However, for the vast majority of us, that's just plain impractical. We have to hold jobs that won't allow that, or have to keep it a secret from family members and friends that won't understand.
Over a decade and a half I've compiled a number of ways to be as sissy as you can be and not "out" yourself to your friends and co-workers (but people living with you, such as roommates/spouse ect will know).
I do all these things myself, and have for around a decade now (after spending a while refining and adding to the list,)
1. Panties. Women wear panties every day. Now you do. Toss every last single pair of mens underwear you have. End of story. If you want to keep a pair for going to the doctor: Don't. He's a professional and bound by medical ethics and Federal law to not tell anyone (and I've got a cousin who is a Nurse in a Hospital ER, she can't name-names because of those rules, but said that way more males come into the ER in panties than you'd think, around 5% to 8%, so the doctor WILL have seen it before). Go to the store and buy at least two weeks supply of panties. In my experience, briefs and hi-cuts are best for the male anatomy. While you can definitely get some nylon, satin and microfiber panties, be sure to get some plain cotton ones. If you're having to do anything strenuous (yardwork, exercise, ect.) you'll want cotton undies too. Women know this lesson well, learn it yourself too. I avoid lace panties personally, because the lace usually doesn't react well with the male anatomy in my experience. "Boyshort" panties are also out, in my experience they are actually rather uncomfortable to be worn by a boy, just the way they are cut and your anatomy will fit into them.
2. Diapers. You wear diapers to bed now. Sorry, but can't risk you wetting the bed :-) Go out and buy a pack of "briefs", those adult diapers that are basically sized-up baby diapers. I've found that the CVS store brand is a good combination of easily available, affordable, and suitable quality. Avoid pull-ups unless the whole toddler-in-potty-training thing is your specific kink. Every night from now on, when you get dressed for bed, you WILL put on a diaper and make sure it's taped tight. For 8 hours you are diapered, and if you need to relieve yourself, you're doing it into the diaper. For me it's from 10:30 until 6:30. If I wake up in the night and have to go, it's the diaper for me. If I wake up in the morning and need to go, it's the diaper for me.
3. Nighties. The only thing you're wearing over that diaper at night is a very girly nightie. I prefer a satin chemise, but any sleepwear that is extremely feminine and totally emasculating will do. You should be able to look in the mirror and see a total sissy girl. If your nightie doesn't cover your entire diaper, so much the better (but it's not required).
4. Periods. You've got one now. Part of the whole "girl" thing, you're about to have your first period. Get a calendar, plot it out, you're on a 28 day cycle and for 5 of those days you're "riding the cotton pony" as they put it. There are plenty of online planners/tools to help you. Go buy some pads. I do NOT recommend tampons, as the health risks of anal insertion are way too high. Once you are in your period days, when you change out of your overnight diaper, put a pad into your panties. Change it every 4 hours. If you're at work, that means discretely keeping a pad or two around for changes. I'd recommend thin pads. Being discrete with hiding your pads and changing them is another part of the whole girly experience. So is the inconvenience of having to change them. At least you don't have to wear an overnight pad, you've got a diaper for your period at night. As I write this, I know I start my period tomorrow, and I went to the pharmacy to buy some Always Infinity (my preferred brand). Having a preferred pad is VERY femme. Guys don't know anything about pad brands and styles, girls do.
5. Pee sitting down. Should go without saying, but your days of standing up to pee are long gone. No pulling down the front of your panties to pee at the urinal or into a toilet. Take a seat, little lady! I haven't peed standing up since 1999, it's even to the point that on a camping trip, I squat in the bushes like the girls do.
6. Shave your legs. Another part of the whole "girl" deal, you're shaving your legs and keeping them bare. If for some reason you don't feel comfortable with exposing your shaved-bare legs with shorts in the summer, shave them for the first time on Labor Day, and stop shaving just after Valentine's Day to let your leg hairs grow back so nobody will know better during the spring and summer.
7. Paint your toenails. What co-worker or friend is ever going to see your toenails? Those little tootsies should always be regularly pedicured and kept in a very girly shade. Pinks, reds, and light blues and greens are good.
8. Bras, sometimes at least. Yes, I know you can't easily hide a bra under many clothes. However, at least one day a week you should wear a bra. During the winter it's much easier to do under heavy clothes, so it's easier to hide during a workday. Otherwise it's a weekend day. If you want the "little girl" effect, a bralette is pretty dang close to a training bra, and the Justice chain for tween girls carries actual training bras in up to a 38 band (but you usually have to order them online).
9. Be a girl online. Social media is your friend. You can be whoever you want. Set up a Facebook and Twitter account in the name of a femme alter ego, join girly groups, play girly facebook games. The minimum age in Facebook's Terms of Service is 13. So, on Facebook and Twitter I have an alter ego that's a 13 year old girl. She's a homeschooled girly-girl who is into all the various teen idols and still loves Disney Princesses. I have to actually mentally get into a different mindset to type like like a 13 year old girl instead of a thirtysomething male, definitely helps with the sissy thinking.
10. Work out like a girl. A girl has to stay in shape. Yoga, pilates and various aerobics are your friends. Buy some workout DVD's. At least one girly exercise outfit is good too, unless you're planning on working out in just your panties and a sports bra. Work on toning those legs, you want toned and shapely, not ripped and muscular. If you're a little oversized, this will help get you in a girly shape over time. Personally, I wear a white sports bra and cotton panties, a pair of pink women's running shorts, and a pink T-shirt to exercise in.
