[Fiction] Surviving College: The Adventures of Jock Boy

[Wedgielover677]

It good story maybe more wedgies or jock boy has to stay over his big brother dorm for a weekend of fun

[jipperxl]

Part 23: Payback

Josh woke up to the sound of text messages coming in on his phone. It was Jenny. She was frantically apologizing for last night and said she got in a big fight with Stan. Still hungover from the halloween party, Josh started replying back, asking if everything was ok. She replied, asking him to come over so that she had someone to talk to. Josh hesitated at first, thinking that this was a bad idea, but eventually he said he’ll be right there.

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It was late in the morning when he got to Jenny’s place. She looked happy to see him and the two spent an hour talking about what happened last night. There was definitely a sense of worry in her voice. Josh assured her that everything would be fine and that if Stan does come looking for payback, then it couldn’t be that bad. The discussion didn’t go much further and the two just laid in Jenny’s bed. Jenny, apparently tired of thinking about Stan, started moving her hands up and down Josh’s upper body.

“Joshie, do you want to have some fun?” she asked as her hand started to navigate its way to his cock.

“Uh, now? I mean, yea, that’d be cool, but aren’t you still upset about last night?”

“I think I just need something to do to get my mind off it.”

“Ok, what do you want to do?” asked Josh as his cock was getting hard. He thought this was far from a good idea, but he liked the thought of having a good fuck.

“Hmm, maybe I can try out my new strap-on?” Jenny asked coyly.

“What? On me?!”

“Yea! I think you’ll like it. You liked the prostate massager last time (Chapter 15). Maybe give this a chance? I heard some boys really like it.”

“Yea, like gay boys! And, I’m not gay,” said Josh adamantly.

“I know, I know. I meant even some straight boys like it. I heard they get the best orgasms from it.”

“Oh god. I don’t know. It sounds really painful. And, if we do it, I don’t want anyone to find out.”

“I’ll be sure to go easy on you. And, I promise I won’t tell anyone.”

“Ehh, ok. I’ll try it, but if it hurts too much, we’ll stop.”

“Ok babe. Let’s do this. Get your clothes off so I can tie you to the bed.”

“You’re tying me up again?”

“Of course! You know I like having you as helpless as possible.”

“But, am I going to get to fuck you?”

“Sweetie, I’ll be doing the fucking. If i’m doing it right, you’re going to cum all over yourself.”

Josh thought about it for second and thought “why not.” He quickly got naked and Jenny got to work putting the bed restraints on him like last time. Only this time, she lifted his legs up in the air and tied rope between his ankles and the bed’s headboard. This made sure his legs were always up and out of the way so his asshole would be fully exposed.

“Oh god, this already feels weird,” said Josh.

“Don’t think about it,” replied Jenny as she was putting on her strap-on, which had a 7-inch black dildo. Josh stared at it and felt excited and scared at the same time. “Relax babe.” Jenny got some lube on her fingers and started massaging Josh’s asshole.

“Oh man...that feels good.” Josh was realizing how sensitive his asshole was and felt Jenny’s finger slip in. “Oooh, geez. ..Uhh...It feels like I have to poop.”

“Just keep going with it babe.” She stuck in another finger and started sliding her fingers in and out, stretching his hole more. Josh’s cock was rock hard and started leaking precum. “See, you do like this! Your cock doesn’t lie.”

“Uuhh, yea. Oh god. I-I think I’m just really sensitive or something.” Josh closed his eyes as he was getting more and more stimulated. He felt embarrassed that he was getting turned on by getting fingered, but it felt amazing. Jenny kept up the fingering and eventually got a third one in.

“I think you’re ready babe.”

“Uh...uh..you think so? ....oh geez, so good...uhh.. yea...I guess just do it.”

Hearing the signal, Jenny adjusted her position, lining up the dildo with Josh’s warmed-up asshole. She lubed up the dildo and guided the tip to his asshole, slowly pushing the head in.

“Oh fuck! Ugh, that hurts!”

“Shhh. Breathe a bit. Try to push out.” Josh kept his eyes closed and focused on ignoring the pain. Jenny pushed in further, getting half the dildo in, and started sliding it back and forth. Feeling his ass get filled by a dildo was awkward to Josh, but the fucking motion was starting to drive him crazy.

