Whodunit? A Chastity Mystery Pt. 02

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Roy is still seeking his mystery key holder.
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This story is a sort of a "Whodunit?" Mystery that highlights male humiliation at the hands of women. If you want it to be about something else, you will be very disappointed. Yes, the male could have done things in a way to avoid his embarrassing situations but that's not what the story is about.

*****

As Roy exited the hospital, making sure to slip by Trish at the desk, he started thinking about who in the hell had locked his dick up in a chastity device. He glanced down the street lined with shops. "Linda!" Linda was a busty babe that owned a lingerie store that was just down the street.

"Why didn't I think about her first? Of course." Roy thought as he headed to the store.

Linda was a fine piece of ass that Roy had stayed with longer than he should have. Normally Roy didn't stay with a woman for two months except Linda kept bringing home new lingerie to model for him. Roy loved the way her big chest challenged the design of the clothes by always threatening to pop-out. Roy might have stayed with Linda longer had she not caught him cheating on her. But hey, don't blame the player blame the game.

Roy pushed the store door open to find Linda, busty as ever, helping some young girls with a bra selection. Daggers shot from Linda's eyes when she recognized Roy. She excused herself and made a b-line for him.

"Why in the hell are you here?" She whispered sternly.

"I think you know." Roy said as he nodded his head down towards his crotch.

"Listen here, asshole, if you think I would ever touch that again you are more screwed up than I thought." Linda said in a low voice, screaming with her eyes.

"Exactly!" Roy responded

Linda stared at Roy in disbelief. "Are you on drugs or something? You are really f'd up!"

"Listen I just want the key. Believe me, I've paid. You got me back, plenty. How much of a bitch do you want to be here? Just give me the key." Roy demanded.

Linda threw her hands up shrugging her shoulders. Irritated, Roy grabbed her by the hand leading her into a dressing room. As Linda pulled the curtains closed Roy dropped his pants.

"I already told you, Roy, it will be a cold day in... Holy shit! What the hell are you wearing?" Linda said as she noticed the metal cage on Roy's dick.

"I was hoping you already knew." Roy said disappointed at Linda's reaction. It seemed she wouldn't be that surprised if she was the one that put it on him. Roy leaned down to pull-up his pants.

"Hold on," Linda said as she seem to study the strange device. "Let me help these girls. I'll be right back."

"So you have the key?" Roy asked, but Linda was already heading out of the dressing room.

In a few minutes Linda returned. "Listen Roy, I admit you hurt me real bad. I thought we had something. I told a lot of people we were getting serious only to have you cheat on me. Everyone laughed at me when I told them I was dating you. I defended you, then you proved them all right. I was mortified."

"Well, still doesn't give you the right to lock my dick up like a little bitch." Roy said, relieved he had found his key holder.

"Here's the thing Roy, if you want that thing off of your dick you are going to have to do some things for me," Linda said with a smirk.

Roy was still struggling with the effects of the Viagra. He was horny as hell. Linda's beautiful rack, cleavage on full display, wasn't helping either. He was willing to do almost anything to get the stupid cage off to get some relief for his poor aching blue balls.

"Make it quick." Roy said.

"Quick was how you made it." Linda said laughing at her little joke. "First, you were a selfish lover. You owe me at least one good orgasm. Take off your clothes and get down on all fours."

This was the kind of punishment Roy could agree with. The insults he could have done without. He knew he was good in bed, even if she didn't.

"Damn, that thing is small" Linda pointed out as Roy got undressed. "And when did you start shaving down there?" She giggled at his smooth skin.

Embarrassed, Roy rolled his eyes and assumed the position. Linda dropped her panties and sat in the chair in the corner of the room. She lifted her small skirt then motioned for Roy to crawl forward as she pointed down at her bare pussy. Roy crawled right up to it and began licking. Linda pulled her top up to give Roy a good view of her wonderful big tits. She knew this would turn Roy on more, leading to more frustration for him. That turned her on more.

"Your oral skills were always a bit lacking," Linda commented after a few minutes.

"Kiss my ass!" Roy replied between licks.

"Roy, you are in no position to talk to me like that. Although, knowing that I'm getting my pussy licked while you are getting absolutely nothing does turn me on. Ha! You can't even get your dick hard." Linda said as she lifted her foot to Roy's shoulder pushing him backwards. She then got on the floor, on all fours, putting her naked ass in Roy's face. "How about you kiss my ass?"

Roy hesitated but then planted a kiss on Linda's ass check. "Keep going. You have a lot to make up for." Linda said as she pressed her ass into Roy's face. "Might as well lick my asshole while you're there." Linda giggled.

"Hey, I think you're taking this a little too far." Roy protested. He had never licked a girls bottom before.

