Hello dear ISS readers,
My name is, well, my real name is not important anymore. A little introduction though. I belong to a small city in the state of Kerala in South India. Anatomically, I am a man. But since I was about 10-11 years old, I have always fantasized about being a girl. Typically, I didn’t have a lot of friends in school. When I hit puberty, nothing major happened. Only my ass grew big and round. I was continuously teased about the big ass. Anyway, since I pretty much kept to myself and was academically brilliant, I was the teachers’ pet and no one dared to bully me.
Whenever I was alone at home, I used to sneak up into my parent’s room and try out my mother’s clothes. It started with her makeup, then progressed to her lingerie and then progressed to her clothes – sarees, salwar-kameezes and night gowns.
When I was in the 11th grade, my mother passed away after a prolonged illness. This devastated the family. My father threw himself into his work, my brother moved to another city for a high paying job. My aunt who was a widow, came to stay with us and to take care of me. My father disposed of all my mother’s belongings and that was the end of my dressing days.
One day after about 9-10 months, while on the terrace of our apartment, I saw a very very sexy black panty with silk laces hung out to dry (along with other clothes). I assumed that it was Malathi Aunty’s from 3C. She was the only one in the building who used to dress up in outrageously sexy clothes. My old urges came flooding back. Making sure that no one was looking around, I grabbed the panty and shoved it into my pocket. With my heart racing and face flushed, I fled to our apartment, ran to my room and locked the door.
Slowly I took the panty out. I smelt it and then ran it all over my face. It felt so good. I removed my shorts and underwear and slowly slipped on the panty. The feeling of silk and lace against my ass was amazing. I hardly touched my erect cock once or twice and immediately came inside the panty. Now that the excitment had reduced a little, it was replaced with fear of discovery. What if someone saw? What is Malathi Aunty comes home and complains? My father would beat me up and skin me alive. But after a few days, nothing happened. I thought it was safe now. I started wearing them every night before I slept and the world felt right.
Soon the summer holidays began. April and May are gruellingly hot in Kerala. Since I had no friends to speak of, I spent the days indoors and read a lot. One day, my father brought home a suprise gift – a computer. It was like discovering a new world. The first few days were spent figuring out how to work things – I spent day and night on it. Then I took it apart and put it back together, changed the OS, customized and pretty soon was in love with it. And since I had internet too, I had a whole new world to explore. Of course that meant surfing for porn too. But regular porn did not excite me anymore. I was soon surfing for CD and shemale porn. I always assumed that I was the shemale in the movie.
One day, feeling pretty adventurous, I wore the panty inside my jeans and went out. There was a movie playing at a theatre which had one of my favourite actresses in it and I wanted to watch it. I took the ticket and entered the theatre. To my surprise, there was hardly anyone in there, maybe 4-5 people. I found a whole secluded section to myself. The movie started – but it wasn’t the movie I was expecting; the print was bad, the audio horrible. I rechecked my ticket and realised my mistake – I had taken the ticket for the wrong movie. No wonder the ticket checker at the door had given me a sly grin. “Dammit”, I thought. I got up to leave but then since I was alone, I was also scared if someone saw and recognized me when I got out. I decided I would wait till the interval and then get out with the others, that way, I had a better chance not being recognized.
The movie had begun and was a soft porn malayalam movie. Typical bad acting, bad editting but the girls were younger and better looking. I noticed a guy who was at the end of my row had moved 4-5 seats closer, I assumed he just wanted better viewing. About 10 minutes later, he sat in the seat next to me. I didn’t look at him first, but I smelt his cologne. On screen, a typical steamy scene had started. The guy beside me started breathing heavily and touching himself. Accidentally, he brushed his hand against my thigh. When I looked at him, he quickly apologized. He was dark and had broad shoulders, a massive chest and a pot belly. His arms were the size of tree trunks. I continued watching the movie when I felt his hand brush against my thigh again. This time I didn’t look at him and his hand remained on the side of my thigh. Slowly he moved it and placed it on top of my thigh. With his other hand he continued massaging his cock from outside. When he slowly started stroking my thigh, I looked at him again, this time he smiled and continued stroking.
