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

    exactly what she was doing, trying to give her little cousin a hard on? Ultimately I don't care! it was hot. At this point, puberty was fully on. I was grinding out loads almost every day. I had stolen Playboys and a couple of Penthouses that I wore the pages out of. I was always drawn to the pics of the ladies who had some lingerie on. It was here I first learned about the different types on lingerie. Thongs and G-strings were just starting to make appearances, but body suits, slips, stockings, gloves, and see through nylon bras and panties and string bikinis are the items that I recall. My prize magazine was an early 1980’s Playboy Lingerie Special. I loved everything in there, BUT I still hadn’t made the connection yet to actually putting on the lingerie myself. I recall around this time and older male cousin saying, “I love the pics in those mags, but I really like a lady with a bit of clothing on” referring to lingerie. I guess it runs in the bl**d! As I had gotten older, I had more responsibilities around the house, this meant I had to start taking my turn doing the laundry and then BANG there it was, the confluence of all my preparing! My s****r’s panties! Nirvana! She is one and half years older than me, but she skipped a grade so she was 3 years ahead in school and I guess girls of her year have to have a lot of panties. And they were magnificent. I had to handle them, folding them etc. I would estimate, in later years, she had over 50 pairs in her draw (and I wore ...
    all of them). Apparently her favorites, which became mine, where the silk floral print string bikinis. She had at least 6 pairs of these. You can find these under “vintage” style panties on line at EBay now. It may have been the first time I did the wash or I may have waited for a while, but at some point the black and red ones were the first ones I slid on. Down in the basement, they were fresh off the line and I was alone in the house. I remember quickly taking off my pants and boys underwear and hurriedly pulling those soft yet tight panties up my skinny legs. It took no time at all to adjust my balls and dick into the front, I could not believe they fit given these were ladies panties! (Now of course I realize the style back then was a high waist cut, which created a good sized front panel on the pantie. Thank goodness!) I gave my ass a quick feel and the front a quick rub. I remember just as quickly pulling them off getting redressed and sitting there wondering what had happened. Yes I was confused, but I was also hard as a rock. I left them there, went to my room and jerked off (I had figured it out by now) twice! I thought about what I had done for days, always making me hard, but confused. Then I remembered a story I had read in a Playboy letter, about a man wearing ladies undergarments. Once I had put that all together in my mind, that men can in fact wear ladies panties, it has been done before so it must be ok at some level, I allowed myself to explore. And then the ...
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