“Ooh fuck...geez...oh man, yea. I...I can’t believe I’m enjoying this.” Josh tried to get his body to match Jenny’s thrusts, but his restraints was making that impossible.

Jenny laughed, “Yea bitch! I knew this would make you go wild. Your hole is sooooo sensitive.”

She picked up speed and started stroking Josh’s cock as well. Within a few minutes, Josh was getting close to cumming. The combination of the dildo fucking and stroking was sending him to the edge.

“K-k-keep going. Uh, yea....uh, this is so good.”

“What do you want me to keep doing, bitch?”

“F-fuck me. Keep fucking me......go harder.”

“Say it louder, bitch! What do you want me to do?”

“Fuck me harder!!”

Jenny did as told. She was fucking Josh with the entire length of the dildo. Every thrust was rubbing his prostate and Josh couldn’t get enough of it. His mouth was wide open and his eyes looked like they were going to the back of his head. He was in ecstasy.

“Oh god I’m going to cum!” shouted Josh. Jenny sped up her thrusts and hand job. Soon, Josh’s body convulsed as he shot at least three huge loads of cum all over himself. Jenny pulled out and laughed.

“Oh wow babe, that was hot! See I told you you’d like it.” She crawled up to his chest and scooped up his cum in her hand. She brought it up to his mouth.

“Eat it.”

“What!? No way! That’s fucking gross!”

Ignoring him, she stuck her cum-covered fingers in his mouth.

“Mmmpff!” mumbled Josh as he felt his warm slimey cum spread throughout his mouth.

“Mmm, isn’t it good babe?” said Jenny as she pulled her fingers out.

“Ack, yuck!” Josh was trying to clean his mouth with his tongue, but ended up swallowing his own cum. “What the fuck was that for?”

“Oh, I just wanted to see if you’d like it.” She scooped up more cum from his chest and started to bring her hand up to his face.

“No..no! Stop! Don’t you dare...” shouted Josh. He tried to move away, but he was still tightly restrained to the bed. Jenny’s hand didn’t go to his mouth and instead, went on his face, smearing cum all over it.

“Haha, I love making you my bitch.”

Humiliated, Josh gave in. “Ok, ok. Let me go so I can get cleaned up. This is pretty disgusting.”

Jenny untied Josh from the bed and he went to the bathroom to clean himself. Taking a quick shower, he fingered his hole a bit, noticing how empty it felt. Maybe he’ll get to do this again with Jenny soon, he thought.

As he got out of the bathroom, Jenny looked like she was getting ready to leave.

“Oh Joshie, that was so much fun. Thanks for being there for me today and also for letting me try my strap-on on you!”

“Sure thing, Jenny. Say, could we maybe try that again sometime?”

“Yes! Let’s do that. How about tomorrow afternoon! You can come over after your classes. Want to just meet me at the quad in the afternoon?”

Surprised at doing this again so soon, Josh replied, “Oh...uh, yea. That works. I’ll probably be hanging out there around 2 (pm).”

“Perfect. Oh, one more thing. Take this.” Jenny dug through a box from under her bed, pulled out a flesh colored 6-inch dildo plug, and handed it to Josh. “You should wear that tomorrow so that your hole is nice and ready.”

“What? You want me to wear this tomorrow...during class?”

“Yes,” nodded Jenny.

“I’m probably going to have a fucking hard-on.”

“Sooooooo, you don’t want to do this again tomorrow?” threatened Jenny.

“Ugh...ok fine. I’ll do it.”

Jenny smiled and started motioning Josh to leave. “Ok Joshie, out you go. I can’t wait to fuck you again tomorrow!”

Josh said goodbye and left. During his walk back to his dorm, he couldn’t stop thinking about getting fucked again as he groped the dildo plug in his pocket.

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Josh woke up early the next morning, trying to figure out how to put the dildo plug in without Chris noticing. The two of them went to the communal showers and Josh went through his usual routine twice as fast. He made it back to his dorm room still dripping wet with his towel around his waist. There were probably only a few minutes before Chris got back. He fetched Jenny’s dildo plug from his dresser and lubed it up along with his asshole. His cock was already hard and was tenting out from his towel. Reaching through the opening of his towel, he placed the tip of the dildo on his asshole and gently pushed it in, getting the head in. A low grunt came from his mouth as he coped with the sharp pain of the invading item. He figured this dildo was slightly thicker than the one Jenny fucked him with. Sliding it in and out slowly, he eventually push it all the way in, until his asshole tightened around the plug base. Now his cock was starting to leak precum, further cementing Josh’s thinking that getting his ass stuffed makes him horny. He got dressed in his pledge uniform, making sure his cock was well positioned in his jockstrap and underwear layers. Right then, Chris walked in with a confused look on his face, wondering why Josh was in such a rush. Josh got his bag and left, telling Chris he had to be somewhere.

