With a sigh, Jackie went out the door, looking every inch the sissy slut in her hooker clothes.

The door of the hotel room clicked shut behind her. She was now in the hallway with no money and no credit cards. She was 40 miles from home. And, she had no one she could call because her family and friends wouldn’t understand what the male they knew as Jack was doing in a hotel dressed up and made up like a hooker. He would be humiliated.

He was wearing a black, sleeveless turtleneck and a thin little red skirt. This had always been his favorite skirt because when paired with stockings and a little pair of thong panties, like he was wearing now, he felt almost naked from the waist down. And that was just how he felt now.

Well, standing in the hallway wasn’t getting him anyplace. Heck, last night he had confidently left his room and the hotel dressed just like this on his way to the bar. He had even turned some heads. Of course now it was only about noon and the sun was up, but he could still pull it off. With that, Jackie took over and she walked down the hallway toward the elevator with confidence, she even threw a little extra wiggle into her walk.

As she entered the lobby, she saw that a couple of the football players from last night were at the registration desk. As quickly as possible, she walked across the lobby hoping to avoid being recognized, but just as she opened the front door she heard, “hey, there’s that sissy slut from last night!” She didn’t wait to hear any more. She moved as quickly as she could considering she wasn’t used to running in 4 inch heels. She ran down the street, turned on the first cross street, then turned down an alley and crouched down behind a large cardboard box. Her heart was pounding, but she didn’t hear anyone chasing after her.

Jackie then looked into the open end of the box she was crouching behind. She realized there was a man sitting inside the box. He was staring right up Jackie’s skirt. “Hey slut I like your panties! I’ll give you a pull on my bottle if you give me a blow job!” Jackie quickly stood up and ran from the alley.

Once Jackie regained her composure, she realized there were many people around her on the street, all moving with purpose. Most of them ignored her. Some, mostly women, looked at her with distaste. Perhaps because they thought she was a tramp, perhaps because they knew what she really was. Some, mostly men, looked at her with lust. As with those who reacted negatively, she didn’t know if the reaction was because they thought she was a slutty looking woman or a slutty looking sissy. She felt ashamed to be out in public like this, but at the same time she found it to be very arousing and she hoped she was tucked into her panties firmly enough so that her growing erection wouldn’t show against the flimsy little skirt.

Forcing her mind of her sexual thoughts, she thought about her options. She could either walk home, or try to scrape together some cash to catch the train. Since the idea of walking 40 miles in high heels wasn’t appealing, finding some money seemed to be the plan. So, for money she could either earn it, steal it, or beg for it. She didn’t figure she was dressed to apply for a job, and with no experience, stealing would probably land her in jail. Not a very desirable prospect anytime, made even less desirable by her clothes. Begging it was to be.

Having heard some hard luck stories from others while walking to the train, she decided to give it a try outside the train station. It took her about 10 minutes to walk to the station. Along the way, she was pleased to see several men look her up and down appreciatively. There were even a couple of women that gave her the eyes. But she stuck with her plan. Reaching the station, she decided to focus on single men to ask for help. She spotted one and approached him. “Excuse me sir, could you help me with some money for the train? My purse was stolen and . . . “

“Get lost faggot!” the man said as he passed by.

Jackie had forgotten about her male voice. She tried again, this time making her voice as feminine as she could, but the man walked right by without saying a word. After a few more attempts, a man offered her a dollar for a hand job, which she declined.

Having had no luck with men, she decided to switch to women. The first woman she tried said, “You’re no woman, and your purse is over your shoulder.” Oops. She tried a different approach with the next woman. Using his male voice and dropping any pretense of being a woman he said, “pardon me ma’am, but as you can see, I have been the target of a prank. All of my money has been taken, and I was left in these clothes. Could you help me with some money so I can get home?” This approach actually worked, but very slowly. After an hour, he only had $3 towards a $10 ticket, and his feet were killing him. He decided to take a little break, and he sat down on a nearby bench.

He had been sitting for just a few minutes when a man sat down next to him, a bit closer than was comfortably necessary on the otherwise empty bench. “Hey sweetcheeks, how’s your day going?”

The man was sitting too close to ignore completely, so he said, “not very well, thank you for asking.” He then started to get up. The man took his hand lightly, but firmly, and pulled him back to the bench.

“Don’t go yet sweetcheeks, I’d like to help you.” This peaked Jack’s interest, so he relaxed a bit and turned to look at the man.

“I’m listening, but I would rather you didn’t call me that.”

