Hi readers. I am sharing my experience online hoping it will give hope to many young cross-dressing men. I too had given up hope of living a normal life as a cross-dresser until I found the right person who encouraged me to be the woman I wanted to be.
I had grown up crossdressing secretly. But of course my family found out about it. They thought it was just a bad habit and tried to make me stop doing it by scolding and beating me. They didn’t realize cross-dressing was not just a habit for me but was more than that. Ultimately, they couldn’t force me to quit cross-dressing. I continued to do it secretly even in my twenties.
While I was going through cross-dressing-related dysphoria, I didn’t give up on my education. So, after completing college, I got a junior-level job in a good civil engineering company. It was in this company I had this positive experience.
Five months after joining the job, I got a golden opportunity when my office conducted a fancy dress competition. I got to know that two guys were planning to cross-dress for the competition. I had a chat with them about it, and they confirmed their plan. I told them I liked the idea, and I also wanted to fancy dress as a woman. They encouraged me and gave me tips to dress up as a woman.
I was happy, but I was in a dilemma. There was only one person I knew who had a broad mind to understand me — my sister-in-law. She was from a modern family and a very understanding person. She’d found out about me one year after marrying my elder brother, but she had not judged me harshly. She’d actually told me many times not to feel ashamed and encouraged me to express myself without shame and fear. I respected her, so I told her about the fancy dress competition and expressed my fears about dressing up as a woman and facing my colleagues. She told me if participants don’t surprise others in a fancy-dress competition, it would be impossible for one person to win. She said since it is also an art form, nobody will make fun of it, and they’ll appreciate it. She even gave me examples of various actors like Sanjeev Kumar & Kamal Hasan, who had acted as a woman on screen for the sake of art.
I thanked her for the encouragement and requested her to help me on the day of the competition. She promised to help me and assured me that I will win. She kept her word by giving me her undergarments and helping me buy a new Salwar Kameez.
The competition was scheduled for Friday evening in the main office conference room. We were allowed to stop working early and get ready for the competition. I went home early and got ready at home. My sister-in-law told me to leave my room door open so she can come and help me. I agreed and left the door open. I went to the ensuite bathroom and removed my body hair before taking a bath. I applied body lotion all over, which made my skin silky. I wore my sister-in-law’s pink lace bra and panties, and then I wore the new sleeveless salwar kameez. I put on a waist-length black wig, bangles, jumkas, a pearl necklace, and a payal. My sister-in-law helped me apply light makeup and lipstick. Finally, she adjusted my dress until she thought I looked perfect to win the competition.
When I was ready, I thanked my sister-in-law and sneaked out of the house through the back door.
I reached the office building fifteen minutes before the event, but the security guy didn’t let me in. I showed him my access badge, but he still hesitated, so I switched from my female voice to a male voice, which finally convinced him. He giggled, apologized, and told me that I look very beautiful as he allowed me to enter.
As I entered, someone whistled. I turned back and saw the other security guys were grinning at me with lust on their faces. I couldn’t blame them because I had developed a good feminine figure after doing butt exercises regularly. The dress was also clinging to my bubble butt, which made me look more like a curvy woman. I walked away swaying my hips to impress them more.
I walked past some of my colleagues who seemed to admire me but didn’t show signs of recognizing me. As I entered the office, some colleagues recognized me and whispered to others. Everybody looked at me with disbelief and admiration. I didn’t feel awkward after seeing them in their fancy outfits. They were dressed as a princess, hunters, dancers, Batman, folk dancers, a warrior queen, film stars, etc. Dressed like a housewife, I felt underdressed even though my pink salwar kameez and dupatta looked perfect for a party.
I blended with the fancy crowd and chatted with some of my colleagues. They said I looked exactly like a woman and they couldn’t recognize me at first. I liked their compliments and enjoyed interacting with them as a woman. It was a great feeling to present myself as a woman to others comfortably without raising suspicion.
People were competing to get close to me and talk to me. I got unusual attention that I could not have gotten otherwise. I saw lust in the eyes of many of my male colleagues. Their eyes scanned my breasts even though it was fake. I enjoyed the way they looked at me. I liked the attention so much that I didn’t want the evening to end.
After one hour the winners were announced. I got the 1st prize and a big round of applause.
