Secret of my roommate – Part 1

Hi, my name is Ash. This is a story about me and my crossdressing roommate, whom we can call Sultana (name changed for this story). Actually, she is from the south side, has a dusky complexion, a slim figure, and is 5’8″ tall, with some extra cuteness in her pants.

So, let’s start my story: how I met her, how I learned about her secret sissy and crossdressing life, and more.

The story starts at Pune University, where I got admission for my degree. I shifted to Pune and got a paying guest (PG) accommodation for myself, which was near my college.

While I was shifting my things into the room, I found out that I was getting a roommate because the owner was also letting him live in the same room as me, which was actually normal for PG renters.

As I was arranging my stuff, he also arrived with his luggage and started arranging his things.

When he came to Pune, his family also came with him to help: his father, his mother, his sister, and him. They were all there, and I was the only one in the room standing by myself because my mom couldn’t travel from Mumbai to Pune due to some personal work. My dad had only come with me and helped me arrange my stuff.

My father and his father started chatting, while his mother and sister started arranging his clothes and other things. He and I started introducing ourselves.

Him: Myself is S (for privacy, I only called him S after that, and then I started to call him Sultana). I am an IT student at a nearby university (I cannot disclose the university name).

Me: Myself is Ash. I am also from the same university, and I am also an IT student, which means we are going to the same university, lol.

After that, he started helping his mom arrange his stuff while I stood behind them, watching them. My dad was still chatting with his dad about our grades and behavior, etc.

While arranging S’s stuff, I was watching S’s sister, who looked gorgeous in a green kurti with her milky-white skin and slim figure. As I was watching her, she noticed that I was looking, and she glanced in my direction for a few seconds and gave me a cute smile.

S also noticed, but he didn’t see me watching her; he only saw his sister and me exchanging smiles. But his sister knew I was admiring her and looking at her butt and boobs.

After arranging everything, my dad and S’s parents left for home. S and I started chatting about each other’s hobbies, study ideas, favorite sports and games, and other things. After that, S told me he felt sleepy because he had traveled from Kerala to Pune and needed some sleep, so I told him to go ahead.

After that, I opened my laptop and started playing a video game. I know I started playing from 3 PM and played till 8 PM because I was playing Valorant, and it’s a damn hectic game because a rank push isn’t easy.

When I checked the time, I felt hungry, so I thought I’d order some food for both me and S for today, as the owner had hired a maid for us at a reasonable price. We asked him to tell her to come starting tomorrow.

Before that, I thought I needed to relieve some stress after the hard rank push. I considered watching some naughty videos, so I logged in to my account and chose my favorite preference: trans porn. Yes, I am a bisexual top who likes both males and females, but I only prefer sissies and trans girls.

Don’t get me wrong, normal girls are ok, too!

So, I started a ladyboy porn video where a cute Thai ladyboy was sucking a nice cock while the guy was jerking him off. She had some nice petite boobs and a slim figure, which looked more adorable and gorgeous.

I looked at my surroundings and checked the door locks, and I also checked if S was sleeping or not. Then I started watching the video.

For me, trans porn is something that makes me dizzy, and my mind goes blank while watching it.

While watching the porn, I pulled down my track pants and lowered my underwear, freeing my 5-inch dick, and started jerking it as the video intensified. My jerking speed also increased. I was wearing noise-cancelling earphones, so I could hear the video’s sound more clearly without any interruption.

While I was jerking off, I felt a hand on my shoulder. I got scared, and because of the shock, I accidentally came on my laptop.

Fearing I’d been caught, I quickly stuffed my dick back in my underwear and looked back. When I looked back, I saw S standing behind me and looking at me. When he looked at me, he looked directly into my eyes, which made me feel as if he was looking into my soul. I locked eyes with him, and we both stared at each other for a few seconds.

S: You like trans sex?

Ash: Yes, actually, I am –

S: It’s ok, I understand. You’re bisexual.

Ash: Yes… Actually, I like trans people.

S: And?

Ash: Anddd, umm…

S: Don’t worry, tell me. Actually, I am also bisexual.

Ash: Really?

S: Yes. Actually, if you don’t mind, I have a secret to tell you because you’re also bisexual, but I want you not to judge me, ok?

Ash: Yeah, sure, why not? Tell me.

