Unforgettable Weeks - Cover

Unforgettable Weeks

Copyright© 2015 by Jay Cantrell

Chapter 23

Drama Sex Story: Chapter 23 - Two people from vastly different worlds shared one crazy night two months earlier. Regan Riley learned that life is sometimes serious and Andy Drayton learned that life can sometimes be fun. Now they've decided to see if they can overcome their differences and forge a relationship. This is the sequel to "Unending Night."

Caution: This Drama Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Consensual   Romantic   First   Oral Sex   Exhibitionism   Slow  

8 p.m. Saturday

Joy Dalrymple was chatting as amiably as she could with Robert Holmes, the Yale student her father had lined up as her date for the evening.

There were several other girls from C-B gathered around with their dates as they did their best imitations of their parents schmoozing at cocktail parties. The air was thick with Chanel perfume, Polo cologne and Axe Body Spray.

The room was filled with teenagers and young adults who attended exclusive prep school or universities and the young males in the room were swapping stories about their popularity on campus, their parents' beach house or the amount of money they had access to at that moment.

The young ladies were eating it up, for the most part. These were the boys they had known their entire lives and they understood how the game was played. If the girl's family needed something from the boy's, she would be expected to put up with his fumbling gropes and lecherous advances – but she was only to permit him past a certain point if he could deliver what her family wanted.

If the situation were reversed, the boy could plan on a night of snide comments and hostile glares from his date. If he played the role of whipping boy well enough, she might grace him with a kiss on the cheek as the public part of the evening concluded. If he didn't, he might be left standing in humiliation as she publicly dropped him and went home with someone else.

Ruth had pointed out the intricacies to Regan as they got their nails done at an upscale salon. Regan had been appalled. In this, Regan had been fortunate that her mother rarely needed assistance from anyone – but a voice inside of her told her that even if Rita and Robert faced dire ruin, they would not pimp her out to save themselves.

All chattering ceased when Regan and Ruth strolled in, arm-in-arm with their public school dates. The events at the Riley household and in front of the Renaissance Hotel had made the timing play out as it should. In the world of C-B Prep, the richest and most influential were the last to arrive – in order to make their entrance as grand as possible. Although Ruth was far down the list at C-B, Regan Riley (courtesy of her family) was at the top.

"Is my fly down?" Andy asked in a whisper as they stepped through the doorway. All eyes in the room had turned to face the couples when the doorman had announced the arrival of Miss Ruth DeLancy and Mr. Christopher Grant. All the C-B girls had stopped talking because they were aware of who would be coming next. A few of the boys continued to chat, only to be urged into silence by their dates.

Regan smiled wondrously, her white teeth a stark contrast to her black gown.

"Not yet but give me time," she whispered back. Once again, Regan had flaunted tradition by refusing to take Andy's elbow. She had latched onto his hand and didn't appear ready to relinquish it anytime soon.

"Miss Regan Riley and Mr. Andy Drayton," the doorman intoned. Regan had informed the man as politely as she could that if he called Andy "Andrew" she might well have him castrated on the spot.

Joy immediately broke from her date and hustled forward. She clasped Ruth in a tight hug before shifting her attention to Regan and Andy.

"You both look amazing!" she said, making no pretense that she wasn't looking both of the newcomers up and down like a side of beef at auction.

"You look very pretty, Joy," Andy said politely.

Joy's gown was off-white and hung from one shoulder. She wasn't as generously proportioned as Regan – and was well off the standard set by Ruth DeLancy – but the gown did highlight her best assets – a slim waist and an athletic butt.

"I love your gowns," Joy enthused. "Both of them are just perfect for you."

Joy's date sauntered over with a knowing smirk. The news that Rita Riley's daughter was dating – and had apparently settled on a public school student – had made the rounds from Clairborne Benedict Prep to several of the wealthiest families in the area. Robert Holmes' father and mother had made their fortune in real estate but the prices were getting higher and it was becoming tougher and tougher to add to their wealth. Robert thought plucking Rita Riley's daughter from the vine might be the perfect way to ensure his family was always wealthy – an assessment his parents shared.

"Hello again, Regan," Robert said in his best debonair voice.

