When I was about 22 years old, my friend and I opened a shelter for homeless dogs. We kept them in kennels in his mum’s garden as it was huge and they didn’t mind. I would go round in the evenings to feed and walk them as well as do any other jobs in the garden.
My friend was quite thin and his face was pretty androgynous. I would often tease him that he looked so feminine but only harmless fun . On this particular day, I went round 8 pm to feed the dogs and clean the kennels. My friend had told me that his family had a party to attend that day and no one would be home. I was supposed to be there around 7 pm but my mom gave me some chores to finish and it made me late than usual.
I was just about finished and it was getting dark when the kitchen light came on and grabbed my attention, I walked over to the garden tap to fill the water bowls up and glanced across into the kitchen. There was a cute girl with her back to me wearing a hot red dress with black stockings, I stood still and watched as she modelled the sexy costume for herself often running her hands over her body.
Her hair was short and her figure was quite attractive. I started to get a little arous-ed looking at her and wondering who it could be in my friend’s house. I had never see her before. I silently kept staring at her while she modeled in the kitchen. My thought was she was making a video of some sort.
I still couldn’t get a clear look at her face and as I was still wondering who she could be, then she turned towards the window and I noticed that it was actually my friend. I didn’t know what to do at first as I was shocked so I stood completely still so as not to be seen. I couldn’t believe it was actually my very own friend dressed as a girl.
I watched him walking in and out of the kitchen modelling this sexy red dress for about 10 min and I creeped closer to the window to get a better look. I must have cast a shadow or moved when I shouldn’t because he looked straight at me when he came back into the kitchen. I will always remember the look of fear in his face when he realized he was caught. He quickly ran back from view.
I stood there for a moment not knowing what to do and started to walk back to the kennels when the back door opened and heard my name called. As I got to the door he was trying to hide behind it and only opened the door slightly.
Then he said “Please don’t tell anybody about what you saw.”.
I could tell he was scared and I felt a bit sorry for him.
“Don’t worry” I replied, “I won’t tell anyone that I saw you dressed up.”
He then closed the door and I then walked away to the kennels to finish off.
After I was done and had time to think I decided to go back to the back door and knocked. He came and answered it but was no longer wearing the red dress.
“What happened to your sexy dress” I asked.
“I took it off because I’m quite embarrassed that you saw me like that.”. He replied.
“Don’t be afraid, I said I wont tell anyone and it looked nice on you. ”
His frowned face then changed and let out a little smile.
I said “I really thought you were a girl and you looked quite beautiful in that dress. I had no idea it was really you. How long have you been dressing up?”.
I could see he was embarrassed with my question and me finding out about his crossdressing. He was silent for some time and then finally replied ” I have been secretly dressing up for some times now. I don’t know why but I kept having these urges to dress in girl’s clothes and feel feminine. I don’t get to do it often, just when mom and dad are not around. Today, I thought I was going to be alone and decided to dress up but you saw me. Promise you won’t tell anyone about this please.”.
I nodded and promised not to tell anyone. I could still see that his face looked a bit worried, so I assured him that his secret was safe with me. We talked for a bit and he told me about his crossdressing desires. I was quite fascinated by them.
I asked him” When are your parents coming back? If you like, I can take some nice photos for you in that hot dress you were wearing.”
He looked surprised by what I said. He replied ” Are you sure? Wouldn’t it be awkward for you to see me dressed like that?”
I replied ” No, of course not. Since I already know you like to dress up. I might as well help you with it since I am your friend.”
He then said ” All right, I guess so. I have never dressed up in front of anybody yet and since you have already seen me. I guess I can trust you. Wait here and I will change and come back. My parents wont be back for another 1-2 hours I think.”.
After some minutes, he came back down, now wearing the same red dress and black stockings that he had before. I could take a proper look and he did look cute. Then he looked at me and asked how he looked. I said he was looking quite stunning and he blushed a little.
We both felt a little awkward at first and then I started talking & joking as usual. That made both of us feel more comfortable around each other. Then I offered to take some photos for him in the garden. He was quite shy at first but slowly got more comfortable to pose. I had no idea he could pose and look so feminine. He really looked pretty hot. After that, I left and he went back to his house. On my way back home, I couldn’t stop thinking about what a crazy evening that had been.
After two months of that incident, my friend opened up to his family about his crossdressing and they were supportive. Now, he has a place of his own and he has few crossdresser friends and he seems happy. We have also gone out a few times now while he’s dressed as a girl. It’s quite normal for me now.