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Beginnings
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While here I am, totally in the mood, dressed up, and a dildo up my ass. Now is the perfect opportunity to write the first signs on this behavior and the moment that actually started off this little escapade.
So lets start with childhood. At first there was nothing worth mentioning, but just as a fun fact, that the first acts of crossdressing started accidentally as a kid, when finding my mothers pantyhose, and wearing them for my little role playing adventure i had in my head. It was not even sexual in nature, i just wore them at that time because they were "cool". But very soon afterwards, after finishing my adventure and returning the pantyhose to its place, my mother just scolded me slightly not for crossdressing, but for making some runs in the hose(because i did not know how to put them on correctly). As it was no big deal, and i kinda grew out of it very soon.
Then my first real experimentation came at late highschool. I had a normal highschool life. Friends , girlfriends, nothing out of the usual. When at the time i had a sort of lingerie and stocking fetish. as i liked elegantly dressed women. not wanting to be one. After our family moved to another town, we would sometimes go back to the old house to check if we forgot something. And after such visits, i came alone and dug through the stuff that were left behind, and found a alluringly looking garter belt, a nighty and some stockings. not sure how or why the were left there, but it looked very interesting that such specific things would be left behind, and my puberty filled mind ran wild. So i tried them on to see how it felt like to be sexy like the women i masturbated to all this time. Needless to say, it was a thrill but not perfect. As i soon found out that not all legs look great in stockings, especially hairy, unshaven legs. But that did not stop me, and took them with me, and when i was alone, i would try them on, and have fun. As jerking off was fun, i also tried to see how it would be to put a finger in my but, as trying to simulate the pleasure that women likely have. Also not the ideal first experience, but later on i continued to play with my hole a bit more, and it was enjoyable. But very soon, i kinda lost interest, as life goes on, college came, other things come up, and i just forgot about it and abandoned it....until...
Later on in collage, i was going home alone ,drunk from a pub with friends, taking the usual route to get home. All of a sudden, i saw a woman's sports bra just hanging from a branch of a bush i usually pass by. Being drunk, i thought i would be funny to take it home with me. I am not even very attracted to bras, but just taking it with me home, and trying it on lit up a fire that had died out long ago...and it all went down hill from there...
to be continued...
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Posted on : Jan 25, 2021
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