Rich Uncle Pennybags

Bell had just sent him another disappearing photo on WhatsApp. Visible for just a minute, meant only for his eyes. It followed a familiar theme. A smart ass expression on his face. His smooth bare chest, obviously naked. Hips showing with just the tip of his stiff cock visible at the very bottom of the frame. Worse yet, apparently in the arms of another guy. A person who looked depressingly like Armie Hammer.

"Whuzz up?"

As usual, keeping Bell engaged for more than a couple of exchanges was impossible. Maybe it was because Toby always whined about missing him and needing to see him. This time, no different. From now on, Toby resolved, he was going to play it cool.

Cool was the opposite of what he felt, though. Before he reached out to Day, he needed to clear his head. Now, laying on his bed, the tickling became stroking, the pinching harder. He looked down at his narrow undulating hips. A couple of minutes later, Toby shot a rope of cum that hit the under side of his jaw.

Following a thirty second shower, Toby was back on his bed, naked on his tummy, up on his elbows. He two-thumbed an IM to Day.

"Hey."

Surprised, he got an almost immediate response.

"You sexy thang!"

The guy who'd popped the question to him just a few weeks ago on Montauk.

"Are you?" He'd asked, meaning, are you gay?

Eric Day Benjamin, 18 years old, just like Toby. Incredibly good looking. Short medium brown hair, thick eyebrows, light green eyes, a long narrow nose, square jaw. Always wearing very smart looking glasses with dark frames. 5'10" slender and muscular. Think, that actor from "Baby Driver."

The answer to that question? TBD.

"I just met another Day."

"NS!"

"Yup."

"Do I know him?"

"Dunno. Winston Leonard Day." Toby typed his whole name in for a little more impact.

A pause. The phone rang. It was Day.

Laughing in a somewhat high pitched voice, "Well, darlin'!"

Toby chuckled.

"Ya. Dear cousin Winnie."

"So, I was right! You ARE related!"

"I told ya before, Tobes. Days and Knights." In addition to lots of Days, there was also an arm of the family that used the name, Knight. It was a running family joke. "So, how did you ever meet dear cousin Winnie?"

Toby recounted his story. Then they went on to catch up. Just like Toby, Day was excited about his first year of college. And...he'd met someone. Toby's breath caught in his throat. But, really, he had no cause to be jealous. That weekend had really been just a hook up. An amazing, wonderful hook-up. No promises, no commitments had been made.

"Who's the lucky guy?" Toby asked.

"I met him at a football game a couple of weeks ago." A pause. "His name is Carey."

Something went "ding" inside Toby's brain. Couldn't be. He shook the thought away. "So, how is it?"

"Well, 'it' isn't anything. Yet." Day chuckled softly.

Toby smirked, "Well, let me know when you're ready to spill the tea." Before Day could respond, "What do I need to know about your dear cousin Winnie?"

"Notta lotta." Day continued, "Kind of a pompous ass, but that isn't anything special for my family." He chuckled. "Big shit prof on campus. Always treated me nice. Never married."

"Do you think he's gay?"

Day laughed, "I dunno. Nobody's ever caught him wearing a dress and heels." A pause. "Why?"

"I dunno. Just a vibe."

Day chuckled, "You're way too inexperienced to have developed gaydar, punk!"

Toby shrugged. Maybe so.

***

Dinner on Tuesday at Cotton and Rye was as expected. Well, perhaps a bit better than expected. Even though there was a healthy crowd around the restaurant entrance, his party was whisked to their table instantly. Food was excellent, service impeccable, and the company of old friends enjoyable.

Participation in two panel discussions yesterday was boring but he always enjoyed the lavish praise heaped upon him. The room was packed for his keynote today. He did a magnificent job, if he could say so himself. The applause was loud and long.

He was obliged to attend tonight's closing banquet. Winston begged off early, though. He had something else on his mind. The boy.

Disappointed not to see him on Tuesday, his hopes were lifted when he walked by the concierge desk today on his way to the banquet. Yellow marker in hand, he was tracing a route on a map for another guest. In between strokes of the marker, he brushed the dark hair out of his eyes.

Just before quitting time, Mr. Thinkwell breezed by.

"Good evening, Mr. Do Tell!" It slipped out just like that. Well, fuck! Color drained from Toby's face and it got hot at the same time.

"What was that??" Thinkwell asked sharply as he stopped and turned back.

Wiping his hand across his mouth, his eyes suddenly searching for something on his computer screen. "Sorry!" He mumbled, "I meant Mr. Thinkwell."

Thinkwell just harrumphed and walked away.

A few minutes later, Toby finished with his last guest. He had just changed out of his work clothes into a loose fitting t-shirt, cargo shorts, and sandals when he heard his name being called over the p.a. system used for communications in the back end of the hotel.

Wells was finishing a phone call as Toby returned to the concierge desk.

"505," he said.

"But, I thought I was done." Toby protested.

"Well, you've been summoned. Get up there."

"But, I've already changed," he protested.

"Just do it!" Wells commanded.

Winston's eyes quickly roved over Toby's body. Exquisite! He could actually see the boy's shape now that it was no longer masked by that ridiculous jacket.

"Thank you again for making that reservation."

"I hope everything was to your satisfaction."

"Quite."

Toby felt a rush of relief and satisfaction run through his veins as he stood before the Professor. He'd made it a point to call the restaurant yesterday afternoon.

"Just calling to confirm the reservation for our valued guest, Professor Day," He'd said, emphasis on "valued."

