Accidental Penetrations Ch. 01

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Very important note: I’ve always loved accidental penetration stories even if they’re usually not realistic. And so this is a very lighthearted story. It’s not meant to be an accurate representation of something that could actually happen in real life! On the other hand, around that highly improbable incident, I’ll try to make the story as interesting as I can. If that’s not your cup of tea, find another one of my stories.

Edited by: Pope1944. Thanks!


As Dustin watched his older sister, he sighed. From his room he could see her packing her suitcase in her own room across the hall. Erica was gorgeous and voluptuous, her fully developed curves were barely hidden in skin tight jeans and a tank top. He knew that all of his friends would have killed for a chance to see her naked. For a long while he would have done the same. But not now. You see, Dustin has already seen her naked. Gloriously naked.

Better yet, he knew that he would be seeing her naked again. And not for a few stolen moments, nor with a hidden camera in the bathroom. Oh no. Once more he was going to see her nude with his own eyes, from up close, with her being fully aware of his presence for days. He could still remember the first time he ever saw his older sister Erica naked.

A year ago, Dustin’s parents called a family meeting. They were all there: his older sister Erica, his two twin sisters, Emily and Lily, as well as his two parents and himself. After dinner, their mother had talked to them about the possibility of going on a comping trip next summer. A nudist camping trip. There was a long silence.

Dustin remembered looking around at his three sisters’ faces. Erica was already living mostly at her apartment next to the college she went to and didn’t come on most family trips anymore. After their mother’s announcement, she merely frowned and was obviously surprised. The twins were grinning, clearly convinced that it was a joke. As for Dustin, all he could think about was seeing his three lovely sisters’ naked bodies. He was grinning, but for an entirely different reason.

To Dustin’s surprise, Erica had broken the silence and said that she was willing to give it a try. Dustin had then followed suit. And so all eyes had then turned on the twins who suddenly realized how serious this proposition was. Stunned, they shared a long look and seemed to talk to each other telepathically for a moment as they sometimes seem to do. They then smiled, nodded at each other and said “Yes!” in unison.

And so a couple of months later the entire family had spent an entire week completely in the nude in a remote colony. To Dustin’s surprise, he acclimated very quickly to the peculiar situation. Granted, he spent most of the first day having to hide his erection from his naked sisters. Thankfully, they were very gracious about it.

Dustin guessed that their mother had been very clear about not teasing him about it. What shook him the most was just how arousing the sight of his mother’s breasts were. The twins had pairs of surprising breasts on their very thin frames and Erica had large, voluptuous breasts, but Dustin’s mother had more than all of them put together! But that’s a story for another time.

In the end they loved the week so much that they vowed to take at least one such trip every year. Even if the colony had decided to forbid cellphones and computers along with clothes. Dustin was still happy to see his older sister pack. Despite the entire family’s comfort at being nude at the colony, it had never really been an option to become full time nudists. That meant that Dustin hadn’t been able to enjoy the sight of his sisters’, or mother’s, bodies since last year. That was about to change. As he was thinking about that, Erica turned and looked at him. She smiled and shook her head, as if divining what he was picturing in his mind. “Pervert…” she joked.

Dustin smiled and returned to his own suitcase. Packing for a nudist colony was not the same as for other trips, but they still needed to bring plenty of stuff. As he placed his laptop in there, he heard one of his twin sisters laughing out loud. In the room adjacent to Dustin’s the two twins were also busy packing. At eighteen years old, even if there was a spare room in the house, they still shared a room and neither wanted to change that.

Dustin had heard rumors that they had also shared lovers, some with their consent and others as a secret thrill for the girls. He didn’t know if it was true, but Dustin certainly suspected that they often shared a single bed. What they did, all alone under the blankets, he had no idea. His imagination was eagerly conjuring up images of some possibilities, but honestly, he didn’t think reality matched up to his fantasies.

If they weren’t as voluptuous as their older sister, the twins had remarkable bodies nonetheless. They were both very thin and for most of their lives they had looked like celery twigs. Thankfully, and to Dustin’s pleasure, their poker oyna breasts had developed seemingly overnight two years ago. And despite the fact that they came up pretty late, they certainly developed with a vengeance!

