A night to remember

Roommate: Part 2


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Special thanks: We would like to thank Nikkie Dominoes, an amazingly beautiful crossdresser for her pictures in blue saree, used in this story. She reserves her copyright for the pictures. She has a youtube channel with a lovely collection of videos. It’s worth visiting!

Click here to read all the parts of this story/ हिंदी में यहाँ पढ़े 

I still have many hours left in my flight before I reach California. I could still vividly remember my hot night with Chetna. Oh, What a wonderful night it was! The first time I ever made love to a woman, and she was not even a woman. Chetna was really a man wrapped in a beautiful saree; she was a man named Chetan who also my best friend. “But does it matter if Chetna were not really a woman?” It should not matter if she behaved like a true woman. Love has no boundaries, and it should not be impacted by the gender of a person. Right?  But we were not in love, at least not until that night. We were just two horny drunk people who jumped into the bed at the first chance. And that’s why, this question was going to bother me throughout the next day.

When I woke up the next morning after that passionate night, the warm and soft body of Chetan (or Chetna) was still snuggling in my arms. The touch of his silky smooth saree felt really good on my naked chest. I was still sleepy as we had barely slept for two hours after making love all night. But after the night, comes the morning. And your mind begins to think about all the things you did in the darkness of the night.

That morning, the effect of alcohol had faded out, and my hormones were not raging anymore. Chetan was still sleeping. “He” or should I say “she”? looked really attractive with her eyes closed. I saw her lying next to me in a bed. She was sleeping unaware how attractive she looked in her tight blouse. I could see her sexy back in her silky blouse with a deep cut; inviting me to kiss her back. What can I say? Her body wrapped in that slippery saree looked so attractive. And I could not avoid touching her lightly all over her body. She moved a little as if she enjoyed my touch, but very likely she was still sleepy. I kept looking intently at this sexy woman who made me a man last night.

But there was something else that occupied my mind that morning. And it was really making me restless. Last night, I had made love to a man, though he looked and behaved like a sexy woman, he was still a man. And it made me wonder, “Am I gay?”

If you were in my shoes, and if you were a guy like me who was attracted towards woman, you would have felt the same way. Thinking about what I did last night, I quickly wanted to run away from there.

In a moment of impulse, I got up from the bed soon. Chetna got up too, but her eyes were still sleepy after the passionate night. I can’t even describe how hot she looked in the morning! There is something about the woman’s messy look in the morning. If a woman is comfortable enough to wake up in a messy look with you, it tells you that this woman is all yours, no one else can touch her the way you do. It means that she has dedicated herself to you. And as a man, it was my responsibility to make this woman feel special. Chetna looked into my eyes as if she was expecting a good morning hug and a kiss from me. Her eyes were begging for my touch, not a sexual one, but a touch out of love.

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Chetna was still sleeping when I woke up in the morning. Her body looked really attractive in the saree she was wearing. Don’t you agree?

But I ignored her begging eyes, and I said, “I should take a bath, and get ready for the office.” I didn’t want to tell Chetna how confused I was feeling that morning.

“What’s the rush, Nishant? Please, sit next to me. Come spend a little time with me. Please?”, Chetna turned towards me in the bed. Her saree slipped a little, and I could see one side of her blouse covered lovely breast. She tried to cover it, but her saree was too silky to hold it. I could not avoid staring at her blouse. After all, it looked really sexy. She noticed what I was looking at. She blushed as she felt a little shy because of my staring at her breasts.

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When I got up from the bed, Chetna woke up too. She looked towards me as if her eyes were begging for a good morning kiss.

But I had made up my mind to leave her alone as I pulled up my pants. She must have realized that I was not going to stay with her any longer. So, she got up in her bed. She gently covered her feet with the saree. She fixed her saree pleats which had become a little messy at night. She pulled up her saree aanchal to cover her lovely bosoms. She looked like a morning angel with her dreamy eyes and a lovely smile. “At least, tell me you liked the last night.”, she spoke again in a soft sexy voice that I found too difficult to resist. She needed some words of love and appreciation to make her feel like a special woman, and not a sex object.

I kept looking at her beautiful body. “Yes, Chetna. It was a beautiful night.”, I said, “… but we should hurry. We should not be late for the office.”

