Chloe's Cherry

Chloe grabbed Harry's cock through his boxers. Now free of the jeans, she could feel along the whole length, right to the end. She could feel his balls underneath, and she could feel the soaking wet material where the end had been earlier, and where it was now. It was pressing against the material of the boxers, pushing them out like a tent, and where the end of his cock touched the fabric there was a huge droplet of wet precum that only seemed to be getting larger. She put her thumb in the liquid and moved it around. Now it was Harry's turn to moan. Chloe was touching the most sensitive part of his dick through the wetness and the fabric, and it felt amazing. He hadn't felt this good with a woman touching him for as long as he could remember.

"God that feels so nice," he said.

They looked at each other and smiled. They were already old friends, even though they had been talking for only a few weeks. Being here, now, felt so right. It felt inevitable, like a force of nature. They were lost in each other now. Harry sat next to Chloe as she played with the end of his dick through the boxers. He started stroking her thighs. The soft young skin felt incredible beneath his fingers. Again he moved upwards and quickly found his way between her pussy lips into her amazing warm wetness. Again he pushed two fingers inside her, and this time she arched her back as she cried out. Then her cry became a moan, and then a sigh.

In response, Chloe traced her hand upwards along the material of the boxers to the elastic at the top. She lightly traced along the top of the elastic, caressing the bare skin, and giving Harry goose bumps. Chloe smiled at him mischievously. It was such a turn-on. Harry knew what was coming next, and savoured the anticipation. Chloe's hand dived down inside the elastic and found his dick. With her other hand she pulled the elastic down and his cock was finally free, a sudden coolness hitting it.

Harry pushed his fingers deeper than he had before, making Chloe's back arch again, and putting a big smile on her face. Then Chloe started moving her hand up towards the end of his dick, slowly but firmly. Harry held his breath as he knew what was coming. Soon enough, Chloe's fingers reached the bell end and rubbed over his special spot. Harry cried out and his head fell back as his neck muscles disintegrated. This was the most sensitive part of his dick. Chloe had just brushed past it but it was the most intense feeling. Harry responded by pushing his fingers further inside her, and she cried out again.

Chloe seemed to enjoy the control she had over him. Playfully, she moved her hand back down over the same area, trying to figure out the exact spot she'd touched. He cried out again as she travelled past it. Up she went again, grinning at him.

"Does that feel good?" she asked.

Harry could only nod and grin before her hand touched his spot again and he cried out again, no longer in control of his voice. She teased his spot over and over again, until he was bucking with pleasure and moaning constantly. He couldn't even focus on fingering her anymore; she was in control now.

Chloe stopped and Harry realized his eyes were closed. He opened them as she grabbed the sides of his boxers and started pulling them down. She giggled as he helped her pull them past his feet, then he turned around suddenly and pushed her flat onto the bed again, to more giggles.

"I want to lick your pussy," he said. Chloe writhed on the bed at the idea, and smiled a big happy smile.

"OK," she said excitedly.

He leaned over Chloe and kissed her on the lips, then the neck, and then he moved his hands to her hips. He felt like a teenager himself. He moved his head close to her body and kissed the lacy material on the front of her G-string. Chloe wriggled. He pushed her thighs apart to make room for his face. He got down and gently kissed her pussy and G-string. Chloe gasped. Harry put his tongue out and gently licked the outside of her pussy lips. She moaned and shuddered. Harry held her hips tightly to stop her from moving. Now he was in control again. He licked up and down the slit between her pussy lips. They were closed together so he was still not tasting her, just teasing her. She writhed on the bed in anticipation. Then, applying just enough pressure, he forced his tongue between her lips, and licked quickly upwards, lapping up her juices. It was the sweetest pussy he'd ever tasted. Chloe moaned loudly, and then squealed and tensed up when he flicked her clit with the end of his tongue. He pulled away and she relaxed and sighed.

"Is that good?" he asked, smiling. Chloe nodded and grinned.

Harry performed another lick between her pussy lips, from bottom to top, licking her clit and then pulling away again. She moaned and gasped, and this time she arched her back when he touched her button, and collapsed back onto the bed with a sign when he stopped. He repeated this a few times, each time Chloe responded more when he licked her clit, until she was moaning heavily and almost screaming at the end. Harry paused for a second, then Chloe took control again.

