The story behind my 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 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 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 cock 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 cock 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 cock, 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 myself, and meet them tomorrow at the same time again.

"Oh, one more thing though little boy… Have a white bra and a pair of panties from your sister ready too tomorrow…" she said and closed the cam immediately afterwards…

Entry #3:

The next day i went online and had an offline message from Mistress Sophia, which told me to be ready at a specific time, a white bra and panties ready at my side. Of course, i was sitting there, a bit shivering in anticipation of what is going to happen in a couple of minutes. At 4pm that day, Lady Very asked me via text if i was ready to entertain them again and of course i was more than ready to do so.

About 10 minutes after the agreed time they finally sent me a video request, and once the connection was established, i saw Mistress Sophia, Lady Vera and Lady Regina sitting by the same big coffee table as yesterday. All 3 of them in somewhat elegant clothes, accessories covering their necks and wrists.

"Still dressed?" was the first thing Mistress Sophia said, "thats not a very obedient slave… get naked immediately!" and of course i obeyed. i undressed out of my normal clothes, just the boxerbriefs left, but even before i could sit down, Mistress Sophia demanded: "don’t forget the pants boy, we dont want to see any clothes left on you. Except the ones we will tell you to wear for us." Lady Vera and Lady Regina giggling in the background, since they were well aware of the face what she was going to let me wear for them…

Once completely naked one of the Ladies said “so cute…” while the other one started to smile as well, seeing me completely naked, soft, trying to cover my genital area.

"I can’t remember telling you to hide anything little boy…" so i was letting go of my cock, revealing it to the 3 ladies of the other side of the screen. Lady Vera started laughing a little, Regina still smiling, Mistress Sophia looking kind of disappointed by my soft cock.

"Didnt we tell you before that your little cock should always be hard for us? You are not very obedient…" she said, i immediately apologizing, asking if i should make it hard for them. "of course slave, don’t ever show it to us soft again, unless we explicitly tell you so" 

Of course i apologized again and started touching myself in order to get it hard.

"What do you think you are doing?", Mistress Sophia asked in a very dominant way again. "Making it hard for you Mistress", i replied. "I dont think i told you, to use your hands, did i?" I apologized again, asking her what i should do instead. "lie down on your bed, hands up, holding the top side of your bed and get hard for us without touching your cock of course"

So i was lying down on my bed, hands up behind my head and trying to make my cock twitch and get it hard that way, to entertain my Mistresses. Slowly getting it harder, the Ladies could actually see it grow for them on camera. “Haha, look, its already twitching… so cute”, Lady Regina said, her head resting on both of her hands as all 3 of them carefully watch my cock grow.

I closed my eyes and tried to twitch my cock as hard as i could, to get it as big as i could make it for my Mistresses.

"thats a good boy" Lady Vera said, nipping on her coffee afterwards. Their other CD slave seem to have them served some coffee when i was closing my eyes to get hard for them.

"now, show us what you got for us" Mistress Sophia said. I reached out for the white bra and panties on my desk and showed them into the camera. "Well, it’s not much, but i guess it’ll do" Lady Regina said. "You should go ask your sister if she can borrow you some more thing, just like you are now" Mistress Sophia said. I really must have had a very shocking facial expression, since she replied "it was just a joke, relax boy…"

"Do you have some kind of collar around?" Lady Regina asked, but back then i didnt really have anything at all, so i at least showed them my wooden necklace i usually wear when in ‘boy mode’ "oh well, guess its better than nothing" Lady Regina said, stirring in her coffee.

"Put it on. and next time, you’ll see what else you can find for us, since just some panties and a bra might not be enough to satisfy us at all…" Mistress Sophia said, "but i am sure he can at least entertain us a bit with it" added Lady Vera.

Mistress Sophia demanded me to pull my foreskin back, “because i said we want you all naked” as a reason, so i pushed it back, positioning my hands behind my head again afterwards, since Lady Vera told me to do so. “Oh look, it’s slowly retracting back” Lady Regina said, all 3 Ladies immediately focusing on my cock, which kinda made me blush. Unable to suppress my cock from twitching, it immediately stood up and the foreskin retracting back over the head. 

As it seems, that was enough for at least Lady Regina to move one of her hands under the table seemingly to enjoy the entertainment i could provide for them…

"From now on, we want you to address us with "gnädige Herrinnen" (which i will try to refer as "gracious Mistresses" in my story from now ;3) from now on if you refer to all 3 of us, do you understand?" Mistress Sophia asked me. "yes, gracious Mistresses" i replied. "I couldnt hear him" Lady Vera replied. "Once again little slave. do you understand?" Mistress Sophia demanded again. "Yes, my gracious Mistresses"

"Good boy" Lady Vera replied, once again sipping on her coffee.

Mistress Sophia took a look at my cock and said: “It’s starting to get soft, slave, you know the rule right?” “I am not to present myself with a soft cock for you, mistress!” i replied. “oh oh oh, dont forget the correct addressing of your Mistresses”

"I’m sorry Madam! Of course what i wanted to say was "I am not to present myself with a soft cock for you, my gracious Mistresses!"

"Good boy" Mistress Sophia replied, actually rewarding me with calling me a good boy the first time that day.

"But for next time, you’ll get yourself some stockings or at least pantyhoses as well" she said, in order not to sound too nice to me as i thought.

"Now jerk off for us" Madam Sophia said, drinking some coffee herself, one of Lady Veras hands starting to touch herself together with me as it seems, joining Lady Regina who seemed to have a hard time not wanting to show me how much she enjoyed it already.

Lady Vera asked me if i was right handed, which i replied to with yes. “Then jerk off with your left hand”. Not knowing why i should do that, i still did start fapping with my left hand in order to behave like a good, obedient boy.

While jerking off, Lady Regina asked me, if i ever used make up before, and naturally i said no to that. Actually seeming to be surprised Lady Vera and Lady Regina mentioned that they though i actually tried it before since i seem so feminine to them. Probably because i was 17 when it all happened ;)

"Oh, its even better if you never tried it. We do like our little toys innocent you know.." Lady Regina said, a little moan at the end of the sentence.

Lady Vera then asked: “We could and probably will make a nice little girl out of you, would you like that?” I immediately started to blush, not knowing what to say. “i… i dont know, i guess, it’s ok as long as its over cam…”

"Good boy" Madam Sophia said, one hand on Lady Veras leg as it seemed. I actually mentioned that i am not really fond of taking it in the ass or getting lend to other men to cam for them :P

"Oh god no" Lady Regina immediately said, the other 2 Ladies starting to laugh in a pleasant kind of way too. "We would never let our little girl get dirty. Or well, not by others… you would exclusively be our little girl, caming for us and dressing up for us whenever we tell you to, stroking your little cock every time we want to see you cum, and play around with you whenever we feel like it" On of course, how could a little, constantly horny boy not agree to get sexually used by 3 sexy, older women, right?

"Now get the panties and wrap them around your cock slave", demanded Mistress Sophia, me of course following her command, although a little bit disappointing to actually not try them on…

"And don’t worry, this is just the warm up round", she said, letting me jerk off and cum twice, both times into the panties.

"Clean them, get some stockings or pantyhoses that fit with the bra and panties and report back to us in the evening when we tell you to" Madam Sophia said, blowing me a kiss, Lady Vera doing the same and Lady Regina looking pretty exhausted already

"See you around little girlyboy" was the last thing i could hear before she turned of the cam and went offline.

Entry #4:

coming whenever the bothering about it gets too much ;3

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