13 Reasons Why There’s Never Been a Better Time To Be a Sissy

become who you desire
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Reason #1 – Become Who You Desire

I don’t know about you but, as a sissy, I’ve always been attracted to the ultra-feminine, girly-girl type of girl—women who spend extra effort to express their femininity and sexiness.

In other words, I have a penchant for high heels, long lashes and longer nails.

From my admittedly not-so-lofty vantage point, I have observed that most genetic girls—in the USA anyway—aren’t really interested in portraying the super-feminine image that I prefer.

To expand on that line of thought; I get a strong sense that many cis girls today tend to take their femininity for granted.

That has led me to feel frustrated and disillusioned because…

I don’t want to be with a girl who wants to wear jeans, tennis shoes and a sweat shirt all the time—and is not into wearing makeup!

So what’s a sissy like me to do?

Convincing someone else to look and dress the way I prefer is a futile task—at best—that left me feeling more frustrated than Cinderella at the stroke of midnight.

I mean, we can’t expect people to be anyone other than who they really are… right?

Once I came to that—not-so-obvious-at-the-time—realization, I saw that I was approaching this situation with a flawed mindset.

The only thing we really have absolute control over is ourselves.

So what better way to bring long lashes, longer nails and higher heels into my life—on a consistent basis—but to…

Become the girl that I desired!

What a feeling of freedom I experienced when I decided to thoroughly embrace my femininity and take FULL responsibility for satisfying my feminine wants, needs and desires.

Now, I no longer need someone else to fulfill my fascination with femininity—I can do it all myself…

By becoming the woman of my dreams!

Sure, I may wind up meeting a woman—or perhaps another sissy—that proves to be a perfect match for me.

But until then, I’ll be happy and content to continue to delve deeper into my feminization and sissification activities by being…

The best damn sissy that I can possibly be.

So yeah, reason #1 as to why there’s never been a better time to be a sissy is that…

You can become the girl of your dreams!

I know… there’s a part of you that may be reluctant—and even petrified—to give up your manhood.

That’s understandable and completely normal but, it’s a lot easier to let go of your male ego once you realize that…

Reason #2 – Masculinity is Highly Overrated!

sissify the male

Back in the day, a popular saying among women—in western civilization anyway—was “it’s a man’s world.” Perhaps that’s still true to some extent but…

“The Times They Are a Changin’.”

No doubt that ‘modern man’ has accomplished much over the past few centuries. But there has been a flip-side to this—in my mind—overly-aggressive mentality, such as…

  • Wars
  • Hate
  • Greed
  • Stress
  • Genocide
  • Anxiousness
  • Over-controlling
  • Compromised health and longevity

I’m sure you can think of more examples where the unbridled expression of the almighty male ego has done maybe more harm than good.

People in general—and sissies specifically—are coming to the realization that the world would be a happier, more peaceful place with less male ego and more feminine understanding and compassion.

And that’s where you come in dear sissy.

What better way to be part of the shift that’s taking place and help make the earth a more mindful, peaceful and loving place to live than to…

Become a woman yourself!

But not just any woman—but a submissive one—a sissy.

There is still WAY too many mindless male egos running rampant; generating unnecessary chaos, fear and pain.

It’s up to us sissies to set an example for the world and show that there is a more kindhearted and gracious way to live.

That it’s entirely OK—indeed, preferred—to be a giver rather than a taker.

The time is right to place the male ego, and all of it’s obnoxious, distasteful and nasty characteristics under wraps.

It’s time for us sissies to disseminate a much-needed healthier and harmonious vibration into the universe.

And it’s so much easier now-a-days to openly—and fearlessly—express our femininity that it ever used to be.

Reason #3 – We Live in a More Tolerant and Accepting Social Climate

crossdressing gone mainstream

When it comes to sexuality, society is much more sympathetic and supportive of someone—like you and me—who chooses to identify with the female gender.

I don’t think it would be too audacious of me to state that crossdressing—and even it’s less-illustrious step-sister, sissification—has not-so-quietly made its move into the mainstream of cultural consciousness.