“OK sweetcheeks, how about if I call you sissy boy instead?”

And Jack started to get up and he was again gently restrained by the man.

“I’m sorry, I was just teasing. My name is Charles. What may I call you?”

“Jack, er I mean Jackie.”

“Very well, I understand the problem. Based on your appearance, I will call you Jackie, and I am pleased to meet you. Please forgive me for my forward behavior, but I have been observing you for some time. I didn’t want to interrupt, but you obviously have a money problem, and, as I say, I believe I can help.”

“It would be a big help if you could loan me $10 so I can get home and change out of these clothes.”

“I was thinking more in terms of helping you in a way that would help me too. If I may speak frankly, you are an attractive crossdresser. I have clients who would be willing to pay handsomely to enjoy your assets for a short time.”

“You want me to be a whore? For you? Not a chance!” With that Jack stood up and walked away.

“My offer stands if you change your mind,” Charles called out to him as he walked away.

Jack was angry, but secretly pleased by the proposal Charles made. Vanity is not just for genetic women.

Jack went back to his begging. He hadn’t made any more progress when he heard a voice behind him, “Excuse me miss, but you’ll need to come with me.”

Jack turned and confronted a uniformed policeman. “What seems to be the problem officer?” he asked in his normal voice.

“Just step over this way to my car.” He pointed Jack down an alley where an unmarked police car was sitting, and walked him around to the rear of the car. “We received a complaint that you’ve been panhandling and soliciting for sexual acts. Do you have any identification?”

“I’m sorry officer, my ID was stolen along with my money, and I was just trying to get money to go home. Honestly, I didn’t solicit anyone!”

“Well, without any ID, I’ll need to take you to the station to get this figured out. Put your hands on the trunk, and spread your legs.”

Jack put his hands on the trunk, but as he thought about his clothes he stopped and said, “is this really necessary officer?”

The cop put a firm hand on his back and kicked lightly at his legs, “feet back and spread them,” he said harshly. Jack complied and felt extremely exposed. Bending over in the short skirt he knew his stocking tops and garters would be showing, and probably his ass thanks to the thong panties he was wearing. Once again, his embarrassment was tempered with excitement and he could feel his erection growing again.

The cop stepped between Jacks legs. He then began to run his hands up Jack’s nylon-clad leg. “Is that really necessary? It ought to be pretty obvious that I don’t have any weapons there,” Jack said.

“Shut up sweetcheeks,” said the cop. “Just relax and enjoy it.”

As the cops hands reached his thigh and continued up under his skirt, Jack realized he’d been had. But the cop was right about one thing. She was really getting excited about the situation and being felt up in public like this. The cop fondled her for a few moments, then pulled her clit and balls free of the little panties. Then the cop put a handcuff around her left wrist and pulled her up to her feet. Her hands were pulled behind her and her right wrist secured as well. She was turned to face the cop who once more ran his hand up under Jackie’s skirt and fondled her. “OK, into the car now,” the cop said.

Jackie was a bit disturbed to find that the cop had left her erect clit and her balls free of her panties, and it was causing her little skirt to tent up. “Excuse me officer, but couldn’t you put things back first?”

The cop laughed and put Jackie in the backseat of the police car. As he buckled her in he casually flicked her clit, “we might have to add lewd behavior to the charges!”

The cop got in the front seat and looked at her in the rearview mirror. “Nice beaver shot sissy boy”. Jack looked down and realized his little skirt wasn’t covering anything, and that the mirror gave the cop a straight shot between his thighs. He twisted his knees to the side, but his clit was still poking up and the cop laughed again.

At the station, Jack was forced to walk through the halls and go through much of the booking process while still in handcuffs. As a result, his clit and balls continued to be free of his panties. His erection had subsided, so this wasn’t as obvious as he walked by other prisoners and police officers. But then a male prisoner who was handcuffed to a chair whistled and said, “hey baby, sit on my face and I’ll eat my way to your heart!” This made him think again about being dressed this way in public and the way the cop had fondled him while he was helpless, and this caused his clit to again become hard. To make matters worse, the cop sat his in a chair with his legs pointing to the prisoner who had made the comment. When he looked up Jackie’s skirt and saw his growing clit, his next comments were much less positive. This also started a parade of people walking in front of Jackie’s chair. Each person would “accidentally” drop something, bend over to pick it up, take a long look up Jackie’s skirt, and then laugh at her embarrassment.

