The story of how i began crossdressing (Part 1-3) - Sex Stories

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The story of how i began crossdressing (Part 1-3)

Date: 6/15/2016, Categories: BDSM, First Time, Mature, Author: CutiePie89, Rating: 100, Source: xHamster

Entry #1: I guess i was 17 years old and broke up with my first gf back then. barely had any sex, so was horny all the time :P I decided to look online for couples and women who would be interested in camming with me, and a mistress responded to one of my advertisements on some swinger site (i cant remember why i actually registered there) She told me she’s looking for a slave to entertain “them” Thought it was a spelling mistake (since it was german its not really much of a difference) So i agreed to be a little slut over cam (had nothing to do with crossdressing yet, i cammed a couple of times with others back then as well) Once both of us had some time, she asked me if i am ready and that i should slowly start to undress myself, she only wrote, so i couldnt see he her cam, but she saw mine. And since i was really horny and already a bit hard because the whole new mistress/sub thing was new to me back then, i did what i have been told Once i was fully naked, just a belt around my waist, she told me to slowly stroke my cock to entertain her. Once again, i did what i was told since i wanted to be a good little slave. She let me edge (always barely before cumming) for about half an hour and finally said, she’d let me cum, because its our first time and i did good so far. I actually came really hard that time and shot all over my belly an chest. She giggled,told me she was amused and that i was a good boy. She then turned on her cam, 3 ladies sitting there, drinking coffee in ... some fetish wear. I started to blush and instantly get hard again They smiled and told me that they want me to do that everyday from now on, whenever they have their teatime Entry #2: The next day, it was still in the early weeks of summer break back then, my Mistress back then told me to get ready and open my cam, and that i should wait quietly and fully naked until her 2 friends arrive… I felt really silly, sitting on my bed, naked and waiting like a toy to finally get used. She told me not to write or move, just wait there till everyone arrives. Every time i saw “mistress is writing something…” in my message window, i get more and more aroused, even if it was just a “good boy, and dont dare to get hard yet” :) After about 15 minutes, i finally got a cam invite. After accepting it, i saw the 3 ladies sitting by atable, another room than the day before, wearing lovely summer dresses, watching me on their tv, as they told me. One of the ladies started to laugh, the other one giggled about my hard on, the other one telling me how adorable i was. But immediately after that, they told me that i wasnt allowed to touch myself, but i have to maintain my hard on for their amusement. :3 Every now and then, an older, much manlier and sadly not really sexy looking crossdresser in stockings, garterbelt and panies comes in, serving them something to eat and bringing them coffee every few minutes. I actually was pretty intimidated when i first saw him. I cant really remember, but i think ...