It was a Saturday morning and I had the whole week for myself. After coming late Friday night working overtime in the office, I had kept the weekend to dress up in the gorgeous sarees and look for some fun on the dating apps.
As I was sitting on the couch right swiping everyone, one match popped up saying the usual, “Hi!”. Even I replied with the same enthusiasm, “hey!”. At first we both were very formal, but after few chats, we became friends. He asked me as to what I was looking on the dating app, and as usual I answered not hookups or one night stand, but in my heart I knew just can’t afford a genuine relationship with someone as I would be cheating on my wife! Not that hookup won’t be cheating but I just want to embrace my womanhood once, feel like a woman, have the pleasure of satisfying a man.
After some conversation, he asked to meet but as I’m a closet crossdresser I refused to meet anywhere outside. I could sense that he was sad and wanted to meet badly, more than me. So, I invited him for dinner and told him strictly to message me when he comes at the door as no one in the society knows that I’m a crossdresser.
As the day was passing by, I was just thinking what to wear. Confused between western dresses or sarees, I was just not able to figure out. To tell you, I have 2 western dresses and 8-9 sarees. Sarees are just love and what better way to flaunt your curves. I’m not that tall being 5’6” gives me an average height for a woman these days, and a little bit chubby I am. I decided to wear a saree as I would be most comfortable in it.
Later in the evening, I decided to shave my body and after that applied body lotion to make my body softer. I opted for a dotted black color sleeveless blouse and a red color saree to make me look all sexy. I didn’t know how to cook so I ordered few starters and paneer dish on Zomato expecting the delivery guy would arrive after my date comes.
It was almost 7 in the evening, I was waiting eagerly for him to come. At strict 7 pm, I received a message, “I’m at the door, please open”. I was extremely nervous as this was the first time I was about to meet a stranger being crossdressed. I took some deep breaths and walked towards the main door. I opened the door and I could see a tall handsome fairly looking guy with a nicely trimmed beard. He was just in an awe and came in giving me a bouquet. After a few seconds of weird silence, he complimented me on my looks and how beautiful I’m looking. I just rolled my finger through my wig saying, “Thank you”!
I asked him if he would like to drink anything, he just nodded in yes. After few drinks the bell rang and I asked him to attend the door as it would be the delivery guy. He received the parcel from Zomato delivery guy and handed over to me. I quickly went to the kitchen to open it, opened the drawer to take out the dishes. As I was opening the parcel, I sensed a touch at my back. He was rolling his fingers through my navel, tickling me. I just felt the sensation going over my body and didn’t say a word, this made him more confident and he hugged me very tightly from behind. He turned me around and said, “itni bhi kya jaldi hai khane ki, main kahi bhaga toh nahi ja raha!” After saying this he kissed me on my lips and I was just absorbing the situation. It was happening to me very first time, all this I had just dreamt it. He kissed me again and this time I kissed him back. We two were kissing so passionately just like a couple. He then started kissing all over, starting with the neck, going around my ears. Oh God! When he was kissing me around my ears, I became so aroused at that moment that I just started rubbing his manhood area. We were taking deep breaths, and he opened his zip indicating me to do the job. I bent down on my knees and took that thick long rod and started stroking it. I had never imagined myself doing this because I had always been at the other end of it with my wife having the pleasure of stroking it. It was my turn to experience it and after stroking it for few times, he said “take it”. I wasted no time and took it in my mouth and gave him a blow job. At first it felt ridiculous and I just wanted to throw up but he kept insisting and then after few strokes I started enjoying like it was my destiny. It was some experience that I can never explain in my life. A feeling so strong that made us bond even more. He took me in his arms and took me to the hall.
We both kissed each other passionately on the sofa. He unhooked my blouse, kissed my arms slowly, caressed my fake breasts sometimes being too harsh on them making my chest feel the pain. He threw my blouse, my padded bra and started kissing my body. I also responded with same passion. After few minutes, he undressed me and now we both were naked. He could see my hard dick, wanting to play with it but I told him not to as I just wanted to feel like a woman. But he insisted and after several rejections, he just started stroking it. I was a horny bitch at that moment who was getting a hand job. My moans indicated that I was utmost enjoying the experience. He said, “it is not just me who should be enjoying, we both should enjoy Kyuki taali sirf ek haath se nahi bajti”. My tool was now about to throw up and I was about to cum, he didn’t take it in his mouth like my wife would do instead he just continued with the stroke ending my cum getting released like water releasing from a water pipe.
I could see his tool very hard and I just took it in my mouth desperately wanting to give him some pleasure. He started moaning, “oh yes! Oh yeah!” This made me feel more horny. It continued for a bit and then he asked me to turn over. I understood what he meant and I just obeyed his instructions. It was time to embrace my feminine side and feel what it is like to be a woman. He inserted his huge rod in my asshole. As soon he inserted, I shouted in pain. He realised that in all the excitement he did not apply Vaseline. I told him the directions to the Vaseline, after applying the lotion he started inserting again but this time pain was bearable. After few strokes, I started enjoying this feeling and I said, “aur zor se”. He obliged and increased the speed making me feel out of the world.
After the hot session, he got up and wore his boxers. I was in such a pain that I didn’t want to get up and lied on the sofa. He came towards me, kissed me on my forehead and said, “apne mujhe aisa sukh diya hai Aaj jise mujhe kisi ne itne months mein nahi diya, aap aaram karo main khana lagata hu.” I was in utter shock that I was able to please him in my very first attempt. I felt like a happy young woman.
He brought only one dish with the roti, salad and paneer sabzi. He took one bite and then tore one small piece, applied it on the paneer and offered me. He was feeding me, such a gentleman. I rolled my arms around his arms and we were sitting just like another Boyfriend Girlfriend. Amidst all this, I asked him why do you like crossdressers, you look so smart, you’re a good looking guy. I mean you could get a very hot girlfriend anytime, so why a crossdresser? He answered that from his childhood he was attracted to a different type of woman, a man wearing women clothes aroused him. It started with Aunty No. 1 movie in which Govinda played a woman’s role. Then followed by Chachi 420 movie. And it continued. He always wished to be with a crossdresser but the society doesn’t accept this to be normal. He said that he has a girlfriend but she doesn’t know about his secret desires. He also said that he never felt physically attracted towards her. Just when he was saying personal things, my phone rang and it was written, “Wife calling”.