The party continued after the prizes were announced. I was getting more attention from the men, which made me happy. But I was surprised when I saw my boss, Arvind, gazing at me and playfully raising his eyebrows. I avoided looking at him fearing he might be testing me to find out if I am gay, just to fire me. I avoided looking at him and continued having a good time with my friends. But I felt his eyes on me and looked at him a few times, only to find him looking at me. It was like his eyes were fixed on me. I began to feel very anxious. Suddenly, I heard my boss’s voice say, “Please give us a moment alone.”
Boss was standing close to us. I turned to leave with my friends. “Not you. I want to talk with you,” he said.
I smiled, fearing I would have annoyed him by dressing up as a woman.
“It’s late. I’ll drop you home,” he said with a smile.
I wanted to stay and go home with my friends, but I just said, “Okay, sir.”
He began to walk. I followed him, confused and a bit scared. It is customary in our office to extend such courtesies to women, but I was not a woman. We exited the office and went to the parking lot. He told me to sit on the rear seat. As I got into the car, I noticed the driver was already sitting in the driver’s seat. I sat down and saw my boss getting into the car from the other rear passenger door. He sat on the rear seat, behind the driver.
As the car exited the office compound, my boss saw me and smiled. I gave him an uncomfortable smile. He patted the middle seat and said, “Come sit here.”
I was nervous and excited at the same time. I moved closer to him and sat on the middle seat. I felt uncomfortable because of our proximity, but it was good in a strange way. Because he was larger and taller than me, I felt like a woman beside him, dressed like a woman.
“You look beautiful today,” he said.
I looked to my right and saw his face. “Thank you, sir,” I said.
He held up his left palm and said, “Give me your hand.”
I kept my right hand on his hand. He lifted my hand and kissed the back of my hand. He saw me and smiled. Then he moved my hand down and pressed it on his crotch.
“It’s become hard for you,” he said.
I couldn’t help blushing. He pulled me closer and kissed my lips. I was afraid to kiss him back because he was my boss, but when his kiss became more passionate, I couldn’t help myself. Soon we were lost in a kiss that felt very, very romantic. He unzipped his pants, pulled his penis out, and rubbed my right hand on his penis. The length, thickness, and ruggedness aroused me more. I was having a good time being treated like a real woman, but we had to stop as we had reached my place. I really cursed my bad luck. He gave me a good bye kiss. I got out of the car and went home disappointed.
After that evening, my boss behaved like nothing had happened between us, and the reaction from male colleagues was very varied. Some guys looked at me with disgust, some guys treated me gently as if I am a woman, some guys looked at me with admiration, and some guys invited me to have sex with them. I refused to have sex with them, so they started teasing by asking me if I liked getting fucked by my boss. It hurt a bit because my boss didn’t do that to me. I wondered if I would ever get another chance to be intimate with my boss and kept dreaming. Every time I saw him, he behaved like he didn’t know me. He just seemed to be a normal guy who had little fun that evening in the car and forgot all about it.
Nothing happened between me and my boss for the next three months, and then he got transferred to a dam site, which was very far from the city. I was very disappointed that a man who liked me so much was going far away from me. But to my surprise, my superiors told me my boss had requested they depute me as his assistant at the site. I was very excited, but I was not sure if my boss had something more on his mind or not. But once my colleagues found out, some of them teased me. They asked me if I was going on a honeymoon with my boss.
I didn’t care about my teasing colleagues anymore. I was going far away from them, and I felt like I was going on a honeymoon with my boss. I went shopping for new female clothes. I bought Kurtis, salwar kameez, nighties, sarees, panties, and bras. I packed up my best clothes and ornaments ten days before we had to go.
Then it was finally the day for us to leave. We traveled in a bus together. I was very excited, but he didn’t give me special attention. It was a little disappointing. We reached the new location around noon and found the cottage where we had to live. My boss unlocked the door, and we entered inside. We put on the fan and relaxed on the sofa in the hall for a few minutes. That’s when my boss told me, “I am promoting you. You’ll be my wife from today. Dress up like a housewife and behave like one. Don’t wear men’s clothes. I don’t want anybody in the village to find out you are a man.”
“Okay, sir,” I said, feeling very excited.
“No, sir. Call me Arvind,” he said, strictly.
“Okay, Arvind,” I said, obediently.
“What is your female name?” he asked.
“Sakshi,” I said.
“Arvind and Sakshi. The names are a good match,” he said and paused to look at me. “Go get dressed before the workers come. I’ll introduce you to them as my wife.”
“Ok, Arvind,” I said with a big smile and rushed to the bedroom.
