Monday, September 28, 2015

The Fine Art of Tucking (NSFW)

For me, tucking has always been an obsession. Well, not an obsession like I think about it all day, but rather a priority - an important priority when I’m attempting to look like a girl. To the uninitiated tucking is the term for when a guy tucks his genitals back between his legs so he can wear women’s clothing without any telltale bulge that would reveal to the world that he does not in fact have a vagina, or rather an smooth mons pubis if you want to get technical.  Any time I get dressed up I want to look like I have a vagina, more than that, I want to feel like I have a vagina. The more securely I’m tucked, the more comfortable I am and the more fun I can have. 

When they first hear about, people seem to think that tucking would be uncomfortable or painful, but it’s not at all if you do it right. A good tuck feels comfortable and secure. In general, it involves pushing the testes back up into the body, which, once you get the hang of it, is a quick and simple procedure. Once they’re in place, it’s a simple matter of securing the empty scrotum and penis back between the legs as tightly as humanly possible. You definitely want to make sure that no little piece is hanging out or coming loose, because that actually can tug or pull or be uncomfortable. That’s why it’s important to do it right. 

When I first seriously started dressing and going out things were a little tricky because I was sixteen, lived with my parents and the internet wasn’t quite yet a thing. There was no option back then to go online and buy a product or watch a how-to video. Improvising was the only way to figure things out back then, luckily when to came to crossdressing I was a regular MacGuyver, and so I improvised my very first tucking method, and I understand other people, in similar situations, have done the same. 

So for me, it started with a shoelace and a twenty-five  inch piece of cotton cloth that I cut from an old pillow case. First I’d stand there, naked as the day I was born, and tie the shoelace tightly around my waist. Then, I’d fold the cloth into a strip about four inches wide, then fold it over the string lengthwise, much like a loin cloth. With my right hand, I’d maneuver my testes up inside me, grab the rest, bring it back and then pull back as tightly as I could on the cloth. Then, when it couldn’t get any tighter, I’d tie the cloth in the back. Thinking about it years later, this must have left a small lump of a knot in the back, but I guess as I couldn’t see it, it never really bothered me. 

This system worked for me for years because it’s pretty comfortable and does produce quite the tight tuck. Unfortunately, it does have its drawbacks; mainly that it tends to be kind of bulky and is quite complicated to take off or put back on again. It worked for a while, but wasn’t perfect, so over the years I kept working on new methods.  

Moving to New York in my early twenties helped me to simplify things greatly, mostly because I found myself much more comfortable being out shopping for things like women’s underwear. In suburban Georgia, where I’d grown up, I knew people who knew my parents, and well, I was always super nervous. In fact, the only thing I could really do to shop without nerves, was to go to Wal-Mart at 3am - and if you’ve ever seen a Wal-Mart at 3am, then you know that a teenage boy buying lingerie is hardly the strangest site to be seen. 

Years before gentrification brought organic coffee, farm-to-table meals and trendy boutiques, Astoria, Queens was a humble working class neighborhood which suited me and my then-budget just fine. Every working class neighborhood in New York City has the same basic stores, including cheap, slutty women’s clothing outlets. It was in these that I discovered the wonder that is the two-sizes-too-small super cheap cotton thong. It has to be cotton, because fabrics like lycra or spandex have too much give and tend to stretch. No, they have to be tight if you want a proper tuck. Using basically the same method as my cobbled-together loincloth, you put on the thong, hold your junk back, then carefully make sure you’re grabbing everything as you pull the underwear back and tight. You definitely don’t want a bit of skin sticking out the side. That’ll bother you all night. Sometimes this can take two or three tries to get it just right, but once you’re set you’re good, smooth and secure with no additional hardware required. It’s a good method, especially when combined with my homemade hip-padding system, which is all contained within pair of pantyhose with the legs cut off.  

