“Kaitlin, a word in before you head out please?”, came the voice of head coach Drew behind her. It was Wednesday evening, and they had just completed a successful practice at the rowing club. Wondering what this might be about, Kaitlin followed Drew into the boathouse office. She felt Drew was eyeing her body as usual while she squeezed herself into one of the chairs.
Kaitlin volunteered part-time as an assistant rowing coach at a high school’s row club. She had herself been an excellent rower at Harvard with a full athletic scholarship but her professional career had been derailed by injuries. Now in a regular 9-5 job, the 26 year old had wanted to stay in touch and give back to the sport she loved so much. With her goofy, charming, and caring personality, she had been hired on the spot by Drew for the role a few months back. She had been aided by her physical appearance too. Kaitlin was a tall (5’11”), slender brunette with gorgeous natural 36 D breasts, and a beautiful round ass to die for. She had a cute face, with electric blue eyes, and a smile that could light up an entire room. She was at least a 9 in most men’s books if not a 10.
“I’m going to need a favour for this weekend”, Drew started.
“Sure, I don’t have any plans yet. What’s up?”
“Oh, thank God. We need you to chaperone Dan, Mark, Shane and Cole this Saturday for their quad race. It’s at the seniors regatta over in Camas. We’ll provide you with a rental van and a driver so you don’t have to drive 4 hours each way. We’ll also reimburse all expenses for the day of course. Just coach the boys and make sure they’re on their A-game. If they win their race, they may get some attention from college scouts. Can you do that?”
Kaitlin was a little unsure of single handedly chaperoning four 18 year old boys but since it was a single day trip, she told herself “What’s the worst that could happen?”. Since it was in her nature to always help those around her, she agreed to do it. Her personality had made her a popular figure with all the students. But she was especially popular among the senior boys who were always horny, and found her extremely attractive. Kaitlin used to get hit on by the boys very regularly but would just laugh it off as teenagers being teenagers and decline all advances.
“Sure, just email me the schedule and anything else I need to know, and I’ll take care of the rest”, she told Drew.
“Oh, thank you so much. You’re such a saviour”. Drew stood up with Kaitlin and gave her a big hug to press her breasts into his chest before letting her leave for the evening.
The rest of the week passed normally, and a yawning Kaitlin was standing outside her apartment complex at 3 am Saturday ready to be picked up. It was the middle of summer, so she was wearing a loose white tank top and grey fleece shorts for the day. Since it was just a day trip, Kaitlin didn’t carry anything more than a mini pack containing some snacks and water.
Shortly after, a white van pulled up next to her. Before she could open the front door to ride shotgun, the sliding back door was opened by Mark, Shane, and Cole who passionately insisted that Kaitlin get in the rear compartment with them. Since they were one team for the day, they needed to ride together. Kaitlin was happy to oblige, and took a seat. The van compartment was roomy and had 2 rows of seats facing each other. Kaitlin was seated next to Shane facing the back, and Cole and Mark sat across facing towards them. The van stopped next to pick up Dan, and he too got inside the compartment, taking a seat across from Kaitlin.
After about ten minutes of small talk, the group began to drift away in sleep. Dan however, had a plan and stayed awake. Dan was the rowdy leader of the pack, and harbored many fantasies involving him and coach Kaitlin. He’d had a few girlfriends so far, but none of the high school girls could hold a candle to coach K. There was so much he wanted to do to Kaitlin’s voluptuous body. He had discussed some of his fantasies with his buds and he knew that the other three also felt similarly. Shane and Mark had steady girlfriends, and Cole was still a virgin. But they unanimously agreed that Coach K would be one hot fuck.Together, they had discussed some wild stories in which they would gangbang their sexy coach many different ways.
After Dan was sure that Kaitlin was asleep, he woke up Shane, Cole, and Mark.
“Dan, what is it?”, Mark grumbled in annoyance.
“Idiot, look. There”, Dan pointed towards Kaitlyn.
The other boys looked over to see the most beautiful sight. Kaitlin was slumped backwards in her seat completely asleep. Her head tilted to the left, and her mouth half open gave her the appearance of a peaceful angel. Her slender, toned arms. Her long, shapely legs with no coverage beyond her upper thighs. The deep neckline of her tank top showed all of her neck and about an inch of her cleavage. Her pink sports bra could easily be made out underneath her thin top.
