Indian Gay Sex Story: Date with a crossdresser

Indian Gay Sex Story: Date with a crossdresser

Indian Gay Sex Story: Since the time I was still teenager, I think I was attracted to the idea of being a girl. I used to spend my alone time fantasizing about being a girl and the things that I would do if I was one. I think I even prayed for a while to be magically transformed into one but alas, it wasn’t enough.

I always used to take the first opportunity to dress up in my sister’s clothes and wear makeup whenever I was alone. Though it was not perfect in the beginning, I slowly perfected the art of applying makeup and dressing myself up. I continued to dress myself up right up until I finished high school. After high school, the circumstances were bad and I had to find some work. I moved to another Chennai and got a job there in a very reputed call centre.

The pay was great and I was enjoying life in the big city. I was living alone at this time in a cosy and comfortable 1 bedroom apartment. It gave me all the privacy I needed. Slowly as things began to improve on the home front due to my efforts, I reduced the stress that I was taking and started to loosen up. Now I had all the time in the world. Slowly I started buying up clothes – saris, salwars, frilly, beautiful tops, tights jeans, half-saris, long skirts etc.

I also bought makeup and a beautiful, expensive wig (my hair was still short). I started cross dressing at home almost every day. Every session was elaborate and grand. I was very much in love with myself and the world as a whole. One day, while browsing online, it struck me that I was alone in the city and I was virtually anonymous. I could maybe meet up with someone who would treat me like a girl, who was comfortable with me, the way I was-if only for a night.

I started yearning and craving for male company. I signed up and created accounts in a numbers of adult sites and in Yahoo Messenger, Initially, the response was really bad. I was abused online, people called me bad words and I almost gave up when one day there was an email in my Inbox. It was from a guy who had read my Facebook Profile (I had created one exclusively for this purpose).

He introduced himself as Rajeev from Chennai. He said that he was the Chief Technology Architect of one of the leading IT companies in India. It seems that he was on the look out for someone just like me and was interested in meeting up. He mentioned both his Phone number and his Address in the mail. The way his mail was worded made me curious. I decided to give it a try. Very cautious, on a Thursday evening, I called him on his mobile.

He was extremely polite and courteous. He was a gentleman in every respect. He said that he was 38 years old and was never married. He was very straight forward and eager to meet up. We scheduled a meeting for the next day to meet at Taj Coromandel for lunch. The following day, I reached there at the designated time. He was waiting for me at the lobby. We had a fun filled lunch. He was easy going, humorous and fun to be with.

He kept showering me with a lot of compliments. I was shy and very happy at the same time. After lunch, he asked me if he could drop me home. I agreed. On the drive back we talked about our jobs, life, likes and dislikes and everything else under the sun. It seemed like we’d known each other for ages. Once we reached my apartment, I asked him if he wanted to come in. He agreed and we went to my apartment.

He loved the way I had decorated and maintained my apartment. We sat down and had a couple of drinks and talked about this and that. Out of the blue, he asked me whether I liked him. I said “Of course, Rajeev”. Rajeev replied, “From the time I read your profile, I’ve been attracted to you. At that time I thought it was just a fancy of mine but when I saw you today, I was blown away.” I said, “Don’t make fun of me Rajeev.

I know I’m not one of the best looking guys around”. To which he said, “Who said anything about being a guy. You have to be the most beautiful girl I’ve ever seen.”. I was shocked, “Oh Come on Rajeev. Stop kidding around.” Rajeev – Honestly Rohit. I’m telling you the truth. I’ve been dying to take you in my arms and treat you like you really should be treated.” I was speechless.

All that I wanted was gradually unfolding before me. Seeing my silence, Rajeev requested “If I may, and only if you are Ok with it, can u dress up for me; I’d like to see you in your true glory”. I smiled and reluctantly agreed. “Rajeev, this will be the first time that I’d be coming dressed as a girl in front of someone. I’m a little nervous.” “Don’t be. I already like you a lot. Nothing you can do can turn me back now.” I said Ok. Give me 20 mins. He agreed.

I went into my room leaving him in the hall. I went to the bathroom and started applying hair removal cream all over and 10 minutes later got rid of all the unwanted hair. I had a bath and came out. I was feeling wonderful. I picked a black lacey bra and a matching panty. I wore them and adjusted my chest to get a small cleavage. Once that was done, I took out a red saree and a matching blouse.

