Jack let out a loud groan, his hands gripping at the shoulders in front of him. He tossed his head back slightly, letting the pleasure consume him as he felt sharp nails dig into his buttocks. He felt the urge to thrust his hips, but knew he would get yelled at if he dared move, so he kept his ground, biting his lip to suppress any movement. He gasped and then shuddered when he felt the tongue wrapped around his shaft move down to his balls, the mouth suckling as the hand pumped leisurely.

"Ahh, oh my- I'm gonna cum," he breathed out, feeling his orgasm rise within him.

"Don't you dare," a voice said below him, muffled by his flesh.

He squeezed his eyes shut, trying to hold off. "P-please let me cum!"

"Look at me."

He forced his eyes open and looked down just in time to watch Karen's mouth take him all the way in, sucking hard while she bobbed her head back and forth at a steady pace. They locked their eyes on each other and Jack tangled his fingers in her brown locks, his body going stiff as he finally came, shooting jets down her throat. Karen swallowed it all, moaning in appreciation. She pulled back, letting him go with a 'pop' and then took him in again, licking him slowly until he softened in her mouth.

He didn't push her away from his sensitive cock, knowing she would punish him if he did. She would move away when she was ready to and he honestly didn't mind the torture, teetering on the boarder of pleasure and pain. He watched her adoringly, his fingers stroking through her hair as she stroke him with her tongue. With a final moan, she pulled away, placing a delicate kiss to the head before she tucked him back into his boxers and zipped up his pants. He helped her up from her knees and leaned down to accept her kiss.

"Mmm, I love your cock, Jackie," she moaned into his mouth. Her tongue sought his out and they made out for a few minutes. Karen was the one to pull away, giving him a little wink before she walked away towards his bathroom to fix her makeup.

When Jack heard the click of the lock sliding into place, he leaned heavily against the front door of his apartment, swiping a hand across his face as he took in deep breaths. This all started months ago. One night Jack had asked if she was any good at blow jobs. Instead of telling him how good she was, she decided to show him instead. And now, months later, they couldn't get enough of each other.

But Jack was beginning to feel bad. Karen always got him off, doing wicked things to his cock, but she knew he was uncomfortable when it came to a woman's body so she would scamper off to a different room to take care of herself. She deserved more. He realized more recently that he couldn't be that replused by a women's body if he was easily getting off with Karen. His favorite thing she did to him was when she gave him a titty fuck. He loved her tits, loved to play with them, but he especially loved when his cock was between them, her mouth wrapped around the head.

One time, when she was finished with him and excused herself to the bathroom, he followed her, pressing his ear to the door, listening to her high pitched moans. Curiosity got the best of him and he turned the knob, peeking inside. He saw her sitting upon the sink with her hand under her skirt, her panties shoved in her mouth to stifle the loud sounds of pleasure escaping her. Her eyes were closed and her eyebrows knit together as she concentrated on finding her release. Jack felt a stir in his pants and quickly, but quietly shut the door, surprised at his body's reaction. He had suddenly felt the urge to go to her. He wanted to be the one to bring her that pleasure. He wanted to know what she looked, felt, and sounded like when she came.

Hearing the bathroom door open, Jack snapped from his thoughts and watched as Karen emerged from the bathroom, her makeup flawless and hair back in place. She gave Jack a devious grin as she stepped up the kitchen steps to grab herself a drink. Jack quickly followed, hovering over her as she made a martini. He was nervous, not exactly sure where to put his hands or what to say.

"K-Kare?" he asked tentatively.

"Yeah, honey?"

He licked his lips, his nerves getting the best of him. "You know how you're always taking care of me and then you run off to... take... take care of yourself because you don't want to make me uncomfortable?"

Karen stopped making her drink and slowly set the martini shaker on the counter, looking over her shoulder at him. "What are you saying, Jack?"

Jack gulped, mustering up the courage to finish what he started to say. "I don't want you to run off anymore," he blurted out. Karen turned to face him in shock. He continued before she could speak up. "I want to help you like you help me. I want to know what you taste like. I want to watch you when you cum... "

Karen just stared at him, her jaw dropped. She licked her lips and shook her head, trying to wrap her brain around the concept. "So you wanna... fuck me?"

"Oh God no!" He exclaimed, placing his hands on her shoulders. "No. I love you, but I don't think I could ever have sex with a woman." She deflated, but he wasn't sure if it was from relief or disappointment. "But I do want to pay you back."

"Jackie," she smiled. "You don't have to-"

"I don't," he agreed, cutting her off. "I want to."

Minutes later, he had her naked and on all fours on his bed. Her ass was red with his handprints. He knew Karen liked it rough from the many stories she told him of her sexual trysts and be wanted to make this experience just as pleasurable for her. She was gripping the sheets, her pussy dripping with arousal. Jack, sitting on his knees behind her, tapped her thighs, telling her to spread her legs further apart. She complied and he smirked, placing his fingers at her entrance.

Karen whimpered and gasped as he teased her, his fingers tracing her lips, but never going to where she needed them most. "Jack, please," she begged, her chest heaving with deep breaths.

Jack smirked and relented, pressing two fingers against her swollen clit. She shuddered and moaned as he drew circles into her. He continued to tease her for a bit, bringing her to the edge and then slowing down. She was getting more and more frustrated with each passing second. Just as she was about to snap at him, Jack slipped two fingers into her and twisted them down, pumping them wildly into her. Karen cried out, the pleasure consuming her. She arched her back up and began to squeeze her knees together as she felt the orgasm tingle up her body until it finally erupted and she screamed. She contracted around him, squeezing his fingers tight.

"Come on, Karen," Jack said with a sly grin. "You can do better than that." He added a third finger and moved his hand even faster than before, applying pressure to her G-spot.

Karen was still trying to catch her breath from her first orgasm when her second ripped through her twice as intense. "Ohhh my gaahh- JACK!" She sobbed, her muscles contracting and pulsating.

Jack grinned triumphantly when she began to squirt, coating his arm and the sheets. "There you go," he said. He pulled his fingers out and smacked her clit a few times causing her to squirt a little more. Karen fell to her side on the bed, trembling as little jolts of pleasure continued to shoot through her body. Jack crawled up next to her and rubbed her back soothingly. "You okay?"

She nodded, taking in deep breaths. "Fuck," she gasped, glancing up at him. "That was incredible."

"Yeah?" he smiled shyly down at her. "Was I that good?"

"Oh honey, I saw stars. And I don't mean figuratively. I was fucking flying."

Jack let out a laugh and settled himself down under the covers next to her, pulling them up over their shoulders. Karen scooted herself back against him and sighed in content. "So now every time you do something for me, I'll do it right back."

Karen looked back over her shoulder at him again. "You know I told you that you don't have to."

"And I told you that I want to, Karen," he said with a shake of his head. "You're my best friend. We know everything there is to know about each other."

"So," she frowned and turned over in his arms on her back so she could look up at him. "What are we, friends with benefits?"

Jack contemplated the phrase for a moment. "Yeah, I guess we are."

"Well good," she grinned and reached up to peck his lips.