James and the Troublesome Fucks
Copyright© 2022 by Jake Collins
Chapter 1
Erotica Sex Story: Chapter 1 - James goes on a journey of personal and sexual exploration involving several important people in his life.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa mt/ft Ma/Ma Mult Teenagers Consensual Gay BiSexual Heterosexual Shemale Fiction School Incest Cousins Group Sex Interracial White Male White Female Hispanic Male White Couple Anal Sex Double Penetration First Masturbation Oral Sex Petting Safe Sex
James smiled awkwardly as Amber opened the door of her dorm room to him.
‘Hi,’ said James.
‘Hi,’ said Amber, stepping to one side. ‘Come on in, handsome.’
As he entered, James noticed that Amber had pushed the twin beds together and arranged an assortment of bedding across them.
‘So, you managed to get rid of Sally for the night,’ James remarked.
‘For the weekend, actually,’ said Amber. ‘She’s gone to a family reunion with her dad and she’s not coming back ‘til Monday morning. That’s why I suggested doing this tonight.’
‘We could’ve done it tomorrow,’ James pointed out. ‘Or maybe even Sunday.’
‘No way – the sooner the better!’ Amber laughed, shaking back her long blond hair. ‘I’ve been literally dripping with anticipation for so long, James, and now it’s finally time!’
‘Ha-ha, yeah, I guess it is,’ said James, tugging at the collar of his T-shirt.
‘Just try to relax, huh?’ said Amber, fixing him with an encouraging smile. ‘It’s gonna be fantastic, trust me!’
A tentative knock sounded on the door; James started visibly.
‘Ah,’ said Amber, ‘perfect timing!’
She opened the door eagerly and invited her latest visitor in. James studied the newcomer closely, and found himself staring at a pleasant-looking boy with fairly floppy brown hair.
‘Time for the introductions, I guess,’ said Amber, grinning widely. ‘James, this is Guy, a guy from my economics class. Guy, this is James, a guy who’s studying psychology.’
‘Hey, man,’ said Guy, meeting James’s eye with some nervousness.
‘Hey,’ said James, managing a small smile.
‘Okay, that’s that out of the way, so let’s get down to business!’ said Amber. ‘Oh, no, wait a second – there’s something very important we have to do first.’
‘There is?’ said James. ‘What’s that?’
‘You thought of it, handsome,’ said Amber, ‘and you were absolutely right to. We need to compare sexual histories, to make sure we’re not gonna give each other a ton of horrible diseases. Guy, why don’t you go first?’
‘Um ... okay,’ said Guy. ‘I’ve only ever had one sexual partner – I’ve been with my girlfriend since tenth grade, we were both virgins when we got together, and neither of us has ever had an STI.’
‘Wonderful,’ said Amber, beaming all over her face. ‘James, how about you?’
‘Are you with your girlfriend now?’ James asked Guy.
‘Er ... well, no, not exactly,’ said Guy. ‘We’re on a break.’
‘Me and my girlfriend are on a break too,’ said James, and he and Guy exchanged an empathetic look.
‘James, your history!’ Amber ordered.
‘Um ... okay, yeah,’ said James. ‘Sorry. I had a boyfriend when I was sixteen, we were both virgins when we got together, and we did anal and oral sex. I started having sex with my girlfriend almost exactly six months ago, she was a virgin at the time, and again we’ve done anal and oral.’
‘Excellent – that’s all nice and clear,’ said Amber. ‘So, as for me –’
‘You’ve never had vaginal sex with your girlfriend?’ Guy asked James.
‘No,’ said James. ‘No, I haven’t.’
‘But you’ve had anal sex with her?’ Guy persisted.
‘Very frequently,’ said James.
‘Isabel’s transgender, Guy,’ Amber explained. ‘She identifies as female but she has male sexual organs.’
‘Amber, you’re not supposed to just tell the whole world that kind of thing at the drop of a hat!’ said James, casting her a reproachful glance. ‘It’s Isabel’s personal business.’
‘Sorry, James,’ said Amber. ‘Keep calling me out on this stuff – I know it’s important.’
‘That’s really cool, though,’ said Guy. ‘I mean, it’s great, dude. So, er, you’re like ... what, bisexual?’
‘I’m pansexual,’ said James.
‘Excellent,’ said Guy.
‘I’m glad you approve, man,’ said James, fixing Guy with a wry smile.
‘Anyway, as for me,’ Amber continued, ‘I went for a full screening at the sexual health clinic yesterday, my results came back completely clear, and you can view them on my phone if you want.’
‘I’m happy to take your word for it,’ said Guy.
‘Me too,’ said James. ‘I never wanted you to prove you weren’t riddled with STIs, Amber – I just thought we should all compare notes before getting started, that’s all.’
