Gender: Female Age: 19 Location: Jamestown, New York
|Introduction: This story is about a girl who learns the pleasure of masturbation from her best friend while at a sleepover.|
Everyone discovers the art of masturbation in different ways and at different times. Most start in their early teen years. Ashley, a pretty, smart, and talented teenage girl, was quite caught up in this habit.
Ashley was different that most girls; she was never as sexually inclined as early as the other girls her age. She knew what sex was and she knew that it felt good, but she never put enough thought in to realize that she could do it on her own. It took the help of a friend for her to find out. She had medium length brown hair, and slender body, and would often get a tan from a tanning bed. Her breasts were large enough to snuggly fit a smaller C cup bra.
Ashley had a good looking body, but she never talked about sex or anything like that, simply because she had never learned the powerfulness of an orgasm until ninth grade. She was also embarrassed of what other people might think of her.
Hailey was a friend of Ashley’s. Likewise, she was a cute brunette with small, but cute breasts, a slim body, and a rounded ass. When they were in the eighth grade, they met because they shared their Algebra class together. They sat next to each other in class and eventually became friends. They learned to help each other out when they were having trouble with a certain problem.
Later, in the ninth grade, they were also in one class together, which was Biology. They did not sit together, but when the class did an assignment that allowed for partners, they were sure to work together.
Hailey was also taking Chemistry that year, while Ashley was taking a second course in Algebra. Ashley was good at Chemistry, and Hailey was good at Algebra. This caused them to come over to each other’s houses to help each other with their work.
In January of their freshman year, they planned to have a sleepover one Friday night. It took place at Ashley’s house, which was smaller that Hailey’s because Ashley only lived with her mother. Hailey came from a family of six, which was difficult sometimes because she was the oldest at 14. Hailey enjoyed coming to Ashley’s house because it was more quiet and relaxing.
Ashley’s mom, Marie, took both the girls home after school was out. They arrived at Ashley’s house and began to work on their homework. They helped each other with their problems until they were sick of it.
After about 45 minutes of schoolwork, Marie offered to take the girls to a restaurant for dinner. They got back in the car, and went down the street to a local seafood restaurant. Ashley ordered a fish platter, while Marie and Hailey both ordered a shrimp platter.
On the way home, Hailey thanked Marie for dinner, and the two girls went up to Ashley’s room, which was where they were going to sleep.
“Where do you want to sleep?” Ashley asked Hailey.
“I think it’ll be fine if we both sleep on the floor next to each other,” replied Hailey.
So, Ashley set out some pillows and blankets for them to use later in the night. Then, they both sat on the futon that was folded into a couch and turned on the television. They watched a variety of shows; whenever one was over, they moved to the next channel. Throughout the time they were watching television, the sun had set.
The final thing they came upon and watched happened to be “The Wizard or Oz.” They were laughing at how unreal the movie was.
When the movie ended, Ashley exclaimed, “I think we should go to bed now,” for they had watched quite a few movies and time had passed quickly.
Hailey agreed; they both took turns using the bathroom to change into their night attire. Ashley went into the bathroom first. She took off her clothes she had worn that day, and tossed them in a basket that contained dirty clothes. She put on an old t-shirt and some shorts that went down four inches from her waist.
When Ashley exited the bathroom, Hailey went in, took her clothes off, put on the same type of shirt as Ashley, and some long pajama pants that were thin and made of cotton.
Hailey returned to the bedroom, and Ashley was sitting on the floor where they were planning to sleep. They kept the light on for a while, chatting about random things. At one point, the conversation was centered on television shows, and then later, it was focused on the hottest girl in school.
They both decided it was time to go to sleep. It was nearing midnight, and the girls were tired. They laid under their covers and listened to the crickets outside. Ashley was having a tough time going to sleep because she was not used to sleeping on the floor.
She laid there a while trying to go to sleep. She was still, which gave the allusion she was asleep. Ashley noticed that Hailey was facing away from her, laying on her right side. At first, she thought she was asleep. But, she noticed that her left elbow was moving in an eccentric way.
