From Pretty to Plain

It was a hot summer in Miami.

Sam walked across the street from her apartment to the beach.  She didn’t need much.  The bag over her shoulder had a towel, her phone, and some sunscreen in it.  Her body was mostly bare.  She was wearing her tanning bikini, if you could call it a bikini at all.  The sheer thong had clear straps and three tiny pieces of fabric to cover her nipples and tidy pussy slit.

Sam never heard anyone complain about her outfits.  She was absolutely stunning.  At 25 years old, 5’10, and 140lbs, she’d been exercising hard and following a perfect diet since her young teenage years, sculpting a long, lean, strong physique.  Her tiny waist, gently curved glutes, toned legs, perky B cup breasts, and sculpted upper body were almost a caricature of female athletic ideals.

She found a spot, laid out her towel, and took her sunglasses off, showing her brilliant blue eyes, framed by perfectly shaped eyebrows, to the sun.  She gathered her butt-length, naturally light blonde hair in her hands, and twisted it into a messy bun on top of her head.  She thoroughly sprayed herself with sunscreen, set an alarm on her phone, replaced her sunglasses on her delicate face, and took a nap.

 

Brian tossed his workout shoes back in their spot and walked out of his enormous home gym, into the long hallway leading to the basement steps, sweat soaked shirt hanging loose in one hand.  He felt life coming back into his legs as he passed by door after door.  He felt a little burn in each step of the climb as the lactic acid started releasing its hold on his lower body.

He got to the main floor of his sprawling house, headed to the kitchen, and pulled a protein shake from the fridge.  A few drops slid down his stubbled chin and landed on his bare chest.

At 6’4 and a ripped 250lbs, Brian was a specimen of a man.  Ten years prior, people had called him crazy for opting to pursue business goals instead of entering the NFL draft, where he was projected to go in the first round.  Now, he was a forgotten name in that world, and was only really known to few as the broker who made the biggest real estate and yacht deals in the region work.

He picked up the phone.  “Miami?  Tonight?  Yes, let’s close it.”  He set the phone down, walked the seemingly endless distance to his master bedroom suite, and got in the shower.

 

Brian showed up to dinner in downtown Miami that evening, dressed in a great fitting pair of khaki pants, with a tailored button up shirt.  He approached a table overlooking the bay, shook hands, ordered a drink and food, and got down to business.

 

“I’ll get the next round,” Sam said to her friends.  She walked up to the bar in a stunning fitted blue dress and heels, hair braided over one shoulder, makeup perfectly done.  She watched as a tall, athletic man shook hands and said goodbyes, and hoped he’d notice her.  He did.  She flashed him a smile and gently played with her braid.

“I’m Brian.” The man said in a smooth voice, extending a hand.  “What brings you out here tonight?”

Sam took his hand.  “Samantha, but you can call me Sam.  Just here with a few friends for a drink or two.”

Brian didn’t miss the perfect posture, the low cut dress with the slit up the side, or her tall, toned body.  He also didn’t fail to notice her eyes and long, luxurious hair.

 

Sam didn’t introduce Brian to her friends.  Maybe that was a mistake.  Instead, she brought the drinks over, had a few sips, and excused herself to meet Brian at the valet.

She wasn’t even drunk.  She’d only had one drink and a few sips of a second, but she immediately really liked this guy, and found herself looping her arm through his and fiddling with the long braid falling past her breast.

A deep blue BMW M8 convertible appeared at the curb, and a second valet opened the passenger side door for Sam.  “This is a beautiful car sir,” the smiling valet said as he took some folded bills from Brian.

Sam slid into the black leather passenger seat, glad her hair was braided.  The V8 let out a low burble as they smoothly pulled out into the street, Brian clearly taking care not to upset his cargo.

“How far away do you live?” Sam asked.

“Outside Naples.” Brian replied.  “I’ll have a driver take you back tomorrow, unless you decide to stay longer.”

