Chapter 12

“Tom, is it?” Justin asked politely as he walked up to the man sitting alone in one of the diner’s booths. It was called the red-line diner and every one of these booths were upholstered in a bright red as was much of the other décor. It was definitely the right place, and the man had the right look as well as the promised set of eyeglasses laying on the table.

“Yes,” the fiftyish something man replied with a smile as he extended his hand. “I take it you’re the chaperone?”

“Yeah, her brother,” Justin replied nervously as he slid into the booth across from the guy. “I’ll text her to come in, if that’s ok.”

“Sure ... delighted,” Tom replied.

Justin quickly sent a text, and they made small talk as they waited for Nina, who Justin worried now might not show up. Tom explained his use of the alias Sam-11, with Justin then clarifying why a brother would come along on a first date. Both seemed in agreement that being extra cautious was best in these circumstances.

“Oh, here she is!” Justin exclaimed as Nina walked up beside him, looking more than a little frightened. He’d had her wear a short sleeveless dress, that showed off her legs as well as her thin neck and arms, making it abundantly clear she was a hot little teenager.

“Please to meet you, Monique,” Tom said as he stood and shook her limp hand gently.

“Not her real name...” Justin admitted with a smirk, “ ... but you understand?”

“I do,” Tom was quick to reply, “And she looks younger than I expected. Eighteen are you, Monique?” he asked Nina directly.

“Yeah, umm ... just barely,” she replied with a nervous giggle.

“You’re her first date,” Justin explained as he slid out of the booth, so his sister could slide in. “I’ll go for a walk now ... text me when you’re done,” he said to the both of them, getting a pleading look from his sister, “ ... I’ll come back ... or get lost ... whatever Nina ... I mean, Monique wants!”

“Fine by me,” Tom said as he looked to Nina for agreement.

Justin could see he wasn’t going to get her ok, so quickly nodded to his startled sister before quickly walking away. By the time he passed the window they were sitting at, on his way down the street, he found her sitting stiff-like, clearly out of her element. But she was talking to the guy at least, he assured himself with a second glance.

“Don’t go far,” she texted him a moment later, which got a chuckle out of him.

“Nothing’s going to happen in a diner,” he texted back. “Unless he sticks his toe between your knees!” he added jokingly.

“!!!” she texted back.

“Stop that! He can see your texting me!”

The texting stopped at this point, making him suspect they were at least being civil to each other now. Tom seemed honest enough so far as he hadn’t appeared to have been lying about anything. Whether he was as wealthy as he let on was another question, Justin warned himself as he walked. Rich or not, the guy looked able to afford a nice piece of jewelry or something like that, which he had promised his sister would be the very least she would get out of dating Sam-11.

“He doesn’t believe I’m eighteen!” she appeared to text in a panic after about ten minutes had passed.

“Assure him you are,” Justin texted back. He really wasn’t worried the guy thought this as his sister was pretty hot, and after a time the guy would likely just stop asking. Pussy of her quality could do that to a guy.

“He wants to take me shopping down the street!”

“Told you he would!” Justin texted back with a grin. “I’m around if you need me. Take care!”

“Ok.”

Justin then watched from afar as Tom walked out of the diner, holding the door for his sister, and then appeared to be walking with a daughter as they headed across the street to the small walking mall there. The guy was thinking ahead, Justin assured himself as he crossed the street as well, making sure to keep his distance.

The first shop Tom took his sister into was one for designer handbags, making Justin wonder just exactly how much Tom was willing to spend on a first date. The answer came when Nina walked out carrying an oversized expensive looking shopping bag, looking rather well stuffed with something even more expensive.

“He made me pick out something!” she texted him.

“Made you?” Justin texted back with a doubting emoji attached. “Sure!”

“Do I owe him something?” she texted next.

“No! If you give him something now, he’ll think less of you.”

“Really?”

“Yes! Let him kiss you on the cheek, then maybe on the lips. Be sure to smile afterwards!” Justin quickly texted then looked around to see if he could spot them again.

