Learning to Be Feminine or Unlearning Masculinity 2

Once I gave in to my feminine side things changed.  The world didn't seem as menacing for some reason.  I didn't feel like a little male poodle trying to bark at big dogs.  I accepted myself for who I was, and it was okay.  The big dogs weren't out to get me anyway.  It was just my perception that they were out to get me, and this caused the anxiety and problems.

As I went further down the road of life, and began to explore crossdressing and sissy websites, I saw scores of men who not only liked projecting femininity, but who also adopted a feminine persona.  They talked and acted like girls.  Of course for someone like me, who has lived as a man for so many years, it's a pretty difficult thing to imagine myself doing, but is has made me question whether I act like a man because of societal expectations.  Was I really as girly as these other sissies, but just too scared to act like it?

I mean, my whole core of my self-image has been built around the idea that I'm a man.  As I said before in my other post, I've realized that some of this is complete bullshit, but there is a definite masculine side to me.

The thing I'm having a problem deciding is how much of it is real, and how much is just learned behavior and habit.

The first time I went out dressed, I remember that I didn't feel so much like a woman and let go in the moment.  Instead, I was surprised in a moment of self-reflection while I was walking around in my dress, that I had my same male voice inside my head, and I was thinking in a male way of how to walk and act.  So, in effect, I was a man in a dress that first time I went out dressed.  I didn’t truly embrace the moment.

As time has gone by, I've explored this idea of how much of me is feminine, and have even experimented with trying to use a female voice or think in a feminine way.

To an extent, it's has challenged my resistance to giving in to my femininity.   There definitely is a fear which I think holds me back.  I think I worry that part of my masculinity might slip away and never come back.  Sometimes, though, I love the distinctly feminine feeling I get lying on the couch in a maxi-dress, curling up with a pillow.  I like feeling soft and pretty, and it’s not scary at all.

In another way, though, sometimes I definitely feel masculine.  Usually when I'm out in social situations, I slip into my male persona.  It’s just easier and more comfortable.  And sometimes at home, I just feel masculine.  I don’t want to be prissy, and instead just want to watch football and lie on the couch and eat leftover pizza (although I'm usually dressed from head to painted toes as a girl.)

In the times that I consciously try to make myself act like a really girly, sissy girl, it sometimes only lasts for a few minutes.  It just doesn't seem real, and seems more like an act.  Still, it makes me question of how much is real, and how much my mind is just stubbornly clinging to its male ways.

I guess it's a slow process.  I think that some male traits will be with me forever, but others might slip away eventually.  Perhaps a few years from now I'll be a balanced effeminate man, or perhaps I'll be so girly that I'll be openly dressing as a woman and adopting a completely feminine persona and name.

Only the future will tell, but I’m looking forward to the discovery and the journey.

Learning to Be Feminine or Unlearning Masculinity

How much of me is real?

A few years ago, that question would be easily answered, "Of course all of me is real," I'd boldly say, thinking that I was really in touch with myself.  And in some ways I was honest with myself.  But as I've further explored my feminine / sissy side, I think I've realized that for a long time, I was constantly in a state of self-deception about my masculinity.

I'm a pretty honest person, but I'll admit there are times when I haven't really been myself before.  As I've gone further down the path of femininity, I've realized that I've spent a lot of energy trying to keep up this masculine myth for myself.

I've always been skinny, sensitive, pretty, and different, and as soon as any guy would point that out, I'd bristle and emphatically state the opposite.  In fact, I've spent my entire life trying to prove the opposite, when it was painfully obvious to all around me that I wasn't the most macho of men.

I even went so far as to do overtly masculine stuff at times, way beyond my physical limits, to prove that I was just a regular guy.  And you know what?  I still wasn't proving anything to anyone.  All I was doing was deceiving myself.

I think I've always had a sort of social anxiety in the past because I had a latent fear that I wasn't measuring up to people's expectations, and they all knew that I was a phony.  I can recall several instances of starting conversations - manly conversations - all the time, just to prove it.

"Did you watch the game?"  That type of stuff.

Still, I was full of shit, and when you come from an unreal place, the image you project is unreal, and this was eating me up for several years.  I spent so many years pretending to be someone other than who I am.

