So, it was a question about the wildest thing I have been through in my crossdressing journey. I have been through enough and I have enjoyed every inch of my sissy life so far. So, this is the time when i got fucked on a train by a real man.
I was 18 at that time, and it was all new for me. I was sexually aroused all the time and has started dressing slutty and sissy with my sisters clothes. I have had many cocks since then, but till this point, I have just had a casual experience with my building friend. And this was the time I actually became a real sissy slut.
I have never taken a big cock in my ass or mouth or anywhere and this is the first time i did it.
One fine afternoon, I was on a train that was headed to my native , somewhere in New Jersey. There were no corridor in the train in those days and all the coaches were separate from each other. So, the day I was not dressed completely, but I had my girly underwear and wore a bra beneath my regular clothes. I am already smooth and there are no hairs on my body as per. And during those days, I used to keep my hairs long. So, all in all, if you ignore my male clothes, I was like a girl only.
I was alone and kind of horny. It was a cold night and the compartment was really empty. No one was there in the compartment except some people. And they were also like half asleep. My station was expected to come in the morning so, it was a gift kind of opportunity for me. So, i got bored and really no one was there in my compartment so, that I could do any thing. But I was desperate that day. I started doing random things and suddenly i peeped through a tiny hole that connected this compartment with the next one. I was stunned to see that a guy in his late 50s was there with an adult magazine and was shagging off to the porn. What a waste of energy and cum. If I am ready to explore my wonderful body, with a wonderful man, why would you shag?
So, it was a moment for me to take a decision. I quickly hurried to step down on the next stop and yes, it was the same compartment in which the guy was shagging. I switched all my stuff to the next seat and I was almost very near to that guy in an almost empty compartment of this long route train.
I was sitting opposite to him and my heart was pounding as this was my first casual stuff out of the house and I was pretty nasty at even thinking about this. And I dont even know whether he is into taking sissy asses or not. But I tried my luck and somehow I got lucky that night.
So the train again started and he had his magazine beside him under his overcoat. That was fun. So , the train got into its speed and I started getting a look on his magazine and i realized it was about shemales. That was the best thing that could happen to me.
I could see his bulge in his crotch area, and it was huge. I said, ” Nice magazine” , He nodded yes, it is! He just smiled.
I gathered courage and told him that I saw him what he was doing earlier as there is a hole in the wall behind him. So, he looked at me and said, Are you by any chance a shemale? I said, no but I like being girly and naughty. He laughed a little and asked me my name. I told him my name and than the stuff started.
He asked, ” DId you see it?”
I replied, ” Yes!”
He asked, Do you like it?
I said, of course, its the biggest I have seen so far. He asked me further about my choices, and where i was heading to and how much time do we have to carry out the business if we try. I replied that we can have a whole night together till my station come. He loved it and asked me without any hesitation ” Would you want to touch it?”
And than he opened his overcoat and there it was. The cock i saw the other moment. It was beautiful and like a piece of art. I touched it and then he said, I want to see, how girly you are down there.
I replied readily and then I opened my legs. I told you I was wearing male clothes, but i took off my pants, and got naked down there. No one was there to see all this except this guy i dont know anything about but, it was fun and I was horny. It was a lingerie down there and my tiny dick was aroused. I removed my panties and showed him what he wanted to see.
He asked me whether I was expecting any action to which i replied sure, daddy!
He got excited the moment i called him daddy. Now it was time for him to take the charge and he did it. He opened his legs and asked me to love his cock. It was awesome and the pink head literally made me feel how girly I was.
I sat on my knees and took his cock in my hands. As i told you it was like my starting, so i was hesitant to take it in my mouth primarily for the reason of without any condoms. He looked at me and asked, what the issue? Why am i not taking it in my mouth? I said, I need a condom to cover it first, to which he said, I dont have a condom and i dont need one as he gets tested regularly and he is clean. I dont know why i trusted him, but i said, I have a condom if you allow me , please I am a bit scared. He said, ok to my condom request and then I took out my condom from my luggage. I told you I was without pants and i had to get up to take out my condom like that only. The compartment was empty like but still some people were there. It was a hot experience. I got up and took my condom from my bag and came back to him. I put the condom on his dick and then i looked him into his eyes and that was it.
I sucked his cock for like 2 or 3 minutes and he made me do it by thrusting my throat onto his dick like anything. He forced me to put his cock as deep as possible and then I sucked his cock for a smaller time. I was not experienced in sucking cock and it was evident to him. So, he asked whether I was ready to take it in my girl hole I was thrilled and said Yes.
So, he asked me to stand up and take corner position on the rack behind the seats. I did it and we were not visible to anyone unless, someone gets up to use the washroom. So, i was damn thrilled about the idea of getting fucked in a moving train in my sissy ass, but it was happening.
He removed my panties and then i could feel his big hot and wet cock on my bum cheeks. He was exploring my ass and spitted on his dick with his hands. I was kind of ready but tight too. So, i wanted to embrace my self for the pain coming, but it went slowly inside my girl pussy and I got a little pain in my ass. It was definitely painful and I could see myself getting up to the point where he was considerably inside my ass.
I was thrilled and started taking heavy breaths. He stopped and waited for me to relax and then he again thrusted his huge man dick in my sissy ass. He was almost as deep as my ass hole depth in my body and it was excruciatingly exciting . A lust with pain is wonderful stuff.
After some time, he started moving his cock inside out and i was in heaven. I was feeling good and lusty at the same time. I was feeling something very hot in my ass and his dick was way bigger than my previous experience.
So, overall, I was getting fucked in a public place as a sissy and he was fucking me really hard. I dont think he was ready to cum anytime soon, so i started whispering, enough daddy. enough daddy. Take it out daddy.
He kept on fucking me and my voice kept on getting lusty and begging. But he never listened to my beggings. He was all set to make me his slutty sissy and i was surprised to see his stamina in a moving train.
So, finally the moment came and he was about to cum and asked me did i want to swallow his cum? I said no daddy, keep it out in my ass only with the condom please. May be next time I would swallow it.
He fucked me like another 5 minutes and then he came in my ass. With this my first public fucking got finished and we both got back to our seats. He didnt allow me to wear underwear and he took it with him. He told me to wear my pants without panties and exchanged the numbers. We were heading to same station and we were kind of neighbours.
After this, I met him many more times and became his part time permanent sissy slut for so many casual encounters.