This is a print version of story The story of how i began crossdressing by CutiePie89 from

The story of how i began crossdressing

This is copied from my blog, so the main updates will be there
i did think it would be nice to have it up here as well though :)

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” :)

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 he was being held in chasity under his panties, but i never actually saw it.

I asked if they would tell me who that was, and the “Head”-Mistress of them told be, that he lives with them and is already fully trained.

Once they finished their tea time, they told me, that they are very pleased with my performance, since i could manage to maintain my hard on for without touching it for about 10 more minutes.
Once the other CD finished clearing the table, they decided to relocate into the living room, watching me again, on yet another Television. :)

One of the other lovely ladies then asked me, if i think i already earned a little treat for being such an obedient and brave little playtoy…
I didnt really know what to reply, but luckily the “Head”-Mistress of the three of them told me, it’s ok to say yes, if i do it in a submissive tone, since thats how i always should act around them.

I quietly replied, that i thought i was a good boy until now, and that i think i deserved a little reward :3

The three ladies then suddenly stood up, starting to open the zippers on the back of their dressed on each other, revealing latex, pvc and leather bras, panties, stockings and garterbelts under them.

I immediately got even harder, my cawk starting to pulsate unwillingly, the two other ladies giggling at my reaction.

They sit down on a couch again and watch me on the big TV for a a few more minutes, calling me cute and adorable, before they finally allow me to touch myself. :3

But once i actually start to touch my cawk with my own had, they immediately tell me to stop. One of the ladies told me, to very slowly and gently peel back my forseskin with 2 of my finger, revealing my already red and throbing cockhead.

She tells me to maintain that pose until their slave - lets call him that - brings a pretty big, blue dildo and hands them to the head of the 3 ladyfriends.

She holds the dildo straight up and positions her finger on the top of the toy, telling me to exactly sync with her movements. She the gently hovers down the whole lenght of it, me doing the exact same thing with my cock :)

“Oh, seems like he wont be able to endure this for much longer Sophia” says one of the ladies to the head-mistress.
But all she replied was “i know” with a somewhat evil grin on her face ;3

She slowly continues to stroke the toy with only 2 fingers, me already at the edge of cumming.

I told them that i was already really really close to cumming, but none of them replied, still watching my every move.

Not be able to withstand the sweet torture any longer, i start cumming all over my own cawk, hand and belly…

The three of them quietly giggling, watching my hot cum running down my shaft and balls… :3

“Good boy…” says the one in the full PVC lingerie. “I guess its finally the time for you to learn our names little boy, since you will call us with our names from now on”

They then reveal their names one after the other, me still holding my cum covered cock with two fingers, since i wasnt allowed to let go yet.

The oldest one in leather stockings, panties and bra, about 45 years old, told me, that her name was Vera
The bit more chubby one with latex gloves told me her name to be Regina.
And the head mistresses name was Sophia.

She also told me to refer to her always as Mistress Sophia, and to the other two as Lady Regina and Lady Vera.

They then let me repeat their names a few times, making me stroke my really sensitive cock while i do that.

“I think he got it Sophia” says Lady Vera, Lady Regina mentioning how brave and obedient i was today.

Mistress Sophia tells me, that i am allowed to go clean up and dress again, and meet them tomorrow at the same time again.

“Oh, one more thing little boy… Have a white bra and a pair of panties from your s****r ready too tomorrow…” and closed the cam immediately afterwards…

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