Chaperones break a cardinal rule [MF] [Long]

As Mark quietly trudged through the sand to Katelyn’s bungalow in the dark, he couldn’t help but think about the lecture he had given his students two weeks ago in his classroom. He had stressed to them the importance of not breaking any of the cardinal rules while on their service trip to the Pacific Coast of Costa Rica: no drugs, no alcohol, no fighting, and absolutely 100% no sex. Doing so would result in immediate removal from the trip and a expedited flight back to Maryland.

With each step he could hear himself saying to students and their parents that such behavior would not be tolerated. You are representing the school and the larger school community, he stated resolutely. He was sure this stern speech would be enough to deter any misbehavior on the part of his students. It never crossed his mind that he might be the one breaking the most serious of his rules.

But there he was, dodging crabs and rocks as he walked from the front of the hotel property where he was staying to the back, where his district mandated female chaperone was staying. Katelyn had volunteered to go on the trip quite eagerly. She was 35 and had never traveled out of the country and felt the need for some adventure after a messy breakup with her long term boyfriend.

Up until their second day working in the mangroves in the heat, Mark had never really thought of Katelyn as anything other than a colleague. Of course he recognized her attractiveness. She was quite petite, just 5’3” and maybe 110lbs, with strawberry blonde hair. Her chest wasn’t anything remarkable, nor was her bottom. But she kept fit and could fill out any number of the dresses she wore to school.

At one point in time Katelyn had actually been a mentor of sorts to Mark. His first year teaching was her third, and his district assigned mentor had been flaky all year. Like Mark, Katelyn was a career changer, which led to a more natural partnership given their similarities. She provided invaluable advice during his first years in the classroom.

So the fact that he was now sneaking across the palm tree covered hotel property under the cover of night while the waves of the Pacific Ocean crashed onto the beach a dozen yards away was all the more exhilarating. At 35, Katelyn was 7 years Mark’s senior. The age difference only added to the exhilaration. Up until this point Mark had only ever been with women his own age or very close to it. What would it be like, he wondered as he snuck past the last of the student-occupied bungalows to where the female chaperones were staying.

When he got to room 43, he knocked 4 times, pausing between the first 2, just like they had talked about before starting their nightly room checks for their group of 20 students.

Katelyn answered the door in athletic shorts and a sports bra, the very outfit that sparked the initial desire in Mark in the mangroves yesterday. They had been working in the heat for hours alongside their student group, filling planters with fertile swamp mud and stuffing them with young mangrove seedlings. It was impossible not to be covered in a mixture of sweat, mud, and sunscreen.

At some point in the afternoon, everyone began removing their mud caked clothing, revealing bathing suits underneath for most of the students. This was no big deal as they had been hanging at the beach or pool when they weren’t toiling away in the mud. But when Katelyn took off her crop top to reveal a low cut purple sports bra, Mark was a little taken aback. Katelyn took notice of Mark’s attention. It flattered her that someone might ogle at her, as her recent breakup had really taken a toll on her confidence. She made sure to stay within Mark’s view as she continued to work.

Mark was suddenly acutely aware of just how attractive Katelyn was, and it took a lot of mental effort for it not to show in the form of a bulge from his board shorts. He resolved to add the image of a sweaty and muddy Katelyn to the back of his mind for use later in the evening when everyone had gone to bed.

When they had finished their work in the mangrove for the day, they cleaned up by taking a dip in the Pacific. The group of students led the charge across the sand, eager to wash away the grime before heading back to their bungalows to clean up for dinner. As Mark and Katelyn watched their students run unabashed through the sand, they drifted a little closer to one another. Their was a certain spark between them, enhanced by the beauty of their surroundings.

Katelyn broke the rising tension, joking that she hadn’t had this much mud on her body since an ill advised wrestling match with a college roommate. Mark laughed nervously, not fully aware that Katelyn was flirting with him, trying to gauge his interest. She tried again, this time stating that she couldn’t wait to strip out of her clothes and wash the mud and grime from her body. This got Mark’s attention, as evidenced by the “wow” expression his face shifted to.