I removed my clothes and went to the bathroom. I shaved my body hair completely and took a refreshing bath. I applied body lotion all over my body. My skin felt soft and silky after shaving my body hair. I wore a new lace bra and panties, and then I wore a petticoat, blouse, and saree. I put on a waist-length black wig, bangles, jumkas, a necklace, and a payal. I applied little talcum powder on my face and proudly kept a red bindi on my forehead. I was very happy with how I looked.
Arvind walked into the bedroom. “Wow!” he said and went to his suitcase. He took something and came to me. He showed it to me.
“Wow! Arvind. Is it for me?” I asked, looking at the beautiful Mangalsutra.
“Of course,” he said. He put it around my neck. “Now you look like my wife.”
“Thank you so much!” I laughed with joy.
“I’ll have a bath and come,” he said and walked away.
I laughed happily and went to the kitchen. As I made chai for both of us, I felt very comfortable dressed in a saree. The perfect fit of the bra, the natural fake breasts, the soft material of the clothes, my exposed belly and navel, the free space between my legs under the petticoat, and my erect penis pressing against the soft fabric of the panties all made me feel like a beautiful trans woman. My voice and my body movement also automatically adjusted to my female personality. I felt completely like Arvind’s wife.
Later that day, the workers came to meet us. Arvind introduced himself and me as his wife. None of the workers seemed suspicious about me, and they treated me like a woman. They told us they came from nearby villages after sunrise and left before sunset. They also gave us more useful information about work and the location, before they left.
The location had thick forest surrounding the village, which was on the hills, but it was a nice place with scenic views. The cottage was located in a secluded area in the small village. It had two bedrooms, a hall, a kitchen, and two bathrooms. There were verandas and gardens in the front and back of the cottage. We loved our first home.
We had Chai together and talked openly for the first time. He confessed he wanted to have sex with me in the car after the fancy dress competition, but we had reached my house earlier than expected. I also admitted that I wanted to have sex with him that day. We decided not to hide our true feelings for each other anymore.
After having chai, I went to the kitchen and cooked food for dinner. When food was ready, we had dinner in the hall and watched TV. After having dinner, Arvind suggested that we should go for a walk. It was a bit dark, so I was little scared. He told me not to be afraid of anything and he will protect me. I was happy he was treating me like his wife from day one. We went out for a walk in the village. Surprisingly, there were a few people on the streets even at 9 pm. We walked for about half an hour and headed back towards the cottage. Arvind put his arms around my waist and walked to our cottage like a newly married couple.
It was our first night together. We were tired after traveling a long distance and walking around the village. We went to the bedroom and lay down on the bed. I thought he would fall asleep quickly, but he touched my boobs and said, “Remove your fake boobs.”
I laughed and removed my blouse, bra, and the cotton breasts. He rubbed his face on my chest and kissed my nipples.
“Sorry I don’t have breasts,” I said.
He raised his head, looked at me and said, “I like you the way you are.”
I was very happy he accepted me as I am.
He moved up and kissed my lips. I kissed him back. He lifted my saree and grabbed my aroused penis. He played with my penis and balls while we continued kissing. I moved one of my hands down and slid it inside his shorts. I grabbed his erect penis and massaged it. We played with each other’s genitals and continued kissing.
After a few minutes of passionate kissing, he moved back and asked, “Ready?”
“I’m ready. What do you want to do?” I asked.
“Anal,” he said.
“Lube is in my bag. I’ll get it,” I said, trying to get up.
“I’ll get it,” he said and got down from the bed.
I admired him as he took my bag and pulled out the anal lubrication tube. He was a well-built, tall, and handsome man. He was clean-shaven most of the time, but that day he had a 3 mm beard. He looked like a man most women would like. I felt very lucky that he wanted me. He saw me and winked. I chuckled and continued admiring him. He quickly removed his t-shirt, shorts, and underwear. His erect penis was finally exposed. It was long, thick and about the same size as my penis.
Fully naked, he stepped up on the bed and knelt between my legs. He told me to spread my legs and lift them up. I lifted my saree and petticoat and did as I was told. With my legs raised up, my bottom jutted out, offering him full access. He touched my inner thighs and caressed, squeezed, and kneaded them. “I love your smooth and soft skin,” he said with a smile.
“Thank you …” I said with a smile.
His hands rubbed my penis, my testicles, my butt crack, and my anus. He pressed a finger on my anus and rubbed it, smiling at me. I returned the smile, knowing he will soon fill me up with his penis. We shared a mutual love that is difficult to express in words. He inserted one finger and moved it in & out. I had cleaned the inside of my anal hole while having a bath, so I was happy to let him play with it.
