The Saree Bet Ch. 01

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A college boy starts exploring his feminine side.
3.5k words
4.58
43.5k
42

Part 1 of the 3 part series

Updated 06/09/2023
Created 02/24/2020
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piyali19
piyali19
74 Followers

My name is Ishita. However, I didn't always go by this name -- I was called Ishaan before. I grew up in a middle class Indian family in the suburbs of Delhi. I was very shy and awkward growing up. And girls just scared the hell out of me.

I was around 5 feet 5 inches tall and had a slim body. I also had shoulder length hair. I had grown my hair over the holidays so that I could have a rock star look for college.

It was the first day of college and I was really excited. I was moving out of my parent's place and moving into the college hostel in Bangalore. I would finally be independent -- a new city full of new opportunities for the next phase of my life. It was also the day I met Saloni for the first time.

I had just settled into my room in the boy's hostel. They were individual rooms -- around 10 feet by 10 feet -- nothing luxurious, but still it would give me all the privacy I needed. My room was at the end of the hallway on the first floor. After unpacking my stuff, I went out and met with my neighbours for the next four years. In the room next to mine, was Aayush -- he was a local boy, from Bangalore itself. Pranav and Neel were in the rooms opposite ours -- they were both from Mumbai, and it seems they were friends from before.

The four of us soon became friends. After our introductions, we locked up our rooms and left for the orientation seminar scheduled for the afternoon that day. In the seminar, we were just given the basic rules and regulations of the college, a college map, our class schedules and such. After the seminar, the four of us thought it would be a good idea to explore the campus.

We were just exiting the building when I realised, I had forgot my orientation folder in the seminar hall.

'Why don't you guys go ahead. I'll catch up with you'll,' I told them.

'Sure. We'll head towards the basketball court. See you in a bit,' Aayush replied back.

I ran back to the seminar hall. It looked empty. However, when I entered, I saw that a professor and a girl were standing at the front near the stage. It seemed the professor was reprimanding her for some reason. I quietly moved towards the seat where I had left my folder and picked it up.

I was just leaving the hall, when the professor shouted, 'Hey you. What are you doing? Come here.'

I realised the professor was talking to me and reluctantly moved towards him.

He again repeated, 'What are you doing here? The orientation finished ten minutes ago.'

I nervously mumbled something about how I had forgotten my folder.

He retorted, 'Who knows what will happen of this generation. So careless and irresponsible.'

The professor continued, 'Good, at least you attended the orientation. This silly girl came late to the first day of college,' pointing to the girl next to him.

I shifted my attention from the professor to the girl for the first time. She was tall, around an inch or so taller than me, with dark brown eyes. She was wearing a loose fitting blue kurti with palazzo pants. She had her hair tied down in a single plait resting over her right shoulder. I could see that her cheeks were flushed red, probably from the embarrassment of being shouted at on the first day of college.

'Since you attended the orientation, I give you the responsibility of bringing this silly girl up to speed,' saying so, the professor handed over one of the leftover folders to the girl and left briskly.

Both of us were silent for a few moments and then the girl stretched her hand out and said, 'Hi, I am Saloni.'

Now I have always been shy around girls, but there was something about the look in her eyes that made me relax.

'Hey, I am Ishaan,' I replied, shaking her hand. I didn't know it then, but Saloni would someday turn my life upside down.

'I am so sorry to be a burden on you. But my train was late and then I didn't know my way here. The professor was just so rude.' Saloni said.

How could a pretty girl like her ever be a burden to anyone, I thought and replied, 'Don't worry about it. The professors just what to show who's the boss here. Anyway how can I help you?'

Soon I had brought her up to speed about the orientation seminar. After that we got to talking more -- I learnt that she was also from Delhi. Feeling a bit more confident now, I asked her, 'My friends and I are going to explore the campus. Do you want to join us?'

'Sure. That would be nice. I don't really know anyone else here,' she replied.

We met up with the rest of the guys and I introduced her to them. And soon enough our group of four had become five. We spent the rest of the day exploring the college campus.

* * *

As the months passed, the five of us got closer. We were in the same class and spent most of our free time together. Of course, Saloni being the only girl in the group, was the point of focus -- the remaining four of us always tried to get more attention from her.

