Sissyboy Gets His Man
Author's Note: This story takes place in one of the many worlds created by Beautiful Creamer: The "Try Boys" and "Try Men" world. He has graciously allowed me to attempt to play in this world for a bit and I hope he likes my attempt. If you have not yet experienced the writings of Beautiful Creamer, I strongly urge you to do so.
The Story Begins: Daddy's First Sissyboy
Matthew Spermer just could not keep from chuckling when the ads for "Try Boys" and "Try Men" began to appear. He had been "trying" boys and boys had been "trying" him for the past three years. He was trying boys back when it had to be very well hidden, the dark times before Biff Buggerall had created Sissyboy Magazine. Up until three years before, Matthew had been a full, card-carrying heterosexual male in good standing. More than that, Matthew Spermer was a stud. And adding to his appeal was the fact that he was a multiple time NFL MVP as the starting Quarterback for the Washington Redskins. He had access to hot and cold running women. But no one knew what was boiling beneath Matt's heterosexual exterior.
It was about four years before when his attitude toward women began to change. That seems strange to hear considering that he was known as the sexiest man alive. He had dark chestnut coloured hair which was kept stylishly cut. He had piercing, ice-blue eyes and his face was free of any blemishes. Whenever he did a photo shoot, the photographers always commented on how he was the only person they had ever encountered that required no airbrushing being done to his photos. His body was lean and buff, not an ounce of excess body fat on him. He was also strong as an ox; he could even out lift some of the linemen he played with. But what was most impressive about him and the thing that should have ensured his infinite happiness with any woman or women of his choice was the size of his penis. Matthew Spermer was hung like a God. Inside his pants were lurking twelve inches of fat mancock and he knew how to use it. He made the women scream and then scream for more. So as far as everyone knew, Matt had it all. But all was not well in paradise.
You see, Matt Spermer was getting fed up with women. He had found them self-centered, manipulative, bossy, controlling and emasculating. But he could have handled all that except for the straw that was in danger of breaking the back of the camel: Women can be stingy when it comes to sex, and when they do deign to allow a man to touch them, they bitch and moan about how he isn't doing it right. Matt was becoming more and more miserable, until his center and best friend had the balls to straighten him out, and he took his friend's advice. Matt's final thought as he read the words of the Try Boys ad: "Tired of the nagging, manipulation and emasculation? Try boys." was that truer words of wisdom had never been spoken. His mind then flashed back to the events that turned him from a devoted fucker of women to a devoted fucker of young sissyboys.
(Three Years Before)
That Sunday was a day of surprises for Matt Spermer. He had just got finished playing the worst game of his life, throwing seven interceptions and fumbling five times in a huge loss to the Detroit Lions. The loss had dropped the Redskins to 0-8. Matt had never been 0-8 before in his life and the only reason that his QB rating wasn't a negative was because that was impossible. And on top of the bad game was the fact that before the season, his supermodel wife had divorced him, leaving him to raise their six-year-old son alone and Matt hadn't gotten over it. It hadn't been a happy marriage, but it still hurt him.
So Matt was pretty despondent as he sat in front of the locker answering all the dumb, obvious questions from the news media. When the crowd moved away, his best friend and his Center, Amos Diddleswell, walked up and asked him to come over to his apartment after they left the stadium.
"Well, I had planned on just going home afterward," Matt said. "My son's having his best friend stay over for the first time tonight. They're with my mom now."
"Dude, we seriously need to talk," Diddleswell said. "Can't you call her and ask her to stay with them for another hour?"
"Oh, all right," Matt said and made the call.
He followed Amos to his apartment and they sat down in the living room and Amos asked Matt if he would like anything to drink. Matt declined, saying that if he started, he might not stop and he didn't want to face two active little boys with a hangover. Amos poured himself a drink and gulped it down quickly. He sat down across from Matt and there was an uncomfortable silence in the room.
"The shit's gotta stop, Matt," Amos said finally.
"What shit, Amos?" Matt asked.
"You fucking around with women," Amos said. "We've been best friends since grade school, Matt, and I've seen all I can stand to see."
