Evolution Ch. 03

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Deeper into submissiveness- a night out.
1.5k words
4.15
26.6k
11

Part 3 of the 4 part series

Updated 09/22/2022
Created 01/16/2015
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Chapter 3. All Dressed Up and Somewhere To Go

His name was Tony, but I was allowed to call him "Master" or Sir". In public, it was "Sir". I went to His home the following week, and He introduced me to His toys, His cuffs, His Collar. He took the virginity of my ass-cunt. He tied me to the corners of His bed, and dropped molten wax over my nipples, my stomach, and then my soft, shaved, small cock and balls as I writhed in pain and ecstasy.

And he dressed me. One night, when my wife and son were out of state visiting her father, He invited me to His home. It was a Friday night, early fall, sometime in September. He'd said six, right after work. I arrived at 5:40.

He met me at the door, dressed in black leather from head to boot. "we're going out tonight." He told me. "I've your clothes laid out on my bed. Come and put them on." I smiled, starting to thank Him. "Quickly." He tersely added. I obediently followed Him up the stairs and into His bedroom. He stopped by the bed. There was a large garment bag from one of the top department stores in the city on the bed.

"Off with those." He ordered. I stripped to my shorts. "All of them." I was standing before him, naked. I held my hands at my side.

"Freshly shaved, my pet." I could feel His eyes surveying my body. "You've done well." He patted my ass, and I felt pride glowing in me.

"We'll start with these." He pulled a tiny black piece of sheer cloth from the bag and handed it to me. I unfolded the little garment, and saw that He was smiling. "Put it on."

I bent forward and donned the silky red thong panty, siding it slowly up my smooth legs until it was nestled in place, cupping my clit, and adjusted until it felt snug, right.

"Very good, my pet. Very sexy." He pulled another little folded cloth from the bag on the bed and handed it to me. A pair of black lace-top thigh high stockings. I sat on the edge of the bed and slipped into the right leg, then the left. I smoothed them, slowly, seductively, and stood, amazed by the electric feel of the stockings on my freshly shaved legs.

"Very nice, pet." He reached into the bag as I looked at the floor submissively. "This next."

He handed me a very thin, stretchy halter top to put on. I pulled it over my head, reaching through with each arm, and fitted it into place over my small, excited breasts. I snugged it down- it felt very tight, pulling up on my breasts. Looking down, I could see that it was translucent, almost transparent, over my breasts where it was pulled the tightest, and my small nipples were clearly on display. He reached up and squeezed my nipples roughly between his thumb and index finger, twisting, and it felt like my tits were caught in a vise. I remained still, though, staring at the floor, gulping for air.

"You love it, my pretty slut." He whispered, and released his grip. My nipples were red, extended, jutting out from my body, erect and excited. "This next, cunt." He handed me a pair of thin white spandex shorts. I put them on.

They were very short women's shorts, again a thin, almost transparent. The shorts stopped many inches above the lace top stockings, just covered my ass, and the panty underneath was clearly visible. His appraising eye went up and down my body, hungrily, predatorily, assessing the effect of His transformation upon me. "These are next." He reached in the bag and drew out a pair of glossy red platform shoes. "They were going to be heels. You will be wearing heels soon, but not tonight, not for the first time." He handed me the shoes. "After all, tonight you're going to be dancing."

I sat on the edge of the bed and slid the shoes on. Standing, I swooned a little, getting used to the unusual feel of the wedge, the additional height. I felt my hips and my ass thrust forward in the shoes, and my shoulders pulled back. And my breasts push put.

"Take a step, slut. Begin to walk." He ordered. I tentatively put out my right foot, and began to walk across the bedroom.

"Very good, slut. Keep going. Get used to them. You'll be wearing these a lot."

After the first few passes, I gradually became more confident. I felt how the shoes made my ass shake form side to side with each step, enjoying the feeling. Soon I was very confident that I could walk comfortably in my new shoes. I stopped in front of where he sat watching, approving.

"You're doing well, slut. Next, the bathroom." He rose and took my hand, leading me to the bath. At the makeup station, there was another small sack in front of the mirror. I sat in the chair in front of the mirror. "This is for you. I'll apply it tonight, but I fully expect you to learn to do this yourself. And quickly."

He removed an assortment of tubes, small bottles, and spray cans. "We're going to start with your eyes."

