Sad life of a crossdresser - Karan's Journey

Karan looks very fair and handsome. But people never saw him as a real man. He has many feminine qualities. Since he had lost his father when he was born, he was brought up by his mother. He had two elder sisters and they pampered him like anything. He did not feel anything weird in his body until he reached the age of eighteen. So, he did not like to talk to any girls in his school or in the college. He felt attracted towards the men. When he was very young, he had seen his elder sisters checking out men.

So, he had heard them saying some hot comment about those men. Slowly, he felt attracted towards men rather than the women. Even when his classmates showed him a porn while in the hostel, he did not show any interest in that. But he felt something weird when he saw the men with big dicks in the same porn. But his mother had taught him that homosexuality is a sin. So, he tried a lot to control his feelings. In spite of that, the constant bully in his school, colleges and now in the workplace, made him frustrated.

He badly wanted to leave that place for good and settle in a different place. He just wanted to forget everything happened in his life so far. So, he resigned his job and told his mother that he wanted to stay alone in a place. He then went to Bangalore. But he did not tell anything to his mother.

After reaching Bangalore, he booked a room in a hotel. From there, he started to search for a home to stay. He wanted a job to take care of his living. But even when he walked towards his room, he noticed the hotel staffs making fun of his ass swinging. He sat on the bed and started to cry. People might be different now but they were treating him the same. So, he had to change that once and for all. He went to the shopping mall and bought all the women clothes he fancied. Then, he checked out from the hotel and went to another hotel.

But before checking in, he just covered his face with the cloth and pretended as if he had a dust allergy. He could talk exactly like a girl. Since his body language looked like a girl, the receptionist took him for one. Then, he entered all the fake details citing that he had lost all the ID and address proof. So, he bribed the hotel staff to let him stay there. As soon as he came to the room, he locked the door. Then, he rushed to the washroom and removed all his clothes. He stood there naked looking at him. He had a very small penis and had no hair in any part of his body except on his head and around his dick.

Soon, he applied foam all around the dick and removed each and every pubic hair he had. Since he looked very slim, he wore a thong and his ass cheeks came out from the opening. They really looked like a woman’s. Since he had some manly boobs, he wore a push-up bra which made him look like a woman with tight and big ass. Then, he wore a one-piece dress showing his cleavage and extended until his inner thighs. So, the dress covered just his panty and a few centimetres below it. Karan wore red-coloured high heels and sat on the stool in the bedroom. He already had a long hair and he combed it nicely to make it look like a women’s hairstyle. So, when he finished the makeover, lipstick, Kajal and the cream, he stood opposite to the mirror.

He looked better than most of the models today. His thighs and the legs looked very much toned and shiny in the light. He had applied some cream on his limbs for that. Then, he came out of the room swaying his ass. When he came to the corridor, he saw men looking at his ass. Slowly, she came to the reception and handed over the key. The receptionist looked at Karan with a jealousy in her eyes. The male staff next to her looked at him with the lust. He could not takes his eyes off his ass while walking. On the next day, he saw an ad for the job opening in Bangalore. He went to the company with the fabricated resume and other ID proofs. It was a BPO company. Karan waited in the hall where the other candidates waited for their turn. The girls looked at him and lost their hope that they would bag the job. The guys looked at him and wished they should get the job so that they could have a good time with this chick. When Karan went inside the room for the interview, the manager looked at him from the head to toe.

 

Throughout the interview, he did not have any doubt that he might be a man or a cross-dresser.

After the interview,

Manager: Any questions?

Karan: No sir.

Manager: Can I ask you something personal? I just wanted to see how bad you wanted this job.

Karan: Sure sir.

Manager: Do you compromise on the job?

Karan: Sure.

He did not even think twice. Soon, the manager locked the room and removed his pants. Karan just kept his legs crossed showing his inner thighs. When the manager came closer to him, he removed the legs and smiled at his manager. Then, he grabbed his crotch and pulled him towards him holding his dick. Soon, he took it deep into his mouth and started to suck it. The manager closed his eyes and still, he could not believe that he was indeed having a nice blowjob from a hot chick.

 

Karan looked exactly like a hot chick in the office during the interview. Since he wore a short dress, he crossed his legs to expose more of his thighs. His manager had no idea that a sexy cross dresser was sitting in front of him. During the interview, he kept starring at Karan’s thighs. He introduced himself as Kareena. The voice perfectly suited him and the manager had all the reasons to hire that hot babe. Finally, he expressed his interest in having sex with her indirectly.

