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Dress Up

He had been begging me since we met to take him out, dressed as a woman. At 6'3", it was going to be a challenge to make him look like any kind of a lady.

She told him to lie on the bed, where she tied his arms and his legs to the bedposts. Her favorite position for him, face-up. He never knew what to expect when she did this to him. He couldn't help but get an erection, his cock always got hard when he was around her, it was involuntary, uncontrollable. He did as told, spread his arms and legs and felt pure bliss and joy as the cuffs went on. He was going into her space, his space, subspace. Heaven on earth, is how he described it.

She didn't crawl on top of him, placing her crotch or her ass over his face. She didn't move over his cock, she slapped it, telling him to relax, this wasn't about sex. She pulled a chair over to the edge of the bed and began painting his fingernails.

"Hold still," she ordered him. "I am doing this once and once only. If you mess the polish, tough shit. This is all you get."

"Yes, Mistress," he closed his eyes and enjoyed the moments, each of them. Every minute spent in her presence meant another moment of happiness for him.

The light touches of the nail polish brush on this fingernails was strange. He could just barely feel it, he was accustomed to something stronger, harsher from her. No matter, he waited for something greater. A stronger touch, another swat on his cock or a slap across his face. These were his favorites. She was expert at delivering them and she knew how much he enjoyed her touch - in any form.

"Don't move your fingers, they are perfect." He stayed very still as she blew on his hands, his fingers, one by one, moving on both sides of the bed, climbing over his body, as if he were not there, naked, erect and excited.

She moved the chair to the end of the bed and began painting his toenails, occasionally using the crop against the bottom of his feet.

"Don't fuck up the polish," she screamed as his feet flinched each time they were hit.

She blew on his toenails, alternating breath with slaps on the bridge of his feet.

"Those will take awhile to dry. I'll be back," she yelled over her shoulder as she shut the bedroom door behind her. He laid there, naked, erect, and wondering what was next. He couldn't help but wonder why she had picked now to paint his nails.

He waited and watched the sky grow dark. He didn't fall asleep, but this was a meditative place for him. It was truly the only time in his life when he could completely clear his mind, turn it all off and just live in the moment. He was responsible for no one, only responsible for providing Mistress' pleasure when she desired. That was the only reprieve he had in his life, the only break he got. She understood that and she made the most of it.

He didn't know how long it had been when she reentered the room but she looked different than she had previously. She was dressed to go out - stockings, makeup and her hair was up and back, away from her face. This was how he liked her best, the lines of her jaw and her high cheekbones clearly visible. He still couldn't quite believe what they had managed to work out between them, how well this worked for them both. He knew what he needed, he knew, in his heart, that he was a sub...he was a man who needed to serve a woman, a woman greater and stronger than himself but finding her had been a challenge. He had all but given up hope when they met. He had made a joke about spanking in one of their earlier conversations, and she had picked right up on it. At that point she had only received spanking, she had been dominated by a ruthless, selfish, arrogant man and she had shied away, not only from the D/s world but from men as a whole. He had jumped at the chance to bring it up, to discuss it, to see if he could interest her in switching sides, so to speak.

She had taken to it naturally, remarkable, really. Nothing about their relationship was simple or convenient but they both felt that it was what truly worked for them - anything else at this point would be a cheap alternative, filler, second best. They'd both had enough other relationships to know the bond they shared was real, vital, substantive.

"Are you going out, Mistress?," he asked, wondering if he might have the chance to lick her pussy or suck her nipples before she left him there, wondering when she would come back, if she would come back. She liked that, to leave him. She liked the mystery and the power that it brought. He never knew when she returned if she would want to fuck him, be fucked or have him lick her clean of another man's cum. That was an amazing experience and one that he relished. They had come so far together that she could ask nothing of him that would be too much, over the top. She was perfect for him, in every way. To the outside world, he was a macho, alpha male and she was the only person who knew what he truly needed and wanted. A woman he could worship, treat like a queen and who would not judge him. Their bond was exquisite and they both cherished it.

"Yes, I am going out and you are coming with me," she replied. He looked surprised as she had just painted his nails. Where could they be going, he wondered.

She began to untie the restraints, instructing him to get up, get moving, it was late. He did as he was told. She lead him, by his cock, into the bathroom where she sat him on top of the toilet. Then she started to wrap his hair around a very hot curling iron. He flinched unsure that she was watching what she was doing. He hated burns and she had never taken that route with him.

