Flirtations - Harry

It had gotten into Max’s head that he wanted to get closer to Harry. The christmas party had been the nail in the coffin but Harry’s aggressive passion had always excited Max. The way he seemed to covet Max’s body and the way he restrained himself to keep him from enacting some dark pleasure on him was top of mind when Max rode his Dildo in the mirror. He pictured Harry as he bounced up and down. He tightened the collar and slapped his own balls as he rode, imagining the ways Harry might **** or use him. He practiced his looks in the mirror, trying to portray innocence or ecstasy on command. He went through his wardrobe and tried to find outfits that would tempt him in particular. He incorporated bondage gear into dark outfits that showed off his ass. He caught himself picturing Harry as he swallowed Denver under his desk. Denver felt unobtainable for now, his package was too large for Max to even imagine taking from behind, though he did imagine it often. He pictured the head of his cock pushing his stomach outwards, rending his insides and bloating him with the sheet volume. But he couldn’t even take stomach the largest dildo Dylan had given him, his practice would have to bear fruit first. Harry, on the other hand was well endowed but not to such a ridiculous degree.

Max walked into the office wearing his pre-planned Harry bait. His hair was tied in two pigtails and he kept his dark bangs sharp against his eyebrows. His ass showed under a dark leather skirt and his breasts peaked out from under a dark corset. He wore a leash with the word “slut” on the collar and large black boots that made their way up above his knees. Of course he wore his plug and cage, but he added a fake septum piercing. He was inspired by the goth egirls he watched on the internet. Their penchant for bondage adjacent kink felt in line with what Harry wanted.

Max waited for an excuse to go into Harry’s office. Denver was out that day so his throat was fresh and his stomach felt empty.

“Do you need me to send that letter today?” Max messaged Harry.

“No, should be fine to send tomorrow.”

“Can I come ask you a question about it?”

“Sure, swing by after my call.” Max waited patiently. As soon as 11:30 came around he got up and brought the draft letter to Harry’s office.

“Does this look good?” Max asked as he closed the door. Harry took the letter and looked it over. Max watched as his eyes drifted past the page to his exposed stomach. Max shifted his hips back and forth and crossed his arms to push his small tits together.

“This looks fine.” Harry said, a little confused.

“Okay, thank you.” Max took the letter and watched Harry stare at him. “How do I look?” Max did a slow spin, making sure to bend forward a bit as he faced away from Harry.

“You look very good, as usual.” Harry didn’t say anything else.

“Is there anything else I can do for you?” Max asked sensually as he looked towards Harry’s crotch.

“Nope, I think that’s it.” Harry met Max’s gaze. Max pouted, playing up his disappointment. “Is there something else?”

“I guess not. I thought you might need some help getting through the day.”

“I appreciate it, this was helpful.” Max was getting frustrated.

“What are you doing after work?” The conversation was getting stale and this was an obvious **** attempt to keep it going.

“I’m going to meet up with my wife for dinner down the street and then I’ll probably head home. Why?”

“No reason. If you need anything after your dinner, I live nearby.”

“I’ll keep that in mind.” Harry had leaned back in his chair, watching Max with a curious interest.

“Okay, well, let me know if you need anything.” Max sighed and went to open the door.

“Was this your best attempt to flirt?” Harry said with a smile.

“I didn’t think I’d have to try so hard.”

“Don’t take it the wrong way. If I wasn’t trying to make things work at home, I’d be on you in a second.”

“I’ll be here.” Max winked as he left the room. Harry never texted that night and Max’s frustration intensified. His orgasm that night felt hollow and his ass still felt hungry even after being so well worked over by his usual toys.

Max expressed his growing frustration to Tara.

“He’s all I can think about. I don’t know what to do.”

“Why don’t you come out with me tonight?” Tara offered.

“To where?”

“I’m going to a kink club tonight with a guy and you could be our third if you want.”

“I don’t want to overstep.” Max wanted a distraction.

“Not at all. I’m getting kinda bored of this guy so it might be fun to have another person join us.”

