A Cabin with Friends

Madison's mouth returned to Thomas, and for several minutes he and James proceeded to slowly impale her from both ends. Panting and moaning around Thomas's hardness, she quickly found she could no longer focus both on her own work and the pleasure being doled out from behind. Her breathing grew faster and more urgent and she felt the need for release rise within her. Then, after several more moments passed, moments that seemed like an eternity, her panting turned to a low growl, and in a shaking voice broken words escaped her lips, "I'm going to cum".

Madison's moans now turned feral, her hips bucking backwards harder than before against her friend. Her legs, already spread wide open, urged James to fill her faster and harder. He more than willingly obliged, but soon approached his own point of no return. His words cutting through the otherwise peaceful night, "Madison, I want to cum with you, can I cum inside you?".

Lost in the moment, Madison looked over her shoulder at her friend, and in an almost pleading voice responded, her hips pushing back even harder to reinforce her answer. "Fill me with your cum, I want to feel it inside me", she demanded.

James needed no further persuading, and as he felt Madison tighten around him, her own climax finally arriving, his body began to shake. Madison, still at this point stroking Thomas had to let go of his thick cock, unable to focus on him at all anymore. Instead all of her focus was now on her own release and the simultaneous sensation of James's warm seed invading her depths. Her moans pierced the night, Thomas watching as two of his closest friends reached climax together.

Another moment passed before Madison's head cleared and she felt James slide from within her, his speed spilling into her panties. Closing her eyes for just a moment as she relished what had just occurred before the now deafening silence was broken.

"Damn, that looked fun. Does this mean I don't get a turn?" Thomas's voice disappointedly asked. Although laughing under his breath as he said it, Madison knew it was a serious question on his part.

Looking back up at Thomas from her position still on her knees and biting her lip, Madison collected herself before responding. "I'm down if you are. But under one condition! I need to be in control. You're really fucking big and I don't want you tearing me in half!" Again, although said in a joking way, all present knew there was some honesty to the words.

"Well, I have thought about you riding me on more than one or two occasions over the years, so that sounds like a deal to me." The quick response came, a sly smile painting Thomas' face. "Now come here." He added, extending a hand to Madison as he stepped backwards and sat down on the bench he and James had previously been sitting on.

Thomas's approach was somewhat different than James's had been. As Madison rose from her knees and stepped toward her friend, his fingers moved to her cheeks and ran gently through her hair. He guided her to him, urging her to his lips, a warm and deep embrace following. Thomas was being far more sensual and tender than James had been; the way he kissed and the way his hands moved over her body felt far better than Madison would have ever expected; Thomas was caressing her like a lover rather than just a friend he was bedding. And with that, the remaining apprehension Madison had about being with Thomas dissolved.

Standing between Thomas's legs, Madison became lost in their embrace, the sweetness of his lips adding to her arousal. His hands slowly trailed down her body, teasing over her fabric covered breasts then along her sides to her back. Next her dress lifted, Thomas's hands pulling it upward from behind. His hands then disappeared underneath, cupping his friend's ample backside, pulling her closer. The same hands then proceeded to loop into her panties and urged them downward. Ever so slowly they moved down over Madison's hips, followed by her thighs. Then as they fell down her legs, she lifted one foot then the other, allowing the soaked undergarment to fall to the ground, freed of their purpose. Thomas's hands travelled along Madison's inner thighs now, fingertips teasing their way upward as the two continued their embrace. In response to his touch, Madison's own hands moved down Thomas' body, her fingertips ever so slowly tracing toward his thick and incredibly hard manhood. She then slowly wrapped both hands around him, gently stroking.

Repositioning herself, Madison maneuvered to straddle one of Thomas's legs, slowly grinding as they continued kissing. For his part Thomas's hands moved to his partner's shoulders, lowering the thin straps of her dress one at a time. As these fell limp he pulled away from their long kiss and shifted his focus, his lips and teeth ever so gently kissing and biting along her cheek, her neck, along her collarbone, then along her now exposed upper chest.

