Dress Up Ch. 02

She knew that people were staring at her as she walked back to their table where their food was waiting. The waitress and the host gave her a disgusted look and she smiled at them, knowing that they would kill to be in her shoes, to have what she had. It was only jealousy that made people act this way - it was about their shame and their inhibitions, not hers and not his, certainly. They had found their way around all of that, done it together and built something so beautiful, so beyond anything that either of them had even begun to dream of, when they initially met. It had been a long, hard road but they had arrived.

He came back out of the ladies' room and sat across from her, in the booth.

"Do I have your permission to sit on this side of the booth?" he asked, ready to move if she so desired.

"No, that is fine," she answered while moving his placemat and his food towards him.

It was hard not to feel the stares but she rose above it and began to talk to him about how much he had pleased her. She appreciated his lack of questioning her decisions, her power over him and her uncanny ability to know what he wanted oftentimes before he did.

"How is the plug, slave? Is it filling up your tiny manpussy?," she asked in a normal tone, as if she were asking him about his day at the office.

"Yes, Mistress, it feels wonderful. Thank you for asking. I hope I was able to please you in the bathroom, it seemed to take you a longer time than usual to come," he wanted to keep the conversation going, to hear her tell him that he had done a good job. She hated when he fished for compliments as she had found that she could easily spoil him. She walked a fine line between withholding and rewarding.

"Are you looking for a compliment from your Mistress?" she asked as her foot found its way to his cock. She was still wearing her highest heels and this is the part of her shoe that pressed against his member. He almost spit out the food that was in his mouth, the pain was so great.

"No, Mistress, I am sorry for bringing it up," he struggled to get out, each word being a chore as his cock was being pierced by her heel.

"Do not ever, ever ask me to compliment you. I have told you many times that if I feel that you have done an exemplary job, I might reward you but if you are doing what is expected of you, what I have trained you to do, you don't deserve anything but to please me. What is wrong with you? Have I spoiled you tonight by bringing you out, dressed as the woman that you are, deep down inside, the hidden self, the one you fear more than anything else in the world? I think I have," and her heel dug deeply into his cock.

"I am so, so sorry, Mistress, please, please forgive me and my selfishness. I am sorry," he begged, as the tears welled up in his eyes.

"Oh, poor baby, are you going to start crying, right here at the table? Just like a real woman? Go ahead, let those tears fall, and then people can really stare at you, wondering what the fuck is wrong with that pussyman at that table. Yes, I am guessing that people will be talking about you for years to come. 'Remember that big man we saw that night, dressed as a woman, crying at the table?' they will say to each other. What a pussy," she was shaming him now and he knew, in his heart, that he deserved it, every bit of it. He knew better than to ask about his performance, he knew that she would either punish him (as she was so brutally doing now) or she would let him be - a reward was rare, very rare but when it came his way, it was oh-so-good and he lived, he served, he loved for those instances when her expectations of him were not only met but exceeded. That is when he felt the most whole, the most complete, the most like the man he was put on this earth to be.

She lifted her heel off of his cock and he took in a deep breath. She leaned across the table and wiped away his tears with her napkin, making a fuss over him, embarrassing him further.

When his breathing normalized, his Mistress told him that it was time to go, throwing $100 bill on the table. They might talk about the two of them for years to come but no one would never say that she was a bad tipper.

"C'mon, Frances, it's time to get out of here," she said, reaching her hand out to him to help him get up from his seat in the booth.

They both felt everyone staring as they walked to the door and she smiled at him, placing her hand on his lower back as she opened the door for him, walking behind him before turning around to smile at the host, giving him a wink.

Once in the car, she told him, again, to relieve himself. She had another place in mind, to go dancing, and she didn't want to feel his pitiful little cock pressing up against her when they danced.

"Do what you did before. Pull your dress up, so I can see your little cock, pull down your panties. Maybe this time you can have better aim and not get it all over your dress again. Remember the time I had your hips up in the air, with a dildo up your ass, and your cum shot right into your mouth? You loved that, didn't you? Tasting your own cum. You just love the taste of cum, let's face it. You are my little cumslut. You will eat your own or another man's, that has been freshly deposited into my cunt. You don't care whose it is, you just want to eat it all up, don't you?"

As she spoke, this way, to him, his cock grew harder and harder and more and more full of his own cum. She knew just what to say to him to make him do what she wanted. He was putty in her fingers, it was, she thought, almost too easy.

"OH, yesssssss, Mistress, I do love cum, anyone's cum that has been inside you....yesssssss, Mistress," he cried out as he furiously rubbed his cock.

