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Do You Have What It Takes To Be A Sissy?

Going Out Sissy Does It Right

So what is a sIt's Okay To Want To Be A Sissy!issy to do?  It is Saturday night, the shank of the evening lies before her like an oyster delivering its pearl already gift wrapped.  She wants to get dressed and paint the town red but is inhibited by her own fears of what others may think of her.

Look, I get it, we all have fears, and we all know that marching to a beat that is not the norm can, at times, be frightening.  How often do men forgo putting on their make-up and stockings because of the fear of being “found out”…even if they are planning on staying home?

Your biggest fear is not the judgment of others, but of yourself.  Stop acting in a way that empowers your own prejudices and starts living the life you chose to lead.  We all know what makes you tick…you have an insatiable appetite for sex and sexual experiences.

You know what it means to get dressed up to the nines.  Lace and satin panties and bra, silk blouse and hip-hugging pencil skirt.  How does it make you feel when you roll up those sheer nylon stockings and feel them softly clinging to your legs and feet?  The feeling is like no other…the feeling is like nothing you have ever felt when dressing to be a man.

The Simplest Ways To Make The Best Of Sissy-Hood

Your sexual appetites are wide and thrilling.  You like to specialize in being a feminine cream puff, but you also dabble in many others areas within the realm of kink and power exchange.  During the day you are in charge of yourself.  You may even be managing others in an office or caring for others in a health care setting.

But when you finally end your long and dreary day, your senses come alive because convention be damned behind the closed door…you can finally be who you want to be.  A submissive sissy seeking the attention and approval of your Mistress.

How does it feel to come home and take a warm bubble bath with the essence of vanilla or lavender in the air?  How does it feel to sit in front of the mirror wearing a luxurious robe and heeled slipper mules while applying a light foundation?  Do you enjoy painting your nails?  Perhaps I’ll wear red tonight as I am feeling so hot and horny right now.

You see, there is the side of you who needs to get up each morning and take care of business in the conventional world where dressing as a man and taking charge is necessary for your job.  But there is another part of you that you must also take responsibility for…and that is the part of you that is a sissy.  It’s the part that engages in effeminate whimsy and the sexual delights of gender transformation.

When you are home alone, dressed as a sissy with hard cock in hand, allow your imagination to run free and I will be waiting for you as playtime has finally come.

 

21 comments to Do You Have What It Takes To Be A Sissy?

  • Sissy Donna

    It always feels wonderful to dress and play with and amuse you Mistress. You know me so well.

  • Petey cream puff

    I’ve started this year by coming out to being a crossdressing cream puff to my massuse asI’m so glad I did. I thought as I was getting waxed it was right time to do this. I was very very very nervous and scared about this as she may have dumped me but she didn’t. She asked if I like guys/was gay and I said no the.n she asked if I like makeup/sleeping in lingerie and I said yes. She then asked if I wanted to buy 3 other old purses and I said yes and then she told me that I had to take care of myself/stay healthy which I told her I would at all costs. We then had great girl talk as I told her I felt relived and at ease. She said why didn’t I tell her sooner and I said I was afraid she would dump me but said she wouldn’t and was proud that I told her this. After waxing she wanted to measure/fit me in bra. She said she had same bra it in black and I had maroon bra. It was so hot that she did this as I was wearing my panties while she did thousand she told me to wear it all weekend which I did. The following week she had me come over dressed and said to try on lipsticks. It red but turned orange as my skin complection changed colors and she said I needed to wear burgendy/red shade. She then had me model the purses I bought and said it looked great with my outfit. Then she took me in bathroom sprayed me in perfume/lotion. I told her with lipsticks/purses/lotions/perfumes I look and smell like a girl. She said this is what I wanted and I agreed/did what she said. We’ve gone out for drinks/appitzors and I mentioned that she’s made me better person and she said the same. Her husband came in after massage but she said he didn’t notice or say anything and if he did she would stick up for me. We are going to go shopping where she wants me dressed as I’ve been told I’m going to buy burgendy/red lipsticks/Ralph Lauren midnight passion/passion perfumes/lotion along with me getting makeover. They are out of 32 ounce bottles of lotion and once they have it in stock then we will go. I’m sure I’ll need extra panties/panty liners as I’ll be hard and try not to cream my panties along with her not noticing.😳😢😧. With all this happening in her cream puff as I’m in real female lead relationship with her and I don’t mind. Every Friday I dress in women’s clothes/bra/panty with leggings/knee high boots and I don’t case it feels so good to do this and she’s supportive of this. I’m really her cream puff girl Ms Cindy and I’m so glad and much more happy that I am!

