Whodunit? A Chastity Mystery



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.


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.


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.

Roy didn’t get far before he heard a car pull up beside him honking the horn. Still running, he looked over to see Kate. “What the hell are you doing?” She laughed. “Did you lose a bet or something?”

“Can I please get into your car?” Roy pleaded.

Once in the car, Kate studied him from head to toe. She couldn’t hide her amusement of seeing Roy dressed in lingerie and a small red g-string. “What is going on?”

“It’s a long story that I don’t want to relive, ever. Could you possibly take me home?” Roy asked but before Kate could answer he remembered he didn’t have his house keys. In fact, all his stuff was in his pants back in Linda’s shop. “Shit, never mind.”

“Sorry, I couldn’t even if you wanted me too. I left my purse at home. I need to get it before I’m late for work.” Kate shrugged.

Kate worked at Roy’s favorite night club, The Hot Spot, as a bartender. She was a curvy black haired woman, with pale white skin, that oozed sex appeal. Though she was one of the hottest women Roy knew, he never made a move on her. He figured she knew he was a player and she knew how the game was played. Besides, he liked having one female he didn’t have to worry he pissed off. As ridiculous as he had been made to feel all day, sitting next to Kate dressed in lingerie, was the most embarrassing.

Roy wasn’t about to go to the club like he was dressed. He wasn’t going to walk home either. As they turned the corner Roy saw Smash Sporting Goods. He remembered a girl he dated named Jen worked there. “Could she be the one that caged me?” He thought. She certainly had a reason to. Roy had hit on her little sister while he was dating Jen. He hadn’t realized Jen’s sister was only seventeen. She had even threatened to have him locked up for messing with a minor. “Ah ha!” Roy said out loud.

“What?” Kate replied still confused about the whole situation. Still waiting for an explanation about what was going on.

“Stop!” Roy yelled. “Do you have any cash I can borrow?

“No, I told you I don’t have my purse” Kate replied.

“Really hasn’t been my day.” Roy mumbled. “Thanks for the ride.” He said as he jumped out of the car heading for the Sports store.

“Wait!” Kate yelled as Roy was making his getaway but he was already to far away. “Oh well, nice ass.” Kate thought.

Roy knew Jen would not be happy to see him. And, even if she did not have the key, he could at least get some clothes to wear. Luckily, no one was in the store when he stepped inside. It was late afternoon on Sunday. Roy ran to a rack of clothes. Quickly he started looking for something to put on.

Before he got started, Jen came out from the backroom. “Sorry, we just closed…” Then she realized it was Roy standing behind the rack. “You son of a bitch! You got some nerve coming here. Get the hell out!” she demanded as she pointed to the door.

“I can’t.” Said Roy meekly.

“Why the hell not?” Jen said as she walked towards Roy.

Roy stepped out from behind the rack letting Jen see he was wearing a sheer black teddy with a red g-string. Jen burst into laughter. “I always thought you were a little dainty boy, Roy.” I guess I was right.

Roy explained how he came to be dressed in lingerie. He had to pause his story a few times for Jen to stop laughing. Especially when he explained how he was trapped in a chastity device. When Jen informed Roy she didn’t have the key, he asked if he could take some clothes and pay her later.

“Hell no! Why would I help you?” Was her reply. Roy just waited for her to throw him out. After Jen took a moment of think, “You know I don’t like you Roy. I’ve always wanted to beat your ass for hitting on my sister. So, here’s the deal. We have a ring set up in the middle of the store for a boxing promotion. I will wrestle you for the clothes.”

With any other girl Roy would have thought this was a gift from heaven but not Jen. Jen was in great shape. Very muscular, and lean. Her ass looked like she could squat 300lbs. Roy also knew she was experienced at mixed martial arts. She was like a kitten in bed but he had felt her strength a few times. Still, Roy had few options. He could run off with the clothes but then he would be arrested for stealing. Explaining his chastity cage during the pat down would be no fun.

“Ok.” Roy said nervously.

“Not so fast… What do I get if I win?” She asked.

Roy shrugged his shoulders. He had nothing to offer. “If I win you have to go to the club with me tonight, dressed anyway I want you, and admit you are a disgusting pig.” Jen demanded.

