a while now. So I figured I might as well post this instead of continuing to let it sit in my drafts.

I feel a sharp pain shoot through my hand as I complete this last sentence. Then I give in to my body's limitations and drop my pencil to indulge in a much needed break. As I shake my hand in an attempt to free myself from this cramping sensation, I read proofread what I had just written out loud.

"Old Rule: If a student of Jefferson high school does decide to take the job of the faculty member they're dating, their partner will be demoted to the student's personal assistant and will be payed half of their previous salary."

After confirming that nothing is misspelled, I begin looking around at my surroundings. Although the room's main lights have been shut off, my desk lamp is bright enough to provide me with a clear view.

My visual scan begins at the floor where a small pile of clothes, consisting of lingerie and a pair of boxers, lay at my feet. Looking up reveals a digital clock resting on the desk's shelf lets me know it's two in the morning. Once I note the time, my gaze sweeps around the spacious master bedroom and lands on the king sized bed situated behind me. Laying under the covers is my mother, who's lightly snoring as she sleeps completely naked.

A few hours ago, I was plowing my cock into her soaking wet cunt. That's how I normally end my nights since obtaining the rule book. However, I found myself restless tonight and couldn't fall asleep despite the heavenly comfort of using Mom's fat tit as a pillow. My mind just wouldn't stop replaying events from yesterday, from toying with Ms. Roma to shoving my crotch in Mrs. Gray's face. Then there's Principal Hudson. She was the primary reason why I had trouble sleeping. Finding the potential in the scenario I crafted for her to be endless, my thoughts started racing with all kinds of fun ideas. As I laid in bed, I contemplated how I wanted her story to continue. So after spending some time rolling around, I hopped out bed, sat my desk, and opened up the rule book.

"Ah- shit!" I mutter when the cramp in my hand is joined by a new one in my neck.

I turn my head back to look strait ahead, rubbing my neck to sooth it, and the clock fills my gaze once again. The cause of my sudden pain becomes obvious upon realizing I've been looking over my shoulder to stare at Mom for several minutes. For all the mind controlling I do, it's kind of ironic how easily I get hypnotized by her huge rack.

My second glance at the clock also reminds me of how late it is. I really want to just sit back and enjoy my day tomorrow, not having to pull out the book in-between each scenario I craft. Determined to make that happen, I've spent quite some time coming up with all sorts of rules for Principal Hudson and other's I'll be seeing at school.

Taking one final glance over the pages I managed to fill with text, I feel satisfied enough to finally get some sleep. That is until another idea pops into my head, causing me to pick up my pencil one more time.

A soft groan escapes my mouth as I wake up from a deep sleep. I only open my eyes slightly to prevent being overwhelmed by the sunlight shinning through the window. While the bright light forces me to come to my senses, it's not what pulled me out of my dream. That credit goes to the warm feeling around my cock coupled with the repetitive 'glruk, glurk, glurk' sounds echoing through the room. It's a pleasurable sensation that I've grown accustom to enjoying every morning.

Once my eyes are able adjust to the light, I gaze down at my laid out body and see a large lump poking up from my bed sheets. Peeling the covers back reveals my naked mother. Despite being discovered, she continues to diligently suck my morning wood.

"Morning, Mom. Oh, that's good. You're really making up for not slobbering on yesterday's morning wood, huh?"

Upon hearing my voice, the amazonian MILF lying in between my legs removes my cock from her mouth and looks up at me with a delighted smile.

"That's right, baby. You always give me the biggest loads right after you wake up. It's like your balls spend all night getting ready to bust in my mouth."

She gives my balls a few licks, as if thanking them, before looking back up at me and continuing to speak.

"I love it when you have me wake you up early. It means less time I have to wait to gobble your fat fuck-stick!"

As Mom goes back to sucking my cock, her response prompts me to check the time. It does seem that I'm getting another early start today. Well, I should say early for me since it's currently 11:30 AM. After taking a moment to remember why I requested this wake up time, mom draws my attention by popping her head up once again.

"Oh yea, and you've got some visitors. Principal Hudson and her family are waiting for you downstairs. They're dressed kinda funny and her husband keeps talking about how 'Big Booty Judy is ready to work her big booty'. He said you'd know what that means."

I chuckle from imagining Mr. Hudson saying that line, filled with enthusiasm as his wife prepares to spend the day as my trial-girlfriend. It takes a second for me to calm down before I respond as Mom resumes sucking me off.

"Yea I know what he's talking about. Alright, I'm gonna bust in your mouth. Once we're done here, go downstairs and entertain our guests. Have Cindy eat your asshole, keep her head buried deep in your crack. I want you to put on a good show, so twerk in her face. Your cheeks should be really smacking her cheeks. Got it?"

