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  • Whodunit? A Chastity Mystery Pt. 01

Whodunit? A Chastity Mystery Pt. 01

This story is a sort of "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.

*****

Roy woke up in a fog. His head felt like his brain was bigger than his skull. It was Sunday morning and he was lying in his bed, alone. He remembered going to the club the night before but couldn't remember coming home. That wasn't all that unusual for Roy but the empty spot on the bed next to him was.

Roy was a player. He knew it. Damn, he was proud of it. Roy had the looks for the game too. The height, the chiseled jaw line, the muscular build and the smooth lines or, smooth lies, as Roy like to think about them. Was Roy a player because he was good looking or did being good looking make it easier for Roy to play? He didn't know and really didn't care.

Roy loved women. Sure the hot ones were his most common target, but not always. There was just something about women that drove Roy wild. They knew just how to stand, how to toss their hair around. Their curves were smooth, their walk was magical. Just putting a finger to their mouth the right way could be the sexist thing in the world. The way they laughed, the way they smiled. Yep, Roy loved the women.

What Roy didn't like was commitment. He never wanted to get past the visual. What he had learned is that after a few dates he would find something about them he didn't like. Worse, they were bound to find out things about him. Who needed it? Roy was happier with a one night stand then moving on. The biggest draw back to this plan was seeing the women he slept with at the clubs and bars he frequented. It wasn't like there was an endless supply of places to find them.

As Roy tried to remember the night before he stumbled out of bed to go relieve himself. His sight was blurry and his footing was unsteady. "Man, I really tied one on last night," he thought with a little pride. As Roy reached the toilet he pulled down his boxer shorts to get down to business. Only, his dick wasn't there to grab on to. "Holy shit!" he yelled in astonishment. His dick was there, it was just encased in a small cage of steel no more than two inches long. He quickly felt all around the device to find a way to remove it. His legs were shaky, so he sat on the toilet.

Bewildered and terrified, he studied the device. He had seen chastity devices in porn movies that looked similar but they were plastic, rubber or made of cheap steel. This thing was heavy steel. His dick was so jammed into it that his skin poked out of the small openings on the side. His balls hung down in front of a tight, thick, stainless steel ring that locked the device to his crotch. Too close to cut off and he damn sure wasn't going to get near it with a torch or grinder. He could feel a small hole on the bottom part of the ring that he assumed was key hole but didn't know for sure. "Fuck!" he yelled as he pulled at it in disgust.

Still he had to pee. There was little hole at the end of the cap. As Roy began to pee he realized his penis hole didn't line up with the cap exactly. Urine sprayed in multiple directions. Roy had to quickly push it down towards the toilet bowl. It seemed sitting down would be the only way he could pee until he got this stupid device off his dick.

In the kitchen Roy took a few aspirin for his head. He was still trying to remember the night before when a piece of folded green paper caught his eye on the kitchen table.

"Hey Player,

You are in a world of shit now. If you are reading this then the drugs have worn off and you now realize that you are caged. Say good-bye to your love life. You can't touch it. You can't get hard. You can't have sex. You can't play with it. Your days of treating women like dirt are over. You have left a trail of humiliated women in the wake of your playboy ways. No more.

Now, to show I'm not a total bitch, I will give you a chance to redeem yourself and gain access to your dick again. If you can gain my forgiveness by demonstrating that you have changed your ways I will happily give the key to your dick back to you. Though I seriously doubt a self-centered ass like you could humble himself enough to gain a woman's forgiveness. You would first have to be able to understand how a woman thinks, feels and lives to know what damage you have caused. I doubt you are capable of such feelings.

Good luck Asshole.

Sincerely,

Your Key Holder

P.S. The lock on your cage will break if anything but the key is inserted. I checked with the hospitals. They might be able to remove such a device but it will be painful, damaging, embarrassing and humiliating."

"What the fuck! This stupid bitch is crazy." Roy thought as he threw the letter down. Roy racked his brain as to who it could be. The problem was, the more he thought the more names he thought of. Roy had screwed a lot of women. Worse, the way Roy put distance between him and a new lay was by being the biggest jerk he could be. When he saw them in the club he would tell them that they weren't as attractive as they were when he was drunk. Or, he told them he had a girlfriend and made a drunken mistake. Roy said whatever it took to get them away from him. He knew it wasn't nice but it was only part of the game.

