Whodunit? A Chastity Mystery Pt. 03

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.

*

"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.