Milking Assistant Ch. 02

Jess picked up her skirt and placed it on the meeting table, then took a seat at the other end of the couch.

"Does that thing ever go down?" She asked, pointing at the bulge in his pants.

"Not around you." Jack said, taking in the sight of the gorgeous woman in front of him.

Jess simply smiled and patted the couch again, inviting him to start on her other breast.

Jack happily obliged, placing his head down on the top of her stockings. The lace of her panties only inches away as she lowered her breast into his mouth.

Jack opened his mouth and took her other nipple in; it was already leaking from him playing with it. An immediate rush of milk filled his mouth, spreading across his tongue as he started swallowing. He couldn't believe that she had undressed in front of him so casually, letting him rest his head against her almost naked lap. She smelled different without her skirt on, more raw, more natural. It made his cock twitch, aching in his pants again.

Jack suddenly felt a hand on his cock, Jess seemingly sensing his discomfort.

"Let's give this guy some fresh air." She whispered, unbuttoning his pants and lowering the zip.

Jess reached into his underwear, her smooth hands sliding over the shaft of his rock-hard cock. She wrapped her hand around it and pulled it free from his underwear.

"Now that is a nice cock." She said, slowly sliding her hand up and down the length of it.

Jack's eyes rolled back in his head as he reached for her other breast, immediately stimulating her other nipple as he continued to suck milk from her. Jess started jerking him off, her hand firmly grasping his cock, her nails occasionally reaching out and stroking his balls.

"Does milking me turn you on this much?" Jess teased.

Jack nodded his head, refusing to unlatch from the nipple.

"Well, I guess I'll just have to make you my personal milking assistant." Jess said, picking up the pace of her hand around his cock.

Jack moaned with her nipple in his mouth, her words sending shivers up his spine. He was so incredibly turned on by the situation, he could feel his balls beginning to tighten, preparing to come.

Jack felt a hand slide past his head as Jess slid a hand down her panties. He watched as she slowly started to rub her pussy underneath her white lace panties.

"Are you going to come for me?" Jess whispered.

That was all that Jack needed, his balls hugged tight to his body as he started to convulse. His eyes clenched shut as his cock began to erupt with cum, spraying rope after rope against Jess' hand and the couch. He turned his head involuntarily, a loud groan falling out of his mouth as he exploded with an enormous orgasm.

Milk ran out of Jess' nipple, dripping onto his face and running down his cheek as he twitched in the aftermath of his orgasm.

Jack's world went dark for a moment, nothing outside of that office existed for a few moments as he processed his climax.

When he opened his eyes, he looked up at Jess, her breasts still dripping onto his face. She was casually licking his cum from her hand, smiling at him while she did so. Jack's cock twitched again, the sight of her tasting his cum was enough for it to start to harden again already.

Jess' other hand began to move as she removed it from her panties. She gently placed her wet fingers across Jack's face before sliding them into his mouth. He smelled her aroma and tasted the juice from her fingers, eagerly sucking at them, trying to memorize the flavor.

"Only fair that you get to taste me too." She said, pushing her fingers deep into his mouth, then sliding them all the way out.

Jack looked up at her, in complete awe. There was something so deeply sexual about her, everything she did was dripping with sexuality, and Jack wanted to lick all of it up.

"Okay, you're on clean up duty again." She said, shifting her body weight to stand up.

Jack lifted his head, letting her stand up. He looked at the mess that he had made on the couch and knew that he needed to clean it up quickly. A puddle of his cum sat on the cushion of the couch, more of it dripped slowly down the back cushion.

Jess pulled her skirt over her panties, her bra and shirt followed soon after.

"I need to make my train." She said, straightening her hair. "I had a wonderful time though."

Jess moved towards him and kissed him passionately, her tongue pushing its way into his mouth. She reached down and grasped his shaft one last time, squeezing it firmly.

"Thanks again." She said, turning and leaving the room.

Jack heard the elevator door shut as she left the office, leaving him with his cock out and a couch covered in his cum.

Jack put his cock away and went to retrieve paper towel again.

He gathered his things and headed to his car. It wasn't until he was driving that the reality of the situation hit home. A smile spread across his face, his cock twitching as he thought about Jess sliding her pussy covered fingers into his mouth.

He couldn't get her off his mind for the rest of the night.

Jack knew he was falling for Jess already, and he didn't care.

Annabelle Lace