Sissyboy Prequels and Sequels


Author's Note: This story is a prequel to the events of Beautiful Creamer's Secret Sissyboys 1 as well as my own story Riley's revenge. It is designed to flesh out the beginnings of the relationship between Riley's father and best friend.


Vince and Benny


"I can't believe I'm actually doing this," thought eleven-year-old Ben Watkins, Jr. as he peddled his bike wildly. His intended destination was the house of his best friend, Riley Sugarbum. But he wasn't riding there to see Riley, no, he was going there for a different purpose, one he'd finally decided on the minute he'd heard Riley say that his mam was taking him and his sister's shopping: He was going to seduce Riley's father, Vince Sugarbum.




To all the world, Benny Watkins seemed to be your typical, jockish, heterosexual preteen boy. And he had been, until the strange feelings had started six months before: Strange thoughts of sex with other boys and with men. Thoughts of sucking cocks and taking them up his little bottom. But that was gay, wasn't it. The Reverend Crushlove sure thought so. He preached that every Sunday, especially how being gay was the worst thing a boy could be. Benny believed it, but that didn't stop the thoughts and feelings from coming. So Benny did what any other red-blooded straight boy would do in his place. He verbally attacked anything that even hinted of anything but hyper masculinity. And there was no person that he was harder on than his best friend Riley. If Benny had been asked to stand up in class and point out any gay kids in his class, Riley would have been one of the first. And Benny was quick to condemn anything in Riley that demonstrated that he was right.

But things really changed for Benny four months before. He would NEVER forget finding that comic book on his school bag, the one that had just about singed his eyebrows and eyelashes and scorched his eyesballs. It was about a boy named Peter, a boy his age, and how he had sex with first a man he had a "date". Benny knew he show throw it into the trash and run to the Pastor and confess the sin of even opening some smut. A boy dating a man and letting him do such gay things to him. Every part of Benny was offended by the very idea. Except his little penis.

His penis wasn't offended at all. It thought such an idea was one of the best it had ever heard. It was standing up straight and stiff and Benny yielded all his thought processes to it. So like any normal boy of eleven would, he did as his penis wanted and kept reading. Well, he did stop long enough to strip out of his school clothes which was a good thing for just as his wide-staring eyes were looking at the man sliding his manly large cock in and out of Peter's well used bottomhole, Benny Watkins fired his first ever load of boys cream onto his belly.

Oh my.

So every waking moment that he wasn't in school or otherwise engaged, Benny returned to the sexual adventures of Peter. He lost count of how many times he had spewed his creamy juices on his belly reading it, especially the part at the end of the comic where Peter also has sex with his own daddy! Benny didn't think that was quite normal, ignoring the fact that he had his greatest orgasms when reading that part. He decided that he would never do those dirty things with his own daddy. Well, not that he would be doing those things with any man, he quickly told himself. And yet, it was out of curiosity while he was reading the part where Peter and his daddy are fucking like a couple of bunnies that he slid one spit soaked finger into his bum and found he quite liked it.

And then he had discovered the next special thing in his pack. The Shower Buddy adorned the package in large letters and underneath that, in smaller letters it added, "A Boy's First Best Friend". It had been pure curiosity that had made him open the package to discover the suction cup base and the three phallic attachments in small, medium and Oooh-la-la. Just as it was when he attached the suction cup to the wall of the shower at the right height, screwed on the small attachment, coated it with Vaseline, bent over and pushed his weight back so that the toy slid into his bum and then rock back and forth as the instructions said. It was the same curiosity that caused him to go to the medium size after about three days, and then the "Oooh-la-la" two days after that.

But deep inside he must have known that it wasn't just curiosity because his homophobia became more strident and militant, especially with Riley. Benny was playing a desperate game to both keep himself in denial about being gay and keeping others from even considering that he might be. But he didn't let it stop him from riding the Shower Buddy to multiple orgasms. Sometimes for a change, he would secure the sex aid to the floor and sit on it, bouncing up and down so the fake penis slid in and out of his ass until he exploded.

But on the day he received the final surprise in his pack it nearly made him pack in the whole thing. He couldn't believe that he found two pairs of panties: hot pink and red. The note asked him to signify wanting to learn more by wearing one pair to school the next day. No, no, Benny convinced himself. There was no way he was wearing panties to school. But once again his penis thought it was a great idea, getting all stiff and drippy. However, he decided to do something that would take his mind off it. He had an idea. His basketball coach from the local Y, Mr. Cheevers, lived a couple of blocks away. The man had often said that any of the team were welcome to come by anytime to shoot some hoops with him. So, for the first time in his life, he decided to take the coach up on his offer. He pedaled over there and was shocked by the fact that, although there was a bike on the lawn that Benny knew belonged to DeVon, there was no signed of the nine-year-old or Mr. Cheevers.