As you’re probably well aware, things haven’t always been this way… especially in western society.

There are most likely cultures that are less tolerant of sissies than the one you happen to live in. Conversely there are societies that are more sympathetic to—and even embrace—the LGBT movement.

The world, as a whole, has progressed to the point where it is no longer such a huge deal to venture out of the closet—if you want to—and prance through the mall listening to the intoxicating sound of your high heels clickity-clicking down the concourse.

And you can do this without worrying about someone going ‘medieval’ on you.

Sure, you’re gonna get the odd look here-and-there, but that’s getting less prevalent too—unless some 5 year old kid ‘clocks’ you.

Anyways, please don’t take this more accepting climate—one that allows you to be who you want to be—for granted. Be eternally grateful that it’s so much easier now-a-days to express your sissiness, more-or-less, openly.

Hell, even if you’d prefer to hide in your hamper rather than take a single step out in public, it’s still easier these days to come out to friends and family—depending, of course, who your friends and family are.

Notice that I said ‘easier’… not necessarily easy.

But if you were looking for a very good reason to be a sissy, the truth is that there’s NEVER been a better time in history than right now.

Today there’s absolutely nothing holding you back—except maybe you?

Reason #4 – Earrings, Shaving and Manicures

sissy manicured nails

Let’s expand further on how crossdressing and sissification has infiltrated the mainstream consciousness of our society.

Let’s use earrings on males for our initial example. I originally got my left ear pierced back in 1996. In the spirit of symmetry—and to subtly express my inner-feminine-self—I followed up with having my right ear done in 1997.

Shortly afterwards, I asked a girl out on a date that I had met at the gym. On that first date, she felt compelled to remark that it was a BIG deal for a guy—that lived in Reno anyway—to have both of his ears pierced.

23 years later it’s now a completely commonplace and a totally accepted occurrence almost anywhere in the modern world… I think?

Same with shaving. Back during that same time period I was competing in triathlons and it was very common for the guys to shave their legs because of the biking part of the sport.

I thought my legs looked so damn good smoothly shaved that I never stopped!

Now-a-days, although certainly not prevalent, It’s not unusual at all for a guy to shave his entire body—which I’ve been doing for five or six years now.

Having a hairless body, an activity formerly reserved for swimmers and body-builder-types, is now available to all of us guys—and no one seems to bat an eyelash.

How about manicures? Men have been getting their nails done for many years now. They may not be flaunting them in quite the feminine fashion as they might like, but still.

The point is… as your sissy aspirations escalate, it’s perfectly acceptable today to subtly—or maybe not so subtly—intensify you sissification process by way of the above methods.

You’re not gonna get much flack over getting your ears pierced. Possibly a little here-and-there but… even though you may fear that people’s reactions might be fatal to your fragile, feminine psyche—any judgments tossed your way will turn out to be less than a flesh wound.

Shaving your entire body? C’mon, hardly anyone will notice, much less care.

Having nicely manicured nails with clear or matte polish will make you feel super-feminine. Only girls will tend to notice and the resulting humiliation factor makes it eminently worthwhile.

You may not be quite ready to take your sissification to full-time status right now. Maybe never.

But when you do have that overwhelming desire to slip into that oh-so pretty dress, it’s super efficient—and really nice—to have a few of the basic feminine foundations already firmly in place.

Your body is smoothly shaved and your nails are prepped to polish. Insert a pair of pendulous earrings into your already pierced ears and you’re already half-a-way there.

Sissy Shop

Now, see how easy it is to be a sissy these days?

Of course by subtly showing your feminine side, your sexuality is going to be questioned by some.

Reason #5 – Sissy and Gay Are Not Synonymous

sissy sexual preference

Many uninformed people quickly question the sexuality of any guy that feels compelled to flaunt their femininity.

Of course these same uneducated people are getting ‘gender identity’ mixed up with ’sexual preference‘.

They’re obviously NOT the same.

What adds to the confusion is that many drag queens have a reputation for being gay… but they’re not sissies. Guys who dress in drag are entertainers who dress up as women as part of their job as female impersonators.

