Origins of the Sissy

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Dena
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Joined: Fri Jan 06, 2006 10:30 pm

I started wearing my sisters clothing in secret when I was about 10. I was in denial and each time I dressed up, I'd vow to never do it again. When I was 19 and bought my own lingerie for the first time was when I admitted to myself that loved it and would never want to not be a sissy.
EmpressBella
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Dena wrote:I started wearing my sisters clothing in secret when I was about 10. I was in denial and each time I dressed up, I'd vow to never do it again. When I was 19 and bought my own lingerie for the first time was when I admitted to myself that loved it and would never want to not be a sissy.
Such a fascinating story, dena!

I've found that many sissies start out with similar circumstances. Sneaking those pretty things and wearing them in secret, thrilling in both the way they look and feel, and being in a bit of denial about how "wrong" it supposedly is!

I'm glad to hear that you overcame your guilt, bought yourself something nice and are now happy with being a sissy girl! Now that you've got free reign over what you wear, what has been your favorite part of the journey so far? Have you reached your limit, or are you still exploring and expanding that wardrobe?

XOXO,
Miss Bella

http://www.phonesexfetishgirl.com
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Dena
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I can't believe I didn't reply to this thread!

I love wearing makeup, and pretty dresses. Of course, the lingerie is the best!

Once I found the right colors and styles, and make-up techniques. I found when I went out looking my best, that I liked being "read".
I haven't had any bad experiences (I've only been out several dozen times). I don't think I ever "passed" should anyone have given me a second look. Most people seemed content to play along! There was occasional laughter, in the end, laughter is good for ya.
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sissy_sindy
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my first time was at halloween. i was cupcake, probably 6-7. mum dressed me as a girl. it was nothing frilly or over the top, but i looked like a girl of my age. i had a light coloured blouse, red skirt, black tights and oxfords. she even bought me a blonde wig and gave me a light coating of make up. i was embarrassed! :oops: but i was so convincing as a girl, our neighbors wondered why i had not dressed up .... until they realized i wasn't a girl, tee hee! from that moment, i knew i wanted to dress as a girl! :D and that is why i realized that i was a sissy :!:
RitaMarie
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i wanted to dress as a girl since i was small. i started dressing as a girl after school in my early teens.
i started dating guys when dressed as a girl in high school, and i went on estrogen and started transitioning from male to female after high school, in my late teens and early 20s.
i'm mid-20s now, and have had facial feminization surgery and breast implants, and may have my sexual ressignment surgery in the not too distant future. my man will pay for it.
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_Davina_
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Just in keeping with the OP's topic, I would like to post what I remember about how I started. Looking back, that would be forty years ago now. And what a ride it's been. I suspect my story is similar to a lot of you and very different than a lot of others, but only because we are so varied as there are people. We each have our own unique story to tell and I hope you like mine.

But here's the kicker, you'll have to come back to read it, right here, in this post. A story that spans forty years can't be keyed in ten minutes and I have to get ready for work now. But like Arnold said, "I'll be back!" ;-)

Edit: And just like I said_ Here it is...

How it all started….

I wonder if anyone knows for sure just when the human brain starts thinking about sex. I would guess that a lot of folks might say that it begins with puberty but I think a lot of recent studies have shown that kids as cupcake as three years old may have tendencies to identify with gender that might not be in line with that which they were born with. I read a recent article about how some doctors advocate recognition of gender identity as a medical issue as opposed to a psychiatric issue and that treatment in one form or another begin as early as possible because it can be more harmful or distressful to wait.

In any case, I remember thinking about sex long before puberty because I can still vividly recall my first wet climax. That was a pretty spectacular night for me as I had no clue what was happening and pretty much had to learn on my own. It wasn’t that there weren’t other cupcake to turn to, as I am the middle cupcake in a cupcake with a lot of sisters. It was more that back in those days, it seemed to be a somewhat taboo subject to discuss openly so we just didn’t.

I do remember quite well how I would pilfer my cupcake’s and my mom’s unmentionables and I became so bold as to hide a bra under my regular clothes as I walked around right in front of everyone. As far as I can remember, and because I lived in another state when it began, I know I was wearing bras and panties at least two years before the first time I made my first big mess. And I also remember telling myself that night that I would never deny myself this pleasure for the rest of my life and that included the feminine undies.

I can’t say for sure when I thought about the idea of whether or not I should be or would rather be a girl but I do remember giving it considerable thought. What I remember most about that was trying to rationalize how it may be worthwhile to pretend that I could be one sex one moment and the other the next. But the most important thing I remember was that even though I was fascinated and captivated by femininity in general, I was more than happy to be a boy.

