Hello friends. My name is Ankit Dubey. I’m 25 years old. I am originally from Patna. I am an engineer and work at a software company in Mumbai.
My height is 5ft 6. I have very fair skin. I have had very little body hair since childhood, and my facial hair growth is slow. Nevertheless, I keep my body hair-free, and my face is always clean-shaven.
I usually keep my hair cut short. My facial features are somewhat feminine. I have a lean body and make it a point to keep fit but not put on too much muscle. My ass is a little pronounced and prominent for a man. Due to my body structure and feminine features, I am somewhat of a beautiful man.
This body type and features help me when I cross-dress. Once I put on my wig and a little makeup and get into feminine clothes, you cannot tell I am a man. I can pass off as a very beautiful woman. I am thankful to God for this attribute.
My affair with cross-dressing started in my childhood. I went to an all-boys college. Since we were no girls, boys had to play the female roles. Since I was fair and slender built, my teacher picked me for the female role. For the role, I had to wear girl’s clothes.
I felt good when I dressed in girl’s clothes and looked at myself in the mirror. I felt beautiful. I enjoyed the 2 weeks of rehearsal and final performance as a female. The same happened at next year’s annual day as well. I was chosen for the role of a female again.
This time I realized that I liked wearing female clothes. All through college, I did female characters and got to wear girl’s clothes. I was so happy with it that I looked forward to the annual day every year.
Later I had to change my college because my father got transferred. This time I went to a co-ed college. As there were girls, they did the female roles, and I didn’t get to wear girls’ clothes.
I had an elder sister at home. Sometimes, when I was alone, I would take her clothes and wear them. I felt good. I felt free. I enjoyed wearing girls’ clothes. But I never let anybody find out about this. I was afraid I would be ridiculed and made fun of by family and friends.
Junior college was also when I realized I was gay. While everyone around me was getting into heterosexual relationships, I was not attracted to girls. I hid this aspect as well. I did not tell anybody about my disposition.
After college, I joined engineering and moved back to Patna. And even in college, I kept it a secret. I realized I could not be who I wanted to be if I stayed home. That’s when I got a job offer at a software company in Mumbai to be a software developer. I decided that this was my chance and took the job.
I moved to Mumbai after my graduation in 2019. Mumbai is a big city. Here you can be yourself. People don’t have the time to care about others. Everyone is busy, and nobody is nosy. None of my friends or relatives lived in Mumbai. So, it was perfect.
My office was located in Parel. To ensure I had privacy at home, I rented an apartment in Powai, far from my office. This way, none of my colleagues ever came home. I could live two separate lives.
For the first time in my life, I experienced a freedom I never had. My 2 BHK apartment was in a newly built apartment complex with 4 blocks. Each block had more than 80 apartments, ensuring complete anonymity.
During my first week in Mumbai, I went shopping at a mall. I picked out clothes for the office and added a few women’s clothing items, including a dress and salwar suits. After I came back, I tried on the female clothes.
I became overjoyed as I wore them and looked at myself in the mirror. A strange happiness emanated from within. It was beautiful. I have always felt something was amiss, but right then, standing in those clothes, I felt complete. I realized that I felt like a woman within.
That explained my attraction toward men. I was a woman trapped in a man’s body. After that day, I started living two lives. One as Ankit that the world knows about. The other was Ankita which was my secret.
When I was alone, I started behaving like a woman, wearing only women’s clothes. I removed my body hair to have smooth hairless skin like other women. To hide this from the outside world, I covered my entire body with full-length sleeved shirts and pants when I dressed up as a man.
After a few weeks, I again went shopping and bought more articles of women’s clothing like bras, panties, sarees, and lehengas. With time, I even purchased makeup sets and started experimenting with them.
I had ensured that my dual lives never collided. This dual life continued seamlessly. I would leave for work as Ankit. I behaved like a normal man at work. I gelled with my colleagues, and all was good. After work, I would return home, change into women’s clothing, and become Ankita.
After a few months, I started going out of my house as Ankita. Under cover of darkness, it was nearly impossible to make out that I was a man. Slowly, I mastered the art of makeup. This gave me the confidence to become Ankita even during the day. When I went out as Ankita, I felt like a caged bird let free.
I would go to malls, pubs, and restaurants like Ankita. Since I looked like a beautiful woman, many men would ogle at me. I liked the male gaze upon me. It further bolstered my confidence. I truly felt like a woman this way. I had never been happier in my life.
