Jack's Regrets Ch. 02

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Jack tries to come to terms with his decision.
3.7k words
4.17
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1

Part 2 of the 2 part series

Updated 06/08/2023
Created 06/08/2017
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Kate had her dirty blonde hair tied back and her face buried in Anna's crotch. Her bare arse was high in the air while she knelt on the bed between her friend's legs, licking her pussy in earnest. With Anna's legs over her shoulders, she could only just hear the tiny whimpering moans Anna was making when Kate flicked her tongue over her clit.

"Mmm is that good, Anna? You taste so good, honey," she paused to say, kissing Anna's inner thigh and licking Anna's wetness off her own lips.

Anna's fist was clenching and unclenching in the sheets it felt so good. If drinking games always led to this, she might join in more often.

"Yes, Kate, yes, your tongue, oh my -" Anna managed to reply before Kate sunk her tongue into her once again and her words were lost in a moan. It felt like Kate's tongue was so deep inside her pussy she was trying to find the source of her wetness, plunging it in and out of her over and over again in her quest. She stroked her hand over Kate's head, absentmindedly playing with Kate's ponytail instead of the sheets.

"Oh, oh, Kate, that's so good, I think I'm gonna cum, oh yes," cried Anna, taking Kate's hair in her fist and pulling. She tensed suddenly, yanking Kate's head up and forcing her mouth away from her when she heard the front door of the cabin open and close. Kate stopped for a moment, listening.

"It will just be Lily coming to bed, she's not going to bother us. Let me finish," said Kate, leaning forward again.

They both heard a sudden thump and a very male voice swear.

"Oh shit, it's Jack. Get under the covers," hissed Kate, sliding up the bed next to Anna and pulling the covers up over them both. Kate glanced at Anna, reached over and tucked her boob back into her top. They had both collapsed into giggles when Jack knocked on the door.

"Psst. Are you both in there? One of you had better be awake because I've just hit my head on the fucking coat rack coming to find some company and if my effort was wasted..." he whispered as he pushed the door open.

He stopped for a second to take in the unexpected scene before him. Both girls were in the twin bed against the far wall with Anna being little spoon for Kate, who was leaning up on one elbow to greet him. A considerable amount of Anna's cleavage was visible despite both of them being under the duvet.

Jack invited himself in and sat on the other bed, facing the two girls and resting his elbows on his knees and taking his face in his hands.

"Look, I think I've really fucked things up tonight and I don't know what to - " he looked up suddenly, hearing Anna's gasp as Kate slid a finger into her pussy. He cocked his head to one side, "Am I interrupting something here?"

"No, nothing," said Anna quickly.

"Right... So as I was saying, I might have done something stupid," continued Jack. He looked up at them and narrowed his eyes as he took in Anna's expression. "Are you sure I'm not interrupting anything?"

"Actually, you are," cut in Kate, "I was on the verge of giving Anna the orgasm of her life before you hit your stupid head and distracted her."

"Kate!" squealed Anna, "You hardly had to tell him that!"

"Well, well, well," smirked Jack, his mood abruptly shifting, appearing to instantly forget his worries, "don't let me stop your fun."

"Oh, I'm not," replied Kate, looking equally smug, "I've got a finger inside her right now. Two, in fact."

Kate pressed a second finger into Anna, feeling her pussy tighten in pleasure around the intrusion. Anna gasped again.

Jack raised his eyebrows at them both.

"I'm not sure I can believe something like that without certain visual evidence," said Jack, his eyes meeting Kate's in a challenge.

"I'd love to show you what I'm doing but my hands are full," responded Kate, flicking her eyes downward to the movement just visible through the duvet and back up to his eyes. Jack merely spread his hands and shrugged, shifting back on the bed to lean against the wall.

"Do you want to show him, Anna? Do you want him to see my fingers disappearing into your pretty pussy?" Kate breathed into Anna's ear as she slowly withdrew her fingers before pressing them back into her again, "Do you think he deserves to watch your pussy as well as your face when you cum for me?"

Anna whimpered with pleasure and shook her head. Kate kissed her neck just below her ear and stayed close to continue.

"Anna, honey, you're so beautiful and look how hard you're making him when he can't even see it. You're getting so wet for me thinking about him looking at us. I can feel it all over my fingers."

