Sex Escapades With Rupa Ma’am

Hi Readers, This is my first sex story. I have been a regular reader of ISS for a long time and wanted to share a real-life experience. So without boring you all, I am coming straight to the story. My name is Rahul. I am 35 years old and I live in Mumbai.

This story is about my sexual adventures with my college crush Rupa Chakraborty. Like every normal boy, I too have had multiple crushes on my teachers. But Rupa Ma’am was different. She used to teach us English in class 12 and that was the time when I was in my adolescence.

I am not sure how old she was. But she was the epitome of beauty and sensuality. She must have been in her late 20s. She used to wear saree to class. She was unmarried at that time and used to wear low back blouses. I used to feel multiple sensations whenever I was in her class.

I had made a habit to sit on the first bench in order to appreciate her glowing beauty. I had slowly become her favorite and my friends used to tease me as teacher’s pet. But it didn’t matter as I was happy in my own fantasies. It was the month of April.

Considering the humid weather of Mumbai, Rupa used to wear light sarees. The material was almost see-through which made me see much more than normal. I always used to find opportunities to gaze at her blouse. Her boobs were huge; she must have been a 36 D at that time.

Our classes were not air-conditioned. In the afternoon class, Rupa used to sweat. Whenever I looked at the droplets of sweat on her waistline, I wanted to lick them off. She used to wear a very sensual fragrance. I always looked for opportunities to come close to her.

As luck would have it, I got an opportunity in a month’s time. Our school was closed for summer vacation. I asked my parents if I could take English coaching from Rupa during the vacations. They agreed, but the problem was to convince Rupa. Unlike other teachers, Rupa never gave personal tuition.

A week before summer vacations, I gathered courage and asked Rupa regarding the same after class:

I: Ma’am, can I talk to you for 10 minutes, I have something to ask you about?
Rupa: Sure Rahul, tell me.
I: My parents have not made any plans for the summer vacation. They want me to focus on examinations. I am thinking of taking tuitions during the vacations. I wanted to take English tuition from you.

Rupa: Sorry Rahul, I don’t take tuitions and I have plans to go outside Mumbai. You should check with someone else.
I: Ma’am, I know you don’t take tuition. But I want to learn from the best. I am requesting you if you can make out some time for me.

Rupa: Okay, since you are a very hardworking student, I will help you. But there are two conditions. First, I won’t take money from you and second, you will have to come to my place for this. I will go out of Mumbai for a week, so that week obviously we won’t have classes

I was so happy with her response I felt like hugging her tightly, but I controlled. Vacations started and I was a step closer in my mission to fuck Rupa. I had told back at home that she will take Rs 5000 per month. I wanted to have more money to impress her.

My parents were hesitant with this high amount, but I convinced them. Coming to our first class. It was Saturday and I had reached Rupa’s home on time. It was 5 PM, I rang the doorbell and the door opened, standing in front of me was the lady of my dreams, Rupa. She was wearing a t-shirt and jeans.

She was looking like a teenager. I stared at her for a good time. Her yellow t-shirt was tight at her breasts. She had rolled on her sleeves a little which gave me a glimpse of her shaven underarm. When she turned I noticed her jeans were hugging her ass and as she started walking.

It felt as if her ass was inviting my cock. I was on the verge of getting a boner. She sat on her sofa and asked me to sit on the one next to hers. I sat. It was me and her in her 1bhk. Her fragrance was making it hard for me to resist. I wanted to grab her and fuck the hell out of her. But I controlled.

Then her phone rang and she went to the room to take the call. While I was waiting for her to come back. When she came she was not in a good mood and asked me to go back. I didn’t understand but had to leave. Then classes were going normal for the next couple of weeks.

I was nowhere near my desire of fucking Rupa Ma’am. I needed a plan and I needed it urgently as she was leaving for her vacation next week. Then I would have met her directly in school. The next class, I dressed up well and wore my dad’s expensive fragrance to class.

During the class, I gathered courage and asked Rupa, ” Ma’am, why are you so sad these days?” Rupa told me that she is fine and asked me to focus on the chapter. I gathered courage and went near her, held her hand. Before I could open my mouth she slapped me. I was shocked, and my eyes were teary.

Rupa: I am sorry; I didn’t mean to hit you.
I: I am sorry Ma’am, I thought I can ask you things and comfort you during sad moments.

Rupa was extremely apologetic and I was thinking of capitalizing the situation. I told her I am fine. But she should tell me about her problem and she agreed.

Rupa: I don’t know how to tell you. You are my student. But anyway, I have a fiancée and things were going great between us. But now he is not willing to commit to marriage.

I: He must be stupid Ma’am. Who would not want to marry you!
Rupa: Shut up! No need to be nice!
I: If I was older, I would have killed to be your fiancée.

