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My first experiences

My first experiences

When I was 13 my mom had to go back to work, my parents thought I could be trusted to come home after school, and I would be safe till they would get home at 6:00 pm. Being a boy they thought I could take care of myself for a few hours. Well, all was good for a few months, and I enjoyed my time alone at home but then I started getting those sex thoughts. Started reading my mom’s dress catalogs to see the models in bras and slips. Read the National Geographics with photos of African women nude and my dad had Playboys that he thought were hidden. I thought I was just being normal for a teen boy and maybe I was but then I started doing this wearing my mom’s panties. Coming right home from school striping down and put on Mom’s panties. They felt so good and loved wearing them. Wasn’t long and one day came across a box in the attic that had some of Mom’s old panties and bras, so yes added them to my wardrobe. Also in the box were several slips and a very sexy nightie. Well, if a slip why not a dress and pantyhose mom had those stored away too. I remember the first few times wearing the bras, they felt great but looked empty. So balled-up white socks became my boobs. I would stay dressed like this till it was almost time for my parents to come home. I felt so much better in my mom’s clothes than in my boy's clothes. I started looking forward to summer vacation when I could dress as a girl all day.
So, mom would wake me up and we would chat as she got dressed, something I enjoyed not seeing my mom sexually but how she put her clothes on and her makeup. Dad always went earlier so was easy to be with Mom. After mom left, I changed into my panties and nightie, curled back in bed, and dreamt I was a girl. So, when I got up, I was that girl. Going up to the attic and my dressing area I would pick out my feminine clothes for the day. My parents had let me grow my hair long and I watched mom do her hair up, so copied that. Dad started giving me a good allowance for the chores I did. I would have to buy a few boy clothes to hide the fact I bought girl clothes. Going to the mall I bought a bikini telling the salesgirl it was a present for my sister and I asked her what one she would like so she picked out a cute one and I bought it. Was so excited about buying my first piece of woman’s clothing I couldn’t wait to get home and try it on. I was thrilled at how easy it was for me to buy it and even more thrilled at how I looked in it.
I started buying more and more clothes for my imaginary sister that I was actually becoming. I started wearing my silk undies even to school making sure it wasn’t on gym day. That is all I needed being already teased as a sissy. But I would go home strip and become that sissy I was teased about. It was very easy to learn to tuck my penis, it being just a few inches even when erect. I could stand in front of the mirror and look very feminine. At least no penis but so wanted breasts, maybe someday.
Published by bobj9876
1 year ago
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8
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Minn54
Minn54 9 months ago
As I got older I fell for shoes and sandals. Pretty little toes popping out, toe nail polish. Pink, sexy feet by the pool. I started experimenting with stockings in high school, dressing up. Started going to book stores, porn theaters and glory holes soon after. I love all kink, love exhibitionism, dressing up, group sex, very oral and eat my own milk often.

When I'm in a public place like a bookstore or theater and my toes are worshiped in stockings I get rock hard. I'll take a hit of popper and just get lost in the moment. I love being fingered in my pussy or rimmed. It's like there is a direct line from my toes to my clit and then my pussy.
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Hardcock168 10 months ago
I love hearing about how you got started , it gets me hard thinking about you dressed in your Mom’s panties when you were a young boy . I bet your little cock got erect . 
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66AndHorny
66AndHorny 10 months ago
hmmmm, yes, its arousing
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buford01 10 months ago
to bobj9876 : He saw me that way and he very much used me like the girl he saw me as. He was a fantastic teacher and lover. He did have a thing for BDSM and I was his little sub.
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bobj9876
bobj9876 Publisher 10 months ago
to tapmor : I still do also, feels so right
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bobj9876
bobj9876 Publisher 10 months ago
to buford01 : Thank you, yes had wished my Dad saw me that way
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buford01 11 months ago
That happens to so many boys. I don't remember my mom, but my dad always said I should have been born a girl and he bought me all the beautiful clothes I ever wanted.
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tapmor
tapmor 1 year ago
i know the feeling, i love to dress up...
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