Dress Up Ch. 02

She told him to follow her as they walked to the car. She held the passenger door open for him, telling him to get into the car. She made it clear that she was in charge, that she would be driving. He always drove, it was part of their routine. He was the alpha male, the guy in charge, to the outside world but not tonight. Tonight, she was the alpha female.

She took the road towards the highway and he breathed a sigh of relief.

"We are not coming back to the house later, I have a treat for you tonight," she told him.

"Don't worry about anyone you know recognizing you. I want you to relax, enjoy the experience, be the woman you've always wanted to be. Leave it all up to me, trust me, put your faith in what I can do for you. Deal?"

He nodded, exuberant in the possibilities and in what she could bring out in him.

"How do you feel? Comfortable? How are your clothes? Is there anything else that might help you feel like more of a woman?"

He shook his head. He was trying to revel in the moments, these moments of authenticity.

"How is the plug? The one I slipped into your anxious and ready asshole earlier? Is it hurting you or does the stretching feel nice?"

"It is all fantastic, thank you, Mistress," he answered. "I can't think of anything that could make me happier. I am so grateful to you."

"Don't get all relaxed and grateful yet. This is only the beginning of our evening. I have things planned that I won't tell you about yet because I worry that you might jump from the car. It's going to be a bumpy ride - a magical, exciting, mind-bending ride," she smiled as she spoke the last sentence and reached over to rub his cock. It was exciting to feel his cock under the silk dress, the hose, the panties and his cock exhibited the same excitement.

Her hand came down on his cock as swiftly as her reach over to rub it.

"Did I tell you that you could get hard?" she demanded.

"No, Mistress, you did not. I am sorry," he said, looking down at his very erect member.

"Does a woman have a bulge in her panties?" she went on.

"No, Mistress," he answered.

"Well, then, you best get rid of that bulge in your dress before we arrive at the restaurant" and with this, another few slaps to his cock. She quickly pulled onto the side of the road, put the car in park, and moved on top of him, straddling his cock, rubbing her pussy against him. She kissed him, on the mouth, lipstick to lipstick, smearing his. She pulled her face back and looked at him, his beautiful eyes, mascara-laden eyelashes, and blush.

"My, my, you do make a pretty girl," she announced. She kissed him hard again, pushing her tongue past his lips, searching, taking control, rubbing his cock into her crotch. One hand wrapped around his jaw while the other struck his cheek, causing his face to turn red from the strikes.

"I thought I told you not to get hard," with each syllable out of her mouth, there was another blow to his face.

She lifted her body off of his and looked down at the bulge in his little black dress.

"What the fuck do you call that," she asked, squeezing his cock as hard as she could. His mouth opened but no sound came out, he was paralyzed by the pain.

"Fucking answer me when I speak to you," she demanded. "NOW!"

"I am sorry, Mistress, I cannot help it," he whimpered.

"You are such a fucking pussy, you piece of shit. I always knew you were a pussy and this just proves it. Pull it together and get rid of that erection," she instructed. "You make me sick," she said, as she let go off his cock.

She went back to her side of the car and opened her legs. One leg behind his seat and the other on his lap. Her back was against the driver's door and he could see that she was not wearing any panties. Her hand reached under her dress and she began to play with her pussy. He could smell her scent and that always drove him crazy. He couldn't believe what was happening. Headlights were shining into the car but no one stopped, no one seem to see what was going on in this car, parked on the side of the road.

"Pull out your cock and play with it, now, here. We need to take care of this issue, this problem, this bulge in your dress," she whispered.

He unhooked his seatbelt and lifted the dress up around his waist. He lowered the stockings and the panties and did as she told him to do. He began to stroke his cock, while watching her. He loved watching her masturbate. Nothing turned him on more than her hands in her cunt.

"Lick my fingers clean," she said as she held out her drenched fingers for him to suck on. "That's a good little pussy man," she mocked. He licked her hand, between her fingers, sucking on the tips, so as not to miss every drop of his Mistress' juices.

