Turning Into A Sissy Alone: How To Do It Yourself


A certain type of masculinity was ideal for any man who grew up in the eighties or nineties.  This is how I grew up; watching TV shows showing guys as serial daters, trying to have as much straight sex as possible.  Presenting as anything other than a stereotypical male was taboo and has conditioned me to keep my feminine feelings to myself.


Turning Into A Sissy Alone: How To Do It Yourself


As I got older, I noticed that I was intrigued by thinking of myself in more submissive roles.  Still, I’ve always felt more comfortable keeping these feelings to myself.  It’s hard to find an accepting partner, and I preferred to start off on my journey of sissy self-discovery alone.



1. Getting into the mindset


The most constructive thing to do first is to get into a sissy mindset.  I’ve heard that the brain is the most erotic organ in the human body, and I think it really is true.  Closing your eyes and letting your imagination run wild is a pretty good way of figuring out what will satisfy you sexually and make you feel happy and content more generally as well.  It might help you figure out your desired feminine sissy image and how you’d like to present it.


Turning Into A Sissy Alone: How To Do It Yourself


I tried it and discovered I loved feeling ultra-feminine in lingerie, with silky legs and flowing hair. Imagining myself on a beach, seductively crossing and uncrossing my legs, made me feel incredibly sexy. So that’s what I decided to aim for as my sissy self.


2. Setting sissy time


When I decided to try and embrace my sissy side more regularly, I found it important to try to get into a routine.  Just like when getting into any new hobby or habit, committing yourself to a schedule makes it easier to keep up the routine.  Getting prepared to go into sissy mode became a ritual.  These rituals also helped me get into the right mindset for sissy time.


Turning Into A Sissy Alone: How To Do It Yourself


For me, it became a weekend afternoon.  I’d do my shopping, and then come home and begin my transformation.  Shaving my face and other body hair, laying out my outfit, putting on a wig, and having a cigarette really got me ready for my hours being in my role for the rest of the day.


Turning Into A Sissy Alone: How To Do It Yourself


Even if I wasn’t quite feeling it at the beginning of my rituals, by the end, I was ready for sissy time.  It regularized my time in sissy mode; before, I would engage in the role sporadically when the mood struck, and it could be weeks or months before I’d be motivated enough to do my thing.



3. Sissy wardrobe and fashion


As I said a moment ago, I was drawn to lingerie more than whole outfits.  Everyone has their thing; maybe you’ll like latex clothing or particularly slutty looking dresses.  I love spending time in my lingerie, nighties, negligees, and tights.  Sometimes a black bikini suits my mood as well.




Also, for me, having a feminine shape was very important.  Getting a good gaff to keep my male bits flat and secure was essential at first.  Eventually, I progressed to using a Roanyer vagina girdle.  Breasts were always a bit trickier; a breastplate gives a much more realistic look but can feel constricting and hot after wearing it for a prolonged period, but breast forms, while more comfortable when wearing them for extended periods of time, don’t offer the same visual.



4. Setting sissy tasks


Turning Into A Sissy Alone: How To Do It Yourself


What will you do once you’re in a sissy mode, dressed up and ready?  So, many people typically think that doing traditionally feminine tasks like cleaning or laundry is suitable for a sissy, especially if a sissy maid is your chosen persona.  I did this and found it productive but not particularly pleasurable.  I would usually do a bit of tidying, but only because it gave my sissy alter ego tasks to do, which were different from my default male self.  And this is where I think the key lies; do things you wouldn’t typically do during default male time.  Differentiating these things help develop your unique sissy mindset and identity.


5. Finding your sissy pleasure zone


Finally, during sissy time it’s always important to have some fun and satisfy yourself or frustrate yourself if that’s what you like.  This was actually the most difficult part of my sissy time alone; finding a way to fulfill my desires took time, patience, and practice.  Eventually, I decided that in sissy mode, I’d need to reorient myself to get pleasure from my rear and not my male parts.  I had to think of my penis as a little clitty.


Turning Into A Sissy Alone: How To Do It Yourself


Resisting the urge to touch me for instant gratification in sissy mode took a lot of self-control.  Sometimes the Roanyer girdle is strong enough to deter me, but I’ve also tried a cage.  Sissies playing with a partner sometimes use a chastity cage and give their partner the key.  I couldn’t do this cause I knew I would crack and unlock myself, so I had to find a way to control this urge.


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After some research, I found a way that worked.  Part of my sissy rituals when getting ready is now to lock up my clitty, drop the key in a glass of water and freeze it.  The more water I use, the longer I’m going to be locked up.  In an emergency, I can melt the ice with hot water.


Turning Into A Sissy Alone: How To Do It Yourself


Anyway, this really helped me to train myself to get pleasure from my ass or sissy hole.  Now I’ll happily gently rock back and forth on my favorite ass toys for seemingly hours in a state of sissy bliss.


Having alone time as my sissy self is really gratifying.  It’s nice having a bit of myself that’s really private, just for me, and free of judgment from others.  I like that I’m free to do what I like at my own pace and delve deeper into something new when I feel ready.


