We often talk about dressing our sissy girl’s in frilly girly or slutty clothing today I wanted to talk about dressing them up in evening wear for very special occasions. This blog was inspired by a very classy girl Connie from chat whom I have had the pleasure to get to know and even help pick out some sexy evening wear for a classy night out….thank you Connie for reminding me and everyone that being a cross dresser or sissy girl can be an elegant classy thing not just a horny slutty thing.
Preparing to dress
Now before we even get to the dress and accessories that go with dressing up we need to discuss the preparation a sissy girl or cross dressing man has to go through. Start with a nice hot girly bubble bath, this will release your day’s tension as well as fill your mind with soft feminine thoughts, with every breath you take you will inhale that soft girly scent from your bubbles and it will create a feminine state of mind. Then you can begin to prep shaving your legs and under arms as well as any other body hair not fitting for a woman. Once done with that you can lotion up your freshly shaved body with some feminine moisturizer to give your skin that sexy glow you admire on women.
Proper undergarments
Every sissy girl and cross dressing man should have the proper undergarments to give them that sexy feminine look and feel and trust me ladies a sexy peer of thigh highs does wonders to make you feel even more feminine. I would suggest a bra with the appropriate sized breast forms for the dress, panties of course and a garter belt and stockings. If your do not have a feminine shape and feel like you need more curves they have done wonders with the new body shaping undergarments so look into them if you want a bit more curvy feminine shape.
Classy Not Trashy
It is important when dressing in an evening gown to look classy not trashy so spend some time and a little extra money to get the look that best fits you. A sequin floor length gown with a slit up the side says sexy not slutty and something that is slightly low cut can emphasize your best assets without exposing all your business to the world. I have helped a few cross dressing and sissy girl phone sex callers pick out the right look and color to best fit their body and skin tone so please do not be shy to ask for advice and shopping help, after all who better to ask then a woman when trying to look and feel more feminine.
Accessories that flatter
You do not want to overdo it when dressing in an evening gown more often than not the gown itself is a statement and you will need very little to enhance it, a classy pair of heels is all you need not a 5 inch pair of stilettos and perhaps a pair of dangling earrings to frame your face is all you will need again it depends on the dress but less is more remember that when dressing up. Your hair style depends on you I prefer an up do when dressing up it looks and feels elegant and classy. Your sissy eye make up again should be classy not trashy don’t overdo it like a drag queen take the time to apply your making to enhance your features not over exaggerate them, sexy smoky eyes with just a hint of blush to give your cheeks color and accentuate your cheek bones and some classy lip stick to enhance your lips not slutty red or hot pink to shock everyone. Your nails should also be done I happen to have natural nails but tasteful acrylic nails are fine too in a color that shows off your dress not clash with it, and there is no need to get super long nails, your nails should make your hands look sexier not over power your hands and look trashy. And finally a small spritz or two of your favorite perfume (do not bathe in it) and a small coordinating evening bag and you’re set for an elegant classy night out.
This is how you dress for a classy evening out if you’re looking for tips and help finding just the right thing for your evening out feel free to contact me I am always willing to help you sexy classy cross dressers and sissy girls out. E-mail Constance@enchantrixempire.com and my Yahoo screen name is EmpressConstance and of course you can always call me for some one on one sissy consultation
800-601-6975
how do i dress for a date with Wes E. Pooooooo ??
You dress how you always do when preparing to have your garage filled……Naked and lubed!
Mmm I love the fact You appreacate Classy not trashy. Thats what I perfer. I only act like a slut in the bedroom. Outside the bedroom I’m quiet and shy
I am glad you liked my post and I love love loved how you said your a slut in the bedroom hehehehe I wanna hear all about that too but as you know there is a time and place for everything. 🙂 thanks for the comment
As always, sage advice!
thanks NB 🙂
This is a very nice, very informative post. I like that you aren’t just putting some make-up and a dress on a man and saying, “Ok, now you’re a girl.” You take your time, you set the scene and you get the person to be in the proper frame of mind with a hot bubble bath. Then you start with the actual make over. This progression makes perfect sense but I’ll bet a lot of people leave out the actual preperation. While this post isn’t me, it does show the attention to detail that you give with each fetish. You really think things through before just jumping into the deep end. I also like the “classy not trashy” line. Speaking for myself, I like a classy woman way more than a trashy one.
Thank you for your comment gummy and you too have earned your pennies well for such a thought out comment. I know it is not your thing but it thrills me that even someone not into this fantasy can see how I took the time to guide them and how it makes perfect sense to prepare for a classy night out and I of course enjoy the fact you like classy and not trashy 😉
Well i was going around to all the Mistresses to check out their blogs and pick up a few pennies and what do i find here MsC… but some very practical advice for sissies like me. i must say that the biggest problem i have looking girlie is the eyebrows, but real life keeps me from plucking or shaving them. Do You have any suggestions?
Hi Panty sue and thanks for the comment your pennies are well earned with this comment! I am glad you can relate to some of what I posted and I understand your issues with not being able to pluck or shave your eyebrows the only really think you can do is use an eyebrow pencil to define them and give the appearance of a false arch. Now I have no idea what your eyebrows look like now I assume it is not a uni brow out of control type thing because men these days do get waked and shave in those cases. but try to define an arch and a more feminine look with an eyebrow pencil is the best advice I can give you 🙂
Empress Constance, what kind of advice would you have for a beginner, part-time, or closet sissy who didn’t really have the freedom to blatantly express their inner femininity? Are there little, not so obvious tricks or touches?
