The Dawn Chronicles Ch. 01

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Dawn, the super busty cougar, chaperones a school trip.
5.2k words
4.55
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Part 1 of the 4 part series

Updated 06/09/2023
Created 06/24/2019
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*All characters in this story are 18 years old or older*

***

The bus sped down the wide-open, two lane highway, trees and brush whipping by outside. Forty year old Dawn Phillips sat in one of the rows toward the front, two seats to herself since what kid would want to sit with one of the trip chaperones. Dawn's son Tim attended Sunfield Academy and it was tradition for the incoming senior class to go on a trip to the Penfield Activity Camp at the end of the summer before the start of their senior year of school. Dawn had been asked to be a chaperone and she had accepted, always willing to help out as one of the student moms. Tim was in one of the other buses; the class had been split up into two different groups and Dawn had opted to chaperone the one without her son in it so that she didn't embarrass him.

The camp was in another state and was a long 10 hour drive away. They were growing closer to their destination, but they had already been on the road for several hours and Dawn could tell by the noisiness of the rear of the bus that the students were getting restless. She sighed and set down her e-reader, the book she had been reading could only entertain her for so long. As she did so, she felt someone staring at her out of the corner of her eye. She glanced across the row and saw one of the students quickly look down at his lap, blushing slightly. Dawn smiled knowingly.

The student, Billy, was also sitting by himself; he was a bit nerdy, with glasses and short unkempt hair and didn't have many friends due to how shy he was. Dawn had always loved the attention of the younger men at Sunfield Academy and, being bored now with the bus ride, decided to have a bit of fun. She leaned back in her seat, arching her back slightly to thrust her massive double H breasts out. She could see Billy looking at her again, his mouth slightly ajar as he watched her tug down her tight v-neck top a bit. Billy could now see her deep cleavage and a ton of tit flesh bulging out of the low-cut top.

Dawn glanced over again and Billy once more quickly looked away. But then she whispered softly so only he could hear, "Billy."

The student looked shyly back at her and Dawn smiled welcomingly. Then she bit her lip as she saw the growing bulge in Billy's shorts. She slipped a hand down to the front of her own crotch, rubbing her pussy through her jeans.

"Oooo mmm..." the cougar moaned very quietly. Billy was stunned and didn't look away.

It went on like this for about another 15 minutes. Dawn rubbing herself, glancing over at Billy and winking at him and licking her lips slowly, raising her hands up to squeeze her tits and rub her nipples through her shirt. The poor kid looked like he was about to cream in his pants and he hadn't even touched his penis at all. Dawn beckoned him over to her seat and Billy obeyed as if in a trance.

She leaned her face up against his, planting a soft kiss on his cheek, and whispered hotly in his ear. "I think you might want to go take care of that in the bathroom, sweetie."

She ran a finger ever so lightly on Billy's crotch, tracing the outline of his erection. The student shuddered in pleasure and turned away, sprinting up the aisle into the bathroom at the back of the bus. Dawn smiled to herself again, returning her hand to her pussy. She quietly came, clenching her teeth to keep from making any noise. Following her orgasm, she drifted into a nice nap until they arrived at the Camp.

***

The first full day at the camp dawned bright and sunny and the light streaming through her window awoke Dawn as she stretched leisurely in her sleeping bag. She was assigned to one of the boys' cabins and there was a private room with a lockable door for the adult in each cabin. Tradition was that each group would compete in a large capture the flag game the first morning of the camp trip (her son Tim's group was staying across the camp and would hold their own game). Chaperones usually participated, so Dawn changed into tight spandex workout shorts and top. The top wasn't too revealing, but it did cling to every one of her curves, including accentuating her massive mom-boobs.

Dawn went out into the main room of the cabin and roused all the boys from their bunks. She wasn't blind to their ogling her voluptuous body in her tight fitting workout clothes and she wondered how many of them would have to go jerk off to relieve their morning wood before the game. The group of 50 students Dawn was chaperoning walked out onto the field and two captains were randomly selected. One of them was her son's friend Paul, a handsome black-haired boy who had recently undergone a growth spurt and was 6 feet tall. The male students behind her quietly jostled among themselves to try and get a better view of Dawn's thick ass in her tight shorts.

