Sissyboy Gets His Man



Jimmy Smith


From Chapter One:


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.


Chapter Two:

Jason Meets His Destiny

When Jason woke up the next morning, he thought at first that the events of the previous night were just a dream, until he looked over and saw the bag that Mr. Creampie had given him and everything came flooding back to him, especially the sight of his daddy and Dieter fucking. Jason found it very difficult to act normally, but he knew he must. He considered putting on the stockings with long pants the way his so called best friend did, but he decided that would be too quick of a change and his daddy would be sure to ask questions. Or so he thought as he stuffed the smaller bag into his backpack.

In actual fact, it wouldn't have mattered if he had. Matt didn't even acknowledge Jason when he came to the table, his mind still preoccupied by the session he'd had with Dieter the night before. He had never felt that way before. He had felt like an animal and the harder he'd fucked Dieter, the louder Dieter begged and pleaded for more. Matt was coming to the place where he hated seeing Dieter leave and wanted him around all the time. He looked over and saw Jason sitting there eating his breakfast and a small amount of hatred stole into his mind. He started considering doing Dieter openly and the little shit could deal with it, not knowing that the little shit already knew and was going to deal with it, but not likely in a way that Matt would like.

For his part, it took all Jason's willpower to keep from getting up and slapping his dad in his lying, hypocritical face. He had no doubt that his dad's ignoring of him was caused by him thinking about that Benedict Arnold, Dieter. Jason knew it would take all his willpower to keep from attacking his former best friend at school, but he knew he had no choice. Jason walked out the door and walked to his rendezvous with Dieter. As Jason approached his backstabbing, soon-to-be former best friend, he felt all the betrayal and anger well up inside him and he couldn't trust himself to say anything except to grunt "hi". The walk to school was unusually quiet as the two boys were lost in their thoughts. Ironically though, both boys were thinking about the same event from the night before, but were, obviously having different thoughts about it.

We know Jason's thoughts. But Dieter's thoughts were also consumed by the night before. He was still enthralled by the absolutely mauling Matt had laid on his ass. Matt hadn't been human, he'd been an animal, and that didn't bother Dieter at all. In fact, he hoped there would be many repeats. It had been all he could do to walk home, yet by the time he had gotten home; he heard that his brother was receiving a similar ass-mauling from their daddy. That reawakened his lust despite the ache in his anus. He felt suddenly empty. He ran to his room and retrieved a box from beneath his bed. It contained his best friend in the world, except for Matt. It had been a special present from Matt when he'd turned seven. It was a dildo that had been cast in the image of Matt's big, wonderful cock.

Dieter tore his clothes off and ran into his bathroom. He turned on the shower and when it was the right temperature, he put the dildo's suction cup under it then placed it on the wall at just the right height. He grabbed his bottle of baby oil gel and slicked up his pulsing anus. He stepped into the shower and rapidly impaled himself on the massive dildo and proceeded to fuck himself on it for the next hour and a half, taking himself through a countless number of screaming, dry orgasms. Had his father and brother not been engaged in making loud, sexy noises, they would have clearly heard Dieter's screams of orgasmic pleasure as well as his loud whimpering cries of "FUCK ME, MATT! FUCK ME HARD! YOUR BIG COCK FEELS SO GOOD IN MY ASS!" All in all, it was a very exhausted eight-year-old boy that fell into Dieter's bed.

Dieter came out of his reverie briefly to look over at his unusually quiet best friend. He felt bad about fucking with Jason's dad behind his back, especially since he'd read Jason's journal and saw that Jason wanted his own daddy to fuck him. So Dieter felt kinda guilty about what he was doing. Not guilty enough to stop it, however. The bottom line is that when a sissyboy has a man that can fuck his ass raw the way Matt Spermer could, that tends to cause him to ignore his conscience. Then Dieter remembered that he was also supposed to meet with Mr. Creampie at lunch.

They arrived at cool and Jason was relieved. He made the decision that no matter if it tipped Dieter off that he was pissed off; he would try to avoid Dieter for the rest of the day, made slightly easier by them being in different grades. And then there was him going to see his Uncle Amos after school, so there was really only lunch to have to find a way to avoid Dieter. As soon as they were dismissed for lunch Jason flew downstairs toward the Janitor's room. He ran into the bathroom and changed into his sissyboy outfit. He didn't know that, while he was changing, Dieter was arriving for his lunch time fuck. Jason ducked his head out of the door and looked around to see if anyone was coming down the stairs. Seeing no one, he pulled the door open fully and stepped out into the hall, naked except for the belt, stockings and heels. He walked into the janitor's room and his heart came into his throat.


Dieter and the massive black man were sitting on the bed that the janitor kept in the room for obvious reasons. Dieter was sitting on the man's lap and they were kissing deeply, Dieter looking like he was trying to crawl right into Mr. Creampie's mouth. Jason couldn't believe it! First of all, Dieter stole his daddy, now it seems he had also stolen Mr. Creampie as well. Not this time you little bitch, I'm not coming second this time. With that, his anger flared and the words forced themselves from between his lips.