"What are you talking about?" Matt said.
"Dude, when we met you were the happiest boy I had ever met, that was why I wanted to be your best friend. It didn't matter what we were doing, you always had fun doing it, especially the stuff we did in my tent during sleepovers," Amos said, then suddenly sounded sad. "But after you discovered girls, man, you were never that happy again. From the very first girl, I could tell that they were having a bad effect on you. Face it, guy, girls and women are bitches."
Matt was silent, waiting for his friend to get to his point.
"The fact is Matt, that women are self-centered, manipulative, bossy, controlling and emasculating. Not to mention the thousands of times I listened to you bitch because they won't give it up and when they do, they always make you feel like you're doing it wrong," Amos said. "And on top of everything else, you're playing like shit because you're still messed up over the Queen Bitch leaving you and Jason. You need to find someone else, man, and soon."
"I'm confused, buddy," Matt said. "You've spent the past few minutes telling me how shitty women can be, yet you say I need to find someone soon. So what am I to do?" he paused and then said, "What about you then? I'm sure you're getting all the sex you want, but I never see a chick around. So how are you getting it?"
Amos got suddenly nervous. "I'll show you because you're my friend, but you have to promise that, even if you don't like what you are about to see, you will keep it to yourself."
"I promise," Matt said.
Amos took a deep breath and let it out. "JARED!" he called. "Can you come out here please?"
Matt was surprised that the boy was there. His ten-year-old Godson usually lived with his mother and it wasn't a school vacation. And why did Amos call out his son in answer to Matt's question? Surely he didn't mean....
Then when the little blonde boy came into the room, Matt was quickly able to see that Amos did in fact mean what Matt suspected. It was kind of hard to miss. The boy came out wearing a very flimsy and sheer pink baby doll nighty. He was also wearing a pair of the sexiest, laciest, pink panties. They were so tight that the little boy's boner was totally obvious. The ensemble was topped off by the pair of reinforced heel/toe stockings and garter belt as well as a pair of stilettos. Matt knew he should be disgusted, but he wasn't. In fact, part of him had risen up to take notice of the achingly beautiful boy.
The boy walked over to his daddy and crawled up into his lap. They kissed like long lost lovers. But when they stopped, and as Jared continued to tease his daddy, Amos told him the whole story. How he too had broken up with his wife, and filled the void by discovering the number of little boys that liked mancock. But he said that he never loved any of them until Jared dropped into his lap, figuratively and literally. His ex had discovered the boy wearing her lingerie and just before she shipped him to live with Amos, he was discovered sucking the cock of the school janitor. Amos then described how his son's anal virginity didn't last the night.
Again Matt knew he should be disgusted and should have gotten up and left, but he stayed. And he watched with interest as his two hundred and ninety pound best friend placed his seventy-five pound son on the floor on his back and turned into a lust-filled, snorting, rutting animal as he pounded eleven inches of thick cock in and out of the boy's well used pussy. The whole process interested Matt greatly. In spite of himself, he thought the sight of the small stiletto and stocking clad feet on his friend's broad, manly shoulders was kinda hot. But it was the boy's reactions to the whole thing that really surprised him: the boy actually LIKED what his daddy was doing to him! Not just liked, LOVED it! Matt was turned on by the boy's whimpers, squeals, squeaks, pleas for more cock and pleas for it harder and deeper as well as the many times the boy chanted "Daddy, I love you", were like nothing he had ever heard before. But the piece de resistance was the loud screams as the boy came to have his dry "boy's time". There were three such times and during the last time, Amos cried out and announced that he was breeding his boy's pussy.
When Matt left for home, he took the "scenic route" as he had lots to think about. He did think that what he had seen in Amos' apartment was one of the hottest things he had ever seen, but he couldn't imagine making boys a full substitute for women. What about when he wanted real pussy?! (Lord, are heterosexuals so foolish sometimes). He decided that it was worth a shot to try a young boy, and then started to think who he might try. He immediately decided that Jason, his six-year-old was out of the question, as he was so innocent. But there was that friend of his, Dieter von Squiggler, who was a year younger than Jason. Matt has noticed that Dieter has started looking at Matt in a funny way. A lot the way that Jared Diddleswell looked at his father. Could a five-year-old boy REALLY be sexually aware enough to want a man's cock? Matt didn't know for sure, but he resolved to himself that he would find out that night. But he had to make sure that Jason didn't discover them, and then he got an idea and called Jason's Paediatrician. He asked the man if a sleeping pill would hurt Jason. The answer satisfied him and he hung up, just before he reached his home.