He dropped his bike and started to look for them. He was looking around the backyard and was just about to give up when he started to hear sounds coming from the small utility shed. He heard deep, guttural moans and high-pitched gasps. He also heard creaking noises like the seats in his dad's car made when you bounced on them. He quietly approached the window and his life was forever changed. In the dim light of the shed, he could make out an old car seat on the floor. On it were Cheevers and DeVon. Both man and boy were naked, except the small black boy was wearing white sweat socks with blue and red bands around the top of them. The boy was sitting in the man's lap, bouncing up and down. Benny could see the white man's massive cock sliding easily in and out of DeVon's asshole. Benny could hear that DeVon was enjoying the whole thing, but Benny was still disturbed by what he saw. Seeing a big-cocked man fucking a boy in a comic was one thing, but seeing it in reality can be a bit overwhelming, so Benny got the hell out of there. But seeing it seemed to confirm something in Benny's mind and so, as his friend Riley would do months later, Benny wore the pink panties to school.

Benny was scared as he was ordered to the Principal's office during his first class of the day. But then he received the shock of all shocks, when Mr. Sternrule asked him which of the panties he had worn that day. Benny wasn't the smartest kid in the school, but he was smart enough to realize that Mr. Sternrule had been the one who had left those special gifts in his school bag. Starting with that first short session, the man took Benny through the process of learning the many ways a boy can please a man, a process that led inexorably to the moment three and a half months later when Benny finally let the man stuff his big, manly cock into his virgin bottomhole. The man had been patient, understanding that for boys like Benny, letting a man stick his cock up your shitter is a whole other level from fucking oneself on a vibrating, plastic cock in the shower. And so he just kept up his fingering of the boy and the massaging of his prostate, until one day, before Benny even knew the words were going to come out of his mouth he screamed:

"For God's sake, Sir, will you stop fooling around and just stick it in me?!"

"What was that Benny?"

"I said, FUCK ME! FUCK ME NOW AND FUCK ME HARD!" Benny cried.

So the Principal did just that, for thirty-five exquisite minutes. And as Benny pedalled home afterward, he knew that he definitely wanted to be fucked again. And he was, by his Principal and by a few men the man knew. The Principal was okay, after all he had relieved Benny of his troublesome virginity, but the other men left him cold because it seemed to be only about them getting their cocks up his ass and cumming. Benny was looking for a man that he could be with for a long time and he thought he had the perfect candidate: Vince Sugarbum, his best friend's father.

The man always seemed to take more of an interest in him than Riley, his own son. Over the years, it seemed to Benny that Mr. Sugarbum was always looking at him and Riley strangely. Now Benny understood that look: the man wanted to fuck them, or at least Benny, and had for a long time. Benny started to feel sorry for the man as he always seemed to look so achey and needy. Benny got angry with Riley for not taking care of his daddy's needs. He had no idea that Riley had not yet been given the training that he had, the mysterious gifts had never shown up in his school pack. Benny assumed that the Principal had seduced all the pretty boys before turning to boys like him. So Benny decided that if Riley wouldn't give Mr. Sugarbum what he needed, he would. The only problem was when to make it happen. Then Riley had complained one day at school that his mom was dragging him shopping with her and his sisters.




And so that was how Benny Watkins ended up wearing his most sexily jockish outfit and pedalling like a mad man towards his best friend's house to seduce his father. He pulled up and dropped his bike on the sidewalk. He was careful to make sure that no part of his bike touched the lawn. Mr. Sugarbum had yelled at him before because of that and Benny wanted things so that the only shouting that Vince Sugarbum would be doing is shouting Benny's name as he pumped loads of gooey mansperm up Benny's ass. He took one more deep breath and plunged ahead with his plan. He found Vince in the backyard doing some gardening.

"Hey Benny," Vince Sugarbum smiled and said as he saw the boy approach. "Riley's not here, he's shopping."

"I'm not here to see Riley, Mr. Sugarbum," Benny said. "I'm here to see you."

"And why's that, Benny?"

"Well, Mr. Sugarbum, I know what you want more than anything in the world, and I'm here to give it to you," Benny said.

"Say that again," Vince said, his eyes narrowing.

"Did I mumble or something, sir," Benny said. "I said I know what you want and I'm here to let you have it."

"What are you talking about, Benny?" Vince said.

"Oh come on sir," Benny said. "You really think that I don't see how you look at me, especially when I've been swimming? You really think that I don't know that you've been looking at my ass since I was five years old? And you think that I don't know that you're thinking about how badly you wanna fuck me?" Benny then took a chance and turned from the man and mooned him, even spreading his cheeks apart to show his boypussy. "You think I don't know you want to fuck this hot little ass?"

He half expected to hear the man's angry voice telling him to pull his pants up and get lost. But he didn't. For about five minutes, there was silence, then the man spoke:

"In the fucking shed, now!"

