He looked young. Very young – Younger than she had ever encountered in two years of searching. His face was childlike in a way she instantly craved, with small dimples on his cheeks and oversized teeth that would present themselves proudly with a wide smile. She took in a short breath at the site of him seated across the restaurant, trying to contain the urge she instantly felt, the flutter that crept through her stomach and into her chest, which seemed to bulge out at the very site of him. He had not seen her enter, and she took the final moment of privacy to take another deep breath and calm herself before approaching. She knew before they went any further, she would have to see identification. He almost looked too young.

He watched her approaching from across the room in a tight black skirt and white blouse that extenuated her features in a way that made him immediately feel as though she was out of his league. She was older, though maintained remarkable beauty for her age. She walked with a confidence that still made heads turn, even as she was pushing 50 years old.

“Jamie?”

She nearly startled the young man, despite approaching the table cautiously to match him with the picture she had memorized from their emails.

“Yes,” he confirmed nervously.

“I’m Karen.”

She extended her hand, and he quickly rose to his feet to accept the gesture, though he kept his eyes glued to the floor.

“Honey,” she titled her head lower to catch his eye sight, “look up at me, okay?”

He immediately followed instructions, snapping his up head and maintaining an anxious gaze.

“Yeah, sorry,” he said.

“It’s okay. I’m Karen.”

“I’m Jamie.”

They shook hands and took their seats in opposite sides of the booth. She remained calm and collected, placing her purse to her side and catching the waiter’s eye as he approached the table.

“Hi folks, how are you tonigh-”

“I think we just want drinks and some privacy this evening,” she said, cutting the waiter off.

“Okay, yes ma’am. What can I get you?”

“Gin and tonic.”

She locked eyes with Jamie and waited for his order. He privately felt as though he was being studied by his drink order, and he was.

“Sprite?” he ordered in the form of a question.

“You got it,” said the waiter, quickly abandoning the table in an attempt to save his tip. Karen smiled over at Jamie, feeling another flutter at the notion that he ordered a child’s, though still trying to mask her desires.

“Please don’t be offended, but before we go any further, I need to see your ID again.”

“I emailed it,” he said, protesting lightly but not wanting to make a fuss.

“I understand, but I’ve been faked out before, and you look very young. Do you mind if I see it again?”

Jamie obliged, reaching into his pocket and pulling out his wallet. He removed his driver’s license and slid it along the table toward Karen. She accepted the card, bringing it off the table just as the waiter returned with the drinks so as not to arouse any suspicious.

“Here you go. Just let me know when you’re ready for the check.”

She waited until he was a safe distance away before glancing at the driver’s license. It was legitimate, his goofy grin only bringing more attention to how young he looked.

“Twenty-three years old?”

“Yeah.”

“Are you aware of how young you look?”

“Yeah, people tell me that a lot.”

“Not a day over sixteen I would guess.”

Jamie quietly nodded his head in approval, unsure of how to respond to the line of questioning. Karen slid the driver’s license back to him, and he quickly moved it back into his wallet while she patiently stirred her drink and grinned across the table.

“I need you to understand, this is not about sex,” she said.

“Um, okay.”

“This about an agreement; a mutually agreed upon roleplay that each of us will partake in willingly. If you don’t want to be a part of that, or if you’re just in this to indulge some MILF fantasy, then it won’t work.”

“Okay,” he continued to nod in approval, sipping his Sprite from a straw, remaining just as nervous.

“Are you attracted to me?”

He gulped his drink, fearing any answer could be the wrong one.

“Um…”

“I’m not playing games Jamie. I don’t want you searching for the right answer when I ask you a question. Are you attracted to me? Answer.”

“Yes,” he quickly blurted out.

“Good, that’s okay,” she reassured him. “You have to be for this to work. You told me you like older women. Do I look like the type of woman you were referring to?” She leaned back and extended her arms slightly, revealing her whole outfit and the cleavage-baring blouse she had saved just for the occasion.

“Yes,” he said, his own heartbeat beginning to race.

“Good. Now why did you pick me?”