These past few years, I've slowly learned to embrace my quiet, caring, silly, gentle - feminine side.  I don't always try to be Mr. Macho in front of others, because I'm not.  And you know what?  I think I have better relations and conversations with others now than ever before.  It's because I'm more real, and less nervous.

It took me a lifetime to learn this lesson, but I would encourage others to be more of themselves.  It's the only way you'll truly be happy.

Stepping Out: Some Thoughts for the Future

It had been a few months since my last Stepping Out adventure.  My wife came home from her trip, and I grew my facial and leg hair back.  Summer started, and although I had some urges to shave my legs again and go out, I knew that I couldn't because I would be attending pool parties and the like, and I would be wearing shorts on a regular basis.  (My wife would not have been happy if we had to skip social events because I chose to impulsively shave my legs one night.)

And I agree in a way.  As much as I've embraced my feminine side, the last thing I would want would be to have someone recognize the fact that my legs were shaved in a social situation.

I could just imagine, being at a party, laughing and telling a story, and someone would casually look down and say, "Are your legs...shaved?"

That would be an uncomfortable moment.


Even though I knew that masculinity and hairy legs was part of my reality for summer, I still often felt the urge to put on some women’s sunglasses, a flirty short summer skirt, and a pair of sensible heels, and go out in public so badly.  Something inside of me just wanted to go out again, and experience that feeling, and those nice summer days were calling my name.

I had a few days off, and knew that what I really wanted to do with them was to dress up and get out of the house.  The problem of my hairy legs required me to have to wear tights with my high heeled sandals.  Recently it has been in the hundreds of degrees here during summer, and the tights looked a little strange considering the weather, but they don't look completely out of place either.  They looked more like stockings and not thick winter tights.

Another difficulty was that I really didn't want to bother with too much makeup this time.  My wife can always detect the slightest bit of mascara or eyeliner or sparkle from eye shadow, and I didn't want to hear it if she happened to scrutinize my face that night.  Besides, I really don't like putting on makeup sometimes.  (I know, I know - I should like it if I were a true sissy.)  Sometimes, though, it seems like such a hassle to put it all on, just to go out on a little adventure.

Maybe I am truly a girl, now I'm complaining about how I don't like putting on makeup ; )


Considering all of these factors: heat, makeup, tights; it would have been easy just to stay inside, but something inside me forced me to get the initiative to go out.  To make it an easy adventure, I just decided to drive around in my car.  That was easy enough.  Still, I had an idea that maybe I could go to the park if it weren't too hot.  I hate sweating up my pretty clothes.

I dressed; put on some foundation, lipstick and blush; and put my sunglasses on to hide my face.  As I drove around those two days, I began to think about how crossdressing is so much an act of isolation for many of us.  It's a secret and we don't want to get caught, but some part of us desperately wants to express it to the world too.  It's an interesting dichotomy.

That was how I felt.  I was out, but I was still alone.


Another thing that I found interesting was that although I haven't been out dressed that many times, now it almost seems a bit commonplace to be out on the street in a pair of heels and a skirt.  Whereas it seemed so naughty at one point to step out into the world in panties and a dress, now it just felt like clothing, and not such a big deal.  I mean it was clothing that I liked, and I felt pretty, but I didn't have a fluttering in my heart like it was such a crazy, dangerous, titillating thing to be outside in the world in a skirt and panties.

I guess that's a cautionary warning for some of you.  Once you step outside of that door, it's no longer a fantasy.  There are no more hot moments wondering what it would be like to be out in the world dressed as a girl, because you already know what it's like.

And that's how I felt that day - I know what it's like now so it's not a mystery.  Those heart-pounding moments of stepping out the door are gone.  The trepidation is still there a tiny bit, but the fear is gone. 

To tell the truth, I don't even feel like it's such a crazy thing anymore.  The first time I did it, some part of me inside said, "Are you sure you want to do this?  I know you have a fantasy, but this is dangerous.  This is so risky.  Are you really going to do this?"  I had such a guarded feeling inside the first time I trepidatiously walked around the open world in my heels with my purse on my arm, knowing that this was wrong in the eyes of society.

But now when I leave the house, my purse is on my arm, I feel confident in what I'm wearing, and I lock my door just like any other day when I'm leaving my house and walking to my car.  Basically it's me in a dress or skirt, and it doesn't seem so strange.  I guess since I've been in a crowded store wearing a dress before, just walking to my car in a skirt to do a little driving does not feel dangerous at all anymore.