There was the sadness that I could never truly become a woman. Nevertheless, I was happy that I got to be and feel like a woman for a part of my life. I wasn’t openly gay to the people I knew. But under Mumbai’s anonymity, I started exploring my gay side.
I met a few guys and even had sexual relations with them. But, nothing became serious because even gay people have a problem with cross-dressers. Over time I resigned to the fact that I could not have everything. So I had casual hookups with other men from time to time.
But most of the time, I found pleasure in being Ankita. The pandemic was a blessing in disguise for me. During the two pandemic years, although I was stuck indoors, I experienced freedom like never before. I became and remained Ankita for long durations. Sometimes weeks together.
During the pandemic, with the additional savings in my income, I bought more female accessories, clothing items and other products to make me look more feminine. I even purchased vibrators and dildos to pleasure myself.
Since then, my lifestyle has changed. I become Ankit when my maid comes in the morning and remain until I return home from work. As soon as I return, I change into women’s clothes entirely and become Ankita until the next morning. This was my life. I was happy and enjoyed it.
In June 2022, an incident occurred that transformed my life. My company had gotten a very big project, and I was a part of it. However, we could not crack one major code of the project, and the deadline was approaching fast.
Thankfully, I could figure out a solution and develop a code that was satisfactory to the client. This gave my company a lot of business. My project manager was so impressed with the work that he recommended his boss give me a bonus.
His boss was Shekhar Mishra. He had recently been transferred from the Delhi office. He called me to his cabin, appreciated my work, and promised me a bonus. I was happy with my professional success and decided to enjoy the night.
Moreover, it was Friday. I reached home and dressed up as Ankita. I wore a maroon satin bra and panty set. I stuffed the bra with breast forms. Over which I wore a wine-colored cocktail dress. I applied the makeup, wore a wig, added accessories, put on heels, and got ready.
As Ankita, I use Uber to travel around. I decided to go to a pub in Versova. I enjoyed myself. I drank, ate, and danced to my heart’s content. Close to midnight, I decided to head back home. I got out of the pub, booked a cab, and waited for it to arrive.
While waiting, I saw a group of three men come out of a nearby restaurant. They seemed to be a little drunk. They came close to me. I could sense that they were eyeing me. I enjoyed the attention I was getting as Ankita.
One of them said, Hey, beautiful. Do you need any help? I turned towards them, smiled and said, No, thank you. Just waiting for a cab.
As soon as I turned, I realized that one of them was Shekhar sir. In all these years, I had never met anyone from my other life while I was Ankita. I was shocked and turned away.
However, Shekhar saw me and said, “You look familiar. I have seen you somewhere. Such beauty. But I can’t remember where.” I looked to the other side and started to walk away.
Just as I took a few steps, a cab stopped near me. The driver asked, “Ankita?” I got into the cab and said, “Let’s go.” As the car drove away, I noticed that Shekhar sir was still staring at me and his eyes followed the car.
I had met Shekhar sir only once and hoped he would not figure out it was me. He seemed a little drunk, so I thought there was no chance he would figure it out. I didn’t think about it again.
Next week, as usual, I went to the office. On Thursday after lunchtime, the office boy came to my cubicle and said, Shekhar sir is calling you.
Shekhar sir’s cabin was on another floor. As I walked to his cabin, I wondered why he was calling me. I entered his cabin, and he asked me to sit down. He once again appreciated my work efforts and started a casual conversation. He spoke about a restaurant he went to for dinner last Friday in Versova. He asked me whether I had been there.
At the mention of last Friday, I became conscious, and sweat trickled down my forehead. Shekhar sir noticed this and smirked. I said, “I hadn’t,” made an excuse about pending work and excused myself from his cabin. As I was leaving, he called out and said, “Ankit, let’s grab a beer tomorrow night. My treat.”
I started to say that I was busy, but he cut me off and said, No excuses. Your boss is calling you. I sighed and agreed to it. For the next two days, I was worried about whether Shekhar sir had figured it out and what he would do. I was afraid he would tell people at work. This fear turned me restless. I decided that I would vehemently deny any inferences he made.
On Friday night after work, we went to Toit, a pub near the office. We found a booth in one corner, sat down, and placed our orders. I was a little anxious and jittery. But as it turned out, he was quite open-minded and non-judgemental. He made me feel at ease. He approached the topic very tactfully.