Chetna was still looking at me, she was dying for a morning kiss from me. A woman who made love to you last night deserves at least a good morning hug, if not a kiss. But without saying anything to Chetna, I just left her there in her room. Her luscious lips remained longing for one kiss she had implicitly asked me.

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Chetna got up and covered her feet with her saree. She was irresistible as a woman.

I came to my room. I took my bath and got ready for the office. All this while, my mind kept asking me confusing questions. I could not deny that I really enjoyed my night with Chetna. I could vividly remember her feminine body move and wrap around me. I could still feel the sensation when her soft smooth body touched mine. But there was this one question that kept haunting me. “Was I gay?” I never considered myself to be one. I never had thoughts like that for any man. I always wanted women in my life. So, how do I explain making love to a boy? But he was a woman last night. No matter what, no matter how much I denied it, the fact remained that the woman I made love to, was a man! It was not a night that I could easily forget.

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When I left the home, Chetna was in the kitchen doing something.

Somehow, I left the house to go to my office without Chetan, who was doing something in the kitchen when I last saw him/her. I didn’t even stop to say good bye to her. I just walked out of the home. I had a lot of work to do anyway. The entire day, I didn’t even bother to see Chetan who worked with me in the same office. I didn’t want to. I could not really muster the courage to face him. But Chetan came up to me that evening. There was an unsaid sexual tension between us.

“Hey Nishant, it’s time to go home buddy. You have worked hard enough for today.”, Chetan said to me. He was right, it was already 6 pm.

“Sorry yaar. I still have some work to do. I will stay here for another half an hour. Why don’t you go back home? I will see you there.”, I said to Chetan. I could not look at him. I could still see Chetna instead of him. I could still see her gyrating body in her sexy saree when she made love to me. It was a strange situation for me. My best friend had become a lovely woman who I found really attractive.

“OK. No problem. I will see you at home.”, Chetan said. He gave me a smile. It seemed like he winked at me. “Did he just wink me? Is Chetan suggesting something more? Does he want to repeat what happened last night? How can he be so cool with what happened last night? Is he gay? Am I gay?”, I wondered in my mind. I didn’t want him to think that I want to spend another night with him or Chetna. But he had left. May be I had only imagined him winking at me. Probably, he didn’t mean that. Some people might judge me for my behavior. But honestly, all this was happening so fast. Within 24 hours, I not only came to know that my best friend is a cross-dresser, I ended up making sweet physical love to him. I wanted to deny to my mind that anything like that had happened. Oh, what a confusing time it was.

I stayed in my office for another half an hour. Then, I took out a cigarette, lit it, and began to walk towards “our” home. It must have taken me 45 minutes to walk, but the time flew by thinking about the events that happened yesterday. I must have smoked four or five cigarettes on my way. I didn’t want to talk to Chetan today, but how could I avoid seeing him? He was my roommate.


I arrived home, and opened the front door. I walked up to the kitchen. I thought I will cook something tonight. That would be a good way to avoid talking to Chetan, I thought. I took out an onion and a few potatoes to peel. I knew that I could not avoid Chetan for long, but this seemed like a start, at least for the next hour.

“Nishant, is that you?” I heard a voice from a different room. “Nishant”, the voice sounded distant. I turned around hoping to see Chetan. But Chetan was not there. I peeked into Chetan’s room, the door to which was open.

And I was pleasantly surprised to see Chetan who was wearing a different saree from yesterday; this was a very homely saree. It gave him a look of a lovely housewife, and a hot one too! I could see him checking his looks in the mirror. He was trying to cover his boobs with his saree aanchal, but that saree was really smooth and silky, it didn’t stick around. No matter how hard he tried, his saree would slip and expose his one boob. “One Open One Closed” or O3C as I used to say to describe boobs of ladies like these.

