Khan Market Sissy

An English degree was all that Lijo had when he took a train from Kochi to New Delhi. He was promised a teaching assistant's job at a University in Delhi. Though he knew that he could barely survive on the salary of a mere 16,000 rupees, Lijo still went ahead as he somehow wanted to leave behind his conservative hometown in Kerala and experience a metro life.

Lijo was fair with a tinge duskiness, quite tall at 5.8 feet. However, he was just above 50 kilos, lean with long legs and a curvy hip. Lijo has been admiring his own feminine figure ever since his late teenage. He would stand in front of a mirror for hours, simply admiring his own structure. He had (hair) fringes that reached till his lips, which he neatly kept to the back of his head, as a camouflage, whenever he was not enjoying his femininity by letting it fall on to his face.

Everyone thought he was straight as he used to ogle at all well dressed women, but only he knew that he was checking out what they were wearing, all the while imagining how would that dress look on himself. However, apart from tying bathroom towels above his nipples, he never tried on any feminine cloths, thanks to the joint family that he was raised in.

It was then the job offer from Delhi came and Lijo didn't have to think twice before accepting.

He took a small dingy room for rent in Laxmi Nagar, and started his Delhi dream. Though the salary was peanuts, the work schedule was quite comfortable for Lijo. He just had to put in four hours of academic work per day and he was free the rest of the day.

Lijo wore a pencil fit jeans and a black full sleeve t-shit for his first day at work. Things were pretty smooth and he managed to leave the university by noon. Being new to the town he decided to roam around a bit.

He went to Connaught Place first. From his home town where girls wear 'Sanskari' clothing to the city of Delhi where girls rocks thigh high shorts and micro-minis was a whole new experience for Lijo. As each girl walked by Lijo's craving to walk through the streets just like them got stronger.

That day, he returned home and jerked off to some rough porn. He wanted to be a man's bitch and he knew it. Lijo, then started to search for places where he could buy cheap women's clothing and came to know about the famous Sarojini Market.

He decided to pay the place a visit.

As he reached Sarojini, the next day morning, girls had already started their shopping spree. Skimpy tops and skirts that barely covers anything were getting sold off like hot cakes. There was one thing similar in the eyes of the chicks and of Lijo, the sparkle in their eyes when they see a slutty outfit.

A lemon yellow short skirt, a white tank top, a black tube dress that begins from above the chest and ends on the bums, Lijo spent the entire pocket money he had in a matter of minutes. He however stayed for another two-three hours, just admiring the clothing. Only worry that he had was that he need to earn more to be able to buy more.

Lijo soon headed for home. He got a pair of red lingerie and a makeup kit on his way back. As he settled down his first stage of feminisation began.

He took out a hair removal cream and applied it all over his body. After a few minutes, he felt a strong sense of burning sensation all over. He however knew that the pain would soon turn into pleasure. He took out a spatula and scooped out the cream from over his skin and each scoop took out a chunk of masculinity from him. When he was done, he was flawless, a tall diva. His tiny dick, limp and red, looked like a rosy clitty.

As soon as he was done, he slipped on a pair of red panties. His clitty twitched as it came in contact with the satin panties. That was a moment of satisfaction for Lijo as a long cherished dream of owning a pair of panties finally came true. At that moment, he took a strong decision that he would never go back to boring men's inners and that it would always be panties for him.

He then roamed around the room in his panties for a while. Made some tea wearing nothing but the panties. He was careful to keep up a catwalk, ignoring the clitty between his legs, as he walked around. Soon, he positioned himself before the mirror and started his make up. He liked it to be simple.

He took out some dark red lipstick and carefully applied it. He joined his lips and smiled in satisfaction to the mirror, acknowledging his own aesthetic sense. Soon, he took out some fake eyelashes and carefully installed them. A dark blue eye shadow above the lids and thin black lining to the eye and his make up was done.

Later on, he squeezed in a pair of cushions into his red bra before slipping it on. Lijo was leaning his head forward as he tried to hook his bra by stretching his hands to his back. His fringes dropped on to his face as he did that. Soon, the hooks of the bra clasped with a noise and Lijo suddenly looked on to the mirror lifting his head up and flicking his hair back.

One look at the mirror and Lijo immediately knew that the noise of the bra clasping was actually the voice of his fate getting sealed. The girl in the red lingerie is what lays ahead for him, not the life of the boring boy.

He slipped on the black tube top over the lingerie and wore the tallest high heels he could afford. The high heels were also black. And the mirror showed a sexy party girl. The boy was nowhere to be seen.