By now the students were totally enamored with the ocean and Mark and Katelyn had a wide section of the beach to themselves. Katelyn took advantage of their near solitude to let Mark know she saw him ogling her in the swamp earlier. Mark tried to play dumb for maybe a millisecond before coming clean. “Of course I was staring, how could I not? That outfit is amazingly sexy, even if it’s mostly caked in mud.” Katelyn, encouraged by her colleague’s use of sexy to describe her, countered by acknowledging the growing bulge in Mark’s shorts.

The sexual tension was reaching a breaking point when all of a sudden a wall of teenage squealing moved their way from the beach. The student group was refreshed and re-energized by the cool ocean and wanted to scour the area for fresh fruits to eat and iguanas to marvel at. Mark and Katelyn quickly shifted into chaperone mode and joined the students on their adventure.

The tension was completely gone by the time the group settled into dinner at the hotel that night. Everyone was exhausted from the physical day spent in the swamp. They all turned in early that night in order to be fresh for their trip down the coast to a national park for a day of fun and relaxation. But Mark was unsettled as he tried to fall asleep. He kept having flashes of Katelyn working in her sports bra, sweating in the mangrove. He decided the only way to get some sleep was to masturbate. It didn’t take long for him to reach his orgasm, unloading into some tissues in his bungalow bathroom, sweating and breathing heavily from the heat of the night. He climbed back into bed and nodded off to a post-orgasm slumber

The next morning the group boarded their bus. Most everyone was bleary eyed and looking a little lethargic. They were hoping to sleep some more on the two hour ride to their destination. Mark and Katelyn settled into their seats next to one another, something not unusual for the trip as they used the down time to discuss the day’s itinerary. Only this time that was the furthest thing from both of their minds.

Katelyn broke the tension again, saying that she had the hardest time getting to sleep, even though she was physically exhausted. Mark nodded, not sure of his next move. Was she just being friendly and making conversation? Or was she continuing yesterday’s sexually charged flirtation? Should he tell her that he nodded off to sleep after images of her chest led him to orgasm? Surely no, that would be crossing a line, he thought. But before he could muster a response, Katelyn smirked and said good thing I can get off quickly and quietly! Mark’s cheeks flushed with the thought of his colleague getting off, and Katelyn could sense the excitement. She placed her hand on Mark’s leg, near the end of his board shorts, then whispered “did you think about me too?” in his ear.

Mark’s face went totally red. What was happening right now? Is Katelyn really coming on to him on a bus full of teenagers who they are in charge of chaperoning? But before he could process the situation any further, a student tapped on his shoulder and alerted him that another student was feeling sick and needed some motion sickness medication.

Katelyn, noticing Marks inability to get up from his seat, happily jumped across him and got the medication from the first aid kit. She spent the rest of the ride comforting the student, leaving Mark at the front of the bus to ponder what would happen next.

The group enjoyed their time in the national park, but had split into two groups wanting to see and do different things. This left Mark in charge of one group and Katelyn the other. When they met up at the bus mid afternoon, all the tension of the morning was gone, erased by the duties of being a chaperone of teenagers in a foreign country.

But luckily the student had exhausted themselves and slept most of the way back to their hotel. This gave Mark and Katelyn the chance to rekindle some of the excitement from the morning. Only this time there was no hesitation or second guessing by Mark. He had taken the day to think about the last 24 hours and decided he should make a move. He slipped a piece of paper into Katelyn’s hand that simply read “your room, 1 am”. It had to be her bungalow – his was too close to the main lodge where students might try to sneak out to after room checks for some ping pong or cards or whatever teenagers who can’t drink or hook up do.

Katelyn felt her thighs twitch as a wetness formed between her legs. She had been leading him on all morning and most of yesterday. She was surprised by his newfound confidence, as she had been in control thus far. But at least he had finally taken the bait. All that was left was to iron out the details. No one else could know or even be suspicious that the pair were plotting a late night rendezvous. The rest of the ride was mostly silent, both contemplating what was about to happen. The awkward silence was only broken by the familiar cry for motion sickness medication, which Mark was happy to doll out this time.