“Isn’t that almost 2 hours away?” She replied.

Brian explained the business deal he’d just done, and that he traveled all over the state to broker 8 figure and above transactions.

As they left Miami, Brian closed the convertible roof.

The talk was light.  Sam felt comfortable.  Brian felt confident.  Then they arrived at Brian’s home.

The first thing Sam noticed was the gates opening.  There was a long driveway through palms, gumbo-limbo, and live oak trees that completely obscured the view of the house from the road.  Then the sprawling house came into view, strategically lit to highlight its contemporary architecture.  Hints of grandeur, but balanced and not over the top.  Overall, she was impressed.

With the car parked in the garage, they walked into the house.  Brian opened a bottle of white wine, offered some fruit and cheese, and the two sat and talked for hours, before heading to the bedroom.

Sam wasted no time slipping out of her dress.  Her perky breasts didn’t need a bra, and she made a bit of a show of removing her lacey thong panties.

Brian watched, thoroughly entertained, before Sam came over and helped him out of his own clothes, revealing a hard bulge under his briefs.  She quickly released his throbbing, smoothly shaved cock and took it in her mouth, before pushing him back onto the bed and sliding her hairless pussy onto him.  Brian’s expert hand released Sam’s long braid from its binding, and took a fistful of her hair, pulling her gently toward him, kissing her, and nuzzling his face into her long blonde mane.

 

Sam woke the next morning to the smell of coffee.  She found a robe folded on the nightstand next to her and put it on.  Then she went to the kitchen to find Brian preparing breakfast.  “Have some food.” He said, motioning to eggs, turkey sausage, and toast he’d prepared.  She sat down at the expansive island, and Brian pushed the plate toward her.

“I’ll be doing a quick workout after breakfast, if you care to join.” He said.

“I don’t have any clothes to wear to the gym.” Sam replied.

Brian had a big grin on his face.  “That’s the nice thing about a home gym.  You don’t need them.  If you’re uncomfortable, you can borrow something of mine, or I can go naked too.”

Brian led Sam to the basement.  She was more than a little surprised to see one in South Florida.  At the bottom of the stairs, there was a long hallway, and the ceilings had to be ten feet high.  All of the walls, the ceiling, and the floor were smooth concrete, aside from a long runner carpet down the middle.  They passed door after door, before coming to one at the end.  Brian opened it to reveal a huge home gym, full of free weights, machines, cardio equipment, and even a turf runway.

Sam kept eyeing Brian’s nude body as he went through his circuit workout.  She was on the stepper machine herself, nude, watching.  Before she knew it, he was done, and she was bent over a bench, taking an absolute pounding and begging for more after, which he gladly gave.

They came upstairs, and Sam was surprised to see a housekeeper cleaning the breakfast dishes, wearing a fitted navy blue t-shirt tucked into a white tennis skirt.  Overall, she looked very plain, with blue eyes, unmaintained brows, a tall, but stocky figure.  Most surprising was her hair, or lack of it.  Her head was shaved bald, with just a slight shadow where there would be hair if she let it grow.  She seemed very nice, though.

“Sam, this is Liz, my housekeeper.”  Liz gave Sam a warm smile and shook her hand.

The day flew by.  Chatting, swimming, laughing, lounging poolside behind the house, and fucking.  Before Sam knew it, the sun was setting while she slowly rode Brian on a poolside chair as he ran his hands through her damp hair, moaning softly.

“I’m so sorry.” Sam said.  “I didn’t mean to overstay my welcome.  I can call an Uber or something.”  She really wanted to stay, though.

“No, no.” Brian said with a big smile.  “I can call my driver, but it’s getting late if you want to stay tonight.”

The days went by.  Sam never went back to Miami.  She gave up her job, and told friends she’d be out of town for a while, but not to where.  Brian was gone a day or two a week to make a deal, but otherwise worked from his home office.  Sam spent her days working out and lounging in and by the pool when he was gone.