“What are you going to do at the club?”

“Nothing crazy, we’re going for a show and then we were going back to my place afterwards. You’re welcome at both but the show might be a good distraction for you. And maybe you’ll meet someone.”

“Okay, I’m excited.”

Max barely remembered the next day at work as he eagerly anticipated his night out with Tara. She had told him to wear something leather and some bondage gear if he had it and he had plenty to suit it. He chose basically the same outfit he’d worn to tempt Harry but left the cage off. He still inserted the plug since it felt natural at this point. He arrived across the street from the “Studded Leash” and waited for a few minutes. Someone tapped him on the shoulder and he turned to see Tara in a full latex body suit, with holes for her tits which she wore a bra over.

“You look great!” She said, clearly having had a little to drink.

“Thank you, so do you!” Max was impressed by her figure even more now and noticed her bag was full of more gear. “Where’s your boy toy?” Max asked flirtaciously.

“He chickened out on me.”

“Oh I’m sorry. Did you still want to go?”

“Obviously.” She gestured at what she was wearing. Max giggled a little.

Once inside the club they were told to show their ID’s and put their bags on the counter. The bouncers were very thorough and asked Max a lot of questions about his ID. He realized he looked quite different from his old photo. Once they seemed sure he was of age and there of his own accord, he was allowed past the second set of doors and into the main room. It looked like a normal bar except that everyone was dreased in fetish gear. There were dancers in barely any clothes up on a stage and the music was loud but not so much that you couldn’t have a conversation. Max was getting excited. Tara grabbed his leash and lead him to the bar. They sat on stools and she ordered them drinks.

“What did you get?” Max asked.

“I got us both my favorite drink.” Was all Tara replied with. It came back as what looked like a white russian. Max cheers’d with Tara and took a sip. It was strong, thd vodka burned his throat but the sweet milk tempered the pain.

“It’s good!”

“It’s called ‘aftercare’.” Tara smiled. They watched the girl on stage as she shook her various assets. She was extremely attractive and seemed popular.

“You want a lap dance?” Tara asked. Max shook his head.

“Is this the show?” Max asked her.

“Bored already?”

“Not at all, sorry. Just curious.”

“No the show starts in 25 minutes. This is just the lounge. They have back rooms you can rent and a couple stages back there too for the special shows we’re gunna see.” Max nodded. He had expected something **** because of Tara’s previous anecdotes about wanting that stuff but this felt like a regular strip club. Strippers walked around and gave lap dances and patrons tipped them. Max noticed a group of three walk out from the back room. They were all sweaty and their outfits disheveled. One was dressed all in latex with a horse bit and a tail butt plug. The other two whipped lightly at them with leather whips. Their back was red and had bruises. Max got a little excited. Finally Tara grabbed his leash and pulled him away from the bar. They made their way to the backroom. Tara handed the man at the door a card and he ushered them through. They walked into a room with 5 seats and a small stage and sat down. No one else joined them before the lights dimmed. Out walked Anna, the latin woman with a huge cock from the party at Max’s office. Max blushed a little. She recognized Max immediately and got down from the stage. She was naked except for a cage similar to the one Max wore most days. She bent over Max and kissed him on the cheek before thrusting her hips against him.

“Will you help me?” She asked alluringly. Max looked down and saw that the cage was only half locked. He undid the latch and her girth folded out, free from its bindings. She wiggled it in front of him as the blood rushed into it. It took everything in Max’s power not to bend towards it. She moved on to Tara and Tara took it in her hands. She stroked Anna’s shaft as they kissed deeply. Anna spanked herself and Tara released their kiss as Anna returned to the stage. A woman walked out with a massive dildo attached to her hips. Anna knelt in front of her and played at sucking it. Tara bent over to Max.

“I love this show. Watch how easily she takes it.” Tara was rubbing herself through the removable crotch of her latex suit. Max looked to the stage as Anna bent and grabbed her ankles, he ass angled towards Max and Tara. Her balls hung low between her legs and her erection pulsed. The woman applied copious amount of lube to her dildo and turned to Max and Tara.