Don't get me wrong, I'm not saying I've lost anything.  I still love the feel of being out in the world the way I'd like to be, but it's strange how quickly I've become used to it, like it's just an everyday thing.  There's an element of normalcy in this new feeling, like maybe it really isn't such a big deal if I'm wearing a dress.  It's as if I was expecting a quick, hot sexual thrill, but instead found something completely different.


This last time I went out, I noticed that I went through different stages during my journey.  At first it seemed a bit naughty being outside in women's clothing, then it left, and there were moments when I got caught up in whatever activity I was doing (like driving and walking) and almost forget about the fact that I was wearing women's clothing in public.  This time I was just driving, and I had to remind myself, and say, "Hey, you're in a skirt and bra with a white shirt for all the world to see.  Look, there are people all around you looking at you.  They see you as a girl," and it felt good realizing that I was being seen in my white tee shirt and bra again, even if I was just driving a car.

But as I drove around that time, with nowhere to go, I kind of mused about my need to go out.  What was the need, the urge to be outside as a woman?  Why did I feel a need to be among members of society in my secret clothing?  I kind of knew the answer and continued to drive. 

Since I had nowhere to go, just driving around aimlessly began to bore me just a bit.  I looked at all the stores and places with people going by, and dreamed of going beyond just walking into a store, and instead wanted to interact with people.  In the moment, I realized that didn't care if they knew that I was a man or not, I wanted to be recognized for who I truly was.  That’s all that mattered.  The whole future of everything played out before me.  I didn't want an isolated experience.  I wanted to be myself, it's just that is seems to be a seemingly difficult and impossible journey to take.

But that brought up a dilemma.  Being seen as a woman seems almost impossible, but being at home is an isolated experience.  Even stepping outside my door and getting in my car is still kind of isolated because I'm sneaking around trying not to get caught.  Even the bold step of going to a crowded store was an isolated experience in a way, since I hid behind my wig, and sometimes looked away from people's gazes, and walked the other way when somebody approached me.  Even when I spoke to people at the store, I was hiding behind my personae, pretending to be someone that I wasn’t.

No, I don't want to be isolated.  I think I need some sort of affirmation from society.  I want them to know.  I want them to know that I feel more comfortable dressing and acting like a girl, than I do pretending to be just another regular guy.

For now, that all remains a fantasy, and it makes me think: If I cross that fantasy line, will I have that feeling that it's not so much a big deal either?  Because like I said, walking out of the house the other day, I was in a skirt women's tee shirt, and a wig, and locking my front door, it felt as normal as if I were doing it in male clothing.  It was kind of a strange feeling.

Stepping Out: After the First Time (Part 5: Some Sissy Mistakes)

After shoe shopping, I was on a high, and I was convinced that there was no stopping me now.  In my mind, I assumed that I would be free to go out dressed as a woman anytime I wanted, without being noticed. 

"I have this passing thing mastered," I said in my mind.

My week of being able to dress almost exclusively as a girl, and having my nails painted was coming to a close, and I wanted to go further before it ended.  My only decision was what to do next.  Unfortunately, I wasn't so lucky the next two times that I went out.


One night I saw a pair of pink wedges that I liked, and instead of shopping online, I decided to go buy them at the store.  My prior shoe shopping experience was so successful, I wanted to relive it.  It was late, and on impulse, I quickly put on some makeup and a dress that I liked and headed for the store.

I walked with confidence, telling myself, "Just act like a girl.  Attitude is everything."  But I would find out that's not entirely true.

Going to the shoe aisle, I found the pair of shoes that I liked, but the two girls in the aisle right next to me seemed to look at me.  Not wanting to be too close to them, I went to another aisle and tried on the shoes and decided to get them.  A female employee walking by gave me a bigger smile than one would normally get.

I wanted the shoes, so I decided to take the plunge and wait nervously in line with a lot of people in this big chain store.  Walking up to the registers, I didn't really making any eye contact with anyone and just casually waited.  Finally, it was my turn, and the cashier seemed to smile when looking at me, not in a malicious way, but seemed curious.  I knew she knew I was a man by the look that she gave me.  I wasn't embarrassed and I didn't really care, but it did seem to bring the thought to my mind, "You're in the middle of a store dressed as a woman!  What are you doing?"

