Angela’s Situation

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This story is a sequel to the previous roommates stories I wrote. I intentionally streamlined the number of named people actively in the story this time so as not to cause confusion or distract from the main story line.



Angela broke down the last moving box and stacked it next to the recycling bin with the rest.  It had been two years since she’d graduated and left the college house that she’d called home for 3 of her 4 years at the University.

She’d just landed her dream job with a larger firm based in Fort Lauderdale, and was excited at the possibility of increased personal freedom.  Her first job out of college had been a great stepping stone, but she’d been treading extremely carefully, letting her hair grow longer to put in to a neat bun, avoiding coloring it, and in general trying to seem as plain and professional as possible.

She went in to the bathroom to brush her teeth before bed, and looked in the mirror.

“How did I get so boring?” Angela said to herself.  A few years prior, she’d been the most daring one of her friends, with a shaved undercut and constantly changing hair in both length and color.  Then, by the time they graduated, she was the boring one.  Her roommates Sue, then Jen, and finally, Lisa, had all gotten super short haircuts, and even shaved their heads, while her own hair grew out.  Now, she looked at her pale blonde hair, kinked from being in a ponytail all day, falling over her shoulders and landing atop her modest breasts.

Angela walked in to the office the next day, her first at her new job.  With her black skirt, black shoes, dark stockings, white button down shirt, and hair slicked back in to a tight bun, she was the picture of professionalism.  She set her shoulder bag on her desk and pulled out her laptop, before hearing a voice.

“You must be Angela.”  Said a voice from behind her. “I’m Arthur, but you can call me Art.”

“Arthur Briggs?  The CEO?”  Angela asked, jokingly.

She turned around and looked the man up and down.  He was the picture of a big city businessman. Tall and fit, with a chiseled face, and long brown hair that he wore in a brief ponytail, Angela found him strikingly handsome in his sharp suit.  She suddenly turned red, realizing her mistake.

“Please just call me Art.”  He said with a smile.  “Let me know personally if you need anything.  Don’t be shy.”

Angela was in a bit of a state of shock.  Five minutes in the office and she was afraid she’d insulted the biggest boss.  How could she forget her research?  She knew the CEO and chairman of the board was surprisingly young, at only 30 years old, but she’d been caught off guard when he’d introduced himself so casually.


Handsome, young, and rich, Art was very desirable.  Many of the women and a some of the men in the office had words to say about that.  Angela had had her fair share of thoughts about him as well.  “What would it be like, to be with a man like him?”  She knew she was considered pretty, if a bit plain, and she knew she was fit from miles upon miles of running and so many hours on the spin bike, but what could she ever offer a guy like that?


It was two months later on a Friday afternoon that Art caught the elevator door as it was closing in front of Angela. “Mind if I join you, Angela?”

Angela was a little surprised that he remembered her name.  The company had nearly ten thousand employees across several states, and she was just a mid level financial advisor that happened to have a desk on his floor at headquarters.

“Not at all, sir” Angela replied.

He frowned, brushing his hair back with his hand.  Angela noticed that it was shorter than before, no longer long enough to all fit in a ponytail.  “Art, please.  Sir makes me feel old.  We’re only what, six years apart, aren’t we?”

Angela blushed, unsure of what to say.

“Angela, this may come off as too forward, but what are you doing tonight?  I have two tickets to a show, and no one to bring.”

“You, with no date?”  Angela asked, incredulously.  Before she could say another word, he laughed.

“I’m… picky, let’s just say that.  I’d like to get to know more about you.  I’m also a little… weird… and some might say I have strange taste.” Art replied.  “I’ll pick you up at 8.  I’m sorry, but I won’t have time for dinner beforehand.  Text me your address.  You have my cell number in your Outlook contacts.”

The elevator opened, and Angela watched Art walk to his forest green Porsche 911 GTS, almost in disbelief at what had just happened.


Two and a half hours later, Angela heard a knock on the door.  She’d just finished curling her blonde hair and had put on a sleek blue dress that complimented her light blue eyes and fit, athletic figure.  She took one last look in the mirror, almost surprised at how pretty she looked in something other than white and black dress clothes with her hair pulled back.  Then she donned her heels and walked to the door.

“Good evening, Angela, you look lovely.”  Art said, taking her hand and leaning over a bit to kiss it.  Angela blushed at the compliment and old fashioned gesture.

“You look quite dashing yourself.” Angela replied. “You changed your hair!”

“”Do you not like it?” Art replied, running a hand up his bald neck. “With the weather getting warmer, I figured it was time to get rid of some more of it.  I haven’t had a short haircut in a few years.”