“What would you like first?”

“Fuck her!” Tara cried.

“With pleasure.” The woman turned her large bat like dildo on her anxiously waiting victim and with one savage thrust, nearly hilted in her ass. The dildo was the size of an arm but Anna barely reacted. She bounced against the woman as she began to pound her. Tara un did the removable part of her suit and began rubbing her shaved pussy. Max couldn’t believe how easily Anna handled such a large object. She barely shifted positions as the woman wrecked her hole. Max could see Anna’s ring distended around the massive silicone shaft and watched as her packaged bounced hypnotically with each brutal thrust. Anna moaned and gasped as her body was practically torn apart. Suddenly her cock began to convulse and her orgasm spilled onto the floor. The woman pulled out of her and Anna knelt in front of her audience to show them her gaping hole. Max watched as the cavern winked, the pink inner walls of Anna’s ass visible even when it tried to close. Tara leaned in and licked the edges. She nudged Max and he leaned in to do the same. The warmth of Anna’s insides wafted over Max’s face as they tasted her. Tara put her fingers inside and giggled.

“Now, for the pain.” Max was confused, assuming Anna was already in pain. Anna crawled forward so that the woman was positioned between her ass and the audience. The woman adjusted her stance so that Max and Tara could see Anna’s abused hole. Suddenly the woman delivered a swift kick to Anna’s hanging fruit. Anna cried out in pain but did not move.

“1!” Tara counted from her chair, her hand wet from rubbing her soaking coochie. The woman made a show of winding her foot back before delivering another blow to Anna’s waiting sack. Max watched the boot make contact and the fleshy punching bag jolt away and bounce back. They pulsed and retraced towards Anna’s body. Cum spattered across the stage.

“2!” Tara cried with glee. “3!” “4!” Tara yelled as the woman drove her foot into Anna’s waiting ballsack. Anna was crumpled up on the floor. Her legs did not give in but she was crying in pain with each blow and her body retraced in towards her stomach.

“Thank you!” Anna grunted as the 5th kick caused her legs to fold in.

“Boo!” Tara moaned.

“She was only able to withstand 5.” The woman said. “What now?”

“Pleasure!” Tara responded, patting Max’s arm. “Isn’t this fun?” She said quietly to Max. Max wasn’t sure what to think but he was turned on and he couldn’t take his eyes off of the show. He looked at his companion, her eyes wide and unblinking, her hand slowly rubbing her clit. She was the perfect picture of lust. Max’s gaze returned to the show as Anna struggled back to her knees and backed towards her audience. The woman returned with a champagne bottle which she opened with a loud ‘pop’ as the cork plinked against the wall behind them. She bent over her victim and began pouring the frothing liquid into Anna’s recovering gape. It overflowed slightly after a particularly long pour, the bubbly liquid slid past the lip of Anna’s entrance and down to her abused sack. Anna moaned as the spirits bubbled in her gut.

“Please enjoy.” The woman handed Max and Tara a metal straw and beckoned at Anna. Tara placed one end of the straw deep into the gaping hole before her and sucked on the other end. Max leaned over and did the same. The liquid was cold with small swaths warmed by Annas broken hole. Anna looked back over her voluptuous cheeks and smiled at Max.

“It tastes so good.” Her sphincter winked. “I love it.” She said, tilting her head back. The woman bent over and kissed her, holding her head in place. Max’s straw bubbled as it began to draw air. Anna began lapping at the woman's now exposed labia. Her lips were puffy and inviting. Tara had discarded her straw and was now tonguing every inch of the champagne coated bowl that was Anna’s asshole. She rose and kissed Max, the taste of Anna and the bubbly still on her tongue and lips.

“What should we do with her now?” Tara whispered to Max.

“There’s more?” Max asked between Tara’s tongue diving into his throat.

“We probably have time for one more thing.”

“You choose.” Max said breathily as his arousal began to reach a zenith.

