A Dominatrix Diary

by A Dominatrix

 

Part 6

 

The Rules. Read them over twice, sissy.

Rule #1: You are my sissy slut. When you read anything I have written you will be wearing at least one article of explicitly feminine attire, the more the better. In addition, anytime you read an entry from my diary(this goes for past entries as well), you will have a lipstick on hand and you will have coated your sissy nipples with a rich, seductive red. Stop reading now, get your lipstick and go paint your nipples.

Rule #2: You may only have an orgasm three times in any calendar week and at least 48 hours must pass between ejaculations.

Rule #3 You will stroke that sissy ‘clit’ to maximum excitement at every available moment (in the rest room, in bed at night, in the car, etc.), you must be constantly planning your next opportunity to masturbate while you remind yourself what a sissy you really are. You will judge your success by the steady flow of precum into your panties. I want you to be perpetually wet. BUT . . . no ejaculation, except on schedule!

Rule #4: If you cum while reading a chapter, the next time you turn to that chapter you must start again, from the beginning.

Rule #5: Each chapter will be introduced with a specific task for you to perform before you are allowed to start reading the chapter. Any time you reread the chapter, the task must be performed again.

The Task

Today is your day to be penetrated sissy. Get your dildo, your vibrator, your butt plug or any other cock-like object. Suck it and lick it while you read the next entry (entry?). If you have experience, I want that thing stuffed up your sissy ‘cunt’. Take your lipstick (I know you have it with you) and put a fresh coat on your lips. All tricked out? Now read.

(Note from A Dominatrix: The following was written in the third person after an extensive and interesting debriefing of the male who is portrayed here.)

Don’t Disappoint Me

He hadn’t wanted to go to the Sunday afternoon gathering but his wife had insisted. They’d only been married about a year and already there was a feeling that they were losing touch with each other, so he went, more out of a sense of duty than anything else. He wasn’t much into socializing and once they arrived he quickly lost track of his wife and was left alone, eating appetizers. Then he saw Her.

She was sitting in a large easy chair surrounded by other women and She was beautiful. Long sexy legs, thick waves of brown hair, dressed to kill and a look of confident intelligence in her dark eyes. He had seen Her from across the room and he couldn’t stop staring. He watched Her as she got up and moved through the room, smoothly, with the grace of a tigress. He watched Her as she stopped and talked to other guests, occasionally laughing at some comment. He watched Her as She returned to her chair, looking like a queen on her throne.

He never imagined that She would even notice him but then, quite deliberately, She turned her head in his direction, locked eyes with him and with a slight motion of Her head, beckoned him to Her side. There was no question of resisting, he walked over to Her and stood in the place She had indicated. He trembled slightly and searched for something to say.

He stood there for the rest of the afternoon and into the evening, saying nothing, without further acknowledgment from Her. He tried to look casual but only felt silly. He thought about walking away but couldn’t find the strength to do so. He listened to Her conversation with the other women but he couldn’t pick up the thread. Finally, She arose and made ready to leave. Again, She looked at him and with the same nod of Her head directed him to follow Her. He walked behind Her and when they got to the door She looked at him again.

‘You’ve done well,’ She said, ‘give me your phone number and I will call you tomorrow morning.’ He searched frantically for a pen and piece of paper and just before She walked out, he handed Her a scrap with his number on it.

The next morning his wife went to her job at the usual time but he called in sick. Finally, at 11:45 the phone rang and it was Her. ‘Very good again,’ She said, when he answered. ‘Tell me your address and I will send you a package today with instructions.’ He told Her his address, She said goodbye and hung up.

The next day he left work early to make sure that he got to the mail before his wife. No package. He did that same the following day with the same result. On the third day the package arrived. He tore it open, saw the contents and the note attached and he almost broke down. The box contained a pink envelope and a few articles of clothing; a bra, panties, a skimpy pink top, a pair of very short hot pants, and gold pumps with five inch heels. Hands shaking, he broke open the envelope and read the note:

On the 27^th of this month you will walk into the Crestview Mall, at the south entrance at 11:00 A.M. sharp. You will be wearing all the articles in this package and no male clothing. You will walk up and down the main concourse of the mall for one hour. If you please me, several friends of mine and I will meet you at Victoria’s Secret precisely at noon. You are encouraged to accessorize yourself and your ensemble in an appropriate manner. You are encouraged to comport yourself gracefully (hint: walking in the shoes will require practice).

You know what I want, don’t disappoint me.

He read the note again and again with the items spread out before him, then he went to look at the calendar, the 27^th was sixteen days away. His wife was going to be home soon, he gathered everything up and hid it.

