From Straight to Sissy: A Journey of Self-Discovery – Part 5

Hello everyone, this is part 5 of the story. Please check out parts 1 to 4 for a better understanding.

My parents were out of town. Mahesh and Santosh made sure to use this time to fuck my asshole regularly. But then Santosh had to go back to his hometown. My parents were still two days away from coming back, leaving just Mahesh and me at home.

When Santosh left, it was just Mahesh and me at home for two days. My parents were still out of town. I was feeling very open and comfortable being a sissy.

I was only wearing a crop top and panties. Mahesh looked at me and asked, “Kritika, do you like the idea of older guys? Does it excite you?”

I felt brave and said, “Yes, I am okay with it. I like the idea of different experiences.”

Mahesh smiled. “Then, my sweet Kritika, I promise you lots of new feelings. Your mouth and ass will get many cocks.” He told me to give him a blowjob.

I pulled down his pants and boxers. His cock was hard and already had pre-cum on it. I got on my knees and started to suck him. The pre-cum was sticky on my lips when I pulled away. I licked his balls and the head of his cock like candy. I took him fully into my mouth.

Mahesh loved it. I sucked him for 15 minutes until he came in my mouth. The cum was thick, and I swallowed all of it.

Mahesh told me, “Kritika, if you want to meet other guys, go for it. Many men want to fuck sissies like you.” I told him I had tried gay apps but did not find anyone good.

He laughed softly. “A sissy just wants cocks. Do not waste your young, soft body. Let men use you. You will not be this age again, so enjoy it fully.” His words made me think about enjoying life to the fullest.

When my parents came home and I got busy with college, we did not have sex as often. We still had quick blowjobs, but dressing up and getting fucked was hard. Mahesh wanted me more and more.

One day, I really wanted to dress up and be fucked by him. I skipped class when my parents left for work and went to his room. He gave me a lace bra, panties and a short one-piece dress.

I shaved my body, put on makeup and wore my wig and the cute outfit. I went to the living room.

Mahesh hugged me tightly. He looked at me with love and said, “My beautiful Kritika, I want to destroy your ass today completely.” I said, “I missed you, Mahesh. Fuck me and destroy my asshole.”

He took me to his room and made me sit on the bed. He took pictures of me, telling me to pose cute.

Then, he started kissing me. It was very romantic because it was raining heavily outside. We kissed deeply for about 25 minutes to 30 minutes. He started undressing me until I was only in my bra and panties.

I took off his shirt, pants and boxers. His cock was hard and wet with pre-cum. He grabbed my body, my soft thighs and spanked my ass.

I got on top of him. I sucked his nipples, bit his thighs and took his cock into my mouth. He told me that I was the best at sucking his cock, even better than other girls and sissies. I felt happy and I thanked the sissy training videos I watched, but nothing beat the real experience.

After about 10 minutes, he told me he wanted to fuck me. He took off my bra and panties, put gel on me and started to push his cock into my hole in doggy style. When his cock went in, it felt amazing, like true heaven.

He took me to the mirror and fucked me from behind. He told me to look in the mirror and see how happy I looked with his cock inside me. He started fucking me very hard. I moaned like a bitch.

He made me bend over completely and fucked me until my legs shook. I could not hold the position. He moved me to the edge of the bed and kept fucking me doggy style, pulling his cock out and pushing it back in fast for two minutes.

He stretched my ass open with his hands. I felt my asshole wide open. He spat saliva into it.

Then, he fucked me in missionary position. I had a sissy orgasm, and my cock leaked cum. After some time, Mahesh also came into my mouth, and I swallowed it all.

We lay naked in bed. Mahesh told me he wanted to see me have sex with another sissy. I was excited. He said he got turned on when I kissed Shreya. I told him we had fun in the shower, too.

Mahesh said he would ask Kishore if Shreya could come over for a day. We decided we could not do it at home because of my parents and my classes. I suggested we book a hotel for Saturday.

We would tell my parents we were going shopping and to the movies. We would check in at 2 PM and be back before they got home at 7 PM. Mahesh agreed and told me to check with Kishore.

Mahesh called Kishore, and Kishore agreed to let Shreya come. But in return, Kishore wanted a day with me. Mahesh agreed. He told me, “Kritika, you need to go with Kishore one day.” I said Ok.

I was very excited to spend time with Shreya. The thought of being with her again, just the two of us, made my heart beat faster. I remembered our kisses and the fun we had in the shower. It was a new kind of excitement, different from what I felt with Mahesh, but just as strong.

And then there was Mahesh, who would be with us. He would watch us, and that made it even more thrilling. He had told me before how much it turned him on to see me and Shreya together. Knowing he would be there, enjoying our fun right along with us, added a whole new layer of excitement to the plan.

The days leading up to Saturday felt very long. I kept thinking about our plan: a hotel, just us, no parents, no classes. It felt so grown-up and daring. I wondered what it would be like, what we would do, with Mahesh also there, watching and being a part of it.

My mind was full of happy thoughts about our time together. I could not wait for the weekend to arrive, finally. This is just the beginning of our secret adventure.