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Crossdressing, Stealth-style, Tips to Let Your Inner Sissy Out

Express Yourself, (even it is only to yourself)

Ok, you found this. Thanks for reading. I am new to this site but after reading some of the great stuff here I am motivated to add my 2 cents and try to help my sisters out a bit. This is about dressing femmy as often as you want to but in what I call, "Stealth Mode". That means you wear what you want to the point of self expressing as femme but make it as hard as you want it to be for observers to notice. That is as opposed to either being very openly femme in style or being more discreet but still allowing anyone that cares to look at you to be able to tell you are a guy in girls clothes.

We will start with what I do. I of course am a cd, sissy, tv, tg, gender gifted, or whatever term you feel comfy with. I enjoy letting my fem side out. Like most guys, I reached a point of "critical mass" where I just had to do more a couple years ago and maybe if you know more about what I do, you may want to emulate me and find more peace and relaxation in your life.

  Typically, I don't have to appear in average male clothes very often so I spend the huge majority of my life dressed en femme. You may not have a schedule that permits that luxury but you can use these tips for the time you do have.

For my jeans, I wear womens jeans exclusively, I like mine skin tight in either bootcut or skinny straight. I wear womens tops. They can be long or short sleeves, varying necklines, and as simple as a tee shirt or tank top all the way to very femme blouses, If it is a very femme blouse, it is covered by something. My shoes are all fem sneakers, often the new Shape ups which are supposed to exercise your legs and butt. Or they are fem sandals or flats or boots. This past winter I even wore regular high heel pumps a lot because I wore my overshoes over them in the snow. Under it all is a full set of lingerie. I only own panties as some of them are perffectly fine for anyone to see without being able to tell they are not men's. I always wear nylons or pantihose and this last year or so I stopped wearing socks to cover them. I wear any color I am in the mood for or that co-ordinates with my lingerie or clothes from skin tone sheers to heavy tights. I often but not always wear a bra. Lately, this just past winter, I was even wearing falsies in it. I wear a camisole usually, and usually one that is seamless because I usually wear a cincher over it. So that is an overview , and my intention is do a capsule here on each item of apparel I wear in stealth mode. now here are some details.

I mentioned jeans first so I will start with them. Then maybe do a capsule on each other item on clothing.A lot of my jeans came from Salvation Army or Goodwill and other thrift shops. They are a great place to feel very comfy shopping where you can try on anything you want but if you don't want to do that they have weekly sales where one can buy a nice pair of jeans for just a buck. What that does is allow you to buy several sizes and if they are not what you want you can toss them or donate them back and only be out a tiny bit of money. I generally buy mine in anything from a size 0 to a size 4 and it all depends on the brand and the cut as to whether they will fit. For guys, the trend of the last several years which now seems permanent, of women having low cut jeans, is a great benefit to allowing guys to fit into skinny jeans. For example, a guy that can get into a low cut in a size 4 would have to have at least a size 8 or 10 to get into that same jean if it had a high waist cut. Then the jeans would appear baggy in the butt and the hips. That same guy in a low waist size 4 could have the butt nice and smooth and no bagging at the hips. Also, keep in mind to go a bit bigger if you plan on wearing a padded butt or hip girdle under them.

Other benefits of starting at that kind of store for your fem jeans are that they are usually washed and done shrinking so the fit is stable. You can find really gorgeous, cute, expensive ones often. Also make note of the length, That is easy to do by holding them against you with you holding the bottom of the crotch against your crotch bottom. You want them to be long enough which for most guys means finding the size in a tall or medium as opposed to a short or petite.

Another stealth factor is the side the zipper or button fly closes on. Men's jeans have the opening on the right like our shirts and so do very many women's jeans. I used to be a stickler for having the zipper on the "guys side" but now not only do i not care much, I also like to find some with the zipper in the back or on the side. We can get away with it easily by just wearing something long ehough to cover it, whether it be a sweater, coat, or top etc. Also note the pockets. I always put my hand in them because womens pockets are generally much shallower. It depends on what you intend to put in them. If you carry a large wallet in your rear pocket and intend to keep doing so when wearing your new fem jeans, you have to be sure the pocket is big enough. If you carry your cell phone in the front pocket you have to be sure it fits without falling out and that you can get them out of the pockets while wearing the jeans if you are going for tight fem fit. 

To maintain the stealth mode you have to be observant of other details too like pink stitching or a very fem name stitched on the back pockets or a bright fem tag. You also have to be sure there are back pockets if you want them. Lots of fem jeans don't have them. I wear those sometimes too in stealth mode by either carrying my wallet in my front pocket or coat pocket or in a purse worn under a coat. If you fall in love with a pair that has some femme details , you can often modify them. If you are in love with a pair and have to let down the hem to make them long enough, be sure they are not too worn out at the hem. Sometime you let a hem down and you find a big ring of wear that goes all around the cuff and looks bad. Also a lot women wear out their jeans at the rear of the cuff hem so if you let it down you find a big hole or gap with no material. I have removed pink tags, rhinestones, let down hems, and etc to make a pair work for me and you can too. Since many jeans come new with holes in them, you want to notice if the holes are so big that your nylons or your panties will show and decide for yourself if you want them to. Sometimes I wear a pair of jeans that has a hole in the butt with a pair of bright red lace panties peeking through.