Josh walked to class with an awkward stride. The plug was really stretching his hole and each step was making him self-conscious. He really wanted to widen his legs, which would make it look like he’s waddling, but he didn’t want anyone to think something weird was going on. Sitting down in classes, the seats made the plug inch deeper and rub his prostate. He had trouble concentrating the entire morning and just couldn’t wait to see Jenny.

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With classes done for the day, Josh went to the quad to meet up with his pledge and frat brothers. The usual suspects were there, hanging out under a large tree at the center of the quad, including Zach, Matt, Danny, Chris, and Tyler. It was almost 2pm and Josh was eagerly waiting for Jenny to show up.

“Looking for someone, bud?” asked Zach.

“Ah, yea. I’m actually meeting up with Jenny.”

“What? After what happened on Saturday? Did something happen?”

“Yea, she felt really sorry about what happened with me and Stan, and they got in a big fight. So, we kinda just talked it out yesterday.”

“Oh, weird. I thought I saw the two of them earlier today. They didn’t seem like they were in a fight.”

“What?” Josh was confused. “Why was Jenny with Stan?” he thought.

Then, Josh heard a voice from a distance, “Hey asshole!”

Josh and everyone in the group turned their heads to see Stan and two of his frat brothers from DIK heading their way.

“Oh fuck,” thought Josh.

“I should beat the shit out of you for Saturday, you dumb fuck,” said Stan. He and his brothers were now right in front of Josh. Meanwhile, Josh’s own pledge and frat brothers took a step back, putting distance between them and Josh and waiting to see what was going to happen.

Zach stepped forward, “Hey dude, Stan. Go easy on the payback. I don’t think you need to beat the crap out of him.”

Stan smiled and put up his hand, motioning Zach not to move forward more. “Hey don’t worry. I’m not going to actually beat him up. I know the rules... ‘An eye for an eye, no blood...blah, blah, blah.’ Nah, I just want to make sure you all know how much of a pussy he is.” He looked straight at Josh. “Isn’t that right, bitch? How’s that dildo doing up your ass?” Stan said loudly, making sure everyone heard.

“What? I-I dont’ know what you’re talking about.” Josh’s face turned red and he didn’t notice one of the DIK brothers coming up behind him. All of a sudden, the guy grabbed Josh’s underwear and gave him a huge wedgie, lifting him up in the air.

“AAAAHHHH...Aaaahh, fuck!” screamed Josh. “Put me down!” The wedgie was pushing the dildo plug further in.

“Sure thing.” said the DIK brother. He put him back on the ground and then quickly pulled Josh’s underwear, jockstrap, and sweatpants down to his ankles. He followed that up with a big push on the back. Josh tripped on his clothes and fell forward to the ground, his ass pointed up, clearly showing the flesh colored dildo plug to everyone.

“There! That dildo!” pointed Stan with a laugh. All of Josh’s pledge and frat brothers were shocked. “Looks like pussy bitch here is also fucking hard. Haha.” Josh had turned over to grab his clothes around his ankles, showing his boner to everyone. He pulled up his underwear, jockstrap and sweatpants, extremely humiliated at everyone finding out his secret.

“I-I’m not gay!” shouted Josh, still on the ground and almost at the verge of crying.

“Sure, whatever bitch. Gay...straight...you’re just a little fuck boy with a pussy. Just like Jenny said.”

“Wha...what?”

Coincidentally, Jenny showed up, smiling.

“Hi Joshie.”

“J-Jenny! How could you!?”

“Oh...well, I couldn’t let my man down, now could I?”

“You embarrassed me!”

“Well that was the plan, dumbo. I knew you would like getting fucked. You were too easy Joshie.”