Roy nodded yes. Jen went to the back to put on some wrestling clothes. She suggested Roy lose the teddy as it would be a disadvantage to him in a fight. Roy stripped down to the red g-string that hardly covered his cock cage and balls. While waiting he caught a glimpse of himself in the mirror. He was lean, muscular. He was a man. He had this. Except for the g-string, his physique screamed power.

Jen came back dressed in a one piece wrestling suit. It was tight and showed off her impressive athletic body. She laughed at Roy’s g-string one more time before they climbed through the ropes into the ring.

“Here are the rules,” Jen started, “no punching the face, no biting, no kicking and no getting out of the ring. Once the fight starts no stopping until someone has won. Break any of the rules and you are disqualified. The first one to give is the loser.”

Roy nodded in agreement. He was ready to get it over with but Jen seemed to be stalling by keeping her distance. “Is she scared of me?” Roy thought as a tiny grin formed on his lips. Soon, Roy realized how wrong he was. He heard the door to the shop open and five women came walking through.

“Please lock the door behind you girls, we are closed for business but I’m about to open up a big can of whoop ass in here!” she yelled to them.

Roy thought about bolting but remembered the rule about leaving the ring. As the girls approached snickering at Roy he turned three shades of red.

“This is the asshole I’ve been telling you about. Ready for some fun?” She said to them just before she locked her eyes on to Roy and started circling him. Her expression went from glee to serious in an instant.

Roy kept his front toward Jen as she circled. Suddenly she sprang on him. She shot for his legs. She managed to grab them both but Roy’s 200 pound frame was more than she could handle. Instead of toppling Roy over, he just squeezed his legs together catching her head between his knees. She was stuck on all fours in front of him. “Give?” He asked quickly.

“Hardly!” Jen shouted back.

Not wanting to let her go, Roy kept squeezing her head between his legs as he leaned over her back. Her tight ass was sticking up and boy did it look great. “Smack, smack, smack” was the sound everyone heard as Roy began to spank Jen.

“No…” Jen yelled as she wiggled her ass around trying to diminish the sting of Roy’s hand. As Roy played slap ass, Jen brought her right arm around and swung blindly above her head. Her fist made direct contact with Roy’s balls. He crumbled to the ground.

“You bitch!” he yelled as he curled up on the mat, grabbing his balls with both hands. Jen stood up and rubbed her stinging ass. Before Roy could recover she knelt over his head to put his head in a scissor lock with her powerful thighs. This had Roy’s face inches from Jen’s ass. Holding his head between her thighs, Jen then flattened Roy out laying her body across his in almost a sixty nine position, with her head just past his crotch. Roy tried to pry Jen’s thighs apart with his hands but she was too strong. The more he pulled at her legs the tighter she squeezed his head. Roy stopped trying, afraid he might pass out from lack of oxygen. To make things worse Roy’s arms were now trapped away from his body. They were being blocked form grabbing Jen by her knees against the mat.

The women watching realized Jen had gotten the upper hand and started cheering her on. “Well, lets get rid of this ridiculous thing.” Jen said as she ripped off Roy’s red g-string, leaving him naked except for his chastity device. When all the women got a good look at his tiny metal dick tube they roared with laughter. Roy used the last of his energy to try to buck Jen off but to no avail. Jen just squeezed her thighs together harder. In fact she squeezed so hard a fart slipped out and went right into Roy’s face. Jen was embarrassed but the women watching thought it was the funniest thing they had ever seen. Especially when Roy tried to shake his head side to side to escape the smell.

Finally, when Jen felt her strength fading she lifted up and punched Roy in the balls again. Then she released him. If Roy had any hope of fighting back it was gone now. Jen stood up, grabbed Roy by the hair and stood him up. She walked him to the ropes of the rings and laid his upper body across the top rope. She then pulled the middle rope over Roy’s head so that his head and arms were trapped in the ropes, as he was looking towards the women outside of the ring. She then took each of his legs and swung them over the bottom rope. Roy was trapped in the upper ropes while he was sitting with his bare ass hanging out on the bottom rope.

Jen stood back and admired her work. Just as Roy was recovering from getting punch in the sack, Jen started spanking his bare bottom with her bare hand. It hurt but not so much that Roy couldn’t handle it. Then a woman in the crowd got a ping pong paddle and threw it to Jen. Jen smiled as she raised it high in the air letting it come crashing down on Roy’s ass.