This was a new experience to me and I loved the slow caressing on my thigh. His hand gradually moved up my thigh towards my hard-on. He took my hand and placed it on top of his cock. My caressing it, I could tell that it was big. This was the first time I was touching someone else’s cock other than mine. He slowly unzipped my jeans and unbuttoned it. that’s when he felt the silk and lace. His quickly took his hand away. When I looked at him, he was looking at me curiously. He took out his mobile phone and shone its light on my lower region and saw my black silk and lace woman’s panty. He grinned -a wide grin. He zipped me up and said “Come! Let’s go some place private.” I didn’t get up, I was scared. He said again, “Come or I’ll call all the guys here and show them what you are wearing.” He was stronger than I was and was capable of hurting me so I got up and walked behind him.
We exited the theatre and walked to his car. “Do you like wearing that?”, he asked. I nodded. “It’s nothing to be ashamed of”, he said kindly. We sat inside, put on our seat belt and started driving away from the theatre. “What’s your name?”, he asked. I didn’t say anything. “It’s OK. I believe this is your first time with someone. I’ll talk. You can talk when you are comfortable.”. I nodded. “My name is Kannan. I own and run 3 small hotels in the city. Food is my passion. I haven’t studied much, just 12th standard. But I have travelled all over the world representing Kerala food. I just came back 6 months ago from Malaysia. I live alone – I am divorced. She left me for another man. This is my story in a nutshell”. I sat quietly though the narrative. After a couple of minutes, I said “I am going start my 12th grade in June. I live with my father and aunt. My brother works in Bangalore. I lost my mother last year.”
“You still didn’t tell me your name.”, he said. I started saying “My name is..” when he interrupted “Wait!! I don’t want to know your name. Let’s call you NAMELESS” and he started laughing in good humour. I smiled. “Yes, “nameless” we’ll call you – Anamika – Nameless”. “B-B-but that’s a girl’s name”, I stammered. “Well, you’re wearing a girl’s panty aren’t you?”, he smiled. “How long since you began?”, he asked. “I always wanted to look like a girl, I started wearing my mother’s clothes since I was 10. But when she…….”, I stopped. “Say no more. I understand.” He turned up the AC and we sat silently for another 10 minutes while listening to some soft music. “I can help you” he said quite suddenly. In response to my confused look, he continued, “You can dress completely as a girl in my house, only if you want. No one is there to disturb you. I would enjoy watching you as a girl, that is, if you are comfortable.”
I was scared and trilled at the same time. On one hand, I could fulfil all my fantasies if I accepted. On the other, he was a stranger. Sensing my discomfort, he said “You can trust me. For now, just come home, we’ll simply talk – if you are uncomfortable, I will drop you back at the theatre – not even at you home if you don’t want me to know where you live.” The car turned into a lane and up the driveway of a nice looking bungalow. “You have a nice house, sir”, I said. “Thank you. By the way, don’t call me Sir. Just call me Kanna or Chetta “(Chetta – this is how generally women-folk address their husbands in Kerala. Literally though, the meaning is elder brother). “OK, Chetta.”
We went inside and he led me by hand directly into the master bedroom. He gestured towards a luxurious sofa and I sat down. He went out of the bed room and came back with a tray. On the tray was some alcohol, soda, ice and a cool drink. He gave me the cool drink and fixed a drink for himself. As I sipped my cola, he told me, “Come, let me show you something.” We walked towards a wooden door and he opened it. It was a walk-in wardrobe. Inside, was every kind of womanly outfit imaginable – sarees, salwars, kimonos, night gowns, bras, panties, lachas, lehengas, half sarees, set sarees, long skirts, short skirts, mini skirts, tops, tshirts, churidars and lots and lots of different makeup sets. It took my breath away. My excitment must have shown in my eyes because he said, “These were my wife’s. You can try some if you want” and he simply walked away. I ran my hands along the clothes -some soft, some silky but all very very sexy.
I came out. “Well?”, he asked. “I have never worn these clothes properly”, I said. “And I am shy when you are here.”. “I’ll be outside. Just call if you need anything.” and he left. I closed and locked the bedroom door. I slowly removed my clothes, folded them neatly and put them on the king-size bed. I looked at the mirror at my naked body – I am 5″ 8′ and weigh around 74 kilos, all of my weight is on my ass and my thighs. I have a slender hip and small boy boobs with brown nipples. I don’t have body hair at all. I start by choosing a black lacy bra which had some padding. I wore the bra and put it a little tight – this caused my boy boobs to be mashed together forming a little cleavage. Next I tucked my penis inside and wore a black lace panty.
