Chapter 4 -- Out on the Town

My feet and legs were sore. I was laced and locked into an overly tight pink corset, which was holding in, in turn, rubber breast forms that covered sharp nipple clamps which were inexorably piercing my nipples. I was being made to walk in 4-inch stiletto heels...showing my stockinged feet and painted toenails...to walk like a cheap whore on the make... up and down a hotel hallway...dressed in the shortest white leather miniskirt which barely covered my crotch and my pink panties...and which barely hid the welts of the ruthless beatings of her harsh cane. I was wearing my new white satiny camisole top with its spaghetti straps......my new blond wig...my newly pierced ears with the flapping hoop earrings...my painted eyes and face and my grotesquely-painted red-lipsticked mouth! And under it all...under that entire visage...the huge dildo inside my ass that was locked to that horrible chastity belt with its electronically activated punishment device.

The elevator stopped. Out came a well-dressed elderly couple. They looked at me in wonderment. Mistress quickly announced, "He's a sissy whore in training."

"Walk, Sissy Whore. Show them your stroll." I began walking, as ordered, and they watched me for a while and then laughed. Then, they walked on towards their room.

"You see, no one cares about you. No one knows who you are...or were." I couldn't believe that in the space of an evening, she had transformed me into what I had become -- a fully cross-dressed, totally enslaved, sissy whore.

"It's time to go and earn your keep. Stay out here and don't move." Mistress went into back into her room. I was left standing in the hallway. I could try to run, but I knew I wouldn't get far. I had no money, and no identification. How could I quickly get away? How could I explain what happened to me? How would I be able to get out of the chastity belt?

Minutes passed. Doors opened and closed and other hotel guests passed by me. Some looked at me as if I were a carnival side show. Two men stopped near me and leered at me. One whispered, "Cheap whore" to me and reached out and grabbed my breast. A sharp stab of pain, and I almost fainted! I realized the nipple clamps were going to be working their way all the way through. They laughed, and then they walked on. Embarrassed, I looked quickly down at the floor, but then remembered Mistress's warning. I quickly held my head up high.

Mistress finally opened the door and came out, holding her cane. She was dressed all in black. How appropriate, I thought! She was wearing tight black leather pants, and a black leather studded vest. She was wearing 2-inch high heeled black shoes. It was obvious that she wasn't wearing a bra. On her black studded belt, she had attached her dog whip on one side and her cattle prod on the other. In the back, she had placed the handcuffs in a leather pouch. She was wearing her infernal button device like one would wear a beeper, hooked onto the edge of the pocket on her pants. She had made herself up so that the skin on her face was porcelain white, and she had red lipstick on, just like mine, except that hers looked ladylike. On top of her head, she jauntily wore a black motorcycle cap, with her hair flowing out from the back. She was gorgeous. In other circumstances, I would have wanted to fuck her right then and there, except for my unfortunate and inescapable predicament.

"Okay, it's time for some fun," she laughed. We went down in the elevator and when it stopped on the ground floor, she grabbed my hand to walk like teen-aged lovers, or, more aptly, like a mother and child, through the lobby. Heads turned and people stared. "Remember how to walk," she said loudly to me, loud enough to be heard by all. "Rotate those hips...keep your sissy whore head up high." I heard murmurings and then laughter. I saw some people shake their heads in disgust.

Then, we were out the door and into the street. I heard lewd catcalls as the city's "worst" turned to watch me stroll. Mistress smiled at them and shook her head up and down approvingly. I knew she was pleased.

She ordered me to stop and stand right there on the corner. "Don't dare move." I had to endure more catcalls and insults. Several teen-aged boys stop to watch. One of them came over, reached under my miniskirt, and grabbed and caressed my ass. I couldn't do anything to stop them.

Meanwhile, Mistress walked to the other end of the block, turned around, and waved at me. She raised her hand and extended a finger and then I felt the familiar pain in my groin. I almost bent over double. She then turned, and walked another block away and did the same thing -- arm up, finger extended, and then the pain. I then saw a taxicab stop next to her and she got in. The taxicab disappeared from view.