Most of them, I would think, are perfectly happy with otherwise being a male and living their guy life off the stage. Maybe they’re gay, maybe they’re not. None of my business.

Sissies however—despite being portrayed as cock craving gay faggots obsessed with swallowing copious amount of cum while dressed in super slutty feminine attire—are, more often than not, heterosexual.

Certainly, some sissies might be gay—or bisexual—but so what?

Why is everyone so damn obsessed with sexually labeling everyone under the sun, moon and stars?

Just because us sissies identify with the ‘fairer’ gender has absolutely nothing to do with our sexual preferences!

When a sissy is dressed up, she feels like, wants to be, and for all practical purposes, IS a woman. The pretty dresses and other beautiful clothes—at least for me anyway— are insanely intoxicating.

Answer me this…

If a sissy, dressed to the ‘nines’, decides to have sex with a man, while identifying wholly as a woman; does that make her straight or gay?

Things aren’t so black and white anymore. I would contend that a sissy’s sexual preferences might be closer to several shades of pink.

That’s one of the more compelling reasons to be a sissy. You don’t have to be gay (or anything else)—you are allowed to be attracted to anyone who you find attractive—whoever that might be.

Listen, no matter what you do with your life some people are going to label you, judge you, and put you in their own restricted little box that they have allowed society to mentally construct for them.

It’s very difficult for a 5×7 mind to appreciate an 8×10 portrait.

So however they decide to label you, go ahead a allow them to do so.

Don’t argue with reality—you’ll lose that argument 100% of the time.

Just allow people to be who they are because they’re not gonna change… at least not until society collapses.

And while you’re at it, why not allow yourself to be who you are; a misborn male who is unwaveringly embracing her femininity in creative ways which eschews evaluation.

Reason #6 – From the Chaser to the Chasee

sissy chasee

Men in our culture are considered the dominate gender in our society.
They pursue, they take, they achieve, they penetrate. In one word they…


As a male, a former male, a soon-to-be female, or possibly you have always considered yourself a female disguised in men’s clothing—you are acutely aware of this masculine trait.

As a former man myself, I’ve done my share of chasing. It can certainly be a fun, exciting and rewarding endeavor chasing girls. But it’s also…


Furthermore, it can be…

Humbling and frustrating. Chasing women comes with a certain amount of pressure to…


As a sissy, you’ve probably been in a situation—I have—where you weren’t able to get it up at crunch time. Maybe more than once?

A catastrophe like that can send the male ego spiraling down into oblivion… and even further than that.

Yes, although being a man has its perks, it also has its downsides.

Are you tired of chasing?

A really good reason for being a sissy is you can quit all that pursuing bullshit and become the pursued.

Now you’re the one being chased.

Sure, you’re not always going to like who’s chasing you but, that’s part of being a girl. Get used to it.

There’s something quite erotic about reversing roles and now being the chasee. All you have to do is perfect your prettiness and watch the boys come running.

Not into guys? That’s okay. The girls won’t be running because they’ll actually be sprinting—in their heels—towards you.

All you have to do is to work your sweet little ass off to look your goddamn best!

Can you make yourself deliciously desirable?

I’m not gonna lie… it takes a lot of work! The truth is that a sissy has to work harder than a GG to achieve equally desirable—maybe even better?—results.

There’s only one way to find out if all that work is worth it. Try it yourself and see.

Being a desirable sissy—one that makes men rise faster than a homesick angel, while inciting women to twitch in their panties—will make you feel intoxicatingly powerful.

Reason #7 – Pussy Power

sissy pussy power

Undergoing that metamorphosis—from that of a male chaser to a woman being chased will provide you with a whole new way of perceiving the world; through the eyes of your sexuality anyway.

There’s also a significant side-effect that comes with this transformation from chaser to chasee.

It involves ‘pussy power’, a term that you’re very familiar with. But being familiar with it, and experiencing it first-hand for yourself—as a woman—are two entirely different species.