I chose to go fully black because it would complement my fair skin. I picked out a black “pavada”(the skirt under the saree) and tied it up neatly at my waist. It was tailored such that it was tight around the ass until the knees and then loosened up. This gave an amazing shape to my ass. I chose a matching black saree which was a little see through material. I wore it’s blouse over my bra. Before I wore the saree, I decided to put on some makeup. I put some foundation and powdered my face.
Then I drew kajal around my eyes and curled my eyelashes with the liquid kajal. Next, I wore some dark red lipstick and some gloss. I painted my nails red too. I waited for 10 mins to dry the nail polish. After that, I wore some big hanging clip-on earrings. Then I started wearing my saree. It took a lot of time but I did it in the end. Lastly, I wore some red and black bangles and small black bindi. Satisfied with my look, I opened the door and walked slowly to the hall.
I was actually short of breath from excitement, mixed with fear and adrenaline. Was I really going to do this? This guy could be dangerous, besides I had never even considered hooking up with another guy before. Nonetheless, I continued walking to the hall.
Kannan Chettan saw me and his jaw hits the floor. “Y-Y-You look amazing, Anu”. Anu – that’s what he called me. I blushed. I went and coyly sat next to him all the while looking at the floor. He puthis for finger under my chin and lifted my face up. There was kindness, love and lust in his eyes. He drew close and slowly kissed me on my lips. It was my first kiss ever and I loved it.
He kissed me again and this time I opened my lips slighty. His tongue parted my lips some more and we were soon lip lock. The kisssing was hot, gentle, romantic and electric. My whole body was tingling. After what seemed like hours, we broke our kiss. “I haven’t kissed like that in a long time, love”, he said. “You are too beautiful to be true.” He drew closer again and kissed my neck – again, the feeling was electric. He licked the insides of my ears and continued whispering erotic things.
Kannan Chettan finally stopped his foreplay. He got up and took my hand and led me to another bedroom. The bed here was bigger he made me sit on the bed and he sat beside me. We kissed again. This time, when he kissed my neck, a soft moan escaped my lips. At that, he got up and removed his shirt and his vest. Then he unzipped his pants and removed his white underwear. I had never seen another man’s cock before. Kannan’ chettan’s cock was around 6 inches but it was thick and uncut.
He slowly advanced with his cock at the level of my lips. I had seen enough porn to know what he expected of me. I have never given head before but I have fantasized while practicing with bananas, and of course, tasted my own cum. But this was different, it was so warm, and he was a little bigger. I started gently licking and kissing his head and shaft but before long I was taking him into my mouth and as it went more and more inside, I gagged. After a while and some focus I was able to take most of him in while massaging his balls with my free hand. I didn’t even realize he had his hands firmly on the back of my head.
Slowly I began sucking. I loved the feeling of his cock inside my mouth. I guessed I wasn’t doing badly as he was moaning in pleasure and rocking his hips in rhythm. I tilted my head slightly upwards to look at his face with the cock in my mouth. I guess that the look of his cock inside my mouth and the innocence in my eyes while I looked at him drove him over the top. He cock started pulsating and i felt thick cream hit the back of my throat. Since his cock was still in my mouth, I had no choice but to swallow all his cum.
He slowly withdrew his cock from my mouth. He gently pushed my shoulders and laid me down on the bed. He lay on top of me and kissed me again full on the lips- this time, tasting his cum in my mouth. His hands kneeded my tiny boobs through the saree. He slowly took off the “pallu” of the saree. As he continued massaging my tiny boy breasts, he slid down and licked my navel. “Aaaah..”, I sighed. He slowly undraped the saree from around me and threw it on the floor. “Anu…..”, he sighed, “Do you like it?”. “Yes, Kannan chetta. I am yours and yours alone – do what you want. You have made me feel liberated.”, I moaned.
