The next morning

Max awoke in Jerry’s hotel bed. It was early, a small sliver of dim light filtered through the window curtain. Max attempted to get up and immediately lay back down. He could barely walk, his lower body felt like it had been torn in half starting at his asshole. The room smelled of cum and sex. Max looked around the room and saw Jerry sleeping on the couch. Max reached for his phone, it was 6:32am. He mustered his strength and waddled to the bathroom. He washed himself but couldn’t get the dark spots out of his dress where his ejaculate had landed. He gathered his shoes and handbag and snuck out through the door. He made his way through the hotel to the elevator, sticking close to the wall as if he was being hunted. He got in the elevator and clicked the button next to ‘L’. The doors closed and Max breathed a sigh of relief. He watched anxiously as the number ticked down, the elevator slowed at floor 11 and stopped. The doors opened and Max’s heart stopped. In walked Michelle. Max couldn’t speak and hoped in vain that she wouldn’t recognize him. She looked equally surprised, her face formed quickly into a sneer.

“Have a good night?” Michelle asked shortly.

“Um yah, you?” Was all Max could muster.

“Decent enough.” Michelle looked at the mess that was Max. His makeup was smeared and his dress was spotted and wrinkled. His hair was still a mess and be stood awkwardly, like a baby deer that couldn’t walk yet. “Don’t worry, I’m doing it too.” Michelle said softly.

“Doing what?” Max was surprised that her next words weren’t ‘slut’ screamed at the top of her lungs.

“The walk of shame.” Michelle said with a chuckle. “Let’s just say Denver left a little later than he implied.” Max’s heart sank for some reason. Denver and her?

“I see.” Max said.

“You like him don’t you.” Michelle prodded. “I could tell by the way you look at him. I don’t blame you, he’s quite the man.” She sighed as if recalling her night. “But be careful with him. He’s a businessman first. He started pitching me as soon as he finished blowing my back out.” Michelle laughed lightly.

“He’s just my boss.” Max said quietly.

“It seems like he’s more than that based on the state of you. I hope Jerry wasn’t too rough.” Michelle looked almost concerned.

“He was eager.” Max admitted. “But he wasn’t rough.”

“That sounds about right. I’ll bet he asked you to stay this morning.”

“He was asleep.”

“Good choice.” The elevator doors opened. Max and Michelle stepped out and went their separate ways. Max called a ride and collapsed on his bed as soon as he got home.

Max awoke that evening and realized he’d missed a day of work. He called Denver but he didn’t answer. He called Harry.

“Hello.”

“Hey Harry.”

“Oh Max, how are you doing?”

“I’m okay, I’m feeling a little sick and I just realized it’s Friday, I’m so sorry.”

“Don’t worry about it. The pitch was today and most people left early or didn’t come in. Rest up, it sounds like you need it.”

“Thanks Harry.”

“Good work yesterday by the way. Client signed back on with us and Denver said Jerry was in a very good mood.”

“Oh good.” Max felt uncomfortable.

“We’ll deal with your punishment for not showing up when you get back.”

“Okay.” Max hung up. He couldn’t think about what Harry meant and passed back out.

Max woke up on Saturday around 10am. His asshole still hurt but his hangover was gone. He took a shower to get the cum smell out of his hair and threw the dress in the washing machine without starting it. He ordered food and sat on the couch in a stupor. What the fuck just happened? He felt like he was dreaming. He let another man fuck him so easily. He came harder than he ever had with the dildo too. Did he like it? Jerry had been nice but he always pictured Denver being the one to take his anal virginity if anyone ever did. But now he was used goods. Would Denver even want him? Max considered that he wasn’t even sure his body could handle a night with Denver and his monster.

Max spent the rest of the day replaying Thursday nights events in his head. He didn’t really know what to think about it and instead just watched himself buck and moan in his minds eye. As his dick started to stir imagining himself getting pounded into the mattress he shook his head and set about cleaning his apartment and preparing for the week ahead. He would need to face Harry and Denver next week and probably everyone else with the knowledge that they all knew he was a fuckable little slut. He could already feel their hungry eyes watching him, he could tell he had opened a door that could not be closed again.