Have you ever seen a woman getting ready in front of a mirror? It’s such a pleasant sight. Women get so involved in that lovely activity where they try to look their best. And Chetan was occupied doing the same thing. He tried wrapping the saree pallu around his waist, then tried keeping it open; he couldn’t make up his mind. He kept trying different looks. He opened his hair. He tried keeping his long hair on one side on the front. Not satisfied with the look, he pulled the gorgeous locks of hair to the other side. He could not decide how he wanted to keep his hair or hold his saree. I kept looking at this beautiful woman trying to get the right look. I enjoyed her dilemma with her saree and her hair. I really liked what this woman was doing; her each movement was stimulating me. I looked at this woman’s big ass, which looked too hot in that satin-y saree. I felt like going and hugging this woman tightly against my chest, and grab her soft hips with my hands. She looked tempting. She looked sizzling. She looked irresistible. Even in a homely casual saree, she looked too sexy. There was no denial that I found this woman attractive.

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Chetna was standing in front of a mirror. Like a true woman, she tried several looks. I loved looking at her getting ready. [Image Credit: Nikkie Dominoes]
I had been watching this woman, Chetna, for a while now. Suddenly, she noticed that I was staring at her.  She must have realized that I found her attractive. She blushed looking at me. She quickly covered herself in her saree; she let her saree pallu open up as she pulled it to the front of her waist. “I am sorry. This saree is a little difficult for me to manage. I wish you hadn’t seen me like this when I am not perfectly dressed.” But she was perfect in my eyes. After a day of hard work, I found it really relaxing to come home and see a beautiful woman getting dressed for me. My hormones were raging again. I wanted to hug Chetna desperately. But I didn’t want to make the same mistake again. I controlled my urges. And I didn’t say anything to her yet.

Chetna came closer to me. My heart beat began to rise. I was finding it harder and harder to avoid holding her in my arms. I wanted to squeeze her breasts against my chest. But I couldn’t gather the courage to do anything. She came further close to me. So close that she could probably feel my breath. She took one of my hands in her soft hands and said, “I am cooking dinner for both of us tonight. Why don’t you go and sit outside in the drawing room. You should watch television and relax. Hard working man like you should get to have some relaxing time. Leave the cooking up to me.”, Chetna said nonchalantly. She had already tucked her pallu like a housewife ready to work in the kitchen. She had her hair tied in a bun. Her blouse was tightly hugging her figure. Her fake breasts were pointing and looked large in that blouse. I was trying hard to avoid thinking about sex, but it was impossible to avoid those thoughts with Chetna’s beautiful body in front of my eyes.

“I can do the cooking today. You don’t have to do this (pause)…. Chetna.”, I didn’t really want to say Chetna’s name, but I could not call her Chetan. She was too gorgeous a woman to be called Chetan. “Hmm… would you like to cook with me instead?”, Chetna said. She was smiling at me. Was she trying to tease me? But cooking with her didn’t seem like a good idea. “Err.. no!”, I denied the idea strongly, “You can cook tonight. I will… I will … go out and watch TV”, I was already at loss of words. I stuttered. Beautiful women can have that kind of impact on men. And Chetna looked too pretty for me to think straight with a clear head. I was not really expecting Chetna to appear today, not before I cleared things with Chetan first. But here she was, truly messing my head. God! save me tonight. I prayed to god to give me the strength to deal with this situation. I didn’t want to do anything wrong.

I came out to the drawing room, and started watching TV. I could still see Chetna cooking dinner in the kitchen. I was trying to remind myself that this woman is my friend Chetan, a man! But in that saree with his hair tied in a bun, he looked like a perfect housewife. His golden bangles he wore in his hand made a tinkling sound while he/she rolled chapatis. In the heat of gas stove in the kitchen, she would occasionally pull her hair back from her face, and wipe the sweat off her face with her pallu. She acted like a perfect woman. Her soft round big ass shining in that saree was inviting me to touch it, grab it, and pinch it. But there was so much going on in my mind. I tried putting my attention on the TV, but my eyes would wander again and again to see that hot beautiful woman in the kitchen. Was that woman my friend Chetan, a man wearing a saree, or a woman named Chetna? My mind could not decide. All I knew was that the sound of her tinkling bangles made me crazy.

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When Chetna noticed, I was staring at her. She quickly turned around, let her pallu fall open and wrapped it around her body. Oh how attractive she looked!

Chetna came out of the kitchen after some time. She had a big smile on her face. She was wearing a dark colored lipstick tonight on her lips. I so wanted to kiss her lips, and make her mine. But I didn’t. My eyes fell on her exposed waist this time. In the heat of the kitchen, she was perspiring and I could see a few drops of sweat on her waist. Her waist looked really sexy even with that sweat. I wanted to kiss on her waist.

