Jess’s story - a rewrite

americanguy · Post by **americanguy** » Fri Aug 16, 2024 4:21 am

Hi friends - chapter 4 of Jess’s misadventure is now ready! Links to pictures of the shoes in this chapter coming in a follow up post. Enjoy!

Chapter 4 - The Misstep

A few days had gone by, each one with a similar trajectory. Jess would wear a pair of the sneakers Mr. Smith had fucked each day she went to his class, and she would bring along a pair that he hadn’t yet enjoyed. The first day she brought him her Nike Air Max 270 classics in white and black - she knew he’d love them, since he wore a similar pair himself.

A few minutes after class she was proven right when he fucked them right in front of her, making her hold them for him while he thrusted his massive cock in and out of them, before filling them up and spraying all the rest of his load all over her tits.

The next day, she wore those same 270s to his class, and brought him another pair of her ONs, this time a pair of silver Cloudultras that she had recently added to her collection and had worn only twice. Once again he loved them, and just like her Pegasus before them he took them home and fucked them time after time, sending her a few photo updates of exactly how he was treating them.

Then, it was the third day. Jess showed up to class wearing her little white ON Cloudmonsters, the first of her sneakers Mr. Smith had ever fucked. When he noticed them on her feet, Jess saw Mr. Smith give her a little peak at that devious grin she had come to know.

Once again the bell rang, and once again all of her classmates left the room while Jess stayed behind. She walked into Mr. Smith’s office, and sat in the chair in front of him, which had now become routine. She put her ON-clad feet up on his desk right in front of him, and he immediately started to caress her toes, working his hands over her sneakers and under her laces. As he felt up her feet, sneakers, and ankles, she reached down to her bag and pulled out another new pair for Mr. Smith - this time a pair of her Adidas Superstars.

Mr. Smith looked at the Adidas, looked at Jess, looked back at the adidas, and then back at Jess. He locked eyes with her and simply said “I’m not a fan.”

Jess’s stomach dropped. When they had re-written the rules of their agreement, Mr. Smith had told Jess that if she brought him a pair he didn’t like, that she would be punished. And now, after only 3 days, she had done just that.

Her mind began to race, and her heart began to beat out of her chest. “What would her punishment be?” she wondered to herself.

“I told you that if I didn’t like the pair you brought, you could be punished - and I’m prepared to follow through on that. Are you ready for that Jess? Or would you rather fail my class?”

“I guess im ready for my punishment, Professor,” she replied tentatively.

“Good. Now come over here and undress to only your Cloudmonsters, and lay down on this couch,” he said gesturing to the small futon to the side of his office.

Jess did as she was told - stripping down until she was sitting on her professors couch in nothing but her perfect little white Cloudmonsters that Mr. Smith had fucked and cummed in multiple times.

Once she was naked, Mr. Smith pulled a few things from his desk drawer.

The first was a length of rope, which he used to bind Jess’s hands together behind her back.

The second was the pair of ON Cloudultras that she had brought for him the previous day. They were both clearly filled with his cum, like he had fucked them each a hundred times.

Lastly, he pulled out a small tripod, to which he attached his phone.

“Now Jess, we’re going to have a little bit of fun, and I’m going to take a video of our fun.
If you bring me another pair of sneakers I don’t like, I’ll send the video to a few of your classmates who I happen to know also have a little thing for your sneakers, and I’ll invite them to join us for our next get together with your shoes. How does that sound?”

“Whatever you want Mr. Smith. You’re the boss,” Jess responded.

“That’s right Jess, I’m in charge here, and you’re going to do as I say. Now, I want you to lay down with your head at this end of the couch,” he instructed.

Jess did as she was told, laying her head on the end of the couch directly in front of Mr. Smith, and as she did, Mr. Smith tapped his phone to start recording.

He stood, placed Jess’s Cloudultras on the couch in front of her, and slowly unzipped his pants before taking them off entirely. He began to stroke his already-stiff cock, while looking a naked Jess up and down, stopping to focus on her sneakers, her tits, and her tight little pussy.

