A crossdresser experience – Part 1

Hello to all the readers, I am Anupam, also known as Anupama, a 25-year-old male-to-female crossdresser. I started cross-dressing during my college days and now consider it a hobby. When in female mode, I prefer to be called Anupama. I am 5’5″ tall, have a wheatish complexion, soft skin with no facial hair, small breasts, and a round, soft bottom.

The story I am about to narrate happened when I moved from my hometown to a city to pursue a one-year Diploma course in Fashion Designing. I found a decent accommodation in a 1BHK flat, and the college was 5 km from my place. Initially, my mother accompanied me, and once things settled, she returned home. I had to commute to college by private auto rickshaw as I do not hold a valid driving license. I hired an auto on a monthly basis, and the name of the auto driver is Ravi, a 30-year-old married man, 5’6″ tall, and of medium build. He picked me up and dropped me off every day.

My daily routine involved attending college and then cross-dressing during the evenings. I utilized this leisure time to the fullest, as I had the secrecy and privacy to do so. I consider myself a beginner and am still learning the art of cross-dressing. I shared this secret with my female friends, and they supported me as well. It was more of the moral support that I required to continue on this journey.

While on the phone with friends, I used female gender words like “aungi,” “jaungi,” “dekhungi,” etc., and I communicated the same way even while in the auto. I knew Ravi was paying attention to these details, but I had a “no care” or “who cares” attitude, as we were both strangers.

My wardrobe includes sarees, suits, and kurtis. And after cross-dressing, I feel that there is an inner woman in me trying to come out. Everything was going smoothly; the only thing missing was sex. Even though I had a boyfriend back in my hometown, and we were in touch, the busy schedule didn’t permit us to meet. Anyways, I was in a new city and decided to explore myself, and this incident happened.

One Saturday, I purchased a party wear blouse for myself and asked Ravi to take me to a tailor for alterations. I gave the measurements, and we dropped the blouse to be ready in 2-3 days. It was a red party wear blouse with half sleeves, two shoulder straps, and a V-neck, which would go with any red saree.

The next day, my bad luck struck as my mother arrived and would stay for some time. On Monday, I got a call from the tailor saying it was ready before time. I couldn’t control my excitement and, after college, went immediately to collect it. My excitement reached its peak, and I wanted to try it on immediately, but where? I couldn’t do this at home, so I asked Ravi to take me to a mall or a hotel for an hour.

Ravi asked me the reason, and I knew he had doubts in his mind. I gave him a simple reason. He suggested a better option than a hotel or mall and insisted on going with it. He kept asking, and unable to decide, I was in two minds and unable to reply on time. Ravi jumped a signal and got caught by a traffic policeman. He had to pay a fine of 1000 Rs, and it was my fault; I felt bad for him.

Anyways, his idea was to save the money and review the blouse alteration work at his place. He was right; I should have listened to him earlier. I realized my mistake, but it was too late. Finally, he took me to his house, where he stayed alone, as his wife is 7 months pregnant. Immediately, I looked for his bedroom and locked the door.

Wow! The blouse looked magnificent, and it was a perfect fit. In the meantime, curious Ravi waited for me. After my trial, he prepared tea and asked me the whole story. Rather than making fake stories and telling a thousand lies, I decided to speak the truth. He got astonished as his doubts got cleared about me being a crossdresser. He asked for some proofs, and I showed him some of my pics.

I got some positive feedback like “sundar,” “sexy,” and “maal lag rahi,” which made me blush. I asked him to keep this as a secret. I felt joyous for myself but bad for him as he had to pay a 1000 Rs fine. After he dropped me, I reimbursed the fine, but he refused to accept. I requested him to keep it, but he ignored and asked me to throw him a party whenever suitable.

After my mother departed, I tried the blouse again. This time with makeup… and wow… I was looking stunning! Attractive enough to catch attention and sexy too. With this, my libido increased, and I started to feel the urgency to mate with someone. The month ended, and it was Ravi’s pay time. I remembered about the reimbursement I had to make. So on Sunday, I invited him for lunch at my place.

Ravi started texting me, and the first time, he asked for my pics. I thought he was in a drunk mode. And again the next day evening, he requested for the same. This time, I got carried away and sent two cropped pics. I got lusty comments and had actually seduced a sex-starved straight guy. He accepted the invite and insisted that I cross-dress as he wanted to see me in real. Oh my god! Seriously, this just lit me up.

