Virgins

Chapter 2 – Lilly & Oliver


Lilly and Oliver were sitting on the couch watching the movie when they saw Jake scoot closer to Miley and put his arm around her. To be honest they weren’t that shocked about this. They knew they liked each other and figured that it was only a matter of time before they became an item. So they just went back to watching their movie. That was until they heard a moan from Miley. Lilly and Oliver became shocked at what they were seeing. Jake was french kissing Miley. Oliver and Lilly looked at each other in surprise as Miley and Jake’s kiss continued to deepen. Oliver and Lilly tried to ignore them by going back to watching the movie, but soon found it impossible with the sounds coming from the other couch. Lilly and Oliver looked at each other again.

“Do you think we should leave?” Oliver whispered to Lilly.

“I don’t know,” Lilly responded.

They looked over at them again. Miley had her arms around Jake, and they watched as Jake pulled the blanket over their heads.

“I think that answers our question,” Oliver whispered turning back to Lilly.

“Yeah,” Lilly responded.

Oliver and Lilly got off of the couch and opened the sliding door and shut it behind them.

They stepped onto the deck and leaned against the far rail. It was a beautiful night and they stared out into the Pacific Ocean. The stars were shining brightly and the full moon reflected off of the black ocean. In the distance the dotted lights of ships could be seen rising and falling gently with the ocean swells. The air was cool and the only sound came from the rumble of waves as they hit the shore.

“Sure is beautiful huh Lilly,” Oliver said.

“Yeah.”

There was a long silence as they stared across the ocean and thought about what they witnessed.

“They were really going at it weren’t they,” Lilly said smiling.

“Yeah,” Oliver laughed.

“Have you ever kissed a girl like that Oliver?” Lilly asked curiously.

“No,” Oliver replied surprised by the question.

“Have you ever thought about it?”

“Well…Yeah I guess.”

“Who would you want to do it with?”

“What?” Oliver replied still surprised by the line of questioning.

“C’mon don’t be shy,” Lilly teased.

“Well there is this one girl.”

“Really! Who is she?” Lilly asked excitedly.

“I….uh….I can’t say.”

“Oh come on Oliver. I won’t tell anyone,” Lilly said nudging him with her elbow.

“No, I can’t,” Oliver responded blushing.

“Well, I will just have to guess then. Hmm…lets see…, if you can’t tell me then it must be someone I know….Is it Sarah?”

“No.”

“Tiffany?”

“No.”

“Amber?”

“You’re joking.”

“Ashley?”

“C’mon Lilly.”

“Oh I know! Amber and Ashley…at the same time!” Lilly said laughing at her cleverness.

“Stop messing around Lilly. I am not going to tell you!” Oliver stated defiantly.

“Ooooh, Ooooh, I figured it out….it’s JACKSON! And that’s why you didn’t want to tell me.”

“What, c’mon Lilly stop it,” Jackson said smiling.

“I knew I was right, that’s why you’re so embarrassed, admit it Oliver!”

“Admit WHAT!”

“You’re gay!” Lilly said still teasing him.

“NO!”

“So it’s true. You just won’t admit it!”

“What…no…that’s…that’s not…stop trying to trick me!” Oliver yelled in frustration.

“Admit it! You want to kiss Jackson,” Lilly said pushing his shoulder.

“I DON’T WANT TO KISS JACKSON!......I WANT….I want you.”

“Wh……….what? Oh I get it, very funny Oliver. For a second there I thought you were being serious,” Lilly said trying to mimic a laugh.

Oliver was tired of holding back his feelings for Lilly. Then in an instant, before he could rationalize an excuse not to, he spontaneously embraced Lilly and began kissing her. Lilly’s arms hung down in shock from what was happening. Oliver kissed a surprised Lilly for a good five seconds before the initial shock wore off. Then Lilly melted into his arms. She put her arms around him and kissed him back.

Lilly suddenly realized that all these years Oliver had been crushing on her. She had never imagined that Oliver thought of her this way, and for some reason the thought of Oliver as a boyfriend never even occurred to her. But once he began kissing her it was like flipping a switch. Suddenly Lilly realized how much of a hunk Oliver was. She suddenly became extremely attracted to him and her body was responding with intense, hot, tingling sensations.

Oliver and Lilly’s kiss was driven out of hunger and quickly became as intense as the heat inside their bodies. But they needed more. Oliver instinctively walked Lilly backwards until she crashed against the sliding door causing her to whimper. Oliver broke the kiss and lifted Lilly’s hands above her head. He pinned her body against the door and with one hand and held her arms above her head by the wrists. Now she was his. Lilly could see the lust in Oliver’s eyes as he took his other hand and gently ran his thumb down her soft lips. Lilly’s heart was pounding inside her chest with an excited fear. She felt the strong heat inside her focus between her legs making her wetter than she had ever been. Lilly had no idea that Oliver had this much passion inside him.