“Owwwww!” Roy screamed as blow after blow rained down on his ass. He wiggled and bucked but he couldn’t get free or avoid Jen’s blows. All the women cheered. Just when Roy thought he was going to actually cry form the fire Jen was lighting into his ass, she stopped. She leaned over the top rope and looked Roy in the eye.

“Are we done here little boy?” She asked with a smile of delight on her face.

Roy lowered his head and quietly said, “yes.”

Jen released him from the ropes then instructed him to stand in the corner of the ring. Jen put his red ass on full display for all the ladies to see. Many came into the ring to touch his sore ass that was actually radiating heat from the spanking. Others examined his chastity device, joking they needed to get one for their man. Several gave his sore balls a tug as they dangled free from the cock cage. Defeated, Roy just let it happen as he tried to pretend it wasn’t real, except all the attention to his body reminded him how horny he still was and how much he needed release.

This humiliating display went on for about 30 minutes. Finally Jen, who had disappeared, came back wearing a little red dress. She told the women that the show was over but to be at The Hot Spot tonight if they wanted to see more. After the women left Jen brought Roy out of the ring.

“Ok Roy, your sorry ass got beat by a girl. Now it’s time to pay up, bitch.” She said as she sat a brown paper bag on the sales counter. First she placed a pig snout mask over Roy’s nose. Then she placed a pair of hand cuffs over his wrist. “This is so you don’t get cold feet and welsh on our agreement tonight.” She said as she clicked the cuffs into place. Next, she bent Roy over the counter. “All this fun has gotten me so wet, Roy. How about you do a girl a favor?” She then raised her red dress, sat on the stool behind the counter and pulled her pussy into Roy’s face. It didn’t take long before Roy brought Jen to a massive orgasm. “Sorry I can’t return the favor.” Jen said as she gave Roy a fake sad face and reached between his legs and rubbed his cage. Oh how Roy wished he could feel her hand. His balls had never been so blue in his life.

Jen reached into the brown bag again to pull out a pink, curly, pig tail with a large butt plug on the other side. She held it up to Roy’s face. He looked away in shame. “I wouldn’t turn away if I were you. I forgot to buy lube when I ran out to pick this stuff up. You can wet it with your mouth or I can put it in dry.” she said as she pressed it to his lips.

Roy hesitated a bit before opening his mouth to let the plug slide in. When Jen thought it was good and wet she removed it. “You are pretty good at that, Roy. Had lots of practice?” she asked as she moved behind Roy who was still bent over the counter. Jen then pushed his legs further apart to give her better access to Roy’s asshole.

Jen placed the wet, pink plug up to Roy’s ass expecting to have a fight to get it in. To her surprise the plug slide in fairly easy. “Um, Roy, have you been taking it in the ass lately? You took that easier than I thought a virgin asshole would.” She said with a giggle as she saw his little piggy tail sticking out his ass crack.

Roy knew it went in easier because the lube he had gotten at the hospital was still in his ass but he decided to remain quiet. Even though it had slid in easy, it still was very uncomfortable having the plug up his ass. He gave it a little push but it was firmly lodged in his asshole. Next, Jen had Roy stand up. She slide a light pink pair of boxers over him. She put them on backwards so she could pull the tail through the fly opening. After that, she took some pink hair dye, in a spray can, and painted his whole body with it. Finally, she placed a small pink collar around his neck with a leash attached to it.

When she was done she stood back and laughed. “You now look just like the fucking pig you are, Roy.” Stay here while I make some final arrangements. Roy caught his reflection in a mirror. He looked absolutely ridiculous. He was pink, with a tail and snout. His balls, ass and asshole were all sore. And he still had the cock cage keeping him from touching his own dick.

“Lets go!” Jen said as she grabbed Roy’s leash pulling him out the door. The club was only about a block away so Roy knew they would be walking. He halfway wanted to get hit by a car on the way to end his humiliation. Luckily, they didn’t pass anyone on the way over. Dressed as he was he wasn’t sure anyone would even know it was him.

It was early for bar time, plus it was Sunday night. Roy thought he might get lucky and find an empty bar. He soon realized he was wrong again. A soon as they entered a big cheer went up. Jen had set up a ladies night for ladies only. Most were women that Roy had used and abandoned.