Madison's excitement was reaching new heights, her renewed arousal coupled with James's recent discharge dampening her thighs and Thomas' leg. Knowing it was now or never, she shifted, repositioning herself over Thomas. She then began slowly grinding herself along his large member, her hand serving as a guide.

As engrossed in the moment as she was, she had momentarily forgotten James's presence, the feeling of Thomas's hands and lips on her body, and the thickness of his cock in her hand being her sole focus. She was therefore shocked when a second set of lips began to kiss her neck from behind, an accompanying set hands reaching around her, gently cupping her breasts, teasing nipples between fingers.

"You want to feel that giant cock deep inside your amazing little pussy don't you?" James whispered into Madison's ear from behind. "He's going to love the feeling of being inside you. He's always wanted you."

James's words coupled with Thomas' soft and sensual touch made Madison purr. She was still however a bit apprehensive due to her lover's size. "Thomas, please be gentle, I'm going to need you to go slow," she begged, lifting her hips up. With Thomas still in her hand she now ran his thick head along her entrance.

"This should help." James interrupted, kissing his way down Madison's body to Thomas's cock waiting at her entrance, adding extra wetness with his mouth to the swollen head before pulling back away and licking his lips.

Taking her cue Madison slowly lowered herself. Immediately she felt herself opening wide, Thomas's thick head disappearing into her. A loud gasp escaped her lips as she worked her way downward. While not in pain exactly, a look of slight discomfort spread across her face as more of Thomas filled her. Concentrating, she closed her eyes, telling herself that she needed to make this work. Slowly she grinding her hips, hoping her body would loosen up as she became more comfortable.

Seeing his friend's nervousness, Thomas's voice now spoke reassuringly, causing Madison's eyes to open. "Mads, just go slow. There's no need to rush. I want this to feel good for you. Don't force it, just take your time and let your body get used to it."

Looking down at her friend, Madison saw a genuine look of concern on his face. Despite the feeling that she was being stretched beyond her limits in that moment, she couldn't help but feel Thomas's authentic care for her pleasure and wellbeing to be the sexiest thing imaginable. She also knew he was right; it was like losing her virginity all over again, she just needed to relax and take it slow.

Adopting a new approach, Madison took a break from lowering herself around her friend, only a third of his member yet inside of her. Instead she leaned forward and began to kiss him deeply, her hands on his chest to brace herself and her hips ever so barely moving. While the two kissed James too continued playing, his fingertips tracing along Madison's chest, down her arms and hands, then over Thomas's body. He then joined the others' mouths, the three friends taking turns kissing one another.

For several minutes this continued before Madison finally began rolling her hips once more, confident her body was now able to accommodate Thomas's size. Despite being fuller and more stretched than she ever had before, she had to admit to herself, she was beginning to thoroughly enjoy the feeling. Her walls were feeling every ridge and vein of her friend's cock and she could swear she could feel him pulsing inside her. It felt incredible.

Sensing Madison's growing comfort, Thomas began to slowly thrust upward to meet each of his friend's movements, the feeling of his friend's heat utterly intoxicating around him. James, still running his hands over the others' bodies began to coach Madison now, whispering slyly into her ear. "You know you can take more; I bet your little pussy loves being stretched by such a big cock. He's been into you for as long as you've known each other. I remember him telling me how much he wanted it to be you as I sucked his cock. You're making his biggest fantasy come true right now."

The words being spoken only served to excite Madison further, and her resolve to pleasure Thomas grew stronger, taking more of him with each rhythmic merging of their bodies. She had indeed been unaware of her friend's feelings towards her until that night's encounter, and that knowledge only added to her pleasure, for she too had harboured similar hidden feelings for a long time.

While the depth of the penetration into her womanhood increased, so too did Madison's pace, and she knew she was once again climbing toward the precipice of release; her body's steady climb to climactic euphoria had begun. And she already knew this time was to be different. While still not quite at the point of no return, the pressure was somehow more pronounced than ever before, the intensity different. She knew that when she finally did release, it was going to be incredible.

