Shoesession

americanguy wrote: ↑Thu Jul 11, 2024 12:14 pm Okay - a bit more of this fun story for you all on a hot as hell Thursday:

Chapter 2 - In Her Mouth

The next morning Jess woke up and wondered if it had all been a dream. Had Mr. Smith really slipped her beloved white ON Cloudmonsters off her feet and fucked them right in front of her? Had she really agreed to wear them sockless and full of his hot sticky cum every day? Was she really going to go back to his office and let him do it again today?

As she sat up in bed and looked around her room, she saw her ONs sitting on the floor next to her desk chair, right where she had left them last night. She remembered slipping them off her feet and feeling Mr. Smith’s cum, by that time cooled, sticking to her toes. She also remembered looking down at her innocent little sneakers and thinking to herself how hot it had been watching her stats professor pound them into his desk with his massive cock before blasting his load of hot, sticky cum right into them.

Jess had never imagined she would be in this position.

But as she glanced at the clock she realized it was time to get ready to head to Mr. Smith’s class once again - a class she happened to be failing at the moment, so she needed to make Mr. Smith happy if she wanted to pass.

Jess got dressed in a pair of black Lululemon leggings, a white oversized hoodie sweatshirt, and of course her little white ON Cloudmonsters, which still looked perfectly clean to a stranger but Jess knew better. With no socks on as he had instructed, Jess could feel that Mr. Smith’s hot load had dried overnight. She also knew he would insist on putting another in its place after class today.

As Jess was packing her bag for class, she glanced through her open closet door to her sneaker collection. As it happened, Jess was a bit of a sneakerhead herself, and had somewhere around 70 pairs of sneakers. Everything from ONs to Nikes, Adidas to Brooks, Mizunos to ASICS - you name it, and you could guarantee she had a few pairs. With her mind still playing yesterday’s events on loop, she wondered if Mr. Smith might like to try another pair too - as a treat. The thought of watching her professor fuck another pair of her sneakers turned her on even more, so she walked over and examined her options. Clearly he liked her pretty white ONs, so maybe something else similar? How about her brand new white Nike Pegasus that she had yet to wear at all - “yes those should do,” she thought, before picking them up and slipping them into her school bag with her laptop.

As Jess walked across the quad to class, she couldn’t help but imagine what would happen when she got to Mr. Smith’s office after class today. Would they have small talk first, or would he just take her sneakers off her feet and immediately start fucking them? She wasn’t sure which she would prefer. If she was being honest, she wasn’t even sure how she felt about this whole situation. In her wildest dreams she had never imagined she’d be letting anyone, let alone a professor, fuck and cum in her beloved sneakers - yet whenever she thought about yesterday’s activities she could feel her pussy start to drip. She simply couldn’t believe how turned on she got watching Mr. Smith slide his massive cock in and out of her perfect little Cloudmonsters.

Suddenly she looked up and realized that her daydreams had distracted her and she was already standing right in from of Mr. Smiths classroom door. Taking a deep breath she opened the door, walked in, and took her seat in the back of the room, the whole time thinking about the cock that would soon be sliding across her insoles.

Class dragged by as slow as ever - every word out of Mr. Smith’s mouth seemed to take twice as long as normal. Jess couldn’t help but notice his stunning sharp features and muscular build all over again. She also couldn’t keep from recalling the big, beautiful dick Mr. Smith was hiding under his nondescript slacks.

As class came to an end, Jess caught Mr. Smith shooting glances at Jess, eyeing her feet to make sure she had her Cloudmonsters on as agreed. She saw a smile creep onto his face whenever he caught a glimpse of them - only she knew that his devious expression was one of desire for her perfect little ONs.

The bell rang, and her classmates started to trickle out, until finally it was just Jess and Mr. Smith. He slowly raised his gaze and motioned for Jess to come down to his desk. She stepped forward and silently walked to the front of the room - Mr. Smith’s eyes on her feet every step of the way.

“Hello, Mr. Smith,” Jess said.

“Hi Jess. How did you like wearing your Cloudmonsters sockless after our conversation yesterday?” he asked, a devious note in his voice.

“I liked it more than I thought I would. At first I was nervous, but in the end, it made me so incredibly horny seeing what you did to my innocent little sneakers, and getting to feel the treat you left between my toes for the rest of the day.” As she spoke, her hands started to shake ever so slightly as she stood before the man who held her future in his hands, knowing that all he wanted in order for her to pass his class was to get to fuck her sneakers over and over again.

“Good,” Mr. Smith said. “Then you won’t mind following me to my office for the next round of our agreement.” He stood up, turned on his heel, and started walking to his office door. Jess followed quickly behind him. She could feel her panties getting wet as she dripped in anticipation of what was to come. “What does it say about me that I’m so excited to see my professor slide his cock into my sneakers,” Jess thought to herself as she crossed the threshold into his office and took a seat in the chair opposite Mr. Smith’s desk.