As I put those on, I couldnt but help thinking as to what was going to happen today. I was literally living in my dream. Once I wore the sari, I wore the wig correctly and started applying makeup. Once satisfied that it was perfect, I sashayed a couple of times in front of the mirror. Oh! What a wonderful feeling.I knocked on the door and told Rajeev that I was about to come out. Rajeev said he was ready.

I opened the door and stepped out. There he was sitting with his mouth wide open. “You cannot be the person who went inside”, he said. “You are truly beautiful. Come here come sit next to me.” And I went. He started kissing me slowly all over my face and neck. I was enjoying myself immensely. His one hand was constantly fondling my nipple and pinching it through the blouse. He gently removed the pallu of the sari and pushed me down on the sofa.

He was over me and licking my neck and the little cleavage. He slowly went down and lick my navel. He licked my armpits and soon, there wasn’t and inch on my upper body that his sensuous tongue hadn’t passed over. I shuddered with pleasure and moaned with slightly parted lips. Rajeev slowly untied my sari and let it slip to the floor. He then proceeded to remove my blouse and my petticoat.

I was instantly aroused beyond comprehension. I wanted him. I was his and I needed him with a passion so strong that it was beyond words. ‘Control’ was a word that no longer existed in my vocabulary. I turned him over and came on top. I pulled out his t-shirt and tugged at his belt. I pulled don’t his jeans and his underwear in a frenzy. He had a huge hard-on. His cock, which was already oozing pre cum was easily 7 inches long and it was very very thick.

I put my mouth over it and heard a slight moan from him. In that instant I knew that what I was doing had to be right. Slowly, I started sucking on his cock. It was amazing. I licked his balls too and he loved this. I snaked my body over his and squirmed on top of him, all the while whispering “Rajeev darling, I’m yours.” He rolled up his eyes with pleasure and moaned “Yes Yes.

Slowly I got up, held his cock and led him to the bedroom. I wanted to be fucked by this man now! I wanted to feel his cock in my virgin asshole right now. There was ajar of maple syrup by the bedstand. I took a sip of this in my mouth and let it stay in there for sometime. Without swallowing it, I went down on my knees and took his cock into my sticky, maple syrup filled mouth. The combination of the warmth, the stickiness and the sucking was too much and he came in my mouth.

Oh my! It was never ending torrents of cum. I gagged but swallowed the warm liquid along with the syrup. It was delicious. He said, “I need to fuck you now baby. I want you.” “I’m all yours”, I said. I turned over and got on all fours. He dipped his index finger in the jar of maple syrup and proceeded to finger my asshole. Once it was sufficiently lubricated, He brought the head of his cock to the opening. This was it. The climax of my fantasy and it was going to be fulfilled.

Rajeev slowly thrust his cock in. Inch-by-inch he inserted it slowly, waiting for me to get accustomed to his cock. It was unbelievably big and long but in the end, he managed to get it all in.

Then he began fucking my ass. “You have an amazing ass, you’re my bitch, my own property and I’m going to fuck you hard now. Tell me how much you want it.”Aaaah! Please don’t stop Rajeev. I’m your bitch.Use me, Abuse me, do what you want but don’t stop fucking me. Oh, it’s so wonderful”. Slowly he increased his momentum and was fucking me with such force and frenzy that I thought I was going to faint with the sheer pleasure and delight. I was screaming and begging him to continue fucking. He fucked and fucked me very hard and went on and on. My, he was a machine and had amazing stamina.

Fuck me Rajeev. I’m your slut and I need your cum. I’ve been waiting for your cum. Fuck me, fuck me hard!please!” This drove him into a frenzy and he grabbed my shoulders and fucked my ass furiously. My ass was leaking liquid and my ass was ready to explode. With a yell and a whoop of joy, he screamed “yes, yes, yes and shot hot streams of cum into my ass. He filled up my ass to the brim with his cum.

Hot and wild Indian gay sex story of a crossdresser enjoying a sexy date with a horny and romantic desi hunk!

Exhausted, he collapsed on top of me with his enormous but reducing cock still inside me. I too exploded and my cum showered all over the bed. I fell on top of it when he collapsed on top of me. So there I was lying in a pool of cum, with cum in my ass, the taste of cum in my mouth, having been fucked out of my wits by this delicious man. The woman inside me was at peace, finally.

This was paradise and I never wanted to leave it. Rajeev spent the rest of the night with me. We spent the night talking, fucking, talking some more followed by more fucking. He left in the morning with promises to meet up again. He left me feeling satisfied as a woman and rejuvenated as a man. So this is my story not the end, but a new beginning.