My name is James. I have been crossdressing since I was in my teen years. It started when one time, my sister decided to dress me up in her pink frock just for fun. After that everything changed. I couldn’t stop thinking about dressing up in cute dresses and every time I saw any girl in a lovely dress, I couldn’t stop fantasizing about how I would look in them.
As time went by, my interest on feminine things grew more and more. Having an older sister, I had many opportunity to wear her lovely outfits when no one was around. My favorite item was her blue bathing suit. I just felt so girly and pretty when I wore it. I didn’t knew why I loved dressing up as girl and what it really meant.
My parents were quite strict so I was extra careful every time I got dressed in my sister’s clothes. Usually all her dresses fit me well and soon I also started to try out some of her bra. It was usually for a very short amount of time. I just put them on wanting to know how they felt and then take it off immediately because I was really scared someone would catch me like that. But this really made me feel so excited.
As I grew a little older, I couldn’t really sneak into my sister’s room and from the internet discovered that I was actually a crossdresser who liked dressing up as a girl every now and then. I felt a little relived knowing that there were many people like me who loved to dress up.
I tried really hard to resist the urge to dress up but every time I was alone in the house, I just wanted to sneak into my sister’s room and try one of her outfits. Few times when I had the opportunity, I would wear one of my sister’s dress and roam around the house. It felt so wonderful. But I felt guilty every time after I had crossdressed. So, I decided to put a stop to it.
Fast forward to my college years, I hadn’t crossdressed for a long time. But then as I moved out of the house to an apartment near college, I couldn’t fight the urge to dress up and then brought some cute dresses, pantyhose, heels and a hair wig. Slowly, my collection of feminine wardrobe grew and I was mostly dressed as a girl inside my apartment.
Due to my crossdressing habit, I was quite an introvert and shy to interact with other people. I loved spending time alone and just dressing up and trying to look as feminine as I could. I even went out in public few times dressed as a girl and it was so amazing to me.
But time and again, I would really feel bad about my crossdressing and then throw out all the clothes and feminine stuffs that I had brought and try to live a normal life. I crossdressed on and off for quite some time and after college, when I started working, I completely stopped to crossdress.
I found a lovely girl and we fell in love and then got married one day. I was very happy but at the back of my mind, I was always interested in women’s clothing and fantasied about dressing up as a beautiful woman every now and then. But I was really scared to tell my wife because I didn’t want to make her feel bad about it. So, I kept silent about it.
After few years in our marriage, my wife got a job as a business development manager for a very reputed company and her job had her going away on business trips more regularly. I was mostly alone at our house and again, the urge to dress up started to grow stronger and stronger.
So, I decided to dress up when one time, my wife told me she was going to be away for a whole week. After she was gone, I brought few dresses, hair wig and heels online. It was so thrilling to be dressed again. I felt like I was reborn again. I got dolled up from head to toe and couldn’t stop admiring my own looks in the mirror.
I must have taken like thousand of photos and videos of me going around the house. I was too scared to go out in public but I did step out in the balcony at night fully dressed from head to toe. It was an exhilarating feeling. I dressed everyday for the whole week my wife was away and when it was time for her to return. I just got rid of all the stuffs that I brought and promised to never dress up again.
But every time my wife was going away for a longer time, I would end up ordering all the feminine stuffs again and then get back to crossdressing. This probably lasted for almost a year. I would buy few things, dress up and then throw it away.
I was spending too much money doing this so I decided to hide some of the feminine wardrobe in our store room. My wife was great at her job and she got promoted. She started to have more responsibility at work and would have to fly out without much notice sometimes.
When she was out, I would then take out my secret stash of feminine items and get dressed and enjoy myself. One day, I finally decided to step out of the house dressed as a woman in the evening because I started to get bored just dressing up inside the house.
So, I got dressed up from head to toe. I put on a lovely pair of black lingerie and then put on a black dress, pantyhose and heels along with a nice shoulder length hair wig. I did my makeup and I was ready to go out.
My heart was beating faster as I took the first few steps outside the house. I planned to go on a short drive around my neighborhood and be back home. So, I got in the car and went on a short drive. It was so wonderful and my whole body was trembling with excitement. The trip went really well and I was really happy about myself.
When I was just about to reach home, I got a call from my wife. She was supposed to arrive after 2 days but she told me she was on her way home and would arrive in few hours. I started to panic now. I had to remove all my makeup, then hide all the stuffs before she arrived. So, I rushed back inside the house, trembling and scared.
I had to act fast and get rid of everything. I had heavy makeup on and even had nail polish in my hands and toes. So, I went straight to the bathroom, got undressed and started to remove my makeup and the nail polish as fast as I could. Then, I took all the clothes, makeup and shoes and put it in a bag and hide it in the store room.
I got dressed in my male clothes and double checked if there was any makeup visible in my face. So, i washed my face again until I felt sure there was no trace of makeup in my face. After I was done, I was completely exhausted. I decided to crash on the sofa for a while. Just as I sat down, the door bell rang and I jumped from the sofa completely terrified.
I tried to calm myself down and then went to open the door. I was still nervous if she would suspect something but with a smile I opened the door and welcomed her. She looked exhausted from her trip and said she wanted to take a shower to freshen up.
I decided to make her some food as she said she was a bit hungry. She went into the bathroom. I was just going to the kitchen when she called my name really loud. That really frighten me and I thought if I had forgot to hide everything of my feminine stuffs.
As I came out from the kitchen, to my horror, my wife was standing there with a bra in her hand which somehow I had missed to hide. She looked quite angry and I was terrified. I just didn’t know what to tell her. She was staring at me to explain everything to her. That was how I was caught crossdressing by wife.
I haven’t felt so embarrassed my whole life. I froze and couldn’t decide how to say it to her. My wife then cried out why I would cheat on her with somebody else. Then, I realized something. My wife was thinking I was having an affair with someone as she thought that the bra belonged to some other woman.
I couldn’t keep my crossdressing a secret any longer. So, I told her everything about my crossdressing and I could tell from her expression that she was quite shocked. After I finished explaining to her, she was still not convinced. So, I took out all the feminine stuffs that I had hidden in the store room and showed it to her. Then, I showed her pictures of me dressed as a woman.
She was silent for a while. I could understand her reaction. I apologized to her for keeping such a secret from her. After that, she went to bedroom and we didn’t speak that whole night. I felt so bad about myself and I sat in the living room feeling so upset and embarrassed about my actions. I had no confidence to face her so I slept on the couch in the living room.
Next morning, my wife came up to me and she looked much calm that the night before. I apologized to her once again and told her I would really stop crossdressing. She then held my hand and told me it was okay and she wasn’t angry at me. I felt a little relieved but still very embarrassed. We talked about my crossdressing for many hours that day and she told me it was okay as long as I wasn’t gay and had no interest in her. I told her I really loved her and crossdressing was just something I did for excitement and I was not gay.
After that day, my wife allowed me to crossdress inside the house. I couldn’t believe how supportive she was to me and I felt so grateful to have her in my life. Slowly as time passed, she accepted my crossdressing more openly and sometimes helped me get dressed and also teased me on how cute I looked. It was really wonderful to have the weight of my shoulders about keeping my crossdressing a secret.
Sent by James Carter