Ask Windy Cissy

If you're a guy who has always wondered what it would have been like if you'd been born female, this advice column is for you. From shopping to shaving, makeup to mannerisms, I'll share with you techniques that have enabled me to pass convincingly as a woman, time and again. You'll learn what to do, and what not to do, as you explore your feminine side. So go ahead, let your inner woman out! All reasonable questions will be answered. Ask Windy Cissy at

Wednesday, September 12, 2007

Get The Monkey Off My Back

Dear Windy, I don't know where to start…all my life I have dressed in women’s panties and felt like a women. I would like to do it as recreation or go to parties dressed like a women, it’s a hidden secret that I'd like to keep but I feel like telling people and getting that monkey off my back. Can you help me understand why I feel this way? I love it, please help me, Art

P.S. You look wonderful by the way

Dear Art, First, thanks for the complement, you made my day! As for why you feel the way you do, I’m not into psychoanalysis but take it from me, you have plenty of company. I can help you fulfill your wish to come out to friends while keeping your secret: take a look at the calendar, Halloween is right around the corner! If you’re not already invited to a costume party, why don’t you host one, and make sure the invitations encourage everyone to wear a far-out costume. You have plenty of time to put together a complete women’s wardrobe, and Halloween is the perfect excuse for shopping for a wig, makeup, etc, so go for it! Windy

Thursday, September 06, 2007

Getting a Girlish Figure

Dear Windy, I have been crossdressing since I was 10 years old. I've always been big in stature: I am 5’11” tall and I currently weigh 235 lbs. I have decided that this year I’m going to be going out en femme. The very first time will be to a party in December. I've been working out but I've stayed away from weights as much as I can. My wife is very supportive. We go jogging and biking together, and I have started going en femme. I was wondering if there are any exercise routines or videos that I can use to get my weight down to a feminine size? Are there any diets you can recommend? Jessica

Dear Jessica, Well, you've got your work cut out for you, girlfriend, but you are so lucky to have such a supportive wife! Your ideal weight as a man is 166 lbs, and your ideal weight as a woman is 156 lbs, either way you've got to start eating less and exercising more...sounds simple, doesn't it? You will want to start an aggressive cardio program: jogging, walking and especially swimming is a great way to burn calories and lean out your body. Of course you will steer clear of lifting weights for your upper body, although I recommend lots of crunches to trim your abs. Get one of the old Jane Fonda workouts if you want a good burn! As for diets, doctors cringe but I always kick off a diet with a 24 hour fast which shrinks my stomach so I don't need to eat as much to feel full. Although it is much maligned by health professionals, I swear by the old Beverly Hills Diet as an initial kickstart: after your 24 hour fast, eat nothing but a pineapple the next day, sounds crazy and I don't recommend it as a continuing diet! Just make sure you eat three meals a day only watch your portions, and one other thing: I have had great success eating only dairy products for lunch, check out the Dairy Diet. There is no magic to this, I've done it and so can you! Windy

Saturday, June 23, 2007

Creating the Perfect Ponytail

Dear Windy, Could you direct me to a pic of your ponytail hair style? I would love to see how you do that. When I wear a wig, somehow I have never been able to make up a realistic appearing ponytail. It could be that I am not very good with wigs.... My own hair is long enough to wear a real ponytail, but my forward baldness does keep me from looking as feminine as I would like. ...I like the reasoned and practical way you seem to approach the "crossdressing" aspects of your life. Rickie

Dear Rickie, Wearing a ponytail is a lot of fun, and it's a great way to overcome bad hair days when you're wig is in a bad mood....the trick is to use a scrunchie and plenty of bobby pins: brush your hair behind your head and pull it into a ponytail, wrap the scrunchie around it twice, then grab the ponytail in both hands and pull apart slightly to force the scrunchie up as far as it will go. Next, tuck the loose strands back and pin them liberally with plenty of bobby pins until you have the look you want. Of course, you may want to create bangs with the rest of your wig, and when it looks just right finish it off with a little hairspray. Here's a link to a picture of how it looks. Windy

Sunday, August 06, 2006

Hair and Nails

Dear Windy, It would be great to get your ideas on couple of issues. I spend five days a week working in an office and this forces me to be dressed in drab. The weekends are spent mostly dressed, I have the most wonderful wife and she understands who I am. Question, is there a hairstyle that can be switched from guy to gal? My hair is gray/white, turned very early in my life. I have considered coloring and that is something that I am leaning to. But that still leaves the problem of length and cut. Second question, how about nails; how far can a girl go with keeping nails on the long side with clear polish before being noticed? Love your site. Josephine

