Cock Radio – click player to listen

What is your Sissy Style?

Every girl has a different style, or in your case sissy style.   I will use myself as an example! I have a very diverse closet.  I pretty much build my outfit for the day around whatever activities I have planned.  Whether casual, sexy, black tie elegant, flirty (my favorite..wink), or professional there is a little bit of everything.  I especially love casual yet sexy weekends: cutoff shorts, a halter top, strappy high heeled sandals, and cute dangling earrings.  You get the idea right?  So, as I look at all of my pretty clothing this morning, it occurred to me that every sissy girl has a certain style.  Wearing panties isn’t the only thing you have or likely want in your closet.  You could be a glamourous sissy, slutty sissy, conservative dress sissy, or a total sissy tease!

Glamourous Sissy Style

Do you enjoy the era of 50s and 60s glam? Pinup girls, donned with hats, sailor tops, shorts and fiery red lipstick?


I always thought of them to be adorable.  There is also evening glamorous sissy style!  You love to wear or desire to own beautiful ball room gowns with dramatic trains, sparkles and plunging necklines.  Pin up hairstyles, full beautiful curls or long hair parted down the side or middle would make your sissy dreams come true!  Although you love red lipstick you likely aren’t shy of a pretty hue of pink, dramatic eyelashes, and your makeup is contoured to perfection. You also can’t wear a beautiful gown New-Sleeveless-Beaded-Fashion-Long-Formal-Prom-Evening-Dresses-Party-Ball-Gownwithout the appropriate undergarments!  Lace up corsets, garters, thigh high stockings and matching bras are ultra feminine aren’t they?  The idea of putting a pair of beautiful nude colored thigh highs on freshly waxed salon legs and clipping your garter to them is amazing.  Who wouldn’t want to marvel at themselves, and even pose in the high heels that match your amazing gown?  Exquisite!

Slutty Sissy Style

Hmmm there is a bad girl in all of us!  When your ass is eager for a good pounding you know just the outfit to wear don’t you?  Heavy black eyeliner, skimpy halter dress, 4 to 5 inch heels, thongs,  and heavy perfume.  Whores love getting attention from men!  They know they are to be used as cum deposits so they dress appropriately for the occasion.  Your sissy hole is so eager and ready with anticipation that getting dressed for all that cock makes your sissy clit throb!  Slutty sissy style is perfect for glory holes, gay bars, or penis scouting with your girlfriends.  I have a few other ideas for outfits too.

Conservative Dress Sissy Style

You admire your female boss’s wardrobe and you mirror it or pick out clothing online you would purchase to have for yourself.


Business suits, white collar button ups, classic hemline dresses, A-style skirts, conservative close toe pumps, and simple but chic jewelry are on the list.  Oh, but her eyeglasses and nude lipstick is heaven! It is every sissy girls dream to also master the professional bun!  She holds a few strands of her hair with bobby pins, and you can only picture those little hairs framing her goddess face while you lick her vagina under her desk at work.  It wouldn’t surprise me if she wore crotchless panties, so her sissy girl employee can eat her pussy for lunch- and then sends you back to your desk to finish her tasks.  How divine would you feel being able to channel her style and still serve her?

I’d love to know which style you girls have……………


Miss Carrington



13 comments to What is your Sissy Style?

  • Petey cream puff

    I have tons of bras/panties/boyshorts. Also tight body con sheath dresses along with 5 prom dresses/wedding dress. I also have many leggings/yoga pants women’s heels/mules/knee high & ankle boots. Of course I have perfumes/lipsticks/girlish lotions. When I do calls I dress up a girl in bra/ panty set with lipstick/perfume on wearing my heels. With women’s style I need to stay lean and slender instead of big and bulky/fat which I let myself do 🙁 do you think eating small clean meals is way to go? I was eating 5-6 times a day but this has caused weight gain. I’m switching to 3 small meals a day with lots lots lots of water in hoping this will cause me to lose weight.

  • Ms. Carrington, as one Sissy trainer to another, I love your breakdown of style for sissies–this is so important to all of my sissy callers and I know yours as well. It still never amazes me that of all the sissy styles (oh and don’t forget Sissy virginal bridal outfits/lingerie) — slutty dressing always wins hands down. I’d say 90% of my callers love to be slutty (although they might own a few different other styles of dress). Hope to train a sissy together some day soon!

    xoxo Mistress Audrey

    • Carrington

      OH yes! Sissy brides are my favorite also. I think training a sissy together would be a marvelous idea. As I think about it. Please create a sissy post and I would love to host it on my blog. You will be my first special guest. (kisses)

    • OnesubForYouTwo

      Someday i- will find a Mistress that will help me become a sissy slut and turn me out. Letting me eagerly serve at glory holes and use my ass till it gapes.

  • Petey cream puff

    Also Ms Carrington I’m going to buy women’s ankle boots and women’s skinny pants. Would men and women notice the difference between men’s slacks & wonens Lonny pants?

  • Petey cream puff


  • Jessi lynn

    I ussually just wear panties under my male clothes because im not very passable. But I do pilates and barre workouts and at the studio I like to wear leggings,capris and short shorts. I was worried the women would be bothered by it but they have all been so sweet and friendly treating me like one of the girls. I sometimes wonder since the leggings leave so little to the imagination maybe they they just took pity on me and I know sometimes my panties peak out im sure they all noticed.

  • Petey cream puff

    Yoga pants/leggings/capris are hot! I’ve been wearing them and they are better then sweat pants/boy slacks. It shows off my cute butt and my curves. Also paring them with boots/women’s tank top/sports or regular bra.

  • Petey cream puff

    I’d love to be sissy bride that you & Ms Audrey can turn me into.

Leave a Reply




You can use these HTML tags

<a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <s> <strike> <strong>