Mr. Smith sat down and looked Jess over from head to toe - his eyes stopping first at her chest, and then sliding down past her hips to her feet, where her Cloudmonsters were gently sticking to her sweaty soles as her hot little toes warmed the shoes that would soon be wrapped around his member.

“Jess. You did quite well last time we spoke, and as we agreed if our little arrangement continues you will find much success in my class.” He said, his eyes snapping away from her feet to lock with her own, a devious anticipation hiding behind the sparkle in his grey green retinas. “But if you want your grades to be excellent, your performance here with me must also be excellent. Do you understand?”

“I think so, Mr. Smith,” Jess said tentatively. “In fact, I brought a second pair of my sneakers with me today too - do you want to see them?”

“I can’t imagine anything could compare with your Cloudmonsters, but I’d be happy to see any pair of sneakers you have worn,” Mr. Smith replied, a hint of excitement hidden in his voice.

As Jess turned to her side to retrieve the Pegasus she had stowed in her bag, she felt Mr. Smith’s hand on her knee. As she looked back at him he lifted her legs and placed her ON clad feet right in his lap, one on either side of his cock, which she could now see bulging beneath his trousers. For a moment she was nervous and considered backing out - “was this really worth it for a grade?” she asked herself. But in an instant that hesitation was gone, and she pulled her Nike Pegasus out of her backpack.

“Actually Mr. Smith, I haven’t worn these at all yet - they’re brand new,” she said as she placed them on his desk. The white of her new Nikes shined brightly against the brown wood of his desk. Mr. Smith looked at the perfect little Nikes on his desk before looking back to meet Jess’s gaze. His hands were still cupping the heels of the Cloudmonsters on her feet, and she could feel his cock growing larger and larger just beneath her soles. In fact, she could feel it starting to pulse, begging to be released from the prison of his pants and plunge into her sneakers.

“These new Nikes are quite nice Jess, and you assumed right, they are in fact a pair I would love to fill with my load. I’ve noticed your impressive sneaker collection over the course of this semester, and there are many pairs I’d like to enjoy, but for now, we’ll keep our focus on your cute little ONs - how does that sound?”

Jess just nodded - she was so focused on what she had just heard; Mr. Smith had been eyeing her sneakers all semester, not just since she arrived at his office yesterday? Does that mean there are other pairs she could offer to let him fuck in exchange for even more perks?

Jess snapped out of her daze to feel Mr. Smith’s fingers sliding into her sneakers, down under the laces, feeling her bare arches in her perfect little shoes. “I’m going to fuck your perfect little shoes again today Jess. And I’m going to pump a massive load of my hot sticky cum into them. And then you’re going to continue wearing them sockless with my load in them - that is if you want to pass my class, of course,” he said with that devious smile of his.

“Oh of course, Mr. Smith. I wouldn’t want it any other way. I’ve been dying to watch you fuck my sneakers against your desk again today,” Jess murmured. She could barely speak she had gotten so turned on feeling him caress her feet with her shoes pressed against his rock hard cock.

Mr. Smith slid his hands up to her laces and gently untied her sneakers, before once again slipping them off her bare little feet one at a time. “Well actually, Jess, we’re going to change things up a little bit today,” he said, while raising her shoes up to his face and inhaling a giant breath of her warm feet and shoes mixed with his dried load from yesterday.

“If you want to pass my class, you’re going to need to put in the work. You understand that, right?”

“Yes of course, Mr. Smith. Whatever you want, I’ll do anything.”

“Good,” Mr. smith said. “Now take this, and hold it just like that.” He handed her her own right Cloudmonster and gestured that she should hold it between her thighs, toe pointed up toward her chest, the hole for her foot pointed right at Mr. Smith and the sole resting right on her now dripping pussy.

“Now I’m going to fuck your cute little ON right here, right against your tight little pussy, because I want you to feel it every time I thrust into them. I want you to feel my cock pounding the inside of these sneakers you love so much, and I want you to know exactly how I’m dominating them. Do you understand?” his voice firm yet laced with desire.

“Yes, I understand. I want to feel everything you’re doing to my sneakers.”

Without another word Mr. Smith lifted Jess’s other shoe to his face and inhaled a giant breath before reaching down and unbuttoning his slacks, releasing his massive, rock hard cock from its textile prison. It looked so big that Jess would never imagine it would fit in her cute little shoes, but she knew from experience that it would.

Mr. Smith closed the distance between them in just two paces before straddling Jess right where she sat in the chair across from his desk, and slowly, in fact surprisingly gently, slipping his cock deeper and deeper into the sneaker positioned right in her pussy.

She could feel every millimeter that he proceeded. She could feel him pushing his dick past the tongue of her perfect little shoes - she could feel the laces pull with gentle tension as his massive member slid further into her shoes, and by extension across her own pulsing pussy.

