“Nope.” Emmy shakes her head. She notices the lounge-like area on one side and his bedroom area on the other, with nice furniture and decorum sprinkled throughout. She puts her purse onto a chair. “Nice room.” She smiles slightly, feeling a bit anxious still.
“I know you’re new to this, but you can relax. I won’t bite.” He says in a lighthearted and reassuring tone, smiling across the room at her.
“Well I’m not so sure about that going by your email.” Emmy playfully retorts.
He laughs as he approaches her. “I’m Jack, by the way.” He extends his hand.
“Hayley, obviously.” Emmy replies, looking down a bit as she shakes his hand. “Sorry that I’m a bit nervous.” She says bashfully.
“Oh, don’t worry about it.” Jack says casually. “Here, let me show you the view.” He says as he steps to her side and places his right hand on her lower back, beginning to guide her toward the window side of his room.
“It’s great.” Emmy says as she smiles, looking out.
“Yeah, usually most rooms in the city here have terrible views but I was fortunate enough to get this one. You can see Abbotsford park over there. And the sea port over there.” He points out, his hand rising up a bit on Emmy’s back. “Sun’s going down soon so we’ll probably get to see the sunset.” He holds her a bit closer, his hand going to her hip and pulling her in. “So, care for a drink before we begin? I just got this really nice Merlot.” He asks as he looks down to her.
“Sure.” Emmy smiles back. She kind of likes his smooth, confident voice. He guides her toward the lounge area of his room, toward a table with a bottle of wine and two glasses on it. Emmy sits in a standard feminine position, with her legs crossed.
“So… How was school today?” Jack asks with a smirk as he pours a glass.
Emmy giggles a bit, blushing. “It was… Fine.” She nods up to him, smiling.
“You mentioned something about getting ready after school to come here is all…” Jack hands her a glass of wine. He sits down with his own glass.
“Yep, I’m still in school.” Emmy nods awkwardly.
“Can’t finish quick enough, huh?” Jack asks before taking a swig of his wine.
“Yeah.” Emmy forces a slight laugh. She notices how he drinks and tries to emulate. She swirls the glass slowly, smells, then drinks a little bit. Jack watches, smiling, thinking she probably doesn’t come from the same background he does and lives a different lifestyle.
“Do you like it?” He asks.
“Yeah, it’s great.” Emmy smiles.
“Probably shouldn’t be giving a minor alcohol but I think that’s the least of my worries here.” Jack chuckles slightly as he smiles at her. “I mean, you’re still in high school. I’m such a dirty old man.” He says in a self-deprecating tone as he shakes his head and takes another drink.
“I don’t mind.” Emmy says quietly in an aroused tone, shooting him a flirtatious smile. She drinks more.
“Yeah?” Jack’s voice gets deeper. “You like dirty old men?” He asks playfully, his hand covering hers on the table and using his thumb to slowly caress her smooth skin.
“I’ve been with a few…” Emmy replies softly.
“You’re so sexy, Hayley.” Jack says. Emmy looks down, blushing a bit and smiling. “You look incredible. Even better than your pictures.” He continues confidently. “How about me? Am I better or worse than what your were expecting?” He asks playfully, taking his hand away and drinking more.
“Definitely better.” Emmy smiles, nodding slightly. Jack does look better than what she thought he might look like. He’s around fifty, approximately six feet tall, of regular stature, has a slight tan, and short hair that’s mostly grey. For a man of his age he looks good. He’s dressed in a light blue dress shirt with the top buttons undone, tucked into black khaki pants.
“Well that’s good. I’m glad to here it. I may not be like the hot young guys at your school but I’m way more experienced.” He confidently states as he peers into her eyes.
“That’s what matters.” Emmy speaks softly as she smiles, tilting her head.
“So, tell me more about these experiences you have with older guys…” Jack takes another swig, intrigued and turned on by her.
“Um… I don’t know what to say.” Emmy giggles playfully. “I’ve just been with a few.”
“I like a girl who likes older guys. I mean, of course I do.” Jack chuckles. Emmy grins as she drinks. “You mentioned you like being submissive in your email. Tell me more.” He demands confidently before finishing off his glass of wine.
“Well, um… I guess I just like pleasing a dominant man. An older dominant man.” Emmy smiles, feeling herself get a bit aroused. “I love making him feel like I’m his… Like I’m his play thing. I love… Rough sex.” She blushes a bit, feeling him stare at her as he smirks approvingly. “I love being manhandled by aggressive guys.” Emmy squirms a bit in her seat, uncrossing her legs.
A moment of silence passes. “Well,” Jack begins as he gets up, “sounds like we’re very compatible. We’re going to have a really fun time, Hayley.” He smiles down to her, extending his hand. Emmy smiles back, grabbing his hand and standing to her feet.
He guides her back to the window view. They stand parallel to the window. Jack puts his hands on Emmy’s hips and looks down at her. They stare into each others eyes for a moment, then Emmy looks down, breaking contact. They both smile. Jack’s hands rise up her body, feeling her torso, her chest, and up to her neck slowly. He feels the leather of her tight jacket. His hands rise up further to cup each side of her pretty head. He tilts her head up and stares back into her eyes. “I know this is your first time doing this but you don’t have to be nervous, OK? I’m gonna take care of you.” He says softly into her eyes. Emmy gazes back submissively, relaxing into his touch and soothing, confident voice. Jack kisses her softly on the forehead. “So pretty.” He smiles slightly before stroking her bangs to the side with the back of his hand. Emmy’s little hand goes up to gently grasp his hand as he strokes her hair. “You remember everything in my email?” He asks.
“Yes…” Emmy replies softly up to him.
“You gonna do a good job of making me happy?” He asks confidently, smirking a bit.
“Yes.” Emmy smiles and nods. “I’m very good at what I do. I promise.” She says confidently. Emmy knows her sexual prowess but her timid and submissive nature typically gets in the way of being confident about it. “I really want to make you happy.” She purrs up at him softly and submissively. His hands have gone back down to hold onto her petite torso. Emmy’s arms go up to wrap around his neck.
“Good girl.” Jack smirks down to her. His head leans down to kiss her. They lock lips slowly and sensually for a brief moment. Emmy leans into him further and his hands go behind her. “You’re so fuckin’ hot.” He says in a horny tone as his hands squeeze her tight ass. Emmy leans up to kiss him more, moaning softly into his mouth. Her little hands go to his chest, feeling him breathe harder. He relinquishes his hold and they cease kissing. He rotates her and steps behind her, pointing her toward the view of the window. Jack holds her from behind firmly, her ass grinding against his crotch. He kisses her neck softly. Emmy moans as she feels her pussy tingle with arousal. His hands eagerly feel her firm chest. They both breathe harder. His right hand goes further south to rub the inside of her leg over her jeans while his left continues to paw at her perky tits. Emmy squirms against his body as his hand gets closer to her pussy. Jack stops suddenly, his hands going up to her shoulders. He kisses the back of her head, feeling her thick soft hair against his lips and smelling her intoxicating aroma. “There’s the sunset.” Jack says playfully as he kisses her neck again. Emmy looks out the window and notices it, smiling. He begins to whisper in her ear. “Let’s get started. I left something for you in an envelope on the bathroom counter-top. Go get ready for me, sweetie.”