Speaking of young master von Squiggler, if Matt had been able to see the boy's thoughts that night, he would have quickly realized that, at least for the German boy, the answer to his questions about a five-year-old being sexually aware enough to desire mancock was a resounding YES! But up to three weeks before that answer would have been quite the opposite. But something had happened three weeks before that had changed Dieter's life. Some people believe that as children gain knowledge, they lose their innocence. Well, I'm not sure if that's true or not, but three weeks before Dieter did gain some new knowledge about his father and older brother and he was certainly less innocent because of it.
Dieter had been playing at a friend's house, but unexpectedly, the friend and his mom had to go away, forcing Dieter to return home earlier than he had told his daddy he would be. Dieter lived with just his daddy and twelve-year-old Joran. His mom had left them three years before when Dieter was just two-years-old. Dieter walked in the door of their home and was surprised to hear no noise coming from the TV room. Daddy and Joran had both said they were going to watch a soccer game. Dieter hated soccer and said he was going to go to his friend's. Daddy said okay and as Dieter later remembered, both daddy and Jor seemed anxious to get him out of the house.
It wasn't until Dieter moved his search for his father and brother upstairs that he heard the first noises. As he approached the Master bedroom, he heard the first sounds coming from that room. It sounded like sex sounds. Dieter had heard the noises many times form inside daddy's room when daddy used to have women over. Until that moment it hadn't occurred to him that daddy had suddenly stopped having women over in the past year and a half. And where was Joran at if daddy was having sex with a woman in his room? He didn't know. But he knew daddy was having sex with someone. He recognized daddy's grunts and snorts as he worked and occasionally he would tell his partner to take daddy's cock like a good little bitch slut. Occasionally, the other person would make some noises too, mostly squeals and squeaks as Daddy's cock was rather big: a thick nine inches. Today was no different, in that the person was squeaking and squealing like mad. Dieter was again surprised that his brother was nowhere to be seen as his was the one that got Dieter into listening at their daddy's door while he was fucking someone.
Then came the first new thing of that fateful day. As he got closer to the room, he recognized that the second voice doing all the squeaking and squealing was not a woman's voice. It actually sounded like a boy's voice, an older boy's voice. Dieter was shocked by the idea of his studly daddy fucking a boy. He began to wonder who the boy was and wonder if Joran knew. But when he got almost to the door, he suddenly knew who the boy was and knew that Joran was fully aware of it.
"FUCK ME DADDY!" Joran cried out. "FUCK ME HARD! MAKE ME YOUR BITCH, YOUR SLUT, YOUR WHORE!"
No! No! It CAN'T be! Dieter thought. His mind refused to believe that his homophobic daddy and big brother were in that room fucking. It had to be some kind of trick! His hand woodenly pushed the barely open door so he could step into the room. And when he did, he finally had no choice but to accept it. He couldn't believe what his eyes were telling him, but he couldn't deny it either.
The bed was perpendicular to the far wall and his father and brother were on the bed so that Daddy's back was to the door so they had no idea that he was in the room. His daddy's naked form was as he had imagined it. He was muscular and buff. His ass looked like it had been chiselled from granite. And all he could see of his older brother were his legs from the lower calf down as they rested on daddy's manly shoulders. He was shocked to see that his brother was wearing a pair of white silk stockings and stiletto heels. The only other part of Joran that could be seen was they part between daddy's legs where daddy's massive rammer was sawing in and out of his brother's bum. Any doubts about what they were really doing were gone. Joran was being daddy's bitch. And Dieter was able to work out the fact that the reason there had been no more women overnight, or at all actually, was because daddy didn't NEED to have women any more: he had Joran's boypussy to fuck. And from the looks of things, daddy used Joran's pussy every chance he got. And he now understood their eagerness to get him out of the house.