Ashley did not understand masturbation at this point, so she did not know what was going on. She looked over at her trying to see if she was awake. There was also a streetlight outside Ashley’s window that allowed some light into her room at night.
Ashley continued to watch Hailey until she finally asked her. Ashley did not know what she was doing, so she was not embarrassed to ask.
“What are you doing,” asked Ashley.
Hailey jumped shocked. She did not know that Ashley was awake and watching her. Hailey was at a loss for word; she could only mumble out, “Umm, nothing; go back to sleep.”
Ashley would not settle for a lie, so she again asked oblivious to what she was asking.
Hailey turned to Ashley and said, “Don’t you know?”
“No,” Ashley said innocently.
Hailey thought she was being ignorant, so she said, “I’m just making myself feel better, that’s all.”
Ashley continued to stare at her with a vacuous face.
“Do you really not know what masturbation is?” asked Hailey.
“No,” replied Ashley
“Ha, you have got to be kidding me on. I will teach you if you promise not to tell anyone. Deal?” exclaimed Hailey.
Ashley agreed, not knowing what she had gotten herself into.
“Now, take off your clothes,” said Hailey
“What?” replied Ashley. “What does that have to do with anything?”
“Just trust me on this, okay?” replied Hailey while she went to the corner of the room to turn a small lamp on.
So, Ashley did what Haley told her. Hailey also joined in and took her clothes off. Ashley was nervous, but at the same time, felt something that she had never felt before. She was actually willing to do this.
Ashley stared at Hailey as she pulled her shirt off, which let her small, but cute breasts come into view. Then, Hailey pulled her bottoms off, and Ashley could see her tight, shaved vagina.
Likewise, Hailey watched as Ashley stripped. Her breasts were larger that Hailey’s; she was captivated by the beauty of her body. Ashley pulled off her pants and panties, and saw that she had pretty vagina that was unshaved.
They stared at each other for a while observing each other’s body. Then, Hailey said, “So if you want me to teach you how to masturbate, you’d better follow my lead. Take two of your fingers, and stick them in your pussy. Then, slowly begin to move them in and out.”
Ashley did what Hailey said. She still felt very compromising, but at the same time, she was feeling excitement. She continued to move her fingers. She noticed that wetness was growing. She had felt this before, but she had never put any thought into it.
The girls remained silent most of the time they were doing this. Hailey was enjoying herself; she was still admiring Ashley’s body while rubbing her own. Ashley on the other hand, was experiencing something new.
Ashley began to accelerate her finger motion. Hailey could tell that Ashley was feeling the pleasure that came along with masturbation. Hailey herself could feel the orgasm coming closer.
“This feels kind of good,” Ashley said. “That’s what it is supposed to feel like. Keep doing it and it will feel even better,” replied Hailey.
Hailey continued fingering her pussy until she felt like she was about to go over the edge. She took a deep breath, squeezed her legs together, closed her eyes, and let out a soft moan, and then another.
Ashley stopped for a second and asked, “What was that about?”
Hailey replied, “Just continue what you are doing and you will find out.”
For a few more minutes, Ashley fingered herself as Hailey watched. Then, Ashley began to feel something building up inside her body. It felt good, but she did not know what was about to come. Suddenly, she felt a waive of pleasure go over her body. From her toes to her shoulders, she could feel her muscles contract. She was breathing hard; her legs were shaking. Hailey watched the whole thing in awe.
Ashley had not know what had happened, but she knew she liked it. She said, “What was that, it felt really weird, but really good.”
Hailey replied, “That was an orgasm. It’s what happens at the height of sexual pleasure.”
As Ashley gathered her thoughts back, she said that she enjoyed it. Hailey got up and turned the light off in the corner of the room. The girls got back under their covers, without putting their clothes back on.
Now that Ashley was more comfortable in front of Hailey, they did this many times when they were having sleepovers.
The following night when Ashley was alone in her bed, she tried again. She pulled all her clothes off and achieved the same exact feeling she had felt the night before with Hailey.
From now on, she was hooked on this habit that many teens seem to have. Almost every night, she laid on her bed naked and masturbated. She was grateful to have a friend that could teach her such a thing,
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