"Have we met?" Regan asked, pointedly looking at the hand the man held in front of him.

"This is my escort, Robert Holmes," Joy said. Her face was neutral but her eyes danced with merriment.

"Oh, yes," Regan said blithely, still ignoring Robert's attempt to take her hand for a kiss. "I believe Joy mentioned that you were invited. It's a pleasure to make your acquaintance."

"We've known each other for years!" Robert protested in a loud voice. "Our families have done business together for decades."

"Hmm," Regan mused. "Well, apparently you didn't make much of an impression. I hope you enjoy your evening."

She directed Andy away from the stunned Robert Holmes, whose hand was still outstretched in front of him and his mouth agape.

"That was pretty harsh," Andy noted as he looked back over his shoulder.

"He's an asshole," Regan said through clenched teeth.

"Still... ," Andy said. "He is Joy's date."

Regan sighed heavily and directed him to a table filled with soft drinks and bottles of water. She knew Andy had a pretty firm stand on right and wrong and she worried that the explanation required would lead him to some erroneous thoughts about Regan.

Ruth and Chris followed in their wake, with Chris looking just as confused as Andy seemed to be.

"Let's find our table and I'll tell you about the Robert Holmeses of the world," Regan said. Andy was still glancing back periodically. Joy had steered Robert to the opposite side of the room but she saw Andy looking and gave him a megawatt smile.

Although the students at C-B had observed the societal norms taught by their parents, the administrators at the school had not. The headmistress had been peeved at Regan Riley for months – well before her ill-advised trip to the city nine weeks earlier. She had grudgingly acquiesced when the Rileys wanted to invite a public school student for a weekend visit. She had initially balked when Regan had submitted Andy's name as her guest for the Cotillion – but several senior administrators had pulled her aside and mentioned how much of C-B's bottom line was reliant upon contributions from the Rileys.

The woman thought she had gotten her revenge in the seating arrangements at the event. Regan, Ruth DeLancy and their public school guests had been relegated to the farthest reaches of the room. Little did she know that she had played directly in Regan's hands once again.


Andy held Regan's chair as she sat down and she offered him a grateful smile as he moved to sit beside her. Once everyone was seated around the table, Regan leaned forward so she wouldn't have to yell.

"Andy, I want to explain to you why Robert Holmes is here with Joy Dalrymple," Regan said. "But I don't want you to get angry until you hear me out. OK?"

"I don't really care why he's here with her," Andy noted. "I was more interested in why you were rude to him."

"She was putting him on notice that she arrived with you and she will leave with you," Ruth cut in.

Andy glanced at Chris to see if he could add clarity but his new friend only shrugged helplessly.

"If I explain the first part to you, you'll understand the second part," Regan assured him. "Robert Dalrymple – Joy's father – is a partner in a successful downtown law firm. You know that, right?"

Andy nodded.

"The Holmes family is heavily invested in real estate," Regan continued. "According to my mom, they are overextended. Now, although Robert earns high six figures a year, the Dalrymples are not considered wealthy."

"They are to me," Chris said. "My dad barely earns seven figures when you toss in the decimal point."

Andy nodded again.

"But in the world of top-end investors – the one-percenters – they are not," Regan said. "What the Holmes family needs is an infusion of cash to see them through the lean times. Robert has been their lawyer for several years. Robert's father pressured her father into having Joy invite him here tonight. His sole purpose is to find some poor, impressionable girl and charm his way into her life. I was his first target – for obvious reasons. First off, it's not really much of a secret that I was bringing you tonight. You have to understand, Andy, to the other guys in this room, you're a non-entity. I put the word on the girls. I told them that I would not put up with any crap from them or their dates tonight. Unfortunately, guys like Robert Holmes – and perhaps half a dozen others in the room – do not understand the consequences of pissing me off."

"So you're going to bury Joy?" Andy wondered. He glanced again to where Joy sat.

"Of course I'm not," Regan said. "But I will verbally castrate any guy who tries to put a move on me – and I might physically castrate the next one who tries to move on me while you're standing there."

"See, I didn't get that impression," Andy said.

