Autumn's Problem Ch. 01

Devin was so very glad he signed up for the adventure club class for summer semester. He had no idea at the time how awesome an idea it would turn out to be, but on this day, he thanked himself again for signing up for the class. The class was out on a four-day forest backpacking trip, and the majority of his classmates were girls by some strange stroke of luck. He was walking behind a walking wet dream. At five feet and eleven inches, with a golden tan, curly brown hair and chocolate-amber eyes, Autumn could draw the eyes like few other girls. She was wearing a mid-thigh white pleated skirt and a peach-colored camisole, with a sturdy pair of hiking boots. Her front strap for her frame backpack cut above her perky breasts and made them seem to stick out even further. She was usually all smiles and pleasant with Devin, but yesterday she was a bit cranky and today she seemed quite a bit more so. She had caught Devin looking at her derriere and scowled at him earlier, and he had looked away from her in embarrassment.

Around mid-day, the "instructor" led the group to a mountain overlook, and told everyone to take a 1-hour break. Devin sat down on a rock and started rummaging through his pack for lunch, and was just pulling out a bag of trail mix and jerky when he saw that Heather and Sarah had joined him, sitting on the rock facing him. He figured they were there to bum some snacks off of him since he had brought a much bigger frame pack and had more food than most, but when he held up the bag of trail mix, Heather waved it off with a tense smile, then looked to Sarah, took a deep breath, and addressed Devin.

"Hey Devin, we have a pretty big favor to ask you, and it's super uncomfortable to ask you for it, but since she is too proud to say anything, we're going to do it for her."

Devin wondered who "she" was and why she didn't want to ask him directly, but Heather got right to answering his question.

"You remember how you dated Krissy last year? Well, she told us how you talked her into trying some different positions and stuff, and specifically anal, and how much she loved it. We noticed that you kept discrete about it and didn't share it with everyone in school. Us girls know because we talk, a lot. Well, anyways, we have a bit of a problem and discretion is super important with this issue, so we couldn't think of anyone else who we might be able to ask without it getting out. We are hoping you can help us with a super-secret problem and swear never to tell a soul."

"Well, I don't know what you want me to do, but I can promise that I won't speak a word about it to anyone" he replied.

"Okay, good" Heather continued, "We are trusting you bigtime with this one, and if you can help and keep it a secret, I'll owe you all kinds of favors."

"Shoot then" he replied.

Okay, you probably don't know this, but Autumn has a health condition that causes her to get, umm, backed up if you know what I mean, and she has to like, do a procedure pretty often to keep herself healthy and regular. The problem is that she left her bag of supplies for doing the procedure in her car at the trailhead, and now she really needs those supplies." Heather said, waving her hands animatedly.

"Whoa, holdup. There's no way I can go back to the trailhead. We're a day and a half of walking away from the trailhead, and it would take a day and a half to get back," Devin blurted.

"Well, yeah, we know that, but we think we've figured out a way to help Autumn with her problem, but it's going to be awkward for the both of you, and if the story got out, it could ruin her socially."

"Okay, I'll help out in any way I can," Gavin offered.

"Thank you so much. We're going to talk with Autumn, and we'll get back with you later."

Devin watched the tight asses of Heather, the freckled redhead, and Sarah, the platinum blonde as they jogged up ahead to talk with Autumn. After a few minutes of quiet talking, the girls started hissing replies back and forth rapid-fire until Autumn shook her head no and made a cutting motion with her hands, signaling she was not keen on whatever her friends had proposed.

For the rest of the afternoon, and leading up to the evening, Autumn wouldn't even look at Devin, and wore a constant expression that ranged from pissed-off to grimacing. Devin figured whatever the girls had suggested was never going to fly, so he tried to forget about it as they entered a clearing and started setting up their tents for the evening. After a campfire dinner of reconstituted dehydrated "pasta" and "meatballs" while talking to the small group of guys at the trip, Gavin had retired to his tent to roll out his bedroll and sleeping bag, when someone tapped on the tent and hissed, "Gavin."

He unzipped the tent door to find Heather looking at him, with Autumn standing a few paces away, turned the other way, and Sarah holding Autumn's hands in a supporting gesture. Heather ducked into his tent and zipped the zipper closed. She took a deep breath, sat back on her heels, and rested her hands on her knees, then started."

"Autumn is very constipated and in pain, and needs your help. We don't have an enema kit or even a suitable water bottle, as everyone brought filter straws to drink straight from the streams per the class instructions, so we were wondering if you could help Autumn DISCREETLY." She continued, "Autumn really doesn't want to do this because it is embarrassing, and I think she kind-of likes you, so she doesn't want to destroy her chances with you, but if we don't do something, she may have to be airlifted to a hospital. She hasn't had a...um...'poop' in four days and she is in pain. We need you to, um, put your thingy in her...uh...back-door, and..."

"Wait, wha.."

"LISTEN...please. We need you to, uh, pee in her butt. It's the only way she can go to the bathroom sometimes. She needs an enema Devin, and she can't get one, and this is a medical emergency. We were thinking, since you seem to be very discrete, and supposedly like butt stuff, that you might find it in your heart to save Autumn tonight. She has been crying all day, and is really stuck with no better options. Can you do this for Autumn?"