On Sunday, I cross-dressed in the same V-neck red blouse with two shoulder straps. I used bra inserts to provide the breasts an instant lift, which created a very small cleavage. I wore a red embellished saree with a border, applied red lip gloss over my soft lips, kajal to make my eyes beautiful, wore a bracelet and a white pearl necklace, and colored my nails red. I looked stunning and hot! There was a knock on the door as Ravi arrived. He had lusty looks as his eyeballs gazed me from top to bottom.

Ravi: “Madam, app to bohot sundar lag rahi ho!” (Madam, you are looking beautiful!)

I was amazed to hear “Madam” for the first time.

Me: “Thank you!”

I served water, and my blouse cleavage caught his attention. I sat near him and handed over his pay along with an extra 1000 Rs. He didn’t accept and returned the extra 1000 Rs to me.

Me: “Bhayya, ye lelo, meri galti thi.” (Bro! Take this, it was my fault.)

Ravi: “Nahi, rehne do, Madam!” (No, leave it, Madam!)

Me: “Acha to fir kya loge?” (Then what will you take?)

Ravi: “Chai pilado, aur party kab karni hai?” (Give me tea, when is the party?)

Me: “Main chai, dudh sab pila dungi, bas ye rakhlo.” (I will serve you tea, milk, everything, please accept this.)

In the tussle to hand over, his hands touched my blouse, and I felt a shiver across my body. My saree pallo dropped, which left his mouth and eyes wide open.

Ravi: “Bohot sexy lag rahi ho!” (You are looking damn sexy!)

I was dumbstruck as my heart rate increased. He came near me and pulled me for a kiss. I did not hesitate as our lips locked. He sucked my red lips for some time and held me. His hands were exploring my open back. I felt like I was entering a woman’s zone. My hands caught his head, and I played with his hair. He moved to my neck region, planting passionate kisses all over. Oh, it was damn sexy. He was treating me like a woman.

Ravi: “Chalo na, bohot mann kar raha karne ka!” (Come on, I feel like doing it!)

Me: “(Smilingly) Mere saath?” (With me?)

Ravi: “Ha…control nahi ho raha.” (Yeah, you! I can’t control now.)

I held his hands and escorted him to my bedroom. He removed my blouse and released my small A-cup size breasts. His watery mouth moaned “SLHHHHH AAAHHHHH,” his strong palm pressed them, making me moan “OHHH.” My nipples were out, and he started to suck them one by one. I was in heaven.

He whispered, “Bohot din bad chhus raha hoo.”

He was getting to suck breasts after a long time. I could feel an erection in my penis as it was stuck in my panty.

Me: “OHHHS (and) AAHS,” all moans around.

He removed his clothes, and a well-built chest was driving me crazy for him. I could see a bulge in his underwear. He untied my saree and asked me to remove his underwear. As soon as it came down, out came his 6-inch-long dick; it was brown and clean-shaven. The veins were just running tight, making it a hard rock. The head leaked a little pre-cum, and my tongue sucked and licked the hole, starting to give him a blowjob. It was slow, and not all could fit in my mouth. He held my head and started to fuck my mouth with it. Ohh, I was just moaning and filled the dick with my saliva. My dick wasn’t able to control and could explode. I stopped.

His hot rod was 90-degree erect, and what a scene it was. I stood up, and Ravi caressed my stomach and fingers rolled in my navel. His hands created a sexy stimulation. I untied my petticoat and revealed the transparent lacy panty. And with no confusion, he removed it. He turned me, and my soft ass got exposed. He pressed the soft cheeks.

Ravi: “Chikni gaand hai, gaand me chodunga ab.” (You have a smooth ass, I will fuck your ass.)

Me: “Ha, please, gaand maro meri.” (Oh yeah! Please fuck my ass.)

I came in a doggy position, and he used Vaseline to lubricate my ass with his fingers. The first time, it was painful, “OUCH,” but no stopping now. Again, one more round was enough to lubricate it. He positioned his dick on my hole and stroked inside. I screamed, and with a couple more strokes, the entire dick went in a few seconds. I could feel the pain inside, and he started to fuck my ass.

With every stroke, I moaned in pleasure, “OOOOOOHHHHH.”

His body hairs added sensation. He changed his position and lifted his legs to push his dick further in. I screamed in pain and pleasure. He was fucking with great speed, making crazy sounds, “AAAAHHHH, OOOOHHHH.”

I lost body control as my hands and legs trembled, and I couldn’t control, and my dick exploded and sprinkled. With final strokes, he started to release his cum inside, and I could feel the hot white cum deposited inside my ass. We both exhausted lay for some time. His strong dick had just pleasured and satisfied me after a long time, and it was indeed a crazy session. Before I could get up, he got a call and left without saying a word.

To be continued in Part 2

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