Sissyboy Gets His Man

By

Jimmy Smith

From the Prologue: Daddy's First Sissyboy:

               When Matt returned to the present, he looked at the clock on the wall and knew that he had let time get away from him. He knew that if he moved along now there would still be enough time to get Dieter dressed and out the door on his way home before Jason got home from soccer practice. He patted the head of the blonde boy kneeling between his legs, bobbing up and down on his shaft. Dieter knew the signal and stood to his feet. He took up position on his back on top of the big desk in the den and raised his white stocking clad legs into the air, revealing his well used boycunt. Dieter had grown a lot in the past three years, his legs especially. They had become long, and coltish, a lot like the legs of a tween boy but Matt wasn't complaining as they were now long enough to wrap around his waist or long enough that the boy's feet reached his shoulders. Either way, he loved the feeling of Dieter's stiletto clad feet against his skin.

               He slathered Spermbutt on his rampaging cock and pushed forward until it was all in and Dieter was stuffed with thirteen inches of mancock. It had taken Matt a year to bring the boy to the place where Matt could enter him fully, achieving the milestone on the boy's sixth birthday. Watching the clock closely he pounded Dieter at a fast pace so they were finished, dressed and Dieter well on his way home ten minutes before Jason walked in the door. As he greeted his son, who looked so much like him, he thought of the Try Boys/Men ads and chuckled to himself, unaware of how those same ads would disrupt the domestic tranquility of their home beginning with supper that night.

Chapter One:

Jason's Loss of Innocence

               "NO! ABSOLUTELY NOT!" Matt Spermer thundered at his nine-year-old son Jason for the first time in the boy's life. "NO WAY! NO HOW! NOT GONNA HAPPEN! AND DON'T YOU DARE EVEN MENTION IT EVER AGAIN!"

               "WHY NOT?" Jason shouted back. "THAT'S SO NOT FAIR! I KNOW OTHER BOYS IN MY CLASS THAT ARE TRYING THEIR DADDIES AND THERE DADDIES ARE TRYING THEM TOO! SO WHY CAN'T WE TRY ONE ANOTHER?"

               Matt calmed down slightly as the shock of his son's request made so casually over dinner was wearing off. When he spoke again it was in a normal voice. "Because it is just plain wrong, son."

               "Why is it wrong?" Jason pressed.

               "Three reasons," Matt said. "Number one, it would be gay because you're a male as well and being gay is wrong. Two, you're just a minor, so it would be child abuse. And three, because you're my son and incest is even more wrong that being gay." He knew he was being a hypocrite of the highest order as well as lying to his son. But wasn't his whole relationship with Dieter lying to his son? But that was the problem. In Matt's mind, to have sex with Jason would mean being unfaithful to Dieter. Never mind that he "cheated" on Dieter two or three times a day at the stadium and practice facility, where he had taken to banging the shit out of the ballboys, who conveniently enough all about twelve-years-old. But the truth that Matt was really unwilling to admit, even to himself is that, in his mind, Jason just didn't compare to Dieter in any way. And so Matt Spermer continued to lie to his son.

               Jason was crushed by his father's words and he burst from the table, tears flooding his eyes. He ran out of the dining room and was quickly out the door and on his way to Dieter's house. Matt was sorry that he had hurt Jason, but then that stiff cock thing took over again and he decided to give Dieter a call to come over again. It was risky because he didn't know when Jason might be home but by that time his cock was totally in charge. He called Dieter's number and the boy eagerly agreed to the plan for a further good stiff fucking that day.

               Dieter quickly donned a pair of jeans to cover the white stockings he still wore from his afternoon tryst with Matt. He slid on his Nikes and placed his heels in the usual bag. He had just walked out his door when Jason was walking up the drive and greeted him. Dieter was at a loss of what to do. He could tell that Jason was upset and a small part of him thought he should stand Matt up and try to comfort Jason, but that part wasn't the one controlling him at that moment. While Matt was thinking with his penis, Dieter was thinking with his rectum which itched with an itch that only Matt's thirteen inches could scratch. So Dieter came up with some excuse and hurried away. Jason was crushed for a second time at the knowledge that even his best friend didn't want him around right then: that something else was more important than Jason.

