I do enjoy being a sissy mostly just the sexual side of acting female though, if you're scared of getting caught i assume you also wanna mostly just be a sissy in the bedroom am i right.
Well if yes there are 5 things you should probably own and I'll list them in order of importance.
1. Panties, almost every tease on the site that is about feminization/sissy stuff makes you wear panties, plus its very girly clothing you can hide and wear anywhere, if your really committed to being a sissy you could even throw out all your male underwear and replace them with panties and no one would know.
2. A Bra, more female clothes often used in teases you can also possibly hide under your normal clothes, you can even fill it with things like paper towels or toilet paper or water balloons to give yourself some cheap fake breasts, and if you want you could give a dildo or real dick a boobjob with those tits.
3. A Dildo, a lot of feminization/sissy teases will make you suck a dildo (One of my favorite things in teases) fuck your ass with a dildo or make do both, possibly at the same time, i would suggest for a first timer make sure the dildo is thin because a short thick dildo is more painful to fuck you self with then a thin long one. Of course to me it makes sense for dildo play to go hand in hand with being a sissy, pretend you're sucking cock or taking it in your ass or as some like to call it their boypussy, and i find it very fun to suck my own cum off of my dildo.
4. Lube, very important for anal especially for new comers, if tease makes you do anal things but does not bring up lube, use lube anyway, if you get very experienced with anal play your own cum alone might do the trick as a lube replacement but not until your ass gets used to getting fucked.
5. A chastity device, it's popular in a decent number of sissy/feminization teases and there are sissy's who love chastity and you may be one of them, not really required but a lot of people including myself like chastity and as such a number of sissy teases incorporate it because it can keep you horny while your sucking dildo or taking it in the ass and losing access to your cock is the best way to make in somewhat feminine.
Lipstick, pantyhose and stockings are also popular feminization items but not nearly as much as the above 5 items, plus these items are mostly just for looks but cock/dildo sucking might be funner for you if you see your lipstick marks on it.
For teases i recommend this.
https://milovana.com/webteases/showflash.php?id=12099
Choose Jenny/Humiliation, it has some sissy stuff and not so sissy stuff so you get a variety instead of sissy stuff and nothing else. If you want just a sissy tease and are fine with the somewhat questionable themes i made a tease that is good for some simple easy sissy stuff.
https://milovana.com/webteases/showflash.php?id=25968
It' says to use have a chastity device but enough self control to not touch yourself for 24 hours also works.
Hello every one! I'm very new, and am looking into maybe becoming a sissy, but I don't know where to start. 
Can anyone please tell me a good webtease here that would ease me onto being a sissy? Or you could just /tell/ what to do, and skip the the tease alltogether. 
That fact scares me, but I know it's true. If you are willing to take on a boy, train me to be a sissy, but are willing to accept that I might quit because I find that I don't acctualy find the prospect inticing, please send me a PM. 