She was glorious, perfect in her ability to tell him what he needed, what he wanted. He adored her, as he had no one else.

He was rubbing his cock, hoping to make cum so that he could walk into the restaurant without this bulge in his dress. He wanted nothing more than to walk and talk and act like a woman. This had been his dream, his fantasy, for as long as he could remember. He never dreamt that his Mistress would actually let him live out his desires, his wants. This was an amazing night already.

"That's it, pussyman, rub your pitiful little cock, make yourself cum but don't get any of it on your black dress or you will have to walk around with a cum stain on it and don't expect me to clean it up or to suck you off. It's time you learned how to masturbate neatly, like a woman does," she spoke softly, almost as if she was pitying him and this only turned him on more.

His body began to convulse, watching her fingers as she expertly pleased herself, feeling the stockings tight around his thighs, imagining what he must look like to his Mistress, it was almost too much to bear. He closed his eyes and he came. He came harder than ever and his cum spurt up and towards his chest, leaving a big messy glob between his "breasts."

His hands were wet and as he tried to clean up the mess off of his dress, he only made it worse, smearing it, making the stain larger.

She began to giggle and told him that he would have to ride the rest of the way to the restaurant like that, with his panties around his thighs and his dress hiked up around his waist.

"Better hope we get there safely, pussyman, because you wouldn't want an officer finding you like this, would you?" she teased.

He was still seeing stars from his ejaculation. He'd come so quickly, so hard, that he didn't have time to collect his thoughts before she had gathered herself back together and started driving again. She began driving very fast, weaving in and out of traffic, and the honks and hand gestures were frequent on their drive to the out-of-the-way restaurant. She did make a point of slowing down whenever they were beside a truck or a delivery van. She gave everyone on the highway a chance to see his shriveled cock hanging out of his panties, and all they had to do was look down into the passenger side of her car to see the pitiful man's even-more-pitiful cock. They received lots of honks and hollers, and he could feel the shame rising up in his face, causing him to blush.

Finally they arrived at the restaurant. It was a little Italian place, and it looked very homey, like a neighborhood joint. She got out of the car, quickly, and she leaned in to tell him to pull up his hose and his panties and to come in when he thought he could look like a lady.

She asked for a booth and told the maitre d' that there would be one more joining her. "A big girl," was how she put it to the host.

She sat down in the booth, ordered a drink and began to look over the menu. The host brought him towards her booth and she acted as though they had not driven over together. She greeted him/her enthusiastically and she ignored the looks of the host, the smirk.

"Oh, honey, sit here, next to me," she stood up and insisted that he/she sit on the inside of the booth.

"I will order for you," she told him as they began to look over the menus.

The waitress came over and had a hard time not staring at him. It was so apparent that he was not a she.

"My friend, here, will have a Shirley Temple," his Mistress told the waitress.

The waitress almost laughed out loud but the look she received from his Mistress was scathing, so the waitress didn't let on that it was obvious he was a she.

When the Shirley Temple arrived, she gave the waitress their orders for dinner. He did not speak, he did not even look up at the waitress. This was much more difficult than he had anticipated and he was grateful that his Mistress was handling everything so beautifully.

"Just relax, babe, everything will be okay. Enjoy being a woman, you look fantastic and I would hope that you feel fantastic...I mean, aside from the huge cum stain on your dress, you look amazing," she whispered into his ear.

He had completely forgotten about the cum stain and he began to blush, yet again. He had been so concerned with getting his cock back into the stockings and getting himself pulled together, as a woman, that he forgot that his dress was covered in cum. No wonder the waitress and the maitre d' were laughing at him. This was all more difficult than he imagined it would be, in his fantasy.

"I think we should head into the ladies' room and get you cleaned up," she finished. "Oh, but before we do that, I want you to make your cock hard again because I need to be fucked. I got pretty excited back there in the car, when you were stroking your pathetic little cock. You know how much I love it when you suck on my fingers, wrapping your tongue around each one, the way that I have taught you to do. Your tongue is so talented, the way that it fucks my pussy and pleases my asshole. I know you long to do it now, to stick your tongue in all of my holes, don't you? You want to tongue-fuck me now, don't you, babe? You want to taste me, all of my juices, my cunt, my asshole...you want to service me, don't you?" she continued to say, softly, into his ear.

