The most insane wingman in history

Jack lay in his bed staring up at the ceiling for what felt like an eternity. Fiona’s whorish moans of wanton excitement had echoed through the house for the first few hours as she was railed by Kelly, but after a time things grew silent and Jack slipped into a state of traumatic numbness.

There was a vague, distant feeling that he was still awake, but truly he wasn’t processing much of anything. The shock and grief of seeing the girl he loved reduced to a cocksleeve for his mother had been too much and his consciousness had retreated to a dark corner of his mind.

At some point-he couldn’t say when exactly-the darkness of his room was breached and a weight pressed down in the bed beside him.

“Sweetie?” The voice of his mother whispered, “are you awake?”

Jack didn’t have the strength to respond, merely laid there in his catatonic state.

There was a moment of silence and then he felt a soft hand on his chest, fingers spread out over his heart.

“I didn’t realise you’d be so upset,” she whispered again.

No response.

“Please …talk to me, Sweetie.”

The concern in his mother’s voice was enough to puncture through his numbness and coax him back to the present. His eyes focused and adjusted to the dim, and he saw his mother sitting at the edge of his bed, looking down at him with big emotional eyes. A T-shirt had been thrown on, straining against her massive tits.

“Why, Mom?” He asked after a small life time of consideration. “I wanted to ask her out for so long…”

“Oh, Sweetie,” she leant down a kissed his forehead as she had down countless times in his childhood. The gesture full of maternal affection. “I didn’t really think about that.”

“But really, Fiona was just a silly cockslut.”

The heat and aggression in her words alarmed Jack, snapping him out of his boyhood reverie. He also couldn’t help but notice his mother was completely naked below the waist, her flaccid cock resting on his sheets like a snoozing beast.

“She was so eager to gobble down my cock, to bathe my balls. But you know, when I got her on her back she was a terrible lay. Her cunt was tight, but the silly little bitch made me do all the work,” she clucked her tongue in disapproval. “I probably fucked a baby into her tonight, but it was probably a waste of good genes.” A maternal smile returned to her face and she leant down to caress his cheek and hair, “Fiona was no good in the end. Certainly not good enough for you, my baby boy.”

Jack couldn’t believe what he was hearing, there was something very wrong with his mother’s mind.

“But I understand I was very inconsiderate of my baby’s feelings and I’m sorry for that,” her eyes searched his own, “so how about I make it up to you?”

Jack could barely process his thoughts, let alone get out a cognisant sentence. “What do you…huh?”

“I’m your mother, and it’s my job to guide you through life, but I’ve neglected that. And without your father that’s been a struggle,” she sighed, before another smile tugged at her lips, “but thanks to my big fat cock I know how to help you become a big strong man.”

“Mom,” Jack said, “I’m not sure I understand what you mean.”

“Starting tomorrow, I’m going to help you get laid, Sweetie.” The words were said in such a pleasant, wholesome way, but that didn’t change the nature of them. “We’ll go out and I’ll help you find some nice pussy to fuck away into. There are a whole lot of sluts out there just waiting for a good dicking. Mommy will be right there the whole time, I’ll coach you through it. I’ll even let you try out a few of my side pieces if you like.”

Jack struggled to contain the fear and uncertainty that shot through him. How had his mother transformed so much in such a short amount of time? She had gone from his sweet, loving mother to some kind of futanari wingman?

He couldn’t even really wrap his head around it, but croaked out a weak “Ok,” unsure what else to say.

Kelly’s eyes brimmed with love. “This’ll be so fun Sweetie, I promise!” She pressed a series of kisses against his cheek and into his hair, a big adoring expression on her face. “It’ll be Mommy and her baby boy, her number one guy. We’ll be drowning in pussy, just you wait!”

As she walked out of the room Jack couldn’t help but notice her cock was standing to attention and that a trail of juice ran down her inner thigh from her otherwise neglected cunt. He was still processing that as sleep took him.