Ryan bolted up from his bed and tried to get his eyes to focus on the bright LED alarm clock—8:33AM. He was supposed to be up and out of the house by eight.
Shit!
Dressed in a T-shirt and loose boxers, he grabbed a pair of jeans and pulled them on quickly as he rushed out of his bedroom. He flew down the stairs, through the kitchen—past his mom and sister—and out the backdoor.
"Hey you dork," his sister called out, "it's Saturday!"
"I know," Ryan shouted back from the yard as he flipped up the kickstand of his mountain bike. This was Ryan's first summer back from college and he had taken a job at a clothing store in the local mall. Saturdays were his day off—so he wasn't headed to the mall. Instead, he was headed to his best friend Mike Lilly's house. Only Mike was on vacation in Europe with his wealthy girlfriend. So, Ryan wasn't on his way to see Mike. Instead, he was on his way to see Miss Madison Lilly—Mike's mother.
Miss Lilly was the MILF of the neighborhood. Indeed the MILF of the town. Everyone knew who she was—the busty blond woman and ex-wife of the town's ex-mayor. In her mid-forties—she conducted aerobics classes at the local health club that kept her well-tanned body tight, fit, and looking half her age. She made a modest income at the health club but lived lavishly off her ex-husband's alimony payments. As part of the settlement, she was also awarded the estate home in the divorce proceedings as well as a large portion of his wealth. Rumor has it that he was caught having sex with their Mexican nanny—Bianca. This was not a good fact when trying to garnish the sympathies of a female judge in a divorce trial.
Ryan hustled toward a shortcut that wound through dirt back roads leading to the walled gates of the Lilly's estate. Miss Lilly hated when Ryan was late. On Saturday's they had two hours together. With Mike gone for the summer, the only person they had to worry about was Gus—he was Miss Lilly's boyfriend of four years. As soon as the divorce was settled, Gus moved promptly into the estate. He was a car mechanic at the local Lube Right. Everyone suspected that he and Miss Lilly were having an affair long before she caught Mayor Lilly with Bianca. In fact, Ryan knew it. His own parents were divorced and being the only boy in the house with his mother and sister, Ryan found comfort hanging around with Mike…
He spent many weekends and nights at the Lilly's house. On occasion, he and Mike would hear the sounds of passionate sex emanating from the Lilly's master bedroom—only Mr. Lilly was away on business. This happened on multiple occasions. At first, Ryan and Mike would huddle outside of the master bedroom door—giggling and snickering at the sounds. Once, Gus even whipped open the door and chased them away. Later they figured out that the sounds traveled through the vents and that they could hear every amorous detail from the hallway bathroom. From there they could lock the door and listen at will. But as they grew older, their snickers were replaced with absolute silence as they both wanted to hear every grunt, every moan, every slap, every thrust. Their hard-ons would tent their boxers—they would both go to bed and masturbate under the sheets. Eventually, they began jacking openly in the bathroom as they listened—a bold move that Ryan started when he just couldn't take the strain of his erection or wait until he got under the sheets. They would pump furiously while Gus nailed Mike's Mom. Sometimes he'd fuck her for hours and both of them would spurt load after load of cum all over themselves. This lead to shooting cum on each other, and over time they would stroke each other—timing their ejaculations with Miss Lilly's orgasm. She would wail so loud, it's a wonder the whole town couldn't hear…
Ryan pedaled hard as his bike kicked up dirt. In the time since he graduated high school, Ryan had grown into a strong young man—four inches taller and twenty pounds heavier—all muscle. His high school years seemed like a distant past, yet he felt like a high school kid today…
It was during his senior year that he began the turgid affair with Miss Lilly—or Madison as she liked Ryan to call her when they were alone. It was at Mike's college going away party that Ryan had his first sexual encounter with his best friend's mom. She was drunk and so was Ryan. He found himself gazing at her incredible cleavage—38DD's to be precise. That size rack on such a thin frame is what made Miss Lilly standout. When she caught Ryan's gaze she took him by the hand and led him to the upstairs of her home. They walked past busy partygoers—no one seemed to pay any attention to the two as they ascended the long spiral staircase. Ryan remembers it vividly because he was terrified that Mike would see—that Gus would find them together as they fucked in the master bathroom. Gus was a massive man—6'5" tall with hands the size of catcher's mitts. Ryan shuddered at the thought of the ass kicking Gus would deliver if he caught him. How he managed to shut out his fear and fuck Miss Lilly, Ryan will never know—but he remembers how his cock began thickening as they walked up the staircase. He remembers how the anticipation of laying Mike's mom—the woman he fantasized about along with her own son—made his cock harder than it had ever been. And fuck her he did—with wild abandon for what seemed like hours. They fucked and fucked and then fucked some more. Totally losing track of time—at some point during that evening he passed out…
