Nicole was snuggled into Jack's side, her head in the crook of his shoulder, his arm draped around her when she felt him playing with her breast, rubbing his palm over her nipple. It felt pleasant and she kept her eyes closed as he worked her nipple to a hard point. Her head seemed to fit perfectly, as if that place where his arm and chest met was specially designed for it. She loved falling asleep this way, her arm across his waist, holding onto him. Jack rolled her over onto her back, change the angle between them, and his hand now traveled down her body, wedging between her legs, fingers running through her slit. She felt herself growing wetter with each pass, the feeling of his touch radiating through her body in the most amazing way. She couldn't help but moan.
"Ah, do you like waking up this way?" His voice sounded like he was smiling. She wanted to say that it definitely beats waking up to his cock smacking her face, but held her tongue. Instead, her confirmation was only slightly more than a moan.
"Mhmm," she rubbed her hand over his chest.
"Of course you do, horny little girl. You probably enjoy all of this just as much as I do." She opened her eyes to look up at him, he had a smug grin on his face and she considered what he had said. She enjoyed most of it. The way he touched her almost always felt good and sex, even when he pounded her hard and fast, was rather pleasurable as well. She felt a certain pride in the way she was able to please him with blow jobs now, where she could almost always take him in all the way without gagging and when she was able to make him come without him even intervening. She tilted her eyes up at him as he shot straight down her throat and she swallowed around his cock, not missing a drop. Nicole felt satisfaction at being able to do that. There have even been moments when she'd see his basketball shorts straining with an erection and she'd suddenly feel her own thighs clench and her pussy tingle at the thought of having him inside her. He flung the comforter open and shifted her on top of himself. "I want you to go for a ride on my cock," his hands spread her open to him and he slid his cock inside.
Yeah, this felt really good, she liked this. Her hips ground into him and she lifted herself up, pressing her hands into his chest. His cock filled her so perfectly, stimulating the sensitive parts inside her in this position. She closed her eyes momentarily, feeling fantastic. Jack pumped into her slowly from below, holding onto her hips.
"I have an idea," he told her and her eyes opened to look at him. "We're gonna make a little game out of this. Your goal is to make me come and mine is to get you to come. If you succeed first, you win and we are done, for this morning. If I get you to come first, I get to pick another hole and we go again. Same rules. If I come in the second hole first, you win, we're done. If you come first, I get to pick another hole." He was grinning big. She wasn't sure about this. She hesitated, looking at him. "This isn't really a question, I'm just letting you know what we're doing," he clarified.
She drew in a breath as she felt Jack thrust up sharply from below. She ground down to meet his thrusts while his hands shifted up to her breasts grasping them firmly and twisting her nipples between his fingers. She whimpered at the feeling. He was bringing her closer to an orgasm and she was bound to lose at this game. She reached behind herself to grasp Jack's balls and massage them in her hand. He grabbed her wrist and pulled it away, bending her arm behind her back. She squirmed, trying to get free while he landed a slap on her ass with his other hand. Unfortunately for her, she found a certain amount of arousal in being spanked, the sting of it sending tingles down to her pussy. She was so close, she could barely concentrate on keeping her composure. She tried to pull away, delay her own orgasm at least, if not actually make Jack come. He slammed her back down onto his cock, his hands firm on her hips, and she couldn't hold it back anymore. Her body shuddered around his cock, her pussy squeezing tightly around his thick shaft, and her only hope now was to have him come with her. She ground her hips into him, reaching for his balls again. He caught her hand as soon as she touched his sack, laughing.
"Oh man, you're really into this, huh?" He held her hands behind her back while she sat straddling him, his stiff erection still inside her. "Is it just that you don't want me taking you in another hole? Or that there's a little competitive edge in there, that you just have to win, even if it costs you an orgasm?" His eyes shone as he looked into hers. She wasn't sure which it was. Maybe a little bit of both. She shrugged. "Alright, well, you lost round one, I get to choose another hole," he continued grinning. "Which should I choose, your ass or your mouth next?" She didn't reply, avoiding looking him in the eye. He rarely wanted her to actually respond to these questions and if he did, he specifically prompted her to answer. "Well come on, I'm waiting. Which would YOU rather?"
"My mouth," she answered quietly. They've had anal sex again since that night that he was angry with her and it wasn't as painful other times, but she honestly thought she had a better chance at winning if she had him in her mouth!
"Alright, mouth it is! Good choice," Jack lifted her up off his cock by pulling up on her hips. "Because then when you lose, again, I'll take you in the ass last and you won't have to go from ass to mouth." He chuckled. "Let's do this..." he considered the position he wanted for a moment, "on your back."
This was the way he frequently woke her up in the morning, she'd be laying on her back and he'd kneel next to her and drag the tip of his cock over her lips. She had some control in this situation, some room to maneuver, but it was limited. He'd usually place a hand behind her head part of the way through, pulling her onto his cock or keeping her from moving away while he thrust into her mouth. She assumed he wouldn't be doing that now if he intended to make her come before he did.
He kneeled next to her, his cock jutting out towards her face and Nicole didn't hesitate to put her mouth over it. It smelled and tasted of her pussy, but she had gotten used to this by now. Recently, Jack had gotten into the habit of having her lick his cock clean every time he came inside her, whether it was in her mouth or in her pussy. She went to work immediately, sucking and licking, moving her head up and down his shaft. For a moment, it seemed like Jack wasn't going to do anything, like he was just going to let her suck him off. His hands remained hanging at his sides. She redoubled her efforts, reaching a hand for his balls once more, with the goal of getting him to come. He smirked, taking her hand away from himself. He grasped both of her wrists and arranged them into one of his hands, pinning them above her head. His other hand reached down to her pussy, fingers gliding between her folds and his thumb coming to rest on her clit.
It was much harder to move with her hands restrained. The way her arms were angled above her head made lifting her head to slide her mouth up Jack's cock more difficult. She found herself essentially stuck with her mouth part of the way up his shaft and his hand mercilessly fucking her pussy. She tried her best to lick and suck the part of his cock that she could get to, but he was in a much better position to succeed in this round. He had two fingers vigorously fucking her pussy why his thumb rolled over her already tender clit, flicking it and pressing into it. She whimpered, feeling helpless and so close to coming. She tried to shift her hips away from him, to somehow pivot her body, but his hold on her was firm and nothing came of her efforts.
"Are you getting nervous that I'm gonna fuck your ass?" Jack was looking down at her, his hand not slowing down one bit. She didn't respond to him. Her tongue was getting cramped from all the swirling around Jack's cock and she was still no closer to getting him off than when she started. "Cause I'm gonna make you come right now and then I'm gonna fuck your ass," he was grinning. "Your super tight, little asshole. Fuck, I should have started stretching it ahead of time," his fingers slipped out of her pussy and moved lower, circling her rear hole. His fingertips pressed firmly against it while his thumb remained unrelenting on her clit and the combination pushed her over the age. She moaned around his cock while her body spasmed and shuddered and Jack simultaneously pushed a finger past the tight rim into her ass.