As Madison focused on the warmth slowly building inside her body, James continued to whisper into her ear, his hand beginning to trace down her back, fingers teasing their way lower and lower. Soon she could feel his hand along her bottom, accompanied by what was at first an unfamiliar feeling. She soon clued in however as she realized he was stroking his cock against her, once again fully engorged. Knowing what James was thinking and in many panicking at the thought, she turned her head to him, and through increasingly heavy breathing spoke with broken words "No... it's too tight; you're too big" she began, for a moment seemingly dashing his plans, before finishing, "not without proper lube".

With Madison still looking over her shoulder at him, James then put his lips to hers, kissing her softly before pulling away, a devilish grin spreading over his face. "You don't think I came prepared Madi? You know me better than that", he said, pulling a small plastic packet from his pocket.

"Ok... But please be gentle. I've only done that a few times." Madison submitted, both excited and terrified at the prospect of what was to follow.

Having committed to James' plan, Madison once again returned her attention to Thomas, leaning in and kissing him deeply, now fully comfortable with the feeling of her womanhood stretched around him. Breaking the kiss, she spoke, her voice now a feral growl, driven by the need for release growing in intensity within her, causing Thomas to smile broadly. "You feel so fucking good; you're going to make me cum all over that beautiful cock of yours."

As Madison continued to ride Thomas, she once again felt James behind her, now preparing himself; she could already feel the heat emanating from his manhood. She then took a deep breath and slowed her movements around Thomas until she was resting perfectly still. Thankfully James was skilled with what came next and took his time, ensuring not to rush. First, a single finger slowly massaged her rear entrance, then the feeling of warm lubrication joined it. Finally she felt herself being slowly and carefully penetrated by the digit, just the tip exploring. James then began stroking himself against her, the sound of lubrication being applied being the only sounds other than her and Thomas's hard breathing. From behind Madison, James whispered softly, his voice much softer than it had been the rest of the night. It was clear to her that he could feel her trepidation. "Lean forward a bit Madi, give Thomas a big kiss for me."

Madison did as instructed, leaning forward more than she already was and kissed Thomas deeply, his hands moving between them and slowly rubbing her clit. She then felt James's hand on her bottom, positioning himself for his invasion. Then she heard James speak once more, his voice again soft and caring. "Are you ready Madi?" While nervous, she knew it was now or never and she'd never be more ready than at that moment. And so, with that, she nodded her approval, continuing to kiss Thomas deeply as she did.

What followed wasn't exactly painful but not entirely pleasant either at first. As the swollen head of James's cock slowly entered her, Madison could not help but give a silent thanks to the fact her friend had been prepared and had lubricant readily accessible. To her further relief, the initial discomfort that had existed subsided considerably as the rim of James's manhood finished piercing her and she conformed to the girth of his shaft. That, and James's addition of the last drops of lubrication to the point their bodies joined really served to change the feeling from one of discomfort to one or pleasure. And she really did have to admit to herself, it did feel good, albeit in a very different way than she was used to.

"Are you ok?" James asked, both the bodies of his too partners and his own remaining completely still at that moment, apart from his slow push forward.

"Yes, I think so. But go slow." Madison urged, her tone almost pleading,

With consent granted, James and Thomas gave each other a subtle nod. James then proceeded to take the lead, steadily pushing himself deep inside Madison before retreating and ever so slowly repeating his motions. Madison winced as her friend did this, leaning into Thomas to bite his shirt while clawing at his chest. Again, while not painful per se, the pressure was something Madison was wholly unaccustomed to and she struggled at first to accommodate her friend from behind.

"You're doing great babe. We'll make sure we're gentle, just tell us to slowly down or stop if you need us to." Thomas urged.

Putting on her bravest face, Madison then nodded, responding in short bursts. "It... Feels...Good...It's just so much... Pressure... I'll be ok though."

Smiling, Thomas moved the hair that was now falling across Madison's face from her cheeks, looking deep into her eyes. Knowing his friend was not yet ready for him to proceed with his own movements into her, he then raised his fingers to her mouth. "Get them wet for me."