One day, the four of us were sitting in Aayush's room in the evening chilling. Saloni had just left, as girls were not allowed in the boy's hostel after dark.

Pranav started, 'So who do you think among us, is going to make Saloni his girlfriend.'

Now, this was a topic all of us had thought about on our own, but never discussed it out in public.

I quickly replied, 'I get the first try. I am the one who introduced her to our group.'

To this, Neel replied, 'What's that got to do with anything? I am the most good looking of the four of us. She should be my girlfriend.'

Aayush said, 'I am the strongest of the four of us. I should get the first shot at her.'

Soon we were arguing, who had the best claim on her. Finally we decided, we would let Saloni decide and we came up with a plan.

Saloni had previously told us that over the weekend, she was going to receive a box full of her stuff from home and would need our help to move the stuff from the post office to her room. We decided that we would tell her that three of us have to stay back and only one of us could be spared.

We decided whoever she picked, would get the first shot at her.

* * *

The weekend rolled in. We were sitting in the college canteen having lunch. Saloni came in. She was wearing a wearing a pink and orange tight fitting salwar kameez. It accentuated her figure in all the right places.

And sure enough Saloni came to us and said, 'Hey guys. I need your help to move my stuff. Are you'll free now.'

Aayush replied, 'Actually we have some plans for this afternoon. We have to help out with the preparation for the college festival. However, you can take one of us, if you want.'

The four of us waited with anticipation to see who she'd pick.

She deliberated for a moment and finally replied, 'Oh. OK then. It's not like there is a lot of stuff. One guy should suffice. Ishaan why don't you came with me.'

Internally I was doing somersaults, but outside I casually replied, 'Sure. I'll help you out.'

Saloni and I left for the post office together. I looked back at the guys -- they looked really disappointed.

We picked the box of her stuff from the post office -- it was a small box and there wasn't really any need for my help either. But I was happy, I could take a shot at making Saloni my girlfriend.

On our way back, I started flirting with her. 'Who look really beautiful today Saloni. I like the way who've tied your hair'

'Thanks,' she replied back. 'You look nice too. You have nice hair. I could tie it the same way as mine if you want.'

I was a bit confused but didn't think much on it. I mumbled a thanks.

We reached the girl's hostel and I carried the box for her. She took me to her room. It was similar to my room in the boy's hostel. But, where my room was bare and messy, Saloni's room was very neat and smelled nice. The walls were full of posters of boy bands.

Some of her bras were hanging from a rope in one corner of the room -- I couldn't help but glance at them.

'Why don't you put the box on the table,' Saloni said locking the door behind her. 'Do you want some water?'

'Sure,' I replied placing the box on the table and sitting on her bed.

She came over with a glass of water but just as she was about to hand it to me, the glass slipped and she spilled water all over my shirt and pants.

'Shit, I am sorry. I'll get you some fresh clothes. Why don't you remove the wet clothes and give them to me,' Saloni said.

'What? I can't strip in front of you. You are a girl.' I replied.

'So what. We are friends. There's nothing to be ashamed of,' she replied giggling.

I was really confused now. Was she trying to seduce me? Hesitantly I removed my t-shirt and stripped out of my jeans. I was standing there in only my undershorts.

'Oh, it seems I have spilled water on your underwear too. Remove that too. Don't be shy,' Saloni said.

I removed my underwear and stood naked in front of her holding my hand in front, trying to cover my already hardening cock.

She came over with some clothes and handed them to me. 'Here you go. Get dressed.'

I looked down at the clothes and blushed red. There was a mini skirt with a tank top. On top of the clothes was a girl's panty.

'I can't wear these. These are girl's clothes,' I replied panicking.

'I am sorry, but I don't have any boy's clothes. And it's just for an hour or so until your own clothes dry,' Saloni said.

Seeing no other option, reluctantly I stepped into the panty and slid them up my legs. It was a bright pink bikini style panty. The panties didn't have enough space in the front and my cock kept popping out above it, so I tuck my cock between my legs.

Next I stepped into the skirt. It barely reached my knees. I put on the tank top. Even though Saloni was taller than me, the top was tight fitting and barely reached my navel.

