Date: Mon, 01 Dec 2008 17:56:57 -0500 From: Wolf Subject: Sissy-Boy Forever (gay/incest, b/M, b/MM) DISCLAIMER: This story is a work of fiction and contains descriptions of explicit sexual acts of boy's discovering their sexuality. It contains graphic scenes of sex between an underage boy and adult males... If this type of content offends you or you are under the age of 18 do not read it. Author's Note: This story is the property of the author. It can be downloaded for personal reading pleasure or sending to a friend, but if you wish to re-post them at your own site, please contact the author for permission. If it is illegal to read such material where you live or if you find the topic deceitful the please leave now. If you enjoy the story or if it evokes memories of your own, please let me know. I am happy to write stories from outlines. Copyright 2008 Wolf, All rights reserved. You may contact me at whitewold999@icqmail.com if you like. All flames will be ignored. Sissy-Boy Forever By Wolf It is hard to be a sissy-boy in a family of rednecks. Jason was the youngest child in a family of four boys. His mother was protective of his feminine side. She allowed him to let his black hair grow to shoulder length. He had to endue a lot physical abuse from his older brothers because his effeminate behavior. School was no better. He was not very athletic so the boys never picked him to play any games. Besides he didn't like being knocked around. His aversion to outdoor games made him more of an indoor type as a result he had pale skin and soft skinned. From the back he was mistaken for a girl. He would much rather play with the girls. His best friend at school was a girl that protected him from the bulling by the boys. When he would visit her home she would style his hair like a girl. Even if she put it in a ponytail she would give him bangs and curl the hair in the tail. They would put on makeup. She taught him the proper way to apply makeup. She even envied his long eyelashes and blue-green eyes. They were very close to being the same size too. She spent hours admiring what a pretty girl he would have been. From the age of 10 she would allow him to wear her sexy panties. He would return them to her for washing. When he reached the age of 13 his mother also indulged his fascination for makeup and women's sexy underwear. She would buy him girl's clothes and allow him to wear them around the house. When he reached the age of 15 he would even wear makeup in public. His feminine appearance always drew the attention of adults. Women commented of what a pretty boy he was. Men would tell him they would like to fuck him. The idea appealed to very much. When he learned from his brothers that there were men that like to have sex with sweet little boys like him, he could think of nothing else. He was jacking-off long before he was able to cum. Eventually he had the chance to find out what it would be like to have sex with a man. He was walking home just before he turned 13 and a man approached him. The man was very flattering about his looks. When the man suggested that he accompany him home because he would like to see what he would look like in some dresses he had Jason accepted his offer. The man led him to his house and it was not far from his own home. He felt a little safer knowing he was so close to home. As soon as they were behind closed doors the man wanted to touch his body. Jason enjoyed the way he gently stroked his body. The man wanted to get him relaxed. So he offered to share some marijuana with him. Jason knew his older brothers smoked joints but they would never share it with him. He agreed to try it. The man had a little glass pipe that he filled with a small amount of weed and lit up. He held in the smoke as he passed the pipe to Jason. Jason had never smoke pot before and exhaled as soon as he had taken it into his lungs. They were both coughing. The man told Jason that he had to hold the smoke in his lungs as long as he could. The second drag Jason took he tried to hold it in as long as possible. He was sputtering as the urge to cough was strong. Eventually he had to let it go. It took a few minutes before Jason felt anything. The first thing he noticed was it seemed to get darker. It felt as if his body was disconnected from his mind. The man brought out some girl's dresses that were very frilly which got Jason excited. He peeled off his clothes with no thought about the fact that he was getting naked in front of a stranger. She put on the tight fitting little lace panties before putting on the dress. He also put on ankle socks and Mary- Jane shoes. When the man pulled him onto his lap and started feeling him up it felt like it was someone else's body that was being touched but it felt good. His little penis was as hard as it had ever been. The man had his hand under his dress rubbing his little boner through the sexy panties. Eventually the man slipped his hand down the front of the panties and took hold of his boner with his thumb and a couple of fingers and jacked-him-off while he was kissing Jason on the mouth. Jason was in heaven and was returning the kisses with enthusiasm as the man cupped his little scrotum. The man's finger traced the seam down the middle of his sack right to his little asshole. Jason could not believe how good it felt having the man