"You missed it when he was sauntering up," Chris interrupted. "He was eyeing both of us up and down for a minute, then he smirked and sort of shook his head in dismissal. I thought he was just a dick, you know. I didn't realize he was trying to make a play. Now that it's been explained, yeah, I totally see it."

Ruth offered Chris a grateful glance and reached over and took his hand atop the table.

"Maybe I'm just dense," Andy said, again looking around the room. From his vantage point, he could see almost everyone else – and most of the people in the room were paying quite a bit of attention to the table nearest the wall. "I don't see how hooking up with you would help his family any. I mean, yeah, in a few years you'd be able to toss some cash his way to get him to go away but now..."

He shrugged and Regan broke into a smile.

"Not me," she said. "It's my parents he's after. He is looking to give his family an inside track to venture capital by cultivating a relationship with the daughter of a wealthy family. As I said, Joy's family really isn't wealthy enough to help him out."

"And my family isn't interested in real estate so he won't come sniffing after me," Ruth added, give Chris' hand a squeeze.

"Then he's not very bright," Chris replied with a wink. Ruth blushed prettily at the compliment.

"There are, perhaps, six or seven young women in here whose families have access to enough cash that it would be worth his while to try to gain an introduction to her parents," Regan said, getting the conversation back on track. "Women are still viewed as property by a lot of these pigs so they have no problem leveraging a daughter to get to the parents."

She stood and craned her neck.

"He's not the only leech here," Regan said, pointing toward other young men in the room. "Him, him, him and him. They're here for the sole purpose of furthering a business relationship for their families. I know for certain that all the girls who invited them were practically forced to do it by her parents."

Andy looked around and saw several red faces on the guys Regan had identified. He wondered if he was going to have to fight his way out of the dance before the night was through.

"I served notice on Robert Holmes – mostly because he really is an asshole," Regan said. "Mom warned me that I would run into at least a few guys tonight whose families had approached her with their hands out recently. I asked her how I should handle it and she told me to do as I thought best. Well, I did. I am here with you and I wouldn't rather be with anyone else. These guys can put on all their fake charm. They are not getting into my panties – now or ever!"

Andy nodded and leaned toward Regan.

"Would this be the wrong time to mention that you're not wearing any panties?" he whispered.


Andy felt the tap on his shoulder and turned his head to see who was bothering him. He and Regan had been dancing for only a few minutes but she felt wonderful in his arms.

"May I cut in?" a young man asked.

"Fuck off, Jerk," Regan said.

"I guess not," Andy said. He turned back to Regan, who immediately resumed her previous spot with her head against his chest. Once again, the tapping came, this time rather more insistent.

The same guy was standing there glaring at him.

"I said, 'Fuck off!'" Regan said, this time loud enough to be heard by everyone nearby.

"I simply want a dance with you," the young man said.

"And I simply want you to ... Fuck Off!" Regan said.

"Look, Pal," Andy said in a calm voice. "The lady doesn't want to dance with you. I think that should be obvious – even to you. Now, you can walk away with only your pride hurt. If you stay, I'm going to hurt a lot more than that. We're going to continue our dance. If you continue to bother us or if I see you near us again tonight, well, I'm going to see how many holes I can put in the wall with your head before it bursts like a melon. Do I need to be clearer?"

"This is why we don't allow people like you into places like this," the man sneered.

Andy nodded.

"Probably," he agreed. "It certainly makes it a lot safer for guys like you to be a douche bag if guys like me aren't around. The rest of your butt buddies are probably used to you behaving like a fool so they just let it go. Me? No so much."

Andy's last retort brought laughter not only from Regan and Ruth but from several onlookers. The young man's face get red and Andy was positive the guy was about to take a swing at him. He decided he would take the first punch and then drop the idiot like a hot rock.

"Don't even consider it," Regan said, pushing past Andy to stand in front of the guy. "He's not kidding. He will kick the ever-loving shit out of you and I will fight anyone who tries to break it up. It's time to decide if you want to walk away or be carried away."

"What's the problem here?" a female voice asked. It was clipped and nasally so Andy figured it was one of the chaperones. He figured he was about to be shown the door.

"Regan didn't want to dance with Bill Winston and he was a jerk about it," Joy Dalrymple said immediately. "Andy stood up for her."

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