Dressing to Please Ch. 01

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Discovering my submissive side and need to please.
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I was at a friend's party dressed in a short, tight skirt with a low cut blouse and four inch heels overtop a light green lace garter belt, bra and sheer panty set with sheer black nylons. No one minded as there were a lot of other transvestites there as well! About an hour after I got there a man came in that caught my eye. I don't know what it was about him or why I stared at him until he noticed and I blushed furiously as he smiled smugly.

About thirty minutes later he looked at me and indicated the door then held up five fingers. He hadn't said a word to me or even looked at me during that time but now he wanted me to leave with him? I wasn't going to go, I wasn't, yet five minutes later I was standing by the door waiting for him. He didn't leave for another ten minutes. Just left me standing there holding my coat and blushing whenever he looked my way and indicated that I should stay there.

When he finally led me out he smirked at me as I meekly followed him and wondered why I was. What was it about him that made my knees weak and my heart race? Why did I find myself so weak and helpless to stop myself from doing what he wanted me to? I wasn't a wimp but a strong determined transvestite person with a will of my own.

"You look very nice and I made a bet with myself that you are the type of girl that wears a garter belt and nylons. You are aren't you? Aren't you?"

I nodded.

"Okay then show me."

I couldn't believe what he was saying! there was no way I was going to. I'd slap his face if my hands weren't so busy lifting my skirt up high enough to show him my garter belt. My hands were what? What the hell was I doing?

"Very nice Miss. Very nice indeed."

The elevator dinged as it reached the parking level and he walked to his car casually leaving me there until I shook my head, pulled down my skirt and quickly followed him to it.

"I made another bet with myself that you would take off your skirt and blouse before you got into my car. You will won't you? You'll do that for me, I know you will."

Again my mind told me there was no way I'd do it; loudly it told me! Not that I didn't enjoy exhibitionism or displaying my body in lingerie' but there were limits, weren't there? He just stood there and watched with that damned smirk on his face as I removed my skirt and blouse and stood there stupidly holding them.

"Thank you, Miss. I hate losing bets, even to myself."

He unlocked the doors and we got in. It was a long slow drive to his place and he turned on the interior lights every time a car passed us so they could see me more clearly. I blushed furiously the whole time and found myself trembling, my heart racing, my breathing short and quick, my pulse pounding, and feeling incredibly excited.

He pulled into a parking lot and smiled as he looked over at me.

"Quite obviously you enjoyed that a lot. Don't try and tell me you didn't. The way your nipples are sticking out so swollen and hard, the way your breathing, the wetness across the front of your panties would make you a liar. Now for my final bet I am absolutely sure that you are going to hand me your things to carry up, along with your bra and, if you're brave enough, your panties as well! You want to do that for me, don't you? You won't let me down will you?"

His look was enough to overcome any resistance I had it seemed as I folded my outerwear inside my coat and calmly unhooked my bra. My small breasts gleamed whitely in the interior lights against the deep tan of the rest of me. I felt so exposed and so excited with my nipples throbbing and aching to be touched by him. I couldn't let him down even if the bet was with himself. I hooked my thumbs into the waistband of my panties and lifted my bottom up to slide them down and over my heels.

My clit gleamed both from the stark whiteness and the wetness of the precum covering it. I felt it twitch and my body shuddered in near orgasm as he just smirked again. Getting out he came around to open my door and helped me out then led the way across the parking lot and into the building. My knees were wobbly and my mind kept asking itself if I was insane. I had to be to be doing this didn't I? I didn't even know his name and here I was meekly following him in a garter belt, nylons and heels across the parking lot, the lobby of the building and into the elevator to ride up to his apartment.

"Just so you know there are cameras in the entrance, the lobby and there's one above you that can be watched from any apartment in this building at any time. Quite a few people like to watch them all the time so I'm sure at least a few people would have seen and admired your state of dress. Do you like that idea? I think you do! I think you want to show people just how much you like dressing up like a girl and how far you're willing to go to do it."

I focused on that thought and tried to shake myself free of the doubts about my sanity or why I was doing everything he wanted! Yes I did do my best to be as feminine as possible. Everything from shaving myself as smooth as possible below my neck to arching my eyebrows and shaping and polishing my nails! I used makeup and dyed my hair a bright orangey red every weekend before dying it back to light brown on Sunday for work. I did my utmost to be as feminine as possible and was justly proud of my efforts.

The bell dinged as we reached his floor and I followed him down the hall and into his apartment. He tossed my things unto a chair and sat down then told me to make him a cup of tea. I searched thru the cupboards and found the things then used a small tray I saw to bring him the tea, cream and sugar.

He liked that and the fact that after I knelt at the side of his chair and folded my hands in my lap. He sipped his tea and watched me tom see if I'd fidget and smiled when I didn't. Getting up he looked at his watch and said it was time for bed and I should go for the night.

Indicating my things he said he'd be pleased if I'd go back down the way I was. He wanted to watch me on his TV. Once I was outside I could get dressed if I wanted and he'd call a taxi to take me home. Tomorrow he had a small group dropping over for a poker game and he hoped I'd find my way back here to serve them drinks and snacks he'd have ready. He like it if I could arrive here at two o'clock and be dressed as much like a maid as I could.

I nodded, knowing I'd be here dressed like he wanted then picked up my things and carried them out. The walk down the hall and the ride down in the elevator seem to take forever. I was still somewhat dazed and never hesitated till I got to the lobby. I had to force myself to walk across it but knowing he was watching was enough to make me do it before I stepped into my skirt and did up my blouse just as the taxi arrived.

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3 Comments
DaveXX80DaveXX80about 8 years ago

Definitely intriguing! I can envision myself in this fantasy and doing what he says. Hopefully we will get to read the next chapter!

bluesky496bluesky496about 8 years ago

i like where this is going , i would love to read more ,it is very much how i like to be treated and i know i am going to enjoy the next chapter so please hurry and write it .

sublockedsublockedabout 8 years ago
Interesting

A fellow wild rose resident.

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