He wakes up

Caleb was having a fantastic dream. He was seated upon a throne with dozens of women spread out before him. Those women were writhing around licking, sucking, and fucking each other as he watched. The massive lesbian orgy was being conducted to determine who would be his Harem Queen. Every woman he knew was before him, all of them vying to be the one chosen.

As he looked around he found himself to be indecisive. Did he want the most submissive woman? The most beautiful? Did he want a dominate queen to keep them all in line, or a nasty slut that would do whatever he wanted?

It was then that one particular couple drew his eye. Katie Mitchel, the schools lifetime sports coach, was using a strap-on to fuck Heather Carr, the cheerleading captain, in her ass. He could almost make out the verbal **** the coach was raining upon her. What really caught Caleb's eye was the playful smirk on the coach's face.

That smirk had launched many a masturbatory fantasy among his peers. She was a beautiful blond in her mid twenties, with breasts the size of honeydew melons, and a cute round rear that begged to be smacked.

Caleb watched the couple for a while. Heather was screaming and crying out, whether in pleasure or pain he could not tell, and wasn't sure which he preferred. Coach Katie, as she insisted on being called, was kneeling behind Heather ramming her with the strap-on. She had Heather's ponytail wrapped around one hand while her other was clamped around her wrists. She was pulling both hard. Heather's body was arched back, her neck stretched as far back as it could go. The unrelenting pounding in her ass was reverberating through her body causing her tits to bounce as if they were subject to anime physics.

All through the pounding, Coach Katie was watching him, that sexy smirk upon her lips. Caleb was hard as steel, his erection standing proudly before him. Caleb wanted to wipe that smirk off her face. He wanted to ram his pussy stretcher into her and make her scream in ecstasy. Though no one was close enough to touch it, he felt as though there were several hands, and sometimes even a mouth, upon his cock.

"Mom, I think he is waking up."

"That's ok sweetie. Why don't you try sucking it again? Move your butt over there so you can get a better angle and see if you can take it any deeper."

The weight shifting on his bed drew Caleb awake. He opened his eyes and was greeted with the sight of something yellow and round. A brown teddy bear smiled back at him as he realized he was looking at his sister's panty clad butt next to his head. His eyes followed the contour of her fat rear and up her back to see she was topless. Her breasts dangling down forming a pair of plump cones, the areolas looked extra puffy, capped by delicious looking pink nipples. Continuing to sweep his gaze further along he saw his sister had a hand around his shaft and was lowering her head onto the tip. He noted a second hand, one with a wedding ring upon it, near the base of his shaft. Oddly, there was a smear of something blue on his shaft just above the hand with the ring.

He swept his gaze up the arm of this second hand to find it attached to his mother. Something about her looked off. She was wearing a satin nightgown that displayed a generous amount of cleavage. Her hair was mussed, but looking at his bedroom window he found it was still dark out. His sleep addled brain told him it was very early and a glance at his clock confirmed this. That explained her mussed hair, she must have recently awoke.

The amazing sensation on his mushroom head drew his eyes back to his sister. Her mouth was open wide as she made, "Gluck gluck gluck" noises. The pressure on his cockhead eased for just a second and his dick slid just a bit deeper into her mouth. Hazel quickly closed her mouth and pressed her lips tight against his shaft.

Caleb realized his cock was just barely inside her throat. He could feel it throb as his sister's tongue rubbed against his shaft. The sensation on his tip was exquisite. It was being gently squeezed and vibrated at the same time. Caleb could hear a slight noise and he realized those vibrations were a hum. His sister was giving him a hummer. He almost laughed but his enjoyment was cut short when she stopped and pulled her face off his cock.

"Look mom, I got at least an inch deeper that time! That's almost half way!" Hazel exclaimed.

"Oh sweetie I'm so proud of you," June said as she hugged her daughter. With their hands no longer holding him, Caleb noticed there was a neon green ring near the middle of his shaft a couple inches above the blue smear. There was another green smear a few inches from the tip. Looking at the women he finally figured out what was off about his mother. His sister was wearing neon green lipstick, while his mother wore blue.

"Doesn't it feel wonderful to set a goal and achieve it honey?", June said to her daughter, giving her a peck on the lips. "Now take a picture so we can finish him off and get our breakfast."