Young secret cross-dresser’s 1st experience

Hello everyone. I am  Anuradha / Sameera, a Secret Crossdresser of 29 years old from Telangana. My breast might be around 34-36 as 36 size too fits well. I love sports bras and padded bras.

My sissy discovery started in my junior college days when my friend became my boyfriend. It started with him sitting beside me. We used to stroke each other’s cocks secretly under the bench. The handjobs slowly turned into blowjobs.

I also had my boobs squeezed by a few others in the class. But I was too scared to tell my orientation. I didn’t want to be seen with suspicious eyes. Also, this was going on as a fantasy only.

So our sucking and stroking continued as the class kept on. Whenever he was in the mood, he used to jump and sit beside me. Whenever he did that, I knew what to expect. Even I keep waiting for him to come.

After he came, we would try to cover the top with books, bags etc. Then slowly play around with each other’s thighs in our hands. Then open the zip and sneak our hands in.

During the blowjob, we would act as if something had fallen. As we went below to table to pick it up and, in the meantime, would have a blowjob done. It was awesome not only because of obvious reasons but also because it felt like an adventure. We had to make sure we did not get caught.

He was talking about his crush as I gave him a handjob. I thought this was an opportunity. I made the bold move and told him that I liked his cock. He could fuck my asshole if he had no problem with it.

I wanted to take it to the next level by playing the role of the submissive partner. (Though I am versatile ). But on the promise that it will not be leaked in college. He was shocked at first but became ready for it.

He told me he would buy all the cross-dressing stuff for me. He likes to fuck me like a cross-dresser Transgender. I didn’t understand. So he showed me Trans videos, and I liked them. It took some time for me to prepare mentally for it as I had never had any form of sex.

So one fine day, after planning it, he called me to his room. He gave me the bra, barbie doll outfit, panty and wig. He told me he would wait outside till I got ready. It took me quite some time to understand how to wear the wig, but somehow I got it through.

Once I was ready, I didn’t know why. I felt awesome and called him in. He was astonished and started to praise me. I really felt so feminine in the clothes. I couldn’t take my eyes off the mirror when I was getting ready. I was getting arousal looking at myself.

He slowly pulled me towards him and looked into his eyes. For once, he couldn’t believe it was me. We started kissing each other hard. He also grabbed my ass with his hands and squeezed them as I held his head.

Later he kissed my neck and cleavage as he lifted my outfit and removed it. I, too, removed his shirt and pant. We were half nude now as I started to explore his body.

He made me go down and feel his cock as I kissed his chest. It seemed bigger than usual, probably more aroused. I bit his cock from his underwear to tease him slightly before removing it.

I was giving it a few hand strokes before kissing the tip. I pulled the foreskin and locked it like a lollipop. He was like, “Come on, suck it now.” He caught my head and pushed his cock deep into my mouth till I gagged.

I also played around with his balls and had a bite of them. After some time, he had a bit of pre cum. He threw me on the bed and came on top of me. He bit my cleavage and licked my navel.

He later slid my bra down to expose my sissy tits and started sucking them. He was alternatively sucking and squeezing each boob. I felt I was in heaven. I caught his hair and caressed it as he kept sucking and squeezing my tits.

He slowly went down, kissing my navel down and removing my panty, sucked my cock deep. I went on top of him, holding his head as he sucked my cock. Now, it was almost time.

He made me turn around and licked my asshole and fingered it. I felt I had done a good thing by expressing my desire to him. His tongue was magical. I was itching to take his cock in my hole. I told him the same, and he started to insert it in.

It was painful, so I told him to go slow. But he pushed it into my ass hole in the doggy style in one go. It was pain and pleasure at the same time. Later, we changed to missionary with him on top, and he continued banging my ass.

It was a slightly uncomfortable position for me, to say the least. My feet were facing up awkwardly. It added to the pain but no complaints. He drilled my asshole by looking into each other’s eyes.

He got hold of my boobs again and squeezed them hard. The pain in my ass and boobs was unbearable, and I let out a scream. He loved that.

After some time, he reached an orgasm and slept beside me. I started to stroke myself with one hand on his chest. I lay beside him with memories of my first sex.

I wanted to get ready as usual and go, but my ass was hurting. He told me to get into a sissy dress again and have one final long kiss.

Secret Crossy sissies and CD Admirers, mail me your suggestions and comments at [email protected].