Too many women and too many tears for Roy to possibly figure this out. He stared at the letter. "Ah ha!" he thought. The hospital. That's where Jill works. The letter said she had checked with the hospital. "That's because she works at the hospital," he thought, happy to have a little direction. Jill was a cute little catch that he had picked up at a bar across town a few months ago. He told her all the right things to get her into his bed. He told her she was the type of girl he could introduce to his parents, a real keeper. It had to be Jill. She was pissed when he told her the next day he would never take a whore, who would sleep with a guy on the first date, to his parents house.

Roy showered and headed to the hospital to confront the bitch. Jill worked in the ER as a nurse. She had blond hair that she kept in a pony tail while working. She was a bit to the short side but lean, so she didn't appear short. Roy liked a little more meat on his girls but what Jill had was located in the right places.

Jill could clearly see Roy was irritated when he asked to see her. They went into an exam room to discuss whatever it was Roy was upset about.

"A lot of nerve you have showing your face around her after what you pulled on me." Jill started.

"After what I pulled?! Holly shit, you've got some nerve yourself" Roy shot back.

Jill couldn't have been more confused. "Listen Roy, I get it. You used me. It was just a game to you. I get it now but if you think I'm going to fall for it again you better head out the door right now. I literally hate your guts."

"I know, but that still doesn't give you the right!" Roy said bitterly.

"What the hell are you talking about?"

"You know!"

Jill shook her head no.

Roy was getting more mad by the minute. He unzipped his pants, snatched them down to his thighs, exposing the medal cage locked to his dick. "This! I'm talking about this cage you locked onto me."

It took Jill a second to realize what she was looking at. Then she burst into laughter. "Oh my Roy, seems you have pissed off the wrong girl." She moved in closer to inspect it.

"Very funny... ha, ha... now get the key and get it off." Roy said turning a little red at being laughed at.

"Honestly Roy, I didn't do it but I wish I had. I'm glad someone put that thing out of commission." Jill giggled. "It looks pretty solid too." Jill's medical mind started thinking of how to remove it when she realized the gift she had just been given. "I really don't have the key, Roy, but I might be able to remove it. Take off your clothes and put on this gown. Hop-up on the exam table and I'll be right back."

Roy was still convinced Jill caged his dick. "Ok, so we are going to have to go through this little dance to get it off? Whatever... have your little fun."

Roy removed his clothes, put on the gown, climbed on the exam table and waited for Jill to return. It didn't take long for Jill to return with another women. "This is Dr. Wilson, Roy. She is going to exam you to see if we can help you with your... situation." Dr. Wilson looked to be in her mid 40's. She had red hair and appeared to be in excellent shape. A runner perhaps?

"Lay back on the table, Roy. Let's see what we are dealing with." She said calmly.

Roy laid back with his legs hanging off the front of the exam table. He was embarrassed when Dr. Wilson moved his gown to the side to saw his metal chastity device. She looked at Jill with a big smile and immediately turned her head to keep Roy from seeing her smile. "hmmm, I've never seen one of these." She pulled at is a few times. "Seems like a very tight fit too. "

"Ow!" Roy yelled when she pulled it to hard. "Are you trying to rip my balls off?! How about some damn bedside manners?"

Dr. Wilson immediately knew what Jill had meant when she refereed to Roy as an ass. "Oh, sorry. I didn't see the ring that goes behind your scrotum. I need to get a better look at this... so I don't hurt you." She said as she winked at Jill. "Jill, please put Roy's feet in the stirrups so I can see the bottom of this device."

Jill started pulling the stirrups into position with a little grin on her face. Dr. Wilson stood up to adjust the light right to Roy's crotch.

"Oh hell no! Those are for girl exams, not me." Roy protested.

"Roy, if you want me to remove that thing I need to see it and access it." Dr. Wilson said with an authoritative tone. "Or, we can forget this and let you figure out how to get it off?" Then she just stared, waiting for a response.