I looked up at Saloni. She looked amused.

'Wow, you look beautiful. Had I not known, you could have easily passed for a teenage girl with a slim figure and small boobs. You even the have high cheekbones and narrow chin to make you look girly.'

I blushed red.

She went over to her cupboard and came back with something. 'Here, put this on too.'

It was a bra matching the panty I was already wearing. 'What... I can't wear that. Are you insane?'

But she came closer to me and soon coaxed me into it. By now I was in a trance and would have done anything she asked of me. I wasn't ready to admit it yet, but it felt nice to wear girl's clothes.

I removed the tank top and put on the pink bra. I had some trouble fastening it behind me but Saloni helped me with it.

I put on the tank top over the bra, but you could still see the bra straps -- there was no hiding them.

She took me by my hands and made my sit in front of the mirror. Then she started braiding my hair and tied it in a single braid which rested over my right shoulder. It was exactly the same way she had tied her own hair.

I stood up and looked at myself in the mirror. There was no denying it, I looked like a teenage girl, a pretty one too.

'You are very pretty Ishita,' she said, 'You know Ishita, I am not really a lesbian, but I have always wanted to experiment with another girl.'

I wasn't sure if I should be ashamed at being called a girl or be excited about fooling around with a girl.

She was taller than me. She easily put her arms around my waist and pulled me towards her. She moved her head forward and gently brushed her lips against mine for a second. Then she kissed me again more passionately, crushing her lips against mine. I responded back and she forced her tongue between my lips. Meanwhile our hands kept exploring each other's body. She had a firm ass and I pulled her against me, her breasts pressing against me. My cock was straining against the flimsy material of her panties. We continued kissing like this for minutes.

Then she pulled slightly back and I reluctantly broke the kiss. She smiled at me and pushed me back onto the bed. I laid back on my back and she climbed over me. She started kissing my neck, slowly moving down towards my breasts. She removed the tank top and pushed aside my bra and started licking my nipples. My nipples stiffened and she started biting them lightly. With her free hand , she started rubbing my cock over the skirt and panties. A few minutes of this was enough to push me off the edge and I was cumming in pulses.

Sensing my release, she bent down and licked up all the cum from my thighs and sucked my limp cock clean. She moved up and started kissing me again. She hadn't swallowed my cum and was feeding it back to me. I kissed her back eagerly. It tasted salty.

After a few more minutes of kissing, I wanted to return the favour. I twisted on the bed and climbed up on top of her. I started slowly unbuttoning her kameez -- all the while we continued to kiss. Under her kameez, she was wearing a red bra. I pushed the bra aside and released her breasts. She had massive breasts and her pink nipples were already erect. I started sucking her nipples, alternating between them every few seconds. She let out a soft moan.

I moved further down. She was wearing a while salwar -- I pulled it down her legs. Underneath she was wearing a matching red panty. I could see that she was already wet and her panties were sticking to her labia. I bent down and started kissing her over her panties. She let out another soft moan and grabbed my hair. I moved her panties aside with one hand and started licking her pussy. With my other hand I started stimulating her clitoris. Within seconds, she was orgasming. She started ejaculating and I sucked it all up -- it tasted sweet.

I move back up and kissed her -- mixing the taste of my cum with her ejaculate. We lay there kissing in each other's arms for a long time, totally spent.

It was turning dark outside by this time. I stood up and started removing her clothes. But she stopped me from removing the panties. She told me she wanted me to wear her panties under the boy clothes.

Obeying her command, I quickly put on my now dry pants over her panties and put on my t-shirt. She helped me remove the braid. It made me a bit sad to see my hair back to my usual style.

I returned back to the boy's hostel. Aayush, Pranav and Neel were waiting for me. By my dishevelled look, they could clearly guess that I had got lucky.

I gave them a smirk and went to my room. They pestered me to come up with details. I was blushing by now, but managed to say, 'A gentleman never tells.'

After some time, they finally gave up and went back to their own rooms. Once they left, I locked the door and stripped down to my panties. I went to sleep wearing only Saloni's panties, totally blissful.

