Hi! I am Ashwini. I am a 29 year old trans woman. I have not undergone male-to-female surgery but with the help of medicines, I have breasts. I look very much like a woman and nobody has doubted me. I started as a crossdresser and transitioned to a woman. This is the story of how I had my first sexual experience as a trans woman.
It happened 10 years ago. I was only 19 at that time. I used to cross-dress secretly when no one was at home. I didn’t look bad in women’s clothes because I am fair and I have a girly body. My boobs weren’t developed then like they are now but I had a big bubble butt. I think I inherited it from my mom because she has a similar body. I was attracted to males and females but I kept it to myself. I didn’t have a boy friend or a girl friend and I had not had sex with anyone. But that changed after I visited my uncle.
My parents asked me to visit my uncle and help him because he was going through depression after his wife recently left him following an argument. Though we lived in Delhi and he lived in Pune, I agreed to go because I needed a change at that time. So, I went to Pune after two days.
I reached Pune on a Sunday. I went to the apartment where he lived. My uncle and I were happy to meet after almost one year. He looked little depressed and I felt sorry for him. He told me to take the guest bedroom and asked me to make myself comfortable. I took bath and changed my clothes before I went looking for my uncle. He was not there in the living room. I sat down on the sofa and turned the TV on.
I was watching cricket on TV when uncle came and sat on the sofa opposite to me. We talked and he shared his problems. He said auntie had left him with his children and he was afraid she won’t return. I asked him to take it easy and not loose hope. He told me he just needed someone at home till auntie returned or he’ll go crazy with loneliness. I told him I understand and I can stay for a few days till she returned. He said he’ll give me money to eat out as he can’t cook. I told him not to worry about me as I was good cook. He was surprised that I could cook. I told him I’d been learning cooking from my mom. He was impressed but he told me not to start cooking that evening and we could go to a restaurant for dinner. So later that evening, we went to good restaurant and had dinner.
The next morning, I woke up early and cooked food for breakfast. Uncle tasted the food and he was very impressed. I told him I’ll cook food for dinner and he said it was good idea.
After he left to the office, I was home alone. I opened my suitcase and took out the women’s clothes and a wig. I took my things and went to my uncle’s bedroom. I checked the closets and found aunties closet. Some of her clothes were still in there. I selected the clothes and ornaments I wanted to wear and kept them on the bed. Then I went to the bathroom. I cleanly shaved my face and body before taking bath.
After having bath, I went to uncle’s bedroom. I stood in front of the full length mirror and wore the padded bra. I stuffed soft clothes inside and wore a stretch blouse. Then I wore a petticoat and draped a saree. The blue saree hugged on to my hips and buttocks revealing the shape of my ass cheeks. I loved it. I put on the waist length, straight hair wig, necklace and bangles. Finally, I touched up light make up on my face and kept a red bindi on my forehead. I was happy with how I looked in the mirror. I left the room feeling like the lady of the house.
I cooked, cleaned and watched TV like a house wife. When I felt horny, I found a long and thick cucumber in the fridge. I lubricated my anal passage and the cucumber, then I thrust the cucumber inside and pumped it in, while jerking my cock in my fist. It wasn’t as good as having sex with someone but it satisfactory.
Before uncle returned, I undressed and dressed up like a guy again. Uncle and I were happy to see each other in the evening. We had Tea together and chatted, watching TV. At dinner time, we ate the food I had cooked. Uncle liked the food very much. He asked me to pack up the left overs in his lunch box for the next day.
After uncle went to his room and closed the door, I watched TV. I was still little bored. I got an exciting idea. I put the TV off and went to my bedroom. I cloed the door, removed my clothes and dressed up like a woman. I felt good. I lay on the bed and played a game on my mobile until I felt sleepy and fell asleep.
The next morning, I woke up early. I wore my male clothes and went out of the room. I cooked food for breakfast. I ate with uncle and he said he liked the food. I gave him the lunch box before he left.
I was alone again. I took bath, dressed up like a woman and spent the day like I’d done the previous day. Before uncle returned I changed my clothes. After he came home, we had tea and chatted. Then, we had dinner at the same time as the previous evening. After dinner, he told me goodnight and went to his room. I went to my room and got dressed like a female. I played games on my phone and fell asleep.
The same routine happened next day. On the fourth day uncle seemed less depressed when he returned from the office. He said we should go out for a change and eat in a restaurant. I thought it was a great idea. We went to a busy market area. We walked and looked around. He informed me about the the streets and shops which were well known. Unexpectedly, he met a old friend and they started chatting. I saw a shop where they were selling ornaments. I told my uncle I will be back within a minute, and he nodded. I quickly went to the shop, bought a Mangalsutra and went back to him, just in time when they were ending their conversation.
