CoupleIndian Sex Stories

From a Student to a Sissy!

Hello, This is Rahul here. I am an MBA student in a reputed institute in Bangalore. I am in my final year right now. This is a real story that happened to me this year itself.

We are supposed to do an internship in a company. Most of the time, college only allocates company by conducting interviews. I was selected with Aisha from my class for the same company. It was a six-month-long internship.

My rented flat was near her hostel. So we used to go together on her scooty. Our timings were 11-6 Monday-Friday.

The first week was great. We both were on the same project. Our team was a 4 member team consisting of Aisha, Meera Ma’am- our boss/team lead, and Krish – another intern.

To describe everyone, I am 21 yrs, 5’9″ with a lean build, dark in color. Krish was 22, 5’6″, fair but a little chubby. Aisha was 21, skinny, 5’5″, very fair. Our boss, Meera Ma’am, was the model. She was 26 years, 5’10”, with amazing features and hair. I wondered why she isn’t in modelling!

Now, returning to the incident, we were provided with the laptops from the company. But foolish me, I logged into my Gmail account in the browser. All my browser history, password, etc., from my laptop, were synced in the office laptop.

It had all my history of BDSM, femdom, sissy, pegging, cuckold porn sites, and history. And I didn’t even realize what was done.

In my second week, I was given some work, but I could not do it due to some software issue. I told Meera Ma’am, and she told me to leave it on her cabin table to check for a solution. The next day, she gave me another laptop and said the previous one had some issue.

When everyone was leaving in the evening, she gave me some extra work. She asked me to complete it by the end of the office itself. I was tired, but when I realized that even Meera ma’am would also be working with me till late, I got the motivation.

I was working in my cubicle when she called me to her cabin.

Ma’am: Rahul, it must be hot outside. Bring your lappy in here. AC is working here.

Me: No worries, mam. I am good.

Ma’am: Are sharmao mat, aajao. (Don’t be shy, bring your work inside) Mujhe bhi company mil jayegi. (I will also get company)

Me: Okay, Mam.

I brought my phone and laptop inside and sat opposite her across the table. So basically, she had her chair on one side of the large rectangular table. I sat across her on one of the three chairs.

She wore a black shirt and a white skirt to her knees – typical office wear, elegant and sexy. I was turned on a little. I could even spot her white bra in her thin black shirt.

While I was working, she printed out something and told me to get it. The printer was outside the cabin in the common area. I collected the paper and just glanced over them. The document was titled Rahul and had all my porn history printed in bold with my IP address and all. I started sweating.

With trembling feet, I entered her cabin. She was busy typing something like nothing had happened. I was holding the papers and just standing at the door. No reaction from her- still busy at work.

After a minute or two, she scolded me, “Why are you standing over the door like a statue? Put the papers on the table and continue with your work.” I was dumbstruck. Does she not know what these papers had on them? Or I accidentally printed my history and picked up the wrong papers.

She again gave me an angry look, and that was enough for me to put the papers on the table. I was barely able to continue my work. I was repeatedly looking at her for a clue as to her intention. Nothing. Nada. Silence is the worst kind of torture.

After about an hour, about 7:30 pm, she closed her lid. She was beside me and sat at the table. I could see her skirt rolling up while she sat and saw her milky lower thighs. She crossed her legs, and her matching black heels and naked feet came in front of my face. Then she asked me about my work status.

Me: Not completed, mam.

Ma’am: (in an angry tone) Do ghante se yaha baithe ho, ac ki hawa khane thode hi bithaya hai! (You were sitting here for two hours and didn’t finish your work? Are you just enjoying yourself in the AC room?)

Me: (very softly in a scared tone) Sorry.

Then she picked up the printed papers and started reading a few of the titles from my history: Cuckold humiliation porn, femdom porn, teacher porn. I looked down in shame.

Mam: So this is what you do instead of work!? You are pathetic. I will have to fire you for infecting the company laptop with viruses.

I was shit scared. I would not get a new internship in between the terms now. Getting fired from a company is also not good for my career. Plus, everyone would know the reason behind it. I begged her asking for forgiveness. I legit started crying. She was very adamant in her decision.