Meanwhile, I had suffer through more name calling. Other men came over to stare at me and to feel my body all over. One of them walked right up to me, and grabbed at my crotch, while trying to kiss me with a beery, smoky mouth. At that moment, a taxicab pulled up next to me, and Mistress got out. "That's enough...get in," Mistress said in a dominating tone. "Sissy Whore belongs to me." Mistress then took me by the arm and helped me into the cab. I was terrified and shaking.

"West Street," she said to the driver. I could see him looking back at me in the rear view mirror, and then chuckling, almost silently, to himself.

"I just want you to realize, Sissy Whore, that all that you have in the world, now, is me." I wanted to cry; I was so afraid. "All you are, you must realize, is a piece of meat that I own, and can do with whatever I please."

"Now compose yourself," Mistress ordered. "Take some deep breaths." I sat there in the cab, trying to get hold of myself. It was difficult to take in more than half breaths because of the corset.

The cab stopped and let us out. I saw prostitutes -- men and women -- and men dressed like women -- and some dressed like me, I horrifyingly realized -- walking up to cars that had slowed down and stopped. I saw several talking to the drivers of the cars, obviously negotiating and transacting business. Others got into the cars, which drove away to do what they were going to do. We watched for a while, and then Mistress turned to me and said, "This is where you will end up if I become displeased with you."

One of transvestites came over to me, and looked me over. In an effeminate drawl, he/she asked, "Oooh, is this a new girl out to make some money?" Mistress laughed and replied, "Not yet...not for a while, anyway."

After a few moments, we walked down the block to a bar. "It's time to for you to make some money for me," she said. I had to carefully walk down several stairs to get to the front door and then through the door into the darkness. My eyes had to get accustomed to the dimness and then I looked around. This was one very rough trade bar. All eyes turned to us.

Mistress stood there until she had everyone's attention and then loudly announced, "My virgin sissy whore will blow anyone in this place for five dollars." I was mortified. There was a murmur of reaction. She made me stroll to the back of the room and had me get down on my knees and turn face the crowd. "Who's first...step right up." There was a jostling and one guy, dressed in a black t-shirt, jeans and combat boots, strutted over to us. All of his buddies were watching.

"Since this is Sissy Whore's first blowjob, this one'll be free," Mistress again announced. The men started to laugh and cheer.

"Come on over...don't be shy," she told black shirt. Mistress positioned him so that his crotch was right in front of my face. She turned to me and instructed, "Okay, roll down his zipper and pull out his dick."

I reached towards him, opened his zipper and reached for his maleness, which was becoming aroused. It was becoming even more erect in my hand. I pulled it out. "Give the tip of his dick a nice kiss with your juicy red lips," Mistress directed, and I did. I had never done this kind of thing before and, yet, I couldn't stop what she was doing to me.

"Now grab his ass and pull his dick into your mouth. Make sure to make it really wet as it goes in. Don't you dare gag when it goes all the way in."

All eyes were on us as I slowly drew his manhood into my mouth. When it got far in, I couldn't help gagging and everyone laughed. Mistress laughed, too. She must have let that infraction pass by because and I was really glad that she didn't press the button to activate her pain maker.

"Now that you know how far is too far, I want you to give him the best blowjob of your life," Mistress demanded. "I want you to keep his dick nice and wet as it goes in and out of your sissy whore mouth. And, I want you to swallow his cum when he's done."

I looked up at black shirt and he smiled to me. Everyone was watching with rapt attention. He grabbed the back of my head to more quickly control my head and to move it back and forth. I was forced to service him, on my knees in my new sissy whore ensemble. His dick went in and out. I grabbed his buttocks to hold on to him. I could feel his gyrations increase and he finally held my head tightly as he came deeply in my mouth. I swallowed down the salty, slimy liquid as quickly as I could. I heard applause and cheers.

"Now lick him clean and again kiss the tip of his dick as a thank you," Mistress ordered.

Mistress took lipstick out from her pocket and again painted my lips with the grotesque red color. You'll redo your own lipstick next time. She then announced, "The next one will cost five bucks...who's next?"

