cross dressing sissy

By Miss. E.W.

‘Sissification’ is the process by which a male will be transformed into a hyper feminine, sexually submissive ‘woman’ by acting and dressing as one, either of their own accord or because their sexual parter forces sissification upon them by making them wear sissy material or act in a sissy fashion as part of the sex act. These males might be particularly fragile, or otherwise lacking in the usual ‘manly’ traits society expects, making forced feminization easy for their sexual partners to push upon them and is in fact something that turns them on. Others, just enjoy the fetish for what it is on their own; feeling turned on by the helplessness of their sissy role or enjoying the clothing and culture.

Despite the fact you may think this is a relatively niche thing, contrary to popular belief male sissy’s are growing in numbers, finding community online where they can be themselves away from the judgmental gaze of wider society and their loved ones. It turns out that even some of the men in your life might be partaking in sissy activity in secret. Having reached out on tumblr to a popular sissy account, I was told by an anonymous source that ‘loads of these guys are married, you know? Like, in straight relationships. Yeah, some of their wives know about it and help sissy them up too, but a lot of the time they’re hiding it and these groups on tumblr and Twitter are the only places they can really be themselves’. Head to tumblr and take a look at the amount of posts — and the notes on those posts — to see for yourself just how popular sissy behavior is online. Some accounts amass tens of thousands of interactions and are posting multiple times a day.

I asked if they were worried about anyone finding out about their secret lifestyle, however I was assured the sissy community is extremely close-knit and anyone outing anyone else would be the ultimate no-no, so it isn’t considered a huge risk. ‘The biggest risk would be if your wife, or girlfriend or whatever found out through something like going through your phone or digging through your clothing and finding something rather than someone in a group online outing you.’

During my research, I found more sissy males who were willing to fill me in on what their sissy attire entailed. ‘Some sissy’s like to be super slutty and kinky, you can find loads of bits online like collars that say ‘sissy’ or ‘slut’ on them and crotchless panties that are all silk cut and sexy’. Even specific sex toys; butt plugs with ‘sissy boy’ engraved upon them, paddles, cock sleeves and nipple clamps with pink bows on them.

From scrolling through specialist sissy stores online I have seen that the clothing is so ultra-feminised that it is arguable actually more femme than the clothing and lingerie that I, an actual biological woman, would wear; pink, frilly knickers, bows and ruffles feature prominently in one online store I browsed. Some stores sell ‘Barbie’ inspired clothing and sex toys, which makes complete sense when you consider that for as long as Barbie has been around we have placed her on a pedestal as the ultimate example of a woman. While another was full of teenage girl-type attire like crop tops and hot pants, but they were emblazoned with phrases like ‘little cum slut’ and ‘cock hungry whore’.

It turns out that there is a lot of cross over for the vast majority of men with their identity of being a sissy and other fetishes, such as being a cuckold or enforced chastity. Sissification can also include aspects of humiliation, such as mocking a sissy for having a small cock or punishing them for lapses in their sissy training by pegging them, spanking them or tying them up. Or there may be aspects of humiliation involving admissions of ‘sissy’ behaviour by the submissive party, playing on their apparent guilt at their sissy tendencies and making them admit all of their desires aloud.

Sissification has even become widespread on online porn websites, where it is easy to find footage of sissy’s dressed as ‘whores’ in anal scenes, chastity scenes including domineering mistresses and transgender porn stars creating niche sissy content.

This is addressed to the wife, partner, girlfriend or other who has just discovered that the man in your life secretly wears feminine lingerie at times. Quite how you discovered this is not important, so much as how you react to it. That in turn will depend on a number of variables including your upbringing, your faith, your education, and your expectations of your relationship.

The revelation is probably a shock and leaves you with a turmoil of feelings and questions. Is he gay? Is he having an affair. Does he not love me?

First, calm down and realize that it is unlikely to be the end of your world or the end of your relationship. Your man cross dresses, expressing a deep seated feminine side of him that you did not know about because he has endeavoured to keep it a secret from you, fearing to damage a relationship he holds as very important to him.

Interestingly, men who cross dress are far more common than one would think. It is not a perversion but an expression of something that is a part of him, something he probably realized as a teen or young man and something that he has likely been ambivalent about ever since, cycling through guilt and grudging acceptance several times over.

There is in fact a wide scale between what our culture has tended to simplify as a binary system of ‘male’ and ‘female’. Your man is a little way along that scale, to all intents and purposes a male and comfortable to be so, but with an added feminine component which our culture provides very little way for him to express. Ironically, women in our modern culture can dress either in frilly feminine clothes or very masculine clothing without comment. The same latitude is not given to men, and should they publicly wear anything that is in the slightest feminine, they are called ‘sissies’, ‘queers’ or other insulting names. Cruelly, our culture has defined ‘men’ in a very narrow and confining way.

Interestingly, our native, indigenous culture has long recognized ‘Two Spirit’ people, further recognizing that such people have value among them as those with an empathy for, respect for and understanding of both primary genders. Such people are respected, not reviled.

Is he having an affair? No, those feminine items are not souvenirs of some sordid affair. He likely bought these things, one by one, on those rare occasions that the opportunity arose. He keeps these things hidden somewhere, fearing your reaction if discovered.

Is he gay? Some cross dressers are, but most are not so inclined. However, cross dressers are often attracted to other men who cross dress, when dressed, though not to men dressed as men. There is a long term for this condition, likely odd to you.

Does he still love you? Yes. Ironically, statistics show that the majority of cross dressers in a steady relationship greatly value their relationship with their partner. This increases

their fear of damaging this relationship. Most cross dressers yearn to be better understood by their partners

The worst thing you can do is to insist your man throw away his stash of feminine clothes and promise never to even think of doing such a thing ever again. He will promise. He values you highly. He will try to keep such a promise. But he will not be able to in the long run. You will simply have driven him further into the depths of the closet.

The better alternative is to accept the situation, recognizing that this is not going to go away and that there is some wisdom in the old adage ‘if you can’t beat them, join them’. The vast majority of cross dressers are ‘sometimes’ dressers, with no wish to live full time as women.

One response could be to accept that your man needs to occasionally express his feminine side, give him specific opportunities to do so, but state that you do not wish to be directly involved. It would likely be a huge relief for him to shed the cloak of secrecy, no longer fearing your unexpected early return home and the trauma of discovery.

Another response is to take an active role. Some partners help their men when shopping for clothes, either in the store or online. Some partners enjoy secretly knowing what their man is wearing under male outer clothes while out visiting with friends or at dinner and a show. Some couples buy matching sets of underwear or nightwear and enjoy wearing them together. Some incorporate cross dressing into their sex life, role playing and enjoying sex while fully or partly dressed. The range of possible responses is wide. Outright rejection is an unwise choice and will inevitably sour or ultimately ruin your relationship.

That your man is less of a man than other men you know is a false supposition. Think of him as more than a man. The current terminology is ill defined and confusing, but think of him as a man who has a female persona beneath the surface, perhaps well hidden but yearning to be expressed.

Yes, there is a risk in opening any door into your relationship. A few cross dressing men ultimately cross a threshold and seek to live full time as women, perhaps entering new relationships with others similarly inclined. A few may even commit to surgical procedures that confirm their new gender identity.

But, this essay addresses the vast majority of men who seek ‘sometimes’ to express a feminine side of themselves that is suppressed by our western culture. They seek to be better understood, not vilified. Please give them space to be who they fully are.

PS Readers, if you can use this letter yourself or know of someone to whom this would be helpful, please feel free to repost or copy.