Devin was reeling from the reveal, and sat there slack jawed while growing a huge stiffy thinking about Autumn's incredible butt. There was no way Autumn didn't do squats every day as her butt was 10/10, and he was being begged to put his dick in it?

Heather took his silence as reluctance, so she continued, "Look, if you do this for Autumn, I will give you blowjobs any time you ask for a month. Hell, I'll let you fuck me or do my butt for a month. Sarah agreed she would too. Just, please???"

Devin found himself unable to answer, but his mouth started moving for him. "Okay, yeah, I'll help Autumn, because that has to suck and I don't want her to suffer, but I'll hold you both to it."

Heather stuck out her hand and shook his. "Deal."

"So, how are we going to do this?" Devin asked.

"Just wait in your tent for a bit. All three of us packed in a big tent and we're sharing it. We should probably do it while everyone is still sitting around the fire chatting. We'll come bring you to our tent and we'll do it in there. Will you be able to pee or do you need to go drink some water?" Heather asked as she pointed at his water straw.

"Let me go drink a bit more, and I'll wait for your signal."

"Okay, and Devin...Thanks a ton. We really appreciate your help."

"You're welcome. You're a good friend of Autumn's, and I'm glad she has people to help her out."

Devin walked to the stream and gulped down water for a few minutes, then sat in his tent and waited anxiously. He thought back to high-school, where the terrible trio of girls ruled the roost, and how he had been pining for Autumn for years. It might not be an ideal situation, but he was going to remember tonight for the rest of his life if not for getting to see Autumn naked, then getting to put his dick in her butt. Autumn was his ideal woman. Smart, athletic, usually very nice, but still unattainable due to her absolute perfection. Devin had spent many a night beating the meat thinking about Autumn's sculpted ass. He was lost in contemplation when a hand smacked the side of his tent and made him jump a foot in the air. He opened the tent to find Sarah in her sleep shorts and a camisole with no bra. She waved for him to follow, then led him back to their tent.

As he entered, he found the woman of his dreams sitting on her heels facing the door, with Heather at her side. She had a sheen of sweat on her forehead, but her eyes were focused and she was looking straight into his soul.

Autumn started, "Devin. Heather says she has talked you into helping me out with my IBS, and that you have sworn to secrecy, but I need to see you say it while you look me in the eyes. Will you promise me you will never betray my trust in you, and carry this secret to your grave? Will you please keep this an absolute secret for life?"

Devin responded while looking her in the eyes, "Autumn, I swear to you I will not betray your trust in me. Whatever conversations I've had today and whatever happens tonight, I will never breathe a word of it to anyone outside this tent."

Autumn's shoulders relaxed a bit, then she continued with a concerned look, "Are you going to be able to do this without being grossed out by me after this?"

Devin took her hand, "Autumn, I think you probably know the saying 'I'd crawl through glass for the opportunity to sniff her farts' applies to how I feel about you."

All three girls giggled, and Devin continued, "But seriously, it won't bother me a bit, and actually might be fun for me at least."

Autumn searched his eyes, and seeming satisfied, said "Okay, then I'll try it. Thank you, Devin."

Autumn sat up and started shimmying her pajama pants over her butt. Devin was hard as a rock before she even started, but his cock throbbed in his pants watching the elastic stretch over her perfect globes of muscle. She was going commando, and Devin's breath hitched in his throat at the sight of her naked butt coming into full view. She was clean shaven, and she had a very meaty pussy. Her inner lips were small and uniform, and he thought to himself it was probably the prettiest pussy he'd seen in real life or online.

"Devin, take your pants off and give us girls a show," Heather offered.

Devin pulled his pajama pants down and his erection popped up as soon as it cleared the elastic. The girls gave appreciating noises at the sight of it. Autumn finished pulling her bottoms off, and was only wearing her peach camisole now, her fantastic legs and ass on full display in the warm glow of the lanterns. She hitched a couple of pillows under her pelvis, and put her head down, with her butt in the air. Devin felt a hand on his chest, then Heather leaned forward, grabbed his cock and closed her mouth over it. He felt her hot breath through her nose on the base of his shaft and his balls. She worked her way up and down his dick for a minute. Meanwhile, Sarah had spit in her hand, and was rubbing her hand over heather's butt. He could see her starfish glistening in the soft glow of the tent. It seemed pushed out, and stretched a bit. Sarah rubbed her middle finger along the crinkles and folds, and then pushed her middle finger into Autumn's butthole. Autumn had her head turned to the side, looking at Devin, and she moaned while looking him in the eyes. Devin smiled, then Heather pulled off his dick and spit on the end of it, and he knee walked up to Autumn's perfect derriere. He put his hands on the sides and spent a few moments running his hands along her perfect curves, and grabbed two handfuls of rump and kneaded them, with his thumbs rubbing along her pussy and her butt. She was positively hot and wet. She moaned with his ministrations, and pushed her butt back into his hands.

She smiled at him, and said, "okay, go slow."

