The story of how i began crossdressing

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 cawk 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” :)