   Keep in mind too that a lot of what seems really like it would be too obvious is taking place in the wintertime here in Boston so that gives me much more leeway in what I can wear in stealth mode, like wearing falsies in my bra.  Also I shop in all stores not just thrift stores but all the same rules apply item-wise.

   And more on sizes: Using the example given above in which a guy in a low cut size 4 has to have an 8 or 10 in a high waist cut version of the same jean , some guys may not want to wear skin tight ones or maybe you want to just wear fem jeans all the time but only skin tight ones when you are in a more femmy mood. In that case, you go up a few sizes and/or get a style that is not designed to be skin tight and then it appears as if you are just wearing typical guys sloppy fitting jeans and you can wear them anywhere as long there are no overtly fem details on them. Be aware of the style of the lower leg . Big flares are too outre for stealth but boot cut and straight and skinny can all work. Currently a big trend is what is called "jeggings" which are just leggings so combine the word jean and legging and get jegging. They are made of jean denim so they often just pull on and often have no zipper or buttons or pockets. Again, in the winter , one can go stealth in them but in the warmer weather it is tough to hide them.

    This past winter I also branched off from jeans to womens pants. You can too and still go stealth. Women's pants come in a lot of colors and materials that closely resemble men's dress slacks. Stick with the common guys colors like blacks and greys, and browns and greens and blues and note that virtually all of them have the zipper opening on the fem side or a side or rear zipper. Usually no pockets and don't get fooled by the fake pockets a lot of them have. Again if you buy low waisted ones, you can get into smaller sizes if you want a tight fit. Also lots of them have just an elastic waist which allows a lot of fit leeway too. Guys can wear the wide cuts, the skinnys, the casuals and etc, in other words virtually all of them in stealth mode as long as the top of them covered to about the bottom of your butt. And don't forget the fun-to- wear yoga pants and womens sweat pants and workout pants. If you are vacationing  or just in a mood for fun, fem, summerwear, you can get a pair of white jeans or cropped wide legs and in some really cool and comfy materials like linen or gauzy fabrics, 

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    Lastly, even if you get some jeans that are a bit big in the waist, a belt can take care of that and give you an opp for yet another femme wardrobe addition, women's belts. I have some that I can even wear with a men's 3 piece suit and some that are pink or have jewelled buckles and etc. I think stealthy belts are pretty common sense so I won't go into them here except to note that they usually go in sizes like S, M, L instead of numbers like guys and of course the size you need changes depending on if you wear it on your waist or your hips. I will add more about them when I do a capsule on accessories. I will come back and edit this capsule when I think of more to add and suggestions are welcome. If you are just getting started being girly, you will really enjoy the superior, soft, sexy feel of the cloth they make women's clothes out of and it will hook you like a drug. Shaving your legs will only enhance the feelings more. So go out and give the economy a kick in the ass by spending some money on some nice pretty clothes and you can keep it our little secret if you do it in stealth mode. Express yourself !


Kathleen D. on March 08, 2016:

I wouldn't want a guy that I'm dating to wear anything outwardly female, but I love to get a guy to wear girly things underneath his guy clothes. I have had a lot of boyfriends over the years and I've never failed to get a guy to wear things for me if I date him for more than a month. If he will wear a bra for me then I know he is dedicated to me. I live in the conservative Davenport,Ia. area so I love the challenge. I sometimes work as a bartender and I have occasionally noticed couples where the lady gets the guy to wear things underneath. I loved putting my hand on a guys back when I knew that his girlfriend had a bra on him. I just smiled and never said anything, but I always looked forward to having them come in the bar.

boy on April 19, 2014:

back zipper jeans are great

leo on April 05, 2013:

I like and wear back zip pants too, as a man you can wear girly clothes.

Mikel on February 23, 2012:

I love wearing ladies pants, especially side or back zip styles. They're hard to come by, but I have some back zip jeans. I'm really into being embarrassed as a sissy in public and love the giggles I get from ladies as I walk through a mall or public place. I sometimes like to wear a bra under something that is just sheer enough to show through at close distance. I was totally humiliated by two girls at a grocery store one night.

jenisis on November 14, 2011:

I am also a guy that likes to wear and blend clothing,shoes or boots of both sexes, and sometimes fully crossdress. I also have my hair cut into women's chin-length stacked bob, pierced ears,and sometimes wear makeup.

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