Dear Josephine, Windy Cissy is a wig person, but here is a website that has some interesting links to hairstyles that might work for you, depending on the length of your hair now. As for my nails, I keep them on the longish side all the time, and file the edges to make feminine ovals whenever I'm dressing. If I'm switching back and forth to guy mode, I just take the polish off them and flatten out the tips a bit when I'm a guy and nobody seems to notice. By the way, congratulations on having such a wonderful, supportive wife, you are one lucky girl! Windy

Thursday, January 26, 2006

Some Questions About My Son

Dear Windy, I have some questions about my son. One search led to another and I wound up on your site and saw your email address. You seem like a very nice person and I'd like to ask for your advice if you don't mind. Two years ago, when he was 12, I came home early from a date (single mom) and found him dressed in my clothes and smoking my cigarettes. I lost it and became hysterical. I grounded him for four weeks after I calmed down but we never really talked about it because we were both too embarrassed (or at least I was). I stayed home from work today to do a little spring cleaning. While cleaning up his room, I found several pieces of my clothing (bra, panties, slip, nightgown), two packs of my cigarettes (one was open), a lighter, ashtray and several wadded up pieces of aluminum foil filled with smoked cigarette butts.I didn't remove anything and I didn't tell him what I found. I was disappointed but I wasn't surprised. I had hoped this was a phase but apparently its not. I'm not proud of the way I handled the last situation. I haven't confronted him yet because I want to do better this time. I want to ask advice from someone who has been there and done that before I talk to him. I want to be more open-minded and compassionate than I was two years ago. Sharon

Dear Sharon, My heart aches for you and your son, but you have the opportunity to reach out to him and I'm going to try to help. I think of myself at his age, how I would have reacted if my mom found me out, and I guess the best thing I could have heard would have been something like this: "I've always been bothered by the way I reacted when I saw you dressed up that time. Please, let me finish: I've done some reading, and there is nothing wrong with wanting to experiment. In fact, I think it's kind of cool. Some day, will you let me help you dress up? You would make such a pretty girl, and I can help buy your own things, so you wouldn't have to try on my frumpy old clothes. Do you want to try it sometime, just for me?" He may try to pretend that he isn't interested, if so let it pass and bring it up again before Halloween. As for the smoking, I do think you should tell him how bad that is for him: you can distinguish between harmless dressing up and harmful tobacco. I know this will be hard, but if you wind up losing a son and gaining a daughter, you may help her find happiness. Chances are, your boy is like most of us, a straight hetero guy who digs the rush from dressing up like a girl, and if you can share in his joy from this, you will be closer than most sons and mothers can ever be. Windy

Thursday, September 22, 2005

I Want To Be Me

Dear Windy, How do you know if you are passing all right? What is the worst thing that has happened to you when you did not pass? How do most people treat you up close when you talk to them? Do most people accept you if they know you are a guy? Can I just be me and if I go out dressed and look pretty good, will people accept me for being me or will they make fun of me or want to beat me? Will cops harass me? What bathroom should I use? Should I get laser beard removal so I can pass easier? Will I ever find a woman to love me or do I have to just date men? Please help, I want to be me. Beverly

Dear Beverly, Where do I begin? You know you are passing if people don't stare and laugh at you. The worst thing ever to happen to me? A woman outed me in a hotel restroom and sicced a security guard on me! Most people treat me like the person I seem to be, because I've gotten pretty good at passing as a woman. If you go out dressed but are obviously a guy, you will probably be OK in Greenwich Village or Castro Street, but not on Main Street USA. Cops will leave you alone unless you do something stupid like use the women's rest room (see above). I can get by with a super close shave. Unless you are gay, do not seek a man to love, search for a woman who can love you for being yourself. Windy

Wednesday, June 22, 2005

More Beach Reading

Dear Windy, I loved The Danish Girl and The Jessica Project, can you recommend any more novels with crossdressing themes? Bookworm

Dear Bookworm, I just finished Skylord, the sequel to The Jessica Project, and it's a good read. Lots of flashbacks to The Jessica Project, and a few scenes with the hero/heroine in female disguise. Not as much crossdressing as in the first book, but the same characters and a fun story. Windy