Rich Uncle

Toby’s legs were now spread open, knees up, his cock, balls, and perineum on full display. The ventilation system’s cool air tickled his armpits.


Rich Uncle Pennybags. AKA Mr. Monopoly. Round, a shock of pure white hair on the sides, completely bald on top. Exquisitely coifed bushy white mustache. Thick white eyebrows to match. His attire in public always the same. Dark suit, pearl grey vest, and an elegant bow tie.

Winston Leonard Day got out of the hired car and trundled into the lobby of the DeSoto Hotel. One of Savannah’s most elegant hotels, certainly amongst its most expensive. Late September, still so hot that the heat rolled off of the sidewalk in waves. The hotel lobby, on the other hand, very white, clean and of course, refreshingly cool. Understated elegance. Not gaudy like some of those crusty bohemian mansions in town. More original art than some galleries. A good number of people were in the process of checking in but, thankfully, everything operated at a noise level just above a whisper.

He made the pick right off the bat. What a happy and unexpected circumstance! He was there when Winston glanced to his right as he approached the registration counter. Standing with another fellow at the concierge desk. He looked to be a teenager. Long dark hair, almost black. Well over his ears, falling into his eyes. Pale skin. Pink lips. Light blue eyes. Around 5’8.” Slender. His ill fitting uniform at least a size too big.

He’d have to find out more, of course. But, the lad looked about right for what he wanted. He silently congratulated himself. At the last minute, he’d impulsively thrown some rope, handcuffs, and a dildo into his luggage. Ya never know, he’d thought.

Check in went smoothly. In less than a minute, he was whisked up to his fifth floor corner suite. Classy, elegantly appointed. A nice sitting room, executive desk, a king size bed in a separate room, and a small balcony overlooking the Basilica.

The conference organizers were putting everyone else up at the Holiday Inn Express, a few blocks away. Good for them! They could have that bullshit! If they wanted him to speak at the fall conference, they would pay for the DeSoto. Alternately, he would consider attending some other time. Maybe. They paid.

He was an American Historical Association super star. He knew it and they knew it. Not one, but two John H. Dunning awards for his books on the American presidency in the Twentieth Century. He was also renowned for his sponsorship of three outstanding PhD. candidates who received the AHA’s Allan Nevis Prize for their dissertations.

An opening reception would begin in an hour. Plenty of time to check out the boy. After organizing his clothes and freshening up, he hit the lobby. Sitting in a luxurious chair across from the registration desk, he pretended to study some notes. Mainly, he wanted to observe the scene while he studied the young man.


Toby concentrated on the computer display, trying to keep up as Wells flipped from line to line, then screen to screen.

His second week on the job, still job shadowing. What luck getting this job! Amazing talent? Good looks? Or, just damn lucky? After casually mentioning to a friend how burned out he was working at Sav-Hil Vacation Rentals, he’d been told there might be an opening at the DeSoto.

An easy on-line application. Toby got an almost immediate response inviting him to a face-to-face interview. He thought he was interviewing for a valet or bellman job. Much to his surprise, the opening turned out to be for a job on the concierge staff.

A couple of days later, he found himself sitting across the desk from the hotel’s general manager, Mr. Thinkwell. Neat, officious. Straight forward questions that Toby tried to answer with a minimum of bullshit.

Alarmed, he watched Mr. Thinkwell pick up the phone right then and there and call Karla for a job reference. Karla, his boss at Sav-Hil. A nasty piece of work. She never spared the opportunity to insert “shit” or “fuck” into every phrase. Toby had never thought of warning her that he had applied for another job. This all had happened so fast!

Mr. Thinkwell only asked a couple of questions. Listening at first, then holding the phone slightly away from his ear. Toby could hear Karla’s non-stop barrage from where he was sitting.

“Thank you very much.” Then, in a sing-song voice, “Good-bye.” Thinkwell carefully placed the phone receiver back in its cradle, holding it by two fingers as if it were a venomous snake.

“Well…” Mr. Thinkwell clasped his fingers together on the desk. He looked appraisingly at Toby. Much younger than he preferred for a position like this. But, he saw this as potentially a long-term hire. He could have gotten one of the other guys he’d interviewed. Older, more polished. But, those kinds of guys usually helicoptered in from Miami or New Orleans. Stay a season or so and they were off to Vail or some place in Europe.

Sitting in front of him was a Bee, code for a native of nearby Tybee Island. He could be a stay-er. Moreover, Toby had told him he was enrolled in the hotel management program at Savannah Tech. Thinkwell liked that. He’d guest lectured there himself from time-to-time. Chances are the young man would take the job seriously.