Soon my rectum felt smooth inside. He inserted one more finger deep inside, twisted and turned, stretching my anus. It felt even better. He applied more lubrication and tried to push four fingers inside. That’s when it became very painful. I closed my eyes and controlled myself from screaming, but painful sounds escaped from my mouth and nose.
“Does it hurt?” he asked.
I opened my eyes and looked at him. I nodded, smiled, and said, “I am your wife. I can handle the pain for your pleasure.”
He chuckled and leaned forward on top of me. He pecked a kiss on my lips. “Let’s just try my penis this time. Next time, I might push my hand inside.” He grinned.
I chucked. “It’s not a vagina, Arvind. Only your penis can fit inside,” I said, thinking he was only joking.
“Let’s see,” he said and put his hands between us. He grabbed his penis and rubbed it on my butt crack.
He pushed my raised legs with his arms, which made my butt rise and jut out even more. I felt the tip of his penis pressing against my anus and closed my eyes, anticipating pain and pleasure to follow.
The round swollen head of his penis slipped into my anus. He pushed harder, and I groaned, “Ohh!…Ahh! Arvind!!”
His thick and long penis stabbed into my anus painfully, stretching my rectum wide and rubbing roughly against the walls of my anal canal. The lubrication inside was not enough, and I had forgotten to tell him to put lube on his penis. I closed my eyes shut and endured the pain.
It was finally fully inside me. My legs hurt from keeping them up for a long time, and my rectum hurt with his pole-like cock buried deep inside me. My anal hole relaxed and tightened automatically, trying to accommodate his cock inside. I could feel the lubrication had spread inside my rectum because of the penetration.
“Does it hurt?” he asked.
I opened my eyes and saw him. “Little. Don’t worry about me. I am your wife,” I said, reassuring him with a smile.
“Sure?” he asked, looking at my face doubtfully.
I nodded and said, “Sure.” I was touched by his care and love for me. I shut my eyes and challenged myself to endure the pain.
His penis pulled out and pushed back into me. The lube had spread deeper, but it still hurt. I lay with my eyes and mouth shut. Then it started. He held on to my legs and pounded his penis into my anus again and again. He banged his crotch on my butt every time his penis lunged into my hole. The penetration became smoother as his precum spurted into my rectum. My anal hole tingled as he thrust harder and faster. He made sounds of pleasure and continued penetrating me. The pain became less as the penetration became smoother. I moaned with him, loving every penetration. For a moment I thought he would go on forever, and I hoped he would, but I felt liquid inside my rectum and knew he had ejaculated. He penetrated a few more times and pushed his penis deep into me. Then he stopped and ejaculated more. He lay on top of me, pecking kisses on my face. I had not ejaculated, but I was happy I had satisfied my husband.
He rolled over and lay next to me. Then within a few seconds, he fell asleep. I was very happy with the progress we’d made as lovers. I went to the bathroom and washed. Then I wore a nightie and lay down next to Arvind.
The next morning, I woke up feeling fresh after having a satisfying sleep, but my body ached and my anus also hurt a bit. I had a hot water bath, which made the body ache less, but the pain in my ass remained. I went to the kitchen and made breakfast for us before Arvind woke up. He came to the kitchen, hugged me, and played with me. Then we had breakfast together. After breakfast we got ready to inspect the work site. I wore a salwar kameez, kept a red bindi and sindoor on my forehead, and made sure the mangalsutra was on top of the dress for everyone to see.
We left the cottage and walked to the work site, which was not too far. We met the workers and inspected the site. We did our jobs, but we worked like a husband and wife team. There was an underlying chemistry between us even though he didn’t attempt to touch me. I eagerly waited for the night to offer myself to him.
Later that evening, the workers left before the sunset. We walked back to the cottage holding hands. As soon as we reached the cottage, he took me in his arms and kissed me. He told me he wants to make love to me. I requested that he control himself a little longer because I had to take bath. He agreed and asked me to make hot chai and snacks. I changed my clothes, washed, and went to the kitchen. I made chai and snacks, and took the dishes to the hall.
We sat together and had foreplay while drinking chai and eating snacks. One thing led to another, and he made me suck his penis. I did it wholeheartedly, and he ejaculated in my mouth. He relaxed after that. I was happy I’d satisfied him again. I went to the bathroom and had a bath. Then I wore a saree and went to the kitchen. I cooked food for dinner.
