Jack's Regrets

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Jack passes up an opportunity he shouldn't have.
3.8k words
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Part 1 of the 2 part series

Updated 06/08/2023
Created 06/08/2017
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"Okay guys, I've gotta pee, I'll be back." Lily got up, sliding her feet into the wellies by the door and pulling on a raincoat.

"Hey, I'll come with you," called Jack, moving out of the circle of their friends to hold the door open.

The darkness outside was almost absolute with only the stars and the moon lighting the campsite. Lily fumbled her torch out of her pocket and switched it on. She pulled her hood over her head and looked over to Jack, shining the torch in his face.

"You sure you don't want your coat?"

"Nah, it's barely drizzling. And it's not far," replied Jack, setting a fast pace with his long legs.

"I can't keep up when you walk that quickly, you bully," she whined playfully, skipping to keep up.

"Really? You're going to play that card?" asked Jack, slowing down slightly. Lily ran to get ahead of him and jumped with both feet into a huge puddle, splashing him with muddy water. He stopped short and looked down at his soaked jeans.

"I am going to get you for that," Jack threatened. Lily squealed and sprinted to the safety of the toilet blocks, Jack hot on her heels.

When she came back out, Jack was leaning against the side of the cabin under a light, a lit cigarette between his lips and smoke curling around him.

"Truce?"

"Truce," he agreed, "You want one?"

She took the proffered cigarette, letting him light it for her and took a long drag. A sense of calm settled over her feeling the smoke in her lungs and watching it rise through the rain when she exhaled. She leant her head back and looked up at the stars.

"You look so hot right now," said Jack. Lily looked over at him to find his eyes fixed on her, raking up and down her body.

"Yeah, I put the coat and boots on just for you. I've heard all about your fetish for weather-resistant clothing," she responded, raising an eyebrow.

"You're just missing waterproof trousers, then I'd be unable to resist you at all."

Lily looked down, fighting a smile. Taking a final pull on the cigarette she stubbed it out under her boot and started walking back.

They could hear the raucous laughter from their cabin before they reached it. Lily paused outside to shake the water off her coat as Jack reached past her to open the door for her.

"Here, let me get your coat as well," said Jack, watching Lily unzip her jacket and taking it from her to hang it by the door.

"Thanks," Lily smiled warmly and kicked off her boots to sink back into the armchair.

"Good timing guys, we're about to play ring of fire," said Ed, handing them both empty glasses. The playing cards were spread in a circle around an empty pint glass in the centre ready to play. "Standard rules in play to begin with."

"What do you want, Jack? I'll mix you something," asked Lily.

"I'll have whatever you're having," answered Jack, meeting her eyes and winking.

Fifteen minutes later, play was getting out of hand. Everyone was several drinks down and the rules were getting progressively more and more complicated.

"So wait, I can't use any words beginning with a vowel from now on?" asked Kate in disbelief.

"I thought it was any word with a vowel in it," countered Ed.

"If it was, you need to drink at least five times for that sentence," laughed Lily, taking a sip of her drink for good measure.

"What about y? Are we counting that as a vowel?" asked Anna.

"You guys are useless. I'll simplify. No one can begin or end a sentence with a vowel," said Jack, rolling his eyes. "And while we're at it, I need another drink, Lil."

"What happened to your last slave?"

"She used too many sentences ending in vowels -- drink."

Everyone laughed and the game moved on.

There were only a few cards left when Lily drew the final king, the king of hearts. She looked with utter dismay at the dirty pint, knowing the mixture of whisky, beer, gin, coke and lemonade would definitely push her over the edge.

"Guys, I can't drink that," she said, glancing around the circle.

"It's the rules and you know it," said Ed, completely without pity.

"I'll be sick, really I will," she begged.

"Maybe she could do a forfeit?" asked Anna.

"I think she definitely could," replied Jack with mischief in his eye.

"But what would be a worthy forfeit for not doing the dirty pint?" asked Ed.

"Maybe she could kiss one of us."

"Yeah, or sleep outside?"

"Too much, how about she has to cook everyone breakfast tomorrow?"

"Or maybe she should take off her dress," Jack's voice carried over the noise. Once again, his eyes met Lily's before running over her body.

"Fine," said Lily, "the dress it is but Jack has to drink the pint."

