Crossdressing Stories

Best Friend Finds About My Crossdressing Secret

Best Friend finds about my crossdressing

Story Title: Best Friend Finds About My Crossdressing Secret
Sent by : Rachel Valentine, United States

” I am a 22 year old guy living alone in florida pursing my college education. Its been 2 years that I have been living all my myself. At the age of 16, I realized I was really interested in crossdressing. I was especially attracted to cute dresses that my sister used to wear. Whenever I saw girls wearing cute dresses, I would get very fascinated with the outfit rather than the girl.

My first time dressing up was when I was 14 years old. That day, I was alone at my home. I sneaked into my sister’s room and tried on her school uniform which was a white shirt, grey pleated skirt, black knee length socks and a tie. It was a tremendous feeling and I loved it. The experience of being & feeling feminine was just amazing.

Since that day, I started to get dressed secretly whenever I had the chance. I used to feel so happy when I knew I would be all alone in the house while my family was away on different occasions. At first, I was sneaking in my sister’s room most of the times but her wardrobe used to be locked and I could only wear the clothes she had left outside. One day, I found out many old dresses and outfits of my sister in our storage room. I figured nobody would notice if these dresses were missing. So, I would sneak 2 or 3 dresses with me in my room and get dressed in them at night, when i had some privacy.

Gradually, i got bored with my sister’s used up clothes. I would spent hours looking at online shopping websites to find the perfect dresses. I started to buy many things online and I was running out of places to store them in secret. I was also having problem with privacy and could only dress up at night in my room only.

So, long things short, I moved out of the house. Got my own place and now had the freedom of dressing whenever I wanted. When i moved into my new apartment, I used to get dressed the whole time for months. I brought so many feminine things and even a pair of realistic breastform. My makeup skills got better and so did my feminine impersonation & personality. I could easily wall in 5 inch high heels and get my body to appear curvy & feminine.

I loved taking videos & photos of myself. I used to spends hours just posing in front of the camera and would post some of the photos secretly in crossdressing forums online.

Soon, I got bored of just dressing up inside my apartment. Now, I wanted to go out in public as a girl and experience what it was like. So, one night, I dressed myself up in a cute summer dress & black pantyhose. I did my makeup in a simple way and also wore a black wavy hair wig. I remember feeling really excited to leave the apartment. That night, i explored around my neighborhood for half an hour and came back to my apartment. It was scary to be exposed so openly but at the same time it was really thrilling & adventurous.

I started to go out more frequently since then. Every time I went out, I tried to go to a new place. I used to go to a lot of department stores and do shopping.

I didn’t have many friends and didn’t used to go out much with them. One of my close friend was Gary. He was a gamer like me and we used to play a lot of pc and playstation games. We exchanged many games and it was fun hanging out with him.

No body knew about my crossdressing. It was a secret that I didn’t really wanted to share with anyone. But that was going to change soon.

One evening, I planned to go out shopping in my feminine attire. I got dressed up & left to visit a mall. I did a lot of walking and shopping. I brought a few clothes & some new games. It was a great evening. I returned home exhausted and couldn’t wait to get some food & a drink. I reached my apartment and as I was about to unlock the door. A guy from behind called out to me. I completely jumped in surprise.

When i looked to see who it was, my heart stopped beating. It was my friend Gary. I was so embarrassed. But Gary was smiling at me and I just sat there for a moment not knowing what to do. Then, Gary finally spoke to me.

“Excuse me, I am a friend of Daniel. I was just passing by this neighborhood and thought i should make a visit but he wasn’t at home and he is also not receiving his phone. May i ask who you are? I haven’t seen you before.” Gary said.

I was surprised he didn’t really recognize me and thought I was actually some other girl. But I was completely blank. I just stood there thinking how much of trouble I had got myself into. If I spoke, Gary would surely know it was actually me. He was looking at me for a reply. I didn’t wanted to create any scene so ,trying to think straight. I opened the lock and stepped inside the apartment. I ushered Gary to come in and he did.