In short order, the offer was made. A significant increase in pay from what he’d been making. Decent hours that fit neatly into his class schedule as a senior at Johnson High School. Monday-Wednesday-Friday from 3 to 8 pm. Every other weekend. Those would be long days but Toby didn’t care. Saturday and Sunday, 7 to 5.

“Parting is such sweet sorrow” wouldn’t accurately describe Toby’s last day at Sav-Hil. As much as Karla bitched him out, he knew he was a valuable employee. He would be missed. With a wave, he bid her adieu.

The words, “You fucker!” formed on her lips. Somehow, she managed to hold back, instead, offering one of her classic glares.

Assigned a locker for his school backpack and clothes, Toby quickly changed into the white shirt and black pants he’d brought with him. The burgundy colored double breasted jacket emblazoned with gold metal buttons was too big but it was the smallest one they had. Sleeves way too long, he was offered a couple of safety pins so he could turn them under. The black clip-on bow tie, likewise a bit outsized, made him look like a little kid getting ready for a church choir concert.

The first couple of days made his head hurt. So many details! To top it off, the hotel’s software, a bit out-dated, seemed counter-intuitive to Toby. He either pushed the back space key too many times or failed to click enter on the correct line. But, the software wasn’t the only challenge.

Mr. Thinkwell scared the shit out of him whenever he stopped by the concierge desk.

“Do tell. How is our young charge doing?”

Mr. Thinkwell had the habit of beginning every question with the phrase, “Do tell.” As a result, Wells had whispered to him, the staff had given him the nickname, Mr. Do Tell. Toby’s funny bone was tickled. The problem was, the name got stuck in his head. He resisted every urge in his body to keep from calling Mr. Thinkwell by his other name.

Even though he was local, Toby quickly came to realize that the upscale Savannah visitor had entirely different needs from those of the average Savannah local.

What’s the best dish at the Olde Pink House? The Fried Lobster Tail. Is it really $60? Yes, and it’s worth it. Shrimp and Crab Meat Au Gratin or Shrimp and Scallop Risotto at Pearl’s Saltwater Grille? He had to contrive an opinion based on the notes on the computer. Toby had only eaten there once when he was a kid. He had a hamburger.

What high end store is closest: Hygge or Terra Cotta? Terra Cotta, but ShopSCAD is even closer and a lot of fun. Toby guessed that directions to Walmart had rarely, if ever, been asked for.

All of this information and more could be found in several binders kept behind the concierge desk. In addition, flipping through the various screens brought up even more information, telephone numbers, and contact names.

Toby watched Wells closely and listened carefully as he made a restaurant reservation.

“Hello, Missy. Wells here from the DeSoto. Looking for a table for two at seven.” Brief pause. “The name is Robert Stevenson. Thank you.” Hanging up, he typed briefly into the computer as he dialed the phone. “Mr. Stevenson, Wells calling from the concierge desk. Confirming two people for seven at Gryphon.” A brief pause. “Will you be needing directions?” Pause. “Thank you. Please let us know if we can assist you in any other way.”

Toby swirled his tongue around in his mouth as he silently repeated some of the phrases. He was blithely aware of how hokey and unsophisticated his hillbilly Georgia accent sounded. This was like learning a new language!

He had to stand silently and just watch for the first week. When he was finally allowed to field a phone call from a guest, Wells stood so close to him Toby could feel his hot breath on his cheek. Heart racing, he somehow made it through.


A bemused look on his face, Winston absentmindedly nibbled on the corner of his notes as he watched the boy. Ideal in so many ways. Looking a bit like a scared rabbit. He watched his associate closely, hanging on every word the guy said.

Every once in awhile, the boy would jerk the hair out of his eyes or sweep it onto his forehead with his left hand. Cute! The light blue eyes and pale skin were really an alluring combination. Winston wondered if he was aware of how pink his lips were.

The ill fitting jacket was almost too much. Obviously too big across the shoulders and the chest. Wrinkles on either side near the armholes concealed what was probably a narrow chest. The over-sized bow tie. He looked like a kid wearing his dad’s clothes. Adorable!

With a sigh, Winston tucked his notes into the inside pocket of his suit coat. Watching the boy had actually given him a mild erection. At his age and under these circumstances, that was pretty good. Standing, he walked past the concierge desk and, without another glance, headed out to the conference reception.


Toby was supposed be off at Eight o’clock. But, the time had come and gone. It had gotten a little nuts in the last hour with a flurry of requests from late arriving check-ins. Wells pretty much stayed on the desk choosing to deploy Toby all over the hotel running short errands and taking care of a bevy of small problems.