“God, she is so hot”, Mark said.
“I want to fuck her so badly”, replied Shane.
“I want to stuff my cock up that tight asshole of hers”, said Dan.
“I’d just settle for a blowjob from her. I bet she gives the best blowjobs”, Cole longed wishingly.
Before anyone could react, Dan reached forward and gently poked Kaitlin in her thigh. No reaction. “You know what this means boys, right?”, as a sly smile came over his face.
The boys continued to cautiously expand their comfort zone with their sleeping coach. They all took their phones out and first took as many photos they could from all the different angles. Initially, they limited themselves to gently touching her legs or arms.
After a while, Shane gently raised her top so the boys could take some upshirt photos. Their coach’s exposed toned stomach only led to the boys feeling hornier. How they wished she wasn’t wearing a bra.
Shane then placed his palm on Kaitlin’s left breast and after a few seconds gave it a squeeze. A light moan escaped Kaitlin’s mouth. The boys got scared and pretended to fall asleep. After realizing that their coach hadn’t moved at all, they slowly returned to Kaitlin’s breasts. They loved the soft pillow-like texture of her breasts, and how it seemed to harden under their touch. None of the girls they had been with had breasts that were as well developed as Kaitlin’s. They kept enjoying the soft moans that were escaping Kaitlin. At one point, Dan who was feeling particularly brave, gave both of Kaitlin’s breasts a tight, hard squeeze. This caused Kaitlin to emit a louder groan and her body to twitch for a second. Scared shitless, the boys pretended to fall asleep for a few seconds but there was no more movement from Kaitlyn.
“Dan you idiot. What did you do that for?”, Shane muttered.
“I don’t know. I couldn’t help myself. Her breasts just feel so good. Plus look at her now”.
Even though she was asleep, on some deep level Kaitlin was probably getting aroused from the boys’ attention. The breast play had hardened Kaitlin’s nipples and they were proudly poking through her clothing.
“Look at that. Coach K is turned on”, Dan observed.
“Her nips are so sexy. Fuck she looks even sexier now”, Shane remarked.
They took more photos of her in this state. After a while, Mark had an idea.
“Cole, last I checked, you have never kissed a girl. Why don’t we change that?”.
After some encouragement, Cole gave her coach a gentle peck on her cheek. Next, he aligned his face with hers, and gave her a gentle peck on her lower lips, which led to silent high fives between the boys, who were recording all of this. Cole continued to give soft pecks, and after maybe the tenth kiss, Kaitlin’s lips closed involuntarily around Cole’s as she kissed him back. Cole and every other boys’ eyes widened in shock, but Cole kept his composure to keep gently kissing Kaitlin for a few seconds before pulling away. Still asleep, Kaitlin groaned as Cole pulled away and her right hand moved such that her fingers were by her inner upper thighs.
“Holy shit, she is actually trying to masturbate. Cole, you must have turned her on. Not bad for a first kiss”, Mark said.
More photos in her vulnerable state. The boys wished they could have a peak at their coach’s pussy, but there wasn’t any such luck yet. Her fingers still lay static a few inches away from her pussy.
Wanting more action, Shane tried to push Kaitlin’s palm further up her legs. Unfortunately, the sensations were a little heavy, and Kaitlin’s body shook for a few seconds and it was clear she was going to wake up.
“Shane, you ass”, hissed Dan as all 4 boys quickly went back into sleeping positions. Sure enough, a few seconds later, Kaitlin opened her eyes and surveyed her surroundings. The 4 boys appeared to be asleep. Kaitlin smiled to herself. She was completely unaware of the action that had been going on in the car. But during all of it, she had been experiencing an erotic dream.
Kaitlin had been dreaming of a recent one night stand with her Tinder date whose big black cock had kept Kaitlin up most of the night. She had woken up in the van quite aroused amd feeling a little wet. She wondered if being in a close proximity with four teenage adult boys had something to do with her dreams.
The boys eventually pretended to wake up from their sleep and the rest of the drive went by normally. Mostly discussions around their race strategies. The boys did manage to convince Kaitlin to let them drink beers on the drive back. “Only if you win your race”, Kaitlin had stipulated.