The captain's flipped a coin to decide who would get first pick and the other boy won. Paul scowled as the other student eagerly chose Dawn as the first pick. Once the teams were finalized, the game commenced on the huge field. 25 v 25 with the male and female students running all over the place. Dawn saw Paul breaking into her team's territory unopposed and dashing for the flag. She chased after, grabbing him around the waist before he could reach the flag, giggling as she secured him tightly. Paul struggled for a brief moment before he realized that he could feel Dawn's massive tits pressing into his back. This stopped him in his tracks and his eighteen year old cock twitched in his running shorts. Dawn grinned, seeing the twitch in Paul's crotch from over his shoulder and grinding her own crotch into his tight, muscular ass.

She ran one hand up the front of his thigh and felt his larger than average cock and full, heavy balls. She gave an appreciative moan before realizing that someone might notice them and releasing Paul. Paul blinked out of his lusty stupor and headed back to his own side of the field (having been tagged he had to return to his team's restart point), glancing back at her multiple times as he did so. Dawn simply smiled flirtatiously at him.

Several minutes later, it was Dawn's opportunity to run for the opposing team's flag. Paul, unsurprisingly, must have been watching her because he arrived out of nowhere. He tried to grab her around the midriff, but she eluded him. He chased after her, eventually catching her from behind. Dawn let him grab her this time and quickly grabbed Paul's hands and slid them up onto her tits. She leaned her head back and their cheeks touched.

"You should have went for these the first time you tried to catch me. Much easier to grab." She said in a husky voice as she made the teen squeeze the huge globes.

"Oh jeez Mrs. Phillips." Paul moaned as the milf gyrated her ass against the rod in his shorts.

After a few more seconds of this, Dawn broke away; again cognizant of the fact that she could get caught if she stayed in that position for too long. The game continued and Dawn laughed as she saw Paul eagerly monitoring her whereabouts, hoping to get more opportunities to grope and be groped by the older woman. The winning team was the one that was the first to five flag captures and eventually it was tied 4-4. Out of nowhere, Paul's team made a coordinated all-out rush into Dawn's team's side of the field, hoping to overwhelm the defenders. Unsurprisingly, Paul ensured he was near his friend's mom when this occurred.

Dawn quickly caught him and, whether by accident or on purpose, Paul tripped, the pair falling to the ground. They wrestled for a brief second, unnoticed by the rest of the students in the chaos of Paul's team's rush for the flag. Dawn ended up on her back and tightly wrapped her curvy legs around Paul's athletic waist. His cock was instantly rock hard again and they ground against each other.

"Ohhhh Paul baby." The married woman cooed, sliding the tip of her tongue along her son's friend's earlobe.

Their hands were all over each other. Dawn's squeezing Paul's ass and Paul's running over her thighs and aggressively pawing at her giant tits. After about thirty seconds where Paul thought he might explode in his shorts, loud cheers snapped them back into reality and they quickly pulled apart to see Paul's team celebrating winning the match. Paul reluctantly left Dawn's company to pretend to partake in the celebrations and Dawn could see the teen casting longing glances her way for the rest of the morning.

***

After lunch, Dawn's group went to the pool area. Being an absolutely massive and expensive venue, Penfield Activity Camp's pool was huge, complete with a giant sixty foot tall water slide that fed into a winding lazy river, the latter of which eventually emptied out back in the pool. Dawn changed into her swimsuit in the locker room. Normally, she would wear a bikini at a pool, but given that she was a chaperone she had erred on the side of being more respectable and wearing a red one-piece. Nonetheless, for a woman as tremendously busty as her even a one-piece was sexual. Her massive mammaries bulged the top of the one piece out in front of her and there was nothing she could do about the tons of cleavage showing in the snug neckline.

The students were all splashing and playing in the pool when Dawn arrived. As she walked up to the waters edge every single Boyd turned to face her with a look of awe on their faces. She smiled and waved at everyone as the horny teen males let their eyes roam over her voluptuous body. Dawn splashed into the pool, every movement causing her breasts to jiggle invitingly within the confines of her suit, laughing and playing energetically with the students. Soon enough one teenager in particular approached her. She knew him by name but had never met him before.