After 5-10 minutes, she said, “I could give you a chance, but you will have to obey everything I tell you to do.” I immediately agree. A smile came on my face hearing that. She asked me to bring 10 blank papers from the stationary room and sign on the bottom of every page.

I didn’t know how or when she was going to use it. Then, she typed and printed a resignation letter that stated that on one page.

“I, Rahul, hereby resign as an intern from the company. I am ashamed of sexually harassing my coworkers and will not do it again. Sorry for the misconduct.”

I looked at her. Before I could say anything, she slapped me hard and told me, “This is my insurance policy. I will use it whenever you disobey me.” I signed that un-dated letter too.

After that, she told me to strip down. I looked at her shockingly. She again slapped me on the other cheek. I started removing my clothes hesitantly. I was in my boxers and was embarrassed to remove them. She was so furious that she took scissors from the drawer and cut them herself.

I was naked in front of her. I hid my dick with my hands. She told me to stand properly and show her everything. I removed my hands and turned around. She clicked many pictures of me nude and laughed at my dick size.

It was around 3 inches that time. Her laughing turned me on, and it grew to 4 inches. I looked at her with a proud grin.

She told, “Abay chutiye, mere boyfriend ka 6-inch ka loda hai jab woh erect bhi nahi hota hai. Teri nunni uske 10-inch ke laude ke samne mungfali hai. Samjha bhosdike?”

(Ay moron, my boyfriend’s dick is 6 inches when he is not even hard. Your man-clit is nothing compared to his 10-inch erect dick. Understood, asshole?)

I stopped smiling. Then she ordered me to lick her heels and feet without using my hands. She tied my hands at my back using my tie. I fell multiple times while licking as I didn’t have support while bending down. After licking her feet and legs for an hour, she stood up.

She then ordered me to remove her clothes using my mouth. I started unbuttoning her skirt. After a few minutes, the button came off. Then I pulled the skirt down by pulling it using my teeth. The way I was pulling, the aroma of her pussy made me mad.

She was wet, as easily seen by the wet spot on her white panty. I gently gave a lick on her panty, and she felt that and tapped me on my head. “No pussy without permission to you loser.” Disappointed, I pulled the skirt down the rest of the way.

Then I stood up and wondered how I would unbutton her shirt. But then, mischievous me decided to remove her panty first. I raised her shirt using my head put my teeth below her navel. I started dragging them towards her panty. It hooked her panty easily.

This made her moan. I pulled down her panty by my teeth, making her pussy scratch. Her clean, shaved pink pussy had a well-trimmed landing strip above it. It was beautiful. I clicked billions of mental pictures of it before the shirt fell, hiding her lower lips.

I see the first pussy in my life, and a damn shirt is blocking my view. I became mad to open her shirt. I was never hard like that before in my life. Pre-cum was oozing out of my penis. But the shirt buttons are not easy to remove with your teeth, without help from your hands.

I struggled for 10 minutes, and she was moaning by the effect my mouth was having on her navel. After she had her pleasure, she removed her shirt and there they were. Two milky white boobs in white panties. Firm and barely able to hold in the bra.

Just as I was about to use my mouth to lick her boobs in the context of opening the bra, she put her finger on my lips, stopping me midway, “Don’t be over-smart, Rahul. My bra opens from the back.” She then turned around, and I saw her sexy back.

She pulled all her hairs in front from one side, and that, my friends, is the best view anyone can ever give. I started removing the bra and got it off in 2-3 minutes. Like a hungry dog, I started pulling the bra, which got her angry. She turned around, her bra fell.

As I was pulling it, it was hanging by my mouth. She smiled sarcastically and held my penis. I would have cummed immediately, but she moved further towards my balls. She caressed my balls and then suddenly pressed one of the balls. I cried in pain. “This is what you get to pull a stunt.”

Then she sat on her boss chair behind the table and told me to lick her pussy. I kneeled, and she spread her legs. I started licking her pussy. It was sweet and salty due to her wetness. I gave her oral pleasure for half an hour. I even gave a lick on her hair strip, and it tastes sweat-salty. I licked it clean.