Chetna brought forward her saree pallu to wrap it around her waist to cover it. She said to me, “Nishant, dinner is ready. Why don’t you sit on the dining while I set the table?” She still had a big lovely smile on her face, as if she just finished cooking for her husband. Is that woman a he, or a she? I didn’t know. And I didn’t care.

I sat on the table. Chetna brought a plate for me; she stood right besides me and started serving food. Her blouse filled with her big fake, but soft breasts was right in front of my eyes. I so wanted to bite her boobs. Her fleshy arms in the tight medium sleeves of her blouse looked amazingly hot. “I have made your favorite dish tonight. You like gobhi(cauliflower). Don’t you?”, she said really femininely as if my wife was talking me. I nodded my head in yes.

After serving the food, she sat in front of me. She put her arms on the table. She kept looking at me with a smile. “Try it, and let me know if you like my cooking.”, she said again lovingly. She was a loving woman. I kind of felt happy inside to have this woman in my life, but I didn’t want to tell her that.

“Really delicious, Chetna. You too should eat with me”, I said.  “Sure, I will eat too. I want to make sure that you are fed well. I would love that.”, she said. My mind had once again decided to forget that this woman is my friend Chetan. Chetna, the woman, was once again dominating my mind. She started making a plate for herself. “Be honest, Nishant. Did you really like gobhi? I made it with love for you. I really hope you like it.”, Chetna said. It was amazing how Chetan becomes a perfect housewife after wearing a saree.

We continued to eat our dinner silently. Chetna would look towards me occasionally and smile. Unlike Chetan, Chetna ate slowly and took small bites. Just like a woman. I don’t know if Chetan had learnt this behavior, or he had it in him all along. I could still see Chetna’s sexy bulging chest. As expected, her saree was continuously slipping away exposing her blouse. And like a true woman, she kept covering it. Once when she noticed me staring at her breasts, she looked back at me making her eyes bigger as if she was angry at me. I started eating again. But soon I noticed that Chetna was touching my legs using her feet. She was such a tease! Was she still thinking of sex? I decided to pull back my legs. She looked a little disappointed.

“Nishant. Can I say something?”, Chetna said. “Yes, sure.”, I replied.

“Yesterday, you promised me that my cross-dressing is not going to change our friendship. But you are not even talking to me today.”, Chetna said. “Yes, I had promised Chetan that we will still have our friendship. But Chetan is not present here. Is he? And I made no such promise to Chetna as far as I remember”, I said angrily. I was still confused how I felt about Chetna and the whole matter.

“You are right, Chetan is not here. But you can talk about Chetna, right? Do you realize how hurtful it was when you left me on the bed without saying anything to me this morning? You could have at least given me a good morning hug, or at least said a few words? It seemed as if you no longer cared for me once your physical desires were fulfilled. I felt as if I am just a …”

I stopped Chetna from saying anything further. I almost shouted at her. “Stop it, Chetna! I am not gay! I don’t like men that way. We can’t have physical relations between us.”, the confusion inside me was now out. I was tired of what was going inside my heart. I liked this woman but couldn’t be with her. I had said these words in anger, but it didn’t seem to impact Chetna at all.

“I knew it. I knew it that you will think like that. Nishant, you are not gay!! Let me repeat it, you are not gay! The person you made love to last night, was a woman, a special woman. You saw a woman in me, not a man. You were attracted towards a woman.”, she tried to console me as she grabbed my hand.

“But what about you Chetan? You made love to a man last night. Didn’t you? You were never a gay man. Then, how did this happen? What kind of relationship is this?”, I asked Chetna.

Chetna’s eyes were soon filled with tears. “I don’t know Nishant.”, she screamed. She started to cry. “I don’t know, Nishant! The person who made love to you last night was not your friend Chetan, it was me. It was Chetna, a woman. I received love from a man yesterday. First time in my life, I met someone, a man, who acknowledged that I am a woman. No one ever had did this for me. And as my gratitude, I dedicated myself to this man last night. How can I explain this to you that Chetan might like girls, but Chetna …  she probably loves a man.”