As the three intervening weeks went by, Dieter looked at his father and brother differently. At first he was angry because he wondered how they could pretend to hate gays, when they were doing gay things with each other. But he calmed down when he remembered that they had to do that, to avoid daddy getting into trouble. And as he observed them with his fresh insights, he realized that they really did seem to love one another in a special way. They looked at each other the way men and boys were supposed to look at females. He forgave their hypocrisy without telling them. After all, they still had no idea that he had seen them fucking. But he did have some real thinking to do. Starting the second week, as he was standing outside daddy's bedroom listening as daddy and Joran were at it again because they thought he was asleep, he started to feel envious of Joran. He wondered if he could find a man to fuck him like that. He knew it would be harder because he was only five. But he immediately began to think about candidates. The first man to occur to him was matt Spermer, the daddy of his best friend Jason. Mr. Spermer was a God in Dieter's little eyes, he was kinda of a hunk.
So for the next two weeks, Dieter spent a LOT of time at Jason's house. Daddy and Joran never questioned it, as it meant they had more time to fuck without worrying about Dieter discovering them. And whenever Mr. Spermer was there, the young German boy started giving him those long, smouldering, pouty looks that sissyboys have used throughout time to seduce the man they want. But Dieter was shocked that there was no effect on the man! He was totally oblivious to what Dieter was offering and Dieter couldn't understand it. Ever since he had seen his father and brother, he suddenly knew that there were men that would like to be with him. Men at the mall or other stores would stop and look whenever Dieter was around. And Dieter could understand that. He knew that men seemed to like the way he looked: his blonde hair, blue eyes and his tight little butt that he started showing off whenever he could. But it seemed that the one man that was the most oblivious to his beauty and charms was the one man he wanted above all others.
So as he sat there on that fateful night in his pants and shoes, which were hiding the pair of white panties and white stockings he was wearing, he had decided that one way or another, Matt Spermer's cock was going into his mouth and up his ass before he went home the next day. He really didn't know how he would do it without Jason knowing but it was happening whether Jason found out or not. He heard that Jason was still prattling on without really listening; his mind was too busy imagining what losing his cherry would feel like.
Matt arrived home to find the two boys sitting and watching TV quietly. He greeted his mother and saw her out the door and then greeted his son. But it was when he turned to look at Dieter that his heart almost stopped. Dieter was giving him one of the looks he had started using a couple of weeks before. Now Matt knew what it meant. God damn, Matt thought. The kid's been trying to show me for two weeks that he wants my cock and I had no clue. He mentally thanked Amos for clueing him in and decided he better let the boy know that the message had gotten through this time, so he used to age old sign of a shared secret: he gave his son's best friend a wink.
As Matt had come in the house and greeted his mother and son, Dieter was rapidly losing his nerve. But when Matt turned to look at him, he gave him another of those looks. There was a slight silence as if the man was thinking hard about something and then it came, the sign that Dieter had been praying for: a wink. Just a short up and down movement of the right eyelid, but it spoke volumes. It said that not only was Dieter's message finally being received, but it was also welcomed and returned! Dieter still wasn't sure how the Jason problem would be dealt with, but he was sure that the man would find a way.
Matt and Dieter spent the next two or three hours in agony. They wanted to just get rid of Jason so they could just get on with what they both wanted and needed. For Matt it brought back memories of going through a similar thing with his parents when he got his first girlfriend, waiting for them to finally go to bed so he could make love with the girl. For his part, Dieter was sorry that he would be going behind his friend's back, but not sorry enough to not do what he needed to.
Then around seven-thirty, Matt asked the boys if they wanted a glass of soda. While he was in the kitchen, he called the Paediatrician and asked if the medication would dissolve in soda, hearing that it would, Matt hung up. He poured three glasses of Coke and then opened one of his sleeping pills. He poured the medicine into Jason's favourite glass and stirred it in. He felt a twinge of guilt at drugging his son for a chance to fuck his best friend, but as they say, a stiff cock has no conscience. Matt HAD to find out if what he had seen at Amos' was true with boys other than Jared. And besides, he knew that Dieter's tight, virgin ass would be the best thing he'd ever felt around his massive cock.