Regarding Gummy’s comment, I completely agree with everything that he said… Except I am going to have to admit that I’m not as strong in the character department. For some reason I just love trashy. I can’t help it. And I have no idea if its because that appeals to me as a man, or if its something I want to identify with… But I cannot deny that while I love the powerful, dominant, intelligent and classy mistresses of LDW… I also have a soft spot for trashy :-p
HI Nb and thanks for the comment……….what I tell my callers and sissy wannabes is there are many things you can do in your every day life to help bring a bit of girly in….panties under your work clothes is a perfect way to feel fem all day or stockings even a tad bit of clear lip gloss and using fem shampoo and body wash. There are all very subtle ways to bring out the inner feminine in anyone without being exposed and called out for being sissy. And as far as your other comment hey whatever floats your boat classy or trashy its allllllllll good 🙂
This evening I had a “dressing” incident that I think helped me relate a bit more to this post. As I prepared my evening ensemble, pulling my soft woolen sweater over my head , I discovered I was wearing it ‘inside out and backwards’………….It seems I had been ‘crossed’ up dressing …and boy did I feel ‘trashy’ 🙂
cuckie this was very funny LOL I recall a time way back when that I wanted to stick you in panties hmmmmmm maybe I still should LOL
Oh i really realy loved this, i cant understand that i dont have seen anything like this before, I always wanted to be elegant, not slutty, so finally i found something for me to read aswell, ofc i do like other girly things aswell, but this is more like me, elgant dress in shiny material either pink, red or black or like that, just not intense colors but still very colorful dresses, with strass, ( glimmering stones ) attached or like that, such as there are in promgirl 🙂
Lovely
This is more of a dream to me, as in a ballgown or prom dress or wedding dress, and its not just a fantasy, i want this for real
I am so glad that you can relate to this. I find myself always discussing the slutty side of cross dressing and sissy girls and this is something I wanted to share because as with many of you I am not just one thing or a one trick pony I have many many sides to me. I wish for you to have all your dreams come true thank you for taking the time to comment and express your sissy desires!
Curtsey Empress Constance, I’ve read with delight and pleasure your blog comments. I certainly hope from what you described, that Connie had a wonderful evening out. I agree that a girl does need to start preparing for her evening out with a bubble bath. I happen to love Lavendar as it’s real relaxing. I also suggest to light a candle and then put on some soft sensual music to listen to as you soak. Let those thoughts out, begin to feel totally feminine. Feel feminine from the inside out. Envision slipping on those panties and bra. Envision sliding up the hose up those lovely smooth legs. Then, envision putting on the make up, and applying the makeup to those georgous cock sucking lips. Envision these things before you step out of the tub and dry off. Then as you step out and dry off, apply some soft, smooth body lotion, think of your self as a lady getting ready for a evening out. I agree Empress Constance, as you apply the makeup, think “Classy, Not Trashy” Totally agree in selecting just the right evening gown, as you shop, look at the dress and envision yourself in that dress, and if you are brave enough, ask the sales girls for permission to try on, but do it in a respectful way. Just think how a lady would ask to try on. Don’t worry about them saying no, but at least ask. Then if you think, you’ve selected the right dress to fit your form, go ahead splurge a bit on your self, and think of the enjoyment you’ll have as a lady on the town. Geee Whiz, I think I could go on and on,…but hope this helps anyone out there. Thank you for posting Empress Constance.. Curtsey
Steph thank you for your long thought out comment! I have had the extreme pleasure of seeing and enjoying you and I would say your not only classy but sassy as well. Thank you for the extra tips to create that feminine state of mind one needs for dressing up your awesome! Thank you for being the classy sexy sissy girl you are and being a true sister to your fellow cross dressing and sissy girls on our site your amazing and one of a kind!
Curtsey Empress Constance
Awwww, I’m blushing by your response and saying that I’m classy. I agree, I may also be sassy to on occasion, I suppose that’s because as a girl, I have that perogative from time to time to let my hair down. Thank-you Empress Constance for your very kind thoughts. I happen to believe and feel that you’re a awesome lady and Mistress always have always will. I’ve always have been sensitive which is why I truly feel and believe I am a girl inside. I’ve also have always been told to follow your heart and follow your dreams. I’ve been trying to do both for a long time… let me tell you it’s not easy…ma heart gets broken more times that I care to even think about. But, I always try to stay true to my nature. I feel that no matter where your lot in life is, it’s always much more nicer to help others. I suppose, I just step to my own beat…..which I feel is always better to be your self and not put on airs for anyone. For the possible sissies out there….either new or perhaps you’ve been a sissy for a while….I;m always glad to help…and you’re in the best place for having someone that understands…From Ms Ally, to Ms Tia, Ms Dallas, Empress Constance, Emperss Hunter, Mistress Ann and ALL the LADIES of LDW….Cursey Empress Constance…
wow a very nice reply to my reply steph thank you and yes ou are classy and a bit sassy I totally get the letting your hair down side hehehehehe and steph your one of the sweetest people I know I have no doubt your sensitive but that never gets you down for too long you are a ray of sunshine and I am glad you’re following your dreams of being a woman and all your other dreams you know the ladies here support you and will cheer you on! Thanks for the awesome comment honey