“Please stop your drama, Chetna. I don’t even know if I am talking to Chetan or Chetna! This is too confusing.”, I said as if I didn’t care about her. But deep inside my heart, I had started caring for this woman.

“Is this confusing for you? What about me? You will never understand me, Nishant.”, Chetna said looking down while wiping her tears.

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I left Chetna there alone. How cruel I was to leave her sad?

I soon finished my food on the plate and took it to the kitchen. Chetna remained sitting there crying. I was too harsh on her. She saw me behaving cold towards her. She couldn’t take it any more. She ran towards her room still crying. She remained lying on her bed with her head pushing down. She was silently sobbing. I could not believe that this woman was my friend Chetan. Can he be this emotional? I could not believe. But I was realizing my mistake.

May be I should go inside and console Chetna. I couldn’t leave her sobbing like this. I got in where Chetna was lying in her bed. She was still sobbing. She hid her face from me. In a situation like this, I should not have felt this way, but she still looked too sexy. I felt ashamed for my sex-related thoughts. I sat next to her. I could see her fleshy back in that satin saree blouse. It was very inviting. I saw her naked waist, her round big hips, her each body part was tempting me.  But this was not the time to think about those things.

I put my hand over her back to console her. “Chetna, I am really sorry. But I need sometime to resolve this matter between us. I cannot understand what is going on in your heart. What can I do? I don’t even understand my heart too? We two will become good friends once again, but we both need some time to fix this.”

Chetna kept crying silently. She didn’t say anything. But my heart told me that I should do something soon. My mind could not think of any solution. Suddenly, I noticed something in her room. I had an idea. I got out of her room and went back to mine.

The thing that I wanted to do now was really a time-consuming and difficult job. After around an hour of planning and acting on my plan, I went back to Chetna’s room. The lights in her room were off. Probably, Chetna had gone to sleep. I turned on the lights.

I tried to wake up Chetna as I nudged her legs with my hands. “Chetna. Chetna. Please wake up.”, I said. She didn’t respond. But I was excited now about my plan. I jumped into her bed. I knew that my plan was going to work as long as Chetna wakes up.  “Come on, wake up dear.”, I said again. She was still not moving. After all, she was angry with me. She was angry just like any other woman. I slowly started to press her soft ass with my toes. I knew it that the touch on her ass would definitely wake her up. But she didn’t. I tried harder this time. And there she was. She jumped up into her bed.

“What’s the matter?”, she shouted as if angry with what I did. But when she looked at me, her anger vanished and she began smiling. “What’s this, Nishant?”, she began looking at me from top to bottom. Why wouldn’t she? After all, I had somehow managed to wear Chetna’s saree with a lot of difficulty. I was trying to hide my face behind the saree pallu.

“You earlier said that I cannot understand you. So I thought why don’t I wear women’s clothes like you do, and may be I will understand you a little better.”, I said. Chetna was laughing now.

“You know it was a tough task to do! I had to go through some website to learn how to wrap a saree around me. I know that I am bigger than you, so I was not sure if I would fit into your blouse. But I managed to wear it anyway. I could put on almost all the hooks except for the two at the bottom. I can barely breathe Chetna!!”, I was laughing at my own act.

“Nishant! You are too much!”, she continued to smile, “Do you know that the saree you are wearing is not mine? I had purchased that for my mom, and the blouse was a readymade fit for her and not mine. You won’t be able to slide your arms in my delicate blouses.”, Chetna said. She looked like a delicate princess. She had changed her clothes before going to sleep. She was wearing a red satin night dress. Needless to say, she looked hot!

“Ohh! That’s why this saree and blouse were packed perfectly as if new. I am sorry, Chetna. You will have to buy a new saree for your mom.”, I said.

“No problem, Nishant. I can’t give this saree to my mom now. I would find it weird to give it to her especially after seeing you in it. No problem, I will keep this for mine. I just need to tighten the blouse a little bit. “, Chetna said laughingly. I was happy to see her laughing.