At the lake, Kaitlin settled herself near the finish line while the boys rode their boat to the starting line. At the start line, Dan huddled with the guys and hatched a plan which revolved around winning the race and more if they were lucky. By the end of his pep talk, the boys were pumped and they crushed their race, winning it by several boat lengths.
Kaitlin was cheering loudly and jumping in excitement as her boys won the race. When they got out of the water, she embraced each of them in a warm hug that the boys enjoyed.
The boys dispersed to stow the boat and buy beers, while Kaitlin stayed behind to watch the remaining races. After the last race was done, one of the event organizers approached her,
“Oh there you are Coach K. We’re ready for you.”
“Ready for what?”, a bemused Kaitlin asked.
“For our annual coach’s charity swim race. Per our rules, a coach has to be nominated by their respective high school. I have your name here for Westlake High. Look.”, the man pointed on the sheet.
Sure enough, there was Westlake High and Kaitlin Robertson on the list, along with a $100 donation in her name.
“Umm… Drew didn’t say anything about a swim to me. I don’t know how you have my name on there…”, Kaitlin started anxiously.
“Well Ma’am, someone from your school did sign you up. Now we can cancel your entry and refund the money if you want. But it’s going to delay the race, and frankly the charity could use all the help it can get”.
“Okay….”
“Great! The swim starts in 10 minutes over by the desk there. Please be there in your swimsuit in 5 minutes.”
Kaitlin was now seriously panicking. She didn’t have a swimsuit. Or a spare outfit to change into afterwards. Kaitlin took off her top. And then her shorts to reveal a pink cotton brief (“Thank God I didn’t wear my thong today”) and sprinted to the start line in her lingerie. A few boys whistled at the sight of this hot woman.
All things considered, her swim went quite well. She finished 6th among the 8 coaches, but had beaten the other 2 female coaches in the swim. Her arm and core muscles were aching by the time she was out of the lake, and her body was shivering. Thanks to the cold water, her bra and panties had turned semi-sheer and were sticking against Kaitlin’s body. Her nipples and a cameltoe were quite prominently visible.
Shane, Dan, Mark, and Cole were waiting on the shore shouting encouraging words like “you did great coach K”, “you kicked ass out there”. They each gave her a long hug. A little too long Kaitlin thought. They made sure to press their bodies against hers so they could feel her breasts.
Kaitlin grabbed her clothes and found a semi secluded spot behind a tree. She changed out of her wet underwear and put on her tank top and shorts with no underwear underneath anymore.
As they loaded into the van compartment, Kaitlin felt a little exposed. Her perky nipples were still hard and clearly poking through. And the white semi sheer tank top did reveal her bust without a bra. “I hope the boys don’t notice, I just need to ride this out for 4 hours”, Kaitlin thought.
The boys had managed to score 3 cases of beer with their fake IDs for the drive back. And they passed a beer round to each including Kaitlin. The boys suggested playing Truth or Drink. Kaitlin declined but the boys loudly protested and pressured her until she agreed to play.
The boys added a twist to the game where if you declined to answer 3 questions in a row, you had to additionally chug an entire beer can. The game started harmlessly enough. But after a few rounds, the questions started getting more personal, and targeted towards Kaitlin. Like “have you ever kissed a girl”, or “have you ever taken a dick in your ass”.
Kaitlin soon struck out three in a row and chugged her first can. She lashed out with “are you a virgin?”, and Cole was singled out. But it was Kaitlin on the hot seat again, as the boys would get to ask 4 questions in a row before it was her turn again. Kaitlin was soon down 3 cans of beer and was feeling quite tipsy and loose. She failed to realize that the boys asked her the same 3 questions they had 2 rounds ago. In her drunk state, she answered them this time. She admitted to having done anal many times. She revealed her bust size as 36D, and admitted to finding the 18 year old boys she coached attractive. “But nothing will ever happen”, she added. By now the boys had stopped calling her “Coach” or “Coach K” and were simply calling her “Kaitlin”. The boys were also getting increasingly touchy-feely with their coach. They were all pretty much grazing their hands against her arms and legs and had even accidentally brushed their hands against her breasts. All the physical touch was increasingly turning Kaitlin on, and her inhibitions were quite lowered from the alcohol.