So he returned to the living room, distributed the drinks and settled in to watch a movie with the boys. As boys will often do when sitting with a man, both boys snuggled up on either side of Matt. Matt kept taking quick glances over to see if the sleeping meds were taking their toll on his son and was pleased that they were. Jason's head started drooping and he would yank it back up, trying in vain to fight off the urge to sleep. But he was merely delaying the inevitable. Fifteen minutes later, Jason was overcome and slipped into dreamland. He gave a little boyish snore and Matt knew he was out. He turned to the boy on the other side and kissed him on the lips, just a peck, but a preview of things to come, so to speak.
"Be right back, love," he purred to the boy. "While I'm putting Sleeping Beauty here to bed, why don't you meet me in my bedroom?
"Okay," Dieter chirped happily.
They both got up and headed upstairs. Matt carried the sleeping Jason into the boy's room while Dieter headed for Matt's room. Matt hadn't noticed that Dieter had picked up a small bag and was carrying it with him. When Dieter got into Matt's room, he wondered if he should undress but finally decided that Matt would probably want to undress the boy himself. All he did was sit down and pull a small pair of Stiletto heels out of the small bag and changed out of his trainers in favour of them.
Dieter chose wisely. For when Matt entered the room himself and saw the boy wearing his clothes but also wearing the heels, his cock got harder that it had ever been and it was tenting his pants obscenely with its thick thirteen inch size. Dieter felt the first twang of surprise and trepidation. He had known that Matt Spermer had a massive cock, but he'd REALLY had no idea of its real size. He wondered if it would fit inside him without killing him, then decided he didn't care.
Matt gestured and Dieter ran into his arms and was lifted up by the muscular quarterback. Then man and boy shared their first real kiss. With tongue and lots of spit. Dieter was grinding his little cockle against Matt's suit and Matt's hand were all over the boy's ass. Matt then put the boy down and started to unwrap his prize. He undid the boy's pants and slowly pulled them down, gasping as he realized what the boy was wearing just for him. It took all his willpower to not rip the boy's panties off, rip his suit pants open and bury his cock in that tight ass. But Matt resisted. Although new to boys, Matt had broken in a few virgins in his day and knew what he was doing.
He allowed the boy to undress him until he was wearing only his sport socks. He picked up the small boy and deposited him on the bed on his back. He climbed on the bed himself and took up the dominant position above his boy. His boy. Matt liked the thought of that, that he would soon own the five-year-old boy beneath him.
As for Dieter, despite not knowing the term yet, he accepted his destiny as a sissyboy. Looking up and seeing his man towering about him in the dominant position, made his little boner so hard it started to ache. All he could get out was one plaintive word that summed up all his lust and desire: "Please!"
Matt lowered his head and they kissed again, Dieter getting more into it was his desire was now fully wakened. But Matt soon broke the kiss to start his mouth's first ever voyage down a young boy's body. He had a pretty good idea that it was the first time in the boy's life that a man had undertaken said voyage. And from the very moment his tongue and lips touched the skin of Dieter's throat and neck, Matt was aware of the first difference between making love to a sissyboy rather than a woman. Dieter gave out his first soft moan of pleasure as he surrendered to the new feelings. No woman Matt had ever been with had been that responsive. Maybe the reason was because women understood that doing so merely encouraged a man's lust further. It certainly did in this case. Matt moved downward and latched his mouth over Dieter's erect and puffy left boy nipple.
Dieter gasped at the sensation of Matt's mouth over his nipple and the flicking of the tongue over the rigid nubbin. Like any boy his age, Dieter had often wondered why boys had nipples like girls when they never got boobies. Now he knew the truth. A boy has nipples so his man can make them feel good. He gasped again as Matt took his right nipple between his thumb and index finger and began to rub it. Matt then switched nipples and Dieter said actual words for the first time since Matt had started his work: "Oh yes!"
