Advice on baby steps

[Matterhorn]

Hi All,
As you can see I'm new to the site and wanted to ask a bit of advice. To be honest, I'm still figuring out if and how much I want CD to be a part of my life. I'm complex (like us all) and have a strong (and what I would call) masculine side to my personality. I love the outdoors - rock climbing, backpacking, skiing, hiking, mountaineering - the more challenging the better. Some people would find this gross but I am perfectly happy to go days (or even weeks) without showering when I'm in the mountains (although love to swim/bathe in mountain lakes). There is something natural about it that helps you connect with the land around you rather than fight the effects. [Side note: I did indeed go three weeks last summer without showering on a backpack trip and do you know what? I had absolutely no BO (even I was surprised). It proves that BO is largely related to the foods we eat (I was eating mostly healthy freeze-dried meals, nuts, dried fruits/vegetables, etc.). I am passionate about health, and the foods we eat play such a critical role in all dimensions of our health]

Anyhoo, as I was saying I consider myself to have many masculine characteristics. However, I do have a feminine side. Since college I have enjoyed the thrill of putting on pantyhose (in secret) and over the years have built up several large collections only to purge them for one reason or another. I have broadened out to many other items (90% online purchased) including panties, girly socks, lingerie, leggings, a few skirts, tanks/camis, makeup, and a few pairs of shoes. As far as I know, no one has ever found out about any of it. It truly would be devastating if any of my close friends or family found out, at least until I'm married. I don't want a CD revelation impacting my self confidence and hence my ability (as I see it) to pursue my lofty career and life goals. But I do enjoy expressing my feminine side. I can continue to do this in secret, but have increasingly been looking for very small ways to do this in public.

For example (and I know this must be laughable for most of you given the timidity), I like wearing women's ankle and no-show socks with my sneakers (these are so similar to men's nowadays as to be virtually indistinguishable, but I still like it). I like wearing running tights, especially ones that look similar to women's tights. I've worn women's trouser socks at work. Occasionally I will wear panties under my work clothes, if they are not uncomfortable to wear all day.
So, with that as my long-winded introduction, I wanted to inquire will all you "experts" about other small baby-steps you would suggest that I consider (mostly for public). I hope you don't look down on my novice position here because I really do like and want to express my feminine side, just in very small ways (at least for now).

Also, my suspicion is that there are many other men out there just like me, looking for small ways to express their femininity in public without going all the way. For every one CD man, I would guess there are 5 or 6 men drawn to it but only looking for small ways to express it. Thanks so much all for any advice you would be willing to offer!

-Kristy(?)

[Jenniferathome]

Kristy, you might be surprised at the number of very masculine men on this forum. I race mountain bikes, surf and wakeboard and even skydive. Being masculine and being a cross dresser go quite well together.

As for public baby steps, that's not me. I'm an "all in" cross dresser.

take care

[Samantha2015]

Kristy I'm still very much in the closet with my dressing too. Little steps.. you could paint your toenails,
easy enough to hide with shoes. I like when I'm in "happy feet" mode.
I'm sure you will get other ideas here.

[Donnagirl]

Kirsty,

We have soldiers, sailors, airmen, marines, special forces operators, divers, cops, MMA fighters, boxers, mountain bikers, patched bikies.... You name it, there are uber macho guys here with a strong feminine side... No one is unique, no matter how much you might think...

I personally spent quite a while with painted toe nails, shave legs and panties under my uniform...you take the risk to reap the rewards...

:-)

[Wen4cd]

Petzl sells some lovely pink climbing gear.

I don't climb rocks. I like hillwalking a lot though, the more climb the better. Did Mt Mitchell last spring, and doing Fuji this summer!

[ashley-2501]

I am in a similar situation. love the outdoors and work with the military.
I use long drives to go out dressed and still not really be seen. But always plan on changing if something happens. its been quite useful. But try using women's deodorant, black leggings or if you can under dressing. its all about the little steps. Good Luck

[kittie60]

As far as baby steps go do what your comfortable with. Try under dressing more and work your way up from there. Its your life so enjoy it to the fullest

[Sara Jessica]

The endeavors you enjoy are human. They are only described as masculine because perhaps more men than women participate in what you enjoy.