Initially, I denied it, but after his reassurance, I accepted it and spoke about my secret life. It was such a relief to be able to speak openly about it. I asked him how he realized it was me. He said that initially, he didn’t. But the image of a beautiful woman and her name was stuck in his head.
Then on Thursday, my name was mentioned during a meeting, and it struck him. He had called me to confirm his suspicion.
I asked him to keep it a secret. He again reassured me that he would not utter a single word about it to anyone. I then told him my story, everything from the college play to moving to Mumbai and my current lifestyle.
Shekhar: So, nobody has found out about it? What about your neighbors and other people?
Me: Mumbai is magical that way. Nobody has time to care. And since I look like a woman like Ankita, nobody bothers about it.
Shekhar: That is true. You are indeed quite beautiful. You looked very hot last week.
I thanked him for his compliment.
Shekhar: What about family and friends?
Me: Nobody else knows. You’re the only one. A few men who I had flings with in Mumbai know. But nobody else matters. All the things I use as Ankita get locked up in a cupboard when somebody visits me. I say the house owner has his things in the cupboard and that he has the key. Nobody bothers after that.
Shekhar: You lead a dual life so well. I’m quite impressed. So, if you don’t mind me asking, do you identify as a gay man?
Me: You could say I’m gay. Seeing how I’m a man and I am attracted to other men. But I feel like a woman inside. So, it’s a bit weird. Most gay men don’t understand my need to cross-dress, either.
Shekhar sir gave an understanding nod. We continued with our conversation and food. I asked about his life. He was 39 years old and was married with two kids. His wife and kids stay in Delhi. They didn’t shift with him after his transfer because the older child was in school.
We finished our dinner and went our separate ways. Before leaving, I asked to keep everything a secret.
Shekhar: Don’t worry, Ankit. My lips are sealed.
Me: Thank you so much, Shekhar sir.
Shekhar: Please call me Shekhar. Stop this ‘sir’ nonsense.
Me: (laughing) Okay. Goodnight Shekhar.
Thankfully Shekhar was true to his word. He never mentioned it to anyone at the office. Normal life resumed.
About 5-6 weeks later, I went to DB Mall in Juhu on a Saturday evening. I had to buy a few clothes and makeup and decided to have dinner at the food court. I heard someone call my name and looked around. I saw Shekhar waving at me from one of the tables. He was having his dinner. I joined him, exchanged pleasantries, and we had dinner together.
After our meal, I got up to go home.
Shekhar: So, where are you headed? Got any plans?
Me: No plans as such. Going straight home.
Shekhar: Oh. If you have no plans, come home, it’s close by. Let’s have a drink. Will enjoy the company.
I tried to say no, but he insisted, and I agreed. His house was less than 10 minutes from the mall, so we walked the distance. When we reached, he asked me to sit on the sofa while he put away his bags and got us drinks.
A few minutes later, he came with a bottle of Teachers, two glasses, ice, soda, and snacks and kept them on the coffee table. He then sat down on the other side of the 3-seater sofa. He prepared the whiskey and gave me a glass. We started drinking and having a conversation. It was easy to talk to him, and we had a good time. One peg led to another.
Shekhar: I still can’t believe Ankita and Ankit are the same person. I mean, look at you now. You’re so beautiful. Nobody can tell you’re a man. Look, you’re even sitting like a lady. And your breasts and figure, everything looks so real.
Me: Thank you so much for your compliments. The pandemic helped me. I had money and time to experiment and figure out what suited me best.
Shekhar: You’re probably the only person I know who liked the pandemic and the lockdown.
Me: Yes. These breasts you think are real are a combination of makeup and silicone products. Found them during the pandemic. They fit so perfectly.
Shekhar was right. I looked stunning, dressed in a bottle green full-length kurti. With the charm of makeup and accessories, nobody could say I wasn’t one of the most beautiful women they had ever met.
The conversation continued about my looks and experiences. Before we knew it, we had finished another couple of drinks each. I was starting to get buzzed. I spoke about my insecurity of never being a complete woman and how I could not find someone to accept me. How I could never be a wife or a mother.
He listened to me patiently and gave understanding, reassuring nods, and encouragement. Later, being a little drunk, I spoke about my flings and how I use dildos and vibrators for pleasure.
