Stepping Into Sissyhood, Is It Right for You?

A sissy lifestyle isn’t something to be taken lightly; it can be what you make of it.

Sometimes crossdressing is just an exercise in escapism; sometimes it expresses our need to just be feminine; however, for some of us, it can be a fetish or a form of sexual release.  Being a sissy could mean a number of different things, but largely it relates to taking sexual pleasure in a submissive role; shedding any aspect of your masculinity and taking on a new identity.

Sissy play is quite popular in the fetish community.  However, living as a sissy, or adopting a full time or semi full time sissy lifestyle is quite another.  I’d like to discuss this, more involved sissy lifestyle, and discuss how it can be integrated into your life.

1. How do I know if full time sissy life is right for me?

A lot of people who are turned on by becoming a sissy are conflicted by their desire to become a near caricature of a cartoonish stereotype of a submissive girl.  Lots of men who engage in sissy play report intense feelings of shame after they have achieved satisfaction, but that sooner or later the desire returns.  Some report that the desire gets stronger over time.  Moving beyond this involves a lot of reflection and self-discovery.

If you’re finding that dressing up like a girl turns you on, that it is linked with your own physical pleasure and you try to behave very passive and submissive when you’re dressed, you could be opening the door to sissyhood.

When you look at women, do you check out their looks, or are you admiring their shape and feeling jealous of it?  Perhaps you’re even feeling like you’d rather take on the traditionally female role during sex.  Thinking about this; some small signs would be how you feel when wearing feminine clothes, shoes or performing a feminine role.  If you feel down about needing to put these items away for a while in order to reenter your male role, you might benefit from letting out your inner girl or sissy.

Finally, do you feel the need to dress and be girly even at times when it wouldn’t be acceptable?  Starting to wear panties under your clothes regularly, not because you like the comfort, but because the idea of wearing them and possibly being discovered excites you is a sign that you might not just be a crossdresser.

2. What does being a full-time sissy mean?

Being a full time, or even semi full-time sissy means that you’ve decided to spend at least some of your time, and likely all or most of your sexual pleasure from your feminine role.  Perhaps you’ve also adopted this role for longer periods of time without any sort of release.

Exactly how this all manifests for you personally is up to you.  The important thing here is to remember to retain control of yourself and your body.  No matter what you decide to do, it should be you in control.  Moving away from that can become quite problematic.

Getting started will be the most difficult part of this journey.  If you’ve decided that you want to give it a try, it’s definitely worth doing a bit or reading first.  This will help you establish your boundaries and the first steps that are right for you.

Reddit has a number of forums about this fetish; I think this one is very helpful.  Learning from others, your peers, is going to be essential.  It is also going to be emmensly helpful when trying to overcome the ‘shame cycle’ that a lot of sissys experience.

On a day to day basis, I think there are probably a few basics to living a sissy lifestyle.  First of all, you’re going to want to achieve a slim feminine physique.  You’re going to have to watch your diet closely.  Moreover, body hair is going to have to be a thing of the past.  Keeping yourself smooth will require shaving and shaving regularly.  Little things like keeping your nails manicured and polished, neatly shaped eyebrows are going to be part of your daily routine.

If you’re only going to be a part time sissy, I think that all of the above applies.  You will still need to watch your diet and your research.  However, you’ll also need to be able to compartmentalize the different bits of your life; you’ll definitely need to set some strong boundaries.  These boundaries will have to be about times, places and who’s involved.  From experience and research, I can tell you that some of these boundaries might get blurred from time to time.  Sissy life and sissy play can sometimes be addictive, and it is partially the element of secret naughtiness that makes it so.

3. Going deeper into sissydom

If you take the first steps and find that living a sissy life is pleasurable, you might be ready to take the next steps.  Deciding between full time and part time sissyhood is the first decision.  I’ve heard that as time progresses and you drop deeper and deeper into your sissy life, you’ll desire pleasure as a woman more and more. 

This will mean that your male bits will slowly become less of source of sexual pleasure. This can be achieved by locking them up with any number of toys.  Chastity cages are a must have for either the part time or full time sissy. These can literally make it impossible to achieve a traditional male orgasm.  Part time sissys will set times to be in chastity, either with a timer or by passing control to a trusted partner. Full timers; well, they probably won’t need a timer.  Another idea would be to choose a Roanyer Girdle, which gives you the added feeling of achieving a higher level of femininity!  Either way, you shouldn’t be getting off the same way you always have.

Developing other ways of achieving sexual satisfaction is going to be essential. If you’re only part time, you might find that these methods become more pleasurable for you as time passes. Full time sissys will rave about how they’ve gone full bottom, or only are allowed anal pleasure. Using plugs, dildos, and/or vibrators to achieve orgasm will become regular for all sissys, full or part time. How to do so is a matter for you to discover and experiment with; all I’ll tell you is that we’re all capable of it. The journey of discovering this should be your own, don’t give up!

4. Choosing to partner up or stay alone

Lastly, stepping into sissydom usually involves a partner. I think that having a male or female partner for your sissy journey is entirely up to you.  Typically, if you think of a sissy, the dominant figure is a man, but I think it might even be sexier to have a female partner and mentor. I think that the best thing about having a partner is that they would push you to really explore your boundaries and push the envelope. It’s too easy to give up on stuff when you’re alone and a partner can give you validation that you need.

How you and your partner choose to engage in sissy play should be understood between the two of you. I’ve read some extreme accounts; sissys being kept in a cage, whipping, etc. This all wouldn’t be for me. However, the idea of a woman gently manipulating me into permanent femininity has some appeal. In any case, its important that there be agreement and understanding between the two of you, no matter who it is and the nature of your play.

Figuring out exactly who should be or could be a good partner for this sort of play or lifestyle is a daunting task. I would think of someone supportive and open minded, but also adventurous. What would your advice be?

Buying into a sissy lifestyle is likely to have a big effect on the way you experience quite a lot of your life. If you’ve found that crossdressing turns you on and your desire to experience more of the female experience, it could be a step forward for you. It requires a lot of self-acceptance and understanding.

The type of sissy fantasy you’re going to try is your choice.  Take some time, think it over and when you’re ready to take the next steps, go ahead.

Do you have any experience of sissy life?  Perhaps you can share some advice in the comments below.  Or maybe some words of wisdom for those looking for guidance about the next steps.  We’d all love to hear it!