Good Boy

*All characters in this story are over 18.

Jason walked alongside his best friend, Charlie, and Charlie's mother, Shelley, into 33 Bender Avenue—a run-down, low-income welfare building that smelled of foul deeds and garbage. They made their way into an equally decrepit elevator up to the ninth floor, where they got off and began walking to Charlie and Shelley's apartment.

"I hope she doesn't yell at us again," Charlie worriedly said. "She usually does..."

"Don't worry about that," Shelley assured her son. "If Norma opens that door, I'll beat the shit out of her, again."

Norma was the deranged, crazy lady that lived across Charlie and Shelley, and had apparently always hung around her peephole to yell at anyone coming or going from their apartment. Fortunately, this time they passed without incident.

"You guys go ahead and start watching," Shelley said as they entered the apartment. "Mommy's going to lay down for a while, so I won't be spying," she said with a wink.

Shelley had always allowed the two friends to rent whatever they wanted from the video store, which included her passing the curtains into the adult section and picking up a video for herself, that she didn't mind her son and his best friend to watch. As Jason once described her to Charlie, "You have the coolest mom ever!" Shelley was a somewhat short, but full-figured Filipino woman with tied back black hair and a perpetual smile. Her breasts were large enough to be admired by Jason, a handsome Indian young man, but what he really looked out for was the camel toe of Shelley's vagina peering through her usual white tights—a favorite attire of Jason's. "Tell your mom to wear those tighty whiteys," Jason would tease the soft-mannered Charlie.

The friends had finished watching Hannibal, which had just been released on VHS in 2001. Jason knew what he wanted to watch next. "Put it in!"

A porno centered around a big-boobed blond vixen being hired by a mother as a babysitter, and then seducing the father, involved her getting fucked regularly in her mouth and pussy. The grand finale was her taking the father's dick up her asshole, while he popped it out and stuck it in his wife's waiting mouth in a heartwarming menage.

"Man, your mom has the best taste in porn," Jason said.

"Yeah..." Charlie replied.

"You think your parents have ever fucked one of your babysitters?"

"I've never had a babysitter. Mom's always here."

"Or with anyone. You think they've ever had a threesome? Oh, what am I saying; your dad is never here, always driving his taxi. I doubt they've had a twosome in a while."

"I don't know," Charlie uncomfortably said.

In the heat of the porno, as the father in the film blew his load on the faces of his wife and the babysitter, a noticeable tent appeared in Jason's pants, while no such excitement was visible on Charlie's person. Though, the observant young man definitely took note of Jason's situation.

"Gotta go take care of this, buddy," Jason said, as he stood up and left towards the bathroom. On the way there, he passed by dated family photos, and stopped at a large one of just Shelley, a portrait taken when she was much younger. He pressed his crotch as he looked down the hall to see if Charlie was watching. Clearing the way, he leaned in and kissed the glass of the frame where Shelley's lips were. It then dawned on him that Shelley's closed bedroom door was right behind him, and he leaned against it to see if any action had been taking place inside. Alas, no moans, but with his raging adrenaline and excitement, he decided to open the door to take a look. There only lay Shelley face down on the bed, sleeping. But the white tights tightly raping Shelley's big butt, and the evening light coming in made it seem like she was totally bottomless. He fantasized about getting on top of her and going for it, with Shelley waking up with that typical smile on her face, begging him to continue fucking her. His hard-on was reaching maximum, and he had gotten what he had come for, leaving the bedroom and rushing into the bathroom—missing in the darkness that Shelley had passed out on top of her arms, with her hands in her crotch.

"They still haven't gotten a lock for this fucking door," Jason thought as he closed the bathroom door behind him. He lowered his sweatpants and underwear in one pull, and revealed his well-shaped, seven-inch brown dick, admiring his rather impressive penis, given the circumstances.

"These fuckers are always well-equipped," he whispered to himself as he grabbed a bottle of baby oil from the sink counter and poured generously on his rod.

He closed his eyes, began jacking his dick, and continued fantasizing about viciously penetrating Shelley in every hole, much like the blond porn star had been by the father in the porno. He imagined her smiling up at him as he fucked her, as in no matter how much abuse he dished out on her, it would just grow her sexual appetite in an endless session of raw, unadulterated sex. Jason pictured standing behind Shelley as soon as they walked into her apartment, ripping open the rear of her tights, and pushing his cock into her asshole as Charlie would sit down and watch a movie, occasionally looking over at his mom getting sodomized by his best friend. Shelley would then turn around, get on her knees, and suck Jason's dick like her life depended on it, her head bobbing back and forth like a punching bag, while Jason maintained eye contact with Charlie. Then Charlie would walk over, and—

The sound of the door opening, Jason breaking out of his fantasy and looking over, and Shelley looking right into his eyes all seemingly happened at the exact same time. She wasn't smiling this time.

The two looked at each other for what seemed like thirty seconds, but couldn't have been more than a few. Shelley then looked down at Jason's penis, still in his hands, and continued to stare. Finally, she walked inside the bathroom, and closed the door behind her. Jason's eyes followed her as she walked around him to the toilet, pulled her white tights and a white thong underneath down to her knees, and sat. They continued to look into each other's eyes as the sound of pissing seemed only to make Jason's penis even more stiff in the awkward situation. Shelley broke eye contact to grab a bathroom tissue, and wiped her vaginal area before flushing. She stood, pulled her thong and tights up, and walked behind Jason. She reached around, and with the same hand she wiped with, grabbed his dick and began jacking in normal, tempered strokes, as she began to smile. She lowered her head onto Jason's left shoulder, going cheek to cheek with him as she continued to masturbate her son's best friend. They made intense eye contact through the mirror, only broken when Shelley began turning into Jason's face and kissed his cheeks repeatedly.

"Good boy... good boy... give it to mommy," Shelley whispered in between her kisses.

The strokes became slightly quicker, and Jason's mouth was open as he helplessly surrendered his body to the older woman.

"You're so big! I had no idea! Mommy's so proud of you! Good boy!" Shelley muttered with Jason's oily, brown cock in her hands, before reaching around with her other hand and rubbing Jason's also lubricated balls in her hands.

"Ah... ahh... ahhhh... I'm cumming! I'm fucking cumming!" Jason whispered loud, before blowing several strings of thick, gooey cum into the sink as he looked up. Shelley continued to stroke him slowly.

After the storm had settled, Jason was turned around by Shelley and face to face with her closer than ever before, an odd, but much desired feeling for him. They reconnected with that same intense stare as when Shelley first opened the door.

"Anytime you want it, baby—don't ask. Just take," Shelley said seductively, before her smile turned into a devious smirk. Shelley left the bathroom.

Jason continued to enjoy the encounter a few minutes more, before returning to the living room, where Shelley had her arm around Charlie.

"Time for Hollow Man," Shelley said.

"I better go home," Jason replied. "Think I'm good for the night."

"That's too bad; there's a scene you would enjoy. Tell your mom I said 'hello.'"

Jason smirked. "Sure."

Shelley looked him into his eyes. "Good boy."