Over the years, I’d heard of people using duct-tape and like many people I cringed at the idea of sticking duct tape not only to my skin, but something as sensitive and delicate as my boys. So, the first time I tried it, I first cut off the toe of a pair of pantyhose and put my penis and scrotal skin into then wrapped that with a strip of black duct tape, to make a little tube. This tube, I stuck back between my legs, then I grabbed a six-inch strip of tape and taped the tube down. Looking in the mirror, it appeared to work with minimal fuss. At least for a few seconds, before the strip of tape came loose and the tube flopped back into place. It turned out duct tape is a little more complicated. 

For my next attempt, I held the tube back, then ran a line of tape from just a few inches above where my penis would have been, all the way back, carefully keeping my buttocks apart, then secured it up to the small of my back. Luckily, it held, but sadly, there was still a bit of bulge, because it wasn’t holding my testes up inside my body. They were threatening to come loose and fall. So, I did one more long strip to the right of the first, then another one to the left. For good measure I added another down the center, then finally finished it off a couple of three inch strips; one across my shiny new mons pubis and one across the small of my back, just to make sure the other four long strips stayed on. This time it worked and everything held. 

Duct tape actually works quite well and you can wear it quite comfortably for an extended period of time. The tuck is so secure that you actually wear a bathing suit or lingerie without even the slightest hint of boy parts. It’s even fairly waterproof if you want to take a swim (though I never actually have). For a while, they even made a clear duct tape, which provide not only a super-secure tuck, but also managed to be quite discrete even if you wore nothing at all. Unfortunately, the clear tape had one drawback, which was that it left a gluey, sticky residue that I couldn’t wash off for at least a week. Luckily, at the time I was single, so it wasn’t too embarrassing. 


It’s not just clear duct tape that has its drawbacks. While it’s good for long-term wear, it’s not so good if you need to pee, what with the above-mentioned waterproof qualities. It can be done, but I wouldn’t recommend it. On days when I’ve worn it I’ve just tried to consume as few liquids as possible, which is good for a photoshoot, but not so great at say, a bar. Secondly, duct tape tends to be a little inflexible and it can fight you when you move. Sometimes you can even hear it squeaking when you walk. But the real deal-killer on duct tape has to be the awfulness of trying to get it off.  It can be painful, to say the least. It helps if you’ve shaved everything, but even then there are times it just doesn’t want to come off. There have been times I’ve been in pain, pulling the tape a centimeter from my skin, then working a pair of scissors into the gap so I can painlessly cut each hair that’s being ripped out but refusing to give up its roots. Needless to say, taking off all that tape is quite the process and one I certainly wouldn’t want to do in company of anyone at all. It’s a painful, awkward solo mission, and one where sometimes you stop for a breather, have a drink and check your email, naked but for the long random scraps of duct tape still clinging tightly to your nethers.  

Now that we have the internet, it’s easy to share knowledge of what works and what different people, all using just their wits and basic household materials, have invented. There are other methods I’ve heard of people using, but have either never really tried or have never worked for me. Some people recommend medical tape instead of duct tape, but I’ve never found it to be strong enough. It just slips right off. Maybe they have stickier skin than I do? Who knows, but it just wouldn’t work for me, even though I’ve tried a few different brands. Once I read that early transgender pioneer Renee Richards used fishing line to tie everything up and back, in a manner that I think must have been similar to my shoestring and pillowcase method. Of course, it sounds quite painful, and I’ve never heard of anyone else trying it, not even in the fetish community. 

There’s one infamous method, always discussed in hushed and fearful tones. It shows up every so often on crossdresser message boards in the form of an how-to guide. The text is in Japanese, but there are helpful photos illustrating each step. What one does is push the testes up then push the penis back between the legs, then pulling the scrotal skin up on either side. Surgical tape is applied to hold the penis in place, and then the scrotal skin is folded back on top of it to create pseudo-labia. One then applies superglue to the seam between the lips and is left with a faux vagina that, at least in the photos, quite surprising realistic. Supposedly this method is used by all those fabulously petite and impossibly beautiful Asian performers, but I’ve never heard of anyone actually attempting it. 

