My boss and me

Hi! I am a 30-year-old transwoman. I am 5’7″ tall, fair, and physically fit. This story I am writing happened six years ago when I started my Hormone Replacement Therapy. Five months after I had started the therapy, my skin had become soft, and I had developed small breasts. I tried my best to look more feminine by performing glute-building exercises such as squats, deadlifts, and lunges. As a result, I had a slim waist, wide hips, and big buttocks. I also waxed every part of my body to look and feel more feminine. As my structure became more feminine, I looked like I had man boobs, feminine hips, and big booty. I began wearing tight-fitting pants to make my buttocks look more attractive. I got the attention I needed from gay and straight men at work. But everything was not going well at work. Some co-workers hated me because I was bisexual. They even complained to my boss. But my boss was a good man. He advised them to avoid getting involved with personal matters of co-workers because gender identity and sexual orientation were personal to everyone.

My boss’ name is Karan. He was in his early 40s at that time. He is 6 feet tall, with wheatish skin complexion and a muscular body. He treated everyone with respect, but he treated women with more respect. And he gave me the same respect he gave the women in the office because I was feminine. He was a married man who had one child. Everything seemed to be going well for him until his wife died in an accident. After that, he became withdrawn. I felt sorry for him, so I wanted to console him but the women in the office gave him more attention than I could. Despite the attention he got from the women, he looked withdrawn. I couldn’t stop feeling sorry for him. I wanted to help him, but I didn’t know how to help him. Fortunately, one day I met him in the elevator.

It was a Friday. I went to the office one hour early to finish the pending work. When the elevator door opened, I saw my boss. I wished him Good Morning and he wished me back. As the elevator moved up, I felt shy and a little self-conscious. Unexpectedly, my boss said, “You look very beautiful today.”

I blushed, laughed, and asked, “Only today, sir?”

He smiled, and said, “You look beautiful every day.”

“Thanks sir,” I said.

“Do you like dressing like a man?” he asked.

I was glad he had brought up the topic. So I said, “Actually sir, I prefer to wear women’s clothes.”

“Hmm…interesting. You’ll look very beautiful in a Saree,” he said.

“Do you want me to wear Saree to the office sir?” I asked and laughed.

He laughed, and said, “I need to think about it. I’ll let you know.”

The lift stopped. I said, “Thank you, sir.” And we stepped out of the lift.

As we walked into the office, he said, “You are early today.”

“I have pending audit related work sir,” I said.

“Oh, I see. I am here for the same reason. I won’t be able to finish today. I may complete it this weekend,” he said.

“Do you need my help, sir?” I asked.

“Thanks for asking, I’ll let you know,” he said.

After we reached my cubicle, he said, “See you later.”

I said, “See you sir.”

After he walked away, I tried to calm myself and thought, ‘Wow! What a man!’

He was really something. At that moment, I wished I had been a very beautiful woman to seduce him and marry him. I just shrugged with disappointment and ignored the thought. I sat down and focused on work.

Later that afternoon, after lunch time, I received a call from my boss. He requested me to come to his office.

When I went to his office, he told me to sit down. After I sat down, he asked, “Roshan, do you have a female name for yourself?”

I laughed and said, “Sir, my female name is Roshni.”

“Roshan and Roshni,” he said and laughed. Then he asked, “Do you want me to call you Roshni?”

“I prefer to be called Roshan in the office, sir. I don’t want people to make fun of me,” I said.

“Don’t worry. I’ll call you Roshni only when nobody is around,” he said and smiled.

“Thank you,” I said.

He quietly looked at my face for a moment. Then he asked, “Roshni, can you come to my house this weekend and help me finish the audit work?”

“It will be my pleasure sir,” I said without hesitation.

“Great. Please come home on Saturday at about 10:30am. Bring your laptop,” he said.

“Ok sir. No problem sir,” I said.

“Also, I thought about the chat we had in the elevator,” he said and looked at me for a moment. Then he said, “I want to allow you to dress in women’s attire to the office, but I am not sure if you will look decent. So, I want to see you dressed as a woman first, before I make my decision.”