There was a long, almost pregnant pause. Winston gazed over the boy's entire body. He really was as slender as he'd imagined. That pure white skin on his neck and bare arms promised more delights underneath.

The next part was the green light-red light moment. It was a line he'd used many times over. No beating around the bush, no cheeky remarks or awkward chatter.

"Say, would you mind removing your shirt?"

Toby gulped. His stomach turned over. What is happening??? He looked at the Professor, a small wrinkle of worry between his eyes. His mouth dropped open but nothing came out.

Winston looked for a response. It was either going to be, "No way, fucker! I'm outta here!" or...

Toby's breath came in short spurts. He looked at the Professor as he realized instantly that his dick was tightening up. He could barely feel the fabric but somehow he was able to pull the bottom of his t-shirt up a little over his waist. Almost robotically, he reached under with one hand, grabbed the other arm, pulling it through the sleeve. Likewise, the other arm. Grabbing the t-shirt's neckline, he pulled it over his head.

After it was off, he just held it in his hand. Maybe, this would be it. A nice tip and he'd be on his way.

"I'll take that." Winston grabbed the t-shirt from Toby, barely able to conceal a smile.

Boney shoulders, hairless chest, very little definition, small pink nipples, a flat stomach, innie belly button. The boy checked several boxes on Winston's list.

"Turn around, if you would."

Toby did as he was told, shuffling around until his back was to Winston. Brushing the hair out of his eyes, he twisted around to see what he was looking at. No surprise, Winston's eyes were glued on Toby's butt. The fabric of his shorts was ever so slightly taut against the roundest parts of each one of Toby's butt cheeks. His back, nice and smooth, a few moles here and there, the cleft between his kidneys and the curve of his hips making him look all the more attractive.

Winston's approach had been perfected with a lot of practice. Requesting, persuading, suggesting. Never demanding. It was important not to appear threatening. The boy had to be willing, not feeling forced.

Embarrassed, humiliated, disgusted. The instinct to flee was in the forefront of his mind. Back further, Toby felt a growing sense of excitement, the attraction of shame, the desire to just give in. Looking over his shoulder at the way Professor Day stared at him was a huge turn-on.

After he asked the boy to turn back to face him, Winston was pleased to see the front of his shorts well tented out. Within a couple of minutes, the rest of Toby's clothes were off. In a soft, but firm voice, Winston directed him to the bedroom where he asked him to lay flat on his back.

"Raise your hands over your head," he directed in a firm voice. Pulling out a set of handcuffs attached via a rubber cable to the headboard, Winston closed them around one of Toby's wrists. "No worry," he purred. "These are meant to lightly restrain. If you feel the need, they will release with a quick jerk." Moving to the other side, he closed another set of handcuffs around the other wrist.

As Toby turned his head to watch, Winston moved to the foot of the bed, pulling a length of rope out from under the bedspread.

"There ya go," He half whispered as he grabbed Toby's ankle and pushed his knee up. He expertly and methodically tied Toby's thigh to his ankle. "Is that ok?" he asked.

"Uh-huh," Toby nodded, watching his every move.

On to the other ankle, he performed the same task. 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.

Winston was gratified to see the boy had shaved his pubes so he was nice and smooth making his cock look all the more delectable. On second thought, he shrugged, a crown of black hair covering his pubic area might have been just as nice.

"Lift your hips up a bit for me," Winston requested as he slipped a pillow under Toby's ass. He looked down at his puckered brown hole with admiration. "Will this be ok?"

"Ya." Pause. "I don't mind." Toby stared at the ceiling.

Very good! Winston smiled to himself. This giving in, not caring so much, was important. It added a heightened level of excitement to the whole thing.

Out of nowhere, Winston produced a silicon glove, the index and middle finger of which he quickly coated with lube. After circling Toby's light brown anal verge with his index finger, Winston held it briefly at the entrance before steadily inserting it inside his ass. Toby's mouth opened in a long silent sigh.

Toby tried hard to relax even though the pressure naturally made him want to push Winston's finger out. The second finger was easier. Once the dildo appeared and was introduced to his butt hole, he was more than ready.

Winston was amazed at how well the boy performed for him. He maintained an erection throughout, even when he turned on the dildo's vibrating feature. Sensing it was going to happen, he let go of the dildo and wrapped his fingers around Toby's cock. In short order, Winston was gratified to see a generous explosion of cum erupt out of Toby's cock.

After it was over, Winston used a warm damp washcloth to clean up the mess on Toby's stomach. He lightly bathed his cock and balls. When he washed over his ass and butthole, Toby opened his mouth again and softly groaned.

Loosening the ropes and letting them fall away from Toby's ankles and thighs, Winston partially cradled his head in his arms. Toby's legs relaxed, his legs remaining mostly open to allow his crotch to dry. His prick had now returned to its relaxed state, a more normal three inches.

"Would you like me to remove the cuffs?"

"Hmmm. Not just yet." Toby loved the feeling of his arms restrained over his head.

The boy's breathing became shallow and steady. Winston smiled. He was obviously dozing. Could this have gone any better?

Winston thought ahead. He couldn't wait to let Oliver know about the boy. Oliver, his partner in crime, so to speak. Miranda, too. She would positively lap him up. That evil grin of hers. Winston had to suppress a chuckle. He'd find a way, he'd have to, to get the boy up to campus for a visit. He visualized the scene.

It was going to be prodigious.

The End