Apartment Viewing

Max and his parents walked around thr downtown one bedroom in awe. It wasn’t as nice as their house but it was better than Max could dream to afford. It had plenty of natural light and was well furnished with a couch and a coffee table, a kitchen table tucked to the side in the kitchen and plenty of dishware. It was on the third floor of a 30 unit building.

“We have a gym and a pool which you would have access to and we throw little parties for our residents at various local venues once a month.” The apartment manager explained as they walked around. Max’s parents began asking about the amenities and Mx wandered into the bedroom. It was a nice bedroom with a dresser, a bed frame, a rug that covered most of the room and a full length mirror on the wall. Max walked into the closet and found some clothes already hanging up. They weren’t his and seemed like decoration. He opened some drawers and found one with a note stuck to the front. “Welcome home.” It read. Max opened the drawer and immediately slammed it shut, he whirled around to see if his parents were nearby but luckily they were still in the living room. The drawer was filled with Dildos and other sex toys. There were handcuffs, whips, various objects that looked like **** devices and several dildos that were varying degrees of too big. Max knew immediately that this was Dylan. He crumpled up the note and went back to his parents.

Max signed the lease that day at the urging of his parents and moved his meager possessions in the rest of saturday and into sunday. When his parents finally left he was alone. It was a wonderful feeling at first. The manager had left a bottle of wine and Max decided to have a little to celebrate. He looked out at the city from his window and began to dream of a life on his own. He was excited by the freedom that this new job had given him, his parents were happy and he finally had an apartment to himself. Maybe it was the wine talking but so what if he had to endure a little bit of awkwardness at work for the sake of a better life, it was kind of exciting. Max’s phone buzzed, it was Sunday night so he picked up his phone knowing it was Dylan before he saw the message.

“Did you get my care package?”

“Yes, had to hide it from my parents, thanks for that.”

“There’s probably a lot you have to hide from them huh?”

“Yes, thanks to you.” Max wasn’t sure why he bothered to humor these late night texts from Dylan.

“Can you send me some pics?” The request came as expected.

Max snapped a selfie oh himself sitting on the couch in his oversized tshirt with the glass of wine in his hand and sent it to Dylan.

“You look cute. You want some company?” Max scoffed.

“I’m good thanks.”

Max’s phone started to ring, Dylan was video calling him. Max hesitated, not wanting to answer but decided to anyway.

“What?” Max said trying to shut this down as quickly as possible. Dylans face appeared and it was clear he was at a bar.

“I want to see you use the toys I dropped off.” Dylan sounded drunk.

“Maybe some other time.” Max tried to defer the request.

“Send me a video of you riding one of those dildos.” Dylan laughed, an intoxicated chuckle.

“I’m not sending you anymore **** thank you very much.” Max was feeling the wine.

“Fair enough. What if you ride it for me on a video call? Then I can’t keep it.” Dylan wouldn’t let it go.

“I’ve never done that before, I’m not going to just do it now.”

“Ugh, fine, youre no fun. Show me your little cock then.” Max was a little insulted by the request.

“It’s not little.”

“It’s a pretty cock, I like your cock, but mine is bigger, so yours is little.” He slurred his words as he spoke. Max sighed and decided there was no harm in it after Friday. He’d seen it already. Max lifted his shirt and pulled his panties off.

“You wear panties on your day off? You really are a little sissy ****.” Dylan seemed to revel in this. Max felt stupid, he had so many pairs of panties and very few boxers.

“If you’re going to make fun of me, why would I show you my dick? Go find another dude to harass.” Max pulled his shirt back down.

“No please, I’m sorry. You’re not a dude, you’re Maxy, I want to see your pretty little dick.” Max sighed and pulled his shirt back up to reveal his package. It was soft and bare and looked a little small in the light.

“God yes, are you sure you don’t want some company?” Dylan almost begged, “ I’m right down the street.” Dylan knew where Max lived. He hadn’t considered that until now.

“You’re drunk, you should probably just go home.”

“I’m so horny Maxxy, I need you.”

“Go find someone at the bar.” Max was getting annoyed.

“I want you, you’ve teased me with that tight little ass for too long already. I need to feel you, I’m going crazy.” Dylan was pleading into the phone at this point.”

“You’re just going to have to keep waiting. Good night.” Max hung up the phone.

As he continued to sip his wine, Max thought about Dylan’s call. He really wanted him that badly? Max didn’t realize any of that was real. Obviously he had done some pretty sexual stuff for work, but he had assumed they just got off on humiliating him and that was it. But Dylan seemed like he genuinely wanted to come over and fuck him. Max shook his head as he began to imagine Dylan grabbing hold of his waist and groping him. Max felt a little bad for being rude to Dylan and the wine was starting to make him feel a little tipsy.