Matt took that as a signal to work slowly lower until he reached the boy's belly button. Dieter let out a sound that started as a giggle, but ended as a moan as Matt's slippery tongue slid into the little depression in the smooth skin of the boy's belly. Matt was amazed by the fact that he had gone this far in his oral exploration of the boy without the boy once saying, "Don't do that, I don't like it" as was the usual when doing the same with a woman. Dieter, despite only being five-years-old, was willingly submitting himself to Matt to do with as he pleased, much as Jared had been doing with Amos. He realized the second difference between boys and women when it came to sex: sissyboys like to submit to their men. In fact they crave it.
Dieter was in heaven. He had never thought that anything could feel that good. What really amazed the boy was the fact that his every nerve felt like it was on fire, and he recognized that Matt wasn't even near his penis yet. And as he felt Matt's tongue in his belly button, his erect cock started to hurt as it and his little balls began to ache for release. He had often watched as his older brother had masturbated, which Joran had started when he was eleven and he was amazed how at the end, Joran would cry out and begin to shake all over and his dick would twitch. Joran explained that he was having his "boy's time" and how when Joran got old enough, this white goo would come shooting out, an event that happened in front of Dieter's eyes two months later. He himself had never had a boy's time, but he wanted, no, NEEDED to have one now. He wracked his brain for the right words to spur the man to give him what he needed. Then he remembered his brother's usual last cry before he and daddy were finished fucking.
"MATT! OH MATT!" he cried. "PLEASE MAKE ME CUM!"
To Matt that was like the sweetest music he had ever heard. There was just a raw animal passion in the boy's voice that one rarely heard out of a female. He slid down until, for the first time he had his face near another male's cock. He grasped it gently and slid the tight foreskin downward until Dieter's angry purple glans came into view before sliding the skin back upward. He did that a few times to the appreciation of the boy, who at that point was beyond caring HOW Matt made him cum just as long as he did so. But Matt had something else in mind. He retracted the foreskin all the way until it was held in place by the ridge of the glans and then for the first time in his life, his tongue tasted a cock. His tongue lightly touched the sensitive purple flesh and Dieter just about jumped out of his skin for the first of many times that wonderful night. In no time at all, Matt had the entire morsel in his mouth. The effect on little Dieter was immediate. The minute he felt the hot wetness around his cock, he instinctively set to work driving his little nail into the warm moist hole. His hands made their way to Matt's hair as he drove his little hips upwards to fuck the man's mouth. Dieter was moaning up a storm as the strange and powerful sensations were shooting through his body. He especially felt it as the feelings built up especially strongly in his little groin area. He felt the strong urge to pee, but because of his brother's good description of what a boy's time felt like, Dieter knew what he was really feeling and so he didn't pull back at the end like so many boys do at first. He let the Orgasm Express run him over. His little body shook and quaked and a strangled moan/cry escaped his lips and his little balls drew up and his cock twitched, seeking to spew out his non-existent boy's cream. Matt continued sucking until Dieter whined that it had started to hurt and he stopped. Then he received the next surprise.
No sooner had Matt rolled over to lay beside the boy on his back, young Dieter sprang into action. He dove between Matt's legs and before Matt could say or do anything, Dieter had Matt's huge cockhead in his little mouth. Like so many boys in similar positions from the beginning of time, Dieter didn't just start sucking Matt's cock, he attacked it. Women will not suck cock unless they REALLY want something from their man. Most times it's like performing a root canal to get a woman to give a blow job. But a boy will just do it. And do it with gusto. And that is what turns a man on so much about it. Matt placed his hands and pushed Dieter's head so that two inches of his shaft followed his glans into the sucking mouth. Technique-wise, Matt had experienced better blowjobs, but the mere fact of having his cock in the mouth of a little boy and the gusto with which little Dieter was doing his task brought Matt rapidly to the end of the line for his own orgasmic locomotive. He grunted and unloaded his first load on man cream into a boy's mouth.