He continued to stroke his cock with his right hand, and at the same time grabbed Jess by the knees, lifting her feet up off the couch to his face, where he inhaled deeply, his cock getting harder and harder by the second.

He dropped her legs, took a step to the side, and plunged his now fully erect cock into Jess’s mouth. He began to fuck her face harder and faster as he went, ensuring she took every inch of him down her little 21 year old throat. She choked and gagged, but he didn’t relent. Finally, when she thought she could take it no longer, he began to cum. He blasted shot after shot of his hot sticky cum down Jess’s throat before finally pulling his cock out of her mouth, grabbed one of her sleek grey Cloudultras off the couch which he held just in front of her face. He shot his last few spurts of cum into it, as Jess let some of his load fall out of her mouth and right on the laces of her sneakers. They were totally covered in his cum, and Jess looked slowly up at Mr. Smith, wondering if that was the extent of her punishment.

“How did you like that, Jess?” he asked.

“I’m at your service, Mr. Smith. Your wish is my command,” Jess uttered softly, barely able to speak after the beating her throat just received from Mr. Smith’s massive cock.
“That’s right Jess, and we’re not finished yet,” he replied.

Jess’s heart sank as Mr. Smith sat down on the chair opposite her, where he began stroking himself once again, looking Jess over head to toe to get himself hard again.

As his cock began to grow, he reached out, grabbed Jess’s little white Cloudmonsters off her feet, and began to fuck them, a few thrusts in one before switching to the other. Back and forth he went until his dick was hard as a rock.

He grabbed Jess’s ankles, spun her 90 degrees, and lifted her legs over her head before running the tip of his cock over her right little pussy.

“Are you ready to see what it feels like when you disappoint me, Jess?” he asked.

He didn’t wait for her answer before thrusting his cock deep into her. He began to fuck her harder and faster than she had ever had before.

“Oh FUCK! Mr. Smith. Ohhhh. FUCK!” Jess screamed, which only egged him on even more.

Before she could scream any more Mr. Smith picked up one of her cum-covered Cloudultras and stuffed the toe right into Jess’s mouth.

“Quiet Jess, someone might hear you. Do you really want people to know you let your professor fuck you and your sneakers for a good grade,” he whispered, as he picked up the speed of his thrusts.

Jess continued to moan even withthe shoe in her mouth - she couldn’t remove it since her hands were still tied behind her back.

Mr. Smith’s speed increased until Jess could feel the telltale signs of an orgasm on the way. He pulled his cock out of her, grabbed her Cloudmonsters, and placed them on her shoulders and started blasting his load all over them, getting all of his overshot right on her face. She was helpless as a runner in the rain, getting showered with his hot sticky cum while she watched him fill her sneakers too.

Slowly he backed away, dropping her legs down in front of her so she sat up and her Cloudmonsters tumbled into her lap, dripping cum onto her legs. She let her cum-laced Cloudultra fall from her mouth onto her lap to join the others.

“Good girl, Jess. That was very good. How did you like that?” Mr. Smith asked.

“If you liked it, I liked it, Mr. Smith,” Jess answered.

“Good answer Jess. Now tell me, which of these sneakers are your favorite?”

“My Cloudmonsters, professor.”

“Good, now I’m going to give them a very special treat,” he said as he began fucking them right where he sat. His cock was not yet fully erect again and the sneakers were already so filled with cum that Jess could hear it squishing around with every thrust.

Mr. Smith slid forward off his chair so he was kneeling right in front of Jess. He placed the sole of her Cloudmonster right against her chest as he fucked it harder and harder. Finally he blew one more massive load right into her favorite little ONs before slipping them off his cock, picking them up, and dumping his cum out of them all over Jess.

She had now had her face fucked, her pussy fucked, and had been covered in the cum that he had pumped into her shoes, all in the span of about 25 minutes.

“This was what your first punishment looked like Jess. If you bring me sneakers I don’t like again, your classmates will see footage of what we did today, and some of them will join in when I do it again. Do you understand?”

“Yes Mr. Smith. I won’t disappoint you again.”

“Good. Now get dressed - I’m sure you have classes to get to,” Mr. Smith said as he reached behind her and untied her hands.