Oliver placed his free hand on her inner thigh outside her soft pajama bottoms and began moving his hand up and down while he looked into Lilly’s eyes. God he could not believe how beautiful they were. Lilly’s heart was skipping beats and she felt her pussy quivering as it got wetter and wetter. Her legs started to feel weak and she was barely able to support her own weight.

Oliver felt a strength growing inside him. He looked deep into Lilly’s eyes. In a brief moment as he continued to stroke her inner thigh he saw a flash of crazed passion and lust pass over them and he felt her knees buckle. Oliver looked at her with all the passion and fire in the world then pushed his lips onto hers. Lilly immediately opened and Oliver plunged his tongue deep inside her mouth.

Lilly always dreamt about what her first kiss would be like. But never imagined it would be like this, or with Oliver. Lilly began to feel Oliver’s hard-on pressing against her body as he continued to assault her mouth and stroke her thigh. Oliver loved how much pleasure he was giving Lilly and wanted to give her more. He moved his hand up her thigh between her legs and continued until he made contact with her pussy. Lilly jolted and took a sharp intake of breath as Oliver pressed his hand against her most sensitive region. Lilly’s legs immediately became numb. The only thing holding her up was Oliver’s body pressing hers against the glass. Oliver began rubbing her pussy vigorously through her soft pajama bottoms.

“Aaaaaagggghhhhhhhh!!!” Lilly moaned into Oliver’s ear.

It was the most incredible feelings of pleasure Lilly had ever felt. She didn’t know feeling this good was possible. The fabric of her pajama bottoms offered only a thin barrier between her soft sensitive pussy and Oliver’s pleasuring fingers. Lilly had never felt so much wetness between her legs before in her life. She felt an endless supply of juices start to run down her legs. All the pleasure was accumulating deep inside her in greater and greater amounts. The pleasure she was receiving was mixing with her growing need for release. Lilly did her best to grind her pussy on Oliver’s hand while moaning his name into his ear.

Oliver felt her warm juices soak through her pajama bottoms onto his hand. He found that he loved pleasuring Lilly more than anything. He loved how her face contorted with pleasure and hearing her call out his name in ecstasy. He would easily sacrifice his own needs just to see her writher in pleasure.

“Oh my god Oliver….right….right….RIGHT THERE!!!” Lilly screamed.

An inadvertent shift in Oliver’s hand caused him to start rubbing directly over her clit. Lilly felt the most incredible sensations pouring through her young body. She closed her eyes and felt the pressure inside her core building its way to a great release.

Oliver pulled his head back while he continued to vigorously rub that spot. Lilly’s eyes were closed and she had a look of complete ecstasy on her face. Her mouth was open and drool was running out of the side of her mouth. The huge accumulation of pleasure that had built up in Lilly’s core felt like it was about to explode in release.

*BAAROOOOM!!!* A loud horn from an oceanic vessel was blown as it made its way to the warf.

The sudden noise ripped them from the moment and Oliver jumped back in surprise. Lilly collapsed onto the ground, her trembling legs unable to support her weight without Oliver’s body pinning her up. Oliver quickly regained his bearings and pulled Lilly to her feet and helped her stand. Her legs were wobbly and she had trouble standing. Oliver noticed that her whole body was trembling and she was breathing very hard. He led her to a soft sturdy lounge chair on the deck. Oliver laid down first and pulled her down with him so that she was laying on her back on top of him. The outdoor lounge chair had a back that was propped up 35 degrees. Oliver loved the feeling of her weight on his body. Lilly’s small bubbly ass pressed directly on his hard-on. The thin cotton fabric of their pajama bottoms offered only a small soft barrier between their bodies making them both crazy with sexual energy. Oliver put his arms around Lilly while they watched and listened to the boat docking against the warf. Lilly’s trembling was starting to subside and her breathing was beginning to return back to normal.

“That was intense,” Oliver stated after a short rest.

“Yeah,” Lilly responded through heavy breathing. “Do you want to keep going?” Lilly asked feeling Oliver’s boner pressing against her
butt.

“You don’t know how long I’ve wanted to do this,” Oliver said huskily. “I am going to make you cum so hard Lilly.”

“Eeeeeep,” Lilly squeaked as she often did when she became overexcited about something.

