Crossdresser Turns Gay To Seduce His Tailor

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Hi all! I am a family man with a loving wife, but she doesn’t know about my crossdressing. It just so happened that she had gone to her mother’s place during her pregnancy, and I got ample time for my crossdressing.

I did all of my shopping on Myntra and bought myself some nice soft satin sarees, dresses, gowns, tops, high-heel shoes, a makeup kit, perfumes, and loads of bras. I was waiting for the delivery like a curious kid waits for their birthday gifts.

Finally, the day arrived and the Myntra package deliveries started. I unboxed everything and felt the touch of all the soft materials, smelled them, and tried them all on. When I did not fit into some of the dresses, I was disappointed, but I decided to have them exchanged was.

For the sarees, I was going to need blouses, so I went to a local shop nearby and searched for some readymade blouses. None of the blouses they had were of my size, but I finally found one which I could have altered.

When the tailor asked me for the measurements for alteration, I asked him to alter it to my size. He looked stunned for a moment, and then started laughing. I told him that I needed the blouse for a drama in which I would have to wear the blouse. He looked skeptical, but then he agreed and took my measurements and altered it.

When he saw that I was quite anxious and shy, he must have understood that the blouse was not for any drama. But he didn’t say anything about it, and I was also quiet. He altered the blouse, and handed it to me.

When I got home with the blouse, I started draping a saree after watching several video tutorials. First, I put on some nice, soft satin panties, and then a figure-fitting petticoat from Zivame, which was very sexy. I had also purchased a waist shaper and hip pads, which gave me good support and a well-defined shape to my waist and hips.

Then I wore the blouse. I admired the tailor a lot for the fitting he had done. It was awesome! Next, I started draping the saree and it came out to be pretty perfect. I wore some bangles and put on some bright red matte lipstick. Next, I wore a wig and applied kajal and mascara. Because I had my ears pierced, I wore some pretty, heavy jhumki earrings and roamed around the whole house like a beautiful little girl.

I was so excited from handling those bangles and walking around holding my saree, and my jumping breasts that I was going crazy and started touching myself. Later, I decided to go further, as I had a lot of good times waiting ahead before my wife would return.

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Now, I got dressed in sexy outfits and roamed around the home, cooked, did all the housework until I was tired and then I changed into a nighty. I decided to stay in girls’ clothes since it was the weekend and I didn’t have to go anywhere. All dressed up, I went through some social media and then dozed off.

The next morning, I wanted to get some more blouses stitched for all the sarees I had purchased on Myntra. I also wanted some dresses stitched. So, I gathered all the blouse pieces and changed into my male clothes and went to the tailor to ask about the stitching.

At the store, I had to wait, as there was a queue and some other customers. Once they had all left, I went to the tailor, and our conversation went like this:

Tailor: Hi bhaiyya, what do you want?
Me: Please stitch these blouses for me.

And then I gave him my measurements from the day before.

Tailor: (With a long stare) I don’t stitch women’s clothes.
Me: Bhaiyya, I told you. It’s for my drama. Charge me extra, but please, I need these blouses.

Tailor: I already stitched you a blouse for your drama yesterday.
Me: We have a lot of costume changes in the drama, so I need more blouses.

Tailor: Sorry bhaiyya, I can’t stitch these for you. Please leave.

Then, I gave him a slip with a 2000 rupee note and smiled at him. He also acknowledged me with a smile and I returned to my home. On the slip, I had written asking him to come to my place if he wished to see the drama rehearsal himself, and I had mentioned my address.

It was a Saturday and I was feeling pretty lazy. I wanted to feel completely feminine and have a full womanly experience, so I decided to wear my wife’s sanitary napkins. It was a different experience, so soft, and the way it touched my balls was so satisfying, I felt like I was in heaven.

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Then, I started doing some household chores, when I heard my doorbell ring. I got a little concerned, as I was in a nighty and a wig and was wearing makeup. I looked through the windows to see who it was and saw that it was the tailor.

When I opened the door, he kept looking at me for two minutes, and then he asked me to call my husband. I started laughing and told him that I stay alone. Then, he showed me the slip I had given him, so I took him inside and closed the door.

When we were inside, I told him that he was looking for me. He was shocked and said that it was hard to differentiate me from a real woman.

Then I asked him whether he would stitch the blouse for me now.

Tailor: You didn’t rehearse for me. How can I believe you?

Me: I am a crossdresser. Please understand. Charge double if you want.
Tailor: Oh! Ok, I get it. You’re like a transgender person, right?

Me: No bhaiyya, this is different. Please just stitch the blouses for me.
Tailor: I will charge you less than the market price, but I have a condition.

Me: What is it? (My heart was beating at a hundred beats per minute)
Tailor: You must try the blouse with the saree in front of me, in the shop when I stitch it.

Me: That’s not possible, bhaiyya, please understand. I will give you double the price.
Tailor: I can’t compromise on my condition.

He was staring at my huge boobs and sexy lips. I must say, I really looked like a sexy, hot lady when cross-dressed. Any male would want to take me to his bed. Noticing the bulge in his pants, I went closer to him and took his hand in mine and started rubbing it. I asked him again, “Please, bhaiyya, please, please, please?”

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The tailor was trying to approach my boob, but was stammering, saying, “No, no, no, no!” So I took his hand, and put it on my boobs and started making him squeeze them.

The tailor’s face lit up, and with a glow on his face, he was pumping my boobs. So I said again, “Please stitch it?”

Tailor: I will change the condition. I will get those blouses to your home. You will wear them here, in front of me, with your sarees.

I looked like the emoji with hearts in its eyes and agreed excitedly.

He showed me loads of patterns for my blouses. As he was showing me the patterns, he kept his leg on my thighs and started massaging it.

I chose sleeveless, mega sleeve, and 3/4th sleeve patterns for my blouses. I wanted tie-up front closures. For the other blouses, I chose bells and some other work. On one blouse, he told me he would design a piece that I just needed to just tie onto my chest. I said ok and paid him the advance.

He told me he’d visit me again with the blouses in three days and left.

After getting intimate with him that day, I wanted to get fucked by him in my ass, and I wanted to look good in my sexy new blouses. I informed my manager that I wouldn’t come to work on Tuesday or Wednesday and started preparing for my grand fuck session.

Wait for the next part of my story for further updates…

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