And I agree that there are many guys who are likely in the same boat that you are. You are just willing to admit it. Some will underdress or subtly outer-dress to maintain a connection to their feminine side or simply to feel as if they are getting away with something. Regardless, you seem grounded and are embracing your nature. Don't fight either gender, just go with the flow and own it.

[michelleddg]

The endeavors you enjoy are human. They are only described as masculine because perhaps more men than women participate in what you enjoy

Right again. My wife and I are both passionate mountaineers. We see plenty of women in the wilderness. Hugs, Michelle

[Allisa]

Spent a lot of time in the wilderness at a younger age and work at a masculine trade. I started with the simple act of shaving my underarms and progressed from there in time. As far as in public just started wearing panties and once I figured out no one could tell every thing evolved to who and where I am today. That is to say, you will go the same direction, as only time can tell and you'll know your limits.

[Julia1984]

Hi Matterhorn.

I'm in a similar position to you but, I suspect, a fair bit older. I'm also still working on how much, where and when. I underdress quite often, but today I wanted to take a (very) small baby step in public. So I borrowed a heavily patterned green silk scarf from my SO. I love the feel of silk (who here doesn't?) and this felt like an achievement to me. Apart from that I was completely in guy more, but it felt like progress!
I'm sure others will have plenty of tips and strategies. I've also done "happy feet" in the past. You could try clear lip balm, perhaps?
Julia

[nikkiwindsor]

Periodically, I like to grow my nails longer (not too long). I then spend time carefully hiding my hands during meetings with coworkers, etc. It feels very feminine to have longer nails since you have to adjust your routine (typing is different, you must take great care not to break a nail, filing/shaping them into a feminine shape and prevent splitting, etc). And when the weekend arrives that at a very nice length for polishing. I'm still learning to polish my nails...see below! What do you think? Nikki

[~Joanne~]

To be honest, I'm still figuring out if and how much I want CD to be a part of my life.

I found this a bit perplexing to be honest. I think we have control over whether we dress or not at any given time or day but i don't think we have much choice when it comes to the "if" part. Even if you decide, ok I am not going to do any dressing or under dressing anymore, the desire to do so will always be there. This is why so many of us have purged time and time again, we thought we could control this and we simply can't. You either embrace it for what it is or you live miserable your whole life.

I like wearing women's ankle and no-show socks with my sneakers (these are so similar to men's nowadays as to be virtually indistinguishable, but I still like it).

The only difference between women's and men's is that the fabric is a lot lighter in women's socks. Other than that, they are pretty much the same. The brand name might be pink in women's compared to the red in men's but other than that I suspect they come off the same machine. I wear them all the time and no one ever notices.

The same can be said about women's bikini cut panties, they are the same as the men's other than the fabric used or the color choices.

I wanted to inquire will all you "experts" about other small baby-steps you would suggest that I consider (mostly for public).

I wouldn't call anyone an expert. seasoned maybe but we all do what it is that we want to do, what we are comfortable with. I suggest you do the same. There is no right way or wrong way to CD. We all do it differently, we all decide how far we want to go with it, what our styles are, and how much we may or may not want to show the world. Some of us need the wig, some of us don't, some of us need a full shave and some of us don't....the point is that we do what we feel comfortable with and you should do the same. if your masculine side is as strong as you believe it is, you'll do so without really caring what anyone else thinks.

[Robin414]

I'm pretty much 'tween' all the time myself and I wear ladies skinny jeans and clear nail polish, occasionally mascara, powder, and neutral lipstick but then I seriously look like a chic wannabe but it really works! 😀

[Dana44]

I have long mid blonde hair. I have very long fingernails. Earrings, currently the sparkle type. In male mode that does not pose a problem with men. Shaking hands etc. yet my girlfriends friend noticed my long nails. She said that is very feminine. Wow, at least I know he doesn't crossdress. LOL

[sometimes_miss]

I'm still figuring out if and how much I want CD to be a part of my life.