Dieter sprang from the man's lap and Jason could see that both man and boy were rock hard. Dieter looked into Jason's eyes and seeing the anger there, his first thought was, He knows. And he was suddenly afraid. "I...I...I..." he tried to start saying.

"Shut it," Jason said. "You are the worst backstabbing little weasel I have ever seen. Not only do you steal my daddy, now you seemingly have your hooks into my second choice as well. You're a greedy little slut." He paused. "You can have my daddy, you little shit, it's clear from the lengths that you both went to hide your relationship from me that I have no chance with him," Jason growled. "I know that you're going to be heading to my place after school so daddy can fuck you. I have someplace to go so you have 2 hours or so to do it. You better not be there when I get home."

"How'd you find out," Dieter asked.

"Simple," Jason said. "I came home last night and saw you. Well, I heard you before I saw you." He paused. "OH MATT, FUCK ME MATT!!!! FUCK ME YOU STUD, YOU SEXY BEAST!!" "FUCK... OH YEAH... OOHH.... FUCK...FUCK YEAH FUCK... MEE!" "OH FUCK YEAH! FUCK! FUCK! FUCK! FUCK!" Jason said in imitation of his suddenly embarrassed former friend.

"Here's the deal, Dieter," Jason growled. "We are no longer friends. The final straw is the fact that you abandoned me when I needed to talk to you just because you crave my daddy's cock in your ass. You are going to leave this room as soon as I am done speaking. If you do not, I will bury these heels into your skanky little ass. I am going to let Mr. Creampie take my cherry and I don't want an audience while he does it. As I said, you better not still be at my house when I get home tonight. As for tomorrow afternoon, you better not show up at my house as I need to talk to my daddy alone. Is all of this clear, you little shit?"

"Y-yes, it's clear," he stammered.

Dieter ran from the room to get away from his furious former friend, not caring that he was still looking like a dirty, little sissyboy whore. There was silence in the room as Jason calmed down.

"You're quite the little tiger, boy," Alex Creampie said with respect in his voice.

"How long did you know it was happening?" Jason asked. "You didn't exactly seem surprised to hear what I saw."

"About a year and a half," Alex said. "I warned Dieter that he should tell you what was happening, that you would be as angry as you would be if you caught them at it."

"You're right, I wouldn't have been," Jason agreed. "The worst thing about their deceit was that they did it in such a homophobic way. Then I find them doing the gayest thing men and boys can do together."

"So are you ready for your virginity to disappear?" Alex said.

"You bet," Jason said. "But let's get something straight. This is only about sex. I am here to get fucked, not have you become my man. If I enjoy myself, I will likely come to get fucked on a regular basis, but never kid yourself, if I find a man to have a relationship with like Dieter and my daddy, you will most likely never see me again. That's how it's gonna be. Do you accept that or do I get dressed and leave you to deal with that hardon yourself?"

"I can live with that," Alex said. He suddenly felt sorry for Matt Spermer, who apparently unaware that his son was now furious with him. The boy was certainly his father's son and he wished he could be a fly on the wall for that confrontation. "How do you want to do it?"

"Anyway you want," Jason said.

Alex led Jason to the bed and placed him on his back. Alex was an experienced fucker of boys and so he always engaged in lubrication, dilation and penetration. He instructed Jason to pull his legs back. When Jason did so, he placed his mouth right over the boy's cock. He knew that the boy would not last long and he was right. After only about 5 minutes, Jason screamed with his first boy's time. The man did not give him a chance to rest from his climax and he shoved his face into Jason butt crack and for the first time in his life, the boy felt a tongue on his asshole.

Oh wow.

Jason had heard of this and seen it on the Try Boys site, but he'd thought the idea kinda gross. After all, that was where guys poop from. But within 30 seconds after Mr. Creampie's long, thick tongue slid into his rectum, he was a devotee to the act, receiving it at least; the jury was still out on whether he would ever do it to anyone else. However, after 20 minutes of receiving the ass eating of a lifetime, Jason had decided that he would no doubt do it to please his man when he found him. Alex Creampie's tongue in his pootie had taken him through two, almost three more screaming boygasms.

Creampie reluctantly removed his face from the boy's ass, knowing that the process of dilation needed to proceed. He grabbed the bottle of Spermbutt that he always had handy. He had to admit that this process of fucking boys was much easier now that it was legal and accepted, especially now that he didn't have to hide the lubricant. He put some on his right index finger and placed it against Jason's love hole, rubbing it slightly. Jason moaned at the new sensations and after the tenth rub, Alex slid half his finger into the boy's ass and quickly found the boy's happy spot. Boygasm Express number three slammed into Jason's body immediately and he screamed his pleasure again. Jason couldn't imagine anything feeling as good as what he had so far experienced.

"Jesus Christ, what the fuck was that?!" he gasped.

"That, my boy, was my finger hitting your boy's place, known as your prostate."