He then started to expertly make up my eyes, applying mascara, shadow, and liner until when I looked in the mirror I saw a woman's eyes looking back at me. He then applied foundation, blush, smoothers, blenders, and finally, a bright red lipstick.

"Pretty." He stepped back, positively responding to His handiwork. "Now the hair."

I had long hair anyway, the style of the time, long brown about down to my shoulders. He took a brush from the bag and began to tease my hair with it. He had spray cans ready, a pair of scissors.

"We won't need to cut, I don't think, but this will help..." He parted the hair and swept it back, applying a mousse, and started to style a new hairdo. With my fully made up face, I watched him work magic on me, my new feminine hair completing the transformation. He finished with a spray, holding the new hairdo in place.

For the final addition, he fixed a thin black leather choker around my neck. It had a small silver ring in the front. "This is your collar for tonight, my pretty slut. It will let everyone know that you are owned, and that you are Mine."

The entire transformation had taken about an hour and a half, and, insisting that I close my eyes, He led me to a full-length mirror hidden behind a closet door.

"You look very pretty, my slut." He ran a hand over my ass, and I caught my breath. "You can open your eyes now, and see the new you."

I opened my eyes, and gasped. I saw a pretty, slutty girl in the mirror. I thought that it wasn't me, I didn't recognize who in the world it was, but she turned me on. She was turning Him on too. And then I thought, that this is me, the real me, the me I always wanted to be, and I wanted to cry and my eyes began to fill.

He saw this, and he put an arm around me and said, "Don't you dare cry, my pretty slut. You'll ruin your make-up." He kissed me very forcefully, taking my breath away and driving any tears away. His tongue rammed into my mouth, and I began immediately to suck on it, swirling my own tongue around it, taking his tongue as deep into my mouth as it would go. His hands cupped my ass, squeezing, tight, and I thrust my hips and crotch into him.

We broke the clinch after a few minutes. He took my chin in between his fingers, looking into my eyes. "We're going out in a few minutes." He said, "We'll continue this later." I was panting, and heard His own breathing coming in heavy, deep gulps. He led me downstairs, and sat me on the large sectional ivory couch which took up a center portion of the large living area. "I'm going to mix us a drink before we go."

He went to a bar against the wall and pulled a green bottle from a small wine cooler. He opened the bottle and half-filled two glasses with white wine. Handing me mine, he said, "Don't drink yet. I have something else for you." He pulled a small manila packet from a side table by the couch.. He pulled a small blue and white capsule from the packet, opened the capsule and dropped the contents into my glass. "This is going to make you very relaxed, very eager to be physical. Any inhibitions you might have will be erased, so that you may have a great time tonight. It will please Me greatly to control you, to have you under my total command, and this will make you compelled to absolutely obey at all times."

I swirled the drug into my drink until the powder has dissolved. "Thank You, Master." I responded, and we tapped glasses.

"To our night together." He toasted, and I began to sip the delicious drink. "Drink up, and we'll be gone." I tilted the glass, emptying it, and I noticed he had only sipped his. With that, he led me to the car and we left.

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AnonymousAnonymousalmost 3 years ago
Dresser

I started cross dressing for my own in joyment and self sex.Soon dildos just did not do it for me.So i went on line i put pictures of my self fully made up and dressed.It was not long before men wanted to meet up with me.I picked one nice looking older man and went to his place.We talked for a long time about what i wanted him to do to me and what i would to him.For the first time i found my self down on my knees hands cuffed behind my back collar and leash around my neck.I could not stop him from slidding his hard down my throat.With his hands holding my head he fucked my mouth.He then started to fuck me hard in my ass.Just as he was going to cum he put his cock back in my mouth filling with his cum.

hindsight2020hindsight2020about 9 years ago
Stop!

Take some time to figure out what story you want to tell. It started well, but it is all over the place now.

ffemt53ffemt53about 9 years ago
Still Confussed

If you want to confuse your readers, you're doing a good job of it. What started out as nice story really took a confusing turn.

Your 1st Chapter started out believable enough.

Your second chapter confused every one with this BMSD turn. Forgetting everything from the 1st chapter but he all of a sudden has children.

Now his wife and children are leaving to go out and he is meeting with his master who in the 1st chapter was his wife but changed to a man he meet in an adult book store, who was the first person to dress him up.

jamieengland1, you need to come up with a time line for this person and write it in that order. Stop jumping all around.

AnonymousAnonymousabout 9 years ago

Less less less. These chapters are all over the places. Are you just posting random chapters?

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