“I did,” came a text a few minutes later.

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“This thing was four-hundred dollars?” Justin asked in disbelief as he held up the tiny handbag, twirling it around by the handle as he sat in front of his computer.

“Yes, be careful with it!” she whined before grabbing it back, then looking expectantly at an incoming message on her cellphone

“Did you give him your number?” he asked incredulously.

“He was so nice,” she said softly as she stared at her phone.

“Don’t do that next time!” he growled.

“Ok,” she said absently as she texted someone. He quickly snatched her cellphone out of her hand and read the message. It was from Sam-11, and read, “I had a really great time. Hope you don’t think I need more from you because I don’t.”

“You don’t want?” he texted with a smirk as he avoided his sister’s attempt to get her cellphone back.

“I admit I do, but it’s not necessary I assure you. You’re so pretty!”

“Thank you. The handbag is really nice! I want you to ask me how far we should go,” Justin managed to text.

“We can go far, but I think you might be too young.”

“I’m not,” Justin texted back. “I’ve been with boys, but just one. Don’t worry about me!”

“I do worry about you, but in a good way. I promise!” Tom texted.

“Can I bring my brother again, if we meet somewhere private?” Justin texted as he watched his sister fume out of the corner of his eye.

“I don’t mind, but he may see something!” Tom replied with a winking emoji.

“He’s seen me making out,” Justin texted back, followed by an embarrassed emoji.

“Then I’ll plan on that!”

“Ha-ha!” Justin texted before adding, “He’s also seen me naked.”

“I’m jealous!”

“Maybe you soon won’t be.”

There was a long pause before Tom texted, “I’ll get you something very nice.”

“Fuck!” Justin said to his sister as he handed the phone back to her, triumphantly.

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“You’re not working today?” Justin asked his mom as they sat eating breakfast alone.

“No, no more Saturdays, your dad insisted,” she replied.

“Nice! Bet he’s happy,” Justin told her with a smirk, getting a cute smile in return. “Anyways, a guy’s coming by to drop something off for Nina.”

“Nina?” her mother asked with interest.

“Yeah, kind of for Nina. He met her the other day, and I invited him to drop something by.”

“Oh, he’s not too old for her?” she asked with concern.

“Way too old—like fifty something,” Justin replied calmly, watching as his mother shook her head in consternation. “Here he is!” Justin announced as he looked at the new message coming up on his phone. “You’ll like him!”

“Why?” his mother asked in confusion, just as they heard a knock at the front door.

“Come in!” Justin called out as he waved at Tom, alias sugar-daddy Sam-11, through the screen door, watching then as Tom cautiously let himself in, carrying a big envelope in one hand.

“This is my mom,” Justin told the guy as he accepted the envelope. “Mom this is Tom, the guy I was telling you about.” As he said this, Justin opened the envelope and began reading the STD report on the guy. All the right boxes looked checked, though he had to admit to himself that he’d never seen such a report before. Feeling assured now that the guy had no diseases, he handed the envelope back, getting a deep nod of thanks from Tom.

“Hey, mom—give me your phone!” Justin said as he reached out to pick it up off the kitchen table where it sat in front of her. He quickly sent a text to his dad, who he knew was out golfing today, then handed it back to her. The text had read, “There’s a man here, I think I want to fuck him!”

She looked startled by what she was reading, giving him the chance to snatch back the phone to see his dad’s reply. It read, “Do it whore! Use a condom!”

“You don’t need one, he’s clean,” Justin whispered to her as he gestured toward the envelope Tom was holding now. “I’m going bareback, he says he clean!” Justin texted next before showing her the reply he got.

“Do it!” was his dad’s response.

“Cool...” Justin grinned before turning to yell up the stairs, “Hey Nina! Get down here! Tom’s waiting!” He heard a distant reply, so began making small talk with Tom as his mother squirmed in her chair. “That’s how big Nina’s will get,” Justin declared after a time, pointing to his mom’s large cleavage.