“No problem, sir. I’ll come to your house dressed as a woman.,” I said, hoping he doesn’t reject the idea.

“Good Idea. See you later,” he said and smiled.

“See you, sir,” I said and left his office.

The next morning, I woke up thinking about my boss. I was happy I was going to his house. I thought about his handsome face, muscular body, and his smile. Though he had invited me to his house only to help him complete pending jobs, I wanted to get more friendly with him. I planned to wear a good Saree and look like a decent woman. Even though I had gone out in the public wearing women’s clothes many times, I was excited to do it again.

I had breakfast at about 8:30. Then I went to the bathroom and had bath. After bath, I started getting dressed. I wore a pantie and 34A bra which fit my breasts perfectly at that time. I wore a shapewear petticoat and a green blouse which matched the medium green colour saree I had selected. The Saree had thick Zari border and thin red colour border. It also had Zari leaf designs embroidered on the bottom part of the Saree.

I draped the Saree around me and looked at my reflection in the mirror. I looked beautiful. The Saree hugged well around my legs, hips, and buttocks. Hormone therapy and years of glute exercises had paid off. I looked more feminine and curvier.

I put on light makeup. I kept a Bindi on my forehead and applied lip gloss for my lips. I wore a simple gold chain and bangles. Finally, I wore a wig which had wavy, waist length black hair.

By the time I was ready, I had a hard-on. I had got turned on by looking at myself. I just laughed it off. I took my ladies handbag and my laptop bag. I opened the main door feeling nervous even though I never spoke with the neighbours. I locked the door and walked to the lift. The door opened and I saw two women. They didn’t look suspiciously at me, so I felt more confident. I got out of the lift and went to the parking area. Men who walked by looked at me with lust. That made me even more confident. I got into my car and drove towards my boss’ house.

It was a beautiful day. Though the traffic was horrible as usual, I enjoyed the drive, dressed in a beautiful Saree and feeling like a beautiful woman.

After a twenty-minute drive, I reached my boss’ house. I parked the car on the side of the street and went to his house. I rang the doorbell. He opened the door and looked at me as if he didn’t recognize me.

He looked like he had not shaved his facial hair for more than 3 months.

I smiled at him.

“Roshan?” he asked and looked at me from top to bottom.

“Roshni, sir,” I said and smiled shyly at him.

“Wow! You look very beautiful. I couldn’t recognize you for a moment,” he said.

“Thank you, sir,” I said.

“Come in, come in.” he said.

I entered the house for the first time. The house looked very good inside. The living room was very spacious. The décor looked elegant, and the furniture looked expensive. There were scented candles and natural light all around because of large windows.

“Have a seat,” he said, showing me the couch.

I went to the couch. He followed me and said, “I didn’t expect you to look so beautiful.”

I just laughed but when I felt a touch on my buttocks, my heart skipped a beat. I stopped laughing and stopped walking.

“Beautiful,” he said, moving his hand on my buttocks and feeling it through my clothes.

I just stood there nervously with my handbag hanging from my left shoulder and my laptop bag hanging from my right shoulder. He touched my arm and turned me. I turned and looked at him with a shy smile. His hands grabbed the sides of my bare waist, and he kissed my lips. The kiss turned into a French kiss within a few seconds. His kiss was so enthusiastic, my head began to spin. He grabbed my buttocks and squeezed as he kissed me. I felt his hard penis pressing on my hard penis and wondered what he wanted to do to me. As if he could read my thoughts, he broke the kiss and said, “You should not be working this weekend. A beautiful woman like you deserves better treatment.”

I looked into his eyes with excitement, wondering what he meant. He took my bags from my shoulders and kept them on the couch. Then he squatted little bit, he placed one arm around my lower back, and the other hand behind my knees. Before I could understand what, he was trying to do, he was trying to lift me. Loosing balance slightly, I quickly put my arms around his shoulders. He picked me up quickly. I held on to him hoping he won’t drop me down and looked at him feeling scared.

