Level Up - Cover

Level Up

by Jake Collins

Copyright© 2022 by Jake Collins

Erotica Sex Story: As Dylan and Dennis make significant progress with Tammy and Tara, Max and Lucie come to a decision about their future together.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   mt/Fa   Teenagers   Consensual   Heterosexual   Fiction   Group Sex   Interracial   Black Male   Black Female   White Male   White Female   White Couple   Masturbation   Oral Sex   Petting   Safe Sex   Squirting   .

Dylan and Dennis were sitting side by side at the foot of Dylan’s bed, both completely naked and with their cocks in their hands. They were staring intently at Dylan’s laptop, which was on the corner of his desk nearby. An image of Tammy and Tara, also naked and digitally stimulating themselves, was the sole focus of the boys’ attention. As the four watched each other masturbating furiously, they all began to let out vocalisations that indicated imminent orgasms.

Dennis came first, spraying a huge amount of his semen across the area of Dylan’s bedroom floor between the desk and the bed, followed by Tara, who climaxed noisily and wetly with her eyes glued on Dennis. Tammy’s orgasmic screams quickly joined the cacophony, then Dylan came too, emptying his balls in several powerful spurts and swelling the lake of boy juice on the carpet that Dennis had started off.

‘Wow,’ Tara panted, ‘that was pretty spectacular, huh?’

‘It was excellent!’ said Dennis.

When everyone had recovered their breath and gathered their composure a little, they all exchanged grins.

‘I really like all your posters of various aircraft, Dylan,’ said Tammy.

‘Oh,’ said Dylan, glancing over his shoulder, ‘you can see those, huh? Yeah, I’ve been interested in planes and stuff since I was about five.’

‘Sometimes he makes me play flight simulation games with him,’ said Dennis.

Tammy and Tara giggled.

‘Every time we think you two can’t possibly get any cuter,’ said Tara, ‘you prove us wrong!’

‘I want to train as a commercial pilot after I finish school, Tammy,’ said Dylan.

‘That’s great, Dylan,’ Tammy beamed.

‘Listen, guys,’ said Tara, ‘we really want to come to California and get together with you in a couple of weeks, sometime between Christmas and New Year’s. Any chance you could make it to that hotel at Half Moon Bay again?’

‘Are you kidding?’ Dennis laughed. ‘We’ll make it no matter what!’

‘As long as you’re both absolutely sure you’re comfortable with the arrangement,’ said Dylan.

‘Yes, we’re both absolutely sure,’ said Tammy, treating him to a warm smile. ‘After all, we’re in too deep now to worry about that kind of thing, aren’t we?’

Dylan looked down at his cum-spattered carpet and said, ‘Yeah, I guess we are.’

‘We’ll be in touch soon with some possible dates,’ said Tara.

‘Great!’ said Dennis.

‘Ciao for now, then,’ said Tammy.

The boys nodded and adopted slightly bashful expressions, then they waved goodbye in perfect unison. The girls giggled again before Tara disconnected the call. Dylan and Dennis looked at each other with expressions of elation on their faces.

‘Adam’ll give us a ride,’ Dylan said confidently.

‘Thank heavens for Adam,’ said Dennis.

‘Yeah,’ said Dylan. ‘Den, you know how we were having cyber sex with Tammy and Tara just now?’

‘I sure do, Dil!’ Dennis grinned.

‘Did you notice that they were stimulating their clits?’ said Dylan. ‘Only their clits, I mean – not their vaginas. Like, they didn’t insert any fingers or toys or anything.’

‘Toys?’ said Dennis.

‘Yeah, you know,’ said Dylan. ‘Dildos, vibrators... ‘

‘Hmm, I guess I did notice that,’ said Dennis. ‘It doesn’t really match up with what those websites seem to imply.’

‘I hope the girls actually want us to fuck their pussies,’ said Dylan. ‘I mean, I want to make Tammy come by stimulating her clitoris, but I want her to want my dick inside her as well.’

‘They seemed to enjoy having our dicks in them,’ said Dennis. ‘But yeah, they needed their fingers to come, didn’t they? Or that grinding motion they did the first time. Girls are complicated, dude.’

‘They sure are.’

‘How about we concentrate on something else for a while? I’ll set up a two-player on your TV, shall I?’

‘Excellent idea, buddy,’ Dylan beamed. ‘I’ll go get us some Sunny D while you’re doing that.’

‘Wonderful,’ said Dennis.

Dylan rose to his feet and used a corner of his duvet to wipe the last remnants of his recent ejaculation from his swinging glans, then he crossed the room and pulled on a pair of sweatpants.

‘Any particular flavour you’d like?’ he asked.

‘Surprise me,’ Dennis replied.


Dylan and Max met in the kitchen, both wearing no shirt and sweatpants; Max was clearly about to leave with two glasses of Sunny Delight. Dylan smiled at him, Max smiled back, then they passed in the middle of the room as Dylan headed for the fridge.

‘Ooh, Max!’ he suddenly exclaimed, slamming a bottle of Sunny Delight onto the worktop as he spoke. ‘Wait a second, will you?’

He swung round just in time to see Max disappearing through the open door. Cursing himself for his carelessness, Dylan took off in hot pursuit and managed to stop his quarry in the hallway by grabbing his arm. After making a skilful and successful attempt not to drop his Sunny Delight, Max turned to face Dylan.

‘Sorry,’ said Dylan, smiling sheepishly.

‘That’s fine,’ said Max, fixing him with a reassuring look. ‘Is there something I can do for you, Dylan?’