Benny didn't pull his shorts up because he knew what was going to happen in that shed. He walked in the door and looked the situation over. The only place that he could see where they could possibly fuck was the top of the plywood work bench. He heard the man enter and shut the door. Vince Sugarbum swept everything off the top of the bench and covered it with a blanket he kept in the shed for when Riley got cool during the evenings they spent outside.

"Strip down to just your socks and shoes and get on the bench, on your back," Vince ordered.

Benny obeyed because this was exactly what he had wished to happen, other than the setting, of course.

Vince stripped himself and opened a box. He pulled out a jar of Vaseline. "I keep this out here for lube when I need to jerk off while you and Riley are here in your bathing suits, but it's mostly you that makes me horny. You have no idea how much cum I have spilled in this shed thinking of burying this up your sexy ass." He brandished his penis at Benny for the first time.

Benny gasped at its size and began to have second thoughts. It was so big! He studied it with uncertainty in his eyes.

"Big ain't it?" Vince said. "Don't worry, Benny, your ass will be getting to know it soon enough." He paused then grinned salaciously. "What's that, Benny? You're a little less certain of yourself now that you see what I have for you? You should have thought of that before you showed me your little pussy outside. Besides, I bet if I offered this to Riley, that little creampuff would be all over it."

That last jibe overrode any hesitation Benny may have had. "Just shut up and stick it in me!" he growled.

Vince smiled lustfully. "I thought you might say that."

He coated his cock with the oily substance and also rubbed some on the boy's pussy. He placed the boy's feet on his manly shoulders and stuffed his plum-like cockhead into Benny's boypussy. The boy grunted at the intrusion, Vince Sugarbum was much bigger than Mr. Sternrule but did not ask the man to stop. The grunt became a series of little gasps and whimpers as the big cock continued to burrow its way into him until Benny could feel the man's wiry pubic hair against the bare skin of his buttcheeks and the huge glans deeper inside his guts than his Principal had ever gotten.

"He's so fuckin big!" Benny said, his voice quavering with the strain. "But he feels so fuckin good! Fuck me Mr. Sugarbum! Fuck me hard!"

With that encouragement, Vince Sugarbum began to fuck, his hips moving his massive cock in and out of the willing boy, something he had not done since he graduated college and got married. He loved his wife but within the first ten thrusts into Benny's moist, warm tightness, he was reminded that there is nothing like plowing a hot boypussy. He was suddenly overtaken by an urge that he had not felt since his last boy so many years before. He sped up, forgetting the fact that the boy beneath him was only eleven-years-old and began fucking him hardcore, the way he remembered that little sissyboy sluts wanted and needed to be fucked.

Benny Watkins was in heaven. With Mr. Sternrule he had found himself just laying there still as the man's cock stabbed into him. But with his best friend's father in that shed, Benny felt himself feeling things he had never felt before. With the Principal, he had continued to tell himself that he was still a straight boy while sucking cock and taking it in the ass was just another way for a boy to get off. But from the very first thrust of Vince's cock, Benny knew that the truth was that he was a cock-craving faggot slut. With that realization, instincts known only to sissyboys rose up inside him and he was finally free to go with them. He found his hips moving upward to meet every one of his man's deep, hard thrusts. He wrapped his hands around the man's neck and pulled his face up to where he could kiss the man's lips and suck on his tongue.

When he let himself down, he could no longer stay the cry, "YES, VINCE SIR! FUCK ME! FUCK ME HARD AND BREED MY SISSY ASS!"

"Like I wasn't going to anyway," Vince said sarcastically.

He looked over at the clock on the wall and realized that he still had two hours before the boy would have to be dressed again and leaving. He placed his hands beneath the boy's back and lifted him off the bench. He stepped back ward and turned toward the door. He walked out of the shed into the backyard. He blessed the bylaws that said that he had to have such a high privacy fence because of the pool. He wondered what his neighbours' reaction would be to the sight of him walking through his yard naked, holding a naked boy impaled on his cock. The walking motion changed the rate and speed at which his cock rubbed Benny's boy's place and the boy stiffened and came around Vince's cock before Vince got him inside. Vince took him up to his bedroom and the bed that Benny would feel beneath him so often over the next month and a half.

Vince and Benny fucked wetly and noisily for the next two hours before Vince finally deposited his third load of cum in Benny's well fucked ass. As they walked naked back to the shed, they started talking about how they could arrange to get together as often as they could. Vince stated emphatically that Benny was NOT to mention their relationship to Riley. Benny said he wouldn't, as long as Vince kept it a secret from his father. Vince agreed. They both dressed and Benny left after one last kiss.

Their get togethers were limited at first, until Vince heard the announcement that the choir required new singers, especially boys. Vince volunteered Riley for a spot and the next night he quickly ushered his son out of the house just before six, when Benny was supposed to arrive. Benny and Vince fucked wonderfully for the hour and a half they had before Riley was due home, not knowing that they briefly had an audience.