“Justin!” she whined, “Now apologize—he’ll think you weren’t raised properly.”

“Ohhh?” Justin replied mockingly as he used her phone to text his dad again. “Should I show him something, he’s clueless.”

“Left tit, full on! Make it look like an accident,” came his father’s reply. Justin grinned impishly as he showed his mother the text. She wouldn’t do it, he told himself.

There was a long silence in the kitchen, with his mom looking down at the floor oddly, with face starting to redden. Then slowly she turned away and adjusted her blouse slightly before turning back and moving to squat down in front of Justin. “You’re a terrible dresser,” his mother told him as she moved to adjust his sock and pant cuff, though he didn’t think it was needed. That was when her tit plopped out into view.

“I remember sucking that,” Justin quipped, causing his mother to shake her head at him as she put her boob away. Looking at Tom, he could see the guy was now very interested in his mother. “Oh, here she is!” Justin suddenly declared as Nina walked in.

“Hi,” Nina said with a glowing smile as she presented a cheek toward Tom, who then quickly kissed it. She had the expensive handbag Tom had bought her, strung over her shoulder, and looked confused now by the fact her mother was looking all nervous like. Wearing a tight dress, mid-thigh in length, and with a pushup bra on, she was actually able to display some cleavage, though she had very little to show.

“I’ll walk her out to the car,” Justin suggested as he texted his father again. “I’m sure my mom wants to make sure you’re a gentleman before she turns my sister loose.” He had just texted, “Should I let him feel me up?” and was now reading a reply of, “Yes, as much as he wants, bitch!”

Handing back her phone so she could read the texts, he then took Nina by the arm, leading her out the front door and onto the porch. After closing the screen door, he carefully peered back through it, listening now as best he could.

“I’m sure you’re a gentleman, Tom ... someone I wouldn’t mind dating myself,” his mother was saying.

“Your too kind ... and very generous to let those two accompany me. I’ll watch them closely!” Tom replied.

“Uumm ... yes closely,” she replied while peeling aside a corner of her blouse, letting her left tit plop out again. “I’m so sorry ... I have to do this ... my husband and I—we have an open marriage. He ... he wants to hear about it.”

“No apology necessary, and I must say, the ladies in this family are unbelievably beautiful,” Tom replied as he got another eye full of tit.

“Thank you,” she said shyly before going all quiet on him. Tom then excused himself, but before he could turn fully away, she grabbed his wrist and pulled his hand to her tit, looking truly guilty for doing so.

“Fuck!” Justin whispered under his breath. His father had taken his mother further than he had even dreamed.

“Anywhere!” she said haughtily as she leaned over the table while exposing her other tit.

“Anywhere indeed,” Tom replied softly as he slowly pulled down her yoga pants, then began caressing her ample ass, while shooting concerned looks toward the front door. Tom made eye contact with Justin, who nodded his encouragement, which got Tom to then place a hand between her thighs. “I’d fuck you!” he declared as he pushed her further down on the table, now starting to finger-fuck her slowly. “But your daughter awaits. I’ll have to take a raincheck.”

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“I got to get me a car like that,” Justin told his sister as he walked her through the revolving door that led into the hotel lobby. Tom’s car was a Mercedes, and it was fully loaded with every bell and whistle Justin could think of. At the moment, Tom was a step behind them, having to deal with the valet that was about to drive off in his car.

“Oh my god!” Nina exclaimed as they walked into what could only be described as a small galleria, with the lobby of the hotel being situated off in the distance. About them now were various high-end boutique stores, which immediately drew Nina in. Window shopping now, as she held on to her brother’s arm, she seemed almost oblivious to the fast approaching Tom.

“Why don’t you pick out something?” Justin teased in a whisper.

“Noo,” she said with a shake of her head before turning to look at the fancy lobby ahead of them. “I wonder what the rooms are like?”