On Saturday morning, May 25th,2001, Jason woke up early in a world he was familiar with. He was the oldest of four boys. He was sixteen years old, a junior in high school. He was also a virgin. Not that he was unpopular, he was. He had dated a few girls but never wanted to get them pregnant, so Jason had never crossed that unknown line into the world of sex. He kept the pages damp in his favorite magazine, willing to expel his sperm over nude photos of beautiful girls, just not into a real one.
He found a magazine between his parents’ mattress and box spring. It was a magazine with stories of incest. Maybe that was the reason for having a sexual desire for his mother.
He stood five-foot-nine inches tall, with light brown hair and blue eyes. For the past three years, he had worked on a cow farm part-time during the winter and full-time in the summer. He weighed One Hundred and fifty pounds, nearly all muscle. He shaved his pubic hair because he liked the way it looked. Also, he reasoned that he was tired of his pubic hair getting caught at the end of his penis, which caused him to spray when he peed.
He had jerked his eight-inch-thick cock more than once into the bathroom sink, thinking about… well, his mother. He knew what incest meant, but he also had a hard-on for her.
Let me describe his mother. She was thirty-nine, black hair she let grow until it reached neck level. The prettiest light brown eyes of any woman Jason knew. Her face was slim; her nose was a perfect size. High cheekbones and small puffy lips that he knew were perfect for kissing.
He knew because he read that in his magazine, not through experience.
His father had already left for work, his mother was cleaning up after breakfast, and Jason’s three brothers were about to embark on whatever they wanted to do that morning. The brothers were two years apart; Jason was the oldest.
There was a knock on the front door. Jason opened the door only to have his breath taken out of him.
Jason lived in a small village in Connecticut with about twelve hundred residents. Everyone knew everyone’s business. Even to this day, not that much has changed. Jason and his brothers were close; his family was normal. At least, they would be considered normal by society—two parents, not wealthy, but not poor. A father who worked had served in the military, belonged to the local VFW, and was healthy. A mom who worked part-time cooked regular meals and kept her boys in line.
His mother worked part-time at a poultry plant that supplied chicken dinners for the airlines. She was a pretty woman; his father’s friends would flirt with her whenever they visited. Even her four brothers-in-law would tease her about their fantasies for her.
Standing before Jason at the door was a beautiful young woman who looked like his mother. She had jet black hair, large brown eyes, ample breast, and a beautiful body that most men would drool over.
“Is Theresa home?” the girl asked. Theresa was his mother’s name.
“Mom, it’s for you,” Jason shouted.
“Who is it?” my mother shouted back.
“Tell her it’s Philomena.”
At this point, I will move the story along. Jason knew his mother had been married before. What he did not realize was that he had a nineteen-year-old stepsister. A beautiful stepsister. Jason was not interested in why he had never heard about her; he did not care. He had one thing on his mind.
How could he get his new, sexy stepsister in bed? Getting her pregnant was not on his mind.
Jason asked Phil (nickname for Philomena) if she would take a walk around the village with him. The road around the town was about a two-mile circle. The village was made up of mill houses. Mill houses were built by the local cotton mills in the eighteen hundreds for the mill workers to live in. The mills would deduct the rent from the worker’s paychecks. There were four family homes, each having two floors: three bedrooms upstairs, a kitchen and living room downstairs, and a basement. The mills were slowing down, the houses had been sold, but most rentals.
The village was made up of two sections, the old village, and the new village. Just a designation to differentiate the sections.
Most of his friends lived in the new village. He wanted to hear what his friends would say when they saw him with Phil.
She said she would like to walk with him. They started their walk. Jason grabbed her hand and asked if they could hold hands.
“Let my friends think we are going out,” he said as he looked her up and down. Even her legs were sexy. Outdoors he was able to get a better look at her ass. It looked round and firm. He wondered if he was dreaming or if she walked out of one of the magazines he kept hidden under his mattress.
They made small talk as he watched the faces of his friends, seeing them together. He knew it would not take long for the stories to spread around the village.
Philomena had moved in with a married friend of hers. Her friend’s name was Virginia. Virginia had two small children. She was older than Phil, about fifteen years older. She had red hair, green eyes, and a shapely body.
Phil asked if Jason would babysit while she, Virginia, and her husband went clubbing. He told her he would.
Phil picked Jason up at six pm that Friday. Both Phil and Virgie showed some cleavage in the dresses they wore. Did I mention Jason was sixteen, naturally horny, and always ready? Thinking about his newly found stepsister sexually had not decreased in intensity. Seeing both women this night only increased his forbidden desires—a woman who could be his mother and a stepsister who looked like his mother.
Jason was sitting on the couch watching tv when they arrived back home at about ten pm. Virginia and her husband went to bed. Phil came and stretched across his lap, her head on his legs.
“I hope you don’t mind,” she spoke.
“Not at all,” he said, wondering if she minded the hard-on he was developing. Jason did not know what to do with his hands, so he put one on her hip, the other on her shoulder.
“Mmm, that feels nice!” Phil whispered. She grabbed his hand from her hip and held it near her stomach.
“I did not know I had such a handsome step-brother with sexy blue eyes.” She blurted out.