When Kaitlin was on her 5th beer, Dan tested the waters by placing his palm on Kaitlin’s right breast. To the boys’ surprise, Kaitlin simply looked up at Dan with lust in her eyes and didn’t ask him to remove his hand. At that point Dan lowered his lips onto Kaitlin’s and started making out with her passionately. As Kaitlin kissed Dan back, the rest of the boys pulled her shorts down to reveal Kaitlin’s completely shaven pink pussy. Kaitlin was too turned on to protest. The boys lowered her into the floor on her back. Cole and Shane started fingering her pussy and rubbing her clit. Mark put his hands underneath her top and was roughly squeezing Kaitlin’s breast. He raised her loose tank top to her neck at once revealing Kaitlin’s perfect white mounds with large pink areola and protruding darker pink nipples.
All the attention had Kaitlin dripping wet like a tap. The boys all took their shorts off to reveal four hard cocks. Dan lowered his cock to Kaitlin’s mouth and she reached out a hand towards Mark’s cock. At the other end, Shane lined up his dick against Kaitlin’s hole and pushed in, drawing a gasp from Kaitlin.
“Ohhhh coach K, your pussy is so tight”, groaned Shane as he deeply thrusted in and out.
“She looks so wet”, Cole observed who was rubbing his fingers on Kaitlin’s clit.
“Hmmpphhh”, was all Kaitlin could muster as Dan’s cock was vigorously face fucking her. The simulation on her G-spot and clit from the two boys had her on the edge very quickly. Shane only lasted about 20 seconds before he climaxed and started pumping volumes of his cum inside Kaitlin’s pussy. His cock pumped 8 times before all his cum was released. The sensation of Shane’s cum in her pussy pushed Katlin over the edge as she experienced a body shaking orgasm. Her lips involuntarily tightened around Dan’s dick and her fingers around Mark’s causing them both to also climax.
Dan kept shooting spurts of his cum down Kaitlin’s throat for what seemed forever. “God, these teenage cocks”, thought Kaitlin as she did her best to swallow all of Dan’s cum. Mark meanwhile exploded all over her face. Kaitlin closed her eyes as she felt Mark’s cum landing everywhere from her forehead down to her chin.
As the boys finished cumming, Kaitlin too started to relax from her own orgasm. Before she could take a few deep breaths, she felt another cock replace Shane’s in her pussy. She thought, “Not so soon please, my pussy is too sensitive”. Before she could say it, she opened her eyes in shock to see Cole hungrily thrusting in and out of her.
“Guess who is no longer a virgin, Kaitlin”, Cole taunted her.
Shane had taken his phone out and was recording Cole losing his virginity to his coach.
“Aaaaaaaahhhhh”, was all Kaitlin could manage.
Dan and Mark had meanwhile descended on her breasts and were mauling them. Sucking, kissing, licking, and biting her nipples. Cole too didn’t last very long but he too came loads inside Kaitlin’s pussy. Meanwhile the pain from her nipple torture pushed Kaitlin over the edge again. With no dicks in her mouth, this time she uttered a high pitch squeal and arched her back as her orgasm overcame her.
Kaitlin finally got half a minute to relax down. She lay half dazed on her back, palms under her head, exhaling audibly through her mouth. She felt Cole and Shane’s cum flowing out of her pussy and running towards her buttcrack. The boys too caught their breath and admired their prize, high fiving each other. One of the boys removed her top that was pointlessly hanging by her neck.
“Alright, that’s enough rest. Now get up and get us all hard again”, Mark said.
Kaitlin was still laying on the floor catching her breath.
“Bitch, did you not hear him?”, Dan yelled as he slapped Kaitlin’s breast.
Kaitlin yelped in pain and surprise but sure enough got off the floor immediately onto her knees.
The boys were seated, two each on either side of her. Kaitlin rotated through the four cocks three at a time. One in her mouth and two in her hands. In addition to the saltiness of the boys’ cum, she could taste a sweetness on Shane and Cole’s dicks which she realized was her own pussy juice. She could feel her mouth working its magic and the boys’ cocks getting hard again.
