Virgins

Virgins

Time Watson


Chapter 1 – Jake & Miley


It was a warm Friday night in California and Jake and Oliver were waiting for Miley and Lilly to arrive. It was movie night, and like every Friday for the past couple of months they all met at Jakes house (he had the nicest home theater system). They spent the night in their pajama pants and comfortable shirts watching movies, playing games, and of course, gossiping about the latest happenings at their Middle School. These movie nights were pretty much always the same, but this particular Friday was different. Jake’s parents were out of town until morning, and that meant that they would have the whole house to themselves. It is for this reason that Jake decided that he was finally going to make his move on Miley.

It was no secret that Jake and Miley had huge crushes on each other. They were not shy when it came to flirting in public. Jake liked her because she treated him like a normal person. Everyone else treated him like a movie star. The more Miley teased him with gentle touches and naughty looks the more he became obsessed with her. She had rapidly become the focus of all his fantasies and wet dreams.

Miley despised Jake at first. She thought he was just another arrogant spoiled movie star. But then Jake opened up to her and explained how he sometimes wished that he could live his life like a normal kid. She immediately related to him from her experiences as Hannah Montana. That was the reason why she had to keep her real identity a secret. After that she not only fell for Jake Ryan, she fell hard.

The doorbell rang and Jake went to open the door. When he opened it Lilly ran in screaming.

“Wahoo, we got the entire house to ourselves!” Lilly exclaimed excitedly. “Hey Oliver catch!” Lilly threw a Nerf football to Oliver who caught it. To Lilly an unsupervised evening meant that she could finally play ball in the house.

Miley walked in wearing a cute white cotton shirt with a small strawberry on it and red and white cotton pajama pants. Miley slipped off her shoes before stepping onto the nice carpet.

“Hi Miley, you look great tonight,” Jake said honestly.

“Thanks Jake, you look hot too,” Miley said grinning before walking past him. His eyes followed her ass until she sat down on the couch. An empty house obviously meant something different to Miley than Lilly.

Oh yeah, it’s going to be tonight, Jake thought as he quickly joined Miley on the couch.

“Oaken has the ball, he drops back, looks down field, he sees Truscott open, he pump fakes to his left then launches it down field!” Oliver recites before throwing the ball to Lilly.

“Truscott catches the football and is running for the touchdown, she only has to get by one more defender to win the game!”

Lilly ran with the football toward Oliver. She was a little to slow making her move to get past him, and Oliver wrapped his arms around her, lifted her up, and tackled her onto an empty couch. Lilly landed with an “eep.”

“Dang Oliver, when did you get so strong?” Lilly asked in surprise.

“I’ve been working out, impressed.” Oliver said smiling down at Lilly before getting up and offering his hand. Lilly took it and he pulled her up. For the next hour they ate ice cream and gossiped. After which they decided to start their movie. They dimmed all the lights down and Jake started the movie.

Jake sat back down next to Miley on one couch, and Oliver and Lilly were left on the other one. It was not long into the movie when Jake made his move. He scooted closer to Miley and smoothly put his arm around her. Then innocently pulled a blanket over their legs. Miley’s heart began to beat faster. The heat from his body made her feel excited and calm at the same time. Then she rested her head against his. Jake was excited that his embrace was well received. He pulled his head away from hers. When she looked at him questioningly he moved his head in and kissed her soft lips. Jake and Miley felt their whole bodies burning up and tingling with delight. Their heart rates seemed to double the second their lips touched. Miley let out a soft moan; she never thought kissing would be this intense. The inexperienced kissers started out slow, but to Jakes surprise it was Miley who made the first efforts to carry it forward. Miley slowly opened her mouth cueing Jake to do the same. Their tongues just barely peaked out of their lips like a young cub fearing to leave its mother’s den. Their heads became light as they clumsily stumbled through their first real kiss.