Rupa smiled and we went back to studying. Something changed after this discussion, Rupa became more friendly to me. She would touch me more while correcting me during the class. Now came our last class before vacations. I had given up hope that anything will happen.

But little did I know this would turn out to be one of the best evenings of my life. I knocked on Rupa’s door and there she was clad in a purple saree with her low back blouse greeting me to come inside. I got lost in her beauty. Her pallu was not properly set and I could catch a glimpse of her milky cleavage.

I wanted to immerse my face in those mounds at that very moment. I wanted to rip her saree apart and suck on those milky boobs for the rest of my life. Her white soft breasts were luring me and I was thinking of a reason to touch them. I was horny to the core and the boner in my pants was hard to hide.

We started our class and halfway through I thought of a plan. I asked Rupa if we can have a short class. Since it is our last class during the vacation can we go out? To my surprise, Rupa agreed instantly. We planned to go to Juhu beach. When we came down her building, I asked her if it is okay for her to come on my bike.

Else we can book a cab. Rupa was hesitant at first. But I convinced her. I had left my bag at her place so that I can feel her while riding the bike. Rupa sat cautiously and had placed a hand on my shoulder.

We went to the beach. Took ice creams and started walking. I thought of starting the conversation:

I: Ma’am, is everything sorted with your boyfriend?
Rupa: He is my fiancée Rahul and I don’t want to talk about him. Let’s talk about you, do you have a girlfriend?
I: Yes, and no.

Rupa: What does that mean?
I: She doesn’t know that I like her. But I have considered her to be my girlfriend in my mind.
Rupa: You should talk to her.

I: I am scared, what if she doesn’t like it?
Rupa: You are such a nice guy Rahul. No one can reject you. Just be a man and ask her out.

After hearing this, something happened to me. I held Rupa’s hand and said, “Ma’am, I really like you a lot! Will you be my girlfriend?” Rupa was a little shocked by this. She said: “Don’t be mad, I am your teacher.” But I was in no mood to get rejected today.

I pulled her little closer and placed my left hand on her bare waist. I grabbed her waist firmly and said, “Rupa, you are my teacher in school. After school, you are the woman I love. I won’t let this come in our professional relationship.” Rupa was shocked, but she didn’t push me away.

I got the hint and slowly came close to her. My lips were very close to hers and we both were breathing heavily. I placed my right hand on her waist too to complete the embrace and touched my lips to hers. I didn’t know how to kiss. This was the first kiss of my life.

Rupa understood that and she kissed me back. She sucked my lower lip for some time and bit it while breaking the kiss. I got excited and started to suck her lips wildly. She stopped me and said, “Easy tiger, I am going nowhere.” We kissed again. This time she inserted her tongue inside my mouth.

I started sucking the tongue like a baby sucks nipples. Then I slowly inserted my tongue in her mouth and she swirled my tongue inside her mouth. I got very excited and my boner was poking Rupa from her saree. We continued kissing for 15 minutes on the busiest beach in India and then we broke our kiss.

Rupa: Rahul, your cock is throbbing a lot. I will have to calm it down. After all, you are my favorite student. Let’s go back home and see what your cock can do.

I got so excited after listening to this, but the only words that came out of my mouth were: Yes, Ma’am.
Rupa laughed. Kissed me again and we came back to the bike. The ride back home was heavenly. Rupa’s boobs were pressing against my back. She had grabbed my waist with her left hand while her right hand was feeling my cock. I was out of control. But Rupa was in no mood to stop.

I never thought she would be this wild. We rode back and Rupa ensured that my cock was fully erect throughout the trip. There were times when I was about to come but Rupa was a pro. She knew how to handle a virgin cock. We reached her house and then entered the building properly.

As soon as we entered the lift, we looked at each other and started kissing profusely. My hands were all grabbing Rupa’s ass and she was holding my neck. Luckily, no one entered the lift and we continued doing this till we reached her floor. She opened the flat’s door and I was standing behind her.

As soon as we entered I grabbed her boobs from behind and started squeezing her boobs. Rupa was moaning like a bitch and I was in no mood to leave her. I grabbed the pallu of her saree and unwrapped it in within seconds. All I could hear were Rupa moaning and saying. “Come on baby. Fuck your teacher!” These words were turning me on even more!

Rupa was in her blouse and petticoat. Her body was turning warm because of the excitement and she was in deep ecstasy. While I was opening the hooks of her blouse she was unbuttoning my shirt. Her hands were exploring my chest and in between, she used to pinch my nipples.

Within moments, her blouse and my shirt were lying on the ground. I was going to unhook her bra. But she stopped me. Now she was taking control. She turned me to the wall and opened my belt. Then she unbuttoned my jeans. Her hands were inside my jeans and she was poking my cock with her nails.

I was enjoying this and had my eyes closed. Before I realized my jeans and underwear were pulled down by Rupa. She was on her knees holding my 6-inch cock in her hand. She had gripped my cock firmly with her right hand and was sliding it up and down across the length of my dick.

