Hi, I am Pawana. I am a 36-year-old, brown skinned, chubby crossdresser living in the US. I grew up in a small town in Karnataka and belonged to a well-known family in town. I was born with a silver spoon I must say, and I had everything growing up.
My sister who was much elder me was very beautiful young girl. She was in her teens when she was sent to faraway college for studies. Her absence from home made me very lonely and I missed her a lot when she was gone. My only best time of the day would be my own college timings. When that was over, I hated to go back home as I used to feel lonely at home.
I very much admired my sister. There was something about the way she walked, the way she talked, her body language, her make up, her dressing sense and all that. She was a total diva, I must say. Watching her so closely every day was slowly changing the way I thought about myself.
Let me first tell you how I look physically. As I am chubby, my body has very feminine looking features. I have perfect feminine figure, nice big girly ass, chest that looked like little breasts with large puffy areolas and nice bite sized nipples. I have a deep navel, nice thick thighs. My dick is so tiny that it almost looked like a clit and nothing more. All these features make me look and feel like a girl, a chubby girl. My body is so feminine that I avoid taking off my shirts in public.
When in college, I would go to bathroom to change my clothes during my karate or yoga classes while others just did it in classroom or even outside. I once had no option but to change my shirt in the ground and one of my seniors saw me and asked me if he can touch and squeeze my little tits, to which I said okay.
He just put his hands and gave them a good squeeze and I felt like my virginity was broken. Thank God, he didn’t ask me if he can suck on them. And after his first time touching me, it almost became a routine thing as we both started enjoying it whenever we got a chance. Sometimes, even his friends accompanied him, and I was enjoying it even more.
Slowly, it came a to point where he and his friends started inviting me over to their homes and played with my chubby feminine body for extended hours. They just loved squeezing my tits for hours and sucking on them. My tits had grown bigger as if like a young woman’s tits and nipples had grown bigger with bigger areolas. Almost like woman’s tits, they bounced and jiggled when I walked. Gravity was playing its part in making them bigger and fuller. And they, my seniors would take turns and have me over in their homes on a daily basis and use me like their little whore.
One day, one of my seniors while playing with me asked me if I would consider crossdressing, wearing bra and panties, and wearing girl’s clothes as it would make me look even more sexy and make him more horny at the same time. I reluctantly said yes not knowing what to answer and went home that evening thinking about it all the way.
When I reached home, I lied down in my bed thinking about it and all of a sudden it flashed to my mind that my sister’s wardrobe would be the perfect place to start crossdressing. I went to her empty room that night and quietly opened her cupboard and found a whole lot of selections of clothes to wear. From tops to crop tops, midis to mini, salwar kameez, lehenga choli, half-slips, full slips and even her swim suits.
Best part of them all were her old bras and panties, a variety of them in all colors and designs, and also found few stocking and some sexy shoes. At that point, I felt like I was in the best place on earth.
I slowly closed the door and tried each and every piece of cloth that she had in her closet. Those bras were so perfect for my tits. My tits felt secured in those cups and my femineity had found a new angle.
The next day I wore bra and panties and took a set of mini skirt and a sexy top in my bag and went to my senior’s house who had asked to cross-dress. And as I entered, to my surprise, I saw the other two seniors also there. And I knew at that very moment that it was going to be a long yet a memorable day.
They asked me if I got any sexy dress to wear, and I replied yes. And then I asked to wait for 5 minutes while I get ready. I went into a room, wore the mini skirt and the top I had taken along with me. I was looking sexy as fuck. And as I came out of the room, all 3 were staring at me like hungry wolves.
They came near me, didn’t say a word and one of them held me from behind, gripped me with one hand on my belly and the other under my left tit. The second one put one of his hands on my right tit. The third one put both his hands on my fat ass and started kissing me. And they all started fondling my tits, squeezing my ass, thrusting their dicks towards my chubby body.
That day, all 3 sucked and squeezed my tits like there was no tomorrow. They made me go so crazy that my tiny little dick (clit) was dripping juices. I had the best orgasm ever, and that day for the first time I sucked dick – not one but three. I sucked them so well that I was surprised to know how good of a cock sucker I was. I sucked all three dicks like an experienced whore. And for the first time, I even tasted cum and swallowed. It was too many firsts on that day.
As years went by, I had become a very good crossdresser and a slut sucking dicks whenever and wherever I can. I had more dicks to take care of along with my 3 sexy handsome seniors. I was sucking my professor, my distant relative uncle, a rowdy man from my area, and even sucked a cop.
My breasts at that point of time were bigger and were able to squeeze a dick in between them. I gave blowjobs, titty fuck, got ass fucked, and what not. As time went by, my seniors were gone. They all got jobs, got married and went their own way. And that point of time, I almost had 25 other men that I was servicing.
Few years past, I perceived a great career and I was still sucking, getting fucked, getting gangbanged and even took a cum shower in a bukkake party. I was just born to make men happy.
I am currently in America. I am almost a fulltime crossdresser now. I have completely transformed my body and I can proudly call myself a woman now. I still get all the sexual attention I need but my partners have changed. I am totally into black men these days, love them big black cocks and love being a whore they want me to be. Like they say, ”once you go black, you will never go back.”
After my work, in the evening hours, I go to motels, hotels, parks, cinema halls, or where ever they want me to come. I just go and give them the best service they need. After all the hard work, when they shoot heavy cum across my lips and my face, I feel like I am a real woman. Making a man cum is the best thing for me in my life.
From a smalltown whore to a bigtime city whore, my journey as a crossdresser has been phenomenal. A big shout out to my seniors who made me a woman. Love you guy, wherever you guys are, I will always be your whore.