"Oh, don't be such a pussy! Women all over the world do this every day," she scolded him. She continued to play with his hair, curling, teasing, spraying and then the makeup bag came out.

"Close your eyes," she said as she applied the liner, the shadow and finally the mascara.

"So unfair, a man having eyelashes like that. Such a waste!," she slapped his face as she spoke these words. "Good, bring a little color to your cheeks." She followed up with some blush and then used the brush on the top of his chest, between his breasts. She also took the opportunity to squeeze and twist his nipples, causing him to cry out.

She smiled at him, kneeling in front of him, running her hands along his thighs. "Let me take a look at you," she held his face in her hands. "One kiss before the lipstick goes on," and he could feel his cock standing to attention. She noticed as well and she lifted her skirt and slid her slick pussy down onto it.

Oh, god, she felt so good, so warm, so wet. She didn't move for a long time, just stared into his eyes, smiling. "You make a beautiful woman, albeit, a woman with a hell of a cock but a woman nonetheless." She kissed him again and then her cunt muscles went to work on his cock. How she did that, he would never know. She was barely moving her body and yet, yet, her pussy was swallowing his cock whole. Causing him to shudder and spasm. She began to ride him, in earnest, and he could see that she was coming closer and closer to reaching a climax.

He began to push up against her, trying to create some friction so that he could come with her but as soon as he began to move, she stopped, slapped him hard, first across the face, then around his chest. "Do not move a fucking muscle, understand me?," she whispered into his ear.

He nodded and sat quietly as she, again, rode his cock, harder and deeper, using her muscles to drive him crazy with lust. When she came, it was unmistakable. The cries which grew louder and closer together, the gush of juices that came out of her, the flush of her cheeks and her chest. He had never known a woman to come with such abandon, with such flourish. He loved it, he lived for it.

When she recovered, she told him to purse his lips and she applied a bright red lipstick. "Go look at yourself as a woman, in the mirror. You look pretty damn good, if you ask me. I mean, you could never pass as a woman, but that will be half the fun," she smiled at him, knowing that the thought of being caught, dressed as a woman, in his own community was a fear of his.

She went into the bedroom and came back with a small g-string panty, clearly made for a woman about half his size. "Put these on," she instructed, knowing that his cock was still hard and wet from her orgasm, when she had refused to allow him to reach any sexual satisfaction.

"Now, this," she said, holding out a dress that was black and long. "Oh, wait, you'll need a bra and some fake boobies," she told him, tweaking his nipples again. "Maybe a little rouge for your nips?"

"Yes, Miss, please," he couldn't believe that he was finally getting his wish. Of course, he expected her to do this in a town where he didn't know anyone. He would never be able to hide behind the dress and the makeup. He could only hope that he wouldn't run into anyone he knew.

When dressed in a bra and panties, his erection still evident, she turned him around to look at himself in the mirror. "Pretty ugly sexy, don't you think?" she teased him.

"Yes, Mistress, as long as you are pleased that is all that matters to me," he answered, looking down. He couldn't believe how hot this was, how turned on he was.

"Raise your arms into the air," his mistress instructed and she slid the dress down over his broad shoulders and newfound breasts. The dress felt silky and soft against his skin but he waited for her instructions before looking at his reflection again.

"Put these on and your shoes are by the bed," she said, tossing him a pair of pantyhose in an extra-large size. "Lets hope these can help hide your erection. If not, I am going to have to beat it out of you. Now go put on your shoes, then come back in for another full-length glance at yourself."

The red pumps with 3" heels fit perfectly but maneuvering his large frame on them would take some getting used to but he made it into the bathroom without falling and when he looked at himself, it took a moment to believe that it was really him.

Tall, beautiful eyes, his silver hair looking like he had just stepped out of a beauty salon. The dress fit him perfectly, just the right length, covering his knees and the red shoes completed the outfit. He caught her eye in the mirror and they both began to giggle. Laughter was the thing that they always could rely on, finding the same things humorous, making jokes to alleviate some very awkward situations - laughter had been a glue for them in the beginning.

"If I didn't know you, I'd want to fuck you," she whispered into his ear. "Hell, I do know you and I can't wait to fuck you," she added, grinning from ear to ear.

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