Oh so that is what that is. Jason thought. He'd read the word on the Try Boys site but hadn't understood. Another thing he had to be angry at his dad for, neglecting his proper education concerning that most wonderful place. But he was thankful that Mr. Creampie was nice enough to introduce him to it. While he was thinking all that, the man was now sliding his whole finger easily in and out of his anus. Jason was then disappointed when the finger was removed, but quickly realized that its removal was necessary so his pleasure could continue and his dream be realized. The man repeated the process until he had four of his thick fingers pounding in and out of Jason's road to paradise. Jason was proud of himself for taking so many of the man's fingers and figured that getting fucking wouldn't hurt now. "Fuck me now!" he ordered. Alex shrugged and reached down to where his clothes were and picked up his thick leather belt before offering it to Jason.

"You might want this to bite on in case this hurts," he said.

"I don't need that," Jason said with a touch of bravado. "I can handle it."

Ah the innocence of the virgin sissyboy. Like every sissyboy in history, Jason Spermer was about to find out that taking a man's cock is a much different thing than taking his fingers. Fingers can really only stretch the anus one direction at a time, but a cock can, and does, stretch the anus in all directions at once. Alex moved between Jason's legs as he put more Spermbutt on his massive cock. He placed his fat cockhead at Jason's entrance and gave a mighty push so that four inches of black cock were buried inside the tight, white boypussy. The scream that ripped out of Jason's lungs was so loud that every person walking by the staircase heard it. All of the boys, the male teachers and even most of the female teachers knew what that scream meant that another young sissyboy was being introduced to his true destiny as a cock-craving slut.

Of course the thoughts racing through Jason's mind at the moment were quite different. Earlier on, he had found it amazing that his little puckered hole could be the source of such mind blowing pleasure, at that moment; he was equally surprised by the fact that it could be such a source of pain. He expected to soon hear the tell tale ripping sound as his body was torn in two by the man's fat knob, and he knew that the worst was yet to come: The man's cock was MUCH thicker at the base than at the knob. It was almost enough to make him call the whole thing off and apply for one of those heterosexual cards. Almost. As he hitched his breath to scream again, Alex took the opportunity to shove the rest of his massive boypleaser where it belonged so he was all in. As he did that his thick cock, rubbed Jason's boy's place for the first time.

Oh. Oh my.

Any thoughts Jason had about returning to heterosexuality disappeared as the electric shock from his magic button went through his body. And in its wake, a large amount of the pain had vanished. He just felt like he had to shit really badly. He looked up into the man's eyes and said only two words.

"Now. Please."

Jason's first experience of sodomy lasted only fifteen minutes and three boygasms before the man made his first sperm deposit in his pussy. Creampie can be forgiven though as he was too horned up both from Dieter and preparing the brunette beauty for his cock. But he was not about to let the boy out of that room until he had received the best fucking Alex Creampie could give him. He pulled his cock out of the boy and walked over to the PA speaker on the wall. He contacted the office and let them know that Jason Spermer was going to be helping him with something that afternoon and would be absent from his classes. By the time he reached the bed once more, he was ready for fuck number two.

Fuck number two was performed much more to the man's satisfaction. He pushed Jason farther up on the bed and climbed on himself. He pushed Jason's legs back and this time wasted no time in sinking his whole cock back into the boy's sperm drooling pussy. This time he let the boy's heels rest on his shoulders and leaned all his weight forward so that Jason was in a helpless little ball and bore the brunt of a large portion of the man's weight. The thirty-five minute second round resulted in Jason having five more dry orgasms and receiving a second load of thick man cream in his naughty place.

Alex removed his cock from the boy's depths and rolled over to lie beside him. Jason snuggled up to him and draped his left arm over the man belly while resting his head on the man's chest. Jason kissed the man's solid pectoral muscle and then proceeded to begin gently licking it. Meanwhile his tiny hand began to rub the man's belly before moving south to the penis that had taken him to paradise so many times. He stroked it for a few minutes while trying to make up his mind. Finally he moved downward on the bed so that his face was level with the man's cock. He took it in his right hand and placed it to his lips. He kissed the tip and then let his tongue wander over the sensitive knob. He noticed a bead of precum in the slit and he licked it away. After a couple of minutes of licking that way, he opened his mouth and took as much as he could into his hot little mouth. His head bobbed up and down until the man's penis inflated once again. Jason was about to ask the man to get on top and fuck him again but he decided that Mr. Creampie looked rather tired out. Jason thought back to the night before. Hadn't he seen something a sissyboy can do in situations like this?

Of course. Jason remembered what he had seen on the Try Boys site. He moved to straddle the man's middle, reached down to angle the stiff rod where he needed it and, with a moan, he sank down on the man's shaft. Alex gasped as he felt the remnants of two previous sperm loads dripping and running down his cock from the boy's weakened anus muscles. Finally Jason settled down unto the man's groin, feeling the man's large sack in his butt crack. He began to move slightly and then became more vigorous as he experienced the new angles that the massive penis touched his prostate with. His hips rose, fell, rocked and oscillated as he rode his man through seven of his dry cums and two sperm injections from Creampie.

It was a very tired and sore Jason Spermer, who walked out of the Janitor's room that day. But it was a very happy one. He didn't have the strength to walk to Uncle Amos' so he called a cab. But before you're too harsh with him, consider that, at least, Jason is still conscious. Mr. Creampie is passed out on his bed, dead to the world. As Jason climbed into the cab, he hoped that his uncle would have a solution to his problem.