I think that being a sissy is obviously a niche genre that involves many degrees of androgyny and mix bag of sexual orientation which are not mutually exclusive. Being a ‘sissy’ to me is cross-dressing to the fullest potential I’m able to practice and achieve. It is a pseudo-effeminate approach for those who long to feel sexy in countless outfits, shoes and accessories without actually being transgender.

How My Interest In Being A Sissy Started
The interest sparked for me in my early teens. I imagine it began the same way it did for many, with a pair of panties. In this case, I actually worked up the nerve to purchase a pair of my own out of curiosity and it was all downhill from there.

Challenges I Faced Initially
The shame and guilt early on took a long time to overcome. I spent a small fortune on clothing and would purge the wardrobe on many occasions in a failed attempt to eradicate the urge; need to dress and doll up.
Eventually, I came to terms with my “affliction” and allowed my collection to flourish over the years. Life is far too short to have to let myself only maintain a secret interest without ever indulging and truly knowing yourself.

Common Misconceptions About Sissies
In my opinion, some of the sub-genres of being a sissy involve those who never “graduated” from the panty-boy stage. The many who are too lazy to put in the effort beyond a sexual interest tend to give it worse a reputation than it already has.
I can’t say we clearly aren’t all confused as to the why or the how the attraction began but we’re all inherently flawed somehow. So, forget the haters, if anything is worth doing, it’s worth doing right.

Important Aspects When Learning To Be A Sissy
I think that whatever your ‘thing’ is, that you should try and grow in that direction within reason of course. The milestones involved are different for everyone I’m sure but the most notably difficult part is makeup which the internet can be a wealth of information when learning how to do the most important step.
It’s the difference between not being taken seriously as an unshaven man or looking presentable as a woman. I’ve found that how well you’re perceived or accepted is directly relative to your sincerity and efforts.
Sissy Shawna – I am a submissive pansexual sissy crossdresser who enjoys being humiliated and degraded by Dominant women and will suck a golf ball through a garden hose for Alpha men.
Follow Sissy Shawna on
Twitter: @sissyfag1984
KiK: ShawnaSissy
Email: Sissy.shawna@yahoo.com
Images courtesy of Jonalyn
Like to be featured on SimplySxy? Drop us an email at editorial@SimplySxy.com!


You need to adopt ultra-feminine behaviour. To help with this, I usually make my girls watch films based on the lives of transvestites first. A quick search on Google will pull up quite a few. This is just so you can see what it generally is like. Keeping a diary also helps by keeping those emotions at the forefront of your mind. Women are generally more emotional than men so this conditions the mind to become more feminine. It also helps to choose ‘womanly’ activities over the more stereotypical male ones. Maybe take up a form of dancing, or fashion design or baking is another popular option. It is also considered wise to remain in chastity whilst training. A number of devices can be purchased if this is required.
3. Beauty
had brilliant fashion sense when they came to me. Others, sadly, did not and required much effort on my part to become what they are today. It is good to start with the undergarments. I think some nice pieces of lingerie such as satin panties or a lace bra really make you feel feminine. But ultimately, you are going to want to compact the panties and fill the bras. Breastforms are something you wear to shape your bras and provide breasts without the need for surgery. They also come in different sizes which is very useful. Vee strings are something I learnt about more recently but basically, they enable the wearer to tuck away any ‘unladylike’ parts whilst allowing the user to pee sitting down like a lady. Some of my girls have even employed the use of a waist trainer to accentuate that desired feminine waist. Ultimately you want to choose the best style for your body shape. Styling for your body shape takes time, practice and lots of effort. Shoes are the ultimate feminine weapon. The beauty of a high-heel never goes unnoticed but again, walking in these can take time, practice and effort. This is something you definitely have to practice. I advise to start with a low heel and work your way up to the desired height.