Then Oliver began to do something that he has dreamt of for the past year. He gently ran his hands along Lilly’s flat stomach and up to her perky breasts; which were generous for her age and body size. His cock lurched against her ass in excitement and Lilly arched her back and moaned candidly as he began to gently squeeze and fondle her young sensitive breasts. As Oliver felt her through her thin cotton shirt he realized that she wasn’t wearing a bra.

Lilly’s ass rubbed against Oliver’s dick making it even harder as she squirmed on top of him. Oliver felt her nipples harden under his eager hands. He turned his head and saw Lilly’s face contorting with pleasure. She looked so cute and her soft moans were irresistible. Oliver couldn’t retrain from nibbling on her ear as he pleasured her further. He gently bit and tugged at her earlobe and traced her ear with his tongue.

“Do you want me to rub your pussy?” Oliver whispered into her ear.

“Yeah,” Lilly breathed instinctively.

“I want you to beg for it,” Oliver grinned.

“Oliver, please rub my pussy. I’m so wet. I need it so bad,” Lilly begged in a whisper. Lilly felt like she had strayed into a dream. The whole thing seemed so surreal.

Oliver slowly slid a hand off of her breast and down onto her stomach. He left his other hand to continue to rub her breasts through her shirt. Oliver reached the bottom of her shirt, which had ridden up during his exploration of her body leaving some of her tight stomach exposed. Oliver grabbed the bottom of her shirt and pulled it up to the bottom of her breasts fully exposing her flat stomach. The cool night air felt refreshing against her warm skin. Oliver gently ran his hand over her stomach feeling her silky skin pass under his fingers. Then he slowly let his hand travel downward until the tips of his fingers just barely slid under the waistband of her pajama bottoms. Lilly arched her hips and felt a drip leave her pussy in anticipation. Oliver stopped his hand until Lilly lowered herself back onto him. Oliver felt her weight return to his body and the incredible sensation her ass squishing back down against his pulsating cock.

Then Oliver teased her by refusing to move his hand. He could tell that she needed him as her squirming got worse. This only encouraged Oliver to keep teasing her more. Her ass was doing an incredible job at pleasuring his hard cock, and it only felt better as her squirming got worse. Soon Oliver felt hot pre-cum start oozing from his hard cock onto his leg.

“Oliver, please don’t stop. I want to feel your hand on my pussy. It won’t stop dripping Oliver!” Lilly begged desperately.

It felt incredible to feel her ass rubbing his cock. Oliver thought about being selfish and refusing to heed Lilly’s begging. But she was just too damn cute and he liked her too much to deny her. Oliver let his fingers slowly travel lower under her waistband. Lilly’s core was
aching with need and anticipation. Then when the second knuckle of Oliver’s fingers disappeared under her waistband he stopped again.

His fingers were only inches away from sweet quivering pussy. Lilly began to bounce up and down on top of Oliver’s cock as she tried to close the distance between his glorious fingers and her eager pussy. Oliver kept his fingers centimeters above her begging pussy with half his attention and with his other hand he began to focus on her breasts. Oliver moved his other hand down to her tight stomach, and then back up her young warm body. This time he slid his hand under her shirt and up onto her bare breasts. Oliver couldn’t believe it, they felt incredible. They were incredibly soft and her hardened nipples pressed into his palms. Oliver abandoned the feeling just for a second so he could lift her shirt up revealing Lilly’s breasts for the first time. They looked as perfect as they felt. Cute perky breasts resting on her slender frame. Her hard sensitive nipples poking toward the starry sky in the cool night breeze. Oliver began squeezing and massaging them eagerly. He licked his lips as he played with her hard nipples. Oliver was in heaven as he played with Lilly’s breasts and felt her ass rubbing and bouncing against his cock.

Lilly loved the feeling and pleasure that she got from Oliver playing with her breasts, and loved that Oliver got so much pleasure from playing with her breasts. But right now she needed more, because having his fingers so close to her pussy was causing her juices to flow out of her non-stop.

“Oliver, please stop teasing me, I need your hand on my pussy! Please Oliver!” Lilly begged once again feeling her core aching for contact by the man whose fingers were so close.

Oliver complied and slowly moved his fingers further into her pajama bottoms until they were right above her pussy. Lilly was frozen with anticipation. Then he stopped once again and Lilly’s hips lifted of Oliver’s body once more. Her body was shaking; begging for the contact that was so close.

“OLIVER!!!!” Lilly screamed not capable of closing the distance herself and not able to bear being teased any longer.

Oliver realized that she had reached her limit so he slid his fingers forward burying them inside her hot wet folds.

