“Oh yeah? Is that what you want, princess?” His eyes travelled over her body, pausing very obviously on the swell of her breasts and the tiny skirt before sweeping down her legs and back up again.
“Your go. You’re solids,” Jessie told him, ignoring his question.
The look he gave her was making her blush, not to mention the way it made her pussy tingle. She was pretty sure she could feel a wet spot forming in her panties right now and she instinctively squeezed her thighs together.
Jack stepped up to the table to take his turn, sinking a ball and then another before missing a shot.
Jessie got up to take her turn. Jack watched her bend slightly, his eyes all over her ass. Fuck. That ass was going to be his undoing one of these nights. She lined the shot up and leaned forward.
“Whoa, whoa stop. Let me show you something.” Jack came up behind her. “You’re holding it wrong.”
“Whatever, Jack,” Jessie said. “We don’t need to try to play like we’re professionals! Who cares? Let’s just play for fun.”
“Don’t you want to learn and get better?” Jack asked as he put his arms around her and took the stick out of her hands.
Jessie felt Jack’s body press against her, so close she could smell his clean scent.
Oh, she wanted to learn alright. Not necessarily about playing pool, but there were plenty of other things she was quite sure Jack could teach her.
She felt her heart rate pick up when his warm breath skimmed over her shoulder as he bent down to line her stick up correctly.
“Here, hold it like this.”
He placed her hands in the correct position but Jessie could barely pay attention to his instructions, she was so distracted by how close he was. He placed a hand on her hip and adjusted her stance, his hand dipping down and brushing against the bare skin on the side of her thigh briefly, lingering just a moment longer than he needed to.
Damn, she smelled amazing. When he stood behind her, his cock sprung to life just being so close to all that pretty skin and that sexy little body. When his fingers brushed against her silky thigh and his eyes skated down over her sweet little ass, he had to work to keep control before his dick got hard enough to cut fucking glass.
His head might know that fucking Jessie was out of the question, but his body wanted what it wanted. And fuck if his cock hadn’t set its sights on finding out how good it would feel to be buried deep inside Jessie.
He felt her shiver slightly as she clumsily almost dropped the stick.
“You okay?” Jack looked down at her, smirking slightly.
“Yes… I’m f-fine,” Jessie stammered, avoiding his eyes.
He was looking right through her, like he knew exactly what he was doing to her.
He went back to the table and picked up his drink, his eyes dark and fixed on Jessie as she took her shot. She sank the ball, but scratched.
Jack briefly imagined pushing her down to her knees, pulling those pigtails hard as he shoved his cock into her mouth, those blue eyes looking up at him as he came all over that pretty face.
Fuck, she had him horny as all hell tonight. He could barely focus on anything else.
They played game after game, Jack winning every time, but Jessie getting in a good shot now and again. Jack laughed and rolled his eyes at the way she shrieked with victory when she occasionally sunk a lucky shot, celebrating by jumping up and down and high-fiving everyone.
The cute guy that had been talking to her earlier in the night never came back, and a couple of hours later, Jessie spotted him in the crowd, making out with a brunette in a naughty nurse costume.
She sighed, disappointed. Really? She was dressed in the sexiest costume she had ever worn for Halloween and besides that one guy, no one had even approached her.
“Something wrong?” Jack asked, coming up behind her and looking in the direction she was facing to try to see what she was staring at.
“No,” Jessie said, turning around.
“Oh, I see. Your guy found someone else to hook up with?” Jack teased her.
“He isn’t my guy. I just met him tonight. I only talked to him for like five minutes. And I couldn’t care less.” She sounded defensive and Jack laughed.
Zoey came and stood beside her.
“He probably thinks you’re here with Jack. I mean, you guys haven’t left each other’s side all night. Jack—go away!” Zoey said. “Come to the ladies room with me, Jessie.”
Jack’s eyes never left Jessie’s ass as she walked away.
Chris noticed and called him out on it.
“Dude, what’s up with you tonight? You’re staring at Jessie’s ass even more than usual.”