The next day, Friday, he called in sick again, his boss was impatient but he hardly noticed. As soon as his wife left their apartment, he took the package from its hiding place and spread the contents out once again while he read the note, for perhaps the twentieth time. Again, the strange thrill which had come over him when the package arrived stirred within him. He reached into his pants and felt the inexorable ooze of pre-ejaculate soaking him. Slowly, almost without volition, he began to undress and as his pants slipped to the floor his penis sprang forth, utterly erect. Then, with a shudder as his excitement mounted, he tried on the items that had been sent to him. The panties and the hot pants were very tight yet he could tell somehow that the fit was right. He put on the shoes, which also seemed to be the right size and stood up, wobbling mightily. He tried to take a step and immediately had to catch himself on a chair. Yes, he would need practice.

Exhausted after only a few tries with the shoes he sat down and picked up the bra. A bra! He put it on as his erection strained against the hot pants. The cups were very large and the material hung limply on his flat chest. He put on the pink top. It was sleeveless and cut short so that his midriff was bare but, like the bra, it also had excess material in the front so that it hung formlessly as well.

Wearing all the contents of the package now, he staggered over to the full length mirror and looked at himself. He looked ridiculous, a man wearing the outfit of a teenage girl. Hairy, lumpish and clumsy, the last words in the note echoed in his brain: ‘You know what I want, don’t disappoint me.’

He spent the entire day practicing walking in the gold pumps. By the time his wife came in the door he was completely worn out but he had at least learned how to get across the room, in artless fashion, without falling over. He was completely distracted over the weekend trying to think of ways to get some privacy from his wife so that he could put on the outfit and continue to practice. He kept thinking that he should be doing more so as not to disappoint Her. How should he accessorize himself?

On Monday, at work, he began to surf the Internet. Unable to believe each step he was taking, he typed the words ‘cross dressing’ and ‘transvestite’ into various search engines. Much of what he found left him dizzy with the sense that this was the path down which he was being inexorably drawn. Hair removal, make-up, lingerie and much more, in great detail was laid out before him and he came to realize what he must do. This was what She wanted. Late that afternoon he was confronted by his boss about missing work and unauthorized Internet use. He was given a warning but he barely heard it.

That evening, after he and his wife had gone to bed, he got up surreptitiously, put on the gold pumps and began practicing his walk back and forth across the living room. Forty five minutes later the lights snapped on and his wife was standing there, asking him what the hell was going on. He couldn’t answer, she made a phone call, packed a few things and left. The next day she moved out entirely. He found he didn’t care, except to think that now he could devote more time to his preparations.

Events happened quickly now. He went to a pharmacy and bought make-up. Lipstick, foundation, mascara, eyeliner and blush all came home with him. Each afternoon after work he rushed back to the apartment, shaved his face and applied the make-up according to instructions he found on the ‘Net. Then he would dress in the clothes she had sent him and practice walking in the pumps. He thought about shaving his legs and the rest of his body but realized that it would be impossible to do a good job without help. He made an appointment with a local salon for a full body wax.

On the day of his appointment he was in a daze. When he walked in the door he thought he would be nervous and humiliated and indeed the salon owner smiled patronizingly as she prepped him for the all-day process. Humiliated he was, but his main feeling was an anxious excitement to see how his body would look after all the hair was removed. The waxing completed, he looked at the finished product in the mirror and nearly fainted. His body almost looked like that of a woman’s and the feeling of bareness was glorious. On his way home he stopped at a small wig shop and bought a long red wig.

Once again that afternoon he put on the outfit and the make-up. He was getting better and better at drawing a smooth even line with the eyeliner. He was able to carve an elegant shape across his mouth with the lipstick and now, placing the wig on his head, he surveyed himself in the mirror with his new hairless body. What he saw was a sexy woman with one glaring need. Almost without thought, he ran to his computer and, over the Internet, he purchased the highest quality, most expensive silicone breast forms available to be sent out via overnight delivery. He knew by now that the bra She had sent was a D-cup and that it must be filled, lest She be disappointed. On the afternoon of the 26^th, he returned to the salon and had extra long, blood red, acrylic nails applied to his fingertips.

The next day, at exactly 11:00, a tall, attractive redhead, scantily clad, with very large bouncing breasts, walked in the south entrance of the Crestview Mall. Her step was confident and seductive. She carried a small purse on a strap over her shoulder and smirked knowingly at the men who stared at her as she paraded down the main concourse. For the next hour she window shopped, occasionally taking a lipstick and small mirror out of her purse and refreshing her lip color as she posed elegantly in her five inch heels. At noon, she walked over to Victoria’s Secret and met several other good looking women. As she sweetly turned around, presenting herself for approval, she was greeted by applause and hugs from all the women.

( A word of warning from A Dominatrix: The task at the beginning of Part 7 will require you to have high heels at the ready. Don’t disappoint me.)

 

 

 

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© 2002 by A Dominatrix. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.