S: First, start that video. (Actually, because I was scared of getting caught, I had stopped the video).

I clicked the play button and started the video. S sat down beside me. He looked at me and asked if it was ok if we both did some mutual shagging. I was like, yeah, why not, and I started removing my bottom clothes while he also removed his.

(When he started removing his pants, he stood up and turned to the other side while pulling them down, which gave me a chance to see his dusky ass. It looked bubbly and was hairless, much like his crotch).

After removing his pants, he sat beside me and started watching the video as the ladyboy in it started jerking the actor’s dick. I started jerking mine, and S started jerking his cock.

At first, I didn’t notice much, but after some time, I looked again, and his cock was still small even though it had veins on it. While we both jerked off for 5-6 minutes, S suggested that we should jerk each other off.

I hesitated because I’d never let anyone touch my dick – yes, I am a virgin – but S kept requesting, so I couldn’t refuse anymore. I let him touch my dick. When his soft hands touched my cock, I felt a jolt in my body and couldn’t think straight anymore.

While he was jerking me, he gestured for me to jerk him off too, and I nodded and took his small, circumcised dick in my hands.

Yes, he had a circumcised dick, while I have an uncircumcised one. It was my first time seeing a circumcised dick.

As we both started jerking each other, it got more intense because we could hear the ladyboy’s moans filling our room as she got nice back shots in the video.

We both started jerking each other passionately. After some time, S told me he was close to cumming, which made me hornier, and I started jerking him faster. After a few moments, he splashed some cum ropes onto my laptop and the bed.

As he came, I don’t know what happened to him, but he hugged me tightly, grabbed my dick, and started shooting his cum, which also brought me close to cumming.

He put his head on my shoulder and started jerking me again while I was still watching the video. After a few more jerks, my dick also started signaling that it was about to cum, which S noticed, and he started jerking me slowly and gently.

This started giving me both pleasure and pressure at the same time because I couldn’t handle the buildup. I asked S to jerk me faster so I could cum.

He looked at me, bit his lip, and gave me a naughty smile. He then spit directly from his mouth onto my dick, which made me feel his warm saliva and drove me crazy.

I looked at him, and I don’t know what came over me when he was biting his lip and smiling at me – I kissed him.

When I put my lips on his, I felt that his lips were too soft and squishy, and I couldn’t resist. I started putting my tongue in his mouth, and he cooperated with me.

While kissing S, hearing that ladyboy’s slutty moans, and feeling S’s soft hands on my dick, I went crazy and came again, shooting some cum ropes onto my laptop.

After this intense session, we both got up and cleaned each other off. I looked at my messy laptop, which had some cum on its screen, which made me feel dizzy and tired.

S looked at my tired face, and I don’t know what got into him. He started licking my laptop screen, which shocked me. After a few licks, he had cleaned my laptop display and gave me another naughty smile.

After this mess, we both sat beside each other. I was still thinking about that kiss when S started saying something that shocked me again.

S: I need to tell you something about me and why I chose this university, which was far from my family and home.

Ash: Tell me, I’m listening.

S: Actually, I’m a secret crossdresser who likes to wear girl’s clothes and feel girly when I see boys.

Ash: Really, is this true, S?

S: Yes, it’s true. That’s why I chose to live far from my family, so I can live freely.

Ash: Damn, I’m so lucky that I have this dusky, cute crossdresser near me who is actually sluttier than an actual slut.

S: (Started blushing) Really, Ash, you like my secret?

Ash: Yes, Miss Sultana.

S: Sultana, who? I’m S, Ash.

Ash: From now on, your name is Sultana… my precious crossdresser princess.

Sultana: Really?

Ash: Yes… from now on, you’re my princess.

Sultana: Aww, really? You like me that much, Ash?

Ash: I will prove it to you… but for now, we need to eat something, or else I’m going to collapse. Let’s order something online. And also, while we wait for the food, let’s look at some cute dresses for you, Sultana.

*****

Ok guys… for now, I’m ending this here because it’s late at night and Sultana and I are both tired. Yeah, she’s sleeping next to me, looking at me and jerking me off while I’m writing this story for her. And now, she’s started blushing and cumming.

I hope that, just like she likes the story, you guys have liked it so far.

I’m ending it here, so please love my story and get ready for the series, “Secret of My Roommate,” because this is going to be a bit long.