"Take my panties off," she ordered.

Harry grinned at her. On the day he'd declared his feelings for her, Chloe had undressed down to her panties for him on the webcam. As she'd modelled them for him, she'd told him that he could take them off any time he wanted. It seemed so long ago now. He was going to take his time over this.

He started by rubbing his finger in her panty crotch again, and pressed inwards, so her G-string rode up between her lips and into her wetness. Then he grabbed the side strings and pulled slowly downwards, teasingly, savouring the feeling of finally removing them. He slowly pulled the waistband over her pussy and down her thighs, while the crotch stayed in place, nestled in her pussy. He slid down further until the crotch came away, a thread of clear wetness connecting it to her pussy for a moment before breaking. She sighed at the feeling, then he pulled the G-string all the way down to her feet and off. He glanced down at it - the inside of the material was white with her fluids - then threw it on the floor.

Chloe was now naked from the waist down. Harry could see her pussy in its full glory for the first time. It was completely shaved, and her pussy lips were pink from her arousal, and glistening with her juice.

"God you're beautiful," he told her.

Harry lowered his face once more to Chloe's pussy. He kissed it again, then pushed his tongue between her lips. Chloe was writhing on the bed and moaning at the touch. He licked around inside her lips, licking her clit, and licking the soft pink parts of her pussy. He teased her hole a little but didn't push his tongue inside just yet, preferring to massage the whole area. The room was filled with Chloe's moans and sighs and cries, a cacophony of lust and desire. He could have stayed here forever. It was a beautiful moment, sexual and loving at the same time.

Harry moved his head upwards and kissed Chloe's shaved mound, then her navel. He pushed her vest top up and kissed her stomach. He worked his way up, pushing her vest away as he went, kissing in a line until he reached her bra, then he kissed inside her cleavage, and all over the exposed parts of her breasts.

Chloe sat up and removed her top, and then her bra. She was completely naked now. Harry sat up and put his arms around her waist, then bent down and kissed her nipples, flicking them with his tongue and sucking them into his mouth. They got hard instantly.

Then Chloe grabbed Harry's T-shirt and pulled it quickly over his head, forcing him to release her. They were both naked now. Naked and ready. A moment passed as they looked at each other.

"I think it's time to put that condom on, Harry," she said.

This was it. Chloe was ready to lose her virginity. He'd fantasized about it, and then they'd talked about it online, and now it was finally going to happen. He'd wanted it so badly for so long. He'd wanted to make this a night she would never forget. He'd wanted to make it special and amazing and satisfying. This would make it perfect. He was going to make love to her. Right now.

He reached down and grabbed the condom from his jeans. He unwrapped it and slipped it over his bell end, then showed Chloe how to smooth it down over the shaft. She did it slowly and seductively, wanking him off slightly as she went. Harry moaned gently as she rolled the condom down bit by bit until she reached the end. Then she lay back on the bed with one arm above her head and the other resting on Harry's knee. Harry shifted Chloe slightly across the bed so she was in the middle, her legs apart. He knelt between her knees and looked down at her, his dick standing to attention, ready for action.

"What do you want me to do now, Chloe?" he asked with a smile.

"Fuck me, Harry," she said, "I want you to put your dick inside me, right now."

This was it, his ultimate fantasy was coming true. His gorgeous teenage friend was lying in front of him, completely naked, and asking him to take her virginity.

He leaned forwards over Chloe and held his weight with his left arm. With his right arm he held his condom-covered dick. He gradually edged closer to her, until the end of his dick just touched her pussy. He teased the end up and down between her pussy lips, as he had with his fingers. She shuddered and let out another moan.

"Are you ready?" he asked.

"More than ready," she smiled back.

Harry pushed the end of his dick against Chloe's pussy. The angle was just right - it slid into place right over the entrance. Another centimetre and he would be penetrating her. He hoped it wouldn't hurt her too much. She was as wet as a girl could get, but she was going to be tight. He pushed gently, and met gentle resistance. Chloe held her breath. He pushed a little harder. There was some give, but still resistance. Harry stopped for a minute, with his dick in place, and leaned in to kiss Chloe. He really didn't want to hurt her. They kissed for a minute like old lovers, then pulled apart again.