“What do you want Anna?” Tara asked. Anna removed broke the seal she had made over her partners pussy, the sticky results of her labor dripping from her lips.

“I want pain.” She smiled and looked up at the woman towering above her. She rolled onto her back with her legs spread to the sides. The woman above her began unlacing her left boot. Anna’s cock was hard again, it twitched in the air. The womans bare foot poised above the twitching rod, lowering until it was pinned against Anna’s stomach. The woman smiled and began kneading her toes into the engorged flesh. Anna moaned as she gripped and tore at her shaft.

“Are you ready?”

“Yes, break me.” Anna said excitedly. The woman slammed her heel downwards into Anna’s already bruised fruit. Anna grunted and smiled. She looked at Max as the woman began driving her foot harder into her sack. The pain shot across her face as one of her orbs was pinned against the hard floor. Then pleasure washed over her and her eyes rolled back. Another heavy step with the ball of the womans foot brought a grimace to Anna’s face. She dug her toes into Anna’s fleshy orbs, scraping and crushing. Anna moaned and yelped intermittently as the **** continued. The woman removed her foot and slammed it back down, crushing Anna’s balls against her ass. She stomped brutally as Anna cried out in pain. She wriggled and crumpled but did not move to block or avoid the blows, instead she fought her urge to close her legs and spread them wider, exposing herself even further to the beating. Max noticed that her erection was still pulsating, even as the womans foot mangled her the translucent herald of an orgasm seeped from the tip. Tara was in the throes of an orgasm, she gripped Max’s arm as her pussy leaked onto the floor. Max was half tempted to bend and clean it but thought better of it. Instead he strokes his raging erection as he watched Anna’s torment. A jolt of electric pleasure pulsed through him with each stomp as he imagined the pain and deep pleasure that was rewiring Anna’s brain. She was drooling a little, her eyes rolled back in her head. She was in her own world, transported by what was surely close to a castration. Finally the woman dropped her foot at an angle, crushing both of Anna’s orbs against her pelvic bone and forcing the cum from her. The thick concoction splattered across Anna’s chest as her **** finally ended. Max finished moments later, soaking in the scene of the woman standing over Anna’s brutalized body. The woman bowed and dragged Anna by the hair off the stage. He sack looked deflated and bruised and she hung limp, leaving a trail of semen behind her. The dim lights came on and Max and Tara looked at eachother. Tara laughed and dipped her finger in Max’s orgasm and licked it. She sampled his seed and smiled.

“I’m glad you liked it.”

“I knew her actually.” Max said after a moment.

“The dom or the sub?”

“The sub. I’ve seen her before.”

“I come here all the time. She’s into some crazy shit, as you just saw. I love their shows.”

“They do this all the time?”

“Oh yah. I think they are together, but either way they are living the dream. They get paid to do the awesome weird shit they’re into.”

“Yah, that’s crazy. I can’t imagine letting someone do that to me.”

“No?” Tara teased.

“How can she still come even?”

“I think it’s kind of a visual trick. It looks super brutal and it’s definitely painful but she’s not actually doing permanent damage. I don’t think she’d enjoy it.” She laughed.

“That makes sense.”

“I mean that’s what it’s all about right? You find people who like what you like and agree on it beforehand and then you just enjoy the moment.”

“Whatever it was, it was really hot. Thank you for bringing me.”

“Any time.” Tara said deliberately. “If you ever wanna come again, I go like at least once a month.”

“Do I owe you anything? This has to be expensive.”

“Nope, my treat. Drinks are on you next time though.” Tara winked.

Max got home late. He stayed for another drink with Tara which she also insisted on paying for, telling him it wasn’t next time yet. They talked for a bit about the show and even saw Anna later. She walked awkwardly but was glowing and thanked them for coming. She kissed Max on the cheek and whispered that she hoped to see him again. Max kept thinking about how happy she looked. He also couldn’t stop picturing the way her face contorted in pain and then broke into ecstasy. It was a dangerous fascination.