She was twisting it time and again as if she was measuring the width of my dick. I looked at her and this was a sight worth dying for. My Rupa ma’am was in her bra and petticoat looking at my cock with all excitement. I untied her hair while standing and grabbed her head.

She looked at me and then kissed the head of my dick. All of a sudden she stood with a tighter grip on my cock and started taking me to the bedroom. She was walking with a firm hold on my dick. I was grabbing her ass from behind. Within that 10 feet walk from living room to bedroom I untied her petticoat.

She was now in her purple bra and purple lacy panty. I was in ecstasy now and wanted to fuck Rupa then and there. As soon as we reached the bedroom I threw Rupa on the bed. She was lying on her tummy. I jumped on her with my cock sliding between her ass cracks and my chest on her back.

I unhooked her bra and pulled her panty down. Then I turned her and there she was my Rupa completely naked lying in front of me. Before Rupa could realize I started sucking her breasts like a toddler. I was biting her nipples in between.

Rupa: Oh baby! you are turning me on, suck these boobs. Suck them like a baby, my baby!
I (while sucking the boobs): I am going to fuck you Rupa, this body is mine! You are mine! I love you!

Rupa: Fuck me, my baby, I am all yours. No one has sucked these boobs like this. I want more! I want you to fuck me hard. Make me your bitch!
I started to go down on Rupa, after sucking her boobs and biting her nipples for 10 minutes. I was on her tummy digging that deep navel with my tongue.

Rupa: Fuck every hole in my body, make me your whore Rahul! Don’t be gentle on me!

I was getting turned on by listening to all this. I never thought Rupa Ma’am would be this wild. I went even further down and started sucking her clit. I took two fingers and inserted them into her vagina. I started to finger fuck her with my right hand while my left hand was squeezing her boobs.

Rupa had lost control and she started screaming in Hindi, “Behenchod, kya kar raha hai! Zor se kar!”

I got mad after listening to her like this. I was in no mood to stop. I was ramming her vagina with my fingers. Now there were three fingers coming in and out. The room was filled with her moaning. Then she came all over my fingers. I licked every drop of her juices.

I: You had your fun. What about me (pointing towards my throbbing cock)?
Rupa: Don’t get impatient Raja, I will take care of this. (she winked)
I: You sound like a slut on the bed.
Rupa: You don’t like it, baby? (she grabbed my cock and pushed me)

I: I love it when you get slutty. I feel like spanking you hard.
Rupa: Who has stopped you? Spank me, baby!

Before I could do anything, she took my cock in her mouth and started sucking it. I was in a different world. I had only seen blowjobs in porn, never realized that the feeling of a blowjob is so amazing. Rupa was a professional in cock sucking.

She was sliding her tongue from the head of my cock to the balls licking every inch of it. Then she used to suck the balls for some time, squeeze them with her mouth. It’s hard for me to explain the feeling of my balls getting squeezed and touching each other.

I could feel a slight pain with a lot of pleasure. Then she licked the whole length of my cock, slid my foreskin and took the whole of cock in her mouth. She was doing it fast. I was about to come. She put her thumb on the opening of my cock and said, “Itni jaldi kya hai, sabar kar saale! Let me suck this sausage properly.”

Itne dino ke baad I have got something. Let me feed myself.”
I: “Ma’am, it’s very hard to control, you are a pro!”
Rupa: “Bache, be a good student and let whore Rupa make you a man!”

After saying this she went back to sucking my cock. She sucked it like a whore and I had closed my eyes feeling her movements. She had grabbed my ass now and was sucking my cock as if it was her lollipop. I opened my eyes and saw her in complete ecstasy sucking my cock from top to bottom.

I couldn’t control myself further and released my whole load in her mouth. She looked at me, winked and gulped all my semen. Then she came up and kissed me for a good 5 minutes. We both were tired and were lying on the bed.

Rupa: Hope you had fun, young man!
I: Yes Ma’am, but I really wanted to have sex with you.
Rupa: We will have it next time, I am content right now, hope this will remain our secret!

I: Yes, Rupa.
Rupa: Okay then, you should get going, your parents will get worried.
I: I was thinking if I can stay some more time, maybe we can do round 2 then.
Rupa: Don’t be impatient Rahul, we will have many more opportunities!

Saying this she kissed me deeply. I had no other option than to leave. So I wore my clothes and Rupa hugged me from behind, “I will see you. Take care!” I turned, we kissed again and I left.

School opened after a week. I found out that Rupa Ma’am had left school and was getting married in Kolkata. I didn’t understand why she didn’t tell me about this. I was sad and thought the most exciting phase of my life had ended. But destiny had other plans.

I will tell you about destiny’s plan in the second story in the series. Feel free to send your feedback at [email protected].