Crossdressing Stories

CAUGHT ONLINE

Caught Online Crossdressing Story

I was all alone in my house, this night my life changed forever. I was simply looking for my sister’s iPad when I went into my sister’s bedroom. She’d left her lingerie drawer open and suddenly all my attention was focused on the lacy white corset on top. Nothing else mattered, nothing else existed, and nothing could have torn my attention away from it.

I just had to put it on! Then, of course, I needed nylons and panties to look right. Girls didn’t run around in just lingerie so a dress and heels followed and at the age of eleven I became obsessed with dressing myself femininely!



At home it was too crowded to have any privacy usually and I just knew that everyone would ostracize me if they found out. Boys didn’t wear girl’s or women’s clothes! But every chance I got, I eagerly found myself dressing from the skin out in female clothing! It was never enough just to wear one item or only lingerie’, I had to dress fully! When I was dressed there was just the serenity and peacefulness of feeling feminine while time seemingly stood still and nothing else mattered.

Why I’d ask myself after, why was I so different, but there was never any good answer. It was a part of me that took a long time to accept. A part that gripped me and held me captive in a compulsive obsession I couldn’t fight or resist in any way. And as I was to discover a part that would last the rest of my life no matter how I might try to resist or stop myself from dressing up.

As the years passed it wasn’t enough to simply wear women’s clothing. Women did so much more and now I had to as well. Long hair for males was the norm at the time so I learned to style mine into a very feminine pageboy.

I polished my nails, both fingers and toes. I experimented with make up till I was able to do my face as well as any thirteen year old girl. I’d shave my body and legs to be as femininely smooth as possible; never once stopping to think about or remembering that it wouldn’t grow back overnight.

When I moved out on my own it became easier to indulge but also harder to hide my obsession. Friends and family don’t always call before they drop over and there were a few scary moments when I was nearly caught. Sometimes I left something out in my rush to change back or discovered that I hadn’t quite removed my make up or my nail polish fully after I’d let them in! I prayed that they wouldn’t notice.




It was a rewarding part of my life but still a very lonely one in many ways. Then came the time I found myself peeking out the door at two in the morning, daring myself to walk down to the other end of the hall and back.

Rushing out the door and stumbling along the hall, all my femininely graceful ways forgotten at first until a part of my mind reminded me that I was supposed to be feminine. Slowing down, adding a feminine sway and gait as my heart pounded so rapidly then walking carefully down to the end of the hallway and back until I was within ten feet of my door.

Rushing to get behind it again and close it. Feeling so exhilarated and thrilled that I’d actually done it. From there I increased my dares to actually having to go onto the landing and stand there for a whole minute or two; to go as far as the front or rear door and stand there at first, to stepping outside and walking around to the other door while dressed!

It was so very, very intoxicating to savor the sensations of being outside dressed. Like the swirl of cool air around my legs and under my short skirt, the tug and stretch of my garter straps along my thighs, the way my nylons felt as they rasped together with each step, hearing the click of my heels against the concrete!

Eventually I dared myself to go as far as to walk around the block. Even more exciting, more intoxicating and oh so much more scary all wrapped together! Not that anyone else was there to share it with or see me.



Daring myself to go further, to add another block to my walk, and another until during one late night walk someone came out of a house and looked my way. I ran like the frightened little girl I was aping and hid behind some trees till I was sure I was alone again.

The world didn’t come to an end the next day! There was no headline in the paper revealing my secret to the world! My friends and family still didn’t know and confront me. Why had I thought they would and been so scared? Was I that ashamed of what I was doing? If I was, why did I continue to do it? Still my world hadn’t ended from that brief encounter, if you could even call it that, and I felt better now about being seen from a distance.

Not that I became more brazen immediately or went out of my way to be seen but I pushed my limits harder and started going out for walks earlier and earlier. I forced myself not to run when someone was within half a block, stall for time by looking in my purse or turn around and go back. It wasn’t easy to do I was so nervous but as no hue and cry or crowds chased me it did help me to relax and become more confident.

Confident enough that I was able to walk past a parked car with someone in it without rushing by. Confident enough to bravely enter a store and buy a chocolate bar. Confident enough to walk past other people walking down the same sidewalk without hesitating or dithering or turning my head. Heady stuff!

Not quite confident enough to do more than smile at a passing wolf whistle or offer of a ride. Not for another few weeks anyway. A further dare to myself made me get into a cab and try to appear relaxed enough to talk with the driver. He accepted me as a female, even my voice. Not that I did much of the talking. My confidence and self esteem soared!




When he parked in front of the house I was supposedly living in I started to get out but he grabbed my arm and pulled me across the seat for a goodnight kiss. His lips were pressed against mine, his tongue teasing my lips apart before I knew what was happening. Wonder of wonders I responded eagerly; teasing the tip of his tongue with mine as it slid between my lips.

Knowing that my voice had passed I did place an ad on an adult site using the name Amanda. I responded to messages and had a few live chats posing as a female, exulting in the idea that I could excite men into mastur-bating and even climax them just from the sound of my voice.

I did get into it and became fairly excited myself quite often but never did more than rub myself through my panties or pinch my nipples under my bra after the one time a guy wanted me to and I discovered how sensitive my nipples were and how sensual it was.

Things might have stayed the way they were if I hadn’t pushed the limits again and confessed to a few selected others that I wasn’t completely a woman. Only few people seemed shocked and hung up on me. The rest seemed to not only accept my obsession but became even more excited by the idea! I was in heaven.

Then one day as I was surfing the net, I received a message from a guy who wanted me to video chat with him. I had grown confident enough to do video chats and I accepted his proposal and messaged him I would video chat with him later that night.

I got ready as usual, got dressed up fully, put my makeup on properly and I was ready. I turned on my pc and found the guy was online too. I didn’t know his real name, only his user name which was “Sky534”. I was quite excited even though I had done video chats with guys before. I messaged him that I was ready and opened up the video chat.




There was something wrong with the video; all I could see was dark lines. The guy on the other end told me that he could see my video and it was coming fine. But my side of video transmission was just blank. I tried a few times but it was still not working.

Then I needed to go pee and left the computer as it was. After I came back, the video chat had been already disconnected and the guy was offline. I felt a little frustrated now as I was expecting to have a hot video chat.

As I was thinking about what to do next, my phone rang. It was Harry, my close friend from work. I answered the phone. As he spoke, my heart started to beat faster. He mentioned that he was video chatting with a woman but saw my room in the video and was shocked. I had invited Harry over to my house a few times in the past and he knew what my room looked like.

What were the chances that this would actually happen, I had never imagined. But there I was talking with harry, trying to invent some lie to tell him over the phone but nothing good was coming in my mind. He said he took screenshots of the video and had captured images of my room and also of the woman in the video, just in case there was something going on. I could feel my stomach just squeeze tightly inside me, I felt very scared.

How was I supposed to get out of this situation now, I had no idea. I tried one more time to tell harry that he might have just mistaken and it might just be some coincidence but he kept insisting and told me he was already coming over. I panicked and tried to tell him we could do that next morning but then the door bell rang. I jumped, scared completely. Harry had already arrived at the door. It was already too late to take off everything now.

I realized that my secret would finally be revealed. With a deep breath, I went to open the door to face Harry.

The End

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1 Comment

  1. Wonderful story ended the way I would like mine too

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