If you get to choose, I would say, choose none of it. It just makes life more complicated, not to say potentially dangerous in some ways.

I'm complex and have a strong masculine side to my personality.

We don't have 'sides'. It's part of your personality. Using the term 'side' is a way of trying to separate identifying with particular behaviors. We get it. You like traditionally masculine sporting activities. Yet, there are lots of women who do as well.

However, I do have a feminine side.

As above, it's not a 'side'. It's part of YOU, and there's nothing inherently wrong with that. But we're still battling a large generally held belief that being feminine in any way is the worst possible thing that a man can be. Despite women outwardly saying they want more sensitive men, most of them choose to date macho assholes and other types who are prone to mistreating them. At least, now we know why.

It truly would be devastating if any of my close friends or family found out, at least until I'm married. I don't want a CD revelation impacting my self confidence and hence my ability (as I see it) to pursue my lofty career and life goals

It can be just as devastating no matter when the world finds out. Especially if your wife doesn't know before you get married. And work? Being openly known as a crossdresser usually doesn't have any positive effects on your profession unless you're a female impersonator. Negative effects, well, they're gradually decreasing, as no one will openly fire you for being a crossdresser, they might, however, find another reason, especially if the people in charge aren't comfortable with the concept of crossdressing.
As I'm not 'out' and don't wear any female clothing at all, ever, in public (my job is one where all men are considered gay by default, and I don't want to reinforce the stereotype). But you can start by going the 'metrosexual' style, and just start wearing more androgenous clothing. There is plenty of men's underwear that looks like and feels like female underwear; but it won't give you the psychological comfort that wearing woman's clothing does, and there appears that is a strong incentive for a lot of us to ignore those men's 'panties' and insist that we get the real thing.

Also, my suspicion is that there are many other men out there just like me, <snip> For every one CD man, I would guess there are 5 or 6 men drawn to it but only looking for small ways to express it.

You're subject to the same things all the rest of us are; projecting your own feelings onto others, in order to feel as if there are lots more people who feel and behave just like you do.....even when there's no evidence to that effect at all. We want to believe it. Just like we want to believe that crossdressing is just another 'little thing' that women will gladly put up with if the rest of us is good, masculine and 'normal'. It's not a little thing at all. It's the biggest deal breaker when it comes to a woman finding us attractive or not. Women will date idiots, fools, poor men, bad men, murderers, wife beaters, even men who've beaten their previous wives to death. But as far as we know, there is a complete dearth of women actively seeing crossdressers. So if you get to choose, don't do it. Do pretty much anything else.

[sara.rafaela]

Hi Kristy,

I share some most of your athletic passions. I am a mountaineer too, and have done climbs in the eastern Sierra and Alps.

I also enjoy going out. For me dressing is more of live reality performance art. I enjoy the female form and this is more of art for me; and not really expressing femininity. My baby steps: a) Accumulate enough clothes and shoes to put together a couple of outfits b) Learn how to apply makeup. There are videos on YouTube about contouring and beard cover. When I got the beard cover right my confidence soared. c) select a wig d) Hip pads and corset e) During travel for work I dressed in the room, then got some confidence for a walk in the parking lot late at night, then to the car and a drive, then in a park or big parking lot. Over a period of a couple of months I got the confidence to go out.

Some of the tricks I did. I tended to stay in Hampton Inn type hotels. These usually have a back door away from the lobby. You can park there. You can ask for a room next to that door. Do not drink. If you go out to clubs, the police hover outside like sharks and if you are out enough, one day you will get pulled over, even for no reason. These days a walk through the lobby doesn't bother me and I prefer to stay in the city and take Uber. This makes it possible to drink. I would check out the bar or other location in guy clothes before making my grand entrance on another occasion. I used to carry a boy bag, with pants, shirt, shoes, makeup remover, and nail polish remover.

I would say I am passable at a distance. Most people do not seem to notice me, but if you were to check me out, you would definitely know what I am.