    • Cindy

      Petey Cream Puff, I am thrilled you feel so comfortable as her Cream Puff.

      • Petey cream puff

        I do to. Im glad she’s taken lead in our relationship as well. If she wasn’t into my dressing she wouldn’t have asked me about buying her purses/mentioning using same facial products/inviting me to her place to try on lipsticks/spray me in perfumes/put lotions on me or measure/fit me in bra. With this happening I can’t go back now. I admitted to her I would’ve been better off born a girl and had sisters instead of brothers and she agreed with me. We are going to go shopping as soon as they have the midnight romance 32 ounce lotion available but the shop is out of stock.

  • It takes time and courage to go out dressed. It took me a few times of working up to it before I got dressed and dolled up to go to an adult bookstore to get some Cock. I’ve yet to go out dressed up to go some other types of places (such as a bar or club). Maybe someday I will.

    • Cindy

      Stephanie CDCNJ, perhaps that day will come. You know the Enchantrix Empire is supportive of your growth both as a man and as a woman.

      • Mistress Cindy,

        I can’t begin to thank you and the other amazing women at the Enchantrix Empire enough for your feedback and support. I understand what you do and this is how you are all trying to make a living. You don’t have to respond to a “free loader” like me but you do any way and that is greatly appreciated. I would love to help you out in any way possible and hope that my perspective helps give a better inside into males like myself.

        😀

  • Mistress Amber

    Sometimes, dressing like a sissy is a part of someone, but often it’s something that people do to just relax. How could a bubble bath, feminine lotion and pampering yourself ever be anything but luxury? Let other people go to the gym or eat their feelings or drink with friends after work….there are those that know the TRUE way to relax and unplug, who have turned ‘chill time’ into girl time. It’s the perfect way to spend time and unwind, whether you’re a natural born woman or not!

  • missy laflamme

    the part that stops most gurls is thinking about getting cauight……well guess what…girls already know…..they always knew, they can tell 10 miles away…..it is just the way it is…..then they tell EVERYONE……to them it is fun to out you, of course telling MEN…to set you up on the path of getting what you deserve of course. Women love to see sissy males become cock whores. and as we know, it only takes a little push….you cannot unsuck a cock ! Then once you take it in the rear…..you will always be a gay sissy queer…..lol…..who…not me…..it was just a phase……it will pass…..oh gaga….

    • Cindy

      Missy Laflamme, you’re so poetic…”you cannot unsuck a cock!” Sort of like not being able to unring a bell. What’s done is done, especially if that means swallowing cum.

  • Some great advice here, Ms Cindy, for sissies and for those thinking of expressing their feminine side. Whether a sissy’s thinking of going out or just preening in front of a mirror at home, I think it’s really important to express that side of someone’s personality. And while we both know sissies – especially new sissies – are often afraid of being “found out” we also know that the element of danger can be a real turn-on!

  • Sometimes I think dipping a toe in the sissy whirlpool tentatively is a good place to start. Perhaps the first thing you try is a little stockings under the slacks. Perhaps one day you’ll get up your nerve to go without socks when you wear your stockings. Maybe one day you’ll decide to slip on your sissy heels and pump some gas. Tiny little thrills go a long way when you’re not quite ready to strut your stuff. 🙂

    • Cindy

      Mistress Piper, very well said. No reason to jump into the deep end first. Take measured steps and become more accustomed to the art of feminization.

  • Exactly why we need sissies to be trained with Mistress in charge. now you have groveling and whining and whimpering going on which is what sissy thrives on…right petie cream puff? lol oh yes no worries, Mistress Cindy knows exactly how to handle you 🙂

    • Cindy

      Mistress Casandra, a sissy cream puff requires both a firm hand and a very short leash. After that, it’s just a matter of time before they fall into place.

  • Petey cream puff

    Ms Cassandra, Ms Cindy has me trained to be her sissy cream puff as she always has me wearing bra/panties/slip along with having smooth,girlish soft waxed skin all the time. She threw away all my clothes as I’m wearing women’s clothes. With every lipstick kiss she gives me on my cheeks my body becomes more petite/girlish along with my breasts becoming a d cup filling out my bra. She’s made me her cream puff girl with no intention of me going back to being the strong macho guy I was. I belong to her as she owns me.

  • Jessica

    There is nothing quite like the feeling of venturing out in public as a girl. It has taken me a long time to finally take that step. I started off by wearing panties underneath by boring boy clothes and kind of worked my way into getting more daring. I am to the point where I am comfortable going out with female clothes and some light make up.

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