After everyone had some fun at Jackie’s expense, she was finally taken for fingerprinting. Her hands were released from the handcuffs and she quickly put her clit and balls back into the relative safety of her panties. After being fingerprinted and having her photograph taken, Jackie was led to the jail cell area. An officer directed her down a hallway of cells. There were men in cells on both sides of the hallway, and they made a number of lewd comments and suggestions as she walked by. Without conscious thought, Jackie swayed her butt just a bit more and gave some of the men a sly little smile.

Arriving at an empty cell, Jackie stepped in and the door shut behind her. She could still hear some comments coming from the other cells. Jackie realized she was again excited and aroused. “What’s wrong with me,” he thought. “This is a terrible situation, and I’m getting a hard-on!”

Jack sat on a bench and resigned himself to whatever was going to happen. At some point he would need to call his attorney. Unfortunately, his attorney was a long-time friend from college, so this whole situation was just going to get better and better.

After about 15 minutes, the cell door opened. Two men were sent into the cell with Jack. They sat on the bench across from him. They looked at him but didn’t say a word. Jack tried not to look at them, but he couldn’t help but notice that they were staring at his legs, and probably seeing up his skirt. Feeling oddly self-conscious, Jack crossed his right leg over his left. This caused them to smile and to share a look between themselves. They both got up and slowly walked over to Jack. One of them said, “mind if we sit here?” Before Jack could respond, they sat closely on either side of Jack.

“My name is Mike and this is my brother Pete. You know, you’re a very pretty lady. You look real sexy in that skirt, but it’s bad for your circulation to cross your legs like that.” While Mike was saying this on her left, Pete took hold of Jackie’s right knee and pulled it to the side forcing her to uncross her legs. Pete left his hand on her right knee and Mike put his hand on her left knee.

“Now look fellas,” Jackie started to say.

Mike stopped her by putting a finger to her lips. “Shh,” he said. “You’re going to have fun.”

Mike and Pete slowly began to pull Jackie’s legs apart. She tried to keep her knees together, but she couldn’t.

“I’m going to yell for help if you don’t stop this,” Jackie pleaded.

“You’ll be real sorry if you do that sweetcheeks,” Mike said with a grin.

Once they had pulled her knees about a foot apart, Mike and Pete kept hold of her knees but began to run their other hands up her thighs. When they reached the tops of her stockings, they gently caressed her thighs. They playfully tugged and snapped her garters. Jackie wasn’t sure whether to be terrified or in bliss, but she could feel how aroused and excited she was.

“Do you like that sweetcheeks? How about this?” Both men moved their hands up Jackie’s thighs, under her skirt and onto her panties which they lightly caressed. Mike pushed his hand through the leg of her panties and took hold of Jackie’s clit. “You know sweetcheeks, if we had thought you were really a woman and found this in your panties, we would have had to rough you up and then make sure every guy in this place had a chance to fuck you. As it is, we’re just gonna let you suck us off now.” With that, both Mike and Pete withdrew their hands. They stood up and walked back to the other bench and sat down.

Jackie didn’t know what to say. She put her legs together and tried to sit in a more ladylike way. Once again she realized that she had been set-up. The repeated use of the term “Sweetcheeks” convinced her that Charles was behind the whole thing.

“We’re waiting sweetcheeks. If we have to force you it will be a lot worse. Why don’t you just come over here and do what you know you want to do. Get down on your knees, pull out my cock and give me a great blowjob. Do it now or we get rough, and in the end our cocks end up in your mouth anyway.”

Pete came over and sat down next to Jackie again. She knew she was going to get hurt if she didn’t comply, and she also knew that they would indeed do what they wanted with her.

“You’re being a bit too slow sweetcheeks, now you’re going to have to crawl over to my cock. And this is your last chance. Get on your knees and crawl over now, or Pete is going to hurt you.”

Pete started to raise a hand, but Jackie slid to her knees before he could strike. She crawled across the floor to Mike. Naturally Pete now had a nearly unobstructed view of her ass as her skirt rode up in back.

“Hey Mike, she’s got a really cute ass. Can we fuck her instead?”

“Just be happy with a blowjob Pete. I think someone else has plans for her ass.” Both men laughed.

On her knees in front of Mike and resigned to repeating her role as sissy slut, Jackie reached for his zipper. “Not so fast sweetcheeks. Now you have to ask me nicely if you can please suck my cock. And I prefer to be referred to as master.”

Jackie swallowed any pride she might have left and said, “Please Master, may I suck your cock?”