Still very thin, the twins now had breasts that looked like bubbles of perky flesh on their chests. If,in absolute terms, they were small, on their small frames they looked stunning. “Well…” thought Dustin, remembering his older sister and his mother’s breasts. “Maybe I have a skewed reference for what a small breast is. Each of those four identical breasts would fill my hands easily!” Dustin was feeling good as he finished packing, knowing he would soon be presented with a feast of eight breasts as well as four sweet asses and pussies for the coming ten days!

Come to think of it there would be quite a few more as two of his cousins, two other beautiful girls, would join them later during the week! Dustin had been half in love with Milana, who was about 7 years older than he was, ever since he was a little boy. Dustin’s mother had confirmed that she would be there, along with Indiana, the girl everybody knew was an adopted Irish girl. Yet Dustin’s uncle, pointing to a few red hairs in his beard, swore that she was his.

Dustin wished that the third cousin in this family, Katee, would join them as well. But Katee was a very shy girl that has struggled with weight all her life. He just couldn’t see her coming to a nudist colony. He hadn’t seen her in over a year since her family moved to another state, but they exchanged emails more or less regularly. Then again, the thought of seeing Milana and Indiana naked made up for his disappointment about Katee.

The next day, after a long 8 hour drive, the entire family arrived at the colony. It was a huge community of people, some of which had come from much farther than Dustin’s family. While some came with RVs and others slept in tents, Dustin’s family had rented three rooms in the big lodge.

Obviously their parents would take the room with a queen bed and the four siblings would share two rooms with two single beds each. To everybody’s surprise, Dustin would not share a room as Erica as they had last year. Emily said that she wouldn’t mind sharing a room with Dustin for a change. When she said it, she leaned against him and hugged him. He was puzzled about her decision, but didn’t think much of it because, in any case, he would see her naked every single day for an entire week!

For Dustin, the first day turned out to be a repeat of last year’s first day with his cock feeling like a kid in a candy store. The four women in his family were beautiful and sexy enough, but there were also a lot of other girls and women at the colony. The majority of them were not all that desirable, but enough of them were to cause Dustin some adjustment trouble.

Late on the first day, he found himself in semi-darkness in his room, staring at the nude form of his younger sister. It was warm enough that she had decided to sleep without a blanket. And without clothes, obviously. On his side, convinced that Emily was sleeping, Dustin stared at her with his darkness adjusted eyes. She was absolutely gorgeous and even though he had seen her naked all day, he’d had the decency to not stare. But with her sleeping, he let his eyes feast before falling asleep himself.

By the end of the second day, he was now confident that his cock wouldn’t spring up unexpectedly. The fact that he had masturbated five times in 36 hours had also helped! After they all ate together on the large deck surrounding the pool, they went back to their room. And so Dustin ended up with Emily in their room. If they had been tired because of the long road trip yesterday, tonight they decided to stay up and chat a while before going to bed.

One hour later, sitting next to one another on Emily’s bed, their back against the wall, the siblings shared a long look. Neither of them would have imagined that they would share so many intimate secrets with each other. During that hour, the room lit only by a single candle, they had talked about nudity, their plans and dreams for their lives and the fact that they had both been single for a long while now.

And that long conversation confirmed something that had been becoming more and more evident. While Emily and Lily were almost perfectly identical physically, they were starting to grow more and more different psychologically. It was strange how one difference could have so much impact. For various reasons Emily was becoming calmer and more reserved while Lily was extroverted and wilder. Dustin was fascinated by that growing difference given the same genes.

But it was getting late and deeper, simpler parts of his brains were beginning to take over. Dustin couldn’t help from looking at his little sister’s body. The more he looked, the sexier he found her. Yes she was very thin, but the way she moved her hips, and that tiny waist, and those out-of-proportion breasts… canlı poker oyna Damn! Maybe it was because she seemed to always be very subtly dancing. Then again, with her long and thick mane of very dark hair, there was something panther-like about her movements. It was as if she was on the prowl.

As Dustin realized that she was more beautiful while she was moving, Emily asked him a question about his erection. As Dustin laughed in surprise, he also realized that such a question was probably due to the three or four beers they had drank during their late night conversation. As Dustin, trying to satisfy Emily’s curiosity, his cock has gotten harder, much to Emily’s surprise and delight. She was laughing about it as he tried to cover it. Eventually Dustin stood up from the bed and turned away. Grabbing a pillow, Emily playfully threw it at him and said “Don’t hide, I’m curious!”

