Hi, my dear readers, I hope all of you are doing well. I thank everyone who appreciated and showed love for my previous story. I also thank all those who wished to meet me.
But I am very sorry to say that I don’t prefer meeting strangers. Also, thanks to those who did not ask me to share contact details of all my encounters.
This story is from back when I was doing my Master’s from Calcutta University. This is not your typical sex with a hot lady, but rather using a teenage Sissy. I hope readers do find it interesting and get their pants wet.
Now, before I start, let me describe who we are. Sissy are basically men who want to be treated as females. Unlike cross-dressers, some even undergo surgery to either shorten their dick or implant silicone boobs. Most are extremely submissive, but a few are also dominating, and they are easy to tame.
This one is one of my such encounters, with a Sissy who was in her late teenage years, to be specific, 19 years old. The name of the Sissy, which is not real, was Rosy. But unlike those mentioned above, this one was a trans Sissy. It was a Transgender person with a feminine character.
Later, I came to know this was because of his stepfather. He made him undergo surgery as he wanted to make a bitch out of her. Thankfully, the dick was small, around 2 inches when hard. Her anal was not a virgin, with 32 B cup boob’s size. Her height was not much, around 4’7”, with an hourglass figure.
If you look at her, at first you would think she is a typical sexy, horny schoolgirl. But a closer inspection would say otherwise. Sorry if you are getting confused by his/her, as I am not sure what the gender of a Sissy is. If anyone knows, kindly inform me of the same.
But if you look at her in a short dress, you would probably get horny and maybe wet in your pants.
Now, to the story, how I met Rosy, it is very interesting. Back in 2013, I was doing my Master’s from the CU Alipore campus in Ancient History. I mostly travelled via metro, and I was staying in a mess/hostel in Dum Dum. Those who travel in the metro would be well aware of the root.
I, for the most part, used to observe sexy ladies who were mostly in their work dress or in scanty clothes. But what attracted me most was the young girls in their sexy short skirts.
Yes, I know after reading this, most of you are thinking I am a paedophile. But let me be clear, I only fuck women or Sissy above 19 years, below is not my thing.
Now, one such day, during rush hour, I was travelling along with my friends. The metro was jam-packed with little to no room to stand. And with no space to move, I was standing somehow in between the intersection. At that time, I was more worried about reaching safely than doing anything else.
Also, I was not able to see who was in front of me. My back was against the wall, so immense pressure was coming from the front. That’s when I felt someone rubbing my dick, which was new for me. In such a jam-packed situation, things like this happen with or without accident.
But mostly for a few minutes or seconds. When it continued for more than 5 minutes, I looked in front. I saw a teenage girl looking at me seductively and rubbing my dick over my jeans. I didn’t know what I was thinking. I grabbed her by her waist and brought her close to me.
So close that I could feel her boobs. I inserted my middle finger into her anal. I started to rub it and squeeze the ass cheeks, till we reached Park Street. After that, the metro was almost empty.
So, we both adjusted ourselves, I got down at Rabindra Sadan, and thought this would be a one-time thing. But the very next day, the same thing started again, and we both enjoyed each other for almost a month. The routine was almost fixed.
What I did understand and figure out was that, first, she was taking the metro from Shyambazar. After having our foreplay sessions for a month or so, I decided to see if my hunch was correct or not. So, one day I went a bit early and took two metros before my usual one and got down at Shyambazar.
I sat on the bench waiting for her to come. As I sat and waited, I saw her wearing a pink tan top with a mini skirt. She didn’t see me, which was a good thing, as usual, she hopped on the metro, and went to her usual spot. I was watching all this from afar,
After not finding me, she sat on a corner, all sad. I sat beside her and started to rub her legs. She looked at me with a genuine smile and came and asked, “Where were you?” I was taken aback by her sweet voice and replied, “I was looking at you from there.”
After this, we had a friendly conversation, but neither of us revealed each other’s personal details. Our foreplay and after sessions continued for almost 3 months, but slowly she was opening up to me. We hadn’t shared our contact details yet, and were refraining from asking each other the same.
One day out of the blue, she asked me if I was free on the upcoming Sunday. I replied affirmatively. She then took my phone and dialled her number. I decided to save the number. From that point on, we started having phone sex. I came to know she was a Sissy with a shaved 2-inch dick.
I was thrilled to know that. Not because I wanted to fuck him, but because this was my first time using a sissy whore. Fortunately, it won’t be the last time. We were having phone sex, not every single day, but almost on weekends. This continued for well over a month.
During that time, I came to know he/she liked to be treated as an anal whore and a fuck toy. I also knew she had a virgin ass, which meant it was a cherry waiting to be popped. I was excited to use her, but it would take me almost 3-4 months to arrange a session.
One fine day (Sorry, but I don’t wish to specify date or day), she called me and asked if I was free on the same day after 6 pm. I replied affirmatively. She texted me the location and asked me to bring some lube and a condom. In turn, I asked to dress like a whore and to ensure not to wear innerwear, she obliged.
The location was near Newtown, Salt Lake. Frankly speaking, it was a posh society where people from my middle-class background dream of staying. It was well under surveillance, and outsiders were not allowed to enter without permission.