play with his asshole. When the tip of his finger penetrated his asshole it shocked him and he puckered his asshole tightly on the finger tip. It hurt so he relaxed and when he did the man stuffed his finger up his ass all of the way. When the man started stroking his finger in and out Jason could not believe how his little cock reacted. It was bouncing up and down against his smooth pubis. When the man removed his own pants Jason knelt before him and took his cock in both hands and started sucking on the knob until he got a mouthful of cum. He was shocked by the warmth of it but he didn't mind the taste. He had had to change clothes before going home but he had every intention of returning as soon as he could. He would drop by to visit the man two or three times a week. When he would drop by the man would often greet him wearing silk jogging shorts. He never had underwear on under them so that his cock and scrotum would be exposed when he sat down with Jason sitting on his lap. That way the sissy-boy could play with his cock while the kissed and the man felt him up. He was having the greatest time of his life. It was not so bad at home by that time. His two oldest brothers were in the Army by that time and the other brother was away at college. There were just his parents at home. His father had very little to do with him because he didn't approve of him wearing makeup. There was no loved lost between them. One day when Jason got home his mother had left a note that she was visiting a friend of hers and would not be home until later that evening. Jason started making dinner for him and his father. When his father got home he read the note and didn't say much about it. He took a shower while Jason finished making dinner. When his father came back to the kitchen he was dressed casually. Dinner was quiet. His father went to the living-room to read his news paper while he watched TV. Jason finished the dishes and joined his father. He was watching the TV until his father finished reading the paper. He did not see the way his father looked at him. He told Jason to come to him. As Jason stood up and approached his father his dad was unzipping his trousers and pulling his cock out of his pants. He was holding it by the shaft as he told Jason to suck his cock. Jason knelt between his legs and started sucking on his father's cock. When his father's cock was fully engorged with blood his father stood up and pushed Jason backwards and onto his back. His father unfastened his pants and pulled them off of his legs. His father had a snarl on his face when he saw the delicate lace panties on his son. He said, "If you want to be a sissy-boy you might as well be one." With that he pulled them down to his ankles and lifted his legs up knelt on the floor with his knees touching Jason's smooth butt. While he held Jason's ankles with one hand he guided his cock against the virgin rosebud. Jason had never had anything larger that that man's finger in his ass before. Now his own father was forcing his cock into his asshole and the pain caused tears to well up in his eyes and he pleaded with his father to take it out. There was no stopping his father at that point. He stuffing all of his cock in Jason's ass and fucked him hard. By the time his father squirted cum in his ass Jason was beyond crying any longer. His asshole felt like it was on fire. When his father pulled his cock out of his ass felt like his guts were going to fall out of his asshole. He felt liquid seeping out of his asshole and pooling under his butt. He thought it was his own blood. It was not until he sat up and moved back that he saw that the liquid was not blood. It had to be his father's cum. He slowly stood up and waddled to the bathroom to shit and take a bath. He avoided being around his father for awhile. Nothing was said between them about what had happened. When he visited his adult friend he told him what his father had done. The man wanted to inspect his asshole. He told him that now that he was not a virgin it would get easer to be fucked. They talked about it and Jason agreed to try it again. The man retrieved a jar of Vaseline from the bathroom and greased up Jason's asshole and his cock. When he had Jason lay on his bed in the missionary position and placed Jason's heels on his shoulders as he guided his cock into the little rosebud. The man took it slowly and watched Jason's sphincter spread open to accommodate the knob. He would stop and pull back a little when he saw the pain on Jason's face. He took his time and slowly worked his cock in until his pubic hair was pressed tightly against Jason's little scrotum. When he started fucking Jason he took hold of Jason's cock and jacked him off while he fucked him. When the man was finished Jason wanted to see his asshole so the man held a small makeup mirror between his legs so that Jason could see his own asshole. It was the shape of the man's cock and the skin around the opening was swollen and an angry red color. His asshole hurt but was a little numb. It hurt even more when I tried to pucker his asshole up. The two of them bathed together before Jason had to go home. Jason waited a few days before visiting the man to try that again. When they retreated to the bedroom Jason found that it was not as uncomfortable this time to take is cock up his ass. The