Another man came over, and handed her a five-dollar bill. "Introduce yourself to the man," Mistress directed.

"Hello, my name is Sissy Whore, and my Mistress would like me to give you a blowjob," I said.

I felt the pain in my groin. "YOU want to give him the blowjob...now say it!" Mistress warned.

It was bad enough being forced to do what I was doing, but I so humiliated, being chastised like that. I complied by saying, "Yes, I want to give you a blowjob. Let me open your zipper and kiss the head of your penis."

I went through this exercise countless times during that night. So many different anonymous dicks...being forced to have them move, wet and slick, in and out of my mouth...holding on to their asses...having them hold my head...having them ejaculate deeply in my mouth...and then having to swallow their cum.

After hours of this, I heard the bartender announce, "Closing time." It must have been approaching four in the morning. How long would this go on?

Mistress said, "You did nicely for us. We made almost one hundred dollars. Now, we'll give you something to wash that taste out of your mouth."

She made me get up. My knees and legs were sore. My mouth and jaw were throbbing in pain. She walked me into the men's bathroom. "Don't you worry...this is a liberal sort of place," Mistress snickered.

Mistress reached around to her pouch and took out the handcuffs. She then made me kneel down on the wet floor in front of the urinal. She locked my left wrist into the cuff, pulled my wrist under my legs, inside the fold of my knees, and then held down my right wrist and attached it to the cuff. My locked wrists held me in a kneeling position. She then pushed me back and positioned me so that the back of my neck was right up against the bottom lip of the urinal. She took a length of cord out of a pocket, drew it under my chin, and pulled it up and around the piping above the urinal, stretching my head up and back. Then she tied it off in a knot. A feeling of dread was quickly enveloping me. "There'd better be no complaints," Mistress instructed.

"Please, Mistress. Please don't make me do this," I implored.

"Nonsense. This is all that you're good for," Mistress said as she sneered at me. "After all, all you are is a worthless piss-drinking sissy whore."

Then she smiled and said, "Oops, I almost forgot." Out of her pocket she drew out a metal ring, surrounded by rubber, which was about two inches in diameter. "Open your mouth wide!" she commanded. She positioned the ring inside my mouth so that my teeth fit into grooves in the rubber. She then inserted what looked like old roller skate keys into each side of this ring and started to turn the keys. As I heard what sounded like ratchet clicks, my jaws were forced to open even wider. I was helpless... I couldn't move my head; I couldn't close my mouth. "Good, that will keep your mouth wide open. Now don't forget to swallow!"

And then she walked out, leaving me there, unable to move, on my knees on that dirty, urine stained tile floor.

A few minutes later, a man came in, looked at me and laughed. He came over to me, opened his zipper, pulled out his dick and stuck it deep in my mouth. I felt a stream of his hot, salty piss going down my throat. I could hardly breathe and I swallowed as fast as I could. When he was done, he patted the side of my cheek, saying, "Good girl," and left.

After that, there was a steady procession of men into the bathroom. Some came just to watch and cheer. Some of them purposely pissed all over my face. Some of it went into my eyes and stung; other piss went up my nose. A lot of it was sprayed all over my clothes and down under my corset. My aching nipples stung from the salty liquid. Even though I was becoming sick to my stomach, I proudly held my head up high, as Mistress commanded, and took in all that I could.

Then, abruptly, it was over. Mistress came in, looked at me and laughingly said, "You smell like piss. and you look like shit. Your makeup and lipstick are all smeared." And she slapped me twice on my face to emphasize her point. "C'mon, it's time to go back." She cut the rope, unlocked my wrists and helped me get up. But she kept that horrible mouth dilater fastened inside my mouth. She hailed a cab for us and we went back to the hotel. The driver almost refused to drive us, but relented when Mistress promised to double the fare. He had to open the windows wide because of the reeking odor.

The few people we passed remaining in the hotel at that early hour all turned around, to look at Mistress and her sissy whore, and to also find out where the stench was coming from. I saw many of them turning away in disgust and revulsion after also seeing me with my mouth kept wide open, like a circus freak.

Finally, we were in the elevator on the way up to Mistress's hotel room.