‘And like I said earlier, you were absolutely right,’ said Amber. ‘So, now we’re done with our comparisons, and given the fact that my birth control pills are fully up to date, let’s fuck!’
Amber had her left arm around James’s waist and her right arm around Guy’s waist, and was kissing each boy in turn for a few seconds at a time. When she judged the moment to be right, she withdrew her arms and removed James’s T-shirt. After kissing him again for a few moments, she turned back to Guy and removed his T-shirt too. Guy also received a shirtless kiss, then Amber stepped back a little and stared at the two boys standing before her in their jeans.
‘My God, you’re both cute!’ she enthused. ‘Jesus, this is even cooler than I hoped it would be!’
Amber giggled and moaned appreciatively as she rubbed both boys’ chests for a while, then she stepped away and removed her own T-shirt and her jeans. As James and Guy watched, Amber crawled onto the bed and assumed a kneeling position.
‘You on this side,’ she said to James, patting the area of bed to her left, ‘and you on the other side, Guy.’
James and Guy obeyed without hesitation. They knelt either side of Amber, who continued to switch the attentions of her mouth and hands back and forth between the two boys. When she was quite ready, Amber removed her bra and threw it to the floor. She then grabbed the back of James’s head with her left hand and the back of Guy’s head with her right hand, and guided them both towards her nipples.
James’s lips encircled Amber’s left nipple and he quickly got to work with his tongue, while Guy mirrored his movements on Amber’s right nipple. Amber’s vocalisations of satisfaction and pleasure were almost continuous as she knelt there with a shirtless boy on each breast, looking more than a little as if she were suckling two oversized babies.
After several minutes of intense nipple work, James felt Amber’s fingers fiddling with the fastenings of his jeans. He continued to work diligently on her left nipple as she extricated his cock and balls and began to stroke them sensually.
‘Very nice, James,’ Amber purred, running her index finger along the length of his shaft. ‘Now, let’s see how nice a pair you two boys really make!’
Amber turned her attention to Guy’s jeans, and soon he too was having his genitals caressed by her eager fingers.
‘Oh my God, this is so cool!’ Amber giggled, as she stroked both boys’ rock-hard cocks in tandem. ‘Okay, let’s lose the pants now!’
James and Guy finally removed their lips from Amber’s nipples and concentrated on ridding themselves of their jeans and underpants. They resumed their kneeling positions quickly, and Amber continued her zealous stroking of their swollen dicks. Her fingers came away slick with pre-cum, as James and Guy both began to breathe more rapidly.
‘Wow,’ Amber whispered reverently, ‘I can’t believe this is all for me!’
‘It’s just the tip of the iceberg, baby,’ Guy assured her.
Amber grinned, then she gave both boys a short, sharp squeeze of the testicles. James and Guy yelled in unison, causing Amber to laugh delightedly.
‘Okay,’ she said, ‘you’ve definitely both earned a dip in the honeypot.’
With that, Amber stopped caressing the two boys and started to remove her panties. James and Guy both watched her closely, their cocks fully erect and throbbing with anticipation. Amber giggled as she slipped her panties over her ankles and threw them aside, then she spread her legs for the boys to enjoy.
James was surprised to see that Amber had divested herself of all her pubic hair. Guy, on the other hand, did not seem at all taken aback at this, so James tried not to let his astonishment show on his face.
‘Guy, you’re up top for now,’ said Amber. ‘I want you in my pussy first, James.’
‘Um ... yeah, sure,’ said James, forcing his gaze away from Amber’s clean-shaven vulva. ‘I mean, my pleasure, Amber.’
Amber laughed, then she took a few seconds to adjust her position on the bed. She ended up lying on her side with her back to James; Guy quickly shuffled up the bed so that his cock was within range of her mouth.
‘I guess this is really it, boys,’ Amber grinned.
‘I guess it is,’ said James.
‘Yeah,’ said Guy.
‘Well,’ said Amber, ‘don’t be shy.’
Guy was only too pleased to accept this invitation; he shoved his cock into Amber’s mouth with unrestrained enthusiasm. Amber made a few vocalisations of approval, then she got to work with her tongue.
James stared at Amber’s hairless pussy, which was nestling comfortably between the backs of her thighs. Swallowing a gulp, he grasped her hips and braced his cock at what he reckoned to be the right angle.
‘I suppose you’ve never fucked a pussy before, have you?’ Guy remarked, though not at all unkindly or maliciously, as he began to move his engorged penis in and out of Amber’s mouth.
‘That’s right,’ said James, ‘I haven’t.’
‘We’ll soon change that,’ said Amber, her voice distorted by the rock-hard meat-pole in her mouth. ‘Go ahead, handsome – I want you inside me!’
