A Crossdresser’s Life

Hi! This is my first story on ISS so don’t be harsh on me. This isn’t a real story, but a fantasy which i am going to share with you,though the characters are real. I am a boy(21)(crossdresser) doing my engineering in Bangalore in a reputed college. I stay at one of my fathers friends house, his name is Rajesh. His first wife died due to cancer so he married again. His new wifes name is Rajni. Rajni, in her 30s, is a damn hot woman with a plus size figure. Now lets move on to story…

Initially i use to wear my sisters dresses or my mothers bra,panties,saree,blouse,petticoat and see myself in a mirror and admire myself. Though i wasnt so good at makeup, i used to apply lipstick and put some jewellery items. It couldnt make me look like a girl but the feel of women’s clothes turned me on. And then i used to masturbate after my every crossdressing session, thinking about being fucked by a guy. But then as i grew up chances of being alone became less and i had to kill my desire of dressing as a woman.

I got enrolled in college, moved into Rajeshs house. Rajesh and his wife were good with me. I too was enjoying life as a boy, flirting with Rajni. One day while i was taking bath, i saw Rajnis clothes in the bathroom. The moment i saw them all of a sudden i got an urge to try those clothes. I took her panty and pressed against my nose. Oh, god! her cunts smell was so good that my precum started to ooze out of my cock. I put on her bra and panty and started to masturbate. The touch of her undergarments made the pleasure intense and i came heavily. Then i removed her undergarments and washed myself. From then on started stealing her clothes and wear them in room at night. Now my old desires were coming true and i started exploring myself as woman. I started wearing panties wherever i went, even to college.

One night i got a desire to dress as a girl and go outside. I went to Rajnis room and checked whether she’s asleep. She was deep in her sleep and uncle had gone to a business trip for 3 days, so i decided to do it. Since i used to wear panties every time so i just slipped into a nighty. It was a pink nighty. The panty was a yellow one. I slowly stepped outside the house and went to the terrace. The cold breeze sent a shiver through my body. I felt so happy that i starting rotating like girls. As i was rotating i saw someone standing at some distance, i got scared. My heart started pounding furiously. Then that person started moving towards me, i turned my face away.

Then i heard a voice “Ahan is that you?”. It was Rajni! I could tell with her voice.

I said to myself “Oh, God! What have i done”. I was so embarresed.

“Ahan turn your face towards me, I want to talk” she said.

I slowly turned towards her. As i did she suddenly burst into a laugh.

I said “Sorry aunty”

She controlled herself and said “First come into house, we’ll talk there”

We both went into house. She sat on the sofa and i started going into my room.

“Where are you going?” she said.

I stopped and said” To room”.

“come and sit beside me, we need to talk” she said.

“So thats were my dresses are going!” Rajni said.

I said “Sorry aunty but please dont tell to anyone”.

“Ok i wont tell to anyone and i’ll even help you with your feelings but……”

“But what aunty” I said.

“You ahve to do something for me” She said.

“I am ready to do anything you tell” I replied.

“Anything?” she said.

“Anything aunty” I said.

She started leaning towards me and planted a kiss on my lips. I felt a rush through my veins. We both saw into each others eyes. Her eyes were full of lust . I couldnt resist and started kissing her furiously, biting her lips, licking her tongue, for may be five minutes. The kiss was full of passion. Then i mad her sleep on sofa and removed her panty. She had shaved her pussy. I started to lick her pussy like a dog. She was moaning with pleasure. I kept on licking her and then let a shiver and spurted all her cum on my face.

The taste of the cum made me go crazy and i started kissing her again. This time even harder. As we kissed i moved my one hand to her breast and starting pressing them. She pulled my away and started to remove my nighty. She saw that i was wearing her panty and gave me a naughty smile.

“Aunty ke kapde pehen na pasand hai tujhe?” She said. “Haan aunty aap in kapdo me bohut hot lagti ho. Mai bhi aap jaisa lagna chahta hoon” I said. And then she pulled my panty down and started stroking my cock with her hand. It felt so good, “Aunty moo me lijiye mere land ko” I said.

She started licking my dick. I was getting harder and harder. Then i filled her mouth with my cum. She took all the cum in her mouth and drank it. Now i couldnt control and wanted to fuck her badly. “Aunty mai apko chodna chahta hoon” I said.

She removed her nighty and was completely naked in front of me. Her huge boobs, tummy, big ass made me crazy and i agein started kissing her. after kissing i moved to her boobs and started sucking them. “Haan choos mere chuchiya, zor se choos, Hai ma” She started moaning. While i was busy sucking her tits she took my dick and guided into her pussy.

I started fucking her pusssy. “Ui ma! aaaaahhhhh! Chod aur zor se chod. Phad daal meri choot” She said. Her words made me crazy and started fucking her furiously. I fucked her for atleast 15 minutes. “Aunty mai jhadne wala hoon” I said. “To jhad ja meri choot me, Banade mujhe maa” she said. I came in her pussy and filled her womb with it. Then i collapsed on her and fell into sleep. We both got up after two hours and had another fucking sexion in bedroom.

Then again we fell asleep. I got up at 8 am. She was still sleeping exhausted from our fucking session. Now i was getting ready for her questions about my crossdressing. I was happy that finally someone knows my secret and is ready to help. If you people like my story then the next part is coming soon. Please comment.