“OK, OK. All that is fine. But you haven’t told me how do I look in this saree? Do I look like a hot model?”, I acted like a woman. I knew my acting was terrible and I looked ridiculous in that saree. First of all, I didn’t know how to wear one. Second, my arms were too big and hairy. And finally, I didn’t know how to do make up at all. I didn’t mind any of those flaws. I only wanted to tell Chetna that I will try my best to understand her. I once again acted ridiculously and asked her, “Oho, tell me how hot do I look?”

But instead of seeing happiness on Chetna’s face, there was anger once more. “I knew it. I knew it that it’s a big joke for you. You want to say that I am some weird person who just likes to behave like a woman. “, Chetna said.

What the hell? That’s what I thought. I came with very good intentions to fix everything with Chetna, but the end result was once again the same. My happiness was gone from my face too. I sat there and thought for a while. I said to Chetna, “Yaar , I am really done with girls. It’s so difficult to understand them. No matter what you do for them, it’s never enough for them. Here I am dressed in an infinitely long unmanageable saree in an effort to understand the heart of this beautiful woman sitting besides me, but she got angry once again. I really don’t understand you girls. I don’t know what else I could do. I am done with you women!”, I complained.

What I had just said, I used to complain like this with Chetan whenever my relationship would end with any girl I had met in my life. I used to say to him that I will never be able to understand girls. Chetna was familiar with my complaint.

“Are you saying truth, Nishant? Were you trying to understand the heart of this woman? Do you really consider me a woman?”, Chetna’s heart was melting away fast. After all, I had just made her realize that I see her as a woman. And like any other woman, she was as difficult to please. The lost smile was coming back on her face.

“Yes, I am telling the truth. There is no difference between you and other women. You girls do a lot of drama. Why don’t you girls tell directly what is it that you want?”, I said to her. I looked into her big eyes. I wanted to dive deep into her magical eyes.

Listening to my words, Chetna came closer to me and hugged me. “Now that you are already wearing a saree, let me teach you a few more things about being a women. Let’s see if you can dance like one.”, she pulled up my hand as she stood on the bed. She began to rotate me like men rotate women while dancing. I started feeling dizzy but my saree furled beautifully in the air. I managed to see a smile on Chetna’s face. And I loved it.

“Ok, Chetna. I should go to sleep now. You should go back to sleep as well. It’s already very late now.”, I hugged her to say good night. I really didn’t want to leave her alone. I wanted to hug her all night.

“Nishant, if you want, you may sleep next to me.”, she said blushing. She couldn’t look into my eyes as she requested. “Hmm… Let’s see. I will sleep here only if you tell me that you want me next to you.”, I started teasing her. She said yes in a low voice. I hugged her back with a lot of love. I was really happy now.

“But Chetna, I don’t think I will sleep in peace when I am wearing this heavy saree.”, I said. She laughed at my predicament and said, “Don’t worry dear. You will be fine. You will learn a few things about how much problems we women face to please you men.”

“Chetna, I want to say something important to you. Please don’t feel bad. I feel that we should avoid physical relationships until we understand how we feel about each other”, I said. She nodded in yes. She understood what I meant to say. I didn’t want to jump into the bed again when our emotions and feelings were not clear about each other.

“OK, Nishant. But you better keep your hands in the right place. Don’t touch me like you touched me last night!”, she warned me. Her eyes suggested mischief. I laughed at her comment. I knew it was going to be difficult to resist touching her.

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Chetna tucked me into the bed. That was the first and the last time I wore women’s clothes; all because I wanted to please the beautiful woman in my life.

Later, Chetna tucked me into the bed. I needed her help to figure out how to sleep in that tonne of a saree. Thankfully, I was not a cross-dresser. I never wore women’s clothes again in my life.

Chetna was now in my arms. Her buttocks rubbed against my body. I held Chetna’s warm body tight in my arms. I could feel a growing sensation in my genitals. And Chetna could feel the hardened penis too. “Keep that in control tonight, Nishant”, Chetna said teasingly. I felt like kissing her, but I didn’t do anything sexual that night. And I am glad, because this was the start of a loving relationship between us. The love that was soon going to blossom.

To be continued …

Author’s note: There is a lot more in this love story. I hope our readers are eager to know what happened next. Stay tuned. We will be back with the following parts. Don’t forget to give us your star rating for the story on the top of this page! Do tell us if you like this story.

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