Finally with all the courage I had, I started talking and I could see Gary’s face getting completely shocked.

I said ” Amm.. Sorry Gary but this is actually me, Daniel. I was just… trying to .. you know.. know what its like.. to dress…to you know.. try…”. I was having hard time completing a single sentence.

Gary just sat there amazed to see me dressed like a girl. Then after some moments, he spoke.

“I had no idea that you had such a secret. But to be honest, I still can’t believe its really you. You really look like a cute girl.”, Gary said.

I didn’t knew how to respond to him. But he had now found about my secret. I had to talk to him about this and convince him not to tell anyone else about this incident.

I spoke out ” Sorry Gary, you found me like this. I am very embarrassed. Please don’t tell this to anyone. Nobody knows about this. Its been some time that I started dressing up like a girl.”.

Gary looked at me still looking very surprised.

“Okay, I will not say this to anyone. But it’s so scary that you look so beautiful as a girl. If I hadn’t known it was you, I would have surely asked you on a date.”. Gary said jokingly.

I was blushing and it was my first time talking to someone right in-front of me while I was completely dressed as a girl. Now that Gary had seen me like this, I felt there was no hiding it from him and started telling about my crossdressing and how I liked dressing up as a girl. Gary listened to me the whole time without saying any words.

After I finished talking, I felt a little relaxed. Gary was also smiling and I smiled back. We then talked about how I looked and Gary kept complimenting me. He admitted I was the first crossdresser he had seen in person and he was totally okay with it.

Having this conversation with Gary was making me feel a little aroused. I felt good being able to share my feminine self with someone else. Then we started talking about games. I showed him the new games that I brought. I asked him if he wanted to try it with me now. He said okay.

So, I took out the game and put it on the play station. I was just getting the controller from the desk when Gary stepped really close from behind and I had a mini heart attack. I blushed and he noticed it.

” Do you by any chance like guys?”. Gary asked curiously.

” I.. I don’t know. I never thought about it.”. I replied feeling shy.

” Would you like to.. maybe go on a date with a guy? Gary asked.

I couldn’t even look at Gary. I was feeling like this for the first time. I felt very shy but aroused as well. Gary was eyeing me from head to toe and I knew he was getting interested in me. So, to break the tension. I tried changing the topic back to the game.

As the game was loading, we both sat there silently and then suddenly Gary noticed my bulge in the dress. He then got up and got behind me and grabbed me. I was completely speechless. He slowly started to move his hands around my body and my bulge was only getting bigger.

Then he turned me around and kissed me on my lips. I kissed him back. We hugged and he was touching me every where. After quite a few minutes of kissing around. I asked him to stop and then was a moment of silence. Gary then confessed he was finding me very attractive and wanted to get more closer with me. I told him to give me some time to think and I ask him to leave.

After he left, I simply sat in the couch thinking why it really happened with me and how embarrassing it would be if Gary told others about my crossdressing secret.

(Story will continue in Part 2) – Coming Soon !!

Facebook Comments


  1. Very interesting story I wish I were you

  2. great story , O how i love to dress an have a good boy friend to sleep with

  3. great story , Oi love to dress up as much as I can , it is ok with my wife , an she like to watch me with other men in bed

  4. Please. Part 2!!!

  5. wish that would of happen to me when i was 14 with one of my friends, would not of though about it,

  6. If you were getting aroused, I’m sure he was even more. I don’t see a part 2, but I hope you two were able to explore your arousals together sometime.

  7. Looking forward to more of your story. I’m a crossdresser myself and actually fantasize about something like that happening to me. All I can say is that it would only go further if my wife set the whole thing up. She doesn’t know it, but in my mind she has the ability to turn me into a real crossdressing slut for cock.

Leave a reply

Your email address will not be published. Required fields are marked *

You may also like