"Do it," she commanded.

Harry gulped. He pushed a little harder, then a little harder, then a little harder still. Suddenly he felt the resistance give way with a rip. Chloe screamed at the top of her voice as her pussy opened up, for the first time ever, to allow his dick inside her.

The feeling was almost indescribable; Harry felt it in his bones. It was as if everything was stuck together inside her, and he was forcing it apart, almost tearing it open, irreversibly. He was just a centimetre inside her but it was obvious that she would never be the same again. This was a permanent change to her body. She was no longer a virgin. Harry had deflowered Chloe in just a second, and now she was a woman, and they were lovers.

"Are you OK?" Harry asked, concerned. Chloe was red in the face and panting. She couldn't smile, there was too much going on for that. She shook her head.

"I'm fine," she said.

Harry took it slowly. He withdrew and pushed back in, no further than before, playing with the penetration that he'd achieved. The condom meant he couldn't feel Chloe's wetness, but he knew it was there, and he was dipping into it each time. Chloe just breathed deeply, recovering from having her cherry popped. The redness slowly faded from her face. Then she looked at him seriously. No words were needed. Harry withdrew once more and Chloe braced herself.

Harry pushed in again hard, forcing entry, and opening her pussy wider and deeper than before. Chloe arched her back and screamed again. It was unsettling, feeling that he was tearing her open and making her scream, but it certainly proved she was a virgin. There was less pain in her face this time, he thought. She looked at him lustfully, and he leant over and kissed her passionately, with his dick still half an inch inside her. They continued kissing while Harry played with the length he'd opened up, pulling in and out slowly so Chloe could feel every movement. She was melting into his kiss now. The pain had passed, and he was giving her pure pleasure. It felt amazing for him too. He couldn't remember ever having a pussy as tight as this. Even with the condom, he could feel it squeezing his dick hard. And the way she was melting into his kiss while he slowly made love to her was deeply satisfying.

They held each other tight, their mouths melting together, moaning with lust, as Harry continued slowly fucking her. Every few strokes he'd add a little force and push a little deeper, opening her up a little further. Each time she would shudder in his arms and gasp into his mouth, then melt into his lips again. Eventually the resistance stopped, and he seemed to break through into an opening inside her. He slid an inch further with ease, until he was about halfway inside. He stopped trying to go further, and just fucked her slowly with half his length.

Chloe seemed uncomfortable, though. She broke off the kiss. Her face seemed unhappy, somehow. Harry lifted himself with his arms and looked down at her, concerned.

"Are you OK?" he asked her. She bit her lip and furrowed her brow, as if considering something, before answering.

"Harry, take the condom off."

His jaw dropped.

"What?!" he asked.

"I want you to take the condom off," she repeated.

This was not the plan. He was married; having an affair already jeopardized that but getting her pregnant would pretty much end it. It was too risky.

"Chloe, I don't want to get you pregnant," he replied.

On the other hand, she had a tight little pussy that was soaking wet and he couldn't even feel it properly. He'd been silently cursing the condom since they began.

"I won't get pregnant if you don't cum inside me," she said.

Harry felt himself being swayed by her logic.

"Chloe, you might. I don't want to take that risk."

Chloe just looked at him. Her eyes seemed very big all of a sudden, and her face was pleading. He wanted it to be perfect for her, and it was what he really wanted too. It was just the risk. Harry's head was spinning as he searched for a compromise.

"Well, look, I'll try not to cum inside you, but if I do, you have to promise to take the morning-after pill, OK?"

"I promise," she said, then she reached down and pulled the condom off him and threw it on the floor.

The cool air blew against his dick and he felt naked freedom again. It was delicious. He was going to put his dick inside his lover and feel her wetness all over him. And he might get her pregnant. The thought thrilled him. This was a dangerous game now. He knew she didn't have any birth control except the condom. If he came inside her ...

The idea spurred him on. It was sexy as hell. Fucking bareback, with all the additional pleasure and all the additional risk it involved. All of a sudden his dick seemed even harder than it was before.