Well, at least until I did. Sure, it’s super glue and you wonder if it will come off or burn or something else even more horrible and best left to the imagination. But, maybe a small price to pay to make people think you have a vagina. Plus you could wear it all day, perform all your necessary bodily functions without having to undo it and you could definitely pass in a string bikini. You could probably even swim too. But, at the time, I was rather impressively single, so I figured if it got stuck that way until the glue wore off, no one would see anyway. And maybe I could go to the beach. 

Laying down on the bed seemed the best way to do this so I set myself down with a tube
of superglue and a roll of one and half inch duct tape and set to work. Ball up inside. Okay. Penis taped down. Good thus far. Next, I carefully sculpted my sack into the best version of labia majora that I could. Looking down, it seemed to be working. Everything was fine and the area between my legs actually looked like I had a pretty decent pussy. Starting with the front, where my clitoral hood would have been, if my genes had shuffled differently, I ever so carefully applied the glue, stopping every centimeter or so to hold the two halves together for a second to let it dry. A finger or two got stuck but I was able to pull them away and then a few moments later I was done. Not only was it fairly easy, it was also pretty quick. The whole operation had taken less than five minutes.

Getting up, I walked over to the mirror to examine my handiwork and was honestly surprised by how good it looked. Before hand I’d even shaved my pubic hair into a small stripe and it looked perfect. Now, as long as I could get the glue off, it seemed as though I had found the perfect tucking method. Why hadn’t everyone been doing this? Staring at the perfect gap between my legs, I started imagining what outfits to wear. Some leggings definitely. I’d have to try some bikini bottoms. Yoga pants would be a must. There were so many possibilities going through my head as I walked over to the closet. Just a few steps, but after the third or fourth, I definitely felt something. A tug, a shift. With each movement, my illusion was falling apart as the glue sloughed off. Within a few minutes all I had was a mess of half-taped boy junk and a nasty glue residue that also took a week to finally scrub away completely.  Sadly it just didn’t hold. Then of course the instructions on the tube say you’re supposed to sand the surface before you glue, so I guess it’s my own fault for not following instructions. 

Later, I would discover KT Pro Tape, a brand of athletic tape. And by “discover,” I mean someone else discovered it and made a YouTube video that I watched. In this video a young transgender girl extolled the virtues of the tape and explained how she needed only a single piece of tape to do a tuck that would last multiple days, allow the full range of excretory functions and even wear things like leggings and even do squats comfortably. Not being athletic myself, not only had I never heard of the stuff, nor did I know where to buy it. Also, I didn’t know what squats were. But, I was able to find some KT Pro Tape on eBay to try it out.

These days, I burn through rolls of it, despite how expensive it is. It’s around 75 cents a strip and there are twenty strips in a roll. Each piece is about one and a half by ten inches, and I use the same method as with duct tape, only KT Pro Tape has a few major advantages. Firstly , it’s flexible so it moves and breathes with you. It feels natural, like it’s a part of you. You can pee with it and it won’t come off. In fact, if you’re wearing it, you have to sit down to pee, which makes me feel rather feminine and confident. I’ve actually worn it out swimming and it’s managed to hold. Plus, it comes off easily with no pain or residue. It’s perfect, though a little pricey at $3-4 each time you dress up. It gives a smooth, comfortable and flawless tuck, that looks good even in bikini bottoms. Plus if your drunk ex-girlfriend lifts up your dress and starts feeling around between your legs, she’ll be suitably impressed, and in the end, isn’t that what matters

Good tucking!

And also, for those who may be interested, I also recorded a podcast about this very topic. Check it out!

Monday, September 7, 2015

How to Get Started Crossdressing

Over the years, so many people have asked me how to get started crossdressing. Well, the truth is that you need to start by getting clothes, though even that can be intimidating and confusing for some people. So, I thought I'd share some basic advice for those people out there looking to get started or looking to step up to the next level.