In western culture anyway, men are still considered the gender that wields the greater power. Yes, that’s changing but…

If you take into account heads of states, company CEO’s, military leaders, etc, it’s obvious that men still hold a much higher percentage of so-called ‘power’ than women.

But pussy power is the subtle—and sometimes no so subtle—domain of women that has the ability to trump traditional male power with a well-placed stiletto heel.

You remember Bill Clinton. He will be remembered as one of only three US presidents to have ever been impeached. But he was even more famous for his White House affair with Monica Lewinsky.

The President of the US is widely considered to be one of the most powerful people on the planet yet…

Bill Clinton risked his high profile job, his marriage and his political and personal reputation all for a sexual escapade with a not-so-overly-attractive White House intern.

He could have pursued his sexual interests with any number of much better looking women—paid for or not—in a much more discrete environment. Who knows, maybe he did.

So why did he take the risk with Monica?

Men, in general—no matter how powerful they appear to be—are actually the weaker gender when it comes to sex.

They can’t think past the end of their dripping dick! And there’s a vast acreage of evidence to support this.

You, as a sissy, can experience what this ‘pussy power’ is for yourself.

Perhaps you’ve already gotten a taste of the potential that lies within your femininity.

Just a come-hither motion of your finger—with its prettily polished nail—will bring most men running.

Now, all this pussy power we’re talking about here is nothing more than a superficial and shallow feminine ego-trip. Still…

If you’re female psyche ever needs some bolstering, leveraging your femininity around men will do wonders for it.

Never undervalue your feminine power. When used effectively, it can help you get things by applying methods that will NEVER be available to men.

There was a quote in the movie “Spiderman” that said something like “with great power comes great responsibility.” I’m not sure I buy that.

I contend that it would be more appropriate to say that “great power can instill within a sissy copious amounts of feminine confidence”.

And there’s no better way to buttress that confidence than to master the fine art of applying makeup.

Sissy Training

Reason #8 – Mastering Makeup Has Gotten Easier

sissy lipstick

Mastering makeup application is a skill that separates the girls from all the wanna-be-girls. Becoming competent with applying makeup will absolutely have an immense impact on looking like a lady.

And it’s not because getting good at makeup is easy… hell, it’s anything but fucking easy. It’s because us sissies have so much damn help now-a-days—in the form of makeup tutorials on YouTube.

Back before the internet, if you didn’t have someone like a supportive sister or a genetic girl friend—as in ‘friend’—to help you learn makeup skills, you were on your own… with oftentimes predictably dismal results.

That has all changed with YouTube.

For all the tremendous things that online makeup tutorials have done for TGs, CDs and sissies alike, there’s also a dubious downside to them.

There are now so many amazing makeup artists making so many just as amazing tutorials, that a sissy that’s new to makeup can feel a bit overwhelmed.

So many different looks, application techniques, brushes and products can make a sissy sometimes feel like she’s swimming through a shit-storm.

Listen… these girls on YouTube have been perfecting their makeup skills for years. Some of them started when they were 12 years old, dammit. They are VERY good as what they do and have mastered some VERY advanced application techniques.

There’s no reason to be intimidated however dear.

Pick one favorite look as to how you want to present yourself and focus on perfecting that one look ONLY.

Keep things super-simple at first. A primer and foundation. No more than three colors of eye shadow. Basic highlighting/contouring. An eyebrow pencil. Some lip liner and lipstick.

It’s possible to pull-off a pretty damn good look by just mastering these basics. Pick your favorite makeup artist and watch her videos that focus on the fundamentals.

Work on perfecting your basic look for the first year or so. Once you have that down and have gotten some more-or-less positive feedback, you can then move on to some of the more advanced techniques.

Treat these makeup tutorials one of the greatest sissy blessings you will ever receive.

Reason #9 – Online Shopping is a Game Changer

sissy online shopping

If makeup has gotten easier for us sissies, then the same can be said for stocking your sissy closet with pretty dresses and filling your dresser with sexy lingerie.

I remember back when I was a 14 year-old boy; getting busted for shoplifting in a department store. I had picked out a bra and babydoll nightie.