Her son Tim had always described Reggie as sort of an asshole and Dawn could tell that the teen had an Alpha male vibe surrounding him. Reggie grinned wolfishly at her as he approached her and her eyes token his chiseled abs and jacked, muscular body. Dawn new that he was a skilled member of the Sunfield Academy football team. The cougars pussy tingled as she watched him walk toward her through the shallow water.

"Hi Mrs. Phillips, I'm Reggie I don't think we've met." The boy, who looked more like a man, extended his hand politely but made no effort to hide his eyes devouring her curvy body.

"Nice to meet you, Reggie. I think my son Tim has mentioned you before." Dawn shook his hand and smiled.

"Yeah I know Tim." Reggie said, nodding as he released Dawn's hand, trailing his fingers slowly along hers as he did so. "He's a cool guy. I bet he gets that from you." (Reggie, being part of the "cool" crowd at Sunfield, had never really spoken to Tim at all, but Reggie felt Tim's mom didn't need to know that)

Dawn chuckled at the small compliment, her eyes inadvertently wandering down to the impressive length of cock outlined by the wet clinging material of Reggie's swim trunks.

"So, have you been down the water slide yet?" He asked her. Dawn shook her head and Reggie continued. "Oh come on you have to try it! Here, we can go together."

Dawn laughed again as Reggie took her by the hand, leading the sexy milf out of the water and through the pool area to the steps up to the top of the long slide. As they reached the stairs, Reggie stepped to one side.

"Ladies first." he smiled and gestured to Dawn to proceed him up the stairs.

Dawn laughed mentally, knowing that Reggie really just wanted a view of her ass, but she complied willingly. The teenage boy followed her up the stairs, his eyes glued to her big thick ass. The mom made sure to make exaggerated sways side to side with her hips to further entice the young stud behind her. Eventually, they reached the top where Dawn saw that blown up inner tubes were the vehicle in which people would ride down the slide. Other students were grabbing theirs and heading into the enclosed cylinder of the slide itself, but some of the males stopped to eye Reggie jealously as he handed Dawn a tube.

"Here, we can just share one. I'll get in first and then you just sit down in my lap." The toned, tanned teenager said to her.

"Are you sure? I might be too fat for it to be comfortable." Dawn said jokingly.

"No way! You're perfect." Reggie replied.

She blew him a kiss and said softly, "Flattery will get you everywhere."

"I hope so."

Dawn slowly straddled Reggie, making sure to lower her ass slowly so that he got an extended look. She settled her thick ass onto his lap and leaned back against him. His excited breaths hot in her ear made her pussy even wetter as she felt his large teen cock settle between her ass cheeks and quickly begin growing to its full seven and a half inch size. Reggie pushed off with his arms and they shot into the enclosed water slide. Twisting and turning around the rapid curves, Dawn's body bouncing and jiggling atop the teen beneath her. Reggie slid his hands up to the sides of her ribs and stopped, hesitating. Dawn turned her head to look into his face.

"You can hold them. Hold me tight, Reggie." She said.

The teenage jock eagerly complied. Squeezing the busty cougar's huge breasts through the fabric of her one-piece. Feeling the nipples poking hard against the material, he ran his thumbs in circles around them, making Dawn coo and whimper as her body writhed against him as though it had a mind of its own. Reggie was groaning in pleasure as well; the feeling of Dawn's full ass working his erection was incredible. The couple's moans echoed off the plastic walls of the slide and mixed with the sound of rushing water. After what felt like an eternity to both of them, they shot out of the slide into the lazy river. The force of the exit toppled them from the raft.

When Reggie surfaced, he saw that Dawn had already climbed aboard the inner tube and was laying on her back. She flicked her wet, dark brown hair out of her face and gestured to the muscular high school senior.

"Your turn to be on top." She smirked enticingly at him.

While he would have preferred to have Dawn still sitting on him, Reggie didn't argue and climbed on, scooching back into her lap as the current took them. The lazy river was completely surrounded on both sides by bushes and trees and the nearest students were a ways ahead or behind them, so the cub and the hungry cougar had complete privacy as the river wended its way along. Dawn let her hands run over the boy's rock hard abs and muscular biceps, planting small kisses on his neck, ear, and cheek as she did so. Reggie let his hands slide up and down Dawn's womanly thighs.