“First you may feel my cock through my jeans so you can appreciate what you’ll be getting.”

Jackie felt the crotch of Mike’s pants. His cock was large, and Jackie could feel it throbbing through the jeans. “Now may I please suck your cock Master?”

Yes you may sissy, suck away.”

Jackie pulled down his zipper. She reached inside his pants and freed Mike’s large cock. Loosing herself to the feelings of excitement and arousal she felt, she gently caressed his cock with her hands. She lowered her mouth to gently kiss the head. Then she slowly wrapped her lips around the head. Mike groaned and wriggled a little. Jackie slowly slid her lips down the shaft of his cock. It was long enough that she began to gag before she was able to take it all in, so she reversed and ran her lips back up the shaft. At the same time, Jackie was using her hands to caress Mike’s balls. As she moved his cock in and out of her mouth, Jackie could hear Mike’s breathing change as he got more excited. She could also feel another pair of hands on her hips and she realized that Pete must have decided not to wait for his turn. She tried to move off of Mike to deal with Pete, but Mike grabbed her head and forced her to continue, and to take move of his shaft into her mouth and throat. She could feel Pete pulling her panties down and caressing her clit, her balls, and then her pussy. She let out her own groan of pleasure around Mike’s cock when she felt Pete put a moistened finger into her pussy. Just as she felt Pete’s cock begin to push at her pussy, Mike exploded into her mouth. Mike was holding her head and forcing it up and down on his cock as he finished his orgasm, and Pete was holding her hips as he rammed into her waiting pussy. Mike forced her to hold his softening cock in her mouth while Pete slammed away at her pussy. She could feel his balls banging against her ass over and over again. Finally he let out a little cry and exploded into her pussy. After a few more strokes he was done and he pulled away. Mike pulled her head off his cock and pushed her to the floor. Mike and Pete both quickly arranged themselves, zipped up their pants, and sat down on the bench together and ignored Jackie.

Moments later, Jackie heard the cell door open. Jackie was still on the floor, excited and breathing heavily, her clit fully erect, come dripping down from both her pussy and her mouth, and her panties still around her knees. The officer told her to get to her feet because her bail had been paid. With the smirking eyes of three men on her, she mustered what little dignity she might still have, stood up, pulled up her panties, straightened her little skirt, and walked out of the cell. She could hear Mike and Pete laughing as she left.

Going through the process of being released Jackie felt thoroughly confused. While she signed for the return of her purse, condoms and lube, she thought about what had happened over the last 24 hours. She had more or less willingly taken part in a sex show where she was the star performer, and she had just been through what amounted to a jailhouse rape. She should be angry or terrified or embarrassed. Instead, she felt wonderful. Truth be told, she felt like she had just experienced a dream come true, and in fact she had. It had long been a secret fantasy of hers to experience very much like what just happened and what had happened the night before. She began to realize that she wasn’t just the part-time cross dresser she had seen herself as just two days ago. She really was a submissive sissy slut. She enjoyed being dominated and exhibited and humiliated and sexually used.

Jackie was still thinking deeply about all this when she walked out of the police station. It was now early evening. She looked around to try to figure out where she was and what to do next when she heard a familiar voice. “Nice to see you again sweetcheeks.” She turned toward the voice and saw Charles walking toward her with a big grin on his face. “Did you enjoy your time in jail? Was it everything you hoped it would be?”

“I assume I have you to thank for paying my bail,” said Jackie. “I also assume I have you to thank for getting me arrested to begin with, and for arranging for the entertainment during my arrest and brief incarceration.”

“Good girl! I knew you were a smart one. Between your bail and various expenses, you now owe me $2,000. If you are prepared to pay that now, we can shake hands and walk away. Otherwise, we need to discuss our new working arrangement.”

In spite of Jackie’s new understanding of herself, she had no intention of being this man’s whore. “You know I don’t have any money with me,” said Jackie, “I will certainly pay you back as soon as I can get home, but I’m not going to be a whore for you.”

Charles shook his head. “I’m sorry sweetcheeks, but that just won’t do. Either you agree to do as I tell you until your debt is paid off, or I get you arrested again so I can withdraw the bail money. If that happens, I can guarantee you that you will be visited by some guys that won’t be nearly as much fun as Mike and Pete were. By the way, Pete went overboard when he fucked you. That wasn’t supposed to happen. I’ll see that he is properly punished. So what’s it to be? Work for me, or back for some fun and games in jail?”

“Since you offered so nicely, I guess I don’t have much choice,” Jackie told Charles.