Jack kept his eyes on her. “She’s got it hanging out more than usual. It’s got me in the mood for some naughty schoolgirl action tonight, that’s for fucking sure.”
Chris laughed. “Lucky for you there’s plenty of naughty schoolgirls here to choose from. Ones whose names are not Jessie and won’t mind you using them like a living sex doll.”
Jack smirked and sipped his whiskey. “Dude, relax. I’m not going to fuck with Jessie.”
Chris let out an exaggerated sigh of relief. “Whew. You had me worried there for a minute.”
“But fucking Christ, she’s got an unbelievably fantastic ass on her! I mean, seriously, maybe the best ass I’ve ever seen. And that fucking outfit… if she was any other girl I’d already be tearing it up, I can guarantee that. I wouldn’t give a fuck how inexperienced she is.”
“Last thing she needs is you fucking with her head. I’m sure you won’t have any trouble finding someone else tonight. This place is crawling with chicks.”
Jack shrugged and finished his drink. “I get it, alright? Nobody knows better than I do that I’m not good enough for her. Don’t need you reminding me every fucking time I turn around.”
Chris raised an eyebrow, surprised by Jack’s reaction. “Just looking out for her, brother. I see the way you look at her. And it’s not about being good enough, it’s about being what she needs. You’ve said it enough times yourself that you don’t want a relationship. Am I wrong?”
Jack shook his head. “Nope. You’re exactly right.”
He made his way to the bar to get another drink for himself and for Jessie, and that’s when he saw her. Bingo. A blonde in a naughty schoolgirl outfit almost identical to Jessie’s. Good looking girl with a great body, that sexy fuck-me look that always got his motor running.
He made eye contact and she smiled at him. He stared, giving her the confidence to approach him. Ten minutes later she was following him out of the bar.
He had her wait by the door while he went to grab his jacket and say goodbye to Jessie, Chris and Zoey.
“Taking off. See ya’ll later,” Jack said, setting a fresh drink down on the table for Jessie.
Jessie looked up in surprise. “You’re leaving? But I thought… we’re in the middle of a game and…”
“Gotta go.” Jack cut her off, leaning in to give her a quick kiss on the cheek and patting her back briefly. “Be good, princess. Try to stay out of trouble in that little outfit. Don’t want to have to come back and kick the shit out of someone for mistaking you for a bad girl.”
He slapped Chris on the back. “Make sure our little honor roll student makes it home before curfew.” He lowered his voice so Jessie couldn’t hear him. “Our little princess is safe tonight… there’s my action for tonight.” He smirked and nodded toward the blonde waiting for him at the door.
Jessie’s heart sank as she watched him walk out with the blonde wearing almost the exact same outfit as she was wearing.
She felt a familiar pang nagging in her chest. Zoey put her arm around her, sensing her disappointment.
“Jessie, he’s such a whore. You’re better off. You know what he’s like.”
Jessie shrugged, blushing. “Whatever. I know that. It’s not like I want to be another one of Jack’s conquests or anything. It’s just that… I mean, he spent
the whole night hanging out with me and I thought… well, we were having so much fun all night and then he literally only talked to that girl for like, two minutes. And the fact that she was wearing a costume almost exactly like mine… ugh, I’m so stupid for even caring!”
“If he had talked to her for more than a couple of minutes he’d probably be irritated by her and would have moved on to someone else,” Chris offered. “But I promise you, Jessie, it’s for the best.”
“It’s actually disturbing how much that girl resembled you. I mean, obviously you’re prettier, but she sort of looked like a less attractive version of you.” Zoey rolled her eyes.
“Do you think so?” Jessie asked. “I’m not sure whether that should make me feel insulted or flattered.”
Chris smiled sympathetically. “He’s doing you a favor, you know. By staying clear of you. Trust me, Jessie. I’ve known Jack my whole life. He knows his limitations. He’s not cut out for a girl like you. He knows you’re not someone he can just bang and walk away from. It’s too much commitment. It freaks him out.”
