Finding a Master

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Status: Finished  |  Genre: Gay and Lesbian  |  House: Abandoned

A outing dressing as a woman leads to so much more than he ever expected.

When I boarded the subway train all the seats were already taken. Standing wasn’t a problem, I had worn flats knowing I would be doing a lot of walking today. It was a few stops later as the train began to fill up that I began to feel nervous. Then I was bumped from behind and turned slightly to see who was behind me.

There was something about the man standing there that made me even more nervous. He was tall towering over my 5’7” frame with dark hair that had started to go gray at the temples. He gave me a sort of half smile like a smirk that gave his square jawed face a look of a man who enjoyed dominating those around him.

I quickly turned away but something in his eyes told me he knew my secret. When I felt a hand on my leg I knew it was him. I could have said something but I knew that would have lead to my secret being revealed so I lowered my head and let him caress my thigh. I told myself he wouldn’t push it further but a part of me knew he would and wanted him to.

When his hand slipped under the hem of my skirt pushing it higher I wanted to scream, but the knowledge of what would follow kept my lips sealed. I kept my head down and my lips pressed tightly together even when he caressed my ass through my panties. I finally raised my head when his finger slipped under the elastic around my leg and into my panties. I wanted to stop this, to say something before it went any further, but I couldn’t speak, my throat refused to let the words out.

I closed my eyes thinking how all my fantasies and daydreams of my first time going out as a woman never included this. I had been dressing for years but only recently had I considered leaving the privacy of my apartment, venturing out as a woman. I had imagined I would go shopping and maybe for a drink. Flirt with a man or two, but nothing more. The idea that someone would push things further, would violate me had never crossed my mind.

It was his hot breath on my neck and ear that pulled me back to reality. His deep masculine voice softly whispered one word in my ear.


That was when his finger slipped into me. I bite my lip quickly stifling the gasp that threatened to reveal us. I had used toys before, at first only a little but as I explored my fetish and the internet more and more. I was both shocked and excited when I stumbled upon my first fetish site. I was amazed at what some found arousing and what they would pay to see it. What had been a secret hobby soon grew into a second job as I spend nights and weekends online do what my followers paid me to do.

He added a second finger and I bite my lip harder as I fought to stay quiet. I was beginning to feel a pressure in my groin as his fingers probed me. I tried to fight my bodies reaction to what he was doing, but I couldn’t. When he added a third finger I came without even getting hard. It was both exciting and terrifying at the same time. This was the first time I had ever came without playing with my cock and it felt so much more intense that anything I had experienced before.

My body went limp and I just hung there as he continued. Cum continue to leak from my limp cock soaking my panties as felt shivers run through my whole body. When he finally pulled his fingers from me I felt empty and wanted to beg him to continue, but we pulled into the station.

As he slid past me looking at me with that smirk on his lips I knew I had to follow him. I joined the flow of passengers getting off, my legs still feeling weak. On the platform I spotted him headed for the stairs up to the street and hurried after him.

When I reached the street I saw him crossing the street and realized I had no clue what I would say to him. I trailed after him like some lost puppy following a stranger home as I tried to think of what to say. He didn’t seem to be in a hurry but never looked back.

I kept my eyes locked on the back of his dark gray suit jacket as we moved through the streets. He finally turned off the sidewalk in a plaza in front of a tall office building. I stopped at the edge of the plaza deciding enough was enough and I would just walk away. It was at that moment he turned and looked right at me, our eyes meeting. It was there in his eyes the knowledge that I would be there, that I would follow him.

I walked towards him as if drawn by some invisible force. I dragged my feet scared of what he would say or even do, but unable to keep from approaching him. As I got closer I dropped my head unable to meet his hard penetrating stare. I stopped in front of him, my body shaking with excitement and fear. He reached out grabbing my chin and forced my head up so our eyes meet again.

“Was what I did to you on the train so exciting that you want more faggot?”

A shiver ran down my spine when he spoke that last word that should have offended me, but it excited me. I blushed as I slowly nodded.

“Speak,” he ordered me.

“I’ve never felt anything like it sir.”


“I want more,” I added as my cheeks grow redder.

He laughed, “Wait here. Don’t move from this spot until I return.”

“How …”

He placed a finger on my lips. “You either obey or you leave. If you stay you never question me.”

I wanted to turn and leave but the look in his eyes held me in place. He smiled and turned away, but even with our eye contact broken he held me there. I felt nervous as people walked past me many giving me funny looks, but I couldn’t make myself move from that spot.

When the crowd entering the building thinned out and no more people hurried past me I realized I must look strange standing there all alone. I expected that a guard would come out to see why I was standing there, but none did. After an hour I began to wonder if he would really come back or if he had already forgotten about e standing out here.

I was ready to walk away, embarrassed for having stood there for over an hour when I saw him come out of the building. He didn’t say a work to me as he walked pass me. It took me but a moment to decide to follow him again. I hurried after him almost running to catch up with him. He moved faster now like he had some place to be and I had hurry to stay with him.

“Please slow down.”

He glanced at me and the look on his face made me regret speaking. He did slow his pace enough that I was no longer struggling to keep up. I fell in beside him, keeping my distance so we didn’t look like a couple, but just to people headed the same way.

“What do you want?”

The question caught me off guard, “What?”

“You followed me from the subway station. You stood where I told you to for way longer than most people would and now youu are following me again. So I want to know why?”

“I don’t know.”

“Yes you do, we both know what you want, but I want to hear you say it.”

He was right, I knew exactly what I was hoping would happen. I might not have wanted it when I slipped on that first pair of panties. It was there the first time I went online pretending to be a female, so small but there. The first time I turned on my camera to an online show I had wanted it even if I was too afraid to admit it even to myself.

“Say it or walk away.”

“I want to be dominated, I want to someone to control me and own me.” I blushed as the words left my mouth.

He smirked as he lead us to a park and took a seat on a bench. With a nod he indicated I should join him and I quickly did.

“I’ll give you what you want, but I require complete loyalty and obedience from you. You will do as I command without question or hesitation. You will have no secrets from me not even the tiniest detail of your life will you keep from me.”

“Yes Master.” I felt a tingle run through my whole body saying those two little words.

“You belong to me now, but if you displease me in anyway it is over.”

“Yes Master.”

He smiled but it twisted his face into a cruel and evil mask. “Go to the lady’s room over there and remove your panties.”

That was when I first noticed we were sitting by the public bathrooms in the park. I was moving towards them even as I wondered what he had in mind. I pulled off my panties once I was in the door seeing how wet they were before stuffing them into my bag.

I left the bathroom half expecting him to be gone, but he was sitting where I had left him. I walked towards him feeling scared and excited. As I got near he smirked and I knew in my gut that he was about to push me.

“Show me.”

I didn’t even look around, I reach down and lifted my skirt so he could see I obeyed. He nodded and I dropped it as he pulled me onto his lap. He grabbed my hair and kissed me, his tongue invading my mouth. I surrender to him knowing he owned me completely.

Submitted: November 24, 2021

© Copyright 2023 Gypsy Rose. All rights reserved.

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