Ryan coasted down a steep hill leading directly to the double wrought iron gates of the Lilly estate. They were wide open. He liked to think that she left them open for him, but the truth was that they were left open on Saturday mornings for the landscapers. He cruised past them as they went about trimming bushes and mowing the lawn. Antonio, the head landscaper waved at Ryan as he passed. He parked his bike in the rear of the house to make sure it wasn't out in the open. He could feel his cock, semi erect and drooling in his pants in anticipation of Miss Lilly's attention. She typically had Ryan enter through the back door and to the second floor via the rear staircase, which lead upstairs from the kitchen. He had seen her twice this summer since returning from college and on both occasions, he found her waiting on her massive Victorian bed—dressed in silk and lace. The guilt Ryan felt from having a sexual affair with his best friend's mom was not easy to live with. There was awkwardness between Ryan and Mike—but it started well before his affair with Miss Lilly…
Years ago, there was a period when Ryan and Mike stopped talking to each other. Ryan was spending a weekend at Mike's house as usual—this time for the 4
th
of July weekend celebration. As the two boys grew older, their spying habit on Miss Lilly ended—together at least. Ryan continued sneaking out of bed late at night and into the guest bathroom for solo jack-off sessions while Mike slept. He couldn't resist the erotic sounds of Miss Lilly and Gus. He even went so far on one occasion as to sneak a peek through their bedroom door. That was the first time he saw her naked, riding Gus hard—her glorious tits bobbing up and down with each thrust. He jacked hard that evening and boldly shot a load all over the wall outside of the master bedroom. But, on a later occasion he woke up quietly and snuck out of Mike's room—as usual he headed straight to the guest bathroom, closed and locked the door, pulled his shorts down, and waited. Eventually he could hear the muffled voices and then the sounds of Miss Lilly's bedsprings—their rhythmic squeaking announced the beginning of the lovemaking. That night the bedsprings sounded especially spastic and the headboard was banging against the wall extra hard.
Whoa
—Ryan remembers thinking to himself as he pumped his cock—
Gus was really giving it to Miss Lilly good!
BANG! SQUEAK! BANG! SQUEAK! The intense sound of the action goaded Ryan into sneaking a peek once again—so he quietly snuck out of the guest bathroom, hard dick poking out of the waistband of his boxers, bobbing up and down as he tiptoed down the hall. But this time as he slowly turned the knob of Miss Lilly's master bedroom door, nothing could prepare him for the sight he was about to see. If he could just go back in time to that evening and never open that door, he would save himself years of emotional turmoil…
Ryan walked up the kitchen staircase to the second floor and slowly approached Miss Lilly's master bedroom—the door left slightly open. He thought back again to that night so many years ago—the one he wishes he could take back on that 4
th
of July weekend when he approached this very same door…
Back then he was flooded with the thrill of watching Miss Lilly and Gus going at it. What he found instead would change his relationship with Mike forever. There was Gus, pounding his hips up and down—bedsprings squeaking, headboard banging. Only it wasn't Miss Lilly on her back with her legs spread wide—It was Mike! Ryan remembers being frozen while he gawked at the unbelievable site. As he watched, he began to notice so much more than just the act of sex taking place. He saw the pleasured smile on Gus and heard the wet sloshing sounds of his cock sliding in and out of Mike's ass. He heard Mike's muted grunts and saw the look of extreme pain on his contorted face. For the first time he noticed the size of Gus's balls—they were like large lemons flopping back and forth and mashing hard against Mike's rear. Both of them were soaking wet with sweat…
Ryan paused at Miss Lilly's master bedroom door as he played back the events of that disturbing summer night. This was the exact spot where he watched Gus pull his long cock out of Mike…
Ryan remembered watching his best friend roll over onto his stomach, trying to crawl away, pulling at the wet bed sheets. Gus's cock strained as it stood proudly in the air, wet and dripping. Before Mike got very far, Gus gripped his ass cheeks with his massive hands, each one cupping a fleshy globe, and pulled him back. The look of fear on Mike's face was terrifying to Ryan—
was Gus raping Mike? Should he call for help? Should he try to stop him?
