This was a major event in my becoming a crossdresser.
I was 16 years old when this happened. My mom's best friend, Sue, and her family were going away on vacation. They needed a house sitter and my mom volunteered me. I was upset by this as I had other plans for my summer vacation, but after mom spent a half hour reminding me of everything that Aunt Sue had done for me and my sister, I kinda got the point.
The day before they left, I went to their house so Aunt Sue could show me what had to be done. She had it all written down so it was pretty easy, really. I had to water certain plants on certain days and to feed the dog and make sure he got fresh water and I had to take in the newspapers and the mail.
She gave me the key and told me I could drink whatever sodas were in the refrigerator and just to have fun. I don't think that she had in mind the kind of fun that I finally got into.
The first couple of days were pretty easy. I was done with the routine stuff in about 30 minutes and just left for my own activities.
But the third day, I decided to get a good look around their house. I was there lots of times before, but never by myself. I went through the house, just kinda looking at what was there to see.
I looked through her daughter Emily's room, and I saw the posters of hunky guys that she had up. She had a lot of stuffed animals and lots of basic girly things there.
I went into Sue's room and looked around there too. She and Uncle Mike are into square dancing. In fact, she makes her own outfits and makes ties and shirts for Mike to match. I guess they're pretty good because they have a bunch of ribbons and stuff for dance competitions that they were in.
Hanging over the door to her closet was one of her outfits. There was a short-sleeve blouse and a matching skirt. Also hanging there was a fluffy pink petticoat and some matching fluffy panties.
I have a thing for girls panties and I just didn't think about it. I just love borrowing my sisters and moms panties and sniffing them when I jack off. I took the pink ruffly panties and pushed them to my nose to see if I could smell anything.
They had a faint smell of the perfume that Sue usually wears, but I didn't smell pussy or anything on them. I checked out the petticoat too. It was very fluffy and soft to my hand. I really liked how it felt. I started to wonder how it must feel over a woman's legs when she's twirling around.
Well, I put everything back where I found it and went home. For some reason I was kinda horny after that. I went to my room and got into youtube and found some clips of people square dancing. I thought the skirts and petticoats looked really sexy as they move around the girls legs when they danced. I snagged a pair of my sisters used panties and jacked off to a really great cum while sniffing hers and looking at the dancers on my computer.
The next day, when I went to Sue's house, I stopped in her bedroom again after I finished the chores. I looked at her dance outfit again and something came over me. I decided I wanted to feel what it was like to have that full skirt and petticoat around my legs too.
I took off my tee shirt and my shorts and I put her skirt and her petticoat on. I tried swinging around the room like I saw on the videos. I was a little clumsy but I loved how the skirt and petticoat felt around my legs.
It wasn't very long before I started to get hard in my boxers. I reached under Sue's skirt and took them off me. The feeling of my free cock surrounded by all that fluff was amazing. I couldn't help myself. I started to jack off inside her skirt and petticoat. It was only a minute before I was shooting an amazing mess inside her petticoat. It felt amazing!
I was kinda panicked about that but I took the skirt and petticoat off quick and looked things over. There were gobs of my cum inside the pink fluff but none anywhere else. I hung up her skirt and tried to decide what to do.
I dried as much as I could with tissues but I was scared of leaving a stain. It finally hit me that I should check out the label on the thing. It said to machine wash and tumble dry cool so I figured that I could make it OK before Sue came home.
I just left it there to dry because I had to go play a soccer game. I figured that I could deal with it later.
The next day I came back and did my chores and finally went to Sue's bedroom. The petticoat was there where I left it. I was thinking about trying to use her washing machine but I was getting kinda hot and horny again just touching the petticoat.
I figured that if I was going to wash it anyway I might as well have some more fun since it wouldn't make much difference anyway. So I decided to try on the whole outfit this time and see how it felt.
I sometimes wore some of my sisters things but I never wore a whole outfit or anything. It was an amazing urge at this point. I took off all my clothes and tried on the ruffly panties first. Next, I put on the petticoat and tried to pull on the skirt. That didn't work too well so I put on the skirt first then the petticoat under it. By this time, I had another amazing erection. It felt so good I had to keep going.
I pulled her blouse on over my head and tucked it in the waistband of the skirt and looked in the mirror. I tried twirling around and I loved seeing how the skirt went way out as I turned. It didn't look quite right though. Aunt Sue is a busty lady and I was pretty flat. I took off the top and looked for her lingerie drawer. I finally found the one with her bras in it and I chose one that was pretty and had lots of lace on it.
I put the bra on and looked for something to fill the cups with. I ended up using some of Sue's socks from another drawer in her dresser. That at least filled her cups and when I put on the blouse again It looked more like Sue did when she wore the outfit.
I was feeling very horny by then. After walking around a little and enjoying the feeling of all that material around my legs, I had to lay down and do myself. I laid down on Sue's bed and felt myself all over like I feel my girlfriend when we make out.
Let me tell you that it was really turning me on! I grabbed my hard cock through the material of her skirt and petticoat and jacked off again. It was a quickie again. I couldn't believe how much this was turning me on.
After I came, feeling all of my cum inside my skirt and petticoat, I just stayed hard. I kept feeling myself all over, touching my 'tits' and feeling up under the skirt and I just had to do it some more. This time I pulled the ruffle panties down and took them off. They were made of the same stuff as the petticoat so I figured that I could wash them too. Next, I just kinda bunched up the material of the skirt and petticoat around my hard cock and rubbed it again until I shot another load.
I took off the petticoat and grabbed it up and took it and the panties down to the laundry room. I kept the skirt and blouse on. It was very nice feeling them around me as I walked around the house.
To make a long story short, I ended up finding Sue's entire collection of dance outfits down in her basement. She had dozens of dresses and skirts and tops. She had piles and piles of petticoats in every different color and different fabrics too.
I ended up trying on every petticoat and as many dresses and skirts as I could in the next two weeks. I also ended up wearing Sue's and sometimes Emily's panties and bras under those dresses. I tried wearing pantyhose and then the pettipants over them under the skirts. I also tried wearing multiple petticoats at a time.
By the time Sue and Mike and Emily came home, I had everything really neat and tidy and back in its place. They were so happy about the job I did taking care of their house, they asked me to housesit for them again and they paid me $50 extra for it.
I ended up house-sitting for them five or six times more before I left for college. I was never able to do that again, but I've taken up square dancing and I'm dating a girl who likes to dance too. She's surprised at how turned on I get by her in a pretty dance dress, but I truly make it worth her while to wear it! If she only knew what I do when she's not at home!