This story is fictional. You know the drill: If you are underaged or don´t like TG stories don´t bother reading any further. All rights are reserved. If somebody wants to publish this story somewhere else please contact me first.
Jasmin wears the pants
by Greta
I had just arrived in New York for a week long visit. After I checked in my Hotel I left in order to grab a bite. I walked the streets not really knowing where I was heading and finally ended up at a Bar. There were quite a few people, mostly men talking, drinking beer and snacking on all kind of different foods. The tables were empty except one. A blonde and elegant looking woman was sitting there, all by herself. I looked at her for a moment and on impulse I walked to her table and asked whether I could sit with her. She looked me up and down and simply nodded.
"Hi, I am Gary. Do they have good food here? Sorry for intruding. I don`t know what came over me but somehow this seemed to be the only place to sit down. I am surprised none of the men is sitting with you."
Her smile was completely captivating. "Oh, they know they can`t be with me except they fulfill my wishes", she answered. "You know I wear the pants and anybody who wants to be with me has to wear the opposite and has to accept this. They don´t, would you?"
"What do you mean by opposite?"
She looked closer at me with her capturing green eyes.
"Easy, if I wear pants what do you think I mean with opposite? Skirts, maybe dresses. Definetely not pants like me. Understood?"
I gulped.
"Do you want to tell me you want to make the men wear skirts?"
"No, I don´t want to make the men wear skirts. I want to make my man wear a skirt while I wear the pants. You got it?"
I must have turned red because I felt hot for a moment. She raised an eyebrow. I opened my mouth to speak but nothing came out. My second try was more successful. She laughed easily.
"So did these men ask you to be with you.?"
"Hahaha. Yes, all of them, but nobody took on my offert."
"Oh wow, I am stunned. I have never heard anything like that before. No wonder why nobody sits with you."
She laughed again. "But you do."
"Err, yes, because I didn ´t know about this offert of yours before but you are so intriguing I´d like to have dinner while sitting at your table. May I?"
"Of course. Tonight I make an exception."
"Thank you. By the way, may I ask your name?"
"I am Jasmin. You aren´t from here, aren´t you?"
"No, I am just visiting for a week having arrived only a while ago and wanted to grab some food. You never answered whether the food was good."
"Yes, you´ll certainly enjoy it."
"I am sorry for asking again but this is so intriguing. What would you do if a man said yes?"
"You mean, me wearing the pants and him in skirts?"
I nodded.
"Well, I would make him my girl. That simple."
"Your girl? What does that mean?".
"Oh, you are really curious. Do you want to be a girl?"
"No, I mean, I was just curious about this whole thing."
"I see, you like to fantasize. Ok, I let you in. Just because you are from out of town. Like I said I wear the pants and I will turn my macho man slowly and graudally into my girl. This implies the whole process."
"Which process?"
"You know like getting rid of your body hair for example. If it were you for example I´d go very soon with you to have a haircut and you definetely know it will not be to the barber. You have beautiful long hair. Would you do me a favor? You know I am telling you all this and I would like something in return."
"What do you mean?"
"I would like to take out a scrunchy from my bag and put your hair up in a ponytail."
I flushed, my face turned totally red. "I, I, I can´t. What would all the men think of me?"
"Well, then our time together is over if you can´t do me this little favor. Nobody knows you and nobody pays any attention to us."
She gazed at me and I couldn´t hold it and looked down. I whispered. "Ok."
She had me and she knew it.
"I didn´t hear you. What do you want me to do?"
"Err, I, I want you to put my hair up in a ponytail."
"Now we are getting somewhere. You see your first step wasn´t that difficult."
"My first step?"
"Yes, your first step towards girl or womanhood."
While she got a pink scrunchie out of her bag and got up behind my chair I started to protest.
"I am not taking a step towards womanhood like you said. I just thought it was fair to you after telling me all this to let you put my hair into a ponytail."
She laughed while she started to put my hair together, sweeping it up.
"Look boys. Gary here agreed on having a ponytail in girl fashion."
With that she deftly wrapped the scrunchy around my hair and I felt the pressure on my head when she put it tightly in its place. I heard the guys laughing, whistling, shouting. "Go Jasmin, go. Have fun with the sissy."
I blushed, completely humiliated while she sat down again. She patted my hand.
"Don´t worry. Nobody knows you and it is just for a while. Don´t pay any attention to them."
"Why did you have to announce this to the whole Bar? You completely humiliated me."
"You look soo cute with your girly ponytail. I just had to do it. To show you that I wear the pants."
I hung my head in shame and right then the waitress brought me a veggie burger with a little pink flag on top. I looked questioningly at her. She smirked at me.
"All sissies receive a pink flag. It suits them."
Jasmin laughed and I blushed again. Subdued I started to munch on my burger. Meanwhile Jasmin explained to me her feminization. The only difference from before was she talked like she wanted to feminize me.