Devin took his cock and lined it up with her pussy first, then pushed in. She was so slick and hot that Devin almost passed out from the sensations. He was able to go all the way in in his first push, and he felt her moisture coat all the way up to his pubes. Autumn moaned "yess," so he continued to pump into her, rubbing his thumb along her pooper. It was bulging out a bit and he felt like he could tell there was pressure behind it. He pulled out and stuck his thumb into her pussy to collect some lubricant, then pushed his dick back home and rubbed his thumb around her butthole and started applying pressure. His thumb seemed to slide right in, and soon he was feeling a hard, large mass at the limits his thumb could reach. Autumn jumped a little when he pushed against the mass, so he withdrew his thumb and patted her meaty butt.

"Sorry, just getting us both really slick" he said, then followed with, "are you ready for this?"

Autumn turned her head back to look at him, forced a smile, took a deep breath, and nodded. Then, he pulled out with a groan from her and lined up at her back door. The crinkles of her butthole pushed in with his pressure, resisting his entry, then he felt her open up a moment later. He inserted the head of his cock, then waited for her to adjust. She turned her head, and said "what are you waiting for, go ahead!" She seemed to relax a lot faster than girls he had been with before, so he cautiously pushed forward. He encountered a hardness about two inches in, and Autumn flinched. He figured he had encountered her constipation. He sat still and tried to pee, but it wouldn't come out.

"Are you peeing yet?" Heather asked.

"No, it's hard to pee when I'm totally hard. I need to go partway soft in order to pee."

"Well, hurry up. I'm in pain and this is all so embarrassing" she shot back.

"My grandma has diabetes, and her feet have flaky skin that dusts off when she takes her socks off" Heather offered.

Autumn and Sarah giggled and said "gross Heather, WTF?"

Heather replied, "There's no way he's going soft in your sexy booty without a gross image in his mind, so I figured I'd help out."

"Well, it worked" Devin replied as his cock had softened enough that he felt himself start to pee. He felt his bladder flowing into Autumn's butt, and Autumn sighed.

"Wow, that feels warm," Autumn commented, then rolled her butt around, seeming to be attempting to get his stream around the mass. "Really warm!" she continued.

She wiggled her butt on his cock and it slid a bit deeper in. The obstruction he had felt was no longer in the way, and Autumn pushed herself even deeper as he continued to empty his bladder. Autumn started sliding back and forth on his cock and he felt it hardening again as her ring massaged it up and down. He finished emptying his bladder just as his erection would have blocked him from peeing any more.

"Okay, now I have to let it sit and do its job for 10 minutes or so," Autumn said, and Devin started to pull out.

"STOP! I mean, don't pull out yet. It feels okay with you in there. I'm not ready for you to pull out yet." She wiggled around a bit more, then pushed her butt against him, sliding his dick even further into her perfect ass. She worked up and down for a minute or two, going deeper each time, until she had taken him all the way to the base. Then, she started fucking up and down his cock in earnest. Devin grabbed her by the hips and started driving himself in and out.

He looked over and noticed that Heather and Sarah had stripped off their clothes and were playing with themselves. He felt Autumn's fingers brush across the underside of his shaft and realized she was playing with herself. Heather got up and crawled underneath Autumn's side, then Devin felt the tip of her tongue rub up against the union between him and Autumn, and he realized she was going to eat Autumn while he fucked her in the ass. He looked over to her neatly trimmed pussy, and reached out and cupped it. It was already hot and wet. He slipped two fingers in her pussy while she ate Autumn. Sarah, looing dejected, huffed and got up and set her platinum blond and baby pink beaver in front of Autumn, and Autumn attacked it with her mouth. Sarah grabbed her hair and pulled her in after a minute.

His dick was starting to come out each time with a coating of light brown. He Autumn climaxed first, and her anal ring squeezed around Devin's dick, which set him off, and he started emptying his load into Autumn, who had forgotten her job at Sarah's shrine while she orgasmed. Sarah slid a finger into Heather's butt, and Devin could feel her finger through the membrane with his fingers in her pussy. Heather began bucking and moaning, and hummed a quiet orgasm.

Sarah groaned in frustration, and Devin realized that Autumn had passed out following her orgasm, leaving Sarah hanging. Devin pulled out of Autumn's butt and sat back, and Sarah jumped across the tent and attacked his cock with her mouth. Apparently, Sarah's innocent look was only a look as she ferociously took his dirty cock in her mouth, before climbing up and sitting her pussy down on his newly hardened dick. Devin grabbed Sarah's butt, and began fucking her hard while she gyrated her hips on his dick.

She smiled at him, then told him how much she appreciated him helping her friend, and leaned forward and kissed him, then told him that he should put a finger in her butt. He obliged, and Sarah redoubled her efforts while bracing her hands on his shoulders. He slid a second finger in her butt, which set her off into a whining orgasm as she clamped down on his cock with all her muscles while oscillating all over it. He shot a second load into her after a few seconds, then everyone passed out.

Ten minutes later, Autumn shot up, and started to throw on her pajama pants and said "OMG I need to go NOW!" Devin, please come with me! It's dark and I don't want to go out there alone. There might be bears!

To be continued...