She reached down to his lap where she knew that she would find him hard again and she was right. His cock was engorged, and he was ready to please her in whatever way he could, whatever way she would allow him to pleasure her.

"I am going to head into the ladies' room and I want you to follow me in 60 seconds. When I stand up, begin counting and then walk over, very slowly, to the loo. I don't want you to try to cover your erection or your cum-stained dress, in any way, and if I find out that you have not done as I have instructed, be sure that there will be hell to pay," she warned.

Before he had a chance to plead for another way, she had excused herself and began making her way to the bathroom. He felt as if every eye in the restaurant was on him. He looked like exactly what he was - a man dressed up as a woman, a 6'3", 220 lb man dressed up as a lady. He knew that he couldn't pass as such and this made it all the more difficult to slide out of the booth and to walk to the ladies' room. His erection was obvious and he was concerned that he would get called out by the management for indecent exposure.

He felt even more immense shame at having to walk into the ladies' bathroom, as it was so obvious that he was not a woman but he did as he was told, not wanting to suffer the consequences of disobeying his Mistress.

As he walked into the bathroom, he heard the door lock behind him and she put her hands on his head, forcing him to kneel on the floor. She pressed his face into her pussy and told him to lick her until she came. He began to lap up her juices, trying very hard to please her, to make her cum but each time she came close and he could feel her body begin to quiver, she would pull his head away.

He knew how long they had been inside the loo and he was beginning to worry about the other patrons. More than once he heard a knock on the door and was surprised to her his Mistress yell out that she would be right out. "I'm coming," she would say, and then she would begin to laugh. This happened at least three times and it was hard for him to focus on his job at hand.

She walked away from his mouth, his lips, his tongue and she walked towards the sink in the bathroom. She placed her hands on the sides of the sink and she flipped her dress up around her waist. Her spread her legs wide apart and she wiggled her perfect ass towards him.

"Crawl over here, without ripping your stockings, pussyman, and suck my asshole," she said as she pulled the cheeks of her ass apart. "Make me cum and do it fast," she finished up before staring at him via the reflection in the mirror.

He quickly crawled on the hard, dirty bathroom floor over to her ass and he stuck his tongue deep inside her asshole. He knew how much she loved his tongue in her back-hole and he was eager to make her cum but even more than that, he loved the feel of his nose in her crack, the taste of her ass, the smell of it all. It was, perhaps, when and where he was happiest, serving his Mistress.

His tongue was growing sore but he would never dream of taking a break, he had learned the hard way that when she told him to do something, he best do it. Her consequences were swift and severe. He never knew what they would be, as she was by far, the most creative mistress he had ever served but she never failed to make him recall, for days afterwards, where he had failed her. He could never forget the board torture that she performed on his cock the time he had forgotten to return her phone call. He wasn't sure that his cock or his psyche would ever recover but he always called her at their appointed time after that. He could still feel the two unfinished pieces of plywood being slipped onto his cock and the screws that she used to slowly and methodically bring the two boards closer and closer and closer together. The pain was so sweet and so harsh that he couldn't help but get an erection, which only made it that much more painful. No, to this day, years later, he calls her when he is told to call her. He does whatever she instructs. He understands how difficult it is to be an excellent mistress, to put in the time and the energy, necessary, to properly train him.

It's not an easy thing to do and she has made that perfectly clear to him each time he has fallen down on the job of being her slave. She tells him, usually with a crop or a switch in hand, how hard she has to work at being the perfect mistress and with each statement, she delivers a blow to his bare ass that brings him to the verge of passing out - with pain and with pleasure. He knows how difficult he was to train, what walls had to come down and how hard he fought against her every move - "two steps forward, three steps back" she used to say to him before he could admit to himself who he was and why, before he could completely and totally turn his sorry self over to her so that she could make him a better man and the man that she needed.