James pressed his cock-head to Amber’s protruding labia minora. As he pushed his shaft beyond, he found the way slick and easy to penetrate, yet also sufficiently tight to grasp and squeeze his penis in a highly stimulating manner.
Amber moaned approvingly as James’s cock advanced further and further inside her. When he was in up to his balls, James adopted a determined expression and began a series of pelvic thrusts, which quickly increased in speed and intensity.
‘You’re a natural, man,’ Guy panted, throwing James a grin.
‘Thanks a lot, Guy,’ James grinned back, as he began to pant fairly heavily himself.
James’s mind was soon overwhelmed by the realisation that he wanted to fuck Amber’s pussy as vigorously as he could and for as long as he could, which was exactly what he proceeded to do. Making sure to keep an appropriate level of attention on what her mouth was doing to Guy’s cock, Amber reached down and started to rub her clitoris with two fingers. James again found his knowledge and understanding of girls entirely insufficient to comprehend Amber’s actions in relation to her private parts, but as he had every reason to believe that she was enjoying what he was doing, he continued to fuck her for all he was worth.
‘Oh, yes,’ Amber moaned, as her fingers began to move even faster on her clit, ‘fuck me, James!’
James was pleased to hear Amber confirm that his presence inside her was still welcome; he renewed his efforts accordingly. Amber screamed in sexual ecstasy, which invigorated James even further. He grasped her left leg under the knee and pulled it back slightly, so that he was able to peer over and see his cock sliding rapidly in and out of her pussy.
James’s eyes widened at the sight, and he began to vocalise his sexual excitement quite loudly. He moved his hands so that they were cupping Amber’s buttocks, and his pelvic thrusts built to such a level of intensity that the bed began to groan and creak in protest.
Guy chose this moment to release a huge load of spunk into Amber’s mouth. Amber coughed and spluttered, and some of Guy’s sperm trickled out of her nose, but she quickly pulled herself together and swallowed as much as she could. As soon as she had consumed the final drop, she screamed her way through a highly intense orgasm of her own, her fingers still working overtime on her clit.
After watching Guy and Amber in the throes of sexual rapture, and having felt Amber’s intense orgasmic contractions against his own cock, James finally had to give in to the inevitable. He squeezed his eyes shut and roared as he released his seed inside Amber’s pussy. Still fighting to recover her breath after her own orgasm, Amber laughed in delight as James ejaculated unrestrainedly inside her.
As the final spurt of cum burst from the tip of his penis, James experienced a sudden moment of panic that Amber might have forgotten to take her birth control pills after all, or that they might not work even if she had taken them. He banished this thought from his mind as quickly as he could, and withdrew his cock from Amber’s slit.
James barely had time to draw breath before Amber had wriggled onto her other side and placed her lips around his cock-head. He was still hard despite his recent orgasm, and the same was true of Guy, who was already entering Amber’s pussy from behind with undisguised delight.
Again, Amber very soon started to provide herself with clitoral stimulation, which reassured James that he himself had not been doing anything wrong in that area. Guy was going absolutely crazy on Amber’s snatch, but James was almost certain that Amber was devoting more oral attention to his own dick than she had to Guy’s, which made him feel quite special.
Amber took a moment to remove her mouth from James’s throbbing cock and grin up at him, masturbating him steadily all the while.
‘Do you think you made the right decision to come here tonight?’ she asked him.
‘Very much so,’ said James, struggling for breath slightly.
‘I think so too,’ said Amber. ‘Do you like it when I jerk you off like this?’
‘God, yes!’ said James, exhaling heavily.
‘Did you like it when I was giving you head just now?’ Amber purred.
‘Yes!’
‘And I know you liked fucking my pussy.’
‘I sure did!’
‘So what was all that back-and-forthing before you agreed to do this, then?’
‘I ... I can’t really talk about that right now,’ James panted.
The room was suddenly filled with a series of deafening vocalisations as Guy spurted out his second orgasm of the evening. Amber looked slightly put out for a moment, then she turned her full attention to jilling herself off with her left hand whilst jacking James off with her right hand.
Guy wrenched his cock out of Amber’s pussy and collapsed onto his back, panting heavily. As Amber shrieked her way through her second orgasm, James watched her right hand dedicatedly jerking his cock; his breathing became more and more rapid by the second.
As soon as she had finished vocalising her own intense pleasure, Amber returned the attention of her lips and tongue to James’s eager shaft, which caused him finally to blow his load for the second time. James gasped and moaned as Amber swallowed an enormous volume of his semen, then they both flopped onto their backs alongside Guy.
‘That was truly wonderful, boys,’ Amber said a short time later. ‘But before either one of you gets inside me again, you have to get inside each other!’
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