Housekeeping, bellman duties, and the concierge function all merged at this hour. Toby helped one new arrival program their room’s thermostat. Another needed specific directions to Forsyth Park’s playground. After trying to explain it to the lady over the phone, Wells marked up a map and directed Toby to deliver it to the guest’s room.

An hour or so of prognosticating was about 58 minutes more than Winston cared to spend. But, it had been good to see some old friends at the reception. The conference would probably yield some measure of gainful knowledge. Returning to the DeSoto, he was a bit disappointed to see the boy missing from his post. Perhaps he was done for the day.

But, when the elevator door opened with a lyrical tone, he found himself face-to-face with him. Toby stepped out of the elevator car, turned to the side, and respectfully held the door open for Winston. Their eyes met for a milli-second as he entered the elevator.

“Floor, sir?” Toby asked.

“That’ll be five.”

He reached in, pressed the button for the fifth floor, and let the door go. As it closed, Winston watched him sweep the hair out of his eyes, turning to rejoin his colleague. Maybe it was time to make a move, Winston thought.

Toby was just returning from delivering extra pillows to one of the guests.

“I’m going to use the restroom. After I get back, you can check out for the evening,” Wells said. A much different tone than he was used to, Toby smiled to himself. Karla would have loudly announced, “Hold the fort! I’m gonna take a shit!”

Taking his suit coat off, first using an elegant horse hair clothes brush to wipe it down, he hung it up in the closet. Now, seated at the desk in his room, Winston picked up the phone and pressed the single button marked, “Concierge.”

“Incoming call, guest Winston Day, room 505,” the monitor in front of Toby announced. Picking up the phone, he started to say in his official grown up voice, “This is the concierge desk, Toby speaking. How can I help you, Mr. D…?” He gulped and almost choked. Day?? No way! How could it be?

In an instant, his mind raced back a few weeks. That name conjured up some major memories. First off, the taste and feel of Day Benjamin’s exquisite cock in his mouth. Cupping his smooth hairless balls. His smell. Then, the feeling of Day’s tongue deep inside his ass. Their mouths crushed together, tongues doing battle, early in the morning before he left Montauk after that amazing weekend.

“It’s a family name,” Day’s smiling words echoed in Toby’s mind. “Our family makes sure there’s a Day in every generation.”

Now this.

Quickly clearing his throat, “Ahem! …Mr. Day?”

“That’s Professor Day, if you will,” Winston snorted.

Toby’s face suddenly felt hot. Looking down at the monitor, he saw that he had missed “Prof” in the salutation field.

Partially recovered, in a somewhat smaller voice, “I’m so sorry, Professor Day. How can I help you?”

“Dinner tomorrow night, young man. A table for four at eight o’clock. What do you recommend?”

“What’s your preference, Professor Day?”

“Quiet. Elegant. Known for seafood and freshwater fish.”

Toby’s heart and mind raced. That narrowed it down to a bajillion places where he’d never eaten. Eyes and mouse scrolled at a rapid pace down the computer screen and across several menus.

“Let’s see…” Stalling for time. “May I suggest Cotton and Rye? Tasteful, luxuriously appointed. Famous for their Stuffed Carolina Trout.” Toby read the description word for word off of the display.

“Sounds about right. Would you book it for me, young man?”

“Certainly, Professor Day.” As he said the words, he silently groaned. Why? Why? Why? Why did he have to recommend the toughest table in town? “If you’ll allow me, I’ll call you back as soon as your reservation is secured,” Toby said, reciting one of the many phrases he’d committed to memory.

“Right-o.” Winston clicked off.

Eyes stinging, Toby pressed the speed dial button connecting him to the maitre’d at Cotton and Rye.

“Doesn’t look too good.” At least the guy answering the phone sounded somewhat sympathetic.

Toby’s breathing became labored. He desperately searched the display for anything he could use. There it was. “C-c-ould I speak to Calvin?” He squeaked.

“Oh–kay,” sounding a bit resigned. “Hold on.”

A long pause. Silently, Toby mouthed “Fuck. Fuckity Fuck. Fuck!”

Then, “This is Calvin.” Low resonant voice, very official sounding. “How may I help you?”

Toby could feel sweat forming on his upper lip. Mustering as much strength as he could, he pushed forward. In a clear sounding voice, “Toby here from the DeSoto. I wonder if you could help me with a valued guest.”

“Can I place you on a brief hold?” Calvin asked in a condescending tone that seemed to pass mostly through his nose. Less than 30 seconds later, “I think we can accommodate you. Table for four at eight o’clock. Confirmed!”

Toby was so excited he actually peed a little into his underwear.

Triumphant, he pushed the buttons for 505.


Toby tried to remain calm. “Table confirmed for eight at four o’clock, sir!”