“Great. Let’s step into my office to chat.” Charles motioned and a stretch limo pulled up. Charles opened the door. “After you sweetcheeks.” As Jackie stepped past Charles, he patted her on the ass, then watched with a smile as she sat down in the back of the limo and unintentionally gave him a good look up her skirt. He climbed in beside her before closing the door. The car took off from the curb. They were sitting in the back seat of the limo. About 6 feet in front of them there was a set of seats facing them. In the seats were Mike and Pete.

“It’ll take us a few minutes to get to your first appointment sweetcheeks, but first you need to sign this.” Charles handed her a legal-looking document and a pen.

“What is this?” Jackie asked dubiously.

“Let’s not start again,” Charles growled, “just sign the damn thing or we go back.” Jackie signed and handed the document and pen back to Charles. “That’s better. Now, let’s get acquainted. You remember Mike and Pete don’t you?”

Mike grinned, “hey, nice blowjob sissy boy!” Pete just smiled but didn’t say anything.

“OK Jackie, now get down on your knees on the floor here and suck my cock,” Charles demanded. When she hesitated he gave her a light slap and said, “you keep having to be reminded. Now don’t ever make me tell you twice again to do something.”

Jackie got onto her knees on the floor as she had been told. She looked to see Mike and Pete grinning and watching her every move. She realized that they were going to be looking right up her skirt at her ass when she went down on Charles. As she turned, she realized that having them look was turning her on, so she made a point of wriggling her ass a bit extra as she got into position to face Charles. She pulled down his zipper and reached into his pants and pulled out his cock. It was large but still soft. She bent over and used her hands to raise the cock to her lips. She ran her tongue around the head and along the shaft. As his cock grew she took it into her mouth and began to slide her lips up and down its length.

“How’s it look from there boys? Would you like to fuck her?” Charles asked after Jackie had his cock fully erect and was pumping her mouth up and down on it.

“Looks like a great ass boss! I’d do her,” said Mike with enthusiasm.

“Yeah, looks great boss,” said Pete a bit meekly.

After a few minutes, Charles came in Jackie’s mouth in a great gush, but he hardly made a sound. He then said, “tidy things up there sweetcheeks, then get back up here on the seat.”

Jackie gently tucked Charles back into his pants and zipped him up. She turned and sat down next to Charles. He placed a possessive hand on her thigh.

“Pete, you might recall that I told you specifically that I didn’t want anyone to fuck Jackie in the cell. She was only to suck everyone off. Now I understand how you were overcome with passion when you saw her cute ass waving in the air while she sucked Mike off, but you will need to be punished for disobedience.”

Jackie was embarrassed to have Charles talking about her blowing Mike and being fucked by Pete. But she felt a warmth emanating from where Charles had his hand on her thigh.

“Jackie has been through a lot so far today, and I think it’s about time that somebody sucked her off. Pete, come and do that.”

“Come on boss, I don’t do that sort of thing, I’m not a fag,” argued Pete.

“Unless you want Mike to persuade you, do as I ordered,” said Charles.

Jackie watched as Pete resigned himself to his fate and came to the back of the limo. He got down on his knees in front of her and reached up under her skirt to pull her now growing clit free of her panties. He bent down, put her clit in his mouth and started bobbing his head. Charles then put his hand firmly on the back of Pete’s head and motioned to Mike. Mike then came forward and knelt down on Pete’s calves. He reached around to unbuckle Pete’s pants. He lowered the zipper and pulled the pants and underwear down around Pete’s ankles. Pete was straining to get his face out of Jackie’s crotch, but Charles held his head firmly. He couldn’t move his legs and butt much because of Mike’s weight on his calves. Mike then pulled out his own cock. Jackie watched as he stroked it a few times and it grew to the large size she remembered from the cell. While he did this, he looked at Jackie and winked. Jackie blushed. Mike then plunged his cock rather roughly into Pete’s ass. Pete tried to scream, but it was muffled by Jackie’s clit. Charles forced Pete to keep pumping on Jackie with his mouth while Mike pumped into his ass. Both Jackie and Mike soon came, and Pete was unceremoniously dropped to the floor. Charles told the driver to stop the car and Mike pushed Pete out the door, his pants still around his ankles. The car then sped away.

While Jackie squirmed to get her clit and balls back into her panties, Charles asked her if she was satisfied with the punishment given to Pete. She agreed she was. “Very good,” he said as he patted her thigh. “Ahh, excellent timing. Here we are.”