Before we had dinner, we sat together and watched TV. He held me close to him, but he seemed tired, so I didn’t expect him to make love that night. We had dinner after an hour. After dinner, we went out for a short walk. We returned home, and he went quickly to the bedroom. I washed dishes in the kitchen, turned off the TV, locked the doors and windows before going to the bedroom.
He was lying on the bed and still awake. He saw me and asked, “What took you so long?
Surprised to see him awake, I said, “I washed dishes, locked the door, and turned off the lights.”
“I was waiting for you. Come and sit on my dick,” he said.
His direct demand made me laugh. I was surprised that he still wanted to have sex after he had ejaculated in my mouth, especially when he was tired. But I was happy. I took the anal lubrication tube and went to the bed. I lifted my saree and removed my panties. I asked him if I could straddle on top of him in the 69 position so he could lubricate me. He agreed to do so.
I stepped on top of the bed, lifted my saree, and straddled on top of him with my back towards him. His penis was below my face, and my bottom was above his face. Our penises were already erect, so I didn’t waste any time. I took his penis inside my mouth and sucked. He kissed, licked, and nibbled my bottom, butt crack, and anus before applying lubrication into my anus with his fingers. He dug into my anus with four fingers and twisted them around as he applied the lubrication cream inside. I continued to suck his penis until he told me to stop and sit on his penis.
I turned around and applied lubrication on his penis. Then I straddled him and grabbed his penis. I placed the tip of his penis between my butt cheeks and pressed its tip on my anus. I lowered myself and felt his penis sliding into my anal hole. This time the lubrication was perfect. The pain was minimal, and the slide down his thick and long penis was smooth. Soon I felt the tip of his penis hit some g-spot inside me. The effect was strong enough to make me tremble. He asked me why I was trembling. I told him his penis could have hit my prostate. He grabbed my penis and stroked it as if he were trying to make me relax. I forgot all the pain and laughed like a climaxing woman. Once that sensation died out, I felt as if his penis had gone right up to my stomach. I was sitting on his thighs with my butt cheeks spread apart and my hole stretched wide open by his thick cock that was stuffed through my rectum. I could feel the head of his penis shake gently on the other end of my rectum, inside my belly. It felt so satisfying that tears rolled down my cheeks. I bent over on top of him and kissed him.
After sharing a brief, passionate kiss with him, I pulled back and sat straight. I started moving up and down. He helped me by supporting the movement with his hands on both sides of my buttocks. His rod moved in and out of my stretched anus. I felt the rhythmic pattern and enjoyed the sensation it was creating inside me. I grabbed my erect penis and stroked it as I rode his penis like a jockey. I continued for quite some time till I lost control and sprayed cum on his belly. At the same time, I felt hot liquid splashing inside my rectum. Both of us had ejaculated at the same time. When he was done, I felt his penis soften and pop out of my anus.
When I opened my eyes, he had fallen asleep. I felt sorry for him. I got down from the bed and removed my clothes. I dipped a small towel in warm water and returned to the bedroom. I cleaned his belly and penis with the warm towel. Then I went to the bathroom and had a body bath. After drying myself, I went to the bed and fell asleep next to him.
After making love for the second time, our relationship became stronger. I became his faithful wife, and he became my loving husband. I cooked and cleaned. He took care of me and made love to me every day. He took me to the towns near the village on weekends and bought clothes and jewels for me. We went to restaurants and cinema theaters together. In the theaters, we sat in the last row and had foreplay, which usually resulted in me sucking his penis and him ejaculating in my mouth. We spent quality time together walking around the village and the thick forest. Sometimes when we went out for a walk in the night, he made me bend over on a rock or a tree and penetrated my anus with his fingers, tongue, and penis. It was wonderful to make love outdoors, in a natural setting, during the night, hearing the sounds of owls and frogs, while the mild wind soothingly caressed my skin.
Daily lovemaking made me feel like a complete woman. He has penetrated me in all positions: standing, sitting, bending, and lying positions known to us. Sometimes it was with long preparation and sometimes quick. Once, I even had dinner sitting on his lap with his penis fully inside my anal hole. One day he took me to a waterfall and penetrated me under it. Another time, he penetrated me during the day, in bushes.
I believe that my boss is the ultimate lover. I have one hole less than other women, but he tried most of the Kamasutra positions with me and I loved it.