"You know after having you shaving off all your body hair I will dress you in panties, bra and stockings."
I looked up. "Why do you say that. I will not do such a thing."
She grinned at me.
"Since you are wearing a girly ponytail I thought you may want to be my girl. Well, probably it is better we drop this matter. Hey, what are you doing for a living?"
I was glad that she stopped this embarassing matter and even so the talk shifted away from my or any feminization I was totally aware of my tight ponytail each time I moved my head. I passed a beautiful evening with this intriguing woman and in the end she knew virtually everything from me. That my parents had died, that I didn´t have any relations anymore with my siblings and was basically a loner. I told her that I liked to use all my money on travelling so really didn´t have time to start a serious relation.
After a few hours I got really tired and felt the jetlag so I told her I´d return to the Hotel and would love to see her again. We both left the bar and walked together.
"Look", she said. "We can spend time together again. I´d love that, you seem nice enough but then it is on my terms."
I interrupted her. "What terms?"
"You´ll go shopping, buy and dress in the things I tell you. Then we can meet again."
"What, what do you want me to buy and wear?"
"Easy. First you go and buy pink panties, pink bra, then black garterbelt and black stockings. A pink blouse, black pants with side, no make that backzipper, a black jacket and black open toed pumps, just a small heel, lets say two inches."
I gasped.
"I want to see you again but I can´t do that. I´d look like a complete sissy."
"Either that or you won´t see me again. Look, why don´t you sleep it over and call me tomorrow before 4pm and I´ll help you with the shopping. It would be my pleasure. I also would like to see you but once again only under my terms. So take a rest and have a good sleep. Hope you call me.Oh by the way, judging by your constant hardon somebody like the ideas to be dressed up as a sissygirl. Bye."
With that she pecked me on my cheek and gone she was disappearing in the crowd. I stood there face flushed and completely humiliated and true to her words, yes with a big hardon. I felt the embarassing growth of my penis while she told me her terms but had hoped that she wouldn´t see it. Fat chance!
I slowly walked back to the Hotel and when I received the keys to my room the nightwatch smirked at me. I didn´t get it until I was in my room entering the bathroom in order to brush my teeth. I was still wearing my hair in a high girly ponytail with a pink scrunchy. I shook my head and my my hair swirled around. I just couldn´t hold my horses anymore. I was soo horny from all the talk. I dropped my toothbrush, opened my zipper, wrapped my hand around my penis and only seconds later I shot a huge load with an image of me getting dressed up by this intriguing woman. Oh my God, what did I do? Guiltily I cleaned up my goo which had sprayed all over the bathroom and got into bed. It was useless, I tossed and turned, I couldn´t sleep. My hardon quickly returned. I thought of this woman. I couldn´t get her out of my mind. My hand wandered downwards and soon it was again wrapped around my member. Now I took my time. I wanted it to last. Slowly I rubbed myself, stopping several times before it was too late. With eyes closed I saw myself walking around dressed up in tight backzipper pants with a smooth girlish front, my pumps clicking on the floor, holding all kind of shopping bags in my feminine hands. Feminine hands? Yes, I was sporting long pink fingernails. The image was too much. Once again I came hard and sprayed all over my chest. Oh my God, what is happening to me I thought. I quickly got under the shower and washed myself, once again full of guilt. Back to bed I was able to falls asleep eventually. In the morning I told myself I wouldn´t phone this woman. I am a man and didn´t want to be anybodies girl. After breakfast I went out sightseeing. While walking around the MOMA I couldn´t concentrate on the Art. Instead of watching the equisite collection I simply saw myself dressed up with this intriguing woman standing behind me whispering in my ear "phone me, phone me". It felt like a mantra to me. I looked around but nobody was there. Was I getting crazy. No, I just needed some fresh air. Oh, I know, I would take a boat tour an the Hudson river. Once on the boat I felt better but only for a while. My urge to phone her grew with the hour. It didn´t make sense but I was completely captivated by this woman. As soon as the tour was over I went to the next phone booth and dialed her number. Her voice came on.
"Jasmin Spencer, hello. Hello?"
I wasn´t able to utter a single word. I just breathed heavily into the phone.
"Is it you Gary? Is it you? Answer me?"
I still couldn´t speak.
"Ok, I assume it you Gary. Look I give you my address and you´ll take a cab and I see you here in a short while. Just write it down. Ok?"