               At that point, Jason was too hurt and angry to go home, so he decided to take a wander over to the school yard and see what was going on there. He was surprised to see that the school doors were still open and so he walked in and was surprised that it seemed as if no one was around, so he decided to explore a little bit. It was as he was approaching the door to the janitor's office that he heard the first signs of life.  The sounds coming from the office were ones that Jason had heard with increasing frequency since the first appearance of the Try Boys and Try Men ads. Most of the boys in the school were eager to try men and most of them decided that the African-American janitor was a prime candidate if the boy didn't have a father or the father was like Jason's dad(if the boy only knew). Jason wondered what boy was having his pussy pounded by the man at that moment. So he looked in the office and was shocked then dismayed to find Mr. Creampie just pummelling the chubby ass of Erik Blimpmen, the fattest boy in school. 

               Jason's spirits sank even lower. It just wasn't fuckin fair, he thought. He couldn't understand how even that fatass was able to try a man and he wasn't. He wanted to run away but couldn't move his feet. So he watched the first real life example of what he wanted to have happen to him. When the man and Erik had finished and Alex Creampie saw who it was that was standing there, he was ecstatic! He'd been wanting a shot at the Spermer boy for a long time but never expected he'd ever see the boy in his office. He had asked the boy's best friend, the von Squiggler boy, who he was regularly banging along with the boy's father, brother and Matt Spermer, what his chances were with Jason. Dieter shook his head and said, likely not good, that Jason was totally clueless about what men and boys could do together for pleasure. Alex had put it out of his mind and had forgotten it, until he was faced by the boy that fateful evening.

               Jason remained silent and just looked the man over until fat Erik had left. He was amazed by the black man's body, especially his penis, which looked slightly smaller than his daddy's but not much. It was still erect and was slick and shiny with his cum, Spermbutt and Erik's rectal juices. Jason's mind was torn. On one hand he wanted to give himself to this man to be loved and then fucked by that big cock but he was also afraid. And he was also hurt again by the knowledge that for this man he would be only one of many boys.

               Alex's thoughts began planning how to get the boy out of his pants but then he noticed that the boy looked upset. He handed Jason a Kleenex and as Jason blew his nose, Alex slid into his boxer briefs again he asked the boy what was on his mind and before Jason knew what he was doing he poured out the whole story to the large black man, whose thoughts amounted to Oh shit, the poor kid. Alex felt sorry for the kid because he had no clue what was going on and because it seemed Matt Spermer was being such a liar and a hypocrite. He wasn't dumb and knew that Matt had made Jason join the school soccer team because it would give him more opportunities to fuck Dieter von Squiggler.  Then his lust started thinking for him again and he decided to see where things might lead.

               "Well Jason," he said softly. "If you really want to try a man, I'm a man."

               "Yes you are, Mr. Creampie," Jason said. "But right now I'm so upset I don't think I'm ready for that."

               "That's fine Jason," Alex said. "When you are ready, you just come down here either at lunch or after school and let me know."

               "How will I let you know?" Jason asked.

               Creampie stood up and went over to his closet. He opened it up and pulled out a pair of black stocking and garter belt. He put them in a special bag with a pair of heels and returned to hand them to Jason. Jason emptied out the contents and nodded to the janitor. He knew that the stockings and heels were kind of the uniform of the local sissyboys, but he had never heard that it was because that was what Dieter von Squiggler had been wearing when he had seduced Matt Spermer.

               Jason said thanks to the man for listening to him and left to go home.

               Speaking of Dieter von Squiggler, he was once again enjoying the fruits of that seduction. He was on his hands and knees wearing his usual outfit, head down and butt up just like a little bitch puppy as his man was squatting behind him and driving his cock into the boy at a pace he had never used before. The whole night had been like that. Dieter had arrived intending to tell Matt about Jason coming to talk to him, but he didn't have a chance as Matt was already naked when he arrived and attacked the boy the minute he walked through the door. He just about tore the boy's jeans and shirt off and carried him into the den and tossed him on the couch on his back and before Dieter could say a word, he was filled once more by Matt's boyrammer. So Dieter never had a chance to tell Matt about Jason.