next time they did it Jason actually climaxed and squirted cum all over his own belly. He became a regular little cock hound after that. It was not long after that his mother was spending an evening out with her girlfriend again. This time his father came to his room in only his boxer shorts. Jason didn't resist as his father prepared to fuck his ass. His father was just as rough as before only this time while his father was fucking his ass Jason shot cum all over his chest and chin. His father watched Jason squirting cum all over himself before he filled Jason's ass with cum. He had Jason suck his cock clean before he went back to his own bedroom. Again nothing was said about what had taken place. When the weekend arrived his father told his mother that he was taking Jason with him to watch football with his buddy. Jason was not thrilled about having to watch football all day with his father's buddy. He wanted to object but his gave him a look that told him to keep his mouth shut. His father's buddy was the kind of man that frightened Jason. He was about six-feet tall and could have been the model for Pop-Pye the sailor man's adversary Bluto. He was a large dark hairy man that always looked like he needed a shave. He tended to be chewing on the butt of a cigar all of the time. Jason was frightened by him. So he was not happy about being forced to go with his father. When the two men settled down to watch the game his father told him to bring them a couple of beers. When he returned with two cans of beer his father said, "Take off you pants Son and show Bill your panties!" Jason knew better than to object. He simply unfastened his pants and pulled them down to his knees. Bill reached over and felt the crotch of the black lace panties. He had a nasty grin on his face with a stinking cigar butt sticking out of his teeth. Jason was still a small youth of no more than 120 pounds. The man's hands were large and rough. Hell! Each of his fingers was larger than Jason's little cock. He didn't move as the man pulled his panties down to have a look at his little pecker and balls. He rolled the soft flesh in his callused fingers and pulled on his little cock. He turned Jason around and made him bend over and support himself by holding onto the edge of the coffee table. He spread Jason's butt and ran a finger up and down the crack. Jason did flinch with the big index finger invaded his asshole. Bill made him knee across the table. When Jason looked at his father he was taking off his clothes. He had to turn his body to see what Bill was doing. He was taking his clothes off too. Jason was starting to sweat when he saw what Bill looked like. To begin with his chest had to be at least 50-inches around and his waist was close to 60- inches around. When Bill turned his back to him to take off his pants Jason saw that not only was his back hairy there were hairs on his butt. When Bill turned to face him he saw that the front of his body was just as hairy. The sides of his belly didn't have much hair because of the friction of his arms. The hair on his chest was thick and turning gray. When Jason checked out his crotch he saw that Bill's cock was nestled in a think mat of pubic hair. The balls were covered in hair but the cock was frightening to him because he had never seen a cock like that before. It was larger than anything he had ever seen and the skin was dark too. This was the first un-cut cock he had ever seen. The foreskin reminded him of the eggs in the movie "Aliens". The skin covered the knob and some of the skin dangled past the knob. Bill skinned back the foreskin to show Jason that he had a knob like any other man. The head was wet and it smelled so strong Jason could smell his cock from where he was laying. Bill placed his big meat hooks on Jason's butt and spread the cheeks and spit on his asshole. Jason cringed because he knew what was coming. His father came around the table and grabbed a handful of hair as he stuffed his cock in Jason's mouth. While he was accepting his father's cock Bill was stuffing that fat baseball handle sized cock into his boy-pussy. He would have screamed but his mouth was full. There was nothing to do but endure the fucking. To his astonishment he squirted cum all over the coffee table before either of the man came in him. The men had a couple of more beers and talked about what a sweet sissy-pussy Jason was. They fucked him again before the second game for the day was over. Jason was finally allowed to bath and get dressed before his father took him home. Jason did everything he could to walk normally but he must have looked like he was waddling a little. His mother never mentioned it though. It was not until he was getting undressed for bed that he checked his pocket and found a slip of paper with Bill's phone number on it. He had no intention of ever seeing him again. He tossed the paper into his trashcan and went to bed. In the morning he woke up with a raging hard-on and fished out the slip of paper and put it in his backpack. He called Bill and asked him if he could drop by after school. Bill assured him that he was welcome and he would have a stiffy waiting for him. If you enjoyed the story and have a story you want me to write about your introduction to the world of male sexuality, please send your outline to whitewold999@icqmail.com