She waited until he raised the glass to his lips before standing up and unzipping her dress. She hesitated for a moment before moving her long hair to the front of her shoulders so it hung down over her breasts and then peeled the dress off her body to step out of it. She almost didn't hear Jack choke on the drink over the sound of the catcalls and wolf whistles from her friends. Jack couldn't stop drinking her in. If she had looked hot in the deep red velvet dress, she looked spectacular out of it. The dark grey lace shorts emphasised her legs and he couldn't help imagining what her breasts would look like if only her hair wasn't hiding them. He hoped the bra was matching grey lace to highlight the curve of her breasts. Her skin had a perfect golden glow with a mole on her ribs he longed to kiss, along with the rest of her.

Jack slammed the empty pint glass down on the coffee table as he finished it.

"What next?" he asked.

Ed was the first to reply.

"I'm very supportive of having some more forfeits for the girls if this is what we're in for."

Kate and Anna exchanged a look.

"You're a funny man, Ed. Maybe when hell freezes over."

"We could watch a film and make a drinking game of it?" suggested Lily.

They chose a film they had all seen a hundred times and set rules for when to drink, everyone getting comfortable around the TV. Anna passed around bowls of popcorn and blankets, topping up drinks as necessary. After they had all settled down, Jack stole another glance at Lily who had a blanket pooled around her waist. Her hair had fallen back over one shoulder and he could see the dark grey balcony bra he had hoped for peeking out. The lace was sheer and he imagined he could almost see the shadow of her nipple in the low light from the TV.

As the film drew to a close, he looked over at her again as he had been doing often. Her head was leaned back against the arm of the chair behind her, her eyes closed and her eyelashes dramatically fanned against her cheek. Her lips, which were painted a deep red to match her dress, were parted slightly while she dozed. The girls unfolded themselves slowly from the sofa, careful not to wake Lily, and blew kisses to the boys, heading to their bedrooms. After a whispered conversation between Ed and Jack, Ed headed to the door, going back to the boys' cabin.

For a while, Jack simply watched her doze, unable to get over the perfect way her lipstick looked or how beautifully her hair contrasted with her skin. He didn't move until he saw her shiver, conscious that with no one else in the room and no fire lit the temperature was dropping. He leant over to her and pulled the blanket further up her body, brushing the back of his hand over the rise of her breast as though by accident. Jack began tucking the blanket around her until she stirred and he froze, one arm across her body. Her eyes fluttered open.

"Making a move on me while I'm asleep, Jack? Not exactly the kind of guy I had you down as," she whispered.

"I was just putting the blanket on you, Lily, don't get any ideas."

"Ideas? Me? Never." She stretched upwards, allowing the blanket to fall off her again. "Anyway, I guess I should get to bed."

"As a gentleman, I have to insist I walk you to your door," said Jack, standing up and offering her his hand. He pulled her to her feet and concentrated hard on looking at her face and nowhere else. In less than ten paces, they had reached her bedroom door.

"Thank you for walking me home, Jack, how will I ever thank you?" she said, fluttering her eyelashes.

"Well, my lady, you needn't thank me. Just let me kiss you," he replied, bringing her hand to his lips and kissing it lightly. "Night, Lily."

"Night, Jack."

He turned to walk away.

"Are you sure you can make it back to your cabin?" she asked.

"Pretty sure, Lil," he said, turning back to face her.

"I was just thinking that we did drink an awful lot tonight," she said, twisting a lock of her hair around one finger.

"We did. Probably more than was wise."

"Probably. Maybe you'd be safer staying here."

"Maybe," he replied, leaning his arm against the doorway. "Would you come and check on me in the night if I slept on the sofa?"

"It would be a lot easier to check on you if you were in bed next to me," Lily said, a blush rising to her cheeks.

It took nothing for Jack to close the distance between them. He slid his hand around the back of her neck, tangling his fingers in the hair at the nape of her neck and pulling her head backwards to make her lips meet his. His other arm encircled her waist to draw her close to him. He could feel one of her hands on his jaw and the other running along the waistband of his jeans, seeking the edge of his t-shirt and his bare skin underneath. Their kiss was pure dynamite, a frenzy of lust waiting to explode. When both of his hands cupped her arse and forced her further onto her tiptoes she gasped into his next kiss, matched only by his moan when she caught his lip between her teeth and sucked it.