She started closing her legs and holding my head on her pussy. Since it was my first time, I didn’t know what was happening. She orgasmed for full 4-6 minutes. As my hands were tied, I was helplessly suffocating between her legs. I had to dring all the juices flowing from her pussy.

After she was done, she rested on her chair. I was sitting on the floor looking at her wet pussy and legs. She smiled at me and said, “Tu tere muh se jitna sukh de sakta haina, uska 1% bhi teri nunni nahi de payegi.” (The amount of pleasure your mouth/oral sex gives, your dick will not even give 1% of it).

I was confused as to should I be proud I made her cum or embarrassed at my small dick. My dick was hard and now paining as no attention was given to it, my hands being tied. I told her, “My dick is hurting.” She shouted angrily again, “It is not a dick asshole. It’s a man-clit. Dare you call it a dick again.”

Ashamed, I looked down. She then looked at me with pity, “Oh! Don’t worry. I will take care of you. You don’t have to worry about it at all.” I thought she would untie me now and let me fuck her and lose my virginity. She untied me and told me to bring some lubricant.

I was very happy. I ran around the office naked, looking for some lubricant. There, on Aisha’s desk, I found moisturizer cream, and I took it. Back in the cabin, she was waiting, sitting on the table naked. My dick was all tight looking at her. She had got cello tape from her table.

Then when I came, she told, “You like BDSM na, let’s take your virginity in a BDSM session.” I was flying in the clouds. I came near her and was about to kiss her when she again slapped me and said, “Terko laga tu dominant hai? HA HA HA” (You thought you were the dominant one? )

Then she pushed me on the table’s edge on my stomach. So my stomach and head were on the table. My dick and legs were out. I wondered how I would fuck her pussy if my dick faced the table. Then she put a lot of cello tapes all over my hands and neck sticking me to the table.

If I tried to move, the tape pulled my hair like waxing. I was in that position for more than 10 minutes while she clicked my pictures, taking photos of me. After a long time, I felt cold below my balls. There she was rubbing the moisturizer on my asshole.

I had seen enough femdom and pegging porn to know what she was going to do. I screamed, asking and begging her not to do it. But she just replied, “This is how you will lose your virginity bitch.” She was continuously rubbing a lot of moisturizers and suddenly inserted a finger in my ass.

It went easily due to the cream. But that touched my nerves which I didn’t even know existed. I cum immediately on the table without even using my hand or touching my dick. I cum for a minute full, all while her finger was inside me. She didn’t move it a bit. She was also amazed at how easily I came.

Then she applied more cream on her fingers and slid it into my asshole. It was like she was lubricating my insides. She then slid her second finger, and I moaned aloud. I closed my eyes in shame, and she was laughing non-stop hearing me. She then kept moving fingers in and out.

Soon she entered three fingers. I was hard again by this act. She kept fucking me with her fingers. Her nails were scratching my ass from inside. I soon came within 5 minutes. I was exhausted, and so was she. But she wanted me to suffer for being the loser that I am.

She then picked up a marker, lubricated it, and slid it in my ass. The marker was longer than her fingers. I felt it reaching my intestines. She pushed it entirely and then removed her hand. She then told me not to do any stunts as I tried to remove it myself or masturbate my man-clit.

The angle of the marker will change, and it may get stuck. I was scared as hell. She also advised me to just take liquid food from now on. She then went to clean herself up without untying me. I was left in her cabin, tied to her table, cummed twice within 10 minutes and a marker up my ass.

She came back and wore her clothes. She untied me by harshly pulling off the cello tapes and then gave me her used panty (the white one). She told me to wear panties from now on instead of men’s undergarments. She threw my torn boxer in the dustbin.

And with her lipstick, she wrote, “This bitch is Property of Meera,” on my chest. She then left for her home by hugging me and slapping me on my bums. It made me feel the marker further up my ass.

There I was, alone, in my new office, naked, losing my anal virginity before my actual one, with my small useless dick. Sorry, man-clit.

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