Jake’s boldness hit first. When he felt Miley part her lips a bit more he slipped his tongue into her mouth. Miley moaned at the sensation. Jake found her tongue and slowly started to massage it with his, causing Miley’s head to swim. Miley slowly opened her mouth to give him more access to her. Her soft moans drew more frequent and her heart pounded in her chest. Jake slowly started to withdrawal his tongue from her mouth, but as he did so he felt her tongue follow his. Jake withdrew his tongue all the way back, and he felt Miley slip her tongue into his mouth in pursuit. Miley placed her arms around his neck and deepened the kiss. Miley felt the heat and excitement from the kiss traveling down and centering itself in her most intimate region. She felt herself getting wetter and wetter as the heat started building and building between her legs. Her whole body started squirming in synchronation with the kiss. Jake sensed Miley’s needs, and felt his own pressing firmly against his pants. Jake pulled the blanked over their heads to give them more privacy.

Jake started to feel more confident as they got better and better at kissing. Miley was really into him and she began to explore his body with her hands. She slipped her hands underneath his shirt and felt the lean muscular body of the world’s cutest teenage heartthrob. Jake loved her hands on his body. Every spot she touched burned and tingled with delight. Miley removed her hand from under his shirt and began to message his thighs, getting real close to touching the dragon that she had awoken within his pants. As she rubbed his thigh Miley would “accidentally” slide her hand up too high making contact with Jake’s hard-on poking into his pajama pant leg. The “accidental” contact was causing it to jolt every time. Miley loved touching his body, but there was one particular thing that Miley wanted to touch more than any other. She had wanted to touch a guy’s penis ever since she was twelve. Two years of curiosity grew and now she was particularly interested in this boy’s nether parts. Just as these thoughts were flooding through her head, and her “accidental” touching was becoming far more frequent, they both heard the sliding door open and close. The noise could only mean one thing; Oliver and Lilly had gone outside leaving the whole house to themselves.

The added privacy and the frequency of Miley’s “accidental” brushes over his hard-on made it silly for her to pretend that she didn’t want to touch it. This time Miley slid her hand up until it was on top of his hardness. Miley began groping and rubbing Jake’s equipment through his thin cotton pants with excitement and curiosity. Jake placed both hands in her silky hair and moaned into Miley’s mouth as their kissing continued. This was the first time a girl has ever felt him up like this, and it sent fire racing through his body. Jake’s cock became so hard that it was almost painful, and his tender balls began aching as Miley even began reaching for them.

If Miley wasn’t holding back anymore, than Jake didn’t see any reason why he should hold back either. He tossed the blanket onto the floor confirming that Oliver and Lilly had indeed left the room leaving him and Miley in absolute privacy. Excitement flooded through him as he debated what he wanted to touch first. Jake slid his hands down her hair and cupped her breasts causing Miley to moan into his mouth. They felt just as perky and responsive as they looked.

Miley moaned openly into Jakes mouth as his eager hands squeezed and rubbed her newly formed sensitive breasts. Miley felt a wonderful feeling course through her body. Pleasure rushed and focused itself between her legs making her get really wet and horny. The pleasure between her legs was building in greater and greater amounts. Her pussy was getting wetter and wetter and began begging for attention.

Miley couldn’t take it anymore. She removed her hands from Jake’s pants and placed one hand around the back of Jack’s neck and deepened the kiss. With the other hand she reached below the waistband of her pajama bottoms and began to rub herself. Her pussy felt hotter, wetter, and more swollen than she had ever felt it before. It was so sensitive; her whole body felt like it was on fire.

Suddenly Jake became aware that their kiss kept breaking off so Miley could moan in ecstasy. At first he thought it was from his attention to her breasts, but when he glanced down during one of Miley’s moans he was surprised to see the girl of his fantasies pleasure herself right in front of him. A huge lump developed in his throat. Jake continued to rub her breasts and kiss her in-between her moans of pleasure, but he wanted to do more. He reached out, grabbed her wrist, and slowly pulled her hand out of her pants. It was soaked with her juices, but his inexperience denied him the motivation to taste her. Instead he slipped his hand underneath the waistband of her pajama bottoms until his fingers become drenched when they made contact with her soft warm pussy.