Even as his desire of dressing up finally came true, two things remained a problem. One, the lack of money to buy anymore clothes, two, the lack of a man who would appreciate him as a girl.

.....

Days passed by, Lijo continued his dressing up adventure in his room. Apart from the four hours of work, Lijo was mostly in one dress or the other most of the time. Each time he found out a new fact about him, like the white tank top enhances of the beauty of his square shoulders or the yellow minis gives his ass a sexy appeal etc. However, he craved for more dresses and of course a master, a daddie, an owner.

One weekend, even though he was out of cash, Lijo went to Sarojini. At least he could look at clothes, he thought.

Lijo was going through a section of skirts. Wrap arounds, micros, one with frills, denim shorts...he skimmed through the pile of clothes asking the shopkeeper about the prices in his broken Hindi, even as he had no plans of buying due to the dent in his pocket.

As he was going through the skirts, a couple came to the same stall. The girl in his late thirties, slightly on the heavy-side was accompanied by a sexy looking gentleman. Though they looked nothing like a couple with his incredible looks and the below average looking women, they acted like one. However, apart from holding her bags, the man seemed least interested in what his wife was planning to wear.

Lijo, ignored them and continued to look at skirts. He however, gawked at the handsome guy through the corner of his eyes. He was wearing a white round neck t-shirt. His biceps were quite bulky and it was evident that he was ripped underneath. He had a strong jawline and it was covered by a thick batch of dark black stubble. The beard look was really hot.

As he continued shopping, he realised that he wasn't the only one checking out people there. The man was also noticing Lijo going through the skirts. After seeing him looking at him a few times, Lijo got scared.

"He is quite hot but I don't know him," he thought. He moved on to a Tops' section a bit far. Soon, the man had left his wife and was standing in the counter next to the one where Lijo was, continuing to look at him. Often, their eyes met too.

"Oh what should I do, what should I do," he thought. Run, was the first instinct, but he thought, "What if he is nice? What if he is the master I have been waiting all along?," Lijo thought.

He mustered some courage, turned and looked at the stranger and gave a pretty smile at him. The man so the green flag going up and came closer. "Hey, found what you are looking for," the man asked.

Nervous, and shivering, Lijo said, "Hi, I am just window shopping," said Lijo.

"Oh, I thought you were looking for a dress for your girlfriend or someone. My bad. But why would a man window shop. You are not planning to wear any of it, are you," the man replied leaving Lijo startled for a second. The man, however, broke int a laugh. "Relax man! I was just kidding. I am Aryan, what is your good name, he asked. 'Lijo', the sissy replied.

I was too bored shopping with my wife and saw you raiding the shops alone, thought we could have a conversation on the sides, that's why I came to you, Aryan tried to explain. Lijo, nodded back, perfectly understanding that his intentions were different.

Lijo decided to be bold and said that he has no girlfriend. "I don't have a girlfriend, but I like girl's clothing," said Lijo. So you do wear them, Aryan said. "I kinda saw the panty under your jeans while you were at the skirt stall," Aryan added giving a naughty smile. Lijo blushed. Now sure that he has found his man Lijo asked, "But you are with your wife, here?"

"Well, that is a long story. My wife is a rich Marvadi and I married her for the money. I am never satisfied with her. She is not slutty at all. The skirts you were looking at were ten times more sexier than her choices. And you seems to have a body that can sport any outfit better than any woman," Aryan said. Lijo, just blushed a walked to the next stall.

Aryan just walked alongside Lijo for a while watching him go through the clothing. Lijo felt the presence of a man by the side very comforting and he hoped that he makes a move soon. And then it came. Aryan slowly placed his hand on Lijo's hip and caressed his butt. Lijo's smile was enough for Aryan to realise that he has met the perfect bitch.

"You want to go to that coffee shop with me," Aryan asked and walked towards it without waiting for a reply. Lijo followed like an obedient deer.

"So why are you not buying anything?" was the first obvious question from Aryan. Lijo told him his story and how broke he was. Aryan's eyes sparkled, he took out a credit card and gave it to Lijo along with his visiting card.

"Go to the closest mall and buy whatever you want. Once you are done call me in this number," Aryan told him. And you don't have to live in Laxmi Nagar anymore, Aryan said while handing him over a key and address to an apartment in Khan Market.

"That is your new home. You can quit your job, you're Aryan Khanna's girl from tonight," he said adding, "From today, you are not Lijo, You are Ruchica."

