*I haven't had time to post anything in quite a while. This is a short one and could possibly have multiple parts if it is received well. As always, all characters are at least 18 and never had a sexual thought in their lives until their 18th birthdays.*
Jill Jefferson had just turned 18 a few months previously. She was due to graduate from high school in a month and was planning on taking summer classes at the local college. She was a self-styled, unapologetic, nerd. She read constantly and, even when they had gone out to her favorite restaurant to celebrate her birthday she had taken along her beloved Kindle to read.
Jill's family consisted of her 20 year-old brother, Jimmy, her 25 year-old brother, Joshua, and her parents, Lilly and Keith. Jimmy still lived at home and was enrolled in college. Joshua, however, had a good job as a computer programmer and had already bought his own home.
Jill was cute and knew it. She was a 5-6 blonde with brown eyes and a shapely figure. Her straight blonde hair was cut short and framed her pretty face. Her breasts were a B-cup and she sincerely hoped they didn't get any larger. She liked them exactly the way they were. In fact, she liked her body exactly the way it was. She exercised daily, usually taking a casual 2 or 3 mile run while listening to an audiobook. She was careful with her diet and only occasionally splurged for sweets.
Even though Jill knew she was smart and knew she was at least passably pretty, she never outwardly showed any sign of being egotistical. Most of the guys that she dated were nerds, like her. Dates were usually spent at a local "Trivia Night" at a restaurant or at the Jeffersons' house watching something on PBS. She'd only been kissed a few times and none of her dates had ever tried anything sexual with her. She wasn't even sure how much she would allow, should a boy try anything of that nature.
This isn't to say that Jill was naive when it came to the topic of sex. She knew how to bring herself to orgasm and did every few days. Recently, she had taken to standing in front of the mirror, admiring her own perfectly formed and maintained teenage body, imagining what some boy or man might think if he were to see her naked. Would he become aroused? Would he want to touch her? Would he want to kiss her breasts?
These thoughts often made her virgin pussy wet and made her want to lay on her bed and bring herself to orgasm. There were people she knew, that were very attractive to her, but she didn't allow herself to have more than very fleeting naughty thoughts about them, even though she was tempted to do so. Teachers at school, the preacher at her church, married men, and even some of the very handsome men in her own family. She knew it was sinful to have such thoughts about these people, so she forced herself to concentrate on some handsome boy at school or, perhaps, a faceless, nameless stranger that she only imagined.
Keith and Lilly, Jill's parents, had always taken then to church and had taught them that sex was only to be between a man and a woman who were married. Jill, so far at least, had never been tempted to do anything sexual with anyone. Masturbation satisfied her, although she often wondered what it would be like to have a boy or man touch her most private places.
Jimmy, her brother, was still a virgin at age 20. It wasn't necessarily by choice. He knew that, given the chance, he would eagerly participate in any sexual activity that a girl allowed. He was very picky about whom he dated, however. His parents had instilled in him to only date girls that he would potentially marry. They had to be good girls with good morals. He bought into that and had dated some very pretty girls, but, because they really were good girls, his attempts at doing more than kissing were repulsed. He often went home after a date and stroked himself off.
Like Jill, Jimmy was pleased with his own appearance. He was over 6 feet tall, slender, but with a muscular chest from lifting weights. He knew that girls and women thought he was handsome and this pleased him tremendously, but he wondered what these girls and women would think if they could see what he was packing. He knew from seeing other boys in the locker room that he was hung better than any of them. He liked to get his penis hard and admire it. It was very thick and it was extremely long -- he had measured 9 inches from his body to the tip when he was fully aroused. He loved how it looked and imagined that girls might like it, too. He wondered if it would be difficult to get it inside a woman, but he reasoned that if women could have babies that they could accommodate him.
Jimmy loved looking at and playing with his cock. He sometimes masturbated 2 or 3 times a day and every time he spurted out an amazing load of cum. He wondered if that was normal, so he looked it up and decided that it was highly abnormal to cum that much. Sometimes he would purposely not get himself off for several days, just to see how much he could produce. He amazed himself at the prodigious amounts and the distance that it shot out. There were times when he was laying on his bed to stroke that, when he ejaculated, a stream would hit the headboard above his head. It often hit his face. He always kept handkerchiefs or wash cloths within reach, should he decide to take matters into his hands in the middle of the night.
Jill and Jimmy slept upstairs. They each had a bedroom, and the rooms were joined by a "Jack and Jill" bathroom, which they called, of course, a "Jim and Jill" bathroom. Jill was always very careful to lock her door, not wishing her older brother to invade her privacy or to see something that a brother should not see. Jimmy did lock the door that went to her room from the bathroom when he was in there, but he rarely bothered to lock the door that led from the bathroom to his bedroom. He would close the door and assumed that his sister would never open the door without knocking.