Doing as instructed Madison took two of Thomas's fingers deeply, continued looking him in the eyes and sucked on them suggestively. She then released her lips, ensuring they were thoroughly soaked. Smiling, Thomas proceeded to shift himself, allowing his hand to once again reach between himself and his lover. Madison then felt his wet fingers run along where his still swollen cock rested inside her, then forward, massaging her swollen clit.

Almost immediately Madison began to purr once more, the feeling of both her holes filled and a skilled hand on her clit nearly overwhelming her. Instinctively her body began shifting backward and forward to meet James's slow thrusts; the pressure deep within her had now begun to take on a different form, evolving from the edge of pain to complete pleasure. These new movements also caused Thomas to stir, as in her renewed movements Madison was once again stroking his girth. Confident in his friend's ability to handle both himself and James, Thomas now because rolling his hips, his thickness slowly pressing in and out of Madison from below as he moved.

Madison was enraptured by the feeling of having two men in her at the same time. It was different than she thought it would be, but she had to admit, it felt amazing. Together the three lovers progressively moeved faster until they found the perfect rhythm, one that allowed Madison's body to take both of her friends' throbbing cocks deeply while equally filling her own needs perfectly. Madison's breath now again began to grow quicker, and she realized she was approaching the point of no return again. Ever since Thomas had first entered her she had been looking forward to this release, but with the additional stimulation now added she was sure she would explode.

Sensing a change in Madison's needs, her two friends each resolved to add to her pleasure even further. James, still behind and slowly pumping himself in and out of her rear entrance proceeded to place one hand on her lower back while at the same time reaching forward, grabbing a handful of hair. He then proceeded to pull Madison's head back, perhaps a little bit more roughly than he had planned, causing her body to become more vertical than it previously had been. On Thomas' part, he leaned in and pulled the top of Madison's dress further down, fully exposing her breasts for the first time. With a hungry look in his eyes he zeroed in on his target, running his tongue over one of her stiffened nipples then proceeding to suckle upon it with his lips. At the same time his free hand reached up, expertly maneuvering to the other breast, kneading it while rolling its nipple between his fingers. And last but not least, with Madison's new position, Thomas' other hand, the one already massaging his friend's clit, gained improved access. He now ran this hand lower to where his cock was impaling his friend and brought more of her now freely running honey to her clit, resting his palm upon her mons and using his thumb to stroke her swollen button, far more deftly than before.

Madison was now in complete and utter ecstasy and began to feel her legs weaken; she was now at the point of no return. While up to this point she had tried her absolute best to keep quiet, she could no longer contain herself. She was beginning to cum harder than she ever had before and didn't care if the whole world knew it; she needed release. Deep and loud feral moans now escaped her lips while at the same moment her body tensed and she felt herself grip around Thomas, letting her feel every ridge of his glorious manhood even more than before. Thomas too felt this and in an instant it became too much for him to bear. Moans likewise began to escape his lips as his hardness spasmed and his release began.

For what seemed like an eternity Madison and Thomas came together, their moans shattering the otherwise silent night, Madison's incredible tightness milking every drop of her friend's seed. As their joint climax finally subsided Madison then felt James come to a stop behind her and his hand move to the base of his still throbbing cock. Slowly she then felt him begin to very slowly extract himself from her, massaging her rear entrance as he retreated. Once no longer in his friend James then stepped forward to be next to Madison, still massaging her forbidden entrance with one hand while reaching to his cock with the other. For the first time she now realized he had used a condom while inside her, one he proceeded to now remove and throw into the still burning fire. "Getting rid of the evidence!" He remarked, smiling.

"Thank you for wearing that... for that..." Madison gratefully but somewhat awkwardly uttered, her head still reeling as her body calmed.

Smiling, James put a hand in Madison's hair once more and leaned in, kissing her deeply. Thomas then joined as well, and as they kissed it became clear that James was not yet finished as his friends could feel and see he had his cock in his free hand and was continuing to pump it vigorously.