"Fine!" Roy said as he lifted his feet into the stirrups. Roy had never felt so exposed in his life. The stirrups kept his legs spread wide apart. Dr. Wilson made him move to the edge of the table so his ass was on full display as well. Jill placed some straps over his ankles to secure him in.

"Jill, shave his pubic hair so we can see this thing properly. Get his temperature as well." Dr. Wilson said as she snapped off her latex gloves. "I'll be back soon." Then Dr. Wilson left the room.

First, Jill took a thermometer and stuck it in Roy's ass before he even understood what she was doing. "Hey! This is bullshit!" Roy protested. Jill then got a razor and started to shave Roy. He didn't seem to mind until she finished with the hair above his dick and balls and started shaving his asshole and ass. "Hey, that's not necessary!" he complained.

"She said pubic hair. This is pubic hair. Besides, if she has to use a torch or something you don't want your hair to catch fire." Jill told him with a smirk. The thought of a torch near Roy's dick made him shiver. Soon Jill was done. Roy was baby smooth. Jill gave him a little pat on the ass as she pulled the thermometer out of his ass and wiped the lotion away. "Temperature is normal" She announced. Soon Dr. Wilson returned.

"This thing is solid." She said as she pushed it around. "It's so small too." She said as she measured the tube holding Roy's dick. "Is all your penis in the tube?" She asked as Jill let out a small giggle.

"Of course it is. Where else could it be?" Roy replied.

"I guess your right. Your scrotum protrudes at the end of the tube but before the ring holding it on." She said as she grabbed Roy's balls and gave them a few tugs in a different directions. Roy immediately felt his dick start to stiffen only to be denied by the cage. "It's just so tiny. " She repeated

"I do remember him being to the small side... but I didn't know it was that small." Jill interjected.

"Hey, I don't need this shit. Just get it off." Roy fussed to move things along.

Annoyed, Dr. Watson gave Jill a pill. "Please give this to Roy. Maybe it will relax him enough to assist us in getting this off."

Roy took the pill while Dr. Watson got some equipment out. Looking through the spaces on the cage Dr. Wilson couldn't see any space on the side but she thought there was room to the front. "I know this is hard to believe but I think I can see some room between the front of the cage and your penis. Your small size might be an advantage to us."

Roy turned red with embarrassment. Jill could not have been more amused. Dr. Watson picked up some bolt cutters and leaned over Roy's open legs to see the best place to cut. Roy was nervous but still managed to notice the doctor's tits hanging down as she leaned over. Soon his dick started to try and get hard again.

"Hold on, Roy are you getting erect? Your penis just started filling up the cage. I can't cut it like that you naughty boy." she scolded him.

Roy peered down to see the cage being pushed forward by his dick. His dick was straining so much to get hard the ring behind his balls was lifting them up. It seemed the more Roy tried to will his dick to get smaller the more it tried to grow. It was very uncomfortable, but worse, it was embarrassing to have these women watching him trying to get hard, only to be denied by his cage.

"Jill, we must do something to reduce this little attempt at an erection. Please ice his cage down and I'll be right back." Again she left the room.

Jill placed an ice pack on Roy's cage in an effort to shrivel his dick, and waited. "That must really suck not to be able to get hard anymore. And you think some girl did this to you. I bet she is laughing her ass off about now." Roy remained quiet, trying to concentrate on his freezing dick.

Soon the doctor returned but realized Roy's dick was still trying to get hard. "Hmm... we will have to try something else." Dr. Watson pulled out a long, slender shaft out of her pocket. "We have to get his erection down, Jill. Get me some Ky Jelly." The doctor sat down and spread some of the cold lube on Roy's anus with her finger.

"Hey! What the fuck are you doing you idiot?! The problem is a little higher." Roy demanded to know as he wiggled his ass away from her finger.

Dr. Wilson gave Roy's balls a good slap. Jill chuckled, as she had never seen Dr. Wilson treat a patient in anything but a professional manner. Though, Roy did dissevered whatever he got. "That's enough from you. I'm trying my best to help you because you are a friend of Jill's, but I won't have you treat me or any other woman the way you do. I'm about ready to forget this whole thing." Dr. Watson winked at Jill again.