Jen led her pink pig trophy up to a small stage in the corner of the bar by his leash. The women pinched, poked and pulled Roy’s tail as he passed. Jen pulled Roy onto the stage in front of all the women. Roy was so nervous he thought he was going to die. Someone from the crowd reached up and yanked his boxers down. Other women helped her rip them away from Roy’s body. Another round of laughter erupted when the women saw Roy’s tiny cage locked on his dick.

Roy was so embarrassed his throat felt like it was closing up. He struggled to get out the words he knew Jen wanted to hear. “I am a…” but before he could get them out Jen cut him off.

“No, no, no, Roy. Pigs don’t stand on two legs.” She said as she pointed to the stage.

Reluctantly, Roy got down on all fours. Jen pulled him in a circle around the stage by his collar. This allowed the women to see his tail was really stuck up his ass. This caused even more laughter. Finally, Roy faced the woman, and with Jen using the leash to force him to look straight ahead he said what he had agreed to say, “I am a disgusting pig.” The crowd went wild.

Jen tied Roy’s leash to a pole on the stage. She left him there for the rest of the night while the women drank and partied. Linda was there, she threw his clothes up on the stage. Jill was there too, with Dr. Wilson. Roy could see Kate was tending bar, but to his relief, she never came over to see him up close. Though she had gotten a pretty good look in the car.

When most of the woman had left, Jen unlocked the handcuffs from Roy’s wrist. Roy scampered to get dressed and to get the hell out of there. “I hope you’ve learned a good lesson from this you son of a bitch!” he heard someone yell as he ran out the door. Halfway home he realized he still had the problem of the cock cage.

Several months had past. Roy never could figure out who had locked his dick up. He also couldn’t figure out how to get the cage off. He had gone to several professionals but all felt it would be too risky to remove without the key. The lock looked as if it was for a single key use only. Anything other than the right key would break it. No one would cut it because his penis was too close to the metal. When anyone tried to grind on it, it would heat up, almost burning Roy before even a scratch was made. He visited all the women he felt he had wronged. He humbly apologized to all of them. Never mentioning the cage but hoping one of them would produce the key but no one did.

Roy finally got the nerve to go back into the The Hot Spot. He heard a lot of women snickering at him as he took a seat at the bar. He knew his playboy days were over as all the women in town knew about his game and his cage.

“Didn’t think we would see you in here so soon.” Kate said as she placed beer in front of Roy.

“Got lonely hiding out in the apartment.” He said, looking down. “Besides, I don’t think I really have anything to hide… anymore.”

“You’re not mad about what they did to you?” She asked as she leaned in close to Roy.

“Actually I’m not. I’ve had a long time to think about it. I was really a jerk to a lot of women. I made them think they had a real future with a good man, then I pulled the rug out from under them, all for my own amusement. In a way I probably humiliated them more than they did me, just in a different way.”

Roy lifted his beer to take a sip. When he went to place the beer down he saw a very small key in the wet ring his beer mug had left on the bar. He looked up at Kate who was smiling back at him. “you?” He asked.

“Yes. I like you but I watched you play your game every time you were here. I could never be with someone like that. I was hoping I could get you to stop thinking with your little head and start thinking with your big head for a change. I knew that wasn’t possible as long as you could still play.” She said batting her beautiful eyes at Roy. “I didn’t expect all the other stuff to happen. I had no idea. I was watching your apartment that morning when you woke up. I followed you to the hospital and to the lingerie store. That’s why I was there with my car so quick. I was just about to take you back to my place when you jumped out of the car and ran into the sporting goods store. When Jen called to tell me what she was planning, I knew it was to late to help. After that night I was afraid to admit I was the one that caused you to go through all of that.”

There was a long pause in the conversation. Roy reached down and grabbed the key he had so desperately been seeking. He fumbled with it in his fingers for a moment then handed it to Kate.

“Why don’t you hold on to this until you think we are ready to take it off?” Roy said with a grin on his face. Kate jumped over the bar and gave Roy a big hug as tears streamed out of her eyes.


The End.



Leave a Reply

Your email address will not be published. Required fields are marked *

Translate »

You cannot copy content of this page