‘Max,’ said Dylan, ‘we’re friends, aren’t we?’

‘Of course we are,’ said Max.

‘Close friends?’

‘I’ve known you since you were a toddler and we’re gonna be brothers-in-law in the fairly near future. You can’t get much closer than that, can you?’

‘No, I guess you can’t,’ Dylan laughed. ‘So we must be close enough that I can ask you for some advice.’

‘If you feel comfortable to, I’d be glad to give you any advice I can,’ said Max, sounding both pleased and surprised.

‘Sexual advice?’ said Dylan.

‘Sure,’ said Max. ‘Although seeing as Lucie represents my entire catalogue of sexual experience, are you sure you want me to advise you on that particular subject?’

‘Yes, I do,’ said Dylan, ‘so long as you keep it general.’

‘Of course,’ said Max. ‘Are you, er ... are you planning on popping your blueberries some time soon, then? Oh my God, that was such a personal thing to ask! I’m sorry, Dylan.’

Dylan thought for a moment, then he said, ‘You won’t tell Lucie anything I tell you about myself, will you? Or anyone else, for that matter.’

‘I promise I won’t tell a soul,’ Max said solemnly.

‘I already popped my blueberries last summer,’ Dylan admitted, ‘and I’m hoping to have sex again – with the same girl, I mean – in a couple of weeks. I know I’m two years illegal ... and she isn’t illegal, as it happens ... and I know you and Lucie took a while longer than that to get together ... so I guess maybe you don’t approve of me.’

‘I’m not here to judge you, Dylan,’ Max said with a smile. ‘But if you want to know my opinion, I popped my blueberries pretty soon after I turned nineteen and you popped yours pretty soon after you turned sixteen, which I think are both perfectly reasonable things to do under the right circumstances.’

‘I think so too,’ Dylan smiled. ‘Max, do you know anything about the clitoris?’

‘Yes,’ said Max. ‘Yes, I do.’


‘Wow,’ Dylan said a little while later. ‘That was ... detailed, Max.’

‘When it comes to women’s orgasms,’ said Max, ‘details are very important.’

‘I’m beginning to see that,’ Dylan nodded. ‘Wow, Dennis said he wanted me to surprise him, but ... So what’s the best way to combine vaginal penetration with clitoral stimulation?’

‘There’s no right answer to that question, Dylan,’ said Max. ‘Different people like different things. You have to try stuff out together and see what works for you as a couple.’

‘Okay,’ said Dylan, ‘but what’s your own personal favourite way of fucking a girl’s pussy and stimulating her clit at the same time?’

‘Even bearing in mind the extent of my own personal experience?’

‘Yes!’

‘I’ll tell you,’ said Max, ‘but there’s no guarantee it’ll work so well for you and your partner. Still, here’s how it goes... ‘


Max and Lucie were sitting side by side on the edge of Lucie’s bed. Due to the fact that Lucie was jerking him off energetically, Max was largely oblivious to the rest of the world. Lucie had been watching Max’s facial contortions with keen scrutiny, then suddenly her gaze fell upon the two drinking glasses on her nightstand.

A contemplative expression crossed Lucie’s face and her hand stopped moving. As he was dribbling copious amounts of pre-cum and had been extremely close to blowing his load, Max looked at her with a pained expression.

‘Please, Luce,’ he panted, ‘finish me off!’

‘Hmm?’ said Lucie. ‘Oh, sorry babe. I was just wondering why it took you so long to bring our Sunny D up from the kitchen.’

‘I stopped to have a conversation with Dylan,’ said Max. ‘He asked me for some advice; I was really touched.’

‘Oh, cool,’ said Lucie. ‘Boys’ stuff, was it?’

‘Very much so,’ said Max.

‘In other words,’ Lucie grinned, ‘you were teaching my sixteen-year-old brother how to have sex, right?’

‘Um ... yeah, I guess I was,’ Max admitted.

‘In which case,’ said Lucie, grasping Max’s testicles in her palm and massaging them roughly, ‘you must’ve been teaching my sixteen-year-old brother how to have sex with me!’

‘No, Luce!’ Max gasped. ‘I didn’t get that specific! I mean, I did give him my own personal view on something, but it was really just general advice he was after. God, that feels good! You can squeeze a little harder if you want to. Oh, Jesus... ‘

‘I guess you’re used to dealing with kids at the surf and racquet club,’ said Lucie.

‘Yeah, I am,’ said Max. ‘Although they don’t ask me about sex.’

‘You’ll make a really great dad someday, Max.’

‘I sure hope so.’

‘How would it be,’ said Lucie, digging her fingernails into Max’s balls as she squeezed and rolled them vigorously, ‘if when we’re married and all moved in together, we start trying to have a baby? Or at least we stop trying not to have one.’

‘I’d love that, Luce,’ Max beamed at her. ‘I’d love that so much! But only if you’re absolutely sure you’re ready.’

‘I really think I will be,’ said Lucie. ‘I guess we can’t know anything for certain right now, but ... well, I do know that I want to have your kids someday, Max. But today, I just want to see them fly!’

With that, she abandoned his balls and started pumping his cock at an incredible rate. Max’s eyes opened wide as he gasped and moaned with pleasure. Within ten seconds, Lucie had jerked him to orgasm. Max’s entire body shuddered and his breath came in ragged gasps as he shot several arcs of spunk across Lucie’s bedroom. Lucie laughed delightedly at the spectacle.

After Max had panted his way back from the realms of sexual ecstasy, he fixed Lucie with a wry smile and said playfully, ‘You might’ve warned me, Luce.’

 
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