Jenny’s First Night Out – Part One

Jenny’s First Night Out


I had just turned 15 yrs old a month ago but have been dressing up for almost a year now. I buy most of my clothes in thrift shops saying they are gifts for my sister. Hard part is finding shoes my size. That and makeup I splurge my money on at the local discount store in the city.
I live in a small burb just on the outside of the city.

So going to stores where I’m not recognized is easy for me. LOL I live for the shopping part of dressing. I’m sure I don’t fool every sales clerk but they don’t care a sale is a sale. Someday I hope to go shopping when dressed.

My dad left us when I was 6 and mom and I have been fending for ourselves ever since.
I work in a local grocery store on weekends and make some money helping neighbors with yard work or other light chores after school. The real money maker of course is mom. She works as a saleswoman for a large company. Which works for me since she has to travel on occasion usually for a couple of days.

I love buying the more slutty looking outfits like denim skirts tank tops. And of course heavy eye makeup. Being thin and only 5’5” and letting my hair get long I can easily pass for a young girl when dressed.

Like any 15yr old I’ve discovered jerking off. Its way more powerful when fully dressed up. Just putting my hands in my lace panties gets me instantly hard. I imagine its a man feeling me up and running his fingers up and down my small cock.

At first I had wish my cock was bigger then its 4 inches but then I noticed it doesn’t show through my clothes. Even hard unless I wear something skin tight I can pass for a girl there too.
The more I dress up the more I think of sex as a girl and not as a guy.

My mom is out of town for three days and I’m all caught up on chores and school work.
So I’ve decided to try exploring my boy pussy. My mom’s hair brush seemed like a good choice. The handle is about 6 inches long and narrow. The only real lube I could find was a jar of Vaseline. Not a preferred choice but good enough.

I’ve dressed up in knee high nylons, pink panties, training bra, see through blouse and a knit skirt. I love my tiny heels but still need practice walking in them. After spending well over an hour playing with the war paint my face is now feminine. Or at least passable enough in a slutty way.
My hair is long for a boy but just short enough to pass for a short hair girl if combed out enough and slightly flipped.