from Skyler

Dear Auntie Helga,

Here is my story of how I came to realize that I like being petticoated and respect women greatly for it. I actually wish I was born a female instead of male. I guess I was just unlucky. It's really isn't a sexual fetish for me either because I have been struggling with wanting be a female ever since I was very young. I am single though, but I'm not really the type of male women find attractive. I am small and not big and muscular. If I did find a woman I would treat her like queen. They say males are the dominant sex, but I don't believe it to be true. Women truly hold more unseen power than men do. Any ways here is my story...

My petticoating starts with my sister who is 2.5 years older than me. She is a very confident and a successful woman. I look up to her a lot. Some might say it's jealousy but I'm not really mad at her success, on the contrary quite proud of her. I just wish I was her or her little sister instead of her little brother. I believe she wishes I was her little sister too, but she has never hated me because I am a boy.

When we were younger, my sister was 12 and I was 9 about to turn 10. My parent let her look after us while they were at work because she was very mature. My sister came up to me and asked if I would be her little sister for the day. As any self respecting boy would do I laughed and I told her nooooo!. But little did she know that I truly wanted to. She kept on begging me, telling me it would be so much fun. Finally I gave in, not that I was truly fighting it in the inside. I rolled my eyes and told her "fine I'll do it" in a sighing annoyed like voice. She jumped up and down in joy and screamed "yay!, thank you so much!"

She took me be the hand and told me "Come on Skyler". I stopped and ask her "Skyler?" She said yep that's going to be your name as my little sister. I told her "oh okay!" But didn't act excited. I thought it was a very pretty name though and loved it since my older sister had given it to me. We went to her room, and I was surprised that she already had everything laid out on her bed. One of her old pageant dresses (like I said earlier I'm a smaller male so it fit me), a matching pair of shoes, a matching pair of panties and training bra, one of her play wigs, and her pageant tiara. I asked her "do I have to put all of that on?" She said "yes" I asked her "even the panties? and bra?" She said "yes, all little pretty girls need matching underwear. She than told me to put the dress , panties, bra, and shoes on and come back and she will put on the wig the tiara and makeup. I asked "make up?!" she said "yes all little pretty girls wear makeup" I said "ugh whatever!", still acting like this all bothered me and was an annoyance. I took the dress, panties, and training bra and went to change.

I went to change. I got all my clothes off and started to put on the panties and bra. I put on the panties, I always wondered what girl underwear felt like and was truly happy that I was about to find out. I put them on and couldn't believe how comfortable they were, they felt so right and I loved them. I started to put the training bra on but couldn't, so I called out to my sister to "help, that I couldn't get this stupid thing on." Still acting like I hated all this. She told me to just bring everything back in her room and she will help me finish putting everything else on. So I came back in, and was a little shy because I was just in panties. When my sister saw me she said "aww those are so cute!" She then told me to hand her the bra and turn around. She put it on and then popped the strap on my back. I said "ouch!!!, what was that for?!" My sister answered "I just wanted to show how bad that hurts when boys go around popping girls bras." I told her "oh okay, I definitely won't be doing that, it really hurt!" She then told me to stand up and raise my arms, she took the dress and slipped on over my head and than zipped it up in the back. I looked in the mirror and "said I look ridiculous!" my sister replied "noo you look so cute!" I agreed with her but would not admit it. The dress was very pretty it was a pink pageant type dress and it came to my knees. My sister then told me to sit down so she can put the shoes on me. Oh she said "I almost forgot the socks!" so she got some socks out. They were white and frilly, typical girl socks. She put them on me, and I have to admit that even girls socks are more comfortable than boy socks. She than put the shoes on, they were matching pink shoes. Not really sure what kind they were but they were really comfortable. She then told me to "stand up in front of the mirror." So I did as I was told. She then combed my hair back and pinned it.

My hair was boy long not girl long, but she still had to pin it back. She then put the wig on and fixed it. The wig color was light brown so it matched my hair color nicely and you couldn't tell if it was a wig or not. She then put the tiara on and fixed it just right. My sister then said "Oh my goshh your are so precious, Skyler!!" I replied like any boy would and said "no I'm not! I look stupid!" But in reality I loved the way I looked and truly wish I was the girl that was staring back at me in the mirror. She then said "time for make up!" I said "do we have to really do the makeup?!" She said "yes, all pretty girls wear makeup!" She told me to sit back on the bed so I did. She then put the make up on me, and made me all pretty. She told me to look in the mirror and I was shock at what I saw. I thought I looked like a girl without the makeup on, but now I really really did look like a girl. At this point I was so jealous of the girl in the mirror and wanted to be her so bad. She asked me "well what do you think?" I just looked in the mirror sighed and said "whatever." She laughed a little bit and said "you are too cute, Skyler!" She took my hand and told me come lets play.

We went into the kitchen and played tea time and other girl games. I didn't act like it, but I had soo much fun that day. I played my sister's sister for a couple of weeks, but never acted like I liked doing it. She would have start begging me each time before I would tell her yes. But truly she didn't have to really beg me at all because I really liked being her little sister. Unfortunately one day our dad came in early. Now my dad was a real good man and a great dad, never beat us for anything, but was very stout about discipline when it came to getting on to us. He came in and was shocked, asked my sister "what is this?!" She couldn't really get any words out and was stuttering for them. He yelled "get that stuff off him now!" and then yelled at me "I can't believe you will let your sister do this to you!" I was stuttering for words myself, "bbbuuutt I didn't". He said "he didn't care who was at fault that we were both grounded and both equally at blame!" He then said "girls should be girls and boys should be boys!!" Thus ended the greatest couple of weeks of my life.

I'm 23 now and my sister is 26 and we really haven't talked about that time ever since. I would give anything to actually be her little sister, Skyler, though. But unfortunately I was born a male in this lifetime, perhaps next lifetime I will be lucky and be born a female.


Thank you for your letter Skyler. At least you were able to experience being a girl for awhile. Now that you are an adult you can dress up anytime you wish. I know many readers would love to have had a sister that did this with them. Treasure those memories Skyler.

Auntie Helga

Return to Index
Letter 9