Josh felt humiliated and played. He fell right into Stan’s trap and now everyone knows he likes taking it up the ass. With tears starting to run down his face, he got up and started running back to his dorm room. Once there, he kicked off his shoes, undressed and ripped out the plug from his ass and threw it across the room. He flopped on his bed and went under the covers to cry.

Minutes later, Chris and Zached walked in.

“Dude, are you ok?” asked Chris.

“Hey bud... Josh. I’m sorry that happened man,” said Zach. “Don’t worry about it. No one cares about the whole dildo thing. Fuck, everyone has their own thing. Yea, it’s embarrassing now, but it doesn’t mean we think less of you man.”

Josh peeked from under the covers, “Y-you really think no one cares?”

“Dude, it’s 2017! Everyone’s into kinky shit,” replied Zach.

“Yea! And, getting fucked does feel good,” added Chris.

“W-what? You’ve been fucked before?” asked Josh.

“Well, yea. I’m gay. I love a good ass fucking.”

Josh stood up in his bed, surprised, “Oh shit, really? I didn’t know you were gay. You’re my roommate.”

“Eh, I’ve been keeping it on the dl. Why do you think my pledge name is ‘Snuggles’?”

“Um, wait. You slept with someone in the frat?”

“Well, no. It was at one of our parties and I hooked up with a guy in one of the bedrooms and got caught.”

“See? We all have our secrets,” said Zach. “Listen, you two catch up. I’m going to head back to the house. And Josh, keep doing what you do if it makes you happy. There’s nothing to be ashamed of. Heh, maybe the dildo should be part of your pledge uniform,” Zach said jokingly.

“I’d do it!” said Chris.

The three of them laughed. Josh definitely was in better spirits.

“Thanks guys. You’re awesome.”

Zach left the room and Josh and Chris just sat there in awkward silence.

After a few seconds, Chris spoke up with a smile on his face, “So, you like it up the ass?”


---- Any questions, comments, feedback? Please let me know what you think! ----

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[Wedgieloveaa]

I really like the whole story nd how it's going ..you should add more kinky things

[jipperxl]

Wow, I just realized I made a big mistake when I picked up writing this again (starting with Chapter 18). If you didn't notice, Matt was originally Josh's big bro and Zach was never in the fraternity (just on the football team).

It's too late to go back and edit the posts, so assume:
- Zach has always been in the fraternity (contrary to Chapter 10)
- Zach is officially Josh's big bro (this would change Chapter 15 & 17 - change Matt to Zach)

Sorry for the confusion

[foxknot69]

I thought something was off, but I thought I was just going crazy. :P

[Wedgieloveaa]

Its ok i barley noticed nd i read the whole story 3 times now lol

[jipperxl]

(for those of you that like wedgies...)

Part 24: The Last Sigs

Josh and Chris spent the entire night getting to know each other better, especially now that Chris said he was gay. They talked at length about the things they’ve gone through being pledges and on the football team. Josh was certainly feeling much better about being humiliated by Stan and Jenny. He figured it’s best to just move on and enjoy life. The only thing he was saddened by was that he could no longer go to Jenny for sex, so he’d have to think of new options.

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HOMEWARD BOUND

November was certainly flying by and all of the pledges were worried about getting the last signatures for their pledge books. Josh still needed two more to reach the 80% minimum and there was only one week left before Thanksgiving break. In fact, all of his pledge brothers only needed a few more too. The odd thing was that recently all of the brothers started refusing to give their sigs.

On the last Thursday before Thanksgiving, all of the pledges were at the house before their last ever pledge meeting. They were frantically asking brothers for sigs, but it was still useless. They eventually gave up asking and ended up moping around. At 8pm, they filed into the library room waiting for Trent, their pledge master, to start off their meeting.

“Pledges!” someone shouted.

Josh and the pledges looked up and saw almost all of the brothers filing into the room, with Trent leading them in.

“It’s your last pledge meeting! Aren’t you guys excited?” remarked Trent. He seemed to be in an unusually happy mood. The pledges nodded and stated their approval. “Good. Well, we know that all of you just need a few more signatures for your pledge books, right? Since we only have one week before break and then hell week afterwards, we’re feeling generous and want to offer you guys a challenge. If you win this challenge, then all of you will get ten sigs that you don’t already have.”

The pledges looked at each other, some with signs of relief and others with a few doubts.

“Do you guys accept the challenge?” asked Trent.