So, I dialled his no and informed him I was in front of the security. He immediately told me to give my phone to the security, and I obliged. The Security in-guard entered my name and flat no, then gave me a green signal to proceed.
As I went, I received his floor number and flat no. I entered the same in the lift and knocked on his door. As the door opened, I saw her wearing a mini skirt and a top. When I asked about the location, she informed me that it was her flat. Later, I came to know her father had gifted it to her (why I didn’t ask).
But I did ask her why she travelled in a crowded metro. I came to know that it was because she loved being groped. But this was her first time doing it for real, and by her looks, I could say she was eagerly waiting to be used. I will not describe and waste your time by writing what refreshment she offered me.
But I will start from where she got down on her knees and started to lick my dick. First, she unhooked my jeans, then slid them down along with my undies. As she did that, my dick popped out strong and hard. She pulled down my foreskin and gave a kiss on my dick head, then started to lick it.
I could feel her tongue, and it was getting hotter as she did that. I was in another world, and the feeling was sensational. I kept my head back, letting her suck my dick. She liked a pro, gently squeezed my balls and swallowed deep. I could feel her tongue around my dick, the feeling of which was sensational.
I could never forget how I felt. This continued for some time, till my pre-cum started out and till I started to pee. She drank my pee like water. I ensured she didn’t spill any by pushing her head into my dick. After that, I made her sit on the sofa with her legs open and her anal visible.
I pushed my middle finger in and started to give her an anal finger job. As I did that, I also started to play with her dick, pulling and squeezing it. As she played with her anal, her dick was becoming hard. She was moaning and begging me to fuck her.
I continued playing with her dick and anal for well over 10 to 15 minutes. By this point, she had cum twice or thrice, I don’t remember. But to be fair, her dick was clean-shaven, including ass and thighs. She had recently waxed her body. I even licked and sucked her tiny dick. Her cum tasted good.
I did the same with her balls. All this made her hornier, and she was begging me to use her. After looking at her mischievously, I decided that the time was for some fuck session. By this point, I was hard. I opened her leg and pushed my dick in her anal.
As I pushed in, I took off her top and started to lick her nipples, played with his dick. But as I went in, I could hear her screams. Begging me to stop, I licked her nipples, squeezed his dick and pushed deeper in her anal. Her screams became louder and louder as her virgin anal tore open.
She was trying to push me away, but I forced myself into her anal. At the same time, I bit her nipples and pulled them up. As I did that, she started to beg me for mercy. I widened her legs and continued pushing in, without showing any restraint or mercy.
I was enjoying her screams and begging. In my mind, I was feeling like I owned the slut, and nothing could have stopped me. I was pushing deeper, and could feel her anal getting stretched, and open to welcome my dick. Once I was fully in, I kept it as such for some time, letting her get adjusted to my dick.
Once she was comfortable, I pulled out and pushed again. I did this for about 5 to 6 minutes. Each time I did that, I could feel her getting horny and excited. I wanted her to feel used by a man who was superior to her. Both in strength and stature, she was transforming from a virgin sissy to a slutty sissy.
For the record, I was not in love with her, but rather was using her for my pleasure. All of a sudden, I kept her legs on my shoulder and increased the speed as I could see her moaning. I picked her up by her ass, she held me tightly and carried her to the bedroom.
I kept her on the bed and continued pumping her. I kept her legs straight and pumped her more. As I did this, I squeezed and pulled her dick up. Making her go crazy as hell. She started to cum, and begged me to stop. I continued to pump her like this till I unloaded myself.
But I was far from done, I then pulled my dick out and played beside her. I turned her sideways, slapped and squeezed her ass. As I did that, I smooched with her, we did a lip lock and played with each other’s tongue. When we did that, I slowly inserted my dick in her anal.
She opened her anal to let me in, and even kept her leg up. So, I pushed in as I pushed in, I could feel my dick getting harder and harder. As I pushed further in, I could sense her getting horny. I pulled her tongue out and started to lick it. As I pushed in deeper, my hands were playing with her tiny dick.
I was giving her a hand job. She was by this point cumming, and her nipples were getting hard. This time, I slowly increased my speed. I was slow but steady. Let her enjoy herself. I licked her nipples and chewed them. She, like a good whore, was letting me do all this.
I could feel my dick going deeper than before. As I increased my speed, so did her moans; she was begging me to fuck her harder and to let her cum. I was squeezing her dick and pulling it down, revealing her foreskin. I was doing this faster and was increasing my speed.
As I increased my pumping speed, so did I increase her hand job speed. All of a sudden, she started to cum, nonstop, as if she lost control over herself. I pulled her foreskin back. She was in immense pain, as her dick was a virgin, and I was forcefully pulling it back.
But her cum was nonstop. It was as if she were squirting all over the bed. Looking at all this, I was getting horny, so I started to cum nonstop, and emptied my balls in her anal. I kept it like that, then I pulled it out.
After that, I went to the bathroom and cleaned my dick and my hands. He also did the same, cleaned his dick and his anal. We took a short break. And we did a second round, where we did doggy style and cowgirl style. I will write about both if I get time.
Thank you for reading. If you want to connect with me, you can email me at [email protected].