"Really? So you don't want to see the key then?" Linda said as she looked back over her shoulder at Roy, who's face was deep in her ass crack. "Because If my asshole isn't as clean as a whistle when you stop again, you are leaving here without getting a glimpse of my key."

Roy immediately pushed his face into Linda's ass crack even deeper and began licking for all he had. "Good boy. Now stick that tongue deep in my asshole. Mmm..." As Roy stuck his tongue up Linda's ass, Linda pushed back and started ass fucking Roy's face. Roy noticed Linda slide her hand down to her pussy and start playing with it. As embarrassed as Roy was for being made to lick Linda's asshole, he was also jealous that Linda could pleasure herself with her hand. He would give anything to be able to reach between his legs to jack his dick off. As horny as he was, all he could do is sit there being used by Linda until she had gotten herself off.

When Linda was satisfied she sat back in the chair dressing while Roy stayed on all fours on the floor. She even laid one of her legs across Roy's shoulder as a foot stool. Roy started to object but was enjoying the sight of her pussy too much.

"Now Roy, for you to see the key work the lock, I need you to do just one more thing for me." She smiled.

"Come on Linda wasn't licking your ass enough?" He complained.

"That was to let you know your place, you little ass wipe. This is payback for cheating on me. Stand-up, I'll be right back." She instructed Roy. She then left Roy naked and horny in the dressing room.

When she came back she was holding a small piece of lingerie. It was a sheer, black, laced teddy. She held it up to Roy's chest.

"Hell no! I'm not wearing that." Roy said as he shook his head and backed away.

"Oh, yes you are." Linda demanded. "I modeled plenty of this stuff for you only to realize you were just using me. Do this last thing and I guarantee my key will turn the lock. Or, you can leave now, blue balls, steel cage and all"

"It's on but it's ridiculous." Linda heard Roy say as she waited outside the dressing room.

Linda pushed back the dressing room curtains to find Roy dressed in the sheer, black, teddy. Through the black lacy material she could clearly see the red g-string panties he was now wearing. The teddy came down just below his cock cage but his panty covered balls were exposed just beneath the hem line. His smooth shaven ass cheeks were partly hanging out in the back. He didn't look to stable on the 4" heels she had him wearing. He did looked ridiculous. Linda doubled over in laughter. Roy's face turned red immediately as he tried to avoid making eye contact with her.

"Ok, ok, you've had your fun. Now give me the damn key." Roy demanded.

"No, no, no... the deal was you have to model it for me." she said as she pointed into the store. "One trip down the isle ought to be enough." Then she disappeared around the corner into the store.

Roy stumbled out of the dressing room. He was having trouble with his new shoes. As he turned the corner a bunch of camera flashes went off. As his vision came back he noticed the little shop was packed with women, at least 20. They all started hooting and hollering when he appeared. They also started taking pictures. Roy tried to cover his face. Embarrassment washed over his whole body. He started to back-up but Linda stepped behind him pushing him forward. Unstable on his heels, he stumbled forward down the isle. The women had left the isle open for him as they slapped and pinched his ass as he passed them. Linda stayed behind him, nudging him forward, keeping him stumbling down the isle.

Soon he was about to reach the front door. Someone threw it open. Linda pushed Roy hard through it. Roy fell to the ground outside the shop. He landed on his face. His ass was sticking straight up with his head on the ground. The black teddy was around his chest. As he turned to get up he saw Linda through the glass door. She was holding a key in her hand. Roy froze. The key looked to big to fit the tiny lock on his cage though. As he made eye contact with Linda, she took the key and stuck it in the door. Roy heard a "click" as she locked the store door with the key. Roy desperately started trying to push the door open.

"You better go." Linda said as she raised her phone. "Don't make me call the cops to tell them about the pervert dressed like a woman trying to steal lingerie from the store." She said as she grinned at Roy. Linda was absolutely beaming with delight. "I have a store full of witnesses that saw you steal that outfit from the dressing room."

Roy looked around. It was just starting to get dark but people could see him clearly. He started to turn tail and run but stopped. "What about the key to the cage?" he asked, looking defeated.

"It wasn't me!" Linda replied making sure to look Roy dead in the eye. She wanted him to feel as betrayed as she had when he cheated on her. "I never had it." She said as she raised her phone as if she was going to make a call.

"Fuck!" Roy screamed as he kicked off the heels and took off down the street.

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AnonymousAnonymousover 7 years ago
Great story!

Ignore that jerk. You've got a great little story going here. Please keep writing and posting.

AnonymousAnonymousover 7 years ago
Relax dude!

If reading chastity stories get you this mad, I suggest going elsewhere. You either secretly like the idea and are afraid to admit it, even to yourself, or you think bashing authors will rid the world of this awful plague of awesomeness. Get a life, it's a great story we call FANTASY! Loser

Great writing StoryHacker, well done!

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