Lily pressed her hands up under Jack's shirt to feel the ripple of every muscle in his back as he kissed her. He couldn't get enough of the feel of her lace underwear against his fingers as it stretched across her arse. Both of them luxuriated in the other, Lily running her hands over Jack's pecs and shoulders while he explored the curve of her hip with his hands. When he ran his hands up her sides to reach her breasts and ran his thumbs over her nipples to feel them harden for him, Lily whimpered and they both drew apart breathing heavily. He gazed down at her and pressed the sweetest kiss against her lips.

"I want you to be sober when we do this, Lil," he breathed, running his thumb along her bottom lip.

"I... Jack, no. I want you. Now. Just like this," she replied, searching his eyes for the affirmation she desired.

He kissed her again.

"I need to know you're sure. Right now, you're drunk and you're tired and you're probably over-excited."

"Over-excited?" Lily took a step backwards, "Over-excited?! Maybe I'm over-excited because you just kissed me. You led me on and now, what, you don't want me at all?"

"Lil, keep your voice down. I do want you. I just want you sober and able to experience every second of what we're going to share," he said, taking a step to close the distance between them. Lily matched his step, keeping distance between them.

"Don't call me that and don't tell me what to do. I can't believe I went along with this. Get out of my room. Now," Lily hissed. She pushed him firmly against his chest and swung the door closed, locking it immediately.

"Lily? Lily!" Jack whispered through the door, rattling the handle, "Open the door, please. Lily?"

Lily turned on her heel, ignoring Jack and heading for the bed. She pulled a top out of her drawer and unhooked her bra, throwing the bra into the drawer and pulling the top over her head. She collapsed face-first onto the bed, tears stinging her eyes and too tired and angry to process it properly.

Jack stormed away from Lily's room, picking up his coat on his way out of the cabin. As soon as he was outside he dug in his pocket for his cigarettes and took one. He tried to light it, his lighter sparking uselessly with no fuel.

"Shit!" he exclaimed, throwing the lighter away where it bounced against the wall of the cabin. He could picture his other lighter perfectly, right in the centre of the girls' coffee table. "Fuck!"

Tucking the cigarette back in the packet, Jack realised it was raining much more than it had been earlier and he was soaked through. Shoving his arms into the sleeves of his raincoat and roughly pulling the hood over his head he stomped away from the cabins.

***

Ed jumped as he heard something hit the wall of the cabin, guiltily thrusting his hand under his pillow to hide his phone and closing his eyes to fake sleep. When no other sounds came, he opened one eye and glanced around. No one was there. He drew his phone back out.

You looked so hot earlier, I can't stop thinking about you.

He'd been composing this message for so long now, writing and re-writing it. Did that sound too earnest? Was it too keen? Hmm.

I can't get the image of you in your underwear out of my head.

No, that wasn't right at all. Way too stalker-ish.

Did you get to bed okay? x

Simple, to the point, nothing about underwear. Okay. Send.

A response came back almost immediately.

Yes thanks. I can't sleep though. Any ideas? xo

Did it mean anything that she had signed it off 'xo' instead of just 'x'? Okay, ideas, ideas.

Are you too hot? Too cold? Thirsty? x

Keep it innocent.

Again the response was almost instantaneous.

I guess it is pretty hot in here... xo

Dot dot dot? That's got to mean something. Maybe it's time to try something.

Could just be you though ;) x

This time the wait for a response seemed to stretch into hours.

Funny. I was just thinking there was no reason for it to be hot in here, given that you are nowhere to be seen ;) xo

He must had re-read the message ten times before the meaning sank in. She thought he was hot! She was flirting back with him!

My advice would be to take off some layers of clothing and try to cool off x

Difficult to take off layers when you aren't wearing anything... xo

His dick was so hard just thinking about her lying in her bed and texting him, naked. He shifted it inside his boxers, trying to make it more comfortable.

His phone buzzed again.

Nothing except my lipstick, anyway. Wanna see? xo

Jesus Christ did he want to see. Would that be the wrong thing to say? Only one way to find out.

I can't think of anything I'd like to see more x

The next time his phone buzzed he could hardly bear to look at it. What if she had flat-out rejected him? What if she hadn't? He pressed the message to open it.

