So when did it happen, sissy?

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EnchantrixWillow
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When did you first realize.....

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Mistress Erika
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Duchess, what a fantastic tease, your sultry voice! Wow! So enchanting, mesmerizing I almost wish I had a dick so you can turn ME into a sissy! *winks*

Also what a delicious question too! You are right, there's a point in every sissy's journey where they go from "OMG I'm being so naughty *giggles* to "I AM A SISSY! :oops: :oops: :oops: :oops: :oops: :oops: :oops: :oops: :oops: :oops: :oops: :oops: :oops: "

so gurls, the Duchess has asked you a question, and now I want to know too! Sound off!
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EnchantrixWillow
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Mistress Erika wrote: Wed Mar 08, 2023 4:02 pm Duchess, what a fantastic tease, your sultry voice! Wow! So enchanting, mesmerizing I almost wish I had a dick so you can turn ME into a sissy! *winks*

Also what a delicious question too! You are right, there's a point in every sissy's journey where they go from "OMG I'm being so naughty *giggles* to "I AM A SISSY! :oops: :oops: :oops: :oops: :oops: :oops: :oops: :oops: :oops: :oops: :oops: :oops: :oops: "

so gurls, the Duchess has asked you a question, and now I want to know too! Sound off!
Erika you know we love teasing the bois, and I am genuinely always curious, as to where the feminization world began for those who are trans and enjoy sissy play, and those who enjoy crossdressing and gender bending. Because sometimes that curiosity is just that, and sometimes it turns into something much more.. (wink)
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Mistress Erika
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Truer words have never been spoken!

Our curious minds love to know!
SissyJessika91
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This sissy is getting more and more convinced of her sissyness from hearing your voice and logic! I think I first felt/realized it at a very cupcake age when I experimented with a male friend. I suppressed it, for a long long time. A few years ago, the feelings returned, and when I started to wear my wife's panties and the day (not more than 4 months ago) when she bought me panties.... well, I cannot deny it. I am a sissy and I was 100% convinced of it then and there. But I need help to take the steps to realize it more. Please help me, please help this sissy!
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EnchantrixWillow
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SissyJessika91 wrote: Thu Mar 09, 2023 3:23 pm This sissy is getting more and more convinced of her sissyness from hearing your voice and logic! I think I first felt/realized it at a very cupcake age when I experimented with a male friend. I suppressed it, for a long long time. A few years ago, the feelings returned, and when I started to wear my wife's panties and the day (not more than 4 months ago) when she bought me panties.... well, I cannot deny it. I am a sissy and I was 100% convinced of it then and there. But I need help to take the steps to realize it more. Please help me, please help this sissy!
Jessika I have that effect, on people. You should call sometime and share your story or even better do a 2 Mistress with me and Erika, we've played together before but not nearly enough. Don't worry, we'll be gentle with you.
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Chrissy55
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I realized I was a sissy the moment I put on my very first panty. It came from my cupcake's collection I was very fortunate because we wore the same size so she never got suspicious about anyone wearing her unmentionables because I didn't stretch them out.

Another positive aspect of my luck was my cupcake had a huge panty collection ranging from practical everyday wear skimpy string bikinis (my favorite type of panty) elegant satin lingerie for formal wear, ending with crotchless panties which made her a woman who was sexual and confident in her sexuality.

When I saw myself in the mirror wearing her deep pink silk bikini panties the look, the fit and how they felt cradling my penis I knew that I was meant to dress this way.

Once this happened I immediately began to crave and yearn for a cock to serve my mouth ached for a dick and I knew this was not going to be a stage I was going through or this was just a phase I knew it would be a lifetime commitment!

So I committed to this lifestyle and preparing for my anal virginity to be taken my flower is ready to bloom!
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Jamie Michelle
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Chrissy55 wrote: Mon May 01, 2023 6:50 am I realized I was a sissy the moment I put on my very first panty. It came from my cupcake's collection I was very fortunate because we wore the same size so she never got suspicious about anyone wearing her unmentionables because I didn't stretch them out.

Another positive aspect of my luck was my cupcake had a huge panty collection ranging from practical everyday wear skimpy string bikinis (my favorite type of panty) elegant satin lingerie for formal wear, ending with crotchless panties which made her a woman who was sexual and confident in her sexuality.

When I saw myself in the mirror wearing her deep pink silk bikini panties the look, the fit and how they felt cradling my penis I knew that I was meant to dress this way.

Once this happened I immediately began to crave and yearn for a cock to serve my mouth ached for a dick and I knew this was not going to be a stage I was going through or this was just a phase I knew it would be a lifetime commitment!

So I committed to this lifestyle and preparing for my anal virginity to be taken my flower is ready to bloom!
Thanks for sharing, Chrissy!
Boys will be girls.

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Author (under a nom de plume) of "Jesus Is an Anarchist", Dec. 4, 2011, http://ssrn.com/abstract=1337761

Theophysics, http://theophysics.freevar.com , http://theophysics.epizy.com
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Dena
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I was ALWAYS a sissy! I tried to deny it and fit in with the boys, that just did not happen.
It took me a long time to accept it.
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Jamie Michelle
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Dena wrote: Tue Jun 13, 2023 11:44 am I was ALWAYS a sissy! I tried to deny it and fit in with the boys, that just did not happen.
It took me a long time to accept it.
I can certainly relate, Dena!
Boys will be girls.