When he asked Karan, he kind a felt turned on. He wanted to try him once. His first gay sex. So, he agreed without thinking twice. When he walked towards him locking the doors and windows, Karan kept smiling at him. Then, he grabbed his pants and pulled him towards him. He unzipped his pants and took his long dick outside. Soon, he took it into his mouth and started to suck it. He could not believe that he was sucking a man’s penis for the first time in his life. So, he felt the pleasure of a gay for the first time.

His manager, on the other hand, could not believe that a hot chick was sucking his penis. He just grabbed Karan’s cheeks and closed his eyes to feel the pleasure. Slowly, Karan increased the speed of the blowjob. His saliva formed as a lubricant and hence the sound of sucking became very much audible. He stopped Karan and asked him to stand. Then, he pushed him towards the wall and removed his dress. Karan stood in a bra and panty in front of him. Since he had a micropenis, his manager did not notice a thing in his panties.

Soon, he turned her around and spanked the sexy ass cheeks. Before he could take off the panties completely, Karan removed the thong a bit until he could see the ass hole. Then, he bent a lot and spread his legs to allow his dick inside.

 
When he first patted his ass with his dick head, a strong moaning voice came from Karan. But when he tried to insert, he found it very difficult. He was indeed a virgin. So, he tried very hard and finally pushed it deep into his butt. Karan had never experienced that kind of a pain in his life. But he controlled and let him have his fun. He, of course, had his own fun as well. After fucking him for a while, he asked Karan to turn around. But if he wanted to fuck his front, he would come to know about his true identity.

So, he just said, “Sir. Not today. You can take me to your guest house after me joining”.

The manager looked impressed and both wore their clothes. When people saw Karan walking with his legs spread, they understood what might have happened inside the room.

 

As everyone might have expected, Karan received the call letter and he joined on the next day. He came to the office wearing a short formal skirt and a formal shirt. He had the slit at the back extending slightly below the panties. So, when he walks, the men could figure out his hot ass from behind. When he works in his cubical, men would come to his place and talks to her for no reason. They just wanted to see the athletic and toned legs.

Even Karan would show something more by spreading his legs and providing the access to view his panties. Some guys would take him to the dinner after the office hours while some would buy him some expensive things from the mall. One of her colleagues took him to a swimming pool one day. When he wore a bikini, he looked stunning and better than most of the bikini models. Many guys just stared at him and some even went underwater to check him out.

Even while traveling on the bus, some guys would grip him and place their hands on his thighs. All those things just made him horny. He realized that he had become a complete gay after those incidents. Once, his boss took him to the guest house. He knew that Karan would look gorgeous in the swimsuit. So, he asked her to change to bikini and both entered the swimming pool. There were none except the both of them.

Slowly, he pushed Karan towards the wall inside the pool and started to smooch him. While kissing, Karan placed his hands over the underwear and inserted suddenly. Meanwhile, his boss started to press his breasts. He could not control when Karan started to stroke his penis. After a while, he tried to remove his panty. But Karan stopped him and took him to the bedroom. He concentrated more on the foreplay and made him tired. So, after sucking his breasts, he felt very much sleep.

 
He soon started sleeping and Karan felt totally relieved. But he escaped only on that particular day. Someday, he will be caught. He kept thinking what he could do to stay safe. He felt confused. None in this whole world would offer a job with good salary for no work involved. Karan should just let his manager kiss him whenever he wanted and make him bang his butt. He would pay him very good for that and he need not do any work. So, he did not want to lose this job. Telling him the truth might blow this thing.

When he saw his boss sleeping, he saw his dick still hard. So, he took off his clothes and removed his boss’ underwear. He took it in his hands and started to suck it. Then, he placed his dick head touching his boss’ and played with them both. Even he felt aroused while sleeping. Finally, he guided his boss’ dick into her ass and started to ride him nicely. Finally, his boss came inside his ass. When he woke up, Karan had already left. Then, he called his boss and told the entire thing. He also blackmailed that he had shot the whole gay sex thing happened in the bedroom. So, if he wanted that to be a secret, he should keep him in the job and pay him good for the same kind of work he had done before. He agreed and still has the gay sex with him rarely.