Miley moaned out and spasmed from the pleasure that went coursing through her virgin body as her most private and sensitive spot was touched by a boy for the first time. Jake had no idea what he was doing, but he began rubbing the delicate skin with care and excitement. He ran his fingers deeper into her folds as he searched for her opening. He felt even greater wetness and heat underneath her folds. As he traveled upward he felt a hard nub underneath a soft hood. He must be doing something right because Miley closed her eyes and her legs began trembling as he rubbed it. Miley was forced to break the kiss. Her breathing was becoming more labored and her face contorted with pleasure as she tried to control her volume.

It must be really intense Jake thought, because this was the first time Miley stopped kissing him. She was completely absorbed in what he was doing to her. Jake lowered his fingers through her folds as he went back to searching for her entrance. As his fingers traveled down he felt his middle finger accidentally slipping into her body. The pleasure of being fingered for the first time caused Miley to take in a sharp intake of breath and let out a small scream.

Miley’s small entrance was so slick, tight and warm. Jake’s cock lurched in his pants. He imagined what it would be like to have his hard sensitive cock inside her experiencing the heat and wetness that his finger was feeling. Then Jake slowly started to move his finger around inside her.

Miley looked at Jake with all the lust in the world, the feeling of his finger moving inside her was unbelievable. It was like nothing she had ever felt before. Miley began to get sweaty and her whole body started shaking.

Miley saw Jake’s cock lurching upward from what he was doing to her. Miley immediately reached into Jake’s cotton pajama pants and pulled his cock out into the open. Then she slowly started sliding her soft hand up and down it. Jake moaned at the sensation of Miley’s hand wrapped around his exposed cock. Miley loved it; it was so hard, but soft at the same time. Jake felt his whole body tense with pleasure. This was the most incredible thing he ever felt, and he knew that he wasn’t going to be able to last that long.

The sudden urgency drove Jake’s ambition to stick another finger in Miley. He wanted to do everything in his power to make Miley cum first. Jake gently slipped another finger inside her tight pussy causing Miley to arch her back and moan loudly. His two fingers barely fit inside her. Jake couldn’t move them around so he started to slide his fingers in and out of her slick hot pussy instead. Miley moaned and panted uncontrollably from the friction his fingers made against her sensitive walls. She felt an amazing pressure, like nothing she had ever felt before, building up deep inside her core. Miley returned the favor by stroking his cock faster.

As Jake felt himself quickly approaching his orgasm he responded by increasing the speed of his fingers, which caused Miley to subconsciously increase the speed of her stokes on his cock. Their hearts were beating frantically in their chests. Their entire bodies felt like they were burning with pleasure, and their mouths hung open for air. Their eyes were alight with desire and lust as they raced toward their nearing orgasms. The quiet room was filled with the noise of heavy breathing and moans of two young innocent teenagers experimenting with true pleasure for the first time.

Jake and Miley were squirming, panting, and moaning like animals. Jake felt a familiar pressure building up below, except this time it was much stronger. Their was no stopping it, in a few more seconds he was going to cum. Then Miley suddenly took a sharp intake of breath and her whole body went ridged. Jake felt her tight pussy suddenly clamp around his fingers, and Miley screamed at the top of her lungs as her orgasm crashed through her. Her pussy squeezed and released around Jakes fingers drenching them in her cum. Jake slowly started removing his fingers from her pussy as she continued to cum and squeal with delight.

When Miley felt his fingers starting to leave her, she instinctively used both hands to grab hold of his wrist to keep him inside her while she came. Jake watched in amazement as Miley shut her eyes and arched her body. Miley’s entire body shook and spasmed as it released her cum around his fingers. He did not fight Miley’s hands, and kept his fingers buried inside her as he rode her through her first real orgasm. After about a good solid minute of cumming Miley started to gain control of her body. Jake felt her pussy start to calm down around his fingers and her cumming started to subside. Miley rode through the last gentle seconds of her orgasm and released Jakes wrist in exhaustion. Miley threw her arms around Jakes body and hugged him. Her body was singing in absolute bliss. It was the most intense and exhausting thing she had ever experienced. Jake pulled is hand out of Miley’s pants and wrapped his arms around her as she tried to catch her breath. Jake never felt as good as he did in this moment. He felt so masculine and proud of what he was capable of doing for the prettiest girl in the world.