I simply did what she told me and wrote her address down. Then I took a taxi and in less then 10 minutes I was standing in front of a huge and elegant building. Oozing money. I introduced myself at the welcome desk and asked for Miss Spencer. Then I took the elevator to the 25th floor. Walking down the corridor I stopped in front of her apartment, 2508. Oh my God, what am I doing here I asked myself. I just stood there, unable to move or do a thing. I turned around and walked back to the elevator. I was scared shitless. I pushed the button and took the elevator back down again and simply walked out. I didn´t listen to the man at the desk. Outside I simply sat on a bench, sorting myself out. If I would go back in there it was the end of my life and definetely the start of a new one. I closed my eyes and started to fantasize about what would happen if I´d go back into that building. I saw myself knocking at the door, her welcoming and ushering me inside. She didn´t waste time and made myself undress.
"You need to get rid of your body hair first. We need to get you prepared for our shopping trip. It will be soo much fun for both of us. I promise."
Oh my God, my hardon had returned. My pants were almost bursting, well at least my underpants. I needed to get back in there. It was the right thing to do if I had a hardon each time I was thinking about it. I knew I was hers. Slowly I got up and walked back to the building The man at the welcome desk was already waiting for me.
"I phoned Miss Spencer you had left. I am glad you are back. She made me come up to her apartment where she gave me an envelope which I am supposed to give to you in case you come back. Here it is."
I took the envelope, turned around and read it.
If you are reading it you obviously came back. You need to be punished so you will take out your pink scrunchy in front of everybody and put your hair up in a high ponytail and ask the guy from the welcome desk to announce you. Tell him he is supposed to say that you are ready for me wearing a ponytail. If he doesn´t, don´t bother to come up. I will never see you again.
I thought, this isn´t happening to me and almost dropped the envelope. Slowly folding it and putting it in my pocket, I felt the scrunchy brushing against my hand. The funny thing is I couldn´t even remember having it put in there. My subconscious must have told me.
Did I really want to do that? Was she worth it? Oh yes, I obviously wanted it because the tightness in my underpants caused by my once again growing penis proved my utter helplessness to withstand this mysterious woman.
So with shivering hands I took it out of my pocket, started to gather my long hair, swiftly put them up and secured them then with the pink scrunchy right at the top of my head. Then I slightly coughed so the guy at the desk took notice of me. As if he hadn´t during my show with the scrunchy. At least his face didn´t show. He was all business.
"Sir, I, I am ready for Miss Spencer. Could you, could you please phone and tell that I am ready for her with a high ponytail."
This line seemed to change it all. He smirked at me.
"Oh yes, of course Miss, err, Mister? I will annouce you. "
I turned beetred while he phoned Miss Sepncer. The he simply said "You are expected."
The time during my short walk to the elevator seemed to stand still. I felt his eyes glued to me. If he could, he would have burned a hole in my back. My ponytail easily swinging from one side to the other. I felt dizzy when I pushed the button. Just before I stepped into the elevator I heard the man talk to me again.
"Oh, I almost forgot. When you arrive at her door, you are are supposed to undress to just your, err, I assume your panties Miss. Then knock at the door and kneel down looking at the ground. When the door opens you are to say ´Here I am Master Jasmin to start my new life´."
He chuckled.
I held my breath. Why didn´t the earth open up under me? Why? Why did I let this humiliation happen to me. I could have turned around. Rip the scrunchy off my hair and run as far and as quick as I could, while I still could. But no, I stepped with tears in my eyes inside and was crying and shivering at the same time when the elevator arrived at her floor. I composed myself for a moment before I quietly stepped out and looked around. There was only one door. So she seemed to own a whole floor. I looked around once again to make absolutely sure that this was the case. Then I started to undress. My hands shivered so much that I continously fumbled with the buttons and it seemed to take me forever to take off my clothes but was probably just a couple of minutes.
No, and I was not wearing panties at all. I just wore normal black mens briefs. I shook my head, it was not fair to have had to endure such indignity by a guy at the desk. I should have stood up to him plus I should have corrected him me calling Miss. I was angry, I was shaking. Oh this was more than crazy. Of course with my show putting my hair up in a high ponytail, above all with a girly pink scrunchy, he thought I was a sissy, a typical submissive sissy. Of course I wasn´t one. I just wanted to see this woman again. But to which length she took it to let me see her, which indignities I had to go through? Once again I shook my head. Was I already so pussywhipped that I did all these crazy things without ever having had so much as a whiff at her pussy?
What was it that drove me to almost crave the humilation and indignities? I came to my senses and tried to admit the truth in my head to myself. There was only one answer which was even more obvious while I was standing half naked in front of Miss Spencers door. My huge erection, err, at least it seemed to be one for me, showed me that I must love it. So the guy downstairs was right, wasn´t he? I was or am a sissy, a Miss to him. Yes, I was such a sissy. I deliberately shook my head. My ponytail swung to the left and right, my hair brushing over my naked shoulders and my hard penis seemed to stiffen even more and if it could have burst through my underpants it certainly would have.
I started to cry again but now of relief, slowly knelt down and knocked at the door. Yes, it was time to start my new life.
Depending on the feedback I may write a follow up. Hope you enjoyed my story.