Dieter was surprised when the first shot of said man cream shot into his mouth. He swallowed as fast as he could, knowing what it was. He quickly found he liked the feeling of it washing over his tongue and the occasional time when a powerful jet would coat his tonsils. He also found the taste was not unpleasant. He swallowed like mad to make sure he got all the hot cream down his throat and into his belly. He then rolled over himself unto his back.
Matt's mind naturally moved to consider how to move things on to the act that he knew both he and the boy wanted more than anything in the world. He thought back to one woman that had wanted something from Matt so badly she had agreed to Matt's request that she take him up the ass. It had apparently not the first time she had taken a cock in her wazoo as she talked Matt through the holy trinity of assfucking: Lubrication, Dilation and Penetration. He figured that would work wonders for Dieter as well. As he wondered what he would use for lubrication, Dieter showed his own eagerness to begin the process of losing his troublesome virginity.
"I need to get something from my knapsack," he said and sprang up off the bed before scampering out the door.
Dieter ran downstairs and opened his backpack. He retrieved a bottle of a substance that would later literally smooth the way for man/boy fucking. It was Spermbutt Anal Lubricant, not even available on the market yet. Dieter knew that his father tested stuff for companies from time to time but didn't realize that the product in his hand had been the result of a conversation between his father and an old friend. When Dieter's daddy had started nailing his older son, he soon realized the limitations of lubricants then available to men for use with their boys. Oil was the best as far as being slippery, but its major drawback was a laxative effect on the one being fucked so if you weren't careful, you might literally fuck the shit out of your partner. Vaseline and other petroleum products were a pain in the ass to clean up from. Water-based lubricants, like KY Jelly, dried out too quickly and couldn't be used when making love in the shower. And soap or body wash tended to cause a burning feeling in the rectum. Dieter's dad lamented about this to his friend that he had messed around with as a boy. The man set to work quickly as he shared the same frustrations with his own sissyboy lover. The result was Spermbutt, the perfect anal lubricant: slippery as water in a polished marble floor without the laxative effect, easy to clean up, didn't dry out and could be used in the shower, and didn't burn like soap products. In his appreciation, the friend sent Dieter's daddy a case before it was ever released on the market and it had been easing the man's way into his twelve-year-old's ass ever since. Dieter knew that what was in the bottle was what his daddy used when he fucked Joran, so in his determination to have Matt fuck him, he had grabbed a bottle, figuring that his daddy wouldn't miss one.
He carried the bottle back upstairs and handed it to Matt before resuming his place on his back on the bed. Matt looked at the bottle and was shocked by the blatancy at the name on it. The name Spermbutt Anal Lubricant certainly made it clear what it was for. He set it aside but within easy reach beside the bed and climbed on the bed himself with his boy. He lifted the boy's legs in the air and spread them, exposing the boy's virgin anus. He got as close as he could and when Dieter's boyscent struck his nostrils; he felt the sudden urge that all men experience when they are this close to a boy's pussy: he wanted to bury his tongue in it. Matt had never done that to anyone, much less a five-year-old boy. He wrestled with his choice for a few seconds.
Matt chose wisely.
Dieter had considered asking Matt to use his tongue on his bottomhole but didn't have the courage to ask; besides he instinctively knew that a good sissyboy waits for his man to come around to it himself.
Dieter also chose wisely.
Matt placed his face in the crack of Dieter's ass and began to lick at the tightly puckered opening like a thirsty canine, willing it to open for his tongue. Matt quickly learned something else about sissyboys as opposed to women: they LOVE analingus. Dieter was no exception as evidenced by him mashing his boypussy against Matt's face all during the man's half hour of feasting on it.
Then Matt knew that it was time for part two. He reached for the bottle of Spermbutt and coated his right index finger with the slippery substance. He put more on said finger and rubbed it on Dieter's anus, still slightly dilated from his tongue. He easily slid his finger into the warm tunnel of the boy's rectum and his finger searched around to see if what he had heard a couple of his gay teammates about the prostate was true. He had almost given up when he found it.