We went to a restaurant and ordered food. He told me about his friend we had just met. Then after the food was served we ate and talked. Suddenly, he changed the topic and asked me if I had any plans of getting married in the future. I told him I had to get a good job or start a business before I even think of getting married. He said it’s good that I am interested in girls. I was a surprised. I asked him what he meant. He said he’d talked with his sister, my mom, and she had expressed concern that I might be gay. I was angry with mom. She’d had expressed the same concern to me and I had assured I was attracted to women. So I didn’t understand why she had to discuss about that with her brother.
Uncle told me he can help me find a good girl if I am interested. I thanked him and told him I’ll let him know when I am ready to start dating or get married. He said he understood and he hoped I would do the right things in life. It was frustrating, so I changed the topic.
After having dinner, we went home. I was little upset with him for talking about it but I pretended like I didn’t care and chatted normally with him. After we reached home, we watched TV for a short time, then he went to his room. I went to my room, wore a saree and fell asleep.
The next day was a Friday. After uncle went to the office, I followed the same routine as the previous day. I took bath and wore a saree. I put on a wig and bangles, and I kept a Bindi and Sindoor on my forehead. Then, I put on the Mangalsutra, I had bought. I looked exactly like a house wife. I was very happy. I enjoyed the day alone. Before uncle returned, I changed my clothes. Uncle and I spent the day at home. He had dinner at his usual time and went to his room.
The next day was Saturday. I wasn’t sure if uncle worked partial or full day. I asked him about it when we had breakfast. He said he usually worked full day on Saturdays but some days he was allowed to leave early. I told him we were running short of vegetables and I had to go to the market to buy them. He gave me money and asked me buy all the groceries I needed.
I wanted to finish shopping first. So after uncle left, I went to the market and came home only at 10:30. Then I cleanly shaved my face and body before taking bath.
After a refreshing bath, I wore a saree I found in aunties closet. It was a pink saree with light and medium pink shades. It had floral embroidery at the bottom and on the pallu. The colour blended well with my skin colour and the fabric hugged well to my hips and buttocks. I put on the wig, Mangalsutra and bangles, and I kept the Bindi and Sindoor on my forehead. I was happy with how I looked. I went to the kitchen and started cooking.
I finished cooking at about 12pm. Then I went to uncle’s room to check my appearance in the full length mirror. I adjusted the saree and the wig-hair. I turned around, checking my sides and back. I was happy, I looked perfect. I stood facing the mirror and began adjusting the Mangalsutra when I heard door open. I thought it must be the neighbors but I got a shock when heard my uncles voice. “Ashwin!” he called out. I panicked and looked at the door. He was not there. I thought of quickly sneaking into the attached bathroom, but I heard him ask, “Who are you?!”
I looked at the door. He was standing there, staring at me with shock. His expression turned from shock to confusion. “Ashwin?” he asked.
“I am sorry. Please don’t tell mom and dad,” I requested and added, “I’ll go back today.”
He smirked, shook his head and came close to me. He stood two feet away from me. He looked me up and down, then locked eyes with me.
“I’m sorry. I’ll change and leave,” I said, with fear. He was still a few inches taller and larger than me. I was afraid he could slap me or beat me up for touching his wife’s clothes.
“Are you wearing a Mangalsutra?” he asked, looking down at my chest.
“I bought it,” I said, fearing he could think I stole his wife’s jewels.
“Stand right there!” He said, and went to the closet.
He opened boxes and checked. I stood in the same place, frozen with fear. I was scared he would accuse me of stealing.
He came to me and said, “Remove the Mangalsutra.”
I wanted to tell him, ‘It’s mine,’ but I was afraid and guilty. Tears filled my eyes. I removed it and gave it to him.
He took it from me and said, “Turn around.”
I turned around holding back the tears. I felt his arms move around my neck and slide back. The wig-hair moved from my back and I felt his fingers on my neck. I thought he put a chain and looked down at my chest. I saw a double wati Mangal Sutra. Before I could realize what was happening, I felt his arms slide around my waist and his crotch pressing on my butt. I felt kisses on the right side of my neck and checks. “You are perfect,” he whispered into my ear.
My heart was jumping with joy. He turned me around and our eyes locked. He smiled and said, “Stay with me.”
I smiled, nodded and wiped away the tears from my eyes.
“You are my wife,” he said.
“But uncle, I don’t have boobs and vagina,” I said, fearing he was getting carried away just by seeing me dressed like a woman.
He pulled me closer to him, till my fake boobs were pressing against his chest. “That’s okay,” he said, and grabbed my ass cheeks. He lifted them till I was standing on my toes. “I know what do with you,” he said, with a smile.
I smiled feeling shy. I was so happy he knew what to do.
His hands touched the sides of my face and he pecked a kiss on my forehead, my nose and then my lips. The kiss was gentle at first, then it became a passionate kiss. His tongue licked my lips, tongue and mouth. His hands moved down and lifted my clothes above my butt. He grabbed my bare ass and squeezed hard. Then he stretched them apart and ran his fingers in the crack of my ass. One finger poked against my anus and an inch of his finger slid inside.