His tongue was working wildly, circling, wetting, probing her beautiful asshole and her hips were reacting to his care. He asked her, politely, if he could use his hands as well and she screamed out an enthusiastic "Yes, god, just do what you have to do to make me cum!"

His hands moved around her hips and while one hand pulled her ass closer to his face, making it easier for his tongue to stay fully in her asshole, sucking and slurping as hard as he could, his other hand went inside her sopping wet pussy. He found her g-spot, that spongey area that was unmistakable in her.

He could tell by the movement of her ass that he had hit home. She reached back, wrapped her hands in his hair and forced his face farther up the crack of her ass. She was close, this much he knew, and when she stopped moving, when her hand went limp on the back of his head, he knew that response. He began to lick as fast and furiously as he could. Her juices were everywhere and he didn't need to be told to clean her up, he knew that was his job. He could rest assured that no matter who she fucked, how she came, whether by her fingers, her vibrator, his cock, his mouth or another man's cock, his job was always and always would be to clean her up.

She was trying to steady herself against the sink as he spread her ass cheeks apart and lapped up all of her juices that he could. There wasn't a taste in the world he loved as much as her juices. The taste was intoxicating and mind-altering to him. He truly could turn into a different person, the real person that he was inside, when in her presence, when serving her.

"Fuck me," she said, as he was just finishing his clean-up duties. "Fuck me now, from behind," she told him, as she readied herself with her hands, again, on the sink. He stood up, quickly, at the ready, always, and he lifted up his dress and realized how hot they both looked. Their reflections were in the mirror over the sink and their eyes met. What was said between them, at that point, without any words, was more powerful than anything they could put into words. Her love for him, her appreciation of him, her power to help him be who he truly was, all of that was evident in her eyes. His devotion to her, his true, inner desire to please her in whatever way she needed, his love and adoration for her was apparent to her when he looked at her the way he did at that moment.

He held his dress up around his hips, he worked his panty-hose down and then the panties. He looked so beautiful to her and she couldn't wait to feel his hard cock in her cunt. He smiled at her as he slowly guided his cock into her waiting, hot pussy. She enveloped him.

It was here where he felt most at home. She was his home, as much as he might want to deny it, he knew this is where he could live, forever. This was his sustenance, his love, his life-force. It was all here, between her legs, between her ears, in her soul. She knew him like no one else ever had and this was, truly, the biggest turn on imaginable. Nothing, nothing could compare to this piece of heaven in his hands, right now.

After his cock was where it should be, in that place that made him happiest, where it belonged, his hands grabbing her hips, exactly as she had trained him to do, he began to slide himself in and out of her, slowly at first and then building up the speed, as he recognized her movements. He knew her body so well, he knew each quiver, each breath, what each sound meant. Her body always spoke to him - either through her gifts and kindnesses or through her punishments, which he knew, in his heart, were her gifts to him as well.

His hand went to her mouth where she sucked on his thumb, wetting it, lubricating it. He knew just what to do and his thumb pushed its way into her asshole. This always made her a little crazy. Her hips were pushing back against his cock, grinding, humping, mad with desire. The farther his thumb made it up her ass, the deeper she wanted his cock in her cunt.

Again, her body froze up and then her whole body began to shake. He knew her orgasms by heart, and she would next begin to ooze her juices down her legs, combined with his cum, if she allowed him to meet to let go but he didn't dare without her okay.

He was so close, he wasn't sure he could hold back but he did. Her face fell against the mirror and she told him to pull out and start cleaning her up, again. And he hit his knees in grateful servitude.

After he had licked and sucked all of her juices, again, he stood up, looked into the mirror and saw that his face, his lipstick, his hair, it was all a mess. But not his Mistress, she looked fresh, relaxed, put together. She smoothed out her dress, pushed her hair behind her ears, and put her hand on the doorknob.

"Come out when you get yourself back together," she smiled at him, grabbing his still-hard cock and kissing him. "You really are a mess, babe, see what you can do before you come back to the table."