I thought all this Sissy got caught porn are foolish until my roomie caught me

NSFWStory

So I (Sissy CD 20) had been crossdressing for a while since I was 16, but last year i had to leave my hometown and went to a new city for my studies. I got into a hostel, so i thought i would forget the crossdressing addiction as there was no way i could get a girl's cloth in all boys hostel, and I thought I would get normal again, I was wrong.

All these sissy caption, sissy porn games kept me hooked with my sissy side, though I was not interested in men and their cock.

Then once i got to know about Grindr, i installed it just check out, but well eventually ended up serving men on vc by finger fucking my ass as a slut. The best part was I got some money out of it, which I used to buy some lingerie, a pink set, & a white shirt.

I always had a kink to dress up as a bimbo secretary.

So back to the story, i ordered those and after a week i got a call from delivery guy, i asked him to leave the package with guard. Silly me, the clothes came with a transparent pack, who in the normal world would have thought about it.

I got so dirty looks from the guard while i went to collect them, so just to be safe, i acted as if that package was of my girlfriend.

Anyway got to the room and locked it, got nude and started dressing up, i stuffed my bra so it could get a proper boob shape, i paired the shirt with a black tight skinny jean that I had. I also gave a show to my grindr daddies.

All this went good for a month.

Until I fucked up one day,

One fine afternoon i was dressing up and forget to lock the door, as usual i did my things, dressed up, masterbated but i did changed, got on my bed to get a 5 min rest, but instead I slept. And to my horror, when i woke up, i panicked as I saw my roommate standing along my bed looking with downeyes at me.

We both were shocked, but he broke the ice, asked me what is all this, while i was covering myself with a blanket as i was still dressed up.

I told him my truth, he heard me and went out without saying a word for a cigarette. Meanwhile he was out, i changed up and cleared the mess, and went to shower. After the bath i came out, with a towel wraped around my lower body, (btw i am not too fat or too slim, average body, big ass and a bit of man boobs, with small clit) and as soon as i got out, my roommate lets name him perk, perk came in, he came in, locked the door, and came near me, my heart was racing but i thought he was ok with my true side, and then he snatched that towel away, leaving me naked, i felt so humiliated at that moment, no where close to arousal. I ran into my blanket, furious I asked perk, "wtf are you doing, i will beat ur ass up" and in response he showed me the pic of dressed sleeping sissy on my bed (me). I froze and then he gave me a tight slap, showing where i belong. He asked me to be his personal slut, wear the dress again, with my brains out i did, and ofc from that day onwards he fucks me the way he wants, he got me some new clothes, wig and makeup. In return i eat several loads of piss and cum. He did all dirty things possible to do. Trust me from then i cant stop being a real cock hungry sissy. Within month i can notice difference in my behavior and body, btw i love it.

Posted Jun 2, 2026, 1:13 PM UTC

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