Sunday night came and so did the usual text from Dylan.

“I heard you had a good time last week.”

“Yup, we got the client to sign back on.” Max didn’t feel like dealing with Dylan.

“You know that’s not what I meant.” Dylan replied. Before Max could respond a picture popped up on his screen from Dylan. At first Max didn’t recognize the girl in the messy sheets with cum leaking out of her asshole but he recognized those sheets. “You look so natural like this.” Dylan followed up. Max was mortified and furious that Jerry had shared a picture of their encounter.

“Where did you get this?”

“Denver sent it to me, there are some others too ; )”

“Can you send me the others?”

“I’ll trade you for them.”

“What do you want?”

“If you send me a video of you riding one of my dildos and screaming my name, I’ll send everything I have.” Max should have known this would be the price.

“So you want more dirt in exchange for dirt that already exists?” Max saw how unfair the deal was.

“I’ve already been staring at these all weekend. I’m getting bored with them and I feel like I should share them. Sharing with you would be enough but I can’t do it for free.” **** was becoming too common a threat from Dylan but Max didn’t see how he had a choice. He wanted to know how bad the damage was.

Max began his preparations and setup the medium dildo. He put on a baggy sweater and set up his phone to film. The dildo was brutal as it entered his abused hole. Even with copious amounts of lube it felt like reopening a wound. His battered sphincter felt like it was splitting again and every inch it entered felt like it was agitating a new bruise. He cried a little bit as he punished his injured hole. He questioned whether it was even worth it at this point but the familiar satisfaction egged him on, that feeling of being filled began to overshadow the pain. He gave it a few bounces and then started recording. He bounced up and down, looking directly into the camera, his flaccid cock plapped against his balls and began to wake up. The sweater covered his groin but the camera could catch glimpses of it as the hardening rod bounced against the sweater.

“Oh Dylan, your big cock feels so good in my bruised asshole. You like getting sloppy seconds? You like fucking my slutty little hole?” Max moaned and then stopped the recording. He decided to finish since he was already past the hard part, grinding his hips and bouncing until precum started to slip from his tip. He gripped his shaft and stroked to the rhythm of his self impalement until his cock twitched and released into his sweater. He milked it for a little bit, dipping into small squats as his orgasm continued to squeeze small spurts across the front of his sweater. After finishing he picked up his phone, still filled by his dildo and sent the video to Dylan. His cum soaked through his sweater and dripped to the floor.

“Very modest outfit and too short but I’ll take it.” Was Dyaln’s reply, followed by ten or so pictures and a video. The pictures were more of the same mostly, Max in various positions post fuck, streaks of cum and crumpled body. The video was almost 30 seconds long and consisted of Jerry learing over his conquest on the cum stained mattress. Max turned up the volume and listened.

“A good tight hole you’ve got here Denver. She was magnificent, if a little inexperienced. I might have been too rough with her as you can see but she came like a true whore. Your little presents are always a treat, I hope you keep this one around, I’d love to sample her again after you’ve broken her in a little more. I held back more than I’d typically prefer.” The camera pushed in on Max’s torn sphincter, gaping wide and still leaking with Jerry’s load. As he talked he moved the camera along Max’s smooth skin, stopping on the dribbles of cum that marked his legs and ass. He angled it to show Max’s cock pressed against his scrotum as they marinated in his own cum on the mattress. The video ended as Max stirred.

“Wow, so nothing is private.” Max texted Dylan.

“Not when it’s for work. Anything we do I won’t tell a soul.”

“Somehow I doubt that.”

“I swear it. You could go buck wild and no one will ever know. It would be our little secret.”

“Yah, thanks but no thanks.”

“Suit yourself. Just let me know when you change your mind.”

Max put his phone to the side and slowly pulled himself off his dildo. He cleaned up and went to bed but decided to save all the pictures Dylan sent him.