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Showing posts from 2008

i am a sissy

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The dictionary defines a sissy as an effeminate boy or man and I think that's an accurate and succinct definition of who I am. I am biologically a male, but I am not a man. I am swishy and feminine but, I am not a female. I am the in-between sex. I am an effeminate boy. I am a sissy.
A big hard penis is the symbol of masculinity; the lack of it defines me as a sissy. A pretty, wet pussy defines womanhood; the lack of it defines my sissihood. I was born a boy but can never be a man. I try to be feminine, but can never be a woman. I am neither here nor there. I am a sissy.
I don't feel like a female trapped in a male body, I don't feel like a man with an unfortunate little penis. I feel like a silly little sissy boy with a puny clitty dicklet.

panty of the month

Hope everyone had a wonderful Thanks Giving weekend. Considering the holiday season, the panty of this month is my red brief.

sissy milking

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I once spoke with a Mistress who considered sissy milking as merely a ritual to amuse herself and a way to push my sissy training much beyond my limits. 'It's not about your pleasure sissy, it's about mine. You don't deserve to stroke your clit to your silly fantasies, you can only milk it to my instructions', she said.


She prevented me from touching my clit for a few days making sure I was on the edge and ready to obey her every order to earn my release. Then, on the milking day, she had me strip naked and assume the sissy slut position, on all fours like a shameless bitch with my sissy marbles and peanut hanging obscenely between my spread knees. She called me her bitch dog and had me bark and wag my ass. She had me crawl to my bed and had me lift one leg and hump the corner of my bed while moaning like a bitch in heat. All the while laughing and satisfied with my obedience, she had me grip my little nub with just my thumb and forefinger and gently stroke it in…

sissy squirting

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The most common position for a sissy girl to play with her tiny little penis is to be on her back with either her legs straight up in the air or her legs up and open with bent knees.
I like to wear my prettiest panties, rub my clit with my palm like a girl, play with my tits, moan like a bitch, squeal in a high-pitched girlie voice that 'i am a sissy girl' and squirm in my bed until I squirt my sissy juice and soak my panties. As if the humiliation of being born a male and having to cum like a girl is not enough, my Mistress insists on continuing my humiliation by not allowing me to clean up. 'You had your fun sissy, now, we must continue your training. You need to be reminded of your submissive status. You need to be degraded for my amusement.' she says, before making me wear my sticky cum soaked wet panties until the next morning. The utter shame of wearing the messy panties, the sticky wet crotch and the dried up cum crust the next morning, all remind me that i am …

sissy squat

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For a sissy slut, even masturbating is a sissy ritual. I am not allowed to jerk off like boys, I can only milk the sissy cream out of my tiny clit in the most humiliating and feminine way possible.

The sissy squat is my most favorite humiliating sissy pose. With legs wide open and the tiny dicklet shamefully exposed, it is a great position for sissy masturbation. In this position, I am usually not allowed to touch my clit. I am only allowed to think about my shameful sissy fantasies and play with my nipples. I am only allowed to fondle my breasts, squirm, squeal and watch my sissy stick throb shamefully between my legs. My last Mistress had me suck my fingers and then use my wet fingers to pinch and twist my nipples. She reminded me that I am not a man and that I will never be one. She made me pick the pre-cum off my penis and spread it on my breasts. She laughed as I moaned and squirted all over my heels just by playing with my nipples like a true girlie slut.

sissy graffiti

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There are a variety of reasons for a sissy to be ashamed of and many more ways for a Mistress to humiliate the sissy slut. One of the interesting ways that some Mistresses have used to humiliate myself is by forcing me to use my own sissy body as a human graffiti wall and write humiliating words or phrases on it with lipstick. Most made me write my various names - 'sissy', 'pansy', 'prissy', 'slut'. Some took it a step further with 'faggot', 'fluffer', 'cocksucker' etc. Some made me write descriptions of my little penis like 'sissy clit', 'dicklet', 'little one', 'teeny'.  And, some others preferred phrases to words - 'i am a sissy slut', 'i have a little dicklet', 'i am not a boy or a girl, just a sissy' etc.
But more than any of these nasty phrases, the one word that made me hang my head in humiliation and shiver with sissy excitement was a normal, everyday word - 'gi…

halloween – after dark

I had to spend Sissy Day all alone by myself. But, that didn't prevent me from having some sissy fun. I was dressed as a sissy school girl and it didn't get long to get myself hot and bothered. Soon, the innocent looking sissy girl was stripping like a seasoned pole dancer imagining a wild crowd teasing, laughing and urging her to get naked and show off her sissy clitty and pussy. I could hear the crowd yell, 'Take it off, sissy bitch'. I could sense everyone pointing, smirking and laughing at my tiny little dicklet. I could see my Mistress watching me from the bar smiling and feeling proud as to how well she has trained me. I could feel a few hands spanking my ass as I bent over. I shivered with humiliation and excitement as I squatted on my heels, exposing myself like a shameless bitch. I stroked my sissy stick, muttering 'I am a sissy. I love being a sissy whore', over and over again, and, squirted my sissy juice all over my pretty pink heels! I only wish th…

panty of the month

White boy shorts with red cherries is the sissy panty for this month. I love the way these hug my pansy ass and I just adore the little cute bows on the sides!