I broke the kiss and looked into his eyes. “Uncle, it will hurt without lubrication,” I said.
“Don’t worry. I’ll oil it,” he said, grinning. He removed his arms from me. “Kneel down on the bed.”
I lifted my saree and petticoat above my butt and climbed the bed. I knelt on my knees and hands. Uncle removed his clothes. He took coconut oil from the dressing table and climbed the bed. He knelt behind me, between my legs. He caressed my butt and thighs. “Your skin is soft and smooth like a baby’s skin,” he said, running his finger in my ass crack.
I was pleased Uncle liked my skin. Shaving and moisturizing everyday had really made the difference.
I felt one finger dig into my anus and closed my eyes. It was oily and slippery. The finger dug inside and twisted around. Then it slid out, and in few seconds, I felt two greasy fingers enter my hole. The fingers twisted and turned applying more oil.
After thoroughly massaging and oiling my hole, uncle pulled out his fingers. Then I felt the thick and smooth surface of his cockhead on my anus. It was nice to feel a cockhead on my anus for the first time. I placed one side of my head on the mattress, stretched my arms behind and grabbed my ass cheeks. I spread my ass cheeks apart, stretching my anus. The cockhead popped into my anus.
“Ready?” he said, caressing my butt.
“Yes, Uncle,” I said, longing to feel it fully inside.
Then I felt it move inside, inch my inch till his crotch pressed hard against my butt. It hurt, but not too much because Uncle had done a good job lubricating.
“Perfect fit!” Uncle said, caressing my butt.
He was right. His cock fit perfectly inside my rectal-anal canal. A cucumber had never felt so good. This was different. His cockhead was deep inside my rectum and his entire shaft was throbbing inside me, stimulating my anal nerve endings.
Uncle moaned with his seven inch cock plugged into my anal-hole. His fingers held my hips with a firm grip and his crotch pressed against my ass cheeks. Our balls dangled together and I felt physically united with him. I stretched my right arm between my legs and grabbed my cock. I stroked it and comforted it.
I felt Uncle’s cock move out and stop halfway, then it slowly moved back inside, filling me up again. It moved out again and back inside again. It happened again and again and the speed gradually increased. I pumped my cock with my hand faster matching the speed of Uncle’s cock that was pumping into my asshole. We worked in harmony, pumping our cocks faster and faster. The pleasurable pain from my asshole made my head feel numb and my balls ached to flush out cum. My body trembled as Uncle’s crotch repeatedly slapped my ass and his cock repeatedly hammered into my asshole. “Ahhh! Uncle! Uncle!” I cried out, loving what he was doing to me.
Suddenly, I shuddered as my cock shot cum and my asshole contracted and squeezed Uncle’s cock. I felt wetness inside my asshole and laughed realizing Uncle had also cum at the same time. He moaned loudly with relief, ejaculating lot of cum he had saved up since his wife had left him.
Uncle leaned over on my back and kissed the back of my neck, shoulders and arms. His cock slowly shrunk and popped out my asshole. We lay on the bed like lovers kissing and cuddling for half an hour. When he was ready to have I lunch I got down from the bed and went to the bathroom. I had a quick body bath and wore a saree. Then I went to the kitchen, made the food hot and took the dishes to the living room. Uncle was sitting on the sofa. He had washed and put on clothes. I kept the dishes on the table and sat next to him. He put his left arm around my waist and pulled me closer to him. He pecked a kiss on my lips and said, “I want to make love to you again.”
“Okay, Uncle. Eat first and get more energy,” I said, laughing.
We fed each other and ate food. After we finished eating, we watched TV together and relaxed for a while before Uncle began fondling me. When he was ready again, he applied lube in my asshole and made me sit on his lap, with his cock lodged in my asshole. He fucked me and ejaculated again. It was the second time that day and it was only 2pm. He fucked me two more times before dinner time. After dinner he fucked me twice again before went to sleep together.
After that first day we had sex, Uncle fully recovered from depression. He didn’t miss aunty anymore. He was happy to come home and make love to me. We had a good time for one and half months, then Auntie told him she was coming home. I requested Uncle to divorce Auntie and marry me but he was afraid of what people would say. I was heart broken. He fucked me as much as he could and let me go.
I returned to Delhi and became a transformed woman. I have boobs and I look so much like a woman that no one can guess that I was born a man. Uncle and Auntie divorced after three year. Uncle asked me to marry him but I refused. I didn’t want to be a wife to some one who ditched me. I am successful independent woman. I own three massage parlors. I have many employees but lot of my clients like to get Happy Ending massage only from me. If they are good, I let them fuck me and they pay me well. I don’t need to be a temporary wife anyone. Life is good and I have no shortage of love.