Sissy Positivity!

Sissies are a distinct breed of transvestites. A sissy is a transvestite 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 transvestites 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 warddrobe, 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!

It doesn’t matter if you’ve been dressing up for years or if you started yesterday; we’ve all had the same fear. The fear that the cashier knows you’re really buying the dress for yourself, that those heels look dangerously your size and not your ‘girlfriends’, that it’s strange that a man would spend ages looking for something simple - as though he was browsing.

Some of us (myself included) have grown out of this fear, but that doesn’t mean we’ve never experienced it, or ever been caught in fact. However, sometimes being caught does more good than bad, but I’ll explain that later.

So, here are some of my favourite tips that I (used to) use to not draw suspicion to myself when looking for dresses/underwear/heels etc:

1. “It’s for my girlfriend” 

The easiest and most common trick in the book, and I feel it doesn’t need that much of an explanation; just pretend it’s for your ‘girlfriend’. This is easier to pull off when you don’t have anyone with you because then they can only imagine what size your ‘girlfriend’ is.

Pros

Can get away with buying nearly anything, provided you’re alone.

Easily believable.

Cons

Going-on about your ‘girlfriend’ too much will look suspicious.

Retail Assistants aren’t stupid. Some will figure out that you and your girlfriend are similar sizes.

2. “Help me I’m stupid and don’t know how to do girl’s clothes”

Another common one, especially useful when browsing. It’s not right to stereotype, but let’s face it some are true, and men very rarely know how to browse for clothes. This is perfect though, as you can simply play the role of a typical man who doesn’t know the difference between peplum and skater. 

First, make sure you write down your measurements and what style of dress/skirt/whatever you want. This will come in useful for later.

Ask a Retail Assistant to help you find a dress/underwear/heels/whatever. Don’t give away too much information at once (who it’s for/their size/what they like), just say you’re looking for a dress/skirt/whatever in a certain colour/style. Chances are the Retail Assistant will ask the extra questions. This is when you pull out your note from earlier with all the details, and simply read it out to them. This all adds to the idea that you have no idea what you’re doing and you’re just doing the shopping for someone else.

Alternative Method: Go in the shop once and take a picture of what you want. Return to the shop later and show the Retail Assistant the picture. They’ll simply assume you’ve been sent on an errand.

Pros

Much lower risk of getting caught, especially if you do it right.

Allows you to browse without risk, plus Retail Assistants generally give good advice.

Cons

Very time consuming, especially if you already know what you want.

Not for the prideful.

3. “Yep, those heels are for me. The dress as well”

Here’s a method which I learnt a long time ago: simply being honest. I’ll walk you through how I discovered how it works:

I was buying a pair of heels with Moon. You might have already guessed that we don’t share the same shoe size (I’m size 9, she’s something like 5) but we were hoping the Sales Assistant wouldn’t notice. Funnily enough when we get to the checkout, the cashier looks at the size and then at Moon’s feet, quickly adding “I think there’s been a mistake, these shoes look way too big for you dear.”

Without missing a beat, and definitely before Moon could speak (because she would definitely try to think of an excuse which most likely wouldn’t make sense) I replied “That’s because they’re for me.”

Sounds like a nightmare right? Being caught trying to buy clothes and getting exposed, horrible right? 

WRONG

You can make up any story you like, as long as it involves you wearing the clothes. My favourites include:

Stag party

Genderswap party

Charity act

As long as you don’t give specifics, you can get away with it. I’ve even had occasions in the past where Sales Assistants have offered to let me try on the clothes before I buy. 

Pros

No lying involved, so suspicion flies out the window.

The Sales Assistant can help you more if they know it’s for you.

No-one really cares if the dress is for you.

Cons

Ironically, can take a lot of balls, especially the first time.

You might be unlucky and run into someone narrow-minded. This won’t really make a difference except for maybe a snide remark.

Added Bonus: I’m now at a point where I can straight up tell a Sales Assistant I’m buying dresses for myself without feeling the need to explain it.

So What One Do I Use?

Whichever one you feel most comfortable with. I started at 1, moved on to 2 and then eventually got used to 3. It doesn’t really matter as long as you get what you went shopping for. In some shops I’ve genuinely said “I’m a crossdresser, so what’s gonna make me look pretty?”. So far, I’ve had no trouble, just the occasional question.

Sorry again for the lengthy post, but if you need any reason to shop in-person rather than online, just remember that some of the best outfits come from browsing through racks, not webpages. For example:

Everything in that outfit: the dress, the heels, what’s underneath, I bought them all from a shop, not online. It’s one of the my favourite outfits and I would have never got it by simply searching online.

Hope this has helped some of you! Just give it a try once in a while and you’ll get used to shopping the right way!

Any questions? Feel free to drop me a message! :)

If you’re going for the full ‘trap-mode’ aesthetic, wanna draw attention away from your upper body, or just love long legs that go all the way up, the following guide can be used by anyone (guy or girl) looking to enhance their look and make legs their best asset!

Step One - Hair Removal

Shaving your legs is the most basic of basics and quintessential to having more feminine legs. If you have hairy legs then begin by taking a nice hot shower first and exfoliate all the areas you wish to shave before applying a decent shaving foam (by this I mean something with a combined moisturizer, which most have these days). Once you’ve gotten rid of all that unsightly masculine leg hair, remember to moisturize your newly bare-shaven legs to reduce rashing/ingrown hairs.

Step Two - Tanning

This is quick and easy! Either find a good fake tan to apply to your legs (and the rest of your body so you don’t look weird) or, for those of you living in a sunny climate like myself, get a natural tan.

Step Three - Stockings/Hosiery

If you don’t want to tan or haven’t had time to shave yet, a good quality pair of opaque stockings  can give your legs the appearance you’ve been looking for. For the rest of you (those who did Step One - Hair Removal), try to stick to black or nude/sheer stockings instead of coloured tights unless they go with your outfit, for example; grey/white knee highs go well with the ‘librarian/secretary’ look, or fishnets with certain lingerie/babydolls.

Step Four - Skirts/Shoes

The right length skirt can help give you that ‘leggy’ appearance or create the illusion of slimmer legs with the right pattern. As for shoes, a nice pair of heels can be the difference between looking like a super-model and looking like a guy in stockings. 

If you have muscular or defined legs already, go for a shorter heel; the higher the heel, the more your muscles tense up and contract while wearing them.

Another good tip is to avoid pointy-toe shoes as they can elongate the appearance of your feet and make an already large male foot appear longer! Finally, if you aren’t wearing stockings but have a nice pair of open toe heels then you should try to give yourself a pedicure/paint your toenails.

Step Five - Exercise!

You don’t need a gym membership and you don’t need to spend half a dozen hours a week getting into shape - obtaining a more feminine physique can be as easy & simple as spending 5 to 10 minutes per day doing exercises that not only work but make you feel better too! Leg exercises are some of my fav’s as they can be done almost anywhere if you have a spare minute or two and can be done without expensive equipment too.

A few sets of lunges, some cardio (running/cycling etc), and squats performed every day can help you slim down, tone up and feel good! For a lil’ added bonus you can try working out in heels or even try some basic yoga steps to loosen/stretch muscles in your body for an all-round better posture.

I hope this guide proves helpful on your journey towards whatever sissy goals you may have, whether its just having a little fun or becoming the sissy you’ve always dreamed of, and don’t forget to give feedback if you have anything to say as its always welcomed.