Anna met Jack's eyes and reached up to grasp the covers. She glanced down and saw him adjust his cock where it was confined in his pyjama bottoms. She pulled the covers off her, Kate taking them from her to fold them at their feet. Her pussy felt empty without Kate's fingers but she had to admit she could feel the heat from Jack's gaze turning her on more. His eyes lingered on their entwined legs, up to her glistening pussy lips and her neatly trimmed pubic hair.

"Gorgeous," he finally pronounced, "although altogether too clothed for my liking."

"Right back at you, Jack," Kate purred, watching hungrily as he took off his top to reveal smoothly defined abs and pecs. She kneeled and responded in kind, exposing her breasts and her peaked nipples. She kissed Anna and allowed her to feel her body pressed up against her before kissing down her neck and sliding lower on the bed. She met Jack's eyes once more before turning her concentration back to Anna's pussy.

She licked along her dripping slit, savouring Anna's taste, and pressed her tongue flat to her clit to lick upwards. She felt Anna's body twitch as she used her fingers to part her lips and dip her tongue inside her again to lap at the wetness there. She pushed her tongue inside as far as she could and moaned at the sensation of her mouth and nose pressed as close to Anna as she could be.

Kate looked up at Anna to watch her reaction and found her head thrown back on the pillows, her eyes closed in bliss. Kate pushed two fingers into Anna's pussy and saw her back arch in pleasure. When she started flicking her tongue quickly over her clit she was rewarded with Anna's moan and when she curled her fingers upwards inside her Anna's hands found their way to her head, digging her nails in and burying her fingers in her hair to hold her close.

"Kate, Kate, Kate, it's too good," panted Anna, "I'm going to... You're going to make me..."

"Uhh, Anna, that's so hot," groaned Jack. Kate's gaze darted over to Jack in time to see him push his pyjamas out of the way and take his hard cock in his hand, gripping it tightly as he twisted his hand down its length. He was watching Anna's face intently as Kate continued to stroke inside her and circle her tongue over her clit.

"Yes, yes, Kate, ohh," Anna whimpered before she started to cum, her eyes rolling upwards, chest heaving to show a fantastic amount of cleavage in her cami. Kate's tongue didn't let up the entire time, following Anna's thrusts with her mouth while her fingers stilled inside her. Anna's body shook until she started to come down, gradually relaxing back into the bed. Kate gave her clit one final lick as she withdrew her fingers. She put her fingers all the way into her mouth while she looked over at Jack again. His attention was riveted on her and Anna's on him.

"You look like you could use some help there, Jack," said Anna as she stretched her arms over her head, watching him from under her eyelashes, "you seem to be having something of a hard time."

Jack and Kate both turned to her in surprise.

"I'm impressed, Anna. I didn't even know you knew how to flirt," said Kate, standing up and offering Anna her hand.

"Neither did I. I think it's the orgasm. And probably the whisky," replied Anna while Kate pulled her to her feet, "and I think I might be a tad over-warm."

Kate held onto her hand and brought her close, kissing her lips. Anna could taste herself on Kate's lips and on her tongue when she pressed it into her mouth. Kate's hands skimmed the bottom edge of Anna's cami and brushed the skin that was already exposed below her top. Taking the hint, she slid them under the cami and pulled it up over Anna's head and off. The electricity created between them when their breasts touched was nothing compared to what she felt when she remembered Jack was watching them.

Feeling bold, Anna ran her hands over Kate's ribs, pressing them upwards to cup her breasts. She was mesmerised by the way the nipples seemed to get harder before she had even touched them. She touched her thumbs to the tips of the pebbled nipples and was gratified to hear Kate's intake of breath. She looked at Kate for her approval and took the euphoric glaze over her eyes to mean she could continue.

She pinched the nipples and took her time to pull them towards her, stretching the nipples into a divine pain and letting them spring back to their place on Kate's perfect breasts. She did it again, twisting them as she pulled and enjoyed how it made Kate dig her nails into her hips where she held her. Anna gave them one last tug and then turned her attention to Jack. She took Kate's hand in hers and knelt at Jack's feet, Kate following her down. Jack couldn't help but think that all his dreams were about to come true.

Kate teased Jack, breathing on his cock as she looked up at him and Anna licked up his thigh. As though they were of one mind, they leant closer to him and each planted a kiss on the tip of his cock. While Kate kissed her way down his cock, Anna flattened her tongue over the top and tasted his pre-cum. She flicked her tongue over the tip again and his thigh muscles tensed at the sensation combined with Kate taking one of his balls into her mouth. She sucked gently and ran her tongue back up his dick to join Anna. They kissed around the tip, their tongues dancing over him in unison.