“I, um, I’m sor-”

“There are plenty of pretty girls on the internet. Why did you respond to my ad?”

Jamie took in a long sigh and prepared to come clean.

“I…”

“What did I say about hesitatin-“

“I need a place to live, and I don’t have any money.”

“Oh,” the admission took Karen aback, as this was the first she had encountered such a situation.

“Where do you live now?”

“An apartment with a friend and his girlfriend, but they’re kicking me out.”

“I’m sorry to hear that.”

Karen let an awkward moment pass by sipping on her drink. For the first time in the conversation, Jamie filled the silence.

“I’ll do what you want, I want to. But I also need a place to live, and you said I would get a room and free rent.”

Jamie looked around the mostly empty restaurant, occasionally scanning the room to ensure no one he knew was there.

“Why are you so nervous?”

“I’ve just, never met someone like this before, off the internet.”

“Were you afraid I was fake?”

“A little.”

Karen smiled at the boy and quietly admired his fear of the uncertainty. He appeared so unprepared for the world, like someone who needed more nurturement than they had received. She was prepared to take care of him.

“Jamie,” her voiced cut through the air in an authoritative tone, “Please look at me when I’m talking to you.”

Jamie held his head up, now embarrassed by the situation and the position he had placed himself in, and certain that she was about to dismiss him.

“Do you have family who will wonder where you are or want to see where you live?”

“No, not here. My parents live in Chicago.”

She tensed at the thought of his parents.

“Don’t say another word about your parents from now on, understand?

He nodded in approval.

“Please say you understand.”

“I understand.”

“It’s nothing against them, but for this to work I can’t have them in my thoughts. We have to be completely immersed in our roles, and that can’t include them. You can’t talk about your family.”

“Ok, I understand.”

Karen leaned in closer, just enough for Jamie to take a peak down her blouse as she glanced around the restaurant. She pulled her head back and caught his wandering eye. With a subtle motion, she placed her hand on his chin and lifted his eyes back to her.

“Not yet little boy,” she whispered seductively, cause his face to turn red and instigating movement on his thigh.

“Do you remember the list I provided you?”

“Yes.”

“And you are okay with everything on that list?”

“Yes, I think so.”

“You can’t hesitate Jamie. There are things on that list that can actually cause you certain physical pains. Do you need to see the list ag-“

“No,” he corrected himself, “No, I’m comfortable with the list.”

She stared at him, trying to feel out how genuine the statement was.

“You need to understand that this is an agreement based entirely on an honor code. I’m not making you sign a contract or a lease. It has to feel as real as possible for it to work.”

He cracked a small smile, realizing for the first time he might have been chosen, though her whisper turned stern.

“I also need you to understand that our arrangement is between you and me, and you and me only. If I read about it on the internet, you will be out on the street in a minute, got it?”

“Yes.”

She leaned back against the booth, taking another quick sip of her drink and crossing her legs, each one gently passing across Jamie’s feet.

“I’ll send my address in an email tomorrow, and you’ll bring your things over.”

“Okay,” he said, trying to mask the mixed emotions of nervousness and excitement.

“I’ll pay for the drinks. You go now.”

Jamie rose from the table and started his stride toward the door, only to be halted by a firm hand on his forearm. It was the first time they had touched, and Jamie let out a small gasp at the kinetic energy dancing on the ends of his arm hairs. He slowly moved his gaze down as Karen brushed a hand against her cleavage, pulling back the flap of her shirt ever so slightly to reveal the soft skin of her upper breast. Jamie could not help but look, and made no attempt to hide it.

“You’ll kiss your mommy before you go young man.”

She tugged his arm down toward, bringing his upper body with it. With a slight lean upward, she wrapped her fingers through his hair and awkwardly pulled her lips against his, holding the kiss longer than he expected. His hormones raged, as the slight movement on his thigh protruded to a shaming length off his pant leg. She released the kiss and he stood erect, making a quick attempt to adjust the urges of his body. Karen looked down at the pant leg as he avoided eye contact.

“The next time you see me, you call me mommy.”

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