You can't crossdress without clothes right? That would be cross-nudity and that's something probably better discussed via Tor. The most important thing is get over any fear you may have about getting out and shopping. Will someone see you looking through the women's section? Yes. Will people see you buying women's clothing. Yes. But, you need to realize that most people are so into their own lives that they will not pay any attention to you. Store clerks ring up a hundred people a day and put almost no thought into what people are buying. They're doing a job and they don't care. Store clerks have seen men buying dresses before. Hell, they've seen kids piss on the floor, they've seen crazy people try to steal stuff. They will not judge you. You'll be fine. If you live in a small town and are worried about your uncle or the preacher seeing you, then drive over to the next town or to that bigger town nearby. Or hit the Wal-Mart at 3am. Trust me, a guy buying a bra is probably the most normal thing going on in a Wal-Mart at 3am.

My best advice is to go to Goodwill, Salvation Army or a similar thrift shop. Because you can get clothes on the cheap, you can get a greater variety of looks to try out. If you're uncomfortable taking dresses into the fitting room, thrift shops are cheap enough that an ill-fitting garment won't set you back too much. One rule about fitting rooms though- be sure to use the one of the gender you're presenting as. If you're a beginner, I assume you're shopping in guy-mode, so yes, take the dress into the guy's fitting rooms.

Look around. Pick out three or four dresses, maybe a skirt or two and some tops, depending on your budget. If you don't want to try things on, figure most average guys are probably in the size 10-14 range. Or go for L or XL as well. Sizes vary not only by brand, but sometimes within brand. Even for the exact same dress there can be two slightly different 10s. An important note about ladies' sizing; odd numbers are for juniors and even numbers are for regulars. Unless you're on the smaller size, best to stick with even numbers if you're unsure about your size.

Also check thrift store counters to pick up some inexpensive jewelry. Maybe a necklace, some bracelets and a ring or two.

Cool. Now you're got some outer wear.

Hit up Marshalls, Target, Wal-Mart or a similar store and get yourself a bra and some underwear. You'll probably want a pair of tights too (knowing the average crossdresser). For bras, the number is the circumference of your chest just below where your breast would be and the letter indicates the cup size. You can measure yourself before hand or figure that most guys will be in the 34-38 range. Don't go too crazy on the cup size. Maybe start with a B or C then go from there, unless you have a larger frame in which case a D can can work. Most women are in the B range, so yeah, while large boobs are fun, you don't want to look too ill proportioned. Don't worry about breast forms for now. Just go with some toilet paper and you'll be fine.

Underwear is sized fairly normally, usually in the S, M, L way. These can also correspond to numbers, like 7 being a medium. They usually print both on the label. Pick up what you like and what appeals to you. We can discuss tucking another time, so for now, yeah, pick up what you like.

Tights also have basic sizing an some even have charts with your height and weight on the back telling you exactly what size to get. Now if only they could do that for dresses.

Cool, now you've got all the clothes you'll need for a few outfits! If you want to get more advanced, check out my post on padding, but that's not something you need to do just to start. Just throw on a dress and enjoy it!


For a beginner, just go to Payless. They sell larger sizes and they're not expensive. Plus if you go during one of their sales you can get the second pair half priced. That's great since you'll totally want to pick up a couple pairs. I'd say get a pair of flats and a pair of 2" heels. Shorter heels are better to walk in anyway. You can work your way up to a 6" stiletto. Flats are great to have especially if you're tall. They will also help you blend in since most women rarely if ever wear heels. Try and go for a classic black as that will match with more things.

Payless also sells inexpensive purses. Pick one of those up too if you can.


