Becoming Of A Sissy

Hello guys!! Am a 27-year-old mallu living in Chennai now…This was an incident which happened 13 years back when I was in school. Back then I was a fair lean guy back then with a very smooth lean body. I had small pointed boobs also. My dad used to drop my mom and me and leave and we would stay there for a month before we come back to Chennai.

When we stay there I use to sleep with my mom’s younger brother who was still not married back then in his room. He was a pretty muscular and hairy guy. He use to take me around to places. One such night after dinner at night I was lying on his bed and he was watching something on his computer.

When I asked him what it was he told me it was a movie and asked me to sleep. Out of curiosity, I jumped off the bed and when I peeped into the screen I saw it was a sex video. I told me even I wanted to watch and he let me with one condition that I should not tell anyone. I agreed and we started watching. It was an Indian video of a middle-aged couple completely naked and doing foreplay. I was immediately hard and it was the first time I was watching a porn video. I looked at him and he was slowly rubbing his hard dick through his track pants. It seemed to be really thick and long from what I could make out from outside.

A few minutes later he put his hands around my neck and slowly started feeling and pinching my nipples. I didn’t protest at first as it felt good and I was extremely horny. Later he asked me to remove my t-shirt which I gladly did. He continued pinching and fiddling with them with his right hand while his left hand rubbed his cock. Suddenly the video stopped and would not play, he tried removing the CD and inserting it again and it stopped at the same place. He got angry and told let us go to sleep and tomorrow he would bring a new CD. I was wearing my T-shirt when he told me not to and we would sleep bare body and he would play with my nipples for some time. I also agreed and lied on the bed dressed only in my shorts with my dick really hard. He removed his t-shirt and lied beside me and started pinching my nipples and this time he was pressing my tiny boobs as well. All of a sudden he put his mouth on my nipples and started sucking them while I was moaning.

He slowly took my hands in the meantime and put them inside his tracks and made me hold his thick cock. Feeling the sheer thickness of his cock and the veins running around it startled me. After some time he told me he wanted to fuck me in my ass. I immediately denied it and he told me he would inform my mother. This left me with no option but to accept it. He removed my shorts and made me sit on the edge of the bed and removed his tracks. I was shocked to see a black thick cock around 6 inches with his dick head almost the size of a small ball in front of me. He made me suck it for some time.

Initially, it was disgusting and I was crying while sucking it and only one-fourth of it was fitting in my mouth. Later he pushed me onto the bed turned me around spread my ass cheeks and started licking my hole. I was now almost in heaven out of pleasure and slowly he put one of his fingers inside. I got a jerk and all of a sudden lost my erection and got a sharp pain and pushed him away. He came back spit on his finger and inserted it again and this time it went fully in and was burning like hell and I was screaming with my mouth on the pillow. He fingered me for around 10 mins and now it was pretty comfortable for a finger to slide in. Then he got up and opened his wardrobe and brought a rope with which he tried to tie my hands. When I stopped him he gave me a tight slap and tied my hands to the railing of the bed. He then took out a dirty underwear of his from the bathroom and stuffed it in my mouth and taped it around the back of my head. I knew what was coming and was crying and praying and was sweating like hell.

He came near my face gave me a kiss and wiped the sweat off my forehead and told in my ears enjoy. He then positioned himself behind me and put some more saliva and started entering me. I felt like i was being torn from my ass and was almost about to pass out because of pain. His dick entered my ass with a pop sound and I felt like my ass is completely full. He was no longer able to push it in since it was too tight. He took it out went to the bathroom and I was feeling like some part of my body went missing because of the emptiness it created.

He came back with a shampoo and lubricated my ass and fingered for some time. Because of the burning caused by the shampoo I had to relax my ass hole. He then applied some more to his dick and slowly entered my ass. It now went in fully and I was feeling heavy pain. He let it stay inside without moving for some time. My ass relaxed around his cock and he started pumping in and out and I was crying in pain. My sound was not going out because of his underwear in my mouth. After few mins, I started getting some weird pleasure and started moaning. He now stopped and removed his cock and made me lie on my back lifted my legs and supported on his shoulders and entered me again and started pumping heavily. My dick became extremely limp and very small and I was now moaning because of my new found painful pleasure. After 3 to 4 mins I started cumming on my stomach from my limp dick to my surprise. This got him more excited and calling me a little sissy he started pumping furiously and came inside my ass. He removed his dick and i found myself farting and completely empty. He untied me and took me to the bathroom and we took a shower together.

I thanked him for the fuck and told him it was still paining. He told me I would get used to it. On hearing it I figured out how it was going to be a daily affair till I stayed there. We went back to the bed and slept together naked hugging.

This was the beginning of my sissy life with many more interesting events to follow. Little did I know at that time that my life would take such a drastic turn from then and I would encounter much more including few episodes where even some of my family members would involve including my mother. Let me know your thoughts and write to me if you want to know more events which happened later on. You can even mail me on “[email protected]”