Dinner was waiting for the group upon their return to the hotel. Mark and Katelyn had agreed to proceed with the evening as usual. Eat dinner with a different group of students, return to their room for a shower, and then relax in their own way. Mark had become accustomed to laying in a hammock and gazing at the night sky through the palm trees, while Katelyn laid close by reading on her iPad. Students came and went, some with questions, some checking in before they headed to their bungalows fo

They stayed this way until 11:30, when they started their rounds to make sure everyone was in their room and settled in for the night. When they were finished, they met back at the main lodge to debrief the check in. All was good with the girls according to Katelyn. All was good with the guys according to Mark. It was almost time. But they needed a signal – students had been known to knock on doors in need of things like toilet paper, ibuprofen, tampons, whatever. They needed to be certain. They agreed on 2 knocks, a pause, and 2 more knocks.

Mark and Katelyn returned to their respective rooms to await their 1 am meeting time. Mark updated the group’s Instagram page with pictures from the day. Katelyn continued reading, although not getting very far. The ticking clock in her bungalow was like torture as she could feel the excitement making her warm and wet.

Around 12:50 am Mark quietly left his bungalow and set off through the sand for Katelyn’s, being careful to avoid the crabs that seemed to conjure on the hotel property at night. About the same time, Katelyn turned her iPad off and quickly changed into her sports bra and shorts from the previous day. In a moment’s notice it was the best she could do, having not packed anything sexier and wanting to be at least somewhat decent in case a student crashed the party with some random request. It had the added bonus of being what initially caught Mark’s attention.

She heard the 4 knocks on her door and jumped from the bed, pausing a moment to compose herself before quietly opening the door. Mark looked so irresistible in that moment, his slender 6 ft frame posing in the doorway, blocking the moonlight from above. She grabbed his hand and pulled him in quickly, closing the door almost too loudly in the process.

From that point on all the awkwardness of the past day and a half faded away. It was pure heat between them. Mark tenderly grabbed Katelyns neck and planted his lips on hers, his tongue probing for hers and she melted into him. They knew this had to happen fast. They couldn’t risk going slow and being caught by some prying teenager.

Katelyn quickly stripped from her outfit and then tugged at Mark’s waistband. He obliged and stepped out of his board shorts to reveal an erection that had been building since earlier this morning. They embraced and kissed again, more passionately this time as both could sense the excitement in the other. Marks hands wandered down Katelyn’s back, gripping her buttocks firmly. He pulled her cheeks apart and felt Katelyn squirm in his hands. His erect cock was pressed into her belly, and he could feel her fumbling to grab hold.

He released his grip on her and let Katelyn stroke him, up and down, up and down. As she stroked she looked him deep in the eye and said “Take me.” With that he scooped her petite frame into his arms and placed her on her back on the bungalow bed, legs spread and sex on full display. Wanting to savor the moment to some at least some degree, Mark paused to take in this beautiful woman who just days ago was a colleague and mentor. But now, she was his.

He lowered himself onto the bed and planted several teasing kisses on her inner thighs. She let out the slightest of moans and squirmed as she felt the wetness between her legs. Mark placed himself at the entrance to Katelyn’s sex and slowly worked his way in. His average length was made up for by his girth, which stretched her more than she expected. Mark slowly withdrew and re-entered several times to allow her to get used to him. They slowly built a rhythm. Her hips rose to meet him as he thrusted forward and she wrapped her legs around his back. Sensing some urgency, Mark picked up the pace and was thrusting in and out of Katelyn, hitting her in just the right spot as her legs gripped his back.

Neither was going to last long. As Mark pounded in and out of her, Katelyn could feel her orgasm building deep within her core. She began letting out little wimpers with each thrust, which drove Mark closer and closer to the edge. As Katelyn neared her orgasm she begged Mark to fill her up. That was all he needed to hear as he pumped in and out of her. As she felt his orgasm explode inside of her, Katelyn’s legs gripped Mark’s back, pulling him deep inside her and sending wave after wave of orgasmic pleasure through her body.

Mark rolled over on the bed. They were both spent, exhausted physically and mentally. He cradled Katelyn’s petite body in his arms, feeling her chest rise and fall as she slowly regained her breath. He couldn’t stay long – he needed to get back before anyone realized he was gone or someone came knocking on either of their doors with a late night request.

Mark rose from the bed and planted a passionate kiss on Katelyn’s lips, to which she giggled a bit, still in awe of what had just happened. He covered her with the blanket, dressed, and quietly opened the door to creep back across the sand to his bungalow

Source: reddit.com/r/gonewildstories/comments/khsidx/chaperones_break_a_cardinal_rule_mf_long