Dawn continue to let her hand trail down under the waistband of his suit, scratching at Reggie's pubes, before pulling away. She did this several more times, causing the teen to let out an involuntary groan of frustration. Dawn smiled and let her hand go all the way down, caressing Reggie's cock and balls. The water wasn't as good as lube, but it provided enough lubrication that Dawn could slowly stroke the hard on up and down.

"Yesss, so full and thick for me." She hissed into his ear.

Reggie was beside himself. He had approached her with confidence, but even then he didn't really think anything would actually happen. And now here he was lying against his classmate's mom as she jerked him off.

"Ohhhh fuck." Reggie grunted.

Dawn coiled her long legs around his, pulling him tighter into her clutches as she stroked faster. Every time her shuttling hand reached the head of Reggie's cock, she twisted and squeezed softly, sending jolts of pleasure through every muscle in the teen's body. Her other hand rubbed and massaged his cum-filled balls through his swimsuit.

"Ah fuck, Mrs. Phillips...oh fuck you're so hot. You jerking me off is so hot." Reggie moaned.

"Mmmm I'm glad you like it." She nipped at his ear teasingly. "Can't wait to feel you shoot a creamy load for me baby."

Reggie's hips were thrusting up off her lap now, meeting Dawn's strokes. His eyes were clenched shut, teeth gritted tightly in pleasure, moaning incoherently. Dawn felt his young balls tighten in her other hand and scratched at them with her long fingernails, working to put the young stud over the edge. He was so close...he was almost there...he...

"Cannonball!" A blurred form hurtled out of the bushes to their right, landing right next to the tube and sending Reggie and Dawn toppling into the water once more.

The both surface to see Paul standing there. The two teens were glaring daggers at each other and it was immediately clear what had happened. Paul must have seen them together and become jealous, deciding to break up the moment. While Dawn was somewhat disappointed that she hadn't been able to coax a big load from Reggie's balls, she was also half amused and pleased that Paul wanted her so badly that he'd be jealous. Reggie and Paul began arguing with each other and Dawn stepped in to separate both of them, sending them each on their way through the rest of the river and back into the crowded main pool. Once they got there, the milf extricated herself from the pair and didn't attempt to flirt with either of them the rest of the afternoon due to the presence of the rest of the students.

***

The next day brought another traditional event: the camp scavenger hunt. On its face, a scavenger hunt sounded lame, but this one had a quite lucrative prize of a few hundred dollars. All you had to do was find a small camp flag hidden in a box somewhere on the property. There was only one, so there would be only one winning team. The students were split into pairs randomly. The chaperones participated in the random drawing as well, but of course if a team with a chaperone and student on it won, the chaperone would give the full prize money to the student rather than splitting it 50/50.

Dawn wore daisy dukes and a tank top that, like her one-piece, wasn't designed to be revealing but there was simply no hiding her massive HH cups. Dawn was paired up with Christopher. A stocky boy who, like Billy whom she had teased on the bus, was also nerdy. He wore cargo shorts and a World of Warcraft shirt and seemed so enamored by Dawn that he could barely string words together when he introduced himself. This made Dawn want him immediately. She loved young men because of exactly how awestruck they could be by her, how their gazes of lust made her feel like the sexiest woman in the world, and because she knew that she'd probably be giving them the best sexual experience that wouldn't be topped for the rest of their life. All of the other boys were of course furious that they hadn't been lucky enough to be paired with Mrs. Phillips.

The whistle blew and the various twosomes scattered across the camp. Christopher made to head towards a cluster of camp administration buildings but Dawn grabbed his arm and tugged him the opposite way.

"Christopher, I think we should look in there."

Christopher frowned. "The woods? Um...what uh...why would they put it in there?"

"Because they don't think anyone would go trekking through the woods to find the box. See look, no one is even going that way." Dawn reasoned with him, still leading him into the treeline. However, she wasn't interested in winning the scavenger hunt, the cougar just wanted to get her prey to somewhere private.

They walked for a bit through the woods, Christopher puffing and out of breath as he clambered along. Dawn made small talk with the shy teen as they did so.

"So, any girlfriends?" She asked him.

"I...w-wha? N-no." Christopher said nervously, tripping over his words.

"No? A handsome young man like you? Really?" Dawn flirted. Christopher's face flushed crimson in response.

After several more minutes they spotted some structures sitting in a bit of a clearing. There were some dilapidated cabins, a tiny drained pool in the ground, and a playground.

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