Weathering the pillow assault, Dustin replied “What do you mean, you’re curious? You’ve had boyfriends? You’ve had sex?”

“Just once!” Emily replied, throwing another pillow.

“Stop it! I don’t believe you!” Dustin replied, throwing one of the pillows back. “Just once?”

“Yes! There are a lot of rumors about twins, but don’t believe every one! And now shut up!” she cried, but she was laughing. And threw him another pillow.

“Really? Just once? Damn!”

Emily went to the bathroom and came back with a glass of water. They were looking at each other across the two beds and Dustin was still stunned. Dustin said “I can’t believe this! You’re almost a virgin!”

“Shut up!” she replied, throwing a pillow again.

Dustin hesitated before returning the pillow because of the glass of water. “Put that glass down!” he growled playfully.

“Never!” she cried, laughing as she threw another pillow.

“Cheater!” he said, grabbing the pillow in mid-flight.

By now Emily was laughing very hard and she knelt on her bed to grab the last pillow. When she threw it, she lost her balance and spilled the entire glass of water on her bed. “Fuck!” she cried, trying to remove as much as she could with her hands.

Dustin laughed and said “Haha! Serves you right!”

“Stop it Dustin!” she replied. “Shit!”

Dustin came to help with a couple of towels, but soon enough the siblings realized that it was hopeless. “Damn it!” she said. Looking at his bed, she opened her mouth but paused. She sighed before saying “There isn’t even a couch.” After a moment she looked at him and said “Do you mind if we sleep in the same bed?” And then she added “Oh fuck! I don’t even have panties to put on!”

Dustin didn’t know what to say except “I don’t mind sis…”

“I’m sure you don’t!” she said, half a smile on her lips. “Sleeping with a naked girl in your bed!”

“Well, that’s precisely the problem!” he replied in a flat voice.

Surprised by the tone of his voice, Emily frowned and looked up. “Oh…” she said, realizing his predicament. “Is it true what they say about nighttime, er… nighttime…”

“Erections?” Dustin finished. “Yeah.”

“Oh… Well. I can sleep on the floor.”

Feeling bad for her, Dustin said “No, I’ll sleep on the floor Emily. You can have my bed.”

“No, no… I was my mistake,” she sighed again. “Fuck.” Looking up at him, she said “Think you can behave? And not mention this to anyone?”

“Of course!” he replied, not even feeling half as confident as he sounded.

The siblings talked a bit more after they turned the light off. But now the nudity they had carelessly enjoyed all day was awkward. Being naked around your sister or brother in a nudist colony outside in the sun was one thing. Sharing a single bed in the darkness was quite another.

And so, unsurprisingly, Dustin woke up a couple of hours later. He was on his side and spooning his naked sister. And just as unsurprisingly, his erection was poking her ass. Although he was spooning her, his hand rested on his thigh instead of wrapping around her upper body. He could remove that hand easily enough without waking her up. His cock, though, was another matter. It was lodged pretty good against her ass, between her cheeks. There was no way he would be able to pull out of there without her waking up.

Taking a few long breaths Dustin tried to calm himself, hoping to make his erection fade away. How hard could it be, given that he had done it all day long yesterday? Well, it turned out to be pretty hard indeed. Instead of going away, his erection grew until it was painful in the cramped space. The cramped and very hot space. Shit! Until that point Dustin hadn’t moved a muscle and he still didn’t know what to do.

Very slowly, he tried rotating his hips to see what it would do. Well. The first thing it did was to lessen the awkward pressure, so that was good. His cock was truly becoming painfully bent. The second thing it did was make the taut head slide against the delicate skin of his sister’s cleft. Dustin’s mouth opened wide internet casino in delight as he took a deep breath, but he quickly bit his lower lip to stifle his moan. “This is mindbogglingly good!” he thought! “I’ve been single for way too long, and this is the worst timing ever! Fuck!”