He said, “Don’t worry. You are safe.”

“You scared me, sir,” I said, with my heart still racing fast.

He laughed and carried me to the bedroom. He lay me on the bed. He got on top of me and kissed me with so much passion, I began to wonder how he had controlled his desire to have sex with me for so long. He sucked my lips and tongue. He licked the insides of my mouth. He kissed my nose, my cheeks, my eye lids, forehead, ears and neck. Then he went down, lifted my Saree and petticoat, pulled my panties down and began kissing my thighs, testicles and my hard penis. I couldn’t believe what he was doing. Before I could convince myself that it was really happening, he started sucking my penis. At that moment, I didn’t care if I was dreaming or not. I just closed my eyes and enjoyed it.

He sucked my penis and stroked it with his fingers. He was trying to make me ejaculate and I was almost ready to ejaculate. When my body began to spasm he sucked my penis again. Unable to control myself, I ejaculated in his mouth. But before I could fully ejaculate, he pulled my penis out of his mouth. He made me turn and lie face-down. He parted my buttocks and opened my anus with his fingers. Then I felt liquid flow inside my anus and realized he was spitting my semen inside my anus. At that moment, I was impressed by my boss’ brilliance.

I lay still waiting for my boss to make the next move. And then, I felt the tip of his penis pressing on my anus. Then his cockhead slid inside me. I was relieved and happy because it didn’t hurt much. But I expected pain to follow. I lay still hoping he would be gentle with me but suddenly I felt sharp pain as my anus stretched to accommodate his hard penis. He had thrust his penis fully inside my anus. I groaned with pain and tolerated it. My anus still felt dry even after he had lubricated it with my semen. I could feel his hard penis throbbing inside me, at least nine inches deep. It hurt but I was determined to make sure my boss was happy.

He lay down on my back with his penis inside my anus and asked, “Happy?”

I laughed and said, “Very happy, sir.”

“Good. But stop calling me ‘sir’. We are lovers now. Just call me Karan,” he said.

“Ok Karan,” I said and laughed.

“Good. Let’s finish it,” he said.

I closed my eyes expecting more pain. I felt his penis withdraw. Then suddenly it stretched open my anus again and filled the void. It was back where I wanted it but it hurt. I closed my eyes and tolerated it knowing very well that the pain would turn to pleasure. His penis moved in and out of my anus few more times before the lubrication spread fully inside my anus. The nerve endings in my anus were beginning to respond to the wonderful anal penetrating massage. Soon the pain turned to pleasure just as I had expected, and I began to enjoy it. Every time he pushed his penis inside my anus, I felt like it belonged there, but I also felt like pooping it out. And when he pulled it out, I felt the relief of pooping a very large turd. Though my prostate was not stimulated I felt very good, and I didn’t want him to stop. His pelvis slammed on my buttocks every time he penetrated my anus. He desperately fucked me like a wild animal. I was happy I was able to give him the pleasure he needed.

“Oh Roshni,” he moaned loudly and thrust his cock fully inside my anus. Then I felt wetness inside me. He filled my anus with his semen and lay on my back, breathing heavily.

I closed my eyes and relaxed. After few minutes, I felt a kiss on my cheeks and opened my eyes.

“You are so beautiful,” he said.

“Thank you, sir,” I said and realized my mistake immediately.

“Karan,” he said, correcting me.

I laughed and said, “Thank you, Karan.”

“Stay with me tonight,” he said and kissed my cheeks again.

“Ok,” I said, loving the affection he was showing me.

I spent the weekend with my boss. He had sex with me in every position he liked. He had penetrated my anus so many times in the weekend, it felt sore till I met him after one week. Then he again penetrated me too many times and made it sore. The soreness in my anus never went away but it constantly reminded me of his love me.

Six years later, I look every bit like a woman. I have D-cup breasts, bigger hips and buttocks but I am still a preop trans woman. I am Karan’s wife and a stepmom to his daughter. I don’t work anymore but Karan is still my boss at home. He loves making love to me and my anus always feels sore, reminding me of his love for me.


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