Angela took in the new look.  His long hair had previously been long enough to put most in a ponytail.  Now, it had been cropped short, bald faded on the sides and back, the top slicked back.  She found herself strangely aroused by the thought of him getting it cut.

“Love it.” Angela replied.  “I used to have a similar cut a few years ago.”

“Really?”  Art laughed. “I would love to see that.  I don’t mind shorter hair on women.  Do you have pictures?”

They got in the back of the Mercedes-Maybach S650 and Angela pulled out her phone. “Just remember Art, these are from college.  I didn’t exactly keep a professional appearance then.”  She handed him the phone.

“Wow, you really did pull that off well.  You look really sexy, if I’m being honest.”  Art handed the phone back after looking at the last picture for a little while.

Angela looked at her phone to see a picture of her, with her hair at its shortest, sides and back shaved bald, the top a short mini bowl cut ending an inch above her ears and eyebrows.  Then she saw Art adjust the crotch of his pants, and thought she saw the outline of an erection underneath.


The evening went on smoothly.  Art was much more down to earth than Angela expected. He was also very interested in her, and less interested in talking about himself.  At the end of the night, before he could bid her farewell, Angela threw her hands around his neck and pulled him in for a kiss, running her hands over his freshly faded scalp.  Art returned the kiss, before wishing her a good night and heading back to the car.

Angela woke to her phone ringing the next morning.  Who would be calling her so early?  She picked up her phone to see that it was 9am, and Art was calling her, of all people.

“I know it’s bad form to call so soon after a date, but I wanted to invite you somewhere.  Don’t worry, I can get your time off approved through Wednesday for you.”

Angela was worried.  Time off?  She had clients.  How would that work?

“Meet me downstairs.  I’m out front.  We have some things to do first.”  He hung up.

Angela scrambled to make herself presentable.  She hurriedly threw on some clean leggings and a sports bra, put her hair in a messy bun, and grabbed a clean t shirt before running the stairs 5 stories down.

She reached the door and looked out to see Art, parked in front of her building leaning against a deep blue Aston Martin convertible.  He was the picture of cool.  As she walked to the car, he opened the door for her to get in, admiring the way the leggings showed her off.

Art started the car.  Before putting it in drive, he turned to her with a serious look on his face. “Listen, Angela… I like you.  I’ve had my eye on you since you started working for us two months ago.  I’m sorry if that’s creepy, but I’m a man who tends to know what he wants when he sees it, and I know I want to spend more time with you.”

Angela relaxed, putting her hand on his arm and smiling.

“One more thing.” Art continued. “I saw those pictures of you with short hair last night.  I want that, too.  If that’s too much to ask, then that’s fine.  I understand if it weirds you out and you want to get out.”

Angela put her seatbelt on. “I’m still kind of new in town, you know.  Do you know a good salon?”

Art smiled, then threw the car in to gear and they roared off toward downtown.

Angela sat in the salon chair, watching as Art spoke quietly to the stylist, Becky, gesturing a bit with his hands and pointing at pictures on his phone.  Angela had agreed to let Art choose the style.  She wouldn’t know the result until the end.  Finally, the stylist said “okay, easy enough!”  Becky walked over to the salon chair Angela sat in and spun the chair to face the front of the salon, where Art stood, watching.

After spraying, combing, and sectioning, Angela heard a pop followed by a humming noise, and felt a chill.  She knew she should expect clippers, but it had been years since she’d felt them on her head.  Before she could think much further, they were running up her neck, the feeling of the bare stainless steel blades getting warmer after each pass.  She was becoming aroused, an effect she’d forgotten the clippers had on her.

The passes ended lower than Angela expected, though.  Becky pulled the clippers  away at the base of her occipital each time, leaving a clean line from ear to ear, below which only brief stubble remained.  Once she’d gone over the area a few times, Becky placed the clippers back on the counter.  Angela reached back and felt her neck, suddenly wet between her legs as she touched her bare nape.

Becky began combing the remaining damp hair straight down all around her head, before carefully positioning the scissors and closing them on Angela’s hair.  Foot long blonde strands began falling to the floor.

Angela felt the cold scissors position at the base of her neck.  “Longer than I expected.”  She thought.  She watched as Becky chopped off most of her length, giving her an angled bob that followed a line about an inch below her jaw, ending below her chin in the front.

After a little layering, shaping, and a quick blowout, Becky was done, and spun Angela’s chair back to face the mirror.