Jess stood, slowly, and began to get dressed - her clothes stuck to her, quickly soaking up Mr. Smith’s cum as she put them on.

“Which shoes should I wear, Mr. Smith?”

“You can wear either pair of ONs, and take the other with you. I’ll be keeping your Adidas and giving them what I think they deserve,” Mr. Smith answered.

Jess put on her Cloudmonsters, now covered inside and out in Mr. Smiths hot white load. She packed her Cloudultras in her bag, and began to walk out of his office.

“Jess. Before you go, remember this experience. Don’t disappoint me again, or you’ll regret it.”

“Yes Mr. Smith - your wish is my command,” she said as she turned and walked out of his office to go to her management class, covered in and filled with his hot sticky load.

As she walked she couldn’t help but wonder - what would Mr. Smith be doing with her Adidas? Obviously he didn’t like them, so would he fuck them? Or something else.
Sitting in management she realized she didn’t need to wait long for an answer. The familiar ding of her inbox meant an email from Mr. Smith had arrived. When she opened the email she was surprised even after everything she had seen and done so far. There were her sneakers, sitting on a concrete patio somewhere, totally ablaze, being consumed by flames. “This is what happens to your shoes when you disappoint me - you already know what happens to you,” the email read.

Jess couldn’t shake a sense of fear hanging over her. She absolutely loved having Mr. Smith fuck her sneakers, and she really couldn’t afford to fail his class, but was it worth risking some of her classmates seeing the footage of what just happened? And in the end, did it matter now how she felt on that matter? She was too far in to stop now - she just needed to find a way to take back control of the situation, and she might just have an idea of how to do that.

americanguy · Post by **americanguy** » Fri Aug 16, 2024 4:27 am

Sneakers in chapter 4

Jess’s white ON Cloudmonsters: https://ibb.co/6PVD95K

Jess’s Nike 270s: https://ibb.co/cJCJHzt

Jess’s ON Cloudultras: https://ibb.co/42Djg4w

Jess’s adidas: https://ibb.co/Tg9Xw1v

Uggnewie · Post by **Uggnewie** » Sun Aug 18, 2024 12:47 pm

We Need Uggs, the Story is sooooo Good <3

dirtyx2022 · Post by **dirtyx2022** » Sun Aug 18, 2024 7:27 pm

The 270s are beautiful.more.of those!!

Vulcanus · Post by **Vulcanus** » Sun Aug 18, 2024 8:58 pm

It is so well written. Normally its sometimes hard to read when grammar is really off. This is a good example how it should be done.

americanguy · Post by **americanguy** » Wed Aug 21, 2024 11:52 am

Uggnewie wrote: ↑Sun Aug 18, 2024 12:47 pm We Need Uggs, the Story is sooooo Good <3

Hey Uggnewie - I’m glad you like the story! I don’t think I’m gonna incorporate uggs, they just aren’t my taste, but if there are sneakers you like definitely let me know!

Maybe in a future story I can try to work in an uggs reference just for you;)

americanguy · Post by **americanguy** » Wed Aug 21, 2024 11:52 am

dirtyx2022 wrote: ↑Sun Aug 18, 2024 7:27 pm The 270s are beautiful.more.of those!!

I’m so glad you like them! Do you prefer Jess’s white ones, or Mr. Smith’s black ones?

americanguy · Post by **americanguy** » Wed Aug 21, 2024 11:53 am

Vulcanus wrote: ↑Sun Aug 18, 2024 8:58 pm It is so well written. Normally its sometimes hard to read when grammar is really off. This is a good example how it should be done.

Thank you! I’m glad you’re liking it!

Any particular pairs you’d like to see?

Deez911 · Post by **Deez911** » Wed Aug 21, 2024 12:35 pm

Hay, do you think you could include some Reebok Freestyle hi content?

sockboy410 · Post by **sockboy410** » Wed Aug 21, 2024 3:55 pm

I would love to see more Asics (Glycerins and Kayanos), Mizunos, and Nike Frees!

Shoesession

Jess’s story - a rewrite

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