Then Brian proposed a deal.

“Sam, I have a proposal.”  He said.  “You stay here, and be mine.  I’ll treat you as mine, meaning I control what you do, what you wear, what you eat, etc.  In return, you live here for free, and be with me.

After working out the details, Sam agreed.  She almost felt like she was just drifting along with his current, as if she was on autopilot.

Things changed slowly at first.  Brian put Sam on a different diet and workout program.  He had her eating more, and doing different workouts.  Out were the pilates, light circuits, booty building workouts, and cardio marathons.  In was lots of weighted side bends and powerlifting, with a big upper body focus.

A month later, Brian’s plan for Sam’s hair came into light.  Sam protested at first, saying she had a stylist in Miami she’d prefer to use.  Brian reminded her of their deal, and it was settled.  Brian’s stylist came weekly to refresh his hair, and would cut Sam’s monthly.

The first month it was a few inches cut.  The next, it was a few more.  Sam really didn’t notice it much at first.  She just felt good going along with anything Brian suggested.  She actually felt lucky that a fancy stylist was doing her hair every four weeks.

Sam didn’t even notice that her hair didn’t touch her shoulders anymore, or that her perfectly shaped brows had returned to a fully natural form.  She was busy in the gym, going heavier than ever on upper body workouts, side bends, and working up to max reps on the new torso rotation machine.

The food was increasing.  Her lifts were increasing. The frequency of her haircuts was increasing.

Brian had changed Sam’s haircut schedule from monthly to weekly, to match his own.  It was a weekly dusting at first, then a quarter inch a week, then a little more.  She never really noticed the change, since there were no mirrors in the house.  She just went along with it.  She didn’t notice how much wider her waist was getting, or how many dozens of pounds she’d gained.  She only wanted to do what he said.

Sam didn’t question it at all when Brian moved her things to a bedroom suite in the basement.  She didn’t even consider the concrete walls or the insulated steel door that locked from the outside.  She didn’t think about the little bowl cut she had that barely brushed her eyebrows, or the smooth shaved undercut.  She still got to fuck him in the master bedroom, and even got to sleep with him there some nights.  She didn’t even think about the fact that she hadn’t seen her cell phone in months.

 

Sam was sitting in the chair, smiling, while Brian’s stylist cut her hair.  He turned off the guardless clippers, and brushed the loose fuzz off her shoulders and stubbled head.  She got out of the chair to feel her nearly bald scalp, just as she had last week, and watched as Liz sat down.  The stylist did the same to Liz, running the bare clippers over every inch of her head, erasing a week’s growth.

Sam and Liz cleaned up the hair, and went to Brian’s shower.  Brian lathered both of their heads and shaved them smooth, before fucking Liz, then Sam.  Sam loved haircut day, because Brian always rubbed her slick, bald head and told her what a good girl she was.  Sometimes she and Liz even got to sleep in his bed on haircut day, instead of in their basement bedrooms.  If they were lucky, Brian would let Sam and Liz play with each other while he watched and stroked their bald heads and thick bodies.

 

Kirsten took Brian’s hand as he helped her out of the seat of his convertible.  She tucked her long blonde hair behind her ear.  She didn’t know why, but she felt very safe with Brian, and almost attached to him, despite having only just met.

Brian led her into the kitchen, where two stocky, bald housekeepers in blue fitted t-shirts and white tennis skirts were tidying up.  Kirsten’s first impression was that they looked rather plain, and a bit heavy set, but nice.  The matching bald heads was a bit of a surprise, but she thought it suited them.

Brian introduced her. “Kirsten, these are my housekeepers, Liz and Sam.”  They took turns shaking Kirsten’s hand with warm smiles, then got back to work as Brian led Kirsten to his bedroom.

Liz and Sam could hear Brian’s voice as he walked away.  “You know, Kirsten, you can stay as long as you want.”  They looked at each other and smiled.