*CRASH!*

There was a loud crashing noise against the sliding glass door. When Jake and Miley darted their heads to see what happened they were shocked to see that Lilly and Oliver had crashed against it. Oliver had Lilly’s hands pinned above her head and they were making out like crazy.

Miley and Jake looked at each other in shock and amazement. They would have never guessed that Oliver and Lilly had harbored feelings for each other. That wasn’t the only thing that shocked them. Their kiss wasn’t anything like the gentle kissing and touching they experienced with each other. Oliver and Lilly were two wild animals having their way with one another.

Miley looked back at Jake to start gossiping about Lilly and Oliver. Then her eye caught sight of Jake’s throbbing member. The distraction had done nothing to limit his erection. Miley didn’t know what to do. She was sitting next to Jake with his hard cock out of his pants just inches away. Did he want her to start touching it again? Did he just want to make out again? Miley didn’t know what to do. She suddenly felt really awkward.

Jake saw her staring at it. He wouldn’t have been nervous, but he had a huge question on his mind. He wanted to do something, but he had no idea how Miley might react if he asked her.

“Uhm….Miley….do you want to go to my bedroom?” Jake’s heart swelled with nervousness as he asked her.

Miley immediately understood what he meant by that. He wanted to have sex with her; to loose their virginities to each other.

“yeah…um….o.k.” Miley answered nervously. There was no other person she would rather loose her virginity to than Jake Ryan.

Jake smiled and pulled her in for a long loving kiss. They both wanted to do it, but they still felt nervous. The kiss started to help ease their nerves a little, but as the kiss continued so did their desire to stop procrastinating and do it. They broke the kiss. Jake pulled his rock hard cock in his pants and stood up. Then he extended his hand and pulled Miley to her feet. Jake led her to his bedroom. The trip seemed a lot longer than usual, and they had never had to focus so much on such a simple activity as walking. After they entered the room Jake closed the door behind them. The house was empty, but anything to add to their privacy was appreciated.

Jake turned around and saw Miley standing nervously by his bed. Jake could hardly believe that the girl of his dreams was in his room waiting for him. Jake was nervous, excited, horny, and scared. He gathered all his courage and walked toward his dream girl. They nervously stood only inches away from each other.

Jake leaned forward and began kissing her. His hard erection pressed firmly against her stomach. They fumbled through the kiss. Their nerves were making it difficult. Jake grabbed the bottom of Miley’s shirt and slowly lifted it up over her head. Her shirt landed on the ground leaving nothing left to cover her upper body. Jake became enchanted by her beauty to the point that it was even hard to breathe. Blinking was not an option. Her long brown hair draped softly over her smooth unblemished skin. Her perky breasts and excited nipples looked so desirable. Jake’s cock continued to press hard against the cotton fabric in his pajamas.

After a few seconds Jake became self-aware again and wrapped his arms around her delicate body. He pulled her in for a passionate kiss. This time her naked beauty had shaken all his nerves away. He found the confidence that was built in for this very moment.

Jake roamed his hands all over her back enjoying the sensation of touching her warm velvety skin. He moved his hands around to her newly formed breasts and began to slowly massage them. They felt absolutely incredible underneath his hands. He had waited so long to do this. He was deliberately gentle as he roamed his hands over them eagerly. He made sure that he did nothing to hurt the beauty that was Miley.

Miley reached forward and began tugging at the bottom of Jakes shirt. With trembling hands Miley lifted it over his head and let it fall to the ground indicating that she really wanted to do this.