"No. Please, it's just I wasn't expecting you to touch me there." Roy said meekly still feeling the sting on his balls.

"Ok, no more trouble from you mister." Dr. Wilson said as she placed the end of the shaft and started sliding into Roy's anus.

Roy sat quietly. He glanced at Jill who was totally fixated on the white plastic device being shoved up Roy's ass. Roy closed his eyes as he tried to adjust to feeling of something invading his asshole. It didn't feel all that big but it was big enough to cause discomfort. When the doctor stopped pushing it in Roy opened his eyes to find Jill looking him square in the face with a big smirk of satisfaction on her face. Roy's face flushed with embarrassment. Before he could break eye contact with Jill, Dr. Wilson turned the device on in Roy's ass. Roy felt his ass start to vibrate. His eyes grew big as the feeling hit his prostrate. Jill covered her mouth to keep from laughing at Roy's reaction.

"Roy, I am stimulating your prostate in hopes that we can get some of your semen out. That might help you deflate your erection. Normally, you could just masturbate but obviously that is beyond your control at the moment." The doctor instructed.

In just a few minutes Roy felt like he was going to cum. Jill noticed his hips moving a little bit back and forth. The doctor noticed it too. "Ok, if you think it will help," she said as she started to slide the stimulater in and out of Roy's anus. It was humiliating but all Roy could concentrate on was the feeling of cumming. Within a few minutes of being ass fucked by the doctor's probe, Roy started to buck desperately. He looked down between his legs to see cum dribbling out of his cage in a small stream.

"Is he cumming doctor?" Jill asked, disappointed Roy was getting any pleasure out of the situation.

"Not exactly, Jill. He is ejaculating but he doesn't feel like he normally does when it happens. The pressure is relieved but there is no pleasure for him. It's probably very frustrating for him, actually."

The doctor pulled the shaft out of Roy's anus. It made a loud "pop" that caused both women to laugh. Roy wanted to climb under the table after his little performance in front of the two women. Of course he couldn't because he still was strapped into the stirrups and had the cock cage locked on. Worse, he was now extremely horny. While he did cum, he didn't get any satisfaction from doing it.

"I guess it didn't help." The doctor said looking down at Roy's locked penis still trying to push the cage off his balls."

"Dr. Wilson, the ambulances are here. They need you in there stat!" Said a voice from just inside the door. Roy looked up to see a little brown haired girl, about 19 years old, staring directly at his chastity cage. Instinctively he tried to squeeze his knees together but to no avail. Quickly he placed his hands over his cage.

"No need for that, Roy. We have to go. Trish here will have to help you up." The Doctor said as she headed for the door.

"But, you didn't get it off" Roy shot back. "You made it worse! You suck so bad!"

Jill smiled at Roy and gave him a little wave as she left the room.

"Sorry you had to deal with that asshole." Jill told Dr. Wilson when they were in the hall.

"Oh, don't worry, I enjoyed it." She smiled. "Especially knowing that the Viagra we gave him will keep his little penis trying to get hard for hours. He will be a very frustrated, angry, young man."

Roy could hear both women laughing loudly as they headed down the hallway.

"Wow, I've never seen a man in stirrups before" Trish giggled as she wiped a little bit of lube off of Roy's ass. "And I've never seen one of those." She said nodding at Roy's cage. Roy was embarrassed to have this girl wiping his ass and getting a good look at his tiny tube cage.

"I suppose you see this stuff all the time?" He said trying to hide his embarrassment.

"Oh gosh no, I just work at the desk up front. Dr. Wilson asked me to come get her and help with you." She said as she lifted his legs out of the stirrups. "This is the first time I've ever helped with a patient. And I've never seen anything like that thing on your pecker." She said as she took a closer look. "So small..." She said, but more to herself than Roy.

"Well, if we are finished I've got to get back to the phones. I'll close the door so you can get dressed." She giggled.

Roy dressed as fast as he could. He wanted to get out of there as fast as he could. He had been humiliated by the doctor, and in front of Jill no less. As he pulled his pants up he had a hard time getting them zipped over his cage that was still restricting his painful hard-on.

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. He glanced down the street full of shops. "Linda!" Linda was a busty babe that owned a lingerie store that was just down the street.

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