He cupped a hand around each of their heads to encourage them. This time Anna licked down his dick to his balls, Kate following her but taking it into her mouth. When Jack's cock touched the back of her throat and she started to gag, he pressed a little harder on the back of her head. Looking up at him she tried to relax, helped by the feel of Anna's hand caressing her arse, and allowed him to force her head lower and his cock further inside her. When her nose finally met his dark pubes she moaned in pleasure at having managed to take him so completely. His fingers dug into her hard at the sensation it created.

Anna moved to a position behind Kate while she was busy, pressing her tits against Kate's back and using one hand to fondle Jack's balls and the other to stroke Kate's clit. Kate moaned again as she felt her wetness starting to drip down her thighs where she knelt. She could feel every inch of Jack's cock in her mouth and every inch of Anna's body against hers.

Kate sucked Jack's dick hard as she moved her head back up, her cheeks hollowing and her tongue flat against him. She let it pop from her lips before taking it between them again and going as deep as she could. When she repeated it next, Jack held her still and took control to fuck her face.

Anna stroked behind his balls in time with his thrusts, her fingers on Kate's clit keeping perfect time. She was thrusting her hips as well, seeking the sensation she longed for on her own clit.

"This is too much, I need to be inside one of you," groaned Jack, "I want to see you both cum."

"Please let it be me," said Kate, taking Jack's cock out of her mouth and leaning back into Anna while Anna's hands roamed over her body.

Jack moved to lie back on the bed and gestured for Kate to join him while he rolled a condom down the length of his cock. Anna watched in avid fascination from the floor as Kate knelt over Jack and ran his cock up and down her slit, soaking it in her juices, before lining it up with her pussy and sinking down onto him. She saw how his cock stretched her lips and when she heard Kate's cry her eyes snapped up to her face to see the heaven Jack's dick was creating for her painted there.

Kate settled with Jack's cock fully inside her, straddling his hips. He ran his hands up her thighs to her waist, admiring the sight, and then held out his hand to Anna. She stood up, unsure of what he wanted from her before he guided her to stand at the top of the bed and it became clear.

Anna hesitated but then knelt on the bed, straddling Jack's face as she looked at Kate. He stretched up to her pussy and licked there impatiently, looping his arms around her thighs and pulling her down to him.

Kate leant forwards and placed her hands on Anna's knees, thrusting her hips up and down. She closed her eyes while she concentrated on the feeling of Jack's cock sliding in and out of her, aware of the sound of their slapping flesh and the wet noises of Jack's mouth on Anna. She could feel Anna's thighs tensing under her hands as she rode Jack's face.

Kate's eyes opened at the realisation that she was missing Anna's tits bouncing centimetres from her face. She stuck her tongue out and caught the nipple, sucking on it hard. Anna's fingers tangled in her hair again as she pulled her head up to kiss her. Kate suddenly felt Anna's body judder, her whimpers transforming into a moan as she came again. Jack's mouth was flooded with the wetness of Anna's orgasm, his tongue continuing to lap at her.

Anna climbed off Jack and kissed him, her tongue pressing between his lips to taste herself. His chin glistened with wetness which she licked up, savouring the sensation of his stubble on her tongue and lips. She knelt down beside the bed, fascinated by the sight of Jack's cock disappearing into Kate over and over again. She stroked down Jack's body to the point where it met with Kate's and waited there, her thumb poised.

As Kate adjusted the way she was leaning on Jack, she felt his cock get even deeper inside her. On the next thrust, she felt a new burst of sensation where Anna's thumb brushed her clit.

Jack was panting hard, moaning with the effort of not cumming. When he heard the strangled gasp Kate made when she felt Anna, his balls tightened and he knew it wouldn't be long. Putting his hands around her waist he forced her to sit up, his dick as deep inside her as it could get. He lifted her up and pushed her back down onto him hard, impaling her with force. It seemed to break the cool façade Kate had been maintaining.

"Oh, oh, Jack, your dick, yeah, oh my God and Anna, yes honey, oh fuck me, I'm so close," Kate gasped, her litany of swear words and begging continuing until Anna reached up and twisted her nipple hard.

Kate came on a scream, her pussy convulsing around Jack's cock, tightening pleasurably around him as he let go. He continued to thrust his hips as he came, spurting hot cum into the condom.

