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Caught Crossdressing by My Roommate


The real story of a crossdresser who got caught crossdressing by his roommate:





A crossdresser’s journey of fear, discovery, and acceptance


My Secret Crossdressing Life


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My name is Marie, not my real name; it’s my femme name. Wait until the end for my real name.


Anyway, just like any other closeted crossdresser, I also live a regular crossdressing life, and this is my story of when I faced my biggest fear: being caught crossdressing by my roommate.


Back in my college days, I was living a regular lifestyle as a college boy in a college hostel, and my cross dressing secret was hidden beneath the surface; no one knew about it. It was a secret that I kept to myself, hidden away like a precious gem.


For me, cross dressing is not only about clothes; it’s about feeling femininity from the inside, and that’s why I have given myself a feminine name.


I love the idea of being a college girl – I wanted to dress in college, join the cheerleading squad, put on slim-fit jeans and a crop top, and flaunt my midriff.


Yeah, I wanted to do all that, but life is life.


College dramas like ‘Mean Girls’ and ‘Jennifer’s Body’ are my favorite movies because I wanted to be like those girls. But I’ve got to keep all of that, of course, to myself.




My cross dressing wardrobe was carefully hidden behind my closet, full of feminine stuff that made me feel like myself.


It was a typical college girl wardrobe, with crop tops, short skirts, and my favorite – a pair of red, lacy panties with a matching bra.


I also saved some money and bought myself breast forms, which gave me that perfect feminine silhouette I always wanted.


When I’m dressed up, looking at myself in the mirror, I see the real Marie looking back.


I can never forget my college dorm; I spent hours experimenting with feminine clothes, practicing makeup, lounging en femme, and just living in the moment.


It’s these times, behind a closed door, that I feel most at home in my skin.


My Roommate Kyle and Me




Here’s a new entry in the story: my roommate, Kyle. Kyle, by the way, is his real name. He was just the complete opposite of me.


While I was a soft, cute, patsy twink, he was all about sports, muscles, and that effortless kind of charisma.


What I really loved about Kyle was his laid-back attitude and sense of humor.


He was funny and had this ‘light up the room’ personality that just drew people in – myself included.




Me and Kyle had a very nice bond, and we still do. We’ve shared a lot of conversations, just like buddies.


I knew about his likes and dislikes, and he knew that I kissed a boy when I was in high school for a dare.


Kyle was fun; he had this habit of playfully teasing me, calling me ‘princess’ or ‘sweetie’ in a joking way.


You know, those college boy things. I know he meant nothing by it, but sometimes I couldn’t help but wish there was a bit more truth behind those words.


Trans lifestyle


He has a girlfriend, and I honestly never liked her. Maybe I was jealous, or maybe it was something else.


I don’t know even now, but I have complex feelings for Kyle.


I was definitely sexually attracted to him but kept telling myself to control it because he was straight, and in his eyes, so was I.


The Moment of Getting Caught Crossdressing


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I can never forget this moment in my life. It was the evening when Kyle left for home, and I was happy to get my femme time.


I remember the moment exactly: I had my headphones on, dancing to ‘Barbie Girl,’ living some of the best moments of my life.


I was wearing my favorite pink crop top and high-waisted pink panties with my breast forms; everything was so perfect.


Dancing in front of the mirror, admiring my feminine self, I felt so feminine that day with those breast forms. It was perfect until then.




I heard someone opening the door, and the world stopped. Kyle was standing right in front of me, his expression a mix of surprise and confusion.


All I could hear were my thumping heartbeats. This was it, my biggest fear coming to life.


Caught in my most vulnerable state, I got caught while cross dressing by my roommate.


I couldn’t even begin to process what would come next and burst into tears.


After Getting Caught Crossdressing




At that moment, I felt like it was the end of our friendship, the end of college, and the end of my life.


I was sobbing, standing in the corner, and Kyle’s eyes were fixed on me. I couldn’t read his expression.


Was it shock? Disgust? Curiosity? I had no idea what he was going to do next.


Finally, he broke the silence. ‘Howard?’ Yes, that’s my birth name, one I never resonated with. The name never felt like my true identity.


And I started crying more loudly and got down on the floor, said crying out, ‘Please close the door.’






He closed the door and came to sit right next to me, consoling me first. I wiped my tears, and he told me to speak.


I gathered myself for the moment of truth, ready to tell him everything about myself and prepared for rejection and the loss of the camaraderie we had built as roommates.


But then Kyle did something unexpected. He said, ‘I… I didn’t know,’ his voice softer than I’d ever heard it. ‘Why didn’t you tell me?’




The question hung in the air between us. Why hadn’t I told him? Mostly fear. Fear of losing the one person in this place who made me feel less alone, even if he didn’t know the real me.


‘I was scared,’ I admitted, my voice barely above a whisper. ‘Scared you’d hate me, or worse, that you’d leave.’


Kyle’s expression softened, and for a moment, I saw something in his eyes that looked like understanding. ‘I don’t hate you, Marie. I’m just surprised, that’s all. I mean, this is a lot to take in.’


We sat together for hours that night, and I told him everything about myself, my struggles, my fears, and what feminine dressing meant to me. He listened, really listened, and I began to see a side of Kyle I never knew existed.


Life After Getting Caught




The next day was very awkward. A new kind of energy between me and Kyle that I had never felt before.


But Kyle was trying, I could tell.


He wanted to make me feel comfortable, asking me questions like whether I had preferred pronouns or if there was anything I wanted him to avoid or do differently.


His effort was genuine. The teasing stopped, replaced by a more thoughtful kind of interaction.


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For me, the changes were very positive, and I became freer and more confident about my femininity in front of Kyle.


I didn’t dress up as freely as I wanted to, not yet, but I didn’t hide it either.


I didn’t want to make Kyle suddenly uncomfortable; I just wanted to do it gradually and slowly.


That’s why I crossdressed partially with an androgynous approach in front of Kyle.


One evening, while having drinks in our room, I felt Kyle wanted to talk to me. So I told him, ‘You want to speak, bro?’


Then, he took a deep breath. ‘I’ve been thinking a lot,’ he began, ‘about you, about this… situation.


I don’t understand it all, but I want to. You’re my friend, Howard, and that’s what matters.’


Trans lifestyle 


His words were simple, but they meant everything to me. I felt so emotional like it was a balm to my soul.


That’s the charm I was talking about; this boy had. He valued friendship and understood others’ differences.


I didn’t know it was going to be that easy.


There were still many feelings that I wanted to share with him, but I decided not to for the sake of our new friendship dynamic.


General Advice


sissy boy 


The moment of getting caught crossdressing can be agonizing, but it’s also incredibly liberating at the same time.


The realization of liberty happens after a few moments.


I would’ve never thought that the biggest fear of my life was nothing but just a perception in my mind.


After that, I realized that the fear of getting caught or coming out as a crossdresser is very misunderstood, and sometimes, the people around us can surprise us with their acceptance and support.


Here is my advice to you being a crossdresser.


If you ever get caught while crossdressing by anyone, Whether it’s a roommate, a friend, your mom-dad whoever, make sure you’ve an honest conversation with them rather than dodging the questions and running away from the situation.



More often than not, people appreciate sincerity and are willing to understand.


Another thing is that your crossdressing journey is different from others.


You might not find a Kyle in your life, but whoever you are with and get caught by, always remember people might take time to fathom the entire drama.


Things might take time to normalize, but make sure you’re treated with respect.

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