               Too bad.

               Matt had pounded Dieter mercilessly form the minute he hit bottom and was in full on beast mode. Dieter had never seen his man like that before right from the beginning. Not that he was complaining, he was receiving the assramming that every sissyboy dreams of. That one lasted a frantic fifteen minutes, three orgasms for the boy and one creamy explosion from the man. Then came the next surprise. Matt usually needed a rest after each fuck. Not that night. He pulled out and ordered the boy to assume the position and after getting behind him, drove his cock back into the boys and kept rutting away. We join them at the twenty minute mark of the second fuck. Matt continued to plow Dieter's ass for another frantic five minutes before he filled him with load number two. It was then that Matt made the decision that would change multiple lives, including his and Dieter's. Had he quit then and let Dieter go home, certain events would not have occurred that would trigger other events.

               But as stated before, Matt Spermer was in full fledged beast mode and accordingly his penis was in charge. He once again pulled out of Dieter, turned him on his back again, slammed balls deep once more, then grasped the boy's waist and got to his feet. He walked over to the couch. Dieter started trying to say that they should stop, but the motion of Matt walking with his cock in Dieter's ass had changed the angle that his cock was touching Dieter's boy's place. By the time Matt lowered them to the couch so that Dieter remained on top, Dieter was far beyond protesting. He immediately began bouncing up and down in Matt's lap like a bucking bronco.

               Jason Arrived home and was surprised that his dad wasn't there watching TV and to ask him where he'd been, or what was in the bag. Jason figured that since he couldn't see his dad in the living room, then he must be doing something in his den. Jason headed for the part of the house where the den was. Jason heard strange sounds coming from the den as he approached. He knew they were sex noises and he assumed that his dad had some lady over for the first time in a long time. He started to walk away then decided to get closer so he could hear better. As he approached the door, he could hear the muffled voice of the other person mixed with his daddy's grunts and growls and he received shock number one. It was a BOY in there with his daddy! Jason's hurt came back at the thought that it wasn't all boys that daddy didn't want to fuck, it was just Jason he didn't want to fuck. He considered walking away and if he had, a great many things would have been different.

               Choices and consequences will bite you in the ass every time.

               Jason decided that he wanted to, had to know who it was that had seemingly taken his daddy away from him like that. And in so doing, as he gripped the door handle to slowly turn it so he could look in, he received shock number two and it was a doozy.

               "OH MATT, FUCK ME MATT!!!! FUCK ME YOU STUD, YOU SEXY BEAST!!" a familiar voice rang in ecstasy from behind the door.

               DEITER! IT WAS DIETER DADDY IS FUCKING! Jason thought. At first he couldn't believe that his supposedly heterosexual and homophobic father was in the process of fucking his equally supposedly heterosexual and homophobic best friend. He prayed he was dreaming. The next sounds crushed that hope like a raw egg.

               "FUCK... OH YEAH... OOHH.... FUCK...FUCK YEAH FUCK... MEE!" was Dieter's next exclamation, followed closely by: "OH FUCK YEAH! FUCK! FUCK! FUCK! FUCK!

               At that point the anger kicked in. Apparently, there was a third "h" word that applied to both daddy and Dieter: hypocritical. That very night at supper, hadn't daddy said for the umpteenth time that gay was wrong? And he also remembered Dieter's reaction when he mentioned Try Boys or Try Men. Dieter as well had expressed disgust with the notion of doing anything with even another boy, much less a "dirty old man". But here he was standing outside the door as Dieter screamed and pleaded for Daddy to do to him the gayest thing that a man and boy could do together. He wanted to run away at first, but then he decided that he needed to see it, needed to watch the two deceitful hypocrites fuck.