I think the easiest way to explain it is that as cupcake as I can remember, I thought of girls as the most amazing creatures in the world. As I grew, I just became more and more enthralled with them and it didn’t take me long to recognize that my sisters didn’t think being a girl was as incredible as I thought it was. I developed breast envy very cupcake but I quickly realized that it was me, as a boy, looking at girls from a boy’s perspective, that I found so intoxicating. It became very clear to me that girls, in general, (at least as far as my sisters were concerned), had no clue how much power they had over boys. I was mesmerized by the way a girl could just look at a boy and with the right look and smile, just bend him around her finger. I was in awe of this amazing ability that seemed so mystical.

One thing I knew for sure, I was not born in the wrong body. I knew very cupcake that I would never have developed this life-long fascination and desire to commit to and serve femininity had I been born a girl. Boys are so lucky because, by choice, they can give themselves to a girl, body and soul. And I had every intension of becoming a slave to the right girl.

My fantasies changed and evolved through the course of my many years and I recall a lot of various roles that I played in my imagination. Some a little darker and like I imagine all boys will, I dreamed of whisking away my Princess and just doing all the incredibly erotic and taboo things to her body that just make a guy feel so incredible. I would imagine most guys dream of burying themselves as deeply as possible in every orifice she has and depositing themselves within her. I know I had no shortage of these fantasies and I think it was here that I developed my most sincere desire to offer myself as payment in retribution for the awful ideas I had. As cupcake as I was, I distinctly remember thinking that any guy who even considered violating a Lady such asputting something in her mouth and making her keep it there until she swallowed everything, should, at the very least, be willing to accept the same treatment from her. It is the only way it could even be conceived as being fair.

I think my mom had a lot to do with my ideas of fairness and equality for females in general. To me, they were not only the most fascinating people nature ever created, they were always at least equal if not better than males at most things. I knew guys might be physically stronger but I knew very cupcake that physical strength was no match when it came to the ability of a female to reduce a male to a trembling heap of trembling flesh. I maintain that belief today and it was very cupcake that I started to believe that my life’s purpose would best be served to be in service to a female. I just knew that I could never be complete all by myself and only with the guidance of a female, would I ever be worthwhile.

So, I grew up believing I was different. Somehow, I felt like I was way off from what all my friends talked about. All their exploits and the terrible things they would say about girls just frightened me. I knew girls could hold their own and I wasn’t about to become one of their victims. I decided early on that as much as it felt good to be satisfied or complete an act of physical sex, making sure the girl I was with was satisfied first and many times was much more important than anything I wanted.

So I didn’t have a lot of girlfriends or any friends for that matter. The ones I did have were pretty close because I always confided in them and we pretty much understood each other. But like all humans, wants and needs aren’t necessarily static and marrying cupcake probably wasn’t a good idea. I guess I always believed I could make anything work but some things weren’t meant to be. But I’m pretty sure I got it right the second time around. It’s pretty cool when your wife thinks you are what she calls a total contradiction. I can be a studly guy one minute and a complete sissy the next. And she loves them both.

So what made me a sissy? Well, I don’t know for sure because I don’t know that I really am your typical sissy. I have never wanted to be a girl or even pretend to be a girl. I have never wanted to dress up and impersonate a girl. Every fantasy I have ever had that included me wearing girl’s clothing was essentially me, being a boy, being exposed as a boy who was wearing girl’s clothes. And oddly enough, that never included dressing in “regular” girl’s clothing. It was always frilly undies or a revealing bathing suit or maybe like a ballerina. But I never had any dreams of fantasies about “presenting” myself as a girl. I always envisioned myself as being obviously a boy who was being subjected to wearing girl’s clothing. And I think that makes a big difference in the process in which I see myself. The whole idea about being a sissy seems to have been the most recent evolution or incarnation because previously, I only pictured myself as a slave or a sex-slave. But I guess I came to the realization that if you are willing to do “anything” a girl demands of you, maybe that includes being a sissy.

My beginnings as a sissy include my desire to recognize and exploit my feminine nature within myself without the thought of jeopardizing my male counterpart. I don’t see any reason why a person can’t be both. I believe that if you can walk and chew gum at the same time, you can be all the guy any girl could ever wish for and her girlfriend too. If you ever run into me on the street, you would never guess I was anything but a guy you probably wouldn’t want to mess with unless you got close enough to smell that dainty perfume or maybe if you caught me bending over and saw that bit of lace sticking out of the back of my jeans. ;-)
'Just being able to dream it opens a whole new world of excitement'
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