“Ok, that’s enough”, Dan stopped her after a while. “We need to make use of this now”.
The boys decided they would next team up in pairs and take Kaitlin from either end. Mark, who had yet to try Kaitlin’s pussy was eager for it. They positioned Kaitlin on all fours. Mark went behind Kaitlin and fucked her pussy doggy style while Cole throat fucked her. Dan and Shane were recording photos and videos.
“The Bitch looks so good taking a spit roast”, one of the recorders commented.
Kaitlin had an odd mixture of fear and excitement. She had no doubts that she was completely at the mercy of the boys and would have to submit to their domination. She was angry that she had allowed herself to surrender to the boys like this. She was no longer their coach, but their sex object who would have to do their bidding. The loss of control over her fate to her students was a new feeling to her and greatly excited her.
“Now that they’ve already cum once, they’re going to last much longer. Strap in Kaitlin”, she thought to herself. She could feel pain beginning to start in her pussy.
Kaitlin came a third time but the Mark and Cole showed no signs of slowing down. They high fived each other from either side and posed for the camera.
“Here we have the Eiffel Tower. Doesn’t the base look sexy?”, Dan commented and the boys laughed. Kaitlin was pink in embarrassment but was building up again.
Ten minutes later, Mark was finally at the edge. “I’m gonna cum”, he remarked. Cole was also ready. He took his dick out of Kaitlin’s mouth and ordered her, “Look at the camera, bitch”. Kaitlin’s eyes widened in shock at the words from the until recently virgin Cole. A slap on the face from Cole got the message through to her a second later. Kaitlin looked straight into the camera with her orgasm face. Eyes wide, mouth open, and a long steady wail coming from her mouth. All her pussy muscles unclenched and Kaitlin got her biggest orgasm so far, squirting a big volume of liquid from her pussy. Her legs collapsed and Mark had to hold her in position by her buttocks as he became the third boy to cum inside her pussy in the last half hour. Cole came too, and his cum landed on Kaitlin’s hair, eyes and mouth.
Mark removed his cock from Kaitlin’s pussy as it made a soft “plop” sound. As he let go of Kaitlin, she collapsed on her side, her eyes still looking into the camera.
“Would you believe it, our coach can squirt”, Dan remarked and took the camera over to Kaitlin’s legs where a small pool had formed. He ran the camera all over Kaitlin’s body.
“All right, I’ve waited long enough. Our turn now. Let’s go Shane”. Dan handed over the camera and positioned himself behind Kaitlin and lifted her up. “Hold your position, bitch”, he slapped her on her ass, causing her thick ass to jiggle. Kaitlin, whose muscles were already spent, tried her best to re-engage them and hold herself steady. Shane was happy running his hard dick against her face and slapping her cheeks with it.
From the back, Dan remarked, “Uh oh. Looks like this pussy is overused. Too much liquid. I need something tighter”. Dan lined his big dick against Kaitlin’s asshole.
“Oh God noooo, not my ass please”, Kaitlin begged as she realized what was happening.
“Shut up bitch. Didn’t you say you’d done anal before?”, Cole remarked from the side.
“Good thing we have lube available “, Dan said. He quickly inserted his penis in Kaitlin’s soaked pussy and pulled it out. He realigned his dick that was coated with Kaitlin’s juices against her ass and pushed in.
“Aaaaarrrrgggghhhhh” Kaitlin screamed in pain as Dan pushed the first five inches of his dick inside her ass.
“Fuck, her ass is so tight”, Dan groaned.
Kaitlin’s scream was replaced by a deeper, guttural groan as Dan pushed the rest of the way in. After three or four strokes, Dan finally got a rhythm with which he was thrusting in and out. He could feel Kaitlin’s sphincter clenching tight with each stroke. Neither Kaitlin nor Dan lasted very long this time. Kaitlin screamed and squirted another waterfall this time until she felt every drop of water in her body had been used up. Dan came inside her ass and as he pulled out, the boys could see his cum oozing out of Kaitlin’s asshole for a gorgeous anal cream pie. Shane painted Kaitlin some more and got her along her left side as he came on her ear, neck, shoulder and chest.
