Showing posts from September, 2008

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

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

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.