Shekhar: See. It works out for you. I have it so hard. It’s been 7 months since I moved here all alone. My wife and I used to have sex at least once a week. Now? I haven’t felt a woman’s touch in so long. It’s been 7 months since I had sex.
Shekhar: A man has his needs. How long can I continue to jerk myself off? I’m bored of masturbating. But I am a married man. I love my wife. I don’t want to cheat on her with another woman. I feel so frustrated.
He placed his left hand on my right knee and said, “Do you understand what I’m saying?” He then took another sip of his drink. I placed my right hand on his hand and said, “Yes, I understand the frustration.”
He looked at me and said, “Wow. Your hands are so smooth.” He picked up my hand and started feeling it.
I don’t know what came over me, whether it was being drunk or that Shekhar was so close to me and holding my hand. I leaned forward to kiss him. But before I went through with it, I stopped myself and said Sorry.
Shekhar, slightly taken aback, took a couple of seconds.
Shekhar: It’s okay, we’re drunk. Coming so close and holding your hand may have sent the wrong signal.
Me: I should leave now. It’s getting late.
I got up to leave and started collecting my bags.
Shekhar: Wait. You’re drunk. Stay here till you sober up.
He once again insisted, and I caved in. But we stopped drinking.
Shekhar, however, was buzzed. He looked at me and asked, “Ankita, do you like me?”
To describe Shekhar, he was about 13 years older than me. But he was very handsome for his age. He was tall, well-built and fit. He could have been a model. Plus, he was also kind and nice to me. I enjoyed spending time with him.
Me: To be honest, I never thought about it before. I like spending time with you. It’s fun. But I think being a little drunk, and I lost my senses. Sorry once again.
Shekhar: So, you don’t like me?
Me: No. I didn’t say that. I must admit. You are my type. You’re so good-looking and kind and sweet. Any woman would be attracted to you.
Hearing this, he came and hugged me. He held me tightly. The front of my body pressed against his. I enjoyed his hug. I hugged him back as well. We stood hugging each other for a few more seconds.
Shekhar then dropped his hand and felt my ass. I let go of him and looked up. Our eyes met. Before I realized it, our lips met, and we started kissing. His hands were now feeling my body. He ran his hands all over my wig. He then started squeezing my silicone breast padding from over my clothes.
While I didn’t feel his hands through the wig or him squeezing my breasts, I imagined the feeling and felt good. I let loose and started to run my hands all over him.
Shekhar mumbled, “Technically, I’m not cheating on my wife with another woman. I know this is wrong, but I cannot stop. I was enjoying whatever was going on between us.” I whispered back, “You’re right. Don’t worry. Continue. Don’t stop.” Saying so, I started unbuttoning his jeans.
Shekhar continued to kiss me and feel and squeeze my breast padding. I unzipped his jeans and pulled out his dick from his underwear. I slowly started to go down on him, kissing his chest and stomach. When I reached his waist, I got on my knees and pulled down his jeans and underwear. Shekhar then pulled up his shirt, exposing his genitals.
His genitals were covered in pubic hair. But like an elephant’s trunk, his shriveled penis was hanging down. As I touched it with my fingers, it jumped up. Excited, I started to kiss and stroke his penis. Shekhar was not stopping me. He was enjoying my touch.
Encouraged by this, I ran my left hand along his ball sack and started to tickle his balls. I continued to stroke his penis after lubing it up with my saliva. A few minutes later, his erect penis was standing before my eyes. He had a 7-inch circumcised penis. The head of his penis was a reddish pink and was glowing.
I licked the penis head and even pushed the tip of my tongue into his pee hole. Shekhar jumped in excitement and started moaning my name sensually. I started to suck on his penis and began giving him a blowjob. This turned me on. I undid my pajamas and started to stroke my penis.
Shekhar held onto my face and started deep-throating his dick into my mouth. He was thrusting his hips. I started to gag on his penis. This got me even more excited, and I stroked my penis faster. I was blowing Shekhar’s penis with my mouth and jerking myself with my hands.
It became very erotic and hot. I was enjoying myself. Shekhar was also very excited as he was moaning loudly. I kept this up for a few minutes, and then, both of us climaxed and ejaculated. He squirted his load all over my face and body while my jizz fell on the floor.
After that steaming hot sex, we both fell back on the sofa and tried to catch our breaths. I had a beaming smile on my face. I looked at Shekhar. He, too, had a satisfied smile.
Next Part: Cross-dresser substitutes as Boss’s wife – Part 2