“You’re never going to meet anyone if you spend every minute with Jack,” Zoey complained. “I mean, seriously, what guy is going to come up and talk to you when it always looks like you and Jack are together.”
Jessie sighed. “I know. You’re right.”
“Of course, I’m right. Now do a shot and forget about Jack!”
JACK SAT ON THE COUCH in the blonde’s apartment as she stood in front of him, twirling slowly so he could enjoy her costume a bit longer. She was hot. She didn’t pull this schoolgirl look off quite as well as Jessie did, but almost.
“Bend over.” Jack’s voice was hard and demanding.
She complied, bending over slowly so he could get a good look at her ass. He rubbed his hand over it and then slapped one cheek lightly before rubbing his fingers over her panty-covered pussy. She moaned.
He thought about Jessie bending over that pool table earlier, her ass teasing him from under the bottom of her little skirt. Goddammit, he wanted to spank that sweet little ass until she fucking begged him to touch her.
Fuck. She was always around, teasing him, looking at him with those amazing eyes. How was he supposed to stay away when she was practically presenting herself to him on a silver fucking platter?
Sometimes it seemed like he didn’t want anything more than he wanted to see what Jessie looked like underneath those clothes. Find out what she would feel like, taste like, what she would sound like when she came.
He pulled the girl down so she was lying across his knee and alternated between spanking her and rubbing her pussy through her panties.
“You’re a bad girl, aren’t you?” Jack’s voice was rough.
“Oh yeah,” she moaned. “Such a bad girl. Spank me.”
She moaned each time the palm of his hand made contact with her skin. He pressed one finger inside of her, then two, in and out. He removed his fingers to slip off her panties and then spread her open, staring at her pussy. He slid his fingers back inside of her and finger banged her until she was dripping wet all over his hand and his jeans.
“You’re fucking soaked… just like a good little slut, huh? Nice and wet for me… can’t wait for me to fuck that slick little snatch, can you?”
She moaned. “You’ve got me so fucking horny. I just want to fuck.”
She sat up and removed her top. He rubbed her tits, his fingers playing with her nipples. When she went to remove the plaid schoolgirl skirt he stopped her.
““Leave it on,” he demanded roughly as he ran his hand down her leg over the silky thigh highs. “Leave these on, too, and the heels.”
When he finally pressed his condom-covered cock inside her pussy, he closed his eyes and let himself think about Jessie. He didn’t even try to fight it like he usually did. He thrust in and out of her wildly, pounding into her as hard as he could, imagining that it was Jessie beneath him. He was claiming her, making her his. Those were her moans of pleasure and it was her body trembling and coming from his touch.
“Fuck, yeah! Jessie!” Jack growled as he came, snapping his hips in a punishing thrust as he pounded himself into the nameless, faceless blonde underneath him. In his mind it was Jessie’s pussy he was drilling himself into.
“Jessie, huh?” the girl whispered after he came. “That’s okay. I can be whoever you want me to be.”
He had thought getting laid would make him feel better. It hadn’t.
In fact, he felt like shit. What was this heavy weight that had settled in his chest? It was almost suffocating.
Jessie.
Jessie’s face flashed in his mind and it seemed like all he wanted to do was get the fuck out of there. He got up and started pulling his clothes.
“You’re leaving?”
Jack nodded. “Yeah. Sorry, I got to get home.”
Fuck.
Would he ever stop thinking about Jessie this way? Why was he such a fucking asshole? She was literally one of the best friends he had ever had. She had done so much for him, been there for him through everything with Kennedy, and treated him so goddamn good even though he had never done a thing to deserve it. And instead of treating her with the respect she deserved, he spent most of the time imagining fucking her like he would some little slut. Wondering what her pussy was like, what it would be like to tear into her and feel her come all over his cock, fill her up with his come.
Jessie deserved to have everything she wanted, including a guy who treated her like a princess. Not someone like him. No, he was like his father. No good for any woman with a heart like Jessie’s.