               He pushed the door open quietly but it really wouldn't have mattered if there had been a noise. The two people he cared about most in the world were so engrossed in their sex that they were oblivious to his presence. He watched until his daddy cried out that he was gonna breed Dieter's boy pussy and Dieter cried out that he was cumming too. Jason took that opportunity to rush from the room, making sure the door was closed quietly. He ran out the door and hid in the bushes until Dieter had walked out the door and was out of sight. But he did have to resist the urge to rip Dieter's daddy stealing head off as he stood there brazenly kissing Jason's daddy with tongue.

               As soon as Dieter had been gone for about five minutes, Jason stood up brushed his shorts off and walked into the house. "Daddy, I'm home," he announced, not surprised to see that the lying sack of shit sitting in the living room pretending that he had been there all night.

               Matt kinda grunted at Jason, not really caring that he was home as he still was really trying to recover his faculties from his session with his sissyboy. He merely grunted again as Jason said he was going to go and shower before going to bed.

               Jason went upstairs and quickly entered his room. He shucked out of his clothes and padded naked into his ensuite bathroom. He got into the shower and allowed the warmth to relieve his tension and he began to think. He wasn't going to get anywhere with daddy, daddy was too much into Dieter. And he also wisely decided that he would only bring himself trouble by attacking Dieter, so he decided to leave him alone, but he intended to tell his former friend a few things if he got a chance. The problem he now faced was the fact that he was even more determined to become a man's sissyboy. He briefly considered Mr. Creampie, but even though it was likely that the black man was going to be the one bring into his sissyhood, the man was not a long-term option. Jason wanted to belong to one man like Dieter belonged to his daddy(if he only knew the truth about both daddy and Dieter).

               He got out of the shower still ruminating his options then he got an idea. Jason had a secret that daddy didn't know. Jason knew and his "Uncle" Amos and "cousin" Jared. He'd figured it out after the ads came out and he viewed the website. The next time he saw them together, he saw all the signs, especially them making googly eyes at each other when they thought no one was looking. Not that anyone really cared now since Sissyboy magazine was first released. He decided to confide in Uncle Amos.

               He returned to the bedroom area and logged into his computer. He found Uncle Amos on MSN and asked if he could come over and talk to him tomorrow afternoon. Amos hesitated and asked what Jason wanted to talk about, saying that they could turn on their encryption. Jason agreed and then, told the man the whole story of his daddy's and Dieter's lies, deceit, hypocrisy and betrayal. He then also expressed his desire to be a man's sissyboy.

               Amos then had a great idea. His hesitation at allowing Jason to visit the next day was the fact that one of the Wide Receivers from the team, David Coxman was coming over so Amos could give him the same basic talk as he'd had with Matt three years before. The difference was that Matt had never been with a boy before, whereas David had, he just didn't think anyone knew about it, but everyone really did. It was so blatantly obvious what was happening when David would be seen walking off with a ball boy at training camp and practices and then return a half hour later with the boy, who always seemed to be walking a little bowlegged. Amos decided to try and hook up David and Jason. He quickly told Jason to come there right after school and the boy agreed before logging off. Amos began talking to Jared and they formulated a plan worthy of cupid.

               After Jason logged off, he went to the Try Boys/Men Website and surfed a bit. He went the section he had avoided before: the section of sissyboys in lingerie. He had to admit that the boys in the pictures wearing the stockings and heels were the hottest. And he had to admit despite his anger that Dieter had looked mad hot in his. He logged off the computer and looked over at the bag that Mr. Creampie had given him. He stood up and walked to it and opened it. He realized that he had no real idea how to put the stockings and garter belt on so he logged back in and found a spot on the site that explained what to do. So Jason followed the instructions to the letter and within minutes his boyish legs were encased in the silk stockings. He sat down on the edge of his bed and slipped into the heels then he stood up. He had a little trouble getting his balance and walking on them but he persevered and hoped that he wouldn't have to do too much walking in them. Finally he went and stood in front of the mirror. He thought he looked sexy as fuck in them and knew for sure that Mr. Creampie was in for a surprise the next day at lunch.

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