My Guilt and My Pleasure

On the 2nd of June 2020, I came back from my university due to the implementation of lockdown in my state. I, Arin,  was alone here at my house and had no friends to socialize with. Life was way too boring than I had imagined. But something sparked in me, a strange feeling towards my own body.

I wanted to wear girls’ clothes since they look so elegant and sexy. So, one day when my mum wasn’t around the house, I opened her drawer and tried some clothes that belonged to her. I felt so girly, and it was the best feeling I had experienced.

Weeks went by as I dressed up, put some makeup on, and took selfies. My crossdressing was a secret I couldn’t share with anyone out of fear of shame. No one knew I even did these things.

Everything was going well until August came. I had received a notice from my university that I should take my semester results. So I booked a train to Birbhum. So, I traveled from Darjeeling to Birbhum. I had to rent a room since the hostel had been closed.

I also managed to sneak up some clothes from my mum, and I wore them. The people of that place hardly knew who I was. It was fun dressing up and roaming around the place there during the night.

On the second night there, I wore some makeup. I didn’t need any wig since I have a pixie cut that’d look similar to a girl’s hairstyle. I even wore black pointed heels and a tight leather legging that belonged to my sister. I was scared that they might find out there without clothes and makeup.

But fortunately, they had gone to visit our relatives. That leather legging was tight as hell. Still, I managed to wear them and then I went outside. It was 11:00 pm, and there were no people around the streets. I roamed around the silent street with no fear until I met some boys around the corner.

These men were nasty-looking, with leather jackets and husky voices. They were all smoking and laughing there. I felt so scared, but I tried to walk as feminine as possible. One guy whistled at me and said, “Where are you going, boy?”

I had shivers down my spine. They knew I was a boy trying to mimic a girl. They got off their bike and came close to me. The quirky guy introduced himself first. His name was Bhavan, there was a fat guy named Bidhan, and the big muscular guy with a leather jacket said his name was Tapan.

The scariest part was that they were from another department and were my seniors. Bhavan tried to blackmail me, saying, “Should I inform the department head what you’re doing?” I nearly cried. I started to regret all my decisions about this whole damn thing.

But Bidhan grabbed my butt and said we could arrange something. It felt so strange being scared to shit and being horny at the same time. I asked what I could do to keep their mouth shut. And he grinningly replied, “What a wannabe slut like you should do.”

Tapan was quiet the whole time and was staring menacingly at my heels. Bidhan was busy pinching my butt, and Bhavan called his roommates, saying he’ll be late tonight. They were all staying in rent. Since there were no housekeepers there, I knew it would happen.

I cried and begged them to leave me, but they wouldn’t listen. They grabbed my hand and ordered me to sit on their bike, and I complied.

There were two bikes, and I sat on Tapan’s bike. But shockingly, Bhavan sat behind me. He said, “Just to make sure this whore doesn’t fall off the bike.” Then we rode off to their room.

The whole place was dark, and the street lights were broken. Bhavan, who sat behind me, grabbed my throat from the back, kissed me, and licked my cheeks. I prayed this whole thing to be over, but sadly we reached their place.

The whole place was huge. Several students had been living there. But the place was like a deserted camp since hardly any students had come since the lockdown. There was no sign of any housekeeper, and even if there was, what could I say to them.

Tapan parked his bike, and we went inside the room. I have to tell you. It was a mess. The whole place smelled like a public toilet. Their dishes were not done, and bedsheets were all dirty, and I could go on. Tapan locked the door and said that he and his friends would teach me a lesson.

I was scared that they were going to beat me up or something. But they grabbed me and pulled off my pants. Suddenly, I cum, and I was shaking with orgasm. They laughed at me and said how desperate I was. I felt so guilty yet so horny, and then they pulled my jacket and said to keep the heels on.

These men were shocked to see my ass, Bhavan immediately sank his face deep in my butt and smelled It, and he gasped, “This right here is a virgin, my friends.” Tapan started to talk more and was even more excited than Bhavan. Bidhan pulled his cock and started to spit on it and rub it.

He pulled me to his lap and thrust his cock right into my hole. It felt so painful. He was adamant about putting to down like a bitch. After some time, he pushed me from his lap and said that he’d be right back.

Tapan undressed and put his brown underwear in my mouth. It smelled so bad I nearly puked. He said, “That’s to shut your loudmouth.” Bhavan came from the toilet. He grabbed my throat and put his cock right in my mouth. He said, “Nepali bitches like you need to be put down for good.”

He kept throbbing his cock in my mouth until I gave up and embraced it. I had to since there was nothing I could do. I even felt a bit satisfied that they were attracted to me, even if it was to bone me.

After an intense deep throat, I was laid on the bed with my face upwards. Tapan started to do the same thing to me. I nearly passed out but managed to bear it. After he had finished, he lighted up a smoke. I was lying on the bed with my makeup ruined and eyes red with my tears and then cum all over my face.

Bidhan came back, but I noticed a bottle of hair oil with him. He pulled my ass upwards and started to pour that damn oil, and then he placed his feet on my head and started to fuck me in a doggy-style position. I couldn’t even scream. I was shaking too much, and my words were all breaking up.

I tried to shout, “P-L-E-A-S-E- S-T-O-P.” But he went on fucking me till my eyes rolled back. Tapan pushed him and put his cock inside, saying it was his turn to wreck me. He was so horny he didn’t even last a minute. He unloaded a shit ton of cum inside my butthole.

To be fair, even I was starting to enjoy this. And with and weak voice, I uttered, “Is that all you’ve got.” This made them angry, and then both Tapan and Bidhan put their cock in me and started fucking me. They even carried me around the room while fucking me.

After they were done, Bhavan said he wanted to make a video of me farting the cum out. So, after they unloaded again, I farted out the cum. They laughed at me, saying a big ass volcano just erupted.

Before I could clean up, though, they ordered me to jerk off in front of them, and I did. But they grabbed my neck and placed my face down, making me lick the cum off the floor. I did, and I was given their permission to clean myself up.

The whole fuck fest lasted till 3:00 am. I was so tired and wanted to sleep. Tapan dropped me off in my room. Since my clothes were ruined, I had to ride on his bike with my heels on and nothing else.

Thankfully he took me to my room via shortcut, and before dropping me off, he said, “We know where you live bitch. Next time wear some proper makeup.” I didn’t pay attention to his words since I was half-dead due to exhaustion. So, I went in and slept without cleaning myself properly.

The next day was an ordeal, a ton of clothes to wash, and the boys even visited my room. They introduced themselves to my housekeeper as my department seniors and were here to help me with some things. And I couldn’t even utter a word, but I started to develop a feeling towards them.

I felt so cozy around them even though they boned me last night. I felt like a wife with many husbands. It was there that I developed a liking for men. After I returned home, I kind of missed them. Now they have graduated from the university, but we’re still in contact with each other.

Tapan lives in Kolkata, and I’ll be visiting them this month. Now I have a set of wigs, glasses, eyelashes and nail polishes that I can wear and adorn myself with. I even secretly bought a leather skirt. I can’t wait to see them after such a long time.

My journey is just beginning as to how I became a sexy crossdresser to developing feelings for men like them. The next time I write something, I’ll be writing about them again.

I hope you stayed this long here to read my story and enjoyed it.

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