He would never do to a woman what his father had done to his mom. His father had taken advantage of all of the good in his mother, so he could keep the perfect, sweetheart of a wife at home keeping his bed warm and raising his kids, while he rolled in the gutter with whores. If Jack wasn’t careful, this thing he had for Jessie could easily turn into something like that, with Jessie at the short end of the stick.
Chapter Six
TWO WEEKS LATER, JACK WAS tucking Kennedy into bed.
“Night, Jack,” Kennedy giggled.
Jack tickled her gently as he leaned down and kissed her forehead.
“Goodnight, angel.” He swept his hand over her soft hair. “Get some sleep.”
He came downstairs where Jessie had already finished cleaning up the toys and coloring books that she and Kennedy had been playing with all evening.
“You didn’t have to do that,” Jack objected. “I would have cleaned up.”
“It’s okay, no big deal, Just took a minute.” Jessie smiled as she put the last Barbie doll away, into the wood toy chest that Jack had made in his workshop. She ran her fingers over the big heart that Jack had carved into the front of it.
“It’s your turn to pick the movie,” Jack said, heading toward his bedroom. “Just going to go change real quick.”
As he left his bathroom he noticed a hair tie and tube of some kind of lip balm on the counter next to the sink. Along with the pink toothbrush that now stood up right next to his in a holder, it was starting to look like he had a girl living here.
He sighed and picked up the items, pulling a drawer open so he could drop them inside. A glance inside the drawer revealed a small box of tampons. More girl shit.
In his closet he opened a drawer for a pair of pajama pants and found that Gwen had done a little rearranging. A quick check revealed that she had consolidated his things so that one drawer now contained random articles of clothes that Jessie had left scattered around the house. A sweatshirt, two pairs of socks, a pair of fluffy pink pajama pants with hearts all over them, a white lace bra and three pairs of panties, two white cotton and one a white lace thong. He ran his fingers over the lace and soft cotton and sighed.
She spent so much time here it made sense that she would have left things behind. And it was convenient for her to have a few things here anyway.
Returning to the living room, Jack sat down next to J
essie on the couch. He rolled his eyes when he saw the chick flick she had chosen and reached for the bowl of popcorn she’d made.
“Really? An Officer and a Gentleman? Going to make me sit through this bullshit?”
“Whatever… you forced me to watch that awful Conan the Barbarian movie the other night. Payback’s a bitch!” Jessie laughed.
When the popcorn was gone, Jessie took the bowl to the kitchen and set it by the sink. When she returned, Jack wound his fingers through hers and tugged her down on the couch next to him.
“Will you rub my back?” he asked, giving her a guilty smile.
Jessie nodded and reached for him. “You know, technically you owe me a massage. Don’t think I’ve forgotten.” She pressed her fingers into the muscles of his back.
He groaned. “Fuck that feels good.” He shifted slightly to give her better access. “You can collect yours anytime you want, just say the word.”
“Okay, you can do me when I’m done with you,” Jessie replied.
“Such a little tease,” Jack laughed and caught her around her waist, pushing her down on the couch and tickling her until she begged him to stop.
“Stop! We’re going to wake up Kennedy!” Jessie laughed.
““No we won’t. You know she only wakes up if she has a nightmare. Otherwise she sleeps like the dead,” Jack argued, but he let her go and rolled on his side. He adjusted her gently so she was lying on her side as well, facing away from him.
“Your turn,” he said gruffly, as he began rubbing her back.
She moaned with pleasure as his hands worked the muscles in her back. He felt his cock grow rigid in response to both those sexy little noises as well as way her body felt as he rubbed his hands over her. He dipped his hands as low as he dared to, rubbing them across the top of her ass. Fuck, she felt amazing. He forced himself to ignore the way his heart was pounding with excitement, not to mention his monster of an erection which was desperately straining in Jessie’s direction.
Jessie was so relaxed from Jack’s massage that she fell asleep. He gently scooped her into his arms so that he was spooning her, one arm underneath her, the other resting lightly around her waist. He closed his eyes and tried to clear his mind, willing his body to calm down.
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