Milking Assistant Ch. 03

"There he is." She said grabbing his shaft firmly. "He's been very patient."

Jess pushed Jack backwards, making him sit on the couch again. Jess fell to her knees and moved between his legs, holding his cock the entire time. Without hesitation, she leaned forward and took Jack's hard cock into her mouth. Gently moaning as her tongue rolled across the head of his member.

"Jesus, Jess." Jack whispered, taken by surprise.

He was expecting to help her with her engorgement again, maybe get a hand job, but here was this incredible woman between his legs, with his cock in her mouth.

Jess took his cock deep into her mouth, sucking firmly, before bobbing her head up and down rhythmically. Jack felt his balls tighten immediately, the events leading up to this blow job already making him need to cum. Jess sensed this and slowed down, taking his cock out of her mouth and kissing the shaft gently.

"Mmm, it's been so long since I've had a cock." She said, taking the head back into her mouth.

Jack's eyes rolled back in his head, completely overwhelmed by the sensation. Jess' body rocked back and forth, thrusting her head down onto his rock-hard cock. Jack watched her, she was clearly enjoying herself as she sucked him, her head bobbing up and down. She looked up and made eye contact with him, the lust in her eyes exciting him even further.

Jess took his cock out of her mouth and leaned back, revealing her dripping nipples.

"Want a taste?" She asked.

Jess stood up, not waiting for an answer, and mounted Jack's lap. Her knees resting on either side of him, his hard cock pressed up against her stomach. Jess leaned forward and placed a breast in his mouth, a jet of milk instantly filling his it. Her hand grabbed hold of his cock and began stroking it while he nursed at her nipple.

"That's it, drain me." She whispered.

Jack reached up and started stimulating her other nipple, milk covering his fingers as he gently rolled it between his thumb and forefinger. Jess' hand picked up pace rubbing his cock against her stomach now. She let out a deep, primal moan as he sucked firmly on her thick nipple.

Jess sat up ever so slightly, her nipple still in Jack's mouth, and began rubbing his cock against her clitoris. Jack could feel the ball of her piercing against the head of his cock as Jess quivered with pleasure.

He looked up the beautiful woman that he was only an inch away from being inside. She looked so sexy and so powerful riding above him like that. Jess looked down at him and their eyes met.

They didn't need to say anything, they both knew what was about to happen.

Jess smiled as she angled Jack's cock a little bit further back, then lowered herself onto it taking his rock-hard cock into her wet pussy. She moaned deeply as she slowly slid down his thick shaft, her lips gripping him tight.

"Jesus." She moaned, "It's been too long."

Jess pulled her breast from his mouth and leaned back, focusing on riding him. She started slow, grinding against him while she took the entire length of his cock. Then she sat up and started bucking her hips, fucking him as deep as she could manage.

"Fuck me, Jack." She hissed, her pussy becoming wetter by the second.

Jack thrusted into her, pushing her hips down onto his cock, driving it deeper into her. Milk started dripping from her swollen breasts, flicking around and splashing them both while she rode harder and harder.

Jack reached out and held them, teasing her nipples as he drove his cock in and out of her. He knew he wouldn't last long; he wasn't sure if he ever could with such a sexy woman, but especially not today after such an intense session at lunch time.

"I'm going to come soon." He said, panting slightly.

"Cum in me, Jack." She said.

"Are you sure?"

"It will be fine, I'm still breast feeding." Jess insisted.

Jess started bucking harder, Jack's cock slipping in and out of her soaking wet pussy with ease. He felt that familiar feeling in his balls, the feeling that told him he was at the point of no return. Jess must have felt him swelling too, she leaned forward and planted a deep kiss on him. Her tongue meeting his in a moment of intense passion.

"Do it for me, Jack."

Jack felt the words flow from his ear, through his body and into his cock, which promptly erupted with cum. Jack convulsed as wave after wave of orgasm washed over him, cum pouring out of his cock and filling Jess' pussy.

"That's it, come in my pussy, Jack." Jess whispered, nibbling at the lobe of his ear.

Jack's vision blurred for a moment as the climax of his orgasm hit, his cock shooting out one last thick rope of cum inside Jess.

His limbs went limp, and his eyes shut, nothing else existed except for Jess and her wet pussy enveloping his cock. He felt her gently kissing his neck, her breast still dripping milk onto his chest and stomach.

"That was so good." She whispered, sitting up and letting his cock fall free.

Cum poured out of her as she stood up. Jess put a hand between her legs to catch some of it and licked it from her fingers.

"Tastes better when it's both of our juices." She said winking at him.

Jack's cock started twitching again at the sight of her licking his cum, but it had started to soften already. He couldn't believe what had just happened. He couldn't believe that he got to do these things with such a sexy woman.

He couldn't believe he had just cum inside his boss.

"I've missed my train." Jess said, looking at her watch. "Any chance you could give me a lift home?"

Jack's mouth wasn't working, he was still recovering from his orgasm, he simply nodded his head.

Jess leaned forward and kissed him, the taste of both of their fluids filling his mouth.

"I'll make it worth your while."

Annabelle Lace