1. How I started Cross Dressing and other first times


    Date: 7/22/2015, Categories: Fetish, First Time, Taboo, Author: pantiesdave, Rating: 100, Source: xHamster

    blue applique over silvery grey. The material was stretchy but tight! I love that feel! It came down over my knees and has built in cups and thicker maybe 1/2inch straps. I loved it, but did not know why. When they put it on me, I clearly remember feeling great and wanting to show off. We did a dry run of the “show” and someone decided to put make up on me. I was young so I did not object. I think I have a memory of looking in a mirror and not being upset with what I saw. So we went out to do the actual show, everything went fine, the adults were pleased with our efforts. Then things got weird. I guess I did not want to get out of the dress because I clearly remember my Dad getting mad and saying “get him out of that”, and then storming off. When my Dad said to do something, it got done . And that is the end of that memory. But every time I pass buy a vintage clothing store I try to do in and find something similar, no luck so far! The next memory is what I have always said was the true cause of my cross-dressing. It was right around puberty, so I must have been about twelve or thirteen I guess. Now I am sure there were many, less inpactful, incidences that occurred to me between the dress up play at six and thirteen, maybe glimpse of panties and bras here and there, or some summer swim suit things, but nothing stands out. What does stand out, is the red cotton underpants! Or were they panties? I shall explain. My Mom did the laundry. I have an older s****r. One day, as I ...
    was getting ready for school, I reached into the draw for some underwear and pulled out a pair of plain red cotton…underthings. I know now they were bikini cut, with seams on the hips, no fly, no tags, but not something that you would look at and say immediately, those are girls. They were just plain. Kind of cheap looking, like a dollar store pair, which would not be unusual in my house as Mom was a great penny pincher. Being prepubescent, I had no trouble fitting into them. In fact, as I still don’t know if they were males or females, I’ll bet any boy of that age would have fit. So I put them on and WOW did I like them! They were tight! Super snug on the front and grabbed my ass nicely. I loved them! I made sure from that point on, after the laundry was done, they made their way into my pile, to be put into my drawer where I wore them immediately. No one made a fuss, no one moved them to my s****r’s room, so I fell in love with the feeling of pressure on my cock and balls. It was right around here when I had my first orgasm as well. My friend across the street and I had been experimenting, as boys do. We touched and sucked each other’s’ penises, put our fingers in each other’s butts, harmless stuff, but no cumming. In fact, I remember one time when we were “crossing steams” in the toilet my friend called the bubbles that came up in the water cum! I laugh about that a lot now. I knew all about jerking off, but my penis was either too sensitive or I did not use enough lube to ...
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