Not wanting to stop sucking my cock for a third time, Mom simply nods with my meat in her mouth. I move a hand down to cup the back of her head and start thrusting my hips upward. As always, the mature woman takes it like a champ and only gags occasionally.

After filling my mother's mouth with cum, I send her away and head to the bathroom. I break out into my second smile of the day when I hear Mom aggressively shout my sister's name and command Cindy to lick her ass. I finish showering, throw on a pair of jockeys, and go downstairs when it's around noon.

"Daaamnn! You can really move the junk in your trunk, Mrs. Sanders!" a female shouts while I'm on the stairs.

A chorus of laughter follows the comment just as I reach the ground floor. Then I walk into the living room where I'm pleased to see quite a bizarre sight.

In the middle of the room is Mom and Cindy. Just as I instructed, my sister is on her knees taking the full brunt of our naked mother twerking in her face. However, this has become somewhat of a normal occurrence. What really peaks my interest is the site of Principal Hudson's family sitting on my couch.

"Hey everyone! I hope you're enjoying Cindy's booty licking show!" I call out while glancing over their clothes.

Seated on the side closest to me is her daughter, Olivia. The girl is dressed in full dominatrix gear. A black latex tube top wraps around her modest sized chest, leaving her tight stomach exposed. Her lower half is clothed by a short skirt and high heeled boots that reach up to the middle of her thighs. Both of these are mad out of the same latex material as her top. Her look is made complete by a black chocker.

Judy Hudson, my principal, has her fat ass planted on the middle cushion. Her outfit is pretty much a slutty schoolgirl costume. A mostly unbuttoned white blouse is tied in a knot just below her chest, pushing her tits together. The ample amount of cleavage and nipple outlines make it obvious she's not wearing a bra. She is also wearing a skirt, but her's is plaid and made of a regular material. A pair of normal looking black heels are strapped on her feet.

Finally, Simon Hudson is resting on the far side of the couch. He appears to be wearing the coaching out outfit he was telling me about yesterday. His top half consists of a white polo shirt, a red baseball cap, and whistle hung around his neck. Simon's lower half is dressed in mid-calf socks and sneakers. The Hudson family's patriarch is the most bizarrely dressed because he doesn't have any pants or underwear. Only a pink chastity cage locked around his flaccid penis.

"Oh hi, Pete!" Judy yelps in a giddy tone the entire family stands up upon seeing me.

I open my mouth to respond, but Simon beats me to it giving his whistle a quick blow before shaking his head in disapproval for a second. Then he crosses his arms and begins scolding his wife.

"C'mon, you know that's not how to address him. We went over this! You might be in love with the boy, but you're not his girlfriend yet. Now start over and show Pete that Big Booty Judy is ready for her first day of tryouts!"

The mature woman blushes with embarrassment and nods her head. Then she turns her back to me, shifts her feet until they're shoulder width apart, and bends down at the waist. Her skirt rides up to reveal her lack of panties. Finally, she reaches her hands back and spreads her plump cheeks to give a clear view of her pussy and asshole.

"Big Booty Judy reporting for duty, Mr. Sanders!" She shouts throughout the room.

My principal's obscene display gets a chuckle out of me as well as her daughter. A smug grin spreads across my face as I walk up to my 'potential girlfriend'.

"At ease, Booty." I say, giving her presented ass a sharp smack.

She lets out a yelp from the contact that amuses me. Then she quickly releases her asscheeks, stands up, and turns around to face me. A meager expression spreads across her face as her eyes look downward. Combining that with the hands clasping together in front of her, it's obvious that she's unsure of how to act.

I look to my side where Mom and Cindy's performance is still going on. It's hard to tell how my sister is feeling with her face plunged into Mom's ass, but I can tell our mother is starting to feel fatigued. Her twerking has slowed down, bucking her hips at a more moderate pace, and her forehead is matted in sweat.

"Mom, that's enough. Go up to Cindy's room, find a notepad and a pen, and get on her bed on all fours. Cindy, go get me one of the collars and leashes from our sex toy stash. Then you're gonna join Mom and continue practicing your ass licking skills. You two will stay like that until Mom writes 'My Son Is A Well Hung Stud And My Daughter Is A Stupid Ass-Licker' 300 times. If either of you have to pee, just let that out. It's Cindy's bed, after all, so it's already pretty nasty. After you finish, you can get on with your normal day."

My family disperses to follow their orders. There's a few moments of silence until Cindy meekly hands me the requested items and scurries away. Then you hand the collar and leash to Mr. Hudson before making a motion indicating you want him to secure it around Judy's neck. The way he complies with my nonverbal command so eagerly brings a smile to my face. I actually have to stifle a chuckle when attaches the leash and holds up the other end to me, essentially offering me ownership of his wife.