Hit up Wal-Mart or your local CVS. Try a brand called Wet & Wild, which is inexpensive and not too bad quality wise. You'll want to pick up the following items:
  • Eyeliner pencil in black or brown. Stay away from liquid or gel eyeliners for now.
  • Eye-shadow palette.Try a couple different colors if you can afford it. 
  • Mascara. 
  • Blush.
  • Lip stick. Get a couple different as your pocketbook allows. 
  • Lip liner (get a darker shade). 
  • Foundation. My favorite is Maybelline Dream Matte Mouse. Then I put a powder over top. You'll want to pick up some sponges for application and those will be in the same area.
  • Nail polish. Be sure to also buy nail polish remover! 
Makeup takes a ton of practice. Years of practice. You will not be good at it at the start, but you'll never get good without starting. I also recommend reading Makeup Addiction for tips and tricks once you get past the basic stage.

Have fun playing around! Try different looks, maybe a light basic look or full on crazy whore and everything in between. The more you practice, the better you'll get! So practice!


Unless you have long hair and can pull off that look (maybe you're in a metal band?), you'll want to get a wig. Don't waste your money on cheap wigs. Avoid Halloween or costume shop wigs. You'll want to search for "Beauty Supply" shops in your area. I recommend shopping for a wig in person if you're not familiar with them. Yes, you're going to need to get over any fear your have about sales clerks or people seeing you buying a wig, but plenty of men buy wigs. The stores are going to be used to it. Don't worry! Remember that the heads are displaying the style, but that you can get different colors in that style. Just find a style you like and let the sales clerk know what color you might be looking for.

Most places will let you try on maybe three or four, provided you buy a wig cap for maybe $3 or so. I'd say if you're starting out, try them on and see what works for your face shape.

And I recommend getting bangs or a lace-front if you want it to look natural. You can get a basic lace-front for around $40. If the store offers to cut the lace, let them. They might charge an extra $5 for this service. You can also find YouTube videos about how to cut the lace-front.

For now you can go with just a regular synthetic hair, which is much cheaper than human hair. Try and get a color that matches your regular hair color, but you can also go nuts if you want. I'm not your boss. Have blue if you want! It's your look!


I recommend shaving. It feels so amazing, but I understand that not everyone can though. Shaving your body isn't too much different than shaving your face. But, if you've got some serious hair, I recommend shaving first with electric clippers to thin out the forest. Then rinsing that off. Apply shaving cream (I think Skintimate provides better coverage than regular guy's shaving cream).

My routine is to rinse, shave, then shower and exfoliate with a loufa, then applying basic moisturizing lotion. I'll do my toes, feet, legs, arms, chest and underarms. I shave against the grain.

If you get red bumps on your legs, don't bother with any products that claim to reduce them. They do not work. Red bumps mean you're shaving too close and you can look up YouTube videos on how to shave less close, but mostly it is just practice. I got them for years and now don't ever get bumps.

For my face, I'll shave once with the grain, then a second time against the grain. Then I moisturize.

Always moisturize.

If you can't shave your legs and still want to rock that dress, you are so lucky that thick leggings are in fashion right now! Pick up a pair and have fun!


If you can get away with it, go get your brows waxed! Head on over to the beauty salon or nail place and spend the $8 to get them waxed. Waxing takes maybe ten minutes and is relativity painless compared to plucking or threading (fuck threading!). Make sure the person at the salon knows what you're looking for. Bring a picture if you can. 

Be sure to tip. If she's turned your unruly brow caterpillars into beautiful feminine arched brows, tip that lady a good 100%. She's earned it. 

What to Do Dressed Up?  

Get dressed up! Take a day for yourself. Spend the morning shaving and prepping, then get dressed and do your makeup. Throw on that wig and be amazed at the new awesome amazing lady looking back at your from the mirror.

Take photos to share, maybe take those first steps outside. Try on different outfits to see what works for you. Dressing up is like any skill. It takes practice to get good at it. The more you do it, the better you'll look and feel!

And when you get to the advanced level, go out shopping, try stuff on, then hit the bar for drinks with your girlfriends! Or church if you like. Whatever works for you.

Just enjoy being the beautiful girl your are!