The first place I went was a transgender bar. Each new experience was scary. I locked my keys in the car and dealt with the tow driver. I got slightly rear ended once. Pulled over by the police. Lost my hotel key and had to deal with the desk staff. Each experience ended well and made me strong and confident. Now it is kind of routine. These days I much prefer to go out dressed than not. I will go out to most places, shopping at Macy's, a gay bar, a sophisticated straight bar. No, I will not go to somewhere like a trucker bar or a Hooters. Dressed, I feel like I am part of the "show". When out, most of the attention I get is mostly positive, women will chat me up at clubs. I get into many very "normal" conversations at clubs and bars.

[BLUE ORCHID]

Hi Kristi, You just have to wonder how many construction workers are under dressed. ~~......

[heatherdress]

Hi Matterhorn - Welcome. You are one of many on this site who consider themselves a "masculine man". By the way, you don't have to validate that you are male in any thread or prove your masculinity.

Your crossdressing path is yours alone. You can spend a lot of time trying to figure out why you like to wear women's clothing, or maybe just accept that you do - learn, grow, experience and enjoy. Maybe think of it as a gift that makes you special, not different and not weird. And decide how far you want to take this journey. Maybe you will continue to enjoy female socks, tights and panties. Maybe you might like to go further, much further. It is not possible to describe the thrill and excitement to see yourself fully dressed for the first time.

You can get help and friendship here. You might find a local crossdressing group or participate in a crossdressing event somewhere. But the path is yours to choose. Good luck.

Also, I agree with you that there are probably many more men who would explore their attraction to female clothing or who might have an interest in exploring their own possible femininity if they were able to. Too bad they may be hiding behind their own masculinity.

[Katey888]

"Experts..." heh, heh, heh...



Welcome Kristy... I'd grant that what we do have is an awful lot of diverse experience between us all - what you've expressed here is very similar to others (and myself, somewhat) but what I've learnt here over the past couple years is that we each have to find our own way through this condition we share, and while the experience of others can certainly provide some useful pointers, hints, and tips with makeup and accessorizing, your situation is unique, your relationships are unique, your circumstances, family, environment, working situation, etc. and your desires and feelings.

There's some great advice already on stuff you could do - if you like to mix or just accentuate a hint of femme in your dress, we have lots of folk that do that. We have folk that just underdress, folk that fully femulate at home and in public; folk that dress femme from the neck down; folk that just do specific styles... There are no right or wrongs in this, other than what feels right for us as individuals. Personally, I have found the greatest contentment in just working out what this means for me and being able to keep it in balance with 'normal' life while achieving a greater feeling of self-acceptance... I hope you can work it out too - it should be interesting seeing how it develops for you...

Good luck!

Katey x

[LaurenS]

Periodically, I like to grow my nails longer (not too long). I then spend time carefully hiding my hands during meetings with coworkers, etc. It feels very feminine to have longer nails since you have to adjust your routine (typing is different, you must take great care not to break a nail, filing/shaping them into a feminine shape and prevent splitting, etc). And when the weekend arrives that at a very nice length for polishing. I'm still learning to polish my nails...see below! What do you think? Nikki

I do exactly the same thing!

[flatlander_48]

K:

As you can tell, there are lots of ways to go about this. It is similar to water seeking its own level. When you eventually settle into where you feel comfortable for the long haul, it will likely look different from most other people. This is not a one size fits all situation. Further, there is no road map for all of this. You may find that you get to the same place as someone else, but by very different methods and thought processes. Alternately, you may reach a very different conclusion from someone else even though you started with the same information. Just remember, there are many, many variables here...

DeeAnn

[CONSUELO]

Welcome to this wonderfully supportive site.

The love of going mountaineering or on long backpacking trips is NOT just a male thing. Lots of women do it. Last year I did a long hike in the southern Sierra Nevada and learned that two women were trying to set the record for traversing the Pacific Crest Trail and they were averaging 40 miles per day. Now that is toughness for you and has nothing to do with being a man or a woman.

As to the degree of cross dressing that you want to achieve, that will largely just happen as you embark on a voyage of exploration. Your desires around cross dressing will change as you go through life so don't be dogmatic about it. Be prepared to adjust to changes, be ready for surprises. Good Luck