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Author (under a nom de plume) of "Jesus Is an Anarchist", Dec. 4, 2011, http://ssrn.com/abstract=1337761

Theophysics, http://theophysics.freevar.com , http://theophysics.epizy.com
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Chrissy55
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Well it first happened when a saw a pair of my cupcake's panties they were something I didn't see in the laundry these panties were very special and they have to be hand washed that's how dainty and delicate they were I call them fuck and suck panties they show off a woman's pussy , ass and all of her attributes also they are made to be worn when you want to fuck dick and suck dick. The second I put them on at 14 years old I knew my days as a male were numbered!
When I saw myself in the mirror I knew I was heading into cocksucker status
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Jamie Michelle
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EnchantrixWillow wrote: Tue Mar 07, 2023 5:51 am When did you first realize.....

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Thank you for this recording, Duchess Willow! To answer the question posed in your audio, I relate realizing when I was a sissy in my following posts (the posts have the same thread-title even though they're actually different threads):

* Jamie Michelle, "Re: When did you discover you were a sissy?", May 1, 2016, viewtopic.php?p=75860#p75860 .

* Jamie Michelle, "Re: When did you discover you were a sissy?", June 1 and 28, 2018, viewtopic.php?p=82120#p82120 .
Boys will be girls.

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Author (under a nom de plume) of "Jesus Is an Anarchist", Dec. 4, 2011, http://ssrn.com/abstract=1337761

Theophysics, http://theophysics.freevar.com , http://theophysics.epizy.com
sirtheocean
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Wow this was really sexy and hit close to home. I'm still not 100% sure I'm a sissy but I've definitely recently started to enjoy the feeling of being emasculated. That humiliation any guy feels for not being 'man enough' has started to cross into my sexual desires.

I was checking out a hot gym girl's instagram and saw a pic with her boyfriend grabbing her ass. This guy was just a huge muscle bound stud, the kind you can't compete with, and I thought 'wow now there's a real man'. I looked for a few more pics with him in when I was suddenly like 'wait, am I jealous of him or of her 🙈'.

These feelings of not being 'man enough' led to me trying on a pair of my girlfriends panties and I could not believe how my butt looked in them. It could have been a girl's butt! It was one thing to feel that I wasn't a man but to feel sexy like a girl was a whole new level of emasculation. So that's maybe when it happened and I thought 'omg am I actually a sissy?'
Startup sissy trading in his CK boxers for thongs one pair at a time :lol:
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EnchantrixRachel
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sirtheocean wrote: Sat Oct 28, 2023 1:31 pm Wow this was really sexy and hit close to home. I'm still not 100% sure I'm a sissy but I've definitely recently started to enjoy the feeling of being emasculated. That humiliation any guy feels for not being 'man enough' has started to cross into my sexual desires.

I was checking out a hot gym girl's instagram and saw a pic with her boyfriend grabbing her ass. This guy was just a huge muscle bound stud, the kind you can't compete with, and I thought 'wow now there's a real man'. I looked for a few more pics with him in when I was suddenly like 'wait, am I jealous of him or of her 🙈'.

These feelings of not being 'man enough' led to me trying on a pair of my girlfriends panties and I could not believe how my butt looked in them. It could have been a girl's butt! It was one thing to feel that I wasn't a man but to feel sexy like a girl was a whole new level of emasculation. So that's maybe when it happened and I thought 'omg am I actually a sissy?'

Oh, panties have been the lightbulb moment for many a gurl, sirtheocean!

I also like that moment of confusion you experienced regarding which one of them you were jealous of!

Yes, Duchess Willow is masterful at helping you tease out those details and memories, isn't She?
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EnchantrixWillow
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sirtheocean wrote: Sat Oct 28, 2023 1:31 pm Wow this was really sexy and hit close to home. I'm still not 100% sure I'm a sissy but I've definitely recently started to enjoy the feeling of being emasculated. That humiliation any guy feels for not being 'man enough' has started to cross into my sexual desires.

I was checking out a hot gym girl's instagram and saw a pic with her boyfriend grabbing her ass. This guy was just a huge muscle bound stud, the kind you can't compete with, and I thought 'wow now there's a real man'. I looked for a few more pics with him in when I was suddenly like 'wait, am I jealous of him or of her 🙈'.

These feelings of not being 'man enough' led to me trying on a pair of my girlfriends panties and I could not believe how my butt looked in them. It could have been a girl's butt! It was one thing to feel that I wasn't a man but to feel sexy like a girl was a whole new level of emasculation. So that's maybe when it happened and I thought 'omg am I actually a sissy?'
It sounds like you opened the sissy pandora's box with the instagram, and then trying on panties and realizing you looked good in them. Most of the callers that I talk to that are into feminization, have admitted to feeling that mix of humiliation and excitement, to wearing panties and women's clothing. Thank you for sharing 😊
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