“What was that?”

Horrified, “I mean. Table for four at eight o’clock.” Almost breathlessly, “Cotton and Rye is confirmed.”

“Why, thank you, young man.”

“Will there be anything else, sir?”

“Would you mind giving it to me in writing? I sometimes forget where I’m going.”

“Of course not, sir. I’ll leave the confirmation in your mailbox.”

“Actually, I’d prefer that you bring it to my room. Do you mind?”

“Of course not! Be right there!”

Toby was just completing the reservation confirmation when Wells returned. Using his neatest handwriting, he filled out the form, printed on heavy card stock.

“Hmmm,” Wells looked over Toby’s shoulder, one eyebrow raised.

“I’m taking this up,” Toby said confidently, as he left the desk.

“Ok. Then you’re done for the night,” Wells called after him.


Toby had no idea who or what to expect from this latest Day when the door to 505 was opened. An older man, quite distinguished looking, with his bushy white mustache, pearl grey vest, and elegant looking bow tie. Who did he remind him of? Maybe, it was that guy, a TV news anchor from way back. He remembered seeing him in an old video of the first astronauts landing on the moon.

“Come in, young man.”

“Sir?” Toby wasn’t sure what to do.

“I said, come in!” Winston said a bit sharply as he turned away from Toby and headed back to his seat at the desk. Taking the reservation confirmation from him, he glanced at it quickly, before dropping it on the desk. An elbow supporting his head, Winston turned to gaze at the boy. Up close, he was even more superb. Winston’s eyes dropped to the narrow gold name plate on his chest.

“Your name is Toby?”

“Yes, sir.”

“Short for Tobias?”

Toby smirked. “No. It’s just ‘Toby.'”

“And your last name?”

“Gallivan, sir.”

“Ah…Irish, I take it.”

“Ya. I guess so,” Toby shrugged.

“From the looks of you, Black Irish.”

Toby chuckled nervously, “That’s what my grandma calls me sometimes.” Pointing to his own head, “Black hair.”

“Yes. Quite charming,” Winston smiled. “How old are you, Toby?”

“18, sir.”


Toby blushed. Why was it “perfect,” he wondered? Perfect for what?

Winston’s eyes slowly roved over Toby’s body, starting from his head, winding down his slender body, encased in that ridiculously over-sized jacket, to his narrow hips, lingering for a moment on his crotch, before dropping to his ankles.

Toby had to concentrate hard to keep from twitching. This all felt so odd and, so… He couldn’t put his finger on what it was. He felt like he was being visually stripped naked. It was uncomfortable and…Toby could hardly believe it! Exciting! He actually felt his cock stiffen.

Winston held a closed hand out to Toby, “Here ya go, young man.”

Toby reached out with his own hand. Winston opened his, dropping a five dollar bill into Toby’s open hand.

“Sir. Not necessary.”

“That’s all right.” Sounding somewhat distant, “Thank you.” Winston turned his head, looking down at the confirmation.


Covers and top sheet pulled back. On his back. Naked. He stared blankly down at his pale featureless chest and stomach. The fingers on his left hand lightly tickled the underside of his very erect pink cock. The index finger and thumb on his right hand pinched the nipple on the left side of his chest. With each pinch, he ever so slightly thrust his hips up and flexed his cock.

Earlier, after the 30 minute drive back to his parent’s house on Tybee Island, he couldn’t wait to get to his laptop and find out more about Winston Day.

“Holy shit!” Toby muttered under his breath. Winston Leonard Day. The guy had his own Wikipedia page! Professor of History at the same select school it seemed everyone he knew either attended or planned to go to. What was it with that damn school?

A long list of accomplishments and awards. Several published books. Interesting: no immediate family listed. Instead, an extensive family tree. There was Day’s family, the Benjamin’s. Day’s mother was apparently the daughter of one of Winston Day’s cousins.

Toby HAD to talk to Day. But, just as he picked up his phone, he got an IM from Bell. Toby groaned. What shitty timing!

His fingers arranging the hair in front of his ear and then behind. Then, swirling them around the inside of Toby’s ear. He’d melted then and there. It had been more than a year since they’d originally met on Tybee. His first love. The boy he’d let take his cherry. Campbell Maine, the arrogant prick, beautiful, sexy thing that he was.

Click on a star to rate this post

Average rating 3.8 / 5. Vote count: 45

No votes so far! Be the first to rate this post.

4 thoughts on “Rich Uncle

  1. Rob says:

    Not the story, I intended to read. However, well written with many opportunities presented! PLEASE Continue and deliver the whole point of this Explanation!

Leave a Reply

Your email address will not be published. Required fields are marked *