sissy day

Yay! Sissy Day is here! Yes, Halloween has got to be the sissy holiday of the year. It gives an opportunity for the out and about sissies to take their cross dressing to the next level. And, it allows closet sissies like me to be more adventurous in shopping for sissy feminine items without being nervous and scared. This year, I didn't get an actual costume, but nevertheless dressed up as a slutty school girl. Which school I go to, you ask? Of course, it's the sissy school, where they teach naughty panty boys to become the best little sissy sluts they can be! Happy Halloween! Have a wonderful weekend everyone :-)

man-gina

I am so shamed, but also excited to announce that I have won the sissy man-gina contest conducted by Mistress Mindy a few weeks back! Here is an excerpt from her blog - "The first slut in knee-high socks and heels had me thinking after first look that this was a real woman and he had stole the pics off the internet - BUT upon closer look you can clearly see these pictures are of my sissy bitch with her over sized clit stuck in-between her legs."I feel humiliated at my lack of manhood, but also sissilicious about winning the contest! Thanks, Mistress Mindy!

panty of the month

Hi sissies! I am starting a 'panty of the month' feature from this month. For October it is my pretty pink boy shorts.

naughty purple dress

It started innocent enough - me prancing in my dress, feeling pretty and sissy. But, as soon as I called my Mistress, she took my prancing to the next level. I had to lift my dress and show off my cherry panties. She made me strip and go from a naughty sissy to a sissy slut!

purple dress

Just some pictures of me being a sissy, prancing around in my little purple dress. Oops! Did you see my clitty?

you know you are a sissy…

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... when your small penis is smaller than a tube of lipstick! 


... when your tiny dick is smaller than a bottle of nail polish!


... when your teeny weenie is smaller than the heels of your shoes!



... when your puny baby dinky is smaller than your thumb!



pink nails

After learning to paint your toes, the next logical thing to do is paint your finger nails. This is a little harder than painting your toes, especially painting your right hand with holding the brush in your left. Practice makes perfect and sissies have all the time in the world to perfect their sissy painting; after all, what else is a sissy going to do, go out on dates??While it's hard to master, once it is learnt, painting your finger nails can be very addictive. Don't believe me, try playing with your body with shiny, bright painted fingers. It's highly erotic. It almost feels like someone else is playing with you! The only downside is the disappointment the next morning when I have to remove the polish before heading out to work. While I have ventured out leaving my toe nails painted and hidden under my shoes and socks, I have enjoyed the sissy pleasures of polished fingers only at home.

painted toes

The cheapest way to indulge in a sissy activity is to buy a five dollar bottle of nail polish and perfect the art of painting your sissy toes. The thrill of humiliation begins the moment you enter the store to find the perfect color of nail polish. While red, pink and pastels are the sissy colors, there are a variety of different shades within those colors to keep a sissy occupied. The first few times I bought nail polish, I just grabbed the first one I could get my hands on and bought it along with a cart load of other non-sissy items. Now, I have gained the confidence to slowly take in the various colors, spend at least a few minutes comparing them, before choosing to buy one. Of course, I still choose to shop only at a drug store away from home and work, on a week day, usually around early evening when there is less of a crowd. I don't buy too many other items to hide my sissy purchase anymore; I just buy a birthday card in the hope that the person ringing the purchase might th…

pink micro skirt

With my Mistress egging me on to move ahead from being just a sissy to a slut, I finally bought this pink micro skirt. While I was used to prancing around in just my panties and heels by then, strangely I had never felt as exposed as I felt while wearing that really short skirt! To get me to overcome my shyness, my Mistress made me turn on some music and imagine being a model posing in that skirt for a catalog. After I sent her some of the pictures of my pretend photo shoot, she said that she could see the slut in me. 'Mark my words, honey', she said. 'it's only a matter of time before you become the sissy bitch that you are!' Having pleased my Mistress, I stroked my sissy stick, squirting all over my little skirt.If panties are a sissy's favorite piece of clothing, a sissy slut's favorite has got to be the mini/micro skirt.

virgin white skirt

The very first skirt I bought as I fell further into feminization was this cheap white slit skirt. I remember blushing when I first put in on; I felt like a shy virgin bride on her wedding night. But, as I posed in front of the mirror, took off my panties and extended my leg out, the slit exposed my legs, making me feel very sexy. The innocent looking skirt made me feel simple, pure and slutty all at once! I was transitioning from a sissy to a sissy bitch!