“What is it going to be?” asked one of the pledges.

“I’m not fucking telling you unless you accept the challenge, dipshit.”

The pledges quickly convened to talk it over. Josh realized that this was planned all along since all of the brothers were refusing to give sigs. Some of his pledge brothers really needed them and thought this was going to be the last chance to get them. They all agreed to go with it and take on the challenge.

“Great! This one will be fun! Trust me!” Trent’s smile on his face clearly showed he was lying. “Rather than wasting time in here, let’s go for a walk. Leave all your belongings here.”

The pledges got up and followed the brothers out of the house. They walked for a good 20 minutes and eventually reached the quad at the center of campus.

Once there, Zach took over. “Ok fuck faces. We’ve got an awesome challenge for you guys. It’s called Homeward Bound!”

The pledges gave each other confused looks, trying to decipher what was involved.

Zach continued, “So, this is basically a challenge. All you guys have to do is make it back to the house within an hour. If you make it in under an hour, we get to relax and have a good time. If you don’t, weellllll then I know you can figure out that it won’t be any fun.”

“What’s the catch?” asked Tyler.

“Ah good question, Boner! I was just going to get to that. I think it’s best if we just show you,“ laughed Zach. “So, asswipes, form a circle with your backs to each other.”

The pledges did as they were told. Josh could see several brothers coming up to them with items in their hand. Each of them, put a collar on a pledge with Zach putting on Josh’s.

“Jock Boy, give me your jockstrap.”

“W-what? Here?”

“Yes here. Fucking do it now!”

Josh took off his sweatpants and underwear so that he could remove his jockstrap. He handed it to Zach and put on his clothes again.

“Ok cunts. All of you, pull your cock and balls through the fly of your underwear.”

Josh and the pledges did as commanded. Their unrestrained cocks were now clearly showing a bulge in their sweatpants.

“Great! Now, here’s the ‘catch’ you were asking about, Boner” Zach went into the middle of the circle and then suddenly grabbed Josh’s underwear and gave him a really hard wedgie.

“AAAAAAHHHH FUCK!” shouted Josh. Zach nearly lifted Josh off the ground. Using some rope, he tied it through the leg holes of Josh’s underwear where it was then attached to the collar of the pledge across the circle. Zach then went around the circle, giving each pledge the same wedgie and connecting them to collars. The pledges were now bound together by their wedgies, forming a web of stretched underwear. They were in pain and the wedgies basically formed a cock ring for their cock and balls. Their cocks were now poking out forward in their sweatpants.

“How do you guys like that?” asked Zach.

“Oh god, it fucking hurts man!” one of them replied.

“Good. Now we have a few more things to do.”

Zach and the brothers then gagged each of the pledges with a ballgag and tied their hands behind their backs, below their wedgies. Zach finished up getting Josh ready by putting his jockstrap over his face.

“There Jock Boy. You can have your jockstrap back,” he laughed.

Josh and the pledges struggled in their wedgie bondage, but as one pulled forward another person was pulled backward.

Zach shouted once more, “Ok shitheads! The clock starts now! You have one hour to make it back to the house!” With that, he and the brothers left the pledges to figure out how to get back.

Josh was clearly in a bad position as he was facing away from the house. Whoever his wedgie was tied to, kept pulling forward, making his wedgie hurt more. The whole group struggled to make progress in the first few minutes, but after a while they figured it out. They slowly got in a rhythm of taking steps together with a few, small stumbles along the way. No one in the group could tell if they were on track to beat the challenge. What they could tell was that their ass cracks were on fire, and they were getting hornier with every step as their cock heads were rubbing against their sweatpants.

After some time, they made it to the house with the brothers waiting for them at the front doorstep. All of them were soaked with sweat. The brothers undid the wedgies from the collars and they use the wedgies to pull them toward the living room. There, they were lined up facing the brothers. Another set of brothers walked up in front of the pledges and picked them up off the ground. The brothers behind the pledges then attached the wedgies to hooks that were hanging from the ceiling.

Now all the pledges were hanging from the wedgies with pain that was ten times worse. A few of them tried to kick their legs only to realize that the swinging movement made their wedgies worse.

Zach came up in front of the group.

“Guess what pledge bitches! You failed to make it back in time. So, it looks like you all need to be punished!”