Jake’s lean body was a marvel to look at. Being a young action star had developed and toned his muscles very nicely. Also living in California and hanging out on the beaches had given his skin a light beautiful tan. Miley roamed her hands all over Jakes chest and back as they resumed their kiss. She felt his toned muscles passing under her hand causing her desire to grow every second. Miley’s hands traveled down under the waistband of Jake’s pants and she wrapped her fingers around the biggest object of her desire. As Miley played with his throbbing cock, it began making it harder and harder for Jake to concentrate on the kiss. Jake quickly pulled his hands off Miley’s body and pushed his pants down to his ankles. His manhood was once again freed into the open.

Miley was in awe of Jake’s naked form. Miley looked at him with an open mouth as she visually explored his body. Jake’s member was so hard that it was sticking strait out and throbbing as he stood there.

Jake couldn’t wait anymore. He wrapped his hands around Miley and pulled her in for a deep kiss. His naked cock pressed against her soft tight stomach. The fresh contact made both of their bodies ignite with lust. Jake ground his hard member against her smooth warm stomach as he kissed her passionately. It did not take long before they felt pre-cum start oozing out of his cock. It quickly got rubbed onto Miley’s stomach causing her stomach to become slick and glistening with it. The slick rubbing feeling was incredible causing Jake to grind against her with more intensity. Jake felt a wonderful sensation building up in his cock, and he desperately wanted to maintain the feeling. Then a sudden urge to ejaculate crashed over him. Jake was just barely able to pull away in time to stop it. He felt bad for pushing Miley away a little too hard than he meant to, but right now he had to focus.

Jake was using every ounce of will he had not cum right now. His cock was pulsing wildly and even the slightest touch at this point would set him off. Jake and Miley watched in surprise as a stream of pearly white cum oozed out from the tip of his cock and slowly dripped itself onto the floor. This was the first time Jake had actually oozed out real cum without an orgasm. Jake didn’t know what to make of it, but one thing was for sure. Seeing it happen turned them both on so much.

When Jake finally felt himself pull away from the edge he walked forward and grabbed Miley’s hand. He led her to his bed; his cock was still painfully hard. Jake pulled his covers down so that Miley could lie on the clean smooth white linens. Jake adjusted his pillow for her head and nodded to Miley. Miley climbed onto his bed and laid on her back resting her head on his soft pillow. Miley’s breathing became shallow as Jake leaned forward and pulled her pajama bottoms all the way down her legs and tossed them to the floor. Miley nervously spread her legs apart and bent her knees up in the air at 90-degree angles for him. She draped her arms undefensively at her sides. Miley began trembling slightly in a natural fear. She felt so vulnerable in this position. Miley had heard that it hurts the first time, but there wasn’t anyone else that she would rather loose her virginity to. She trusted Jake.

Jake took a moment to admire the girl of his dreams awaiting him in his bed. Jake knew that he couldn’t handle any more floor play. His cock was so sensitive right now that he knew that he had to get right to it. The soft pink folds of Miley’s opening drew his attention. Her small innocent pink pussy was slightly parted open from the spreading of her legs. It was already slightly swollen and glistening wet from earlier. Jake couldn’t wait any longer. He felt a primal pull directing him towards her. He climbed onto his bed and positioned himself on his knees between her legs. When their eyes locked they found it suddenly impossible to talk, so Jake just nodded his head and Miley nodded back.

Jack scooted forward between Miley’s smooth legs causing their hearts to pound in their chests. Then Jake carefully positioned himself at her entrance and pressed the tip of his cock into her warm wet folds. Jake and Miley felt a wonderfully hot feeling spread through their entire bodies. Jake slid his cock around as he felt for her entrance causing the hot feeling to get more intense. Miley began to squirm as her sensitive pussy was rubbed with the tip of his smooth cock. When Jake located her opening he was once again reminded how small it actually was. His natural instincts told him to be slow and gentle, and his tone body gave him good control. Jake slowly started applying more and more pressure until he felt himself starting to slide inside her.