With her fifth orgasm, and her body and brain overwhelmed with pleasure and pain, Kaitlin passed out.
“Time for a break boys”, Dan remarked and he handed a beer each to the boys. “Here’s to Kaitlin”, he said loudly as he raised his can. Together the 4 boys cheered and toasted to “Coach K”, “Kaitlin”, “Our Bitch”, “Cole’s first pussy”, “Coach Squirt”, “Coach Cum Dump” and other degrading names they could think of. They admired their beautiful handiwork.
Kaitlin was sprawled on her knees and on her right cheek. Her breasts were squished against the floor and her ass hung in the air. Her face was painted in cum stains and Dan’s cum was still oozing out of her asshole. Remnant juices dripped down her pussy onto the pool below which had grown considerably.
“Let’s turn her around”, Mark suggested after they had recorded her from all angles. Together they flipped her over onto her back. A loud squatch sound was made as Kaitlin’s thick ass hit the wet floor. They spread her legs as wide as they could, raised her arms over her head and surveyed her body again.
Her peaceful, innocent looking face. If you could look past all the semen, that is. Her gorgeous white, shaven, sweat-stained armpits. Her beautiful breasts pointing at the ceiling with some pink bite marks visible on them from the boys’ excess eagerness. Her toned stomach heaving up and down with her chest. And then her beautiful clean-shaven pussy. It had turned a dark red from the pink earlier. Her well-worked clit was hiding beneath its hood. Her pussy lips were spread wide and the pussy hole was fully expanded front and center. A cocktail of semen and Kaitlin’s juices were spilled everywhere. A trail of liquid ran down to the back of her right knee.
“Say what you want boys, but this beautiful bitch is strong. She lasted a long while. Which only makes this more fun”, Shane remarked.
“Yeah, don’t forget, she already swam a quarter mile sprint before all this”, Mark added.
“Yeah, that was a great idea Dan. This whole thing worked out better than anyone could have hoped”, Cole added.
“Thanks guys. But I think I’m starting to feel ready for our hot coach’s body again. So let’s wake her up”.
Cole poured his remaining half can of beer down Kaitlin’s face and hair. That woke Kaitlin up suddenly as she sat up gasping and coughing.
“Boys, I think we now try and fill all her holes at the same time”, Dan proposed.
Kaitlin was helped up and positioned in a cowgirl position onto Cole who lay on his back on the floor. Shane this time lined up behind Kaitlin and ploughed his dick in Kaitlin’s used ass, eliciting squeals of pain from her. Dan sat near Kaitlin’s mouth and she didn’t need telling as she closed her mouth around Dan’s dick while Mark filmed.
Kaitlin could taste the pungent, rancid taste of her asshole on Dan’s dick. She was surprised to find herself turned on by the degradation and prostitute-like treatment of hers by the boys. Every thrust from Shane in her ass led her to deepthroat Dan more on the other end. The triple penetration quickly overwhelmed Kaitlin and she climaxed multiple times. Or maybe it was one long orgasm. Kaitlin couldn’t tell. But her body was twitching for over a minute as Shane became the second person to dump his load in her rear.
Shane swapped places with Dan and ordered her, “Clean my dirty cock you bitch “. Kaitlin did not hesitate and licked his cock clean and dry. Despite the stinking taste on it from her rear end.
The 4 boys swapped positions numerous times, trying all the combinations they could. They ensured that everyone had dumped their cum into each of Kaitlin’s three holes. Kaitlin’s mouth, pussy and ass had long felt raw, chafed and burnt but she was riding the pain-pleasure balance. Kaitlin orgasmed many more times throughout the drive back. She squirted five more times, and kept passing in and out of consciousness while the boys had their way with her.
With about a half hour remaining in the drive, the boys too were spent. A dazed Kaitlin was relieved to hear when Dan said, “you’re free bitch”. But seconds later, the van pulled over and a sliding door was opened from outside where stood their van driver Charles.
Charles was a fat fifty something year old Black man who was employed by the school as one of the drivers. He too had been smitten with the tall, beautiful brunette rowing coach ever since she’d joined the school. But never thought he’d ever get a chance with her. “I been seeing what you boys up to with this woman. If you want my silence, Charles wants a slice of the cake too. Take a hike and don’t return for half an hour, he ordered the boys”.