Have you sissified yourself or had any sissy motivation? Please share; I’d love to know and get some ideas!

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  1. Im in the swevice and travel for training. When i travel by myself, i make sure i bring my sissy kit with me. The last trip i had was for a week, so when my training day was over, i got back to the hotel and put on my outfit and cage and trained my sissy hole. Utter bliss to let my sissy side out for a hole week.

  2. I got caught with my sissy things about a year ago, all my friends left me and I’m alone but I’m happy cos now they all know I’m a sissy.

  3. I love dressing up as a girl because it makes me feel more alive I’ve have not had sex with a guy yet but I’m hoping that a change because I just want to be treated like a girl. I love dressing up real sexy and playing with my toys. I just want to become a sissy slut for black guys only. So do you think that you can recommend somewhere for me to get sex from Real Men and not play with my toys?

  4. I’m in male mode from 8am until about 1 – 2 pm. The rest of the time I’m my glorious sissy self. Anything I need to take care of is done in the morning. At home I wear dresses, stockings and high heels. I dress completely every day, that’s girdle, garter, makeup, hair and nails, done to perfection, every day. I never take shortcuts because half the fun is getting ready! Once dressed, I often go to Amazon for a girly shopping trip! I long for the day a handsome man takes my sissy cherry. When I find him, he’s going to be glad I did!

  5. This was so hot! I love locking myself in a small chastity cage! I love my breast forms as well. I have been dressing since 9 and it just gets stronger and stronger. I am 54 now and have yet to be with a guy. I would love to try it though for sure!

    1. It’s great to see you embracing your personal style and feeling confident in yourself! Remember to always be true to who you are and explore what makes you happy. When it comes to trying new things, make sure to do it safely and with someone you trust. Best of luck on your journey of self-discovery!

  6. Love dressing been doing it since I was 9 and now I am in my 50’s. Never have been with a guy before and I love my chastity device and breast forms.

  7. Dressing up makes me feel really sexy. I want a man/woman who respects this and wants to be my dom. I love to serve and make others happy and feel good.

  8. I love becoming his woman, to make my man happy, pleased and satisfied! I so want to belong to a Daddy, who will keep me, love me, and make me the best woman he has ever had! Oh, please help me do this!
    Miss Roxanne Lanyon

  9. I can find myself in your journey,.I discovered the female side of myself about a year ago. Tried to wear stocking, panties. Then stopped for a while, cause I thought it was not my thing. After a period of 5 to 6 weeks I tried again, wearing panties, shaved my body and I really liked it, felt great and very comfortable, the biggest problem I have is that I cannot control myself, always playing with my male parts. So was thinking to lock it up. I felt so good the first day’s, felt like a real sissy but I had the keys, so I could unlock myself..oh yeah I forgot I’m already 50 plus in the mean time, but body wise I’m looking very fit. Started a couple of days ago to dress me up, but I feel like I need someone who can motivate and support me to keep on going on my journey.

    I just wanted to share this
    Take care all

  10. i love being a sissy and taking his cock in my mouth and hopefully in my back door!

  11. I remember putting on my mom’s bra,panties ,stockings an girdle for the first time.My cllitty so hard,I shot my cummies within a minute.I was hooked for life.I love it

  12. I’ve known I wasn’t a male since I was thirteen. Due to a very conservative and religious upbringing, I was never allowed to truly express myself and live the way I needed too. Finally a little over a year ago I cracked, I literally couldn’t live another second of the lie I once called a life, so I bought my first set of lingerie, and never looked back! Now fast forward a year and I’ve never been happier! I love worshipping BBC, I love eating an Alpha’s cum. Inhaling their musk while I’m serving them on my knees, where I belong!

  13. should I get into this? it’s always been a thought of mine to become sissy because I’m not much of a man

  14. should I get into this? Your story is very relatable to me… I have always struggled being masculine and whenever I get off to something I always imagine myself in the place of a girl. I think I am a failed male and my purpose is something like this.

  15. I’m a beginner sissy boy, I’m 30 years old and married, I’m very shy about expressing my inner feminine feelings, I hope to cultivate my inner femininity and start a new lifestyle
    Every day I start thinking about how to respond to my inner feminine desires and needs, I do not know how to deal with some of these inner needs and desires, every day the amount and intensity of this inner force increases and my whole mind is occupied some days, it is these feminine desires and feelings that guide my decisions and I have no choice but to obey this inner force

  16. I seem to dream every day of being an obedient sissy for mature black men, pleasing them in every way and it makes me so horny.
    What should I do?

  17. I am new but I also like wear feminine clothes etc but I want to try a relationship with a black dude just me and he all that and real dick and ass sex kisses and etc and fingerring asshole and waiting for that guy and jerking myself off for himself

  18. I am gonna be the best sissy that I can possibly be I love the bbc!!! Omg I’m so ready to comeout! But I can’t yet !

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