Sissy Princess To Slut – Part 1

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I am Shakti, an average Indian boy with an ordinary life. I have a mother and an elder sister. My father left us when I was 4. I have asked my mom where was he but never got a proper answer. When I was 14, my sister said that he ran off with his friend and never came back.

This is my life, it sucks, isn’t it? Okay, so when I was 19, I started to masturbate but got bored soon and started to explore more. That’s when I realized, I was a sissy.

One day, my sister had a high fever so my mom took her to hospital and I was left alone. My friend asked me to bring my pen drive to school the next day. I was searching for it in my room but I was unable to find it. I thought maybe my sister has it.

So, I went to her room and searched but it was not there either. But I found a thing which was soon going to be an important part of my life.

Yes, I found my sister’s pantie. My adrenaline started rushing. It was the perfect time to wear that. So did I. Then I took my sister’s bra, stuffed it with my socks and wore it too. It looked perfect since there was not even a single hair in my body.

Then I took her tank top and skirt and wore them too. Dang, if you have seen me at that time, then you’d bang me for sure!

This continued for the rest of my school days. I would say to my mom I am sick and spend the day wearing my sister’s dress and doing the makeover.

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Later I got admission in a college which was far from my house. So I took a room outside and the first thing I did was ordering a girly set of dress, a makeup kit, and a dildo. I used to dress me up and fuck myself daily during those days.

I had grown somewhat long hair till my shoulder. So I looked exactly like a girl when I was dressed up. But in college, I used to look like a bully.

One day while I was chatting with a stranger online, he asked if he could come over. But I refused. He promised me it would be a secret and he can give me money. I was biased but soon invited him over. We had not seen either of ourselves till then and so, I was excited.

I cleaned myself up, shaved and applied some make up. I took out the babydoll lingerie and wore a black saree above that. I was waiting for him all prepared.

Knock knock.

“Should I open it or not?”. “If I open it then there is no going back”. There were a lot of thoughts in my head. But I opened the door anyway.

He was around 40-50 and had a nice shape. He was mesmerized by my beauty and I invited him in. He asked, “Are you really a boy? Because you look stunning as a girl!”

I was in heaven. Then he asked me what was my name. I said it was Radhika. Then he asked, “Can I see what you got Radhika?”

I understood the reference. I took him to the bedroom. He tossed his phone over the table and unbuttoned his shirt and hung it over in the hanger. He was wearing a t-shirt inside. His arms and packs were awesome. He seemed too fit.

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He came near me. He smelled like chocolate. He hugged me tightly and smelled my hair and started giving me a kiss on my forehead, down on my cheeks and then on my lips.

Oh! It was awesome. I haven’t had that experience even when I kissed my girlfriend. Kissing a man is pure awesomeness.

He undraped my saree without taking his lips from mine. Then he stopped, removed his t-shirt and unzipped his pants. Meanwhile, I undraped my saree fully. He came near me and took off my lingerie. I loosened my panty and pulled it down. There was my tiny puny clitty cock. It was harder yet it was smaller than his normal cock.

He kissed my nipples and turned me back. Now I was in doggy style. He took the lube and applied it in my boy-pussy and started to finger me. I moaned in pleasure.

I even had an enema on that day so that we’ll not spoil the day. He then inserted 3 fingers and I was crying in pleasure. Then he fisted me. I shouted, “Fuck… Ahhhhhh…!” and made noises.

He then took his tool. It was larger and thick. He inserted it in. Then he thrust as fast he could. My puny penis was shaking vigorously. And damn, I quickly reached a sissygasm. My cum dripped. But he was thrusting like a beast.

“Gulp”

He unloaded his cum and breaded me. He took out his dick, his cum was oozing from my asshole. It was expanding and shrinking. My body trembled. He then came in front with the dripping cock. He said, “Suck it, slut!”

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I cleaned his cock my putting it in my mouth. It was the first time I was tasting a man’s cum. I have tasted my cum number of times but his was tastier. I sucked it completely and played with his cum in my mouth and gulped it.

Then he swallowed some pill. He got hard again. This time we did it in the shower.

We had sex 4 times that day. At the end of the day, we cleaned ourselves. I wore the same dress and we went to the hall. I made him some tea. He asked me to sit near. We watched tv for a while.

It was 7 pm by then and he said he had to go home as his wife would be waiting for him. Then he gave me 2000 rupees in cash and gave his number. He asked me to call him if I needed money. When he was about to go, I asked if I can take a selfie with him. He said sure. I took my phone unlocked it.

Suddenly, he was shocked after seeing my wallpaper. It was me, my mum, and my sister. I opened the selfie camera. I was smiling but he was in shock.

He said: “Shakthi! You’ve grown so big!”

To be continued.

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