“Aaaaaaahhhhhhhhhhhhhhh,” Lilly moaned when his fingers became buried in her pussy sending a shockwave of pleasure up her spine.

Lilly’s hot pussy was the softest thing Oliver had ever felt. His fingers immediately became drenched. Oliver loved the feel of Lilly’s wet folds slipping through his fingers. Oliver couldn’t believe how wet she was, even her thighs were covered in her juices. Lilly was in an absolutely uncontrollable state as her body moved with the pleasure he was giving her. Every time Oliver passed his fingers over her swollen clit her hips would jerk up in ecstasy. Her whole body was sent into a gyrating motion causing her ass to bounce and rub all over Oliver’s sensitive cock. Oliver felt more hot pre-cum start to ooze from his dick from her motions. Her ass was sending the most incredible feelings of pleasure he had ever felt through his entire body. He did his best to hold her chest down while he massaged her boobs, and tried to keep her ass pressed and rubbing against his sensitive cock as much as possible as he vigorously rubbed her pussy.

Lilly moaned Oliver’s name as his hand explored and rubbed her delicate pussy. She screamed and moaned as Oliver rubbed her pussy relentlessly and pleasured her breasts simultaneously. Lilly was getting so much pleasure from both fronts and she felt herself getting closer and closer to a tremendous climax. She felt herself bouncing and rubbing against Oliver’s hard cock uncontrollably. Thinking about and feeling Oliver’s cock under her only deepened the pleasure she felt. She felt Oliver desperately trying to hold her butt against his hard sensitive cock while he continued to drive her wild with his fingers. Then Oliver boldly slid his middle finger into her warm pussy up to the second knuckle.

“Oh God,” Lilly squeaked as her eyes rolled back into her head. Oliver was the first person to be inside her body and she was loving every moment of it.

God she was so tight Oliver thought. Oliver pressed the rest of his hand against her wet pussy and began sliding his entire hand up and down it; pulling his middle finger in and out of her tight, hot entrance as he did so. His hand was stimulating every single nerve on her pussy.

“Ooooohhh fuck Oliver…….You are amazing!” Lilly screamed out. Oliver had just made Lilly curse openly for the first time.

Lilly felt the tension in her building to a rapid peak inside her core. Her breathing became jagged and labored. Her heart was racing trying to push the pleasure she was receiving to all parts of her body. All of her muscles began contracting involuntarily and her toes curled up. Lilly grabbed onto Oliver’s arm.

“Oh my God Oliver……I think….I think I’m…….I think I’m gunna……….” Suddenly all of Lilly’s muscles tensed up,

“CUUUUUUUUUUUUUMMMMMMMMMMMMM!!!!!!!!!!!!!!!!” Lilly screamed when her entire body simultaneously released. Her eyes rolled into her head as she screamed out. A huge orgasm swept through every part of her young body. Her pussy rapidly contracted and released around Oliver’s finger sending her juices flowing from her pussy.

“OOOOOOOOHHHHHHHHH GODDDDD, OLIVERR!!” Lilly screamed so loud that the ships anchored at sea could probably hear her. Wave after wave of intense pleasure crashed through her body like the waves of the ocean breaking on shore.

Oliver was surprised at how long her orgasm was lasting. The thrashing and wiggling of her ass against his cock along with Lilly’s screaming and cursing was driving him over the edge as well. The tip of his cock suddenly became ultra-sensitive as Lilly’s bubbly ass relentlessly bounced and rubbed against it. He suddenly felt an incredible sensation in his pants, then his orgasm hit.

“Unnnnnggghhhhhhhhhh!” Oliver belted as the surprise orgasm swept through his body. He began sending hot shots of sticky cum down the inside of his pants onto his thigh. Lilly was still in the middle of her orgasm when Oliver’s started. Her continued movement milked the cum strait out of his cock making Oliver’s orgasm more and more intense. His thigh soon became drenched with his own hot cum and it began soaking through his thin cotton pajama pants.

Oliver and Lilly rode through their first major orgasms together. As they came down from them Lilly tilted her head to the side and whispered her remaining moans into Oliver’s ear. Then with her last ounce of strength she whispered, “I love you.” A serene calm passed through her and she fell silently asleep in Oliver’s arms. It was so quiet now. Oliver removed his hands from her breasts and pussy. He pulled down her shirt and gently adjusted her clothes. He wrapped his arms around Lilly and looked up at the stars, the full moon was out. Lilly’s last words repeated in his head.

“She said she loved me.” Oliver smiled before the gentle rhythm of the waves ushered him to sleep.