She gripped the heel of her shoe with one hand, and laid the other hand across the laces, applying gentle pressure to Mr. Smith’s cock. He began to thrust in and out - his shaft seemingly going on for miles as he withdrew it almost entirely before he changed direction and began penetrating her shoes once more. With each thrust and pull, she imagined he was thrusting into her instead - it certainly felt like he was with her shoe sitting right against her moist, sensitive thighs - the sole rubbing her clit with every stroke he took.

"Yes, professor, fuck my little white sneakers! I love the feeling of your hot sticky load between my toes! I wore these all day yesterday just like you told me too, and I didn’t clean them at all. Oh, I can't wait to wear your cum around in them, FILL THEM, FILL THEM WITH ALL YOUR CUM!” Jess began to raise her voice as the excitement built. But this time it wasn’t just the excitement of watching her innocent little shoes get fucked in front of her - it was feeling every move her professor made right against her tight little pussy. In fact, she quickly realized that she herself was about to orgasm.

As if he saw the thought cross her face, Mr. Smith snapped “You absolutely may not finish unless I tell you - or you will be punished.”

“I don’t know if I can last much longer,” Jess replied.

“Good, then I will go first,” he said before thrusting hard one final time, arching his back, and shooting the beginning of a massive load right into her ON Cloudmonster. With every spurt she could feel her sneaker pressing harder and harder against her pussy. Suddenly he pulled his cock out of her shoe, took one big step forward, stood all the way up and slid it into her open mouth.

Before she even had a moment to realize what was happening she was choking on his massive cock, and she could feel his sticky load pouring down her throat. Now that she had him in her mouth she realized just how huge he actually was. She could barely fit him between her lips, and as her brain caught up to her body, she realized how much she loved it. She loved knowing her Cloudmonster was now full of his Jizz, and she also loved tasting the rest of it shooting down her throat. She started to suck harder, massaging the head of his cock with her tongue, urging him to give her everything he had.

She let go of the sneaker in her lap, grabbed him by the hips and pulled him forward, taking every inch of his massive cock down her throat as he pumped the last of his load into her cute little college girl face.

She let go and he gently drew away, sitting down in his desk chair to catch his breath as he looked at her.

Jess could still feel her pussy tingling - she was right on the edge about to cum, but she knew what Mr. Smith had said - she had to make him happy.

“Do you want to feel an orgasm now, Jess?” Mr. Smith said gently.

“Yes,” she whispered.

“Good. Grab hold of your cute little ON, and use the toe to rub your clit until you finish.”

Without hesitation she followed his instructions, and it didn’t take long. The smooth material felt incredible sliding between her thighs, as she rubbed it back and forth between her legs. Within moments she could feel the organs starting. She arched her back, closed her eyes, and kept rubbing as she felt wave after wave of euphoria pass over her. It was without a doubt the best orgasm she’d ever had.

After a moment she stopped, caught her breath, and opened her eyes. She looked up at Mr. Smith. He had the same devious smile he had earlier, but this time there was more to it. It seems he enjoyed watching this 21 year old brunet orgasm in his office using only the sneaker he had just finished fucking.

“Good work today, Jess,” he said gently, zipping his pants back up as he did. “That definitely puts some points back in your grade for the semester. But remember our rules - you have to wear these Cloudmonsters to class every day, you have to wear them sockless, and you have to let me fuck them after each and every class. Do you understand?”

“Yes, of course Mr. Smith. Whatever you want, I will do,” Jess replied.

“Good, now put your Cloudmonsters back on your feet - you have another class to get to.”

Jess did as she was told, slipping her ONs back on her feet and tying them tight so she could feel the cum push up between her toes.

She stood next to Mr. Smith’s desk and reached to retrieve her Pegasus to put them back in her bag but before she could Mr. Smith caught her wrist and said “No, I’ll hold on to those for now. They are going to be my dessert. Now you should go before you’re late.”

Jess was shocked. She hadn’t expected to have to leave her brand new Pegasus with Mr. Smith - she hadn’t even gotten to wear them yet! And what was he going to do with them? Presumably fuck them over and over tonight, filling them with his loads, ensuring they would never be white again.

A feeble “yes, Mr. Smith, whatever you want” was all she could muster before she turned and walked out of his office - her feet squeaking in the massive load in her sneakers, her heart dropping at the thought of leaving her brand new sneakers behind, but her pussy tingling at the thought of what they might have done to them overnight.

She didn’t make it very far down the hallway before she got a notification on her phone - it was an email from Mr. Smith. The subject line read “Don’t worry, I’ll treat them well”

Jess knew it must be about her Pegasus that she had left behind, so she opened it, and there on her phone screen was a picture of Mr. Smith’s massive cock (still with streaks of his cum dripping from it) sliding into her brand new, pristine white Pegasus.

When she saw it, she instantly felt a surge of emotion like she had never known before. She wanted to be there, holding her sneakers as he fucked them. She wanted to feel his cock thrust into the shoes she hadn’t even gotten to wear. All her fear and hesitation melted away and she knew one thing for certain: she wanted to be Mr. Smith’s little sneaker bitch, and she wanted it now.