He tried moving again and soon realized that he would have to slide downward. Simply rotating wouldn’t work. And so, slowly, an inch at a time, Dustin used his other hand to push himself lower. Every time he slipped down, he was pummelled by another surge of pleasure. “Am I thinking this through correctly?” he wondered. “Or is my second brain, the one currently nestled between Emily’s ass, only making me believe that making my cock slip ever more towards her pussy is a good idea?”

Breathing hard and covered in sweat, Dustin shook his head and kept going. The lower he slipped, the deeper his cock pushed itself against her cleft. Concentrating on moving slowly and not waking her up, Dustin was suddenly surprised to feel the tip of his cock pressed against his sister’s pussy. “I was tricked!” he thought, cursing his second brain!

But despite his curse, the pleasure he felt was indescribable. He could feel the delicate and smooth shaven skin of her pussy pressed against his cock. Before he could think about what he was doing, his hand gripped her hip more strongly and he pushed against her. “Fuck!” he cried as a flood of pleasure washed over him. His cock was now nestled in the Bermuda triangle! The Bermuda triangle was that sacred space between the pussy and the closed thighs of a thin girl. It was something he had come up with his previous girlfriend when—

Dustin gasped as Emily moved. He froze, but his mind was spinning with pleasure as Emily moved, making her thighs rub against his cock. When she finally stopped moving, Dustin silently let out a long breath and tried to relax. “Hmmm…” a sleepy moan from Emily. Fuck! And then a “Ahhh…”, another moan but one of an entirely different nature. A sexual moan. Fuck! And then, to Dustin’s horror and delight Emily began to squeeze her thighs together. “Oh… Lily…” she moaned very faintly.

Closing his eyes hard, Dustin took a deep breath. “Fuck… She’s having a fucking sexual dream about her sister. Now. Right fucking now! Christ!” Dustin didn’t know if he should just pull out in one go. That would certainly wake her up, but he didn’t know how long he could hold on to his sanity if he remained here. He couldn’t simply fuck his little sister! Crap!

And suddenly dustin opened his eyes wide and opened his mouth just as wide. Emily was getting wet. And so what had already been a irresistibly delicious position turned into a means of enslaving him. If the skin of his cock had been firmly locked against hers before, things were now getting much more slippery. Every few seconds, as Emily rotated her hips, the tip of Dustin’s cock rubbed against her dripping lips.

Was she awake? Was she feigning sleep yet totally into this idea of sex with her brother? Dustin’s mind reeled with such a possibility and he grabbed her hip more strongly. But then he stopped himself. “Are you crazy Dustin?” he thought. “You’re the only pervert here. Not only did you ogle your sister’s naked body all day long, but you’ve now placed your cock against her pussy! While she was sleeping! There’s no way she’s interested in having sex with you! She’s your sister!”

And then Emily moved again, sending another shockwave of pleasure up his cock. And that was too much. Dustin was a 20 year old male, hot blooded and single for too long. Sister or not, a warm, wet pussy was beyond his ability to resist. He knew he had to pull away right now. Even if she woke up. And so he began. Slowly. During that time, Emily was still moaning faintly, whispering her sister’s name. “Well, that explains a lot…” he thought.

As his cock slipped against his sister’s pussy, Dustin was afraid that he might lose it. When he felt the tip pushing against her hole, he thought “Just one push, just a slightly different angle…” Once again he shook his head and managed to find the will-power to pull completely out. It could have worked. It really could. If only he hadn’t paused to savor a few more seconds of his sister’s delicious lips. But he did, and so things were in place when they heard a rather loud clicking sound.

Dustin, awake, knew that it was someone unlocking the door to their room. The thought of someone catching them in such a position made him jerk very quickly. Jerk towards Emily. And Emily, who had actually been sleeping, was frightened awake by the noise and that fright made her jerk very quickly as well. Jerk towards Dustin. And so that meant that despite Dustin’s best attempts, his cock ended up buried to the hilt in his sister’s devilishly sweet pussy.

Emily gasped at the intrusion, but froze in place. In the charged silence, they both heard Lily’s voice “Oh, I’m sorry. I didn’t want to wake you up.” To their horror, Emily and Dustin realized that she was walking in. They were going to be discovered. But Lily’s blue eyes clearly weren’t used to the darkness and she fumbled to the bed to lay a small kiss on her sister’s brow. “Good night.” she then said.

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