Are you ready to go “Down The Sissification Rabbit Hole?” Then read this…

What Does it Mean to Be a Sissy?

what does it mean to be a sissy?

The term ‘sissy’ can have different meanings depending on who you ask. Oftentimes, sissies are protrayed as cock craving faggots who have re-programmed themselves to the point where they have given up any thoughts of ever being sexully intimate with a gentic girl. But is this really an accurate viewpoint?

I’m not so sure. Many people tend to arbitrarily label any male who enjoys dressing up in women’s clothing as gay. It’s way too easy to get gender identity confused with sexual orientation. Things aren’t always so black and white.

For example, are we going to put drag queens, crossdressers, transgenders, transsexuals, sissies and the seemingly macho guy who likes to occasionally put on a pair of panties all in the same category?

If we do, we are only allowing ourselves to see the tip of the iceberg. 90 percent of what’s going on inside the head of any of the above will always stay hidden from but only the most understanding and compassionate of people.


The truth—I think anyway—is that the majority of sissies are mainly heterosexual with some not-insignificant bi-sexual tendancies thrown in. Since sissies can be complicated creatures, their sexuality is likely to be in a continuing state of evolution.

As a sissy myself, I’m very much attracted to women. The thought of kissing and having sex with a man, while in male mode, is a complete turn-off for me.

sissy chastity devices

HOWEVER, when dressed up, I look, feel and act ultra-feminine. I want to experience everything that a genetic girl feels… and that may include having sex with a man. Suddenly I morph into a full-on, sissy slut. Since I would be completely associating with the female gender while with this hypothetical male, would I be homosexual or heterosexual? Interesting question.

For me, being a sissy is all about the beautiful clothes! When my slim, very in-shape body is dressed in sexy lingerie, a mini dress up to my ass and sky-high heels, nothing would validate my feminity more than being with a man who desires me. But as far as relationships go, I would always want to come home to a woman—or another sissy, or a MtF TG.

Things can certainly get confusing inside of a sissy’s pretty little head. In the quest for clarity, I offer up the following article (not written by me) that attempts to accurately describe what it means to be a sissy:

Sissies are a distinct breed of crossdresser. A sissy is a CD who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires—their ultimate fantasy woman, if they were normal, rather than being a sissy.

Sissies are crossdressers who can’t be sated by just throwing on some panties and jerking off. They must strive to become their ideal female. This means the fetish will transcend the bedroom, and creep into the rest of their life. A full wardrobe, makeup, wigs, etc. Sissies will spend more time looking at women’s outfits than they will looking at the women wearing them. Sissies keep their body hair shaved, likely wear panties (or more!) at all times, nail polish on their toes, etc. Being a sissy takes commitment and dedication.

Sissies are bisexual, but not in the traditional sense. You aren’t going to see a sissy settle down and marry a man. You won’t find many that will say they find men attractive. Remember, a sissy seeks to become the embodiment of what their dream woman would be. As such, their interest in pleasing men is distinct from that of homosexual men. Their interest in men comes from seeking validation that they have achieved their sissy goal: being feminine enough to interest “straight” men. They aren’t into the men themselves as much as the men are sex objects that a sissy uses to confirm her own sissyness.

Sissies are submissive. You can be a crossdresser who makes an effort to look the part and not be submissive, but that means you are not a sissy. A sissy gets off on pleasing others. She doesn’t worry about herself or her pleasure nearly as much. This is where you see chastity and cuckolding come into play for a lot of sisses. Chastity is sought because it allows a sissy to stay horny, giving them the drive to further their sissy desires (rather than losing them after orgasm). Cuckolding is natural because if a sissy is going to have a wife or girlfriend (remember, sissies aren’t typically into men romantically), by her nature a sissy is unlikely going to be able to be much of a man when it comes to sex. As such, not only is the woman more likely to look elsewhere for those needs, the sissy herself shouldn’t mind. Her wife isn’t cheating on the sissy with “another man”, but is having sex with “a man”. The sissy isn’t a man anymore, so why should she be jealous that her wife needs a man from time to time? If anything, the sissy can relate. She needs a man sometimes too!

Sadly, the term sissy tends to be overused these days. Guys with thick body hair showing off their one pair of panties, or ones where their small wardrobe is a mishmash of mismatched clothes that no woman would ever wear, these sorts are all using the term sissy. Guess what guys? You aren’t a sissy. You may have the mindset, you may be working towards it, but until you get there, you aren’t one. You need to learn fashion, makeup, and you need to work towards looking hot. Instead of doing just enough sissy stuff to get your cock hard, you need to focus on doing enough to get someone else’s cock hard. In a world of pantyboys, you need to rise above. You need to embrace what it means to truly be a sissy and dedicate yourself to it.

There you have it… clear and concise thoughts on what it means to be a sissy—expressed much more eloquently than I could have ever done.

Are you ready to go “Down The Sissification Rabbit Hole?


Then you’ll want to read this…