The salesgirl thankfully allowed me to leave—without my about-to-be-stolen lingerie—only after I told her the items were for my mother.

We’ve come a long way sissy!

Now we can, of course, still go to the department—or thrift—store and buy girlie clothes dressed as a man. I occasionally still do. I’ve gotten used to the humiliation factor to the point where I actually anticipate it.

Makes my little sissy clitty twitch just thinking about it.

But c’mon… shopping for clothes online has changed the game for every woman—especially for us crossdressers and sissies.

Being able to browse for feminine outfits, heels, lingerie and jewelry—not to mention makeup—from the privacy of home has rocketed sissification to heights that we could never have imagined before.

A relevant example is what I’m wearing as I write this email.

My long-sleeved fitted sweater with thumb-holes is something I bought at the store. However my bra, breast forms, panties, mini-skirt and 5″ pumps were all purchased online.

So, if you’re a sissy that doesn’t want to put up with the possibility of encountering some smirky sales associate—then you never have to anymore.

There’s always another side to every coin however. The opposite side to the online-shopping-coin is…

It’s much easier to spend a lot more moolah than you would otherwise while accumulating your female cache of clothing. Hey, but what better way to spend it, I say. And if you’re gonna spend it, might as well do so at a fun place like TooTimid.

Also, finding your frilly, feminine stuff online can be a lonely, isolating endeavor.

But these days, there’s ample avenues available for sissies to overcome the loneliness factor.

Reason #10 – Sissy Social Support

sissy social support

Us modern day sissies have an incredible support system available to us.

Once upon a time, being a crossdressing sissy made for a lonely existence. The fear of being ‘found out’ precipitated some anxious moments—and served to keep us securely locked away in the closet.

Not any longer.

Now-a-days there are plenty of social sites that cater specifically to TGs, CDs and sissies alike.

Now-a-days there are plenty of sissies that have those same questions and many ‘girls’ that have the answers.

Want to meet other sissies to commiserate with? There are several sissy forums where you can do just that.

Feeling apprehensive, or even a little guilty, about having these sissy desires? You can always find a group where you can talk about these issues.

Have a desire to actually meet someone in person? There is no shortage of TG dating sites to help you with that scenario.

I could go on-and-on but you most likely already know all of this stuff. Still, having some sissy support is a super-solid reason why it’s an incredible time to be a sissy.

Reason #11 – Sissification Training Programs


Are you ready to move past soft-sissy theory to bare-knuckled reality?

If you’re interested in an online sissification training program, I found a pretty good one a while back.

It’s very thorough, well organized and thoughtfully written—I’ve actually been going through it myself over the past year or so.

Best part… it’s free!

They do occasionally offer some paid lesson upgrades and a few suggested purchases along the way, but none of them are at all necessary.

Here’s the link if you’re interested:

Sissy Training Academy.

Reason #12 – Sissy Hypno: Be Careful

sissy hypno

Somewhere along your sissification journey, you will probably come to a crossroads. There will be a sign at this juncture that will point to two opposite directions.

Turning left will let you continue on a road that is relatively flat and easy. By traveling in this direction you will be satisfied with where you’re at with your feminization—wherever that happens to be for you.

Turning right takes you on a not-so-level (and not-so-easy) road. This path has some—sometimes severe— ups and downs. But eventually you will arrive at a plateau, gracefully gazing down at where you stood at that crossroads.

Back at that juncture, you were a guy—maybe a part-time girl—often-times fantasizing about being a fully-feminized sissy.

Now, from your perch on the plateau—made even higher because you’re wearing your highest pair of heels (which are now part of your everyday feminine life)—you see the world from a full-time feminine perspective.

When you took that fateful turn to the right, you psychologically made the decision to leave your manhood at the crossroads and become a full-fledged, unadulterated and unashamed woman.

By no means an easy decision!

But if you’re ready to make that commitment to being a girly-girl, as I have, then one of the feminizing tools you have available to you is…

Sissy hypnosis.