“Oh no, not again”, Kaitlin groaned internally. The boys quickly clothed themselves and departed as Charles entered the van and slid the door shut.
While Kaitlin’s holes should have been well accustomed to penetration by now, Charles’ 10 inch BBC presented her with more pain. Charles took Kaitlin in both her pussy and her ass. “Under normal circumstances, I’d never be found close to this ugly man”, Kaitlin thought to herself. Charles perhaps sensed it too. Kaitlin screamed continually as Charles rode her hard, especially in her ass. After a while, the only sound from Kaitlin was this guttural animalistic groan or wail of a noise, as Kaitlin kept coming over and over on Charles’ dick. After he had become the fifth person to cum in Kaitlin’s ass that night, Charles too made Kaitlin suck his cock dry clean. Which she did without a complaint.
When the boys returned, Charles told them, “That was well worth it. But I want you boys to have this van all cleaned out. I’ll leave the side doors unlocked and the van parked in the usual space. You have all of tomorrow, but I want this fully clean before 5 am Monday”.
The boys got in and helped Kaitlin into one of the seats as Charles drove them towards home. They used Kaitlin’s white tank top to clean as much of the liquid they could in the car. The rest they would have to deal with tomorrow.
They each wanted to keep one piece of Kaitlin’s clothing as a souvenir. Which would mean Kaitlin having to walk the last 5 minutes in her apartment complex to her apartment door completely naked. She begged the boys to let her have her clothing back. But the boys wouldn’t relent.
“You can keep my bra and panties but atleast give me my shorts and top back please”, she pleaded.
The boys finally agreed to a deal. The underwear was off limits. They were going to keep it. Kaitlin could either have her tank top, or her grey shorts, not both. And in return, she’d need to join them tomorrow afternoon to clean the car in an outfit of their choosing. Kaitlin agreed, and chose her tank top. She used it to clean as much cum as she could off her body and then put it on.
She was thankful that the top was long enough that it at least came down to her upper butt. While not ideal, from a distance it gave the illusion that she may be wearing panties underneath. The top was completely soiled however. Thanks to all the liquid, it was completely sheer and was discolored in places with beer, sweat, and bodily fluids.
Kaitlin was dropped off first. Charles pulled over next to where a couple were standing on the sidewalk. Kaitlin carefully got out of the car and saw the man’s eyes widen in surprise as she realized she had just flashed this man. Embarrassed, she turned and walked as fast as she could without letting her top ride up. The boys watched as Kaitlin entered her building with her hands holding her top down. Her lower butt cheeks exposed and jiggling with each step.
In the apartment building, Kaitlin luckily didn’t run into anyone she knew, but the three strangers she passed all double backed to confirm they were seeing what they thought they were seeing.
Kaitlin got into her apartment, collapsed on her bed and was knocked out in her soiled top and her shoes before her head hit the mattress. She slept 12 hours straight.
Next morning, Kaitlin prepared a hot bath for herself and cleaned herself out thoroughly. She remembered the events of the evening before and masturbated herself twice in the tub. As she was getting out of the shower, her phone buzzed multiple times. The first message was a video attachment from the night before. It showed her in a dazed, ragged state, being triple teamed by Mark, Shane and Dan, and begging them for their dicks as she was squirting.
The second text said, “Same top as yesterday. Cut it 6 inches from the bottom and make it distressed. Distressed jeans shorts. If not distressed enough, we will rip these for you. No underwear. High heels”.
The third text had the location of the school garage, 1 mile away. “Show up on foot. In 30 minutes else we release the video”.
“Oh shit, oh shit, oh shit”, Kaitlin muttered as she hurriedly found her scissors, yesterday’s top, and the only pair of jeans shorts she possessed, which had been an expensive gift. She hurriedly made holes in both pieces of clothing, some bigger than she intended in her rush. She checked her outfit in the mirror and was pretty satisfied with it despite all the skin she was showing and her designer jorts basically ruined. She put her heels on, and saw that she had only 15 more minutes. Sighing internally, she grabbed her keys and started running as fast as she could to her destination.