The picture that filled his screen was beyond anything he could have imagined. She was lying down, her perfectly painted lips at the top, moving down to the perfectly peaked and rosy nipples then further down to her perfect stomach and her perfect legs. Her mons was smooth and hairless, the same sun-kissed gold as the rest of her body. He felt his cock harden even further as he took it in, his eyes scanning the picture over and over again. Another message came through.

Well? What do you think? xo

This time he didn't have to think about what his response would be.

I can honestly say that the only thing better would be to see it in person x

Moments later he heard the door to the cabin open and then close again before his phone vibrated.

Ask and it shall be given xo

His bedroom door opened and Lily stood framed in the doorway in her raincoat. Her hair was slightly mussed from where she had been lying down and there were water droplets in her eyelashes and beaded on her legs where they had been bare between the bottom of her coat and the top of her boots. Slowly she unzipped the front of the coat revealing her cleavage. When she shrugged the coat off her shoulders it fell away to expose her bare breasts and her hard pink nipples. He could hardly tear his eyes away to follow the zip downwards and see her gradually reveal what was between her legs.

The coat dropped to the floor and she cupped one breast in each of her hands, taking the nipples between her fingers and rolling them. Ed had never seen anything so erotic and felt his cock twitch in response. When she licked her fingers and ran them between her legs he finally gave in, releasing his cock from his boxers and stroking it while he watched her dip her fingers inside herself. She was more than happy watching him, her eyes alight with desire as she played with her clit and observed his hand on his dick.

When Ed's eyes closed in pleasure, Lily took the opportunity to take a place on the bed between his legs. She leaned forward and took the tip of his dick in her mouth, sucking gently on it and tasting his pre-cum. His eyes shot open at the sensation and found her looking up at him while she swirled her tongue around the head of his penis.

She brought her hand to the base of his penis and twisted it around it while she continued to tongue the tip. Ed gathered her hair into one of his hands and encouraged her to take more of his dick in her mouth, not that she needed the encouragement. Her eyes still on his, she pressed her head forward and took him deeper. Lily fought her gag reflex as she bobbed her head again and took him into her throat. Her eyes watered and she withdrew, sucking hard on the tip again. The next time, she managed to take him all the way inside her throat, her lips touching the dark hair at the base of his cock and her tongue pressed flat along his length.

Ed couldn't remember a time he had felt better. The feeling of Lily alternating stroking her hand around his cock while tonguing the tip and taking him all the way into her mouth was insane. She was sucking as hard as she could when he felt it.

"Uhh, Lily..." he groaned. In response she took him deep into her throat again, her eyes watering. She stroked her hand up his thigh to cup his balls, tugging gently on them. She felt them tighten just before she felt the first spurt of his hot cum hit the back of her throat. Lily moaned and moved to suck the tip, watching all his muscles tense as he came for her. She swallowed every drop and waited until all the tension had left his body to withdraw his cock from her mouth. She licked it all over, making sure she hadn't left any cum behind and tucked it back into his boxers.

Ed's eyes had closed as he came and the next thing he felt was a warm body pressing against the entire length of his. She hooked her leg over one of his and he felt a hot wetness pressing against his thigh. He wondered if he should kiss her. Her fingertips were trailing over his chest, starting at one shoulder and running down his torso then back up. It was so soothing and she was so warm and soft next to him. In a second he'd open his eyes and thank her properly.

***

Jack entered the cabin and took off his boots. Despite the raincoat, he was soaking wet, his hair hanging in down in thick, wet strands. He shook off like a dog and ran his fingers through his hair, feeling a sudden chill. He headed straight to the bathroom and took off his top and his jeans to hang them on the shower rail and drip into the bathtub. He started the shower running, sure he wouldn't wake Ed who could sleep through anything, and waited for it to heat up before peeling off his sodden boxers and stepping underneath the water. He hung his head and let the water wash over him until he felt his skin start to thaw out. He washed thoroughly and turned the shower off to step out. He rubbed the towel over his head to dry his hair and then wrapped it round his waist.

He noticed the cabin was cold as soon as he stepped out of the steamy bathroom and into the living room. Going into his bedroom, he pulled on some pyjama bottoms, gave his hair another cursory rub with the towel, and got into bed. He lay there staring at the ceiling and fidgeted first to one side then the other. Eventually he sat up again and got up. He rummaged in his bag to find a soft, white t-shirt with long sleeves and then went to see if Ed was awake.

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