As the cape was removed and shaken off, Angela found herself feeling a little underwhelmed.  The cut was expertly done, and looked great, but she had expected to be brought straight back to a brief bowl cut.  Aside from the undercut hidden beneath her hair, the cut was fairly bland.

Art greeted her with a smile and a kiss.  “You look wonderful, Angela.  So much better now that your beautiful shoulders and neck aren’t hidden when your hair is down.”

They got back in to Art’s car and went off toward their next stop, a swimwear boutique.  This was a strange experience for Angela, because similarly to the Salon, she had no input on the decisions.  The employee simply measured Angela, talked to Art, then went in the back room for a few minutes and came out with a modest sized bag, which Art threw in the trunk of the car.

Once that was done, they headed back to Angela’s apartment.  “Can you get your wallet and anything you’d need for a long weekend away?  Don’t be too long”  Art asked.

“Come upstairs with me, we can be quick.” Angela said.

Art parked the car and they stepped in to the elevator together.  The moment the doors closed, Angela grabbed Art’s face and pulled him in for a kiss.  Art then grabbed Angela’s butt and easily lifted her off her feet, pinning her to the wall so their eyes were level.  She wrapped her legs around him hard and kissed him, as he ran a hand up her buzzed neck and grabbed a fist full of hair.

Art let Angela down as the elevator doors opened, and she took him by the hand and pulled him to her apartment door.

Once inside, Angela turned to Art and pulled his t shirt off over his head, admiring his strong, toned body.  As Art undid his pants, Angela quickly stripped out of her t shirt, her abbreviated hair swinging back and forth, and peeled off her leggings and panties.

The two stood there for a moment in the kitchen, looking at each others nude figures, before Angela knelt and took Art’s erect cock in her mouth.  She only did so just enough to wet it, before turning to bend over the counter and guiding his member between the wet lips of her hairless sex.  Art grabbed Angela by the back of her neck, feeling her buzzed undercut as he thrust in to her.


After a 30 minute open-air drive, Angela’s hair was a mess.  “I wish that it were either a bit longer to put in a ponytail, or short enough not to get in my eyes,” she said, smoothing it back down.

Arriving at a marina, the captain welcomed Art and Angela on to the chartered yacht.  “You’re our only guests, and the crew will show you to your staterooms.  Your clothes are being unpacked in to the closets.”  Angela was in awe of the service and luxury.  As they cast off and left the harbor, Art turned to Angela.

“Angela, I know this is all a bit intense, but I want you to know you’re under no pressure.  I just want you to enjoy the next few days with me, then maybe I can convince you to keep seeing me.”

Angela smiled.  She liked Art.  While he had admittedly been watching her the past two months, she hadn’t told him that she’d been, in a way, crushing on him during that same time.   Seeing what he was providing her, though, and hearing how much he genuinely like her, enhanced her feelings toward him.  As the yacht exited the harbor, she went down to the forward stateroom and opened the closet.

In the closet were several swimsuits, coverups, and sun dresses, perfect for the hot weather.  Angela noticed that the dozen or so swimsuits varied in coverage, from two full coverage one pieces, to three of the smallest, most revealing thong bikinis she’d ever seen.  Smiling, she put on a string thong bikini that failed to fully cover the edges of her nipples, and which had bottoms so small they barely contained both of her small pussy lips.  She put what she could of her hair in a high ponytail, the front hanging down to frame her face, buzzed nape fully exposed, and walked back up above deck to meet Art on the bridge, seeing the coastline disappearing in the distance.

Art had changed to swimwear, too.  His lean build showed off his efforts in the gym.  His defined abs and chest were covered in a stubble of brown hair, his legs toned and fully showing in the briefs he wore.  He admired Angela’s fit body, fully bared in the micro bikini she wore.

Angela pulled him in for a kiss, and Art’s swimsuit couldn’t hide hide how it made him feel.  They each slipped off the little clothing they wore, as Art sat back on the couch, and Angela straddled him, lowering her tight, wet sex over his throbbing member.  Art reached back, stroking her bald nape and grabbing her small ponytail as she ran her hands through his hair.  Angela stroked Art’s stubbly sides and grabbed his remaining hair as she came with him deep inside her.


Angela woke the next morning, in the aft master stateroom’s king sized bed.  Art was missing, though.  She went up the stairs to find Art coming up from the swim deck with the captain.