All of Miley’s attention was drawn to it as she felt Jake pressing himself into her. Miley’s breathing became labored with pain as her virgin pussy adjusted itself to take Jake’s member inside. He was being really slow and gentle, but she knew that he still had a lot more to put inside her so she laid back watched his face. The pain only got worse as her body stretched to accommodate more and more of him. She was thankful that it was Jake, because his gentleness was the only thing keeping the pain bearable as her virginity was taken away. They both knew that the pain was going to be a passing thing, and afterwards their relationship would be perfect.

It was a slow journey but Jake kept pressing more and more of his smooth cock into Miley. It felt so warm and wet inside if her. Miley looked tense under him. Jake knew this must be hard for her as her small opening took in more and more of him. He was nearly all the way in now and it was feeling incredible. Jake felt guilty for getting so much pleasure when it was causing her so much pain. Jake slowly pressed the last inch of his cock into Miley. Her throbbing pussy was now completely wrapped tightly around his pulsating cock. Jake felt so warm and happy inside her. It was like being in a constant state of Euphoria.

The pain was coming in sharp waves. Miley felt her pussy feebly trying to squeeze out the intruder from her body. Miley knew Jake was completely inside her now and she desperately hoped that the pain would start to go away soon.

Jake rested there for a second giving Miley time to adjust while he just enjoyed being completely inside her. It felt better than he could ever have imagined. Then Jake started to slowly grind inside her, savoring the incredible feeling it generated. The grinding slowly worked her a little looser. Jake then slowly pulled his cock just and inch out of her and began fucking Miley with gentle shallow strokes. He slowly and lovingly worked his way toward longer and longer strokes. Jake felt an incredible feeling in his balls like a tight knot becoming undone.

Miley still felt tremendous pain as Jake’s cock slid in and out of her. The look on his face and the grunts he was making told her that he was really enjoying it. Miley wondered when she was going to start feeling what Jake was feeling. Then to Miley’s surprise and relief she started to feel the pain going away.

Before long Jake was fucking Miley with long complete strokes. It was the most incredible feeling he ever felt. Jake used all his will to prolong it, but he knew that he wouldn’t last much longer. As Jake felt Miley’s body get more and more used to him he started to increase his speed.

When Jake started to go faster Miley was amazed to find that all the pain was finally gone. It was a tremendous relief and her entire body immediately relaxed. Once her body relaxed Miley started to feel incredible sensations building up inside her. Miley began to breath harder, not out of pain, but toe-curling pleasure. It was the most incredible thing she ever felt and moans of ecstasy began to flow naturally out of her mouth. Her slick tight pussy was completely relaxed and begged for more of Jake’s cock. Jake’s cock continuously and rhythmically plunged itself against every sensitive nerve deep inside Miley’s body causing her to moan and squeal uncontrollably. Soon every inch of Miley’s body was singing with delight.

Jake was driven wild by the sounds Miley was making and he started fucking her faster and faster. They weren’t holding back anymore and their bodies began burning up with desire. The sweet aroma of sex filled the room. Their bodies became glistening with sweat as they cried out each other’s names. The feeling of sliding in and out of Miley over and over again was heaven. Miley wrapped her smooth legs around Jakes hips as they used their young bodies to make love to each other. All the nervousness and pain was gone; replaced by the deepest feelings of pleasure and connection they had ever felt. They could stay like this forever.

At the exact same moment Miley and Jake suddenly felt their orgasms crash through their bodies. Jake plunged himself all the way inside her warmth and burst his hot load deep inside her as Miley’s pussy contracted rapidly around his exploding cock. Their faces contorted in pleasure and they screamed out each others name. Jake shot load after load of cum inside her, while Miley burst more and more cum around his cock. It was the most intense feeling they had ever felt. Every inch of Jake’s cock and every nerve in Miley’s pussy became ultra-sensitive from the cum. Every part of their bodies were wrapped around each other as they rode threw the most intense orgasms that they would ever feel.

They moaned and thrust the last bit of cum and energy they had before collapsing into a heap. They did not have any more energy to move. With their soft warm bodies intertwined in love, they immediately fell into a blissful sleep. Miley Stewart and Jake Ryan had lost their virginities together.