For the second time that night, Dieter jumped out of his skin, or felt like he had, only much stronger. And he was hooked as a bottom boy from that moment. He moaned as Matt began to rub that spot with his finger before sliding his finger in and out. When his finger was moving easily with no resistance, he slid it out of the boy and moved along until he was sliding four thick fingers in and out of the boy's ass. Dieter had taken longer to get used to the dilation caused by each successive finger, and several times pleaded for Matt to "Stop fucking around and just stick it in me!" But Matt was resolute. He knew that even with Dieter now easily taking four fingers, taking a cock was a whole other animal entirely. Fingers only stretch the anus in one direction at a time; a thick mancock stretches it in every direction at once. So, while Matt knew that it was still going to hurt the boy, it would not harm him. Finally Matt deemed Dieter as ready as he was likely to going to get and positioned himself in the classic missionary position with the boys legs in the crooks of his elbows. He took his precum and Spermbutt lubricated rammer and placed it against a male's anus for the first time and pushed.
Matt was glad that he had given Jason that pill and that his house had such thick windows. The scream that came from Dieter's lungs as the massive cockhead and 3 inches of shaft stretched him would have brought Jason running to see what it was and would have caused a neighbour to call the authorities on account of someone being murdered. And someone was being murdered, or at least it felt that way to Dieter. He gathered his breath to scream again and as he did, Matt pushed forward until another three and a half inches slid in, leaving the boy impaled by half his mighty cock. Matt pushed no further, merely allowed the boy to get used to it. He had no experience with boys, but knew enough to think that when a man had a cock like his own, he would have to be a selfish, vile pig to even think of trying to go all in with a five-year-old boy the first time.
It took about fifteen minutes but Dieter finally felt the last of the pain and burning leave him, and then he just felt very full and stuffed, like he needed to go number two very badly but couldn't. He looked down and saw the half of Matt's cock that wasn't inside him.
"It isn't all in yet?" he asked with a tremor in his voice. He really wasn't sure he could take even another inch.
Matt leaned down and kissed him. "No, and it's not going to be, not until I think you're ready to take it all and that won't be for a long time," he said. And then out of the blue these words came out of his mouth. "Me going all in would hurt you badly Dieter. I love you and don't want to do that." As soon as he heard himself say the words, he knew it was true: he did love Dieter.
The words shocked Dieter, especially the words, "I love you". And as he thought about them, he realized that he loved Matt too and said, "I love you too, Matt. Now please fuck me!"
And fuck him, Matt did. For the next forty-five asspounding minutes, the only sounds in the room were the sounds of a man's body colliding with a boy's, the boy's squeaks, squeals, pleas and screams as he had each of his four wonderful boy's times, and the growls and grunts from the snorting, rutting beast that the man had become as he concerned himself only with pounding his cock into the warmest, tightest hole he had ever fucked. In short, a great time was had by all. Finally though, Matt shouted out his triumph and his conquest of the boy, Dieter gave out one last scream as his fifth dry orgasm hit him. Matt rolled over on his side and as Dieter spooned up to his front with his back, Matt quickly slid half his still hard cock back into dieter's pussy. This allowed them to wake up a couple of times during the night to enjoy another nice fuck.
The next morning, Jason was disappointed to learn that Dieter had left just before he awoke. He didn't know what had happened the night before and he didn't know about the three wonderful times that his daddy had fucked his best friend in the shower before he left and how they had agreed to get together every time Jason was not at home. He couldn't understand why he had been so sleepy the night before and why he had slept so late that morning.
Matt put Jason in soccer so he had practice every day after school. And so every afternoon while Jason was at practice, Dieter was at the Spermer's in bed with Matt being fucked silly by the studly man, and the same, of course, happened whenever Dieter slept over, which Matt frequently encouraged. They both felt guilty at first for doing this behind Jason's back, but not guilty enough that it stopped them from carrying on their affair.
Oh and you should know that after Matt hooked up with little Dieter, his play improved dramatically and the team won their last eight games and snuck into the playoffs. Matt's improved play had a couple of really good results: Matt won his first NFL MVP trophy, almost unheard of for it to go to someone on an 8-8 team, and Matt led his team to the Super Bowl Championship, winning MVP of the game honours.
(Back to the present)
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.