“I was just setting up a surprise.  Let’s eat breakfast first.”  Art said.  They were quickly served a light breakfast and coffee as Art explained their options for the trip.  “We’re in the Bahamas now, and we have a small tender and a jetski, so we can go to any of the several small secluded beaches.  We can snorkel, jetski, swim, or just hang out on the yacht, you name it.”

Angela smiled, thinking about the beautiful weather and clear water.  “That all sounds wonderful.  I can’t help but wonder, though, what’s the surprise you were setting up?”

“Well…” said Art.  “This is a pleasure yacht by design, but the owner likes to fish.  He keeps what’s called a fighting chair on board, and it mounts to the swim deck.  Come with me.”

They made their way down the steps to the swim deck where Angela saw a polished teak chair with arm and foot rests mounted to the deck. Wrapped around the back of the chair was a narrow shelf with four rod holders in it.  Instead of fishing rods, though, the rod holders contained a small spray bottle, a large plastic comb, a pair of professional looking scissors, and cordless clippers with a few guards and hair clips set next to them on the tray.  Angela’s heart skipped a beat.  This truly was a surprise.

“I figured with all the upcoming activity, you wouldn’t want your hair in the way.”  Art gestured for Angela to sit in the chair.  “Don’t worry.  I was actually a barber for a few years to pay the bills before my big break.”  Angela removed the coverup she wore over her thong bikini and sat in the chair.

There was no cape or paper strip.  Art pulled the hair tie from Angela’s hair and began sectioning.  Then he used the hair tie to make a ponytail at the top of her head, everything else hanging down.  He took a #2 guard from the tray, popped it on to the clippers, and switched them on.

Angela shivered.  It was warm, but she was excited about what was  happening.  There was no mirror, just the view of the gently lapping water and islands in the distance.  Then there was a pop, a humming sound, and the vibrating sensation she hadn’t felt in years along her temple.  She could feel the clippers reaching high along the side of her head before departing and starting again at the bottom, making all of the hair below her ponytail, besides her nearly bald undercut, a uniform quarter inch in length.

Art switched the clippers off and removed the number two guard.  He took the bare clippers and began creating a high bald fade all around Angela’s head.  She shivered feeling the warm steel blades on her scalp, and felt herself become sopping wet between her legs.  Her juices dripped on to the teak deck below.

The clippers were deposited back in the rod holder, and Angela felt the hair tie being pulled out again, followed by hair falling over her face and the sides and back of her head down to her chin.  She hadn’t said a word to Art since breakfast, but she was enjoying every moment of this shearing.

Art began wetting Angela’s remaining hair with a spray bottle and combed it through.  He picked up the scissors and Angela heard the audible “shhhnk” of scissors slicing through air.  Angela had assumed that Art would cut a bowl cut like the picture she’d shown him, but he wasn’t combing hair down and cutting a line.  He was pulling the hair upward and seemingly cutting it just above his fingers as they were pressed to her scalp.  She held in a moan as her pussy throbbed.

Art efficiently reduced Angela’s hair to less than an inch at her fringe, and shorter toward the back, where he left barely half an inch.  He picked up the clippers again, placing the #2 guard back on and running them up the back of her head and over her crown, then used a comb to guide them as he blended the top and sides until Angela was left with a sleek cropped micro pixie.  Barely enough hair was left on top to comb.

“I think that’s sufficiently out of the way.”  Art said.

Angela stood, clit throbbing, trembling slightly. She ran her hands over her head, feeling the short hair and soft stubble, then she turned to Art, took the clippers out of the rod holder and took the guard off.  Without a word exchanged, Art moved to sit down.  Before he could settle in the chair, Angela began plowing the bare clippers down the middle of his head, the remaining few inches of hair tumbling to the teak deck.

The clippers went silent as Angela dropped her miniscule swimsuit in to Art’s lap.  She walked around to face him, now completely nude.  Art admired how Angela’s newly shortened hair accentuated her neck and fit body as she came to face him.  She pulled his briefs down and mounted him in the fighting chair, lowing her engorged pussy on to his hard cock, and rode him harder than she’d ever ridden before as the hot Carribean sun beat down on them.  Covered in sweat, hands all over each others hot, sun drenched heads and bodies, they stepped off the swim deck in to the crystal clear water.

5 responses to “Angela’s Situation

  1. This was fantastic! I love how she gets to experience multiple cuts and I like the micro pixie that she ends up with as well. Great job! They’re going to need plenty of sunscreen for their newly exposed scalps!

  2. John, what a marvelous story, and so eloquently written. I loved the balance of sexual tension and the introduction of Art’s fetish for short hair. You have a gift for descriptive writing. I can’t wait to read more.

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