sissy girl next door

The next step in my feminization as my Mistress ordered it was to learn to curtsey, think pretty and dress like any normal girl next door would. I started wearing long skirts, cute dresses, girl style jeans. I started reading girlie magazines and watching chick flicks. When I dressed up, I felt pretty, I pranced around and thought of myself as a girl. When I called my Mistress a few weeks later and reported my progress, she was impressed. But, when I told her how I felt like a girl, she laughed hard and had me stand in front of my full length mirror. She made me curtsey, twirl, walk, prance and dance in front of the mirror and I was enjoying it. 'Strip for me girlie', she whispered. As I got down to just my panties and heels, feeling all excited, she said, 'Squeeze your boobs and play with your nipples'. As I fell silent, she said, 'What happened girl, you don't have boobies?'. 'No Mistress, I do not have any boobies'. 'That's right, girlie&…

boy shorts

Panties are most sissies' first and greatest obsession. Pretty panties are the quintessential symbol of women, the essence of femininity that every sissy aspires to. Among the many different styles of panties available, every sissy has their own personal favorite style.I love lacy bikinis, silky briefs, slutty thongs and naughty G-strings. But, my absolute favorites are those cute adorable cotton boy shorts. While the thongs make me feel sexy and slutty, ever since I graduated from weekend panty play to discarding my male underwear and wearing panties 24/7, I have fallen in love with the boy shorts. They are soft, comfortable, come in plenty of adorable designs and have enough coverage to hide and hold your naughty bits in place. They are the best choice for everyday sissy wear as there are no visible panty lines. It's ironic isn't it? Me being a boy and confessing to  loving girlie boy shorts! *giggle*

slutty shoes

After I started maintaining a baby smooth hairless body, most of my weekends were spent wearing panties, prancing around in front of the mirror, reading sissy stories, watching shemale porn and squirting my sissy juice! And, my weekdays went by looking forward to the weekends. As I was getting tired of my sissy routine, longing for someone to share my sissy thoughts with, I discovered the world of phone Mistresses. One saturday night, after a couple of glasses of wine, wearing my pretty panties, feeling sissy, lonely and horny, I called one phone Mistress and was lucky to find a gentle, understanding older Domme. Hearing me out, she advised me that the next step in my feminization was to start wearing heels. 'Honey, you can't hope to be just a sissy, you need to be a sissy slut', she told me, 'so, get yourself a pair of high heels and start practicing your slutty walk!'.Though she ordered me to go to a store and buy the shoes, I pussied out and ordered my first pai…

sissy shaving

As excited as I was when I opened my package from Victoria's Secret and slipped on my first pair of pretty pink panties, it didn't quite look right when I viewed myself in the mirror. Nevertheless that pink panty and a couple of others that I bought with it were my weekend pleasures. I changed from my boxers to panties every Saturday and wore it through the weekend, but took it off if I had to step out of my apartment. I was convinced that I was just a regular boy who just happened to like the feel of panties against his legs. Nothing harmful in wearing panties for a few hours every week, right? Pretty soon I discovered that I was not alone in my panty wearing ways. The Internet showed me the world of panty boys. As I explored the panty boy lifestyle in the web, I realized what was wrong with my panty clad butt in the mirror - my hairy legs! After a lot of hesitation, trial & error and nicks & cuts, I soon settled down in to a shaving routine. Now, I cannot imagine how…

pink panties

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After acknowledging his lack of manhood, and maintaining a girlie pit, the next important milestone in a girlie boy's transition is his first pair of panties. I am not talking about your mom's/sister's pair that you secretly tried on. It's not the one you stole from your girlfriend. It's the very first pair you bought for yourself, either by your own choice or after being ordered by a Mistress to do so.
My first pair was this cute pink cotton bikini panties from Victoria's Secret. I have bought other pairs - even sexier and sluttier ones - after this, but this pair signifies an important moment in my sissy life. The moment I slipped those panties on, I heard the door to manhood shut behind me. My pink panty signalled my entry into sissyhood. Like most sissies, I have purged a few times, but when I return to sissydom, I always start with a pair of pink panties.

smooth girlie pit

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For me, the first step towards sissification for a girlie boy is not wearing panties, but to shave off that bushy armpit hair. It is the most simple and easy thing a nancy boy can do as he explores his sissiness. A smooth girlie pit goes beyond metrosexuality. It opens the door towards feminization.

sissy clitty dicklet

Size matters. All sissies know this - especially the cuckolded ones. For most girlie boys, their little dick defines who they are - a submissive sissy. For me, my teeny weeny serves as a constant reminder as to why I can never be a real man. My tiny peepee is the symbol of my sissiness. Every sissy should know their size - not just measured by any ruler, but by a sissy ruler. My penis measures between a 'Button Dick' and a 'Gurly Bump' when soft and grows to be a 'Clitty Dicklet' when hard. If you are a sissy, how do you measure up? You can find the sissy ruler in the Sissy Zone.