With his teeth, he untied my “pavada”‘s string and pulled it down. My hands were above my head and sweat stains were on the armpits of the blouse. Kannan Chettan, licked at my arm pits through the blouse. I moaned some more and my bangles clinked and my hand shuddered. He slowly turned me over and I got on all fours. Since the Bed was soft, my knees did not hurt. He slowly pulled down my panty. His string hands parted my ass-cheeks. suddenly I felt something wet and moist wiggling against my man-pussy. Kannan Chettan was licking it. My hole relaxed and soon his tongue was darting in and out of my hole. The slurpy sound it made was music to my ears. Kannan Chettan removed his face from my ass and slowly positioned his cock at the door of my virginity.
“Anu, are you sure you want this?”, he asked. “Do it Chetta. Please…..”, I begged him. “Make me your woman. Do it”. Slowly, very slowly, I felt the head entering. It hurt and I cried out. He immediately took out the head. “No, No, Dont stop Chetta please…..”, I moaned. He applied some spit on the hole and tried again. This time, the head got in. It was uncomfortable but did not hurt as before. Slowly, Kannan Chettan pushed a little more, all the while applying more and more spit to lubricate the hole. It was extremely uncomfortable. I squirmed and moaned and there were tears in my eyes.
At last I felt the base of his cock his my ass. Kanna Chettan did not move at all. We remained like that for a couple f minutes. My ass, slowly relaxed. I think he felt my ass relax because at that moment, he withdrew a little and pushed it back hard. “AAAAAA”, I cried and my ass clenched again. Again we waited and the ass relaxed. Kanna Chettan continued like this for about 10 minutes till my ass did not clench anymore. Then, he began rhythmically fucking me.
Oh, the pleasure, I cannot describe it in words. He was bent over me and was holding onto both my man boobs. This gave him grip and also massaged my man-tits at the same time. And he was fucking me-HARD. He fucked and fucked and I moaned and moaned. He was holding my hips when he started to moan with anticipation, I kept driving myself down onto him. He EXPLODED with a loud groan and curse. I felt him explode his cum into my ass, it felt amazing, so warm, so REAL. I was in heaven as I came myself, soaking the bedsheet underneath me. We continued our pace more gently, gradually slowing until I laid down exhausted and he laid down on top of me, kissing my neck, biting my ears and whispering sweet things to me.
He slowly withdrew his manhood from inside me. He turned and got off me and laid down beside me. I went into his arms and snuggled beside him with my head in his chest. “That was incredible.” I said softly.
He replied, “Even better than I expected”. We slowly started kissing again. But this time, it was out of love; I could feel the love in those kisses. At that moment, I knew I wanted to do this – for as long as possible. I wanted to be a woman and nothing would ever change that.
I think we both dozed of for a few minutes. I woke up with a start and saw Kannan Chettan was awake and simply staring at my face. When he saw me open my eyes, he kissed me. The kiss lasted for quite a while. He said, “Anamika, I want you to be my woman. For now and forever.”. I felt tears in my eyes. He kissed them away. “Don’t reply now, dear one.”, he continued. Take some time and if you decide you want to see me and see where this goes, I will always be a phone call away. He picked me up and carried me to the bathroom. We had a sensuous shower and then dried ourselves.
After I dressed in my regular clothes, Kannan Chettan took me to one of his hotel’s. We had an amazing meal there in a private booth. He then gave me his number. I told him where I lived and he dropped me home. Before I got out, he said,”my love, think of what I said. I want to spend every minute with you. I think, I am in love with you. I can only see you as my Anamika, my Anu and not as anyone else.” I smiled shyly and said, “Kannan Chetta, I don’t have to think about this. I want to be with you for as long as possible. I don’t know if this is right or wrong but I know is I want to be with you.” I kissed him on the cheek and got out.
As I walked towards the lift of my apartment, I thought to myself – this was the first time in many many years that I was feeling truly happy and liberated. I smiled and rang my bell. Aunty opened the door and asked, “How was your day?”, the same question she asked me everyday since she had come to stay with us. “Wonderful,” I replied, “Simply wonderful”
To be continued………..
Feedback can be sent to – I would love to hear from you. Don’t forget to Rate this Story.
Look out for the following episodes:
Becoming Anamika – Part 2 – Kannan Chettan has a guest.
Becoming Anamika – Part 3 – Tuitions with Ramanathan Sir
Becoming Anamika – Part 4 – Off to College and discovered by my room-mate
Becoming Anamika – Part 5 – Placement assistance
Becoming Anamika – Part 6 – My first job
COMMENTS