* * *

After that, Saloni started dressing me over the weekends. Of course we did it in the privacy of her room. The other guys just assumed, we were dating now and I was getting some action over the weekend.

We didn't repeat our previous episode of oral sex every time we were alone, but whenever one of us was feeling horny, we put ever thing aside to please the other.

Saloni soon started teaching me more about being a girl. She taught me how to apply makeup and all the nitty-gritties of it -- applying the foundation evenly, curling my eyelashes, using a plastic spoon to apply a thick mascara without smearing it, how to apply eyeliner to make my eyes look bigger, selecting the right tone of blush and highlights to go with my skin and clothes, using a clear lip gloss over the lipstick to make my lips look fuller.

She also taught me how to maintain my arms and legs after shaving to make them smooth and shiny. She taught me how to walk in high heels delicately, to tone my legs and enhance my posture.

Whenever we were alone together, we talked a lot -- from clothes to gossip, we never ran out of things to talk about. We even discussed boys occasionally, but whenever it came up, I was too embarrassed to talk for long.

While she was teaching me to be a girl, I started teaching her how to please a boy. I might be turning into a girl, but I still had the equipment of a guy. I showed her how to use her tongue and lips imaginatively to slowly lick and suck a cock while intermittently stroking it, how to pay attention to his balls and always maintaining eye contact. I had a small penis, barely 4 inches. With very little difficulty, she could deep throat me. I guessed she'd have to learn to truly deep throat when she confronted a real man's cock.

On Saloni's insistence, gradually I also started wearing lingerie under my boy's clothes to college. Initially I wore only panties, but soon I was also wearing lacy slips under my t-shirts. On a dare from her, I also once wore one of her bras to college under a baggy t-shirt. But I was so self-conscious and nervous the whole day, I didn't repeat it. Wearing panties and slips under my clothes became a regular thing and my boy's underwear went mostly unused. She also started taking me shopping whenever we had money and time to spare. And thus I started building my own girl's wardrobe.

* * *

Soon the mid semester exams were coming. We were all busy studying.

The five of us were sitting in Aayush's room one day studying when Saloni said, 'So who do you think is going to score the highest marks among us.'

I was a geek and I was pretty confident, 'I, of course. I'll beat you guys any day.'

Aayush, Pranav and Neel didn't even bother pitching in. They knew Saloni and I were the best at studies.

Soon we were in a heated argument and I said, 'I am ready to bet you I will score better than you Saloni.'

She rose up to the challenge, 'Fine. I'll bet you too.'

Now, this was an opportunity to embarrass Saloni and I was all for it. I said, 'OK, if I win, you have to be the housemaid for the four of us for a month -- you'll have to do all the washing and cleaning for us.

This perked up the guys. And they chimed in and started goading her.

She was silent for a long time, but finally she said. 'OK, but if I win, you have to dress up completely as a girl, in a saree for the whole day. And I mean the whole time, even in class.'

At first I was cautious. What if she won? But the other guys started egging me on too.

Soon my over confidence ruled over any sense of caution and I agreed to the bet.

* * *

The exams started and they went pretty well for me. I was very confident of my win.

But so was Saloni. I was getting nervous about the results now. Who was going to win the bet?

To be continued...


piyali19
piyali19
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AnonymousAnonymousover 3 years ago

just a perfect story.....i too am a boy but i do enjoy fitting in girl's clothes....

and the indian backgroung makes it just so perfect and real....love it

Suze29Suze29about 4 years ago
Wow- Add more on braids and other indian clothing

Just wow. You are amazing. Please write more on braids and bindis and dressing up in lehengas and for occasions such as Diwali.

Thank you so much. Can't wait to see more.

BrendaNWBrendaNWabout 4 years ago
Wonderful

Thank you, loving your story please continue. You are a very talented writer and I experienced every moment as they lived it. TG Tiffany

AnonymousAnonymousabout 4 years ago

Pls go on! Its so hot! A bit more details would be even btr, especially about the saree and the situation. And the first time a man wears a full saree is always so speical, esp if he does it for real and for his girl

AnonymousAnonymousabout 4 years ago
Amazing! I love this Indian fantasy!

U make me want to wear a saree and be a girl. I love this story please continue this story and many more Indian tradition stories.

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