As Kate rolled off him, he realised how hot he was, a sheen of sweat covering his chest and forehead. Anna pressed a sweet kiss to his hip and he stroked her head as she leaned her cheek against him from her position from the floor.

"I have to admit, that wasn't quite what I was expecting when I came in here," said Jack, breaking the tension. Kate groaned, her arm thrown over her face and her chest still heaving. Jack watched the rise and fall of her small breasts distractedly.

"Didn't you come in here to talk to us about something?" asked Anna.

"I'm fairly sure that if I could think of anything but the two of you I'd get a resounding slap from Kate," replied Jack, glancing at Kate again as she groaned in response.

"I'll be thinking of you for the next week while my pussy recovers from that pounding."

"I aim to please," he grinned, "but I think I'll love you and leave you if you don't mind. My bed is calling my name."

He pressed a kiss to Kate's elbow in lieu of her lips and caressed Anna's cheek as he sat up to retrieve his clothes. As he pulled his pyjamas back on and took the tissue-wrapped condom from the bedside table he watched Anna slide languidly into bed next to Kate. He helped her pull the covers up over them both, feeling oddly paternal, and then snuck out the door. He tiptoed across the living room via the bin and slid on his boots to cross back to his own cabin where he fell into a dead sleep as soon as he collapsed onto his bed.

When Jack opened his eyes there was light slanting in through the slight gap in the curtains. He stretched upwards, smiling broadly at the thought of Kate and Anna's antics last night. The smile slid off his face when he thought of Lily, but that could be a problem for later. He was longing for coffee, a cigarette, and a shower to alleviate the dull ache of his hangover and he slowly stood up, stretching widely again.

His purposeful steps toward the kitchenette stalled when he noticed the sofa was occupied. Lily was folded on the couch reading, her bare legs pouring out of an oversized cable-knit jumper which he bitterly assumed belonged to Ed, and one hand clutching a large mug of coffee. Her face looked fresh and free from make-up and her long hair was piled into an adorably messy bun on top of her head. She didn't stir, seemingly immersed in the paperback in her hands, and he wasn't entirely sure she had heard him come in. He cleared his throat awkwardly.

"Morning, Lily," he said, aiming for a jovial tone to convey how carefree and breezy he was feeling but ending up over-loud in the still quiet, "I thought I could smell coffee. Did you sleep in here, then?"

He watched her eyes continue to track across the page.

"Me too, er, obviously, I mean, where else would I have been?" he chuckled, feeling oddly flustered, "It was a great sleep, I'm feeling very rested. How was yours?"

Again, he was met with silence.

"Right, well, I was thinking of making a pot of coffee if you wanted some?"

Lily finally deigned to look at him, though the look was far from friendly. He suddenly felt sure she knew what he had done and imagined he could see the disapproval radiating off her in waves. An awful feeling of guilt came over him and he had just opened his mouth to continue babbling at her when she said:

"I've got a cup, thanks. Help yourself to the rest of the pot."

"Right, yeah, of course, I said that didn't I. Thanks."

She had already taken her eyes off him but he hovered for several seconds waiting for her to speak again or dismiss him or something before he went to the counter to get the coffee. He retreated into his bedroom as fast as humanly possible, feeling like a cliché for slumping against the door once it was closed.

Taking a sip of the coffee while he stared out the window he mentally brushed himself off from the encounter. What was her problem anyway? It's not like they were a couple. She had gone off with someone else so he had too. And she couldn't even know that anything had happened, so really what was the point in worrying about it? In fact, he had probably imagined the weird vibe between them. After all, they were both hungover and it was still ridiculously early for either of them to be up. And they had argued before so even if she was upset it was probably about that. And maybe she just wanted some space to read her book in peace!

Feeling very much cheered up and almost ready to face the day, he drained the mug and rummaged in his bag for his washbag. He was pretty sure his attitude was verging on jaunty when he emerged into the living room only to find that Lily wasn't in there anymore. All the better that he was leaving then as the last thing he wanted to hear was the two of them fucking. He merrily flipped the bird towards Ed's closed door and left.

Jack opened the door to the girls' cabin without knocking, calling to both of them before he was inside.

"Anna, Kate! Wake up you lazy sods. It's time to make good use of those communal showers and make every camping fantasy come true. Get ready for round 2 because it's going to be wet and soapy!"

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