Harry moved back into position as Chloe laid back on the bed. Once again he reached down and teased her pussy with the end of his dick. Except, now he could feel her wetness, and she could feel his. It was mind-blowing. Their fluids ran together, soaking her pussy lips as he rubbed her directly with the end of his uncovered dick. Yes, this is what he had really wanted all along. This was the real experience. Tonight was about making love, sharing each other's fluids and bonding with each other in the most intimate way possible.

How was it going to feel putting his dick inside Chloe's pussy now? The anticipation was almost unbearable.

He manoeuvred again so the end of his dick was pressing against Chloe's entrance. So much wetness. He pushed ever so gently and slid halfway in again with no resistance. He couldn't believe the way her pussy felt inside. It was like a swimming pool, filled with her juice; the end of his dick was completely bathed in warm fluid. He pumped in and out slowly, enjoying every nuanced feeling. Chloe just lay there, writhing gently, and clearly enjoying it as much as he was. They grinned at each other.

"God, it feels so good," he said. Chloe smiled back, and nodded as best she could.

Harry could have stayed inside Chloe like this forever. He wasn't even close to orgasm yet. The combination of lack of sleep, the lateness of the hour, and the alcohol he'd had tonight, were all helping him to stay in control. And anyway, tonight wasn't about him. It was about Chloe. It was about showing her how amazing sex could be with the right person, and making sure her first time was something she remembered fondly for the rest of her life. He could cum any time.

"Let me suck your dick," Chloe said.

"OK," Harry laughed, "fine by me!"

He popped out of her and sat up beside her. Chloe sat up too, cross-legged. She told Harry to lie down, then got on all fours beside him. She kissed him on the lips, passionately, then started a chain of kisses down his neck, down his chest, across his stomach, and then she kissed the end of his dick. Harry sighed loudly; it felt lovely just to be kissed down there. Then Chloe put her tongue out and licked the end of his dick. That was even better; Harry moaned and more precum dripped out of him. Then she took the end of the dick in her mouth, and closed down around it with her lips. There was nothing Harry could do except moan in appreciation. With his dick in her mouth, Chloe flicked the end with her tongue, making Harry writhe with pleasure. But Harry was feeling restless somehow. He didn't like just sitting there and taking it.

"Let's do 69," he said. "Lie down."

Chloe lay down on the bed, still completely naked. Her legs were angled apart, and her pussy lips no longer met in the middle. Instead, they gaped open slightly, letting Harry see the pink interior, which was dribbling with her juices.

Harry climbed over her on all fours, with his head near her waist. He sat down a little so Chloe could take his dick in her mouth. She closed her lips around it as before and licked the end. Harry leaned down and licked Chloe's pussy between the lips. Harry got in closer and focused on Chloe's clitoris for a while, flicking it with his tongue and then sucking it into his mouth. Meanwhile Chloe was taking more and more of Harry's dick into her mouth, licking all over it. They both moaned continuously.

Harry pushed his head further down and licked the opening to Chloe's pussy, savouring the taste once more. Then he stuck his tongue straight out and pushed his head inwards so his tongue penetrated her. Chloe writhed and gave a muffled moan with her mouth full. Harry started fucking Chloe with his tongue, making it as hard as he could. He could really taste her insides now, and it was the best tasting pussy he'd ever had. Chloe continued to writhe, while she moved her head up and down his dick, letting him fuck her mouth while his tongue fucked her. They continued the 69 until Chloe stopped writhing and lay still, slowing her sucking on his dick too. Harry wasn't sure if she'd cummed or if she was just ready for a break. He looked up at her, through the tangle of their bodies.

"Do you want some tea?" Chloe asked him. He laughed.

"That'd be lovely, actually," he said.

They took a toilet break, made some tea, and sat on the back doorstep chatting for a while. Chloe wore a robe and Harry was still naked.

"It's funny, you know, most people do all this stuff over several months, but we've done it all in one night. You've fingered me, you've licked me out, we've done 69, we've fucked."

"Did you want to take it slower?" Harry asked, suddenly concerned.

"No!" she laughed, "I just think it's funny."

Harry got the idea she was quite proud of herself. It matched the way he was feeling precisely. He leaned over her and pushed her down onto the floor, pinning her shoulders down with his arms.

"Mmm, kinky!" she smiled.