Jimmy didn't have the qualms that his little sister had. When he masturbated or fantasized, anyone was fair game. He didn't care if they were married, he didn't care if they were teachers, and he didn't care if they were in the family. After all, it was just fantasy. He had taken note of how shapely his mother was and gawked at her when she wore a bikini. He had later stroked off, thinking about her hot, forty-something year-old body.
The object of his fascination, recently at least, had been his gorgeous little sister. He took every opportunity to try to spy on her but was always frustrated. The most he ever saw was a glimpse of her panties when she was brushing her teeth and was dressed in a t-shirt for bed. He imagined that he could see the outlines of her naked breasts through the t-shirt material. This sent him straight to his room to stroke out a massive cum-load in her honor.
One night, Jimmy had a date with Allison, a girl that he had been out with a few times and who attended the same church as did the Jefferson family. Allison was a very tall, blue-eyed brunette. She had been a basketball player in high school, so was in extremely good shape. This night she wore a skirt that came several inches above her knees. It was tight in all the right places, showing off her shapely ass and hugging her ample breasts. She was almost breathtaking to Jimmy. He found it hard to believe that a girl this hot would even go out with him.
They went to a movie and, shortly into the movie, Allison reached and took his hand, idly stroking it as the movie progressed. When Jimmy would look over at her, she smiled, showing off her perfectly straight and very-white teeth. She was just unbelievable! Jimmy longed to kiss her and hold her and feel of that magnificent body. He longed to peel that dress off of her and feast his eyes on her young curves. He realized that his cock was as hard as a rock and sought to think of something else so it would not be so prominent when he had to stand to leave the theatre.
Allison held his hand as they left, walking toward his car. "Want to go to my house?" she asked. "Mama and Daddy are gone all night."
Jimmy's cock lurched. Just the thought of being alone with Allison made him so horny that he could barely think. "Sure, if it's ok!"
"They'll never know. Besides, we are adults, Jimmy. We're 20 years old. We're not children anymore. Right?"
Jimmy thought back on previous dates with Allison. She was always eager to kiss, which was amazing, but once he had tried to insert his tongue into her mouth and she had pushed him away. Another time he had kissed her neck, intoxicated by the smell of her long, straight, dark hair. Again, she had gently pushed him away. Yet another time, when they were kissing, he endeavored to lay his hand on her breast. She jerked away and said, "Jimmy! I'm a good girl! Do you do this with other girls?" Jimmy had apologized profusely.
When they entered the house, Allison told Jimmy that he was welcome to use the guest bathroom while she went upstairs to "freshen up". Jimmy took advantage of the opportunity then returned to the living room and sat on the couch.
Presently, Allison appeared, having donned a pair of extremely short and extremely tight shorts and a cropped t-shirt that revealed her very flat tummy and, he imagined, almost showed the undersides of her breasts. Her very thin cotton shorts looked like the kind that his adorable little sister had worn for bed when she was younger. To Jimmy, it looked almost like she was only wearing a pair of panties. The thought went through Jimmy's head that, if Allison was trying to look sexy for him, she certainly had accomplished her mission. He couldn't believe his eyes as she flopped down next to him on the couch, grabbed the remote, and turned the TV on. Jimmy sat, as if mesmerized. He was afraid that, whatever he did, it would be construed as too overt and might ruin the moment.
"What's the matter, Jimmy? You feel ok?"
"Allison... I'm going to be honest, ok? You... you're the most beautiful girl I've ever been out with and I'm just... I'm afraid I'm going to do something wrong..."
"Oh, Jimmy, that is so sweet! Relax. Want to spoon?" she whispered as she lay down on the sofa, motioning him to lay behind her.
Jimmy complied but had no idea what to do with his hands. Allison grabbed the hand that was nearer her face and kissed it then just held it. He finally let the other hand rest on her naked side; he imagined that a few scant inches higher and he would be touching her breast. His cock was so hard that he was afraid she might push back against it and there was no way in the world that she wouldn't realize that he had an erection.
Suddenly, she flipped around to face him. He caught a glimpse of the underside of one of her breasts as she flipped over. He was overwhelmed with the urge to just lift her tiny little crop-top.
She giggled, adorably and cupped his face in her hands. "You're so handsome, Jimmy," she gasped. Then she kissed him. He placed a hand loosely on the back of her head and kissed her back. He could feel precum leaking out the head of his cock and almost wished he was home so he could relieve his aching balls. He couldn't remember ever being as turned on. This unbelievably beautiful girl was almost naked, laying on the couch with him and kissing him.