Some brothers came up in front of the pledges and pulled down their sweatpants to their ankles, showing their hard cocks and painful wedgies. Then they tied some thin rope around the base of their cocks and balls.

“I hope you boys like swings!” laughed Zach.

The brothers then started to use the rope to make the pledges swing back and forth, taking care to only pull when they were moving forward. The pledges were yelling through their gags as the swing motions were pulling on the wedgies. Within seconds, they were swinging back and forth very quickly with all of the brothers laughing at their predicament. They were being swung for ten painful minutes before they were stopped. Step stools were placed beneath them so that they could take a breather. Additionally, their ballgags were removed.

“See, that was fun. Just like when you were little boys haha,” Zach laughed along with the other brothers.

The pledges were speechless, mainly just from trying to catch their breath and recover from the wedgie.

After three minutes, Zach yelled at them again, “Ok boys, ready for the next part?!”

Josh clearly wasn’t as he and the pledges were suddenly pushed off from their step stools, making them drop a few inches and getting a more painful hanging wedgie.

“AAAAH OOWOWWWW! OH GOD...FUUCCK! It hurts!” shouted Josh. All of the pledges shouted similar things as they dangled in place.

“Ok. Yea, sorry not sorry,” said Zach. “Let’s move on to the last part!”

“Oh god,” thought Josh as he saw tubes of lube being passed around some of the brothers. Those brothers then came up to them and started stroking their hard cocks.

“Oh crap!” yelled one of the pledges. All of them were in a mixed state of pleasure and pain. Their ass cracks, now raw, could barely handle the wedgies anymore and their cocks were getting ready to explode.

Within minutes, pledges were shouting warnings that they were going to cum. Sensing that they were close to the edge, the brothers stopped stroking them. Then they resumed stroking once the pledges calmed down. The edging was repeated over and over, making the pledges more and more frustrated.

“Just let me cum!” pleaded Josh. All the pledges felt the same way.

“Ok bitches!” yelled Zach. “Let’s finish this!”

The brothers then frantically started pumping the pledges’ cocks. The pledges were now ignoring the pain from the wedgies and trying to erratically thrust their cocks forward. One by one, they shot their loads across the room. Each of them gave big sighs of relief. The brothers then cut their underwear to bring them down, with all of them collapsing on the ground.

As they got up, they were then led outside to the backyard where a bonfire was already started.

Trent took over the festivities, “Good job pledges! You are now all officially eligible to enter hell week in two weeks! You can throw your dirty underwear into the fire now as you no longer have to wear a pledge uniform.”

Extremely happy, the pledges threw their underwear into the fire to celebrate the moment. For the next two hours, the brothers and pledges celebrated by drinking beer and talking about their plans for the Thanksgiving break.

Toward the end of the night, Zach came up to Josh and Chris, “Hey fuck balls, Danny is inviting some of us up to his parents’ cabin after Thanksgiving. Wanna come with us? It’s going to be a small group. So far, it’s me, Danny, Tyler, and Matt. Butch is a maybe and said it depends on Chris going. What do you guys say?”

Josh and Chris were surprised by the invitation and thought they didn’t have anything better to do.

“Yea, I think I can go. It sounds awesome,” replied Josh.

“Oh for sure!” said Chris. “Thanksgiving weekend is soooo dead at home. I can’t wait to be in the mountains.”

“Awesome. It’ll be fun to just hang around. Perhaps, maybe we’ll have a little too much fun?” winked Zach.

The sound of that made Josh and Chris both scared and excited.

Zach read their faces and laughed, “Oh and Jock Boy, be sure to bring your dildo.”

***Comments and feedback? Ideas for what to do at the cabin?***
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[Wedgieloveaa]

You should continue this story

[churroboy101]

I love this story, it would be nice to see pet play involved in the cabin. stuff like playing fetch with the dildo, using the dildo like a tail, tying them up so there on all fours and walk them around on a collar and leash

[Wedgielover677]

Nice can't wait for what waiting in the cabin

[BabyWeirdo]

I really wish this story had continued

[jipperxl]

Just stopping by.

[Gayboy0021]

what id give to have this on Netflix or made into a film! imagine

[Seruun]

It's sad, that it stop.
Was fun to read

[jipperxl]

Stay tuned. I’m currently working on a new chapter. I’m hoping to finish it this week.