Just then there was a tap at the window and a flashlight beam shone directly on his cock, his dress around his waist, his stockings down around his thighs and his panties. There was no hiding, he had been caught masturbating in the car, in the parking lot.

The police baton tapped against his window again, just as his cum spurt out of the tip of his cock and landed on his hand. He didn't know what to do now. He looked over at his Mistress with a confused look on his face.

"Put your hand in your mouth, eat your cum, and then roll down your window," she instructed.

He liked his hand, trying to get all of the gooey substance off before using the same hand to press the down button on the door handle. He tried to cover himself with his other hand but it was too late, the officer had seen it all.

He was mortified and his mind raced with nightmarish possibilities. Could this be any worse? Why had he trusted her to take care of these details? All hell was getting ready to break loose and what could she do to stop it?

"Looks like you all have come here for all the wrong reasons," the officer said when he bent down and peered into the window. His flashlight surveying the scene in the car.

"I am going to need you to get out of the car," the officer said. He struggled to make his legs work, to open the door and to stand up. His Mistress put her hand on the door to get out but the officer told her to stay put.

"I will deal with you later, right now I just want your friend here, whatever he or she is, to get out and put his hands on the car hood."

His Mistress looked at him and said, "I am so very sorry. Really, really sorry."

He thought he might throw up as he took the most manly steps he could towards the front of the car, trying to hide his face as the officer pushed him to the hood.

"Put your hands behind your back," the officer instructed him.

When he felt the cuffs go on, he knew there was going to be no easy way to get out of this, talking wouldn't work, he was fucked.

He felt the cool metal of the cuffs, and he had to laugh at the absurdity of it all. He usually loved the feel of the cuffs going on but not this time, this time it was for real.

"Spread your legs," the officer ordered him, as his feet kicked his legs apart, as much as possible, with the pantyhose band around his thighs. 


"Put your head down on the hood," the officer demanded. He did as told, closing his eyes, hoping when he opened them, this would have all been a bad dream. He felt the officer lifting up the dress and pushing his stockings and panties down to his ankles. Then he heard the unmistakable sound of a switchblade being opened. He felt the ripping of the stockings and the panties, as the officer tore them from his ankles.

"Well, that ought to make this a little easier," the officer said to him, as he pulled the ripped and ragged fabric from his feet.

"Open your mouth," the officer directed him, as he shoved the dirty, cum-covered fabric into his parted lips.

Just when he thought it couldn't get any worse, any more shameful, he felt his legs getting shoved apart by the officer's feet. He looked into the car and saw his Mistress' face. She looked horrified, and she mouthed "I am so sorry," to him as the officer's hand forced his head nose-down onto the cold metal of the car hood.

"She can't help you now, you fucking sissy boy," he whispered into his ear. "You don't want to know what we do to sissy boys, here, in this part of town, do you?"

Tears welled up, again, in his eyes and he shook his head, unable to speak with her panties in his mouth.

"Well, want it or not, I am going to take you in and that ought to teach you a lesson to not come back here dressed up as a woman. One of the ugliest women I have ever seen, too. You know, what happens to women who turn me on is I fuck'em. But since you don't have a pussy, I am going to have to think of something else," and as these words rang loudly in his ears, he felt the officer's fingers searching for his asshole.

He closed his eyes, hoping to make it all go away but there was no denying the digits exploring his ass and as the officer's first finger found its way to his manpussy, he wanted to die.

"Well, well, what have we here? Something is already in your fucking asshole. Yes, my boy, you are about the most fucked up man I have ever seen," he said as he pulled the plug, roughly, from his ass. The sound that was made as it exited was loud and horrific. There was nothing he could do but endure this humiliation.

The officer set the plug right in front of his face. "Look what I found in your asshole, boy." He didn't want to look at the plug but the officer picked up his head, his fingers wrapped in his hair and he picked up his head and all put put out his eye with the plug.

The officer placed his feet inside his now-opened stance and he roughly shoved one finger into his asshole. "Plenty of room in there, boy, maybe you'd like another?" the officer mocked him.

He tried to shake his head, no, no, begging, tears coming down his cheeks but the officer either didn't care of ignored his pleas for mercy. Another finger went in and then a third.

Frances raised his head off the hood of the car and screamed out but no sound escaped past his gag. He noticed some people leaving the restaurant and them looked over, curiously. Frances begged them with his eyes, "please save me," he seemed to be saying but once the patrons realized who it was that was in handcuffs, they were happy to know that justice was taking place in their little town.

"Nobody is going to come to your rescue," the officer said, softly whispering into his ear as his fingers roughly and painfully probed his asshole.

This was the beginning of a very, very long night.