His mother’s friends would always tell him how handsome he looked. He never took them seriously; that’s what most older women said to younger boys. He had started working on a cow farm at thirteen, so he knew he was in pretty good shape. At that point in his life, he had six-pack abs and a stomach of steel.
“I did not know I had such a beautiful step-sister,” he responded.
“Sit there; I will be right back,” Phil said as she got up and went upstairs.
What was she going to do, he wondered? She looked so amazing, his hormones were raging, and his mind began to play out some scenarios, all of them seeming like fantasies. That is until Phil came back downstairs.
“How do I look,” she said with a big smile.
Jason was utterly lost for words. He had never seen a real woman’s nearly naked body outside magazines. She was wearing a blue nightie with a blue bow that hung between her breasts. The top could barely hold her rather large round breast. A see-through lace body was below the breast line, which showed her perfectly round belly button. The length went just below her hips, revealing her perfectly shaped legs. Under the nightie, she wore a matching blue G-string.
“Wow,” was the only word he could get out. Jason stood to his feet. Everything after that seemed like instinct. He was about to learn more this night than in all his school years. He pulled her against him. Jason wanted her to feel his throbbing, hard cock. He wanted to feel her sexy hot body. He placed his lips on his stepsister’s lips. She opened her mouth slightly and slid her tongue through to his lips until their tongues explored each other’s mouths. He cupped one hand over her right breast and felt how firm and heavy they were.
“Not here,” she whispered in his ear. Phil grabbed his hand in hers and led me up the stairs to her bedroom.
Jason was about to lose his virginity. That is, if he could prevent himself from cumming in his pants.
They entered the bedroom. The newly found stepsister, Phil, turned to him and pulled off his shirt. She ran her fingers over his chest and down his stomach to his belt. She unhooked Jason’s belt, dropped his pants, then, with one hand, reached down into his underwear.
“How nice,” she remarked. “Have you ever fucked a girl before?” she said.
“No!” he said, embarrassed about the question.
“You will tonight; you will fuck me tonight,” she replied while removing her nightie.
Jason had only seen a woman’s breast in a magazine; this was reality. They were beautiful to look at. Large round breast, large areola, and pert pink nipples.
Phil was a lot more experienced than Jason. There is a lot to be said about experience.
Jason wasted no time latching his mouth to her nipples and sucking as hard as possible. He felt them grow harder and longer in his mouth. As he sucked and pulled on her nipples, he caressed her breast.
“Bite on them,” she said, panting. “Bite on the nipples; that gets me excited.
Jason bit on them gently and pulled the nipples with his teeth. He was having a hard time trying not to cum, too early.
Phil took one of his hands and guided it inside the fabric covering her pussy. Her skin felt warm; she shaved her pussy.
“Go ahead, feel my pussy, feel how wet I am,” she said in a broken voice.
He pushed two fingers between her pussy lips into her honey hole. She was wet, very wet.
They kissed; the more they kissed, the hotter he felt. The temperature must have gone up ten degrees.
“That feels so good. Let me lie on the bed so you can suck on my clit and put your cock into me,” Philomena said, breathing hard.
She lay in the middle of the bed, grabbed her knees, and pulled them back to open her pink, wet pussy. Above her honey hole, it looked like a little cock peeking out of its bonnet. Again instinct led him to suck on her clit. His cock was aching to enter her.
“Shit, are you sure you have never done this before? You’re driving me crazy! Get up here, kiss me and put that hard cock into me! She exclaimed, panting heavily.
I guess passion makes up for lack of experience, Jason thought to himself. He moved to her lips, kissing her belly button and breast on the way up. Their lips again met, and their tongues were on top of each other. She held her knees up while guiding his cock to her clit.
“Let me rub your cock on my clit,” she panted. Phil pressed his cock on top of her clit as he moved his hips, sliding his cock over her little penis-like clit.
She then pushed his cock to her wet love hole. “Now I want you to put your cock in and fuck me hard,” she said.
Jason rammed his cock into her, into his stepsister. He was holding off cumming, by trying to think of other things.
“You are deep, my God; I cannot believe you haven’t fucked before this,” Phil screamed. “Trust me; this will not be the last time.”
Every thrust into her brought him closer to climax. All his trying to postpone orgasm was fading, and the heat and passion of the moment was winning.
Her body started shaking; her breath was warm on his face.
“I am going to cum,” she whispered. “Can you cum with me? Cum inside me, push your cock in, and hold it there.” Phil’s breathing was hefty now.
Jason made one last thrust. His cock was buried inside her. He felt warmth around his cock as she came all over it. He cried out, “I am cumming now.” He felt the cream rising in his cock. His balls tightened. His cum burst loose into her. One, two, three large squirts of cum. He did not want to remove his cock from this sweet stepsister. He laid on top of her. He was kissing her neck, cheeks, and lips.
“That was amazing; you are so damn sexy!” he told her as he moved to her side.
“Stay with me tonight.” I will want you to fuck me again, hold me for now. Virginia would want to fuck you with me. Would you like that?” She blurted out.
“What will her husband say?” Jason felt nervous about Virginia joining them, not that he did not want to fuck her also, but that her husband might find out.
“He already fucked me. They have an agreement,” Phil said.
Jason was about to have a new experience added to his sexual diary.