"Ruchica," Lijo said to himself and smiled. But how am I going to pay you back, Ruchica asked innocently. "I don't intend to keep you to myself and when I am down with you, both of us would only be richer. Just consider this as initial investment by daddie on his sissy," Aryan said and Ruchica nodded in agreement.

...

The calling bell rang, and it was Aryan at the door of the flat. Ruchica was wearng a silver silk top that has no shoulders and barely covered his clit. He was wearing a black panty underneath.

Aryan slapped across Ruchica's butt as he handed over his briefcase to him. So, how is my sissy liking her new life, Aryan asked. I am the happiest daddie, Ruchica said.

"So, tonight we will have a party. One of my friends would be joining us," Aryan said, making a Ruchica a bit nervous as even Aryan was yet to penetrate him.

"So, I have a gift for you," Aryan gave her a small box and inside it was a steel butt plug. "Bend over" Aryan commanded as he squirted lubricant onto the butt plug. He slid it inside Lijo as he screamed in pain. So, Lijo go be Ruchica and cook us dinner. Once you're done cooking your ass will be ready for the party, just make sure that your body too would be, he said.

Once he was done cooking, Ruchica took a nice bath in the tub. He came out and slid on a red short skirt with frills all around and a black lingerie underneath. She put on a black flashy corset on top, leaving her shoulders and top of her back bare. He tied his hair up leaving the fringes on his forehead. He wore a diamond necklace and put on the red lip stick and dark blue eye shadow. A designer stilettos that Aryan bought for him was the footwear. The legs were bare from his upper thighs till his angles. And the long legs plus the tall high heels made his legs sexy like a Bollywood actress.

.....

Raghav, Aryan's office friend arrived by 9 pm. He was in his forties. He had a salt and pepper look but was fit and athletic. As he walked in Ruchica served him a welcome drink.

"Hey, you said you have a sissy here. Why are you making a girl serve me," Raghav asked. It was Ruchica who replied to that. He grabbed Raghav's hand and guided it under his skirt to his pantie.

"Woah, this is one hell of a sissy. She looks like a south Indian actress," Raghav said as he sat on the couch and made Ruchica sit on his lap.

"So, Aryan treats you like a wife doesn't he?" Raghav asked. To which Ruchica nodded. "But I want a bitch, can you be my bitch?" he asked.

Ruchica' face brightened only to be made red by Raghav as he gave him a tight slap across his face, "What are you smiling at sissy?" Raghav asked as he grabbed him by the hair and pressed his face against his crotch. "You know what to do," Raghav's command came.

Lijo, opened up Raghav's belt buckle as his big cock snapped out. "It is so big," he inadvertently blurted out. A slap followed. "Did I ask you how big it is, shut up and open your mouth," Raghav said.

Aryan, who had gone for a bath returned to hear nothing but the sound of Ruchica gagging on Raghav's meat. "Hey, what are you doing to my sissy," Aryan asked. "She likes two cocks in her mouth, not one," he said as he pocked Lijo's face with his cock, laughing.

Ruchica started to switch between the two cocks and gagged on both of them for a while. Later, Raghav made him lay on his stomach across his lap and started to spank his ass as he kept on sucking Aryan.

He then lifted her skirt, ripped open her pantie and slowly started to pull out the plug. "You want some meat in there don't you sissy," he asked. 'Yessss,' Lijo muttered in between the gagging. He pushed it hard in with no lubes and not caring to ease it in. Ruchica screamed in pain only to say "Yes, Yes, Yes" later as he pushed his member inside him. Ruchica came, like a girl and his tiny cock became further limp.

Now, it was Aryan's turn. He took off Lijo's skirt and now he is only wearing his black corset and the high heels. Aryan made Lijo ride him. His clitty, now limp, started to dangle up and down.

He carried him by the waist and made him lock his legs around his waist, then fucked him in the air. He soon came inside his hole and threw him on to the sofa where Raghav was waiting. He fucked Lijo doggy style while Aryan milked his limp cock like milking a cow, slapping his balls in the process. Each slap on the balls made the sissy scream in pain and pleasure.

Hearing it Raghav, became further horny and increased his pace. His cock started to hit Ruchica's intestines. Soon, he was ready to blast. He shot cum all over Lijo's eyes, face and body.

"She is perfect for our office party," Raghav said as he collapsed on top of the sissy. He shared a cigarette with Aryan before writing a check and soon left.

Lijo, now Ruchica, laid on the couch, exhausted and covered in cum as his master made plans to take her out in public soon.

To be continued.