Sissy Boy
I am a 16 year old boy, and I am a sissy boy, I wax all my body hair off, so the only hair I have is my eyebrows and the hair on top of head, witch is long enough to wear in a pony tail or in pig tails.
I started when I was 14 wearing panties, I was nervous when I went into wal mart and purchased a package of panties, but after a while I found out no one cared that I was buying panties, I then bought a couple of short night gowns to sleep in, and then some girls pjs. last Christmas eve I slept in a long night gown with a reindeer on the front and wore panties that had candy canes on it. I put on boy clothes before I went down to open presents, but kept the panties on.
This year at the start of summer vacation I bought a dress, I think it is called a sun dress, and some sandals, and after mom went to work I put my hair in pig tales and put on my dress and sandals and went to work cleaning the house, I even swept off the patio in my dress, forgetting their is a house behind our property. Well after the house was cleaned I went up to my room and took off my dress and sandals and put on shorts a a shirt and took my hair out of the pig tails.
Soon after the door bell rang, and it was the lady who lives in the house behind ours, I opened the door and and she said, "You looked cuter in your pig tails deer." I was speechless, she smiled and said, "Put your dress back on and we can talk." She then showed me a picture on her phone of me in my dress sweeping off the patio.
We went up to my room, I stripped off to my panties, she said, "Oh lovely, you wear panties to, is that the only kind of underpants you wear?"
I blushed and said, "Yes, usually." then added, "I do my own laundry so mom doesn't know."
After I put my dress on she asked me a lot about when clothes I had, I showed her my panties and sleepwear and said that I only had the one dress.
She asked if I wished I could live dressed as a girl full time, I admitted I did.
She then said I would come over and clean her house, dressed as a girl, she would buy me more girl's clothes. I said I would do it.
She braided my pigtails and we went through the back yard to her house, we then got in her car and she took me to a few stores where she got me some girl's shorts and tops, skirts and a few dresses and even some swimsuits, 2 one piece suits and 3 bikinis, we then went back to her place when I did some cleaning before heading back home, I got home just before mom did, or I would have had some explaining to do.
She wants me to come to her house to clean dressed as a girl, she says I should tell my mom I like to dress as a girl all the time, but I am too nervous to do that.
If I come to her house dressed as a girl I can get right to cleaning, or we go on when ever trip she had planed for us. If I show up dressed as a boy then she spanks me, bare bottom, and she spanks hard, with a wooden hairbrush, and I have to clean wearing only my panties, and if I want to go home dressed as a boy then I get spanked before I go.
She has taken me to the beach or a water park many time, we went to the zoo a couple of times, and I do enjoy going out in public dressed like a girl, she says I should dress full time like a girl and start to date boys.
I don't know if I could date a boy who knows I am a boy who dresses as a girl, but on day at the beach I did go away with a boy I met and sucked his cock, and I will admit I liked it and wouldn't mind being a girl sucking her boyfriend's cock and swallowing his cum.
I wish my mom knew this part of me, even spanking me if I did something naughty, but then I think what if she doesn't understand.
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