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Why We Love A Sissy….And You Should Too!

Why We Love A Sissy....And You Should Too! From A Caterpillar Comes The Butterfly

Funny how life can change so quickly.  Like the vicissitudes of a meandering river…one day you’re married (most likely unhappily) and the next thing you know you’ve come to the realization that what you really want is to be a sissy.

Your level of comfort in being a man and sporting a knobby-headed penis has always been an unanswered question for you as well as an anxiety-inducing topic.  Every time you’ve seen a beautiful woman a dangerous thought materialized in your mind…you wish you could be her.  But truly, what you really hoped for was to be given permission to wear her clothing and have her man.

Well, maybe you will have to work hard to have him, or someone like him for yourself.  You’re timid and feminine so you would make a better woman than a man, is that right?

I hope you know it takes a lot to be an acceptable LDW sissy…are you up for such a challenge?  You have this recurring fantasy of waving the end of a colorful silk scarf to your admirers from a tall balcony with your head somewhere lost in a perfumed cloud of joyfulness, gaiety and delight.

Pinks And Pastels Are In…Strumpets And Harlots Are Out

To maintain our standards here in the Enchantrix Empire, you must be disciplined and enthusiastic about your new role.  Sissies of low morals or ill-repute will not be tolerated.  Strumpets, harlots and others of that unfavorable ilk can expect to face severe punishment for all sissy crimes and misdemeanors.  Often times extended chastity is the penalty…but, if bad enough, banishment and exile from within our walls could be imposed.

You dare not say you have not been warned!

Now, with that out of the way, it’s time to start thinking about your special day of girlie dress-up and to go forth, in public, wearing your cutest outfit.  This includes matching panty and bra, pantyhose, dress, wig, FULL MAKEUP, nail polish, high heels, perfume and anything else you may want to accessorize with.  Remember, pinks, pastels and softer more feminine shades should serve as a constant reminder to you of your femininity…so make your selections carefully!

Freedom Comes With Twitchy Dicks

Once you’re all dressed up you can go anywhere without a care in the world.  You can even go shopping for lingerie and makeup all the while looking pretty and witty.   I realize most crossdressers never leave their homes while dressed up, but maybe someday with the proper support, you will be up to taking a chance.

You’ve been wearing your wife’s clothes often, either covertly or with her expressed permission.  Knowing that she has worn the exact outfit while intimate with another man gets you aroused and your clitty hard…which, by the way, is already twitchy because of your sudden newly-found freedom.  For crossdressers, the combination of sexual arousal and humiliation can be overwhelming at times.

All you need now is to complete your new role is get into doggie-style position with your rump up and head buried in a pillow while grabbing the sheets.

Prove to me you can accept a nice size strap-on while dressed in frilly black lingerie.  I’ll be waiting to hear from you…

16 comments to Why We Love A Sissy….And You Should Too!

  • Petey cream puff

    I admit I’m jealous of women. They really do have the better clothes. I’ve never gone out wearing women’s clothes not bra under my shirt. Panties I have but that’s it.I have plenty of dresses/bras/panties/boots/slips/heels/tops/yoga pants/leggings/capris..also I have makeup/lipsticks/perfumes/lotions and yes I have dressed at home and it’s hot turn on in which I get hard and off. I’ve gone to my salon wearing bra/ yoga pants/ankle boots with unisex sweater but girls at salon didn’t bat and eyelash:( I’d really love to have women do this to me for real but I’ve had no luck:( at my age the ship has sailed:( but with you already keeping me dressed in bra/ panty set along with women’s clothes/arched feminine eyebrows I have found my women.. YOU. I’ve never done strap on before as my feminization mistress I’ve no choice in this as I’m your cream puff sissy who’s nails are firmly dug into me with no intention of ever letting me go.

  • Happy Birthday, Mistress Cindy!

  • Sissy Lynn

    Mistress – I would love to prove to you that I can accept a nice size strap-on. But may I please be dressed in frilly PINK lingerie? [curtsey] I do my best sissy work while in pink. And I would love it if you made me wear me looong hair in pigtails. Aside from the fact that it’s so girlie – and its my favorite way to wear my hair – it just may give you better leverage by pulling them back [giggles]

    • Cindy

      Yes, you may dress in frilly PINK lingerie it will be appropriately fitting. More leverage always adds to the excitement, right?

  • “But truly, what you really hoped for was to be given permission to wear her clothing and have her man.”

    I’ve recently wondered whether my attraction to women has been envy rather than sexual attraction.

    • Cindy

      StephanieCDCNJ, I think it is necessary for you to continue to dress up as a female so that you’re pleased with your progress. As this will change the discontentment you feel towards women.

      • Being married makes that a challenge though I’m currently working to open up to my wife about my dressing.

        • Cindy

          Okay. So we know that society does not make it easy for men to express their feminine side as men, and it’s even harder to do so if married. I think this is why it is easier for men to express femininity as a female persona.

  • Strumpets and harlots be damned, lol. That part of your post had me slightly confused, Ms Cindy. What is it about slutty sissies that makes your pot boil over? I am genuinely curious and I am sure a lot of slutty whore sissy bitches out there are keen to know as well. 🙂

    • Cindy

      A strumpet or a harlot are whores (prostitutes)…fast and loose women who have sex as a money-making venture. Being slutty is not the same as putting yourself out there as a sissy to just make money…

      Mistress Cindy wants her sissies to have a genuine love of their femininity and to be open to sharing that beauty with others. If a sissy wants to be “slutty,” go for it and have fun. I hope this clarifies all confusions.

  • Nice post, Ms. Cindy! You wrapped up with one of my favorite pastimes, sissy strap-on sex. I’ve always felt that the pink icing on the sissy cake is the introduction of a strap-on. Whether a sissy enjoys dressing in lingerie that is sweet and demure or racy and tantalizing, submitting to a strap-on is a sissy rite of passage. It can be a prelude to a sissy enjoying a real man or it can be an intimate treat enjoyed between a sissy and her Mistress. Either way, it’s a sissy must!

  • Donna

    You know Sissy Donna can’t wait to be your Sissy again – maybe in a new French maid dress or maybe in a beautiful pink and black dress with short short skirt with her cheeky pink panties showing?

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