Sissy Webcam

Now there’s two distinctly different ways to approach sissy hypno files.

You’ve no doubt already watched hypnotic sissy videos on YouTube or one of the multitude of porn sites. These videos, for the most part, seem to concentrate on the sissy faggot fantasy of sucking cock and swallowing cum.

These types of videos are fine if all you want to do is jerk off and then quickly scamper back to your male mindset. Maybe you’ll purge your accumulated feminine wardrobe and make a vow that you’re perfectly happy to be a man—for now anyway.

I’m talking about a distinctly different type of sissy hypnosis here. Many times it will be an audio file versus one in video format.

I’m referring to a hypnotic file that is designed to make permanent changes at a psychological level.

A file that—instead of inducing a mind-blowing male-like orgasm—trains you instead to be a permanently chastised sissy.

Sissy hypnosis can progressively move a sissy’s erogenous zone back from her ever-shrinking clitty, across her perineum to her ass-pussy.

She can effectively be transformed, both physically and psychologically, from a sexual penetrator to a sexual receptive.

Over time, sissy hypnosis will train you to experience the wonderful world of sissygasms. You will condition yourself to cum like a real girl.

But these types of sissy hypnotic files go way beyond merely changing the way you will experience sex.

They—slowly and surely—will change the way you walk and the way you talk. You will develop feminine mannerisms. You will learn to see the world from a more compassionate, feminine vantage point.

For all intents and purposes, listening to feminizing hypnotic recordings WILL transform your meaningless male existence into a fulfilling life of a fully feminized female.

Now I don’t need to tell you that making that hard-right-turn is NOT for every sissy. It might not be right for you—at least not yet anyway.

But if it is, I’ve compiled a short list of sissy hypno resources that I’m personally familiar with.

Proceeding down this sissy hypno path comes with a warning…

Once you begin, there may be no way to retrace those hesitating, high-heeled steps. You first might wanna sit your pretty little ass down and have a serious sissy talk with yourself.

Make sure you know what you want. Are you ready to fully embrace what a feminized and sissified life will bring you?

Reason #13 – Embracing the Sissy Humiliation Factor

sissy humiliation

As a sissy, you have—by default—a submissive nature. That’s a given.

Most submissives have a penchant for being humiliated. That’s part of the turn-on.

Being a sissy today presents numerous opportunities to take this humiliation aspect, and multiply it by a factor of 10X.

Used to be, sissy sexual humiliation tended to be viewed as a negative—something to be avoided. Voluntary emasculation however is a powerful aphrodisiac. It’s something we sissies secretly crave.

While most people abhor being humiliated, us sissies have a deep-down NEED for it.

It’s a BIG part of what makes us what we are.

As a sissy you have the option—even an obligation—of turning moments of humiliation into a source of excitement.

If you get ‘clocked’ while out in public, revel in the exquisite embarrassment that you feel.

You can choose to eagerly anticipate the feelings of erotic humiliation while you’re receiving a manicure at the nail salon or a makeover in the department store.

The submissiveness experienced while picking out a beautiful bra and a matching pair of panties while shopping in the ladies department can put you into a state of placid pleasure.

Being locked up in a chastity device while fluffing up your wife’s or girlfriend’s lover can send you straight to sissy-humiliation-nirvana.

Transforming your little dick into a permanently limp clitty, rendering you unable to ever penetrate a woman again, can leave you savoring your feelings of ‘sissy shame’.

It’s possible to transmute this permanently chastised existence into a perpetual sexual-high that never gets completely satiated—but also is never extinguished.

Learning to embrace this constant state of sissy humiliation should bring an ever-present smile to those perfectly made-up lips of yours.

Hopefully I’ve convincingly made a case, with these 13 reasons, as to why there’s never been a better time to be a sissy.

What’s The Next Step Towards Your Sissification?

Now that you’re aware that this is a fabulous time to be a sissy, you might be wondering what it’s gonna take from you? Sissification doesn’t happen overnight—it’s a process. I wrote an informative article all about it that I think you might enjoy: Your Sissification Process.

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