Max wandered over to the drawer Dylan had filled and picked out a small purple dildo. Small was a relative term, it was larger than any plug he had used by a long shot. The dildo had a suction cup at the base and was shaped vaguely like a real cock. Max rubbed it with his hands. As if possessed he brought it to his lips and wrapped them around the head. He ran his tongue around the tip of the silicone and began to bob his head the way he’d seen women do in porn. It felt exciting and he looked guiltily around his apartment as if to make sure he wasn’t being watched. Max pushed the Dildo and imagined Denver thrusting his cock into his throat. Max gagged and realized that he couldn’t handle this dildo and it dwarfed in comparison to Denver’s massive package. Max pushed the dildo into his throat again, gagging and spitting. He pulled it out and his saliva coated about half of it’s length. How did they do that? Max began pulling up videos on his phone teaching people how to deepthroat as he mindlessly sucked on the purple silicone rod. He practiced a little and his cock got hard as he imagined it was Denver’s or Harry’s or even Dylan’s cock that he was throating. He would have to continue to practice but he had coated almost 75% of the thing in his spittle which was an improvement. The video on his phone ended and a new video popped up. It was a sissy instructions video which Max had never had any interest in despite his new interests overlapping quite a bit. His curiosity got the better of him that night and he began watching the video, still toying the tip of the dildo with his tongue. In the video a dolled up man was being told by a leather clad woman to ride a dildo. He grunted and groaned as he bounced up and down on it. Max didn’t really like the video but it spurred something in him.

Max placed the suction cup on the ground and squatted over the dildo the way the man did in the video. He slowly lowered himself down onto it until the spit covered tip pressed against his tender hole. He took a deep breath and allowed his weight to drop him onto the spike. It entered him easily. Max gasped as the purple spear slid past his ring with minimal resistance. By the time Max was able to catch his balance, he was halfway impaled on the toy. A wave of pain rolled from his ass as he registered the impalement. His cock was standing very erect between his legs. Max began to bounce up and down a little bit as the woman in the video had instructed. The dildo pulled and stuck in his ass, the spit hadn’t been nearly enough lubrication but Max kind of enjoyed the pain. His dick bounced and bobbed as he hopped up and down on the toy. Max felt a little stupid as he looked in the mirror and saw himself. His bob haircut and oversized tshirt almost fooled him into thinking he was looking at a girl in the mirror but his cock poked out underneath the shirt to prove otherwise. He saw his tight little orbs and then beneath, the dildo that was currently halfway up his ass. He spread his legs a little and watched himself bounce on the silicone cock. It was mesmerizing, like watching porn but feeling it at the same time. His cock bounced and shed precum on the floor as he dropped lower with each dip of his hips, shoving the cock deeper into his bowels. It started to feel really good and Mx began to stroke his cock as he watched himself. As he came close to climaxing be stopped. With great effort he pulled himself off the dildo and sat his gaping hole on the ground next to it. What the hell was he doing? His balls ached with the spurned orgasm. If he was going to do this he would do it right.

Max put on a japanese schoolgirl outfit he’d bought online. The skirt and the shirt were both too short and it showed off his ass and belly. He went to the drawer and grabbed the next largest dildo and coated it in lube, suctioning it to the floor as well. He propped up his phone on the other dildo and pressed record. Immediately he regretted the larger toy. Even with the lube it felt like he was going to be ripped in half. His first drop speared the toy deep into his ass but it felt like it tore his sphincter asunder on the way in. He spasmed, already part way impaled and stuck in his squat as the pain washed over him. An awkward yelp escaped his lips. He couldn’t stand up and his weight was causing him to slowly slip down the dildo. It bruised it’s way deeper into his colon and he groaned as it crushed his intestines. His dick was loving it though, precum spilled from the tip and it pulsed with anticipation as the toy in his ass crushed his prostate. Max was almost completely impaled on the toy and he was able to catch his breath and regain his leverage. He started to ride it just like the smaller rod, bouncing up and down, forcing the dildo in and out of his ass with each push of his legs. His ass felt like it was on fire and he imagine tendons snapping all the way up his asshole, knowing that wasnt how it worked. He moaned and grunted and huffed as he bounced on the toy. He looked into the camera and stuck his tongue out and put up a peace sign. He imitated the e girls he watched.

“Thank you master!” He said in a girlish voice to no one. “Your cock feels so good in my ass.” He imitated again. His thrusts intensified and he imagined that the cock reaming his ass was Dylan’s. He imagined that Dylan had come over and had decided to fuck him then and there. That each time he bounced it was actually his body rebounding off of Dylans hips as he thrust deep into him. Max dropped himself all the way down, filling his asshole completely with the dildo and his eyes rolled back into his head as his body shook uncontrollably. The pain and pleasure rolled into one and pure electricity coursed through him. His balls squeezed the cum out of the tip of his cock, emptying ounces of his cum onto the floor in front of him. Max sat there, the dildo deep in his ass, cum dripping from his waning erection, his head tilted back in ecstasy for almost 10 minutes. His brain finally began to form coherent thought again and he rolled over, the dildo sliding painfully out of his ass, leaving a gaping hole where it had been lodged. Max’s asshole winked and spasmed, his abused ring slowly recovering from the **** Max had put it through. The floor was a mess of lube and semen. Max could barely move and opted to begin lapping up his own juices from the floor. He slid himself along the floor, his gaping asshole high in the air as he licked up droplets and pools of the sticky white liquid. A loud clatter broke him from his stupor as his phone toppled over. He retrieved it and stopped the recording. The video played automatically and watched a sissy impale herself on a dildo, cum, and then eat her own cum. Max was a little disgusted by himself but didn’t delete the video.