I paid and walked out of the store with my pretty shoes.

Now that I think about it, I guess I wasn't totally passable that night, but luckily there weren't a lot of people around since it was almost closing time.


A few nights later, I returned to the same store.  This time, again, I was in a sleeveless dress, and now that I think about it, I think my shoulders were one thing that gave me away.  Another thing was that the dress I wore was too low cut for my chest.  Seeing a male chest without the continuation of the breast signals that something isn't right.  All you need to do is give away one little cue that you're not a woman, and people start scrutinizing the entire package, and then they see through the disguise.  I found that out the hard way that night.

I knew immediately this time that people knew.  It wasn't like the other successful nights when I moved freely amongst the people in the store.  No this was an entirely different feeling.  At first, I didn't know, and just did the same things I did on the previous nights, looking at dresses pretending to be just a regular girl.  I caught some weird looks, nothing much that registered at first, but when I went to the intimates aisle, a lady who was shopping looked at me kind of strangely and left.  I almost knew then but didn't want to jump to any paranoid conclusions.  Still, I decided to take my leave from the store.  I didn't really feel scared or embarrassed, but I didn't want people to know either.  If they did, then I thought, "So what?  I'm a stranger in a dress.  They don't know me, and if I give them a bit of a giggle, then so what?"

Walking toward the entrance, I saw a few more looks, and one girl said to her boyfriend, "Oh yeah...mustache..." I caught in passing.  I’m pretty sure that she was talking about me, and realized that my makeup probably wasn't good either that night, and the irritation of shaving against the skin for five days had probably caught up with me too.

It was not a successful night as far as passing, but it did teach me a lesson that I wasn't so scared to be a man in a dress in front of strangers.

I'm not lying.  I really didn't care.  If the whole store came to a screeching halt, and people asked me if I was a crossdresser, I would have told them with confidence that in fact, I was.

Strangers don't seem to scare me, it's people that I know.

That pretty much ended my week of dressing and going out.  There were a few more places that I went, which I didn't describe, and I had such grand plans for a few more nights, but when the last days came around, I just decided to give myself a rest, assured that I had done quite a lot for a first week of going out dressed.  It was a fun time, and I'm glad that I decided to live life instead of playing it safe.

Stepping Out: After the First Time (Part 4: Sissy in a Shoe Store)

I had successfully gone to the mall, and now headed for one of those brightly lit shoe warehouses that had thousands of pairs of shoes up and down the aisles.

Getting out of the car, as I walked in, a big wind began to blow.  Not only did I realize what if felt like to have my skirt lifted by the wind, but the long hair of my wig was all over the place.  It wasn't exactly how I wanted to approach the store.  Luckily I was far enough away that no one noticed.

Fixing my wig, and straightening my skirt, I clutched my purse, and walked inside the very brightly lit store.  Once again, lots of women were there, coming and going, and none even really looked at me twice.  It was a strange feeling to be accepted as a girl without question, and I began to feel comfortable in my surroundings.  As I began to settle in, I was in ecstasy, knowing that I was able to freely walk up and down the aisles and take my time looking at any shoes that I desired.  At one point I even had to squeeze by some teen girls and their mothers to get past them in one of the aisles.

"Excuse me," I said softly in an unpracticed female voice.  I was so close to the teen girl, and she just politely moved a few inches, no weird looks, no double-takes.

I tried on several pairs of shoes that night in the store, and settled on a pair of black patent leather, cork bottomed sandals, with five inch heels, and a tiny ankle strap.  It was a bit of a challenge securing those tough-to-secure leather ankle straps and still be ladylike, but when I put them on, and stood up, I knew that I really wanted them.  The only thing was that I would have to pretend to be a girl in front of a cashier.  This was a new challenge that I wasn't expecting, but I really wanted those shoes that night.

Gathering up some courage, I went to the counter and waited in line, hoping the people in front of my didn't look back or want to make conversation.  I was glad that a girl was at the cash register, but she was busy, so a male cashier whizzed by and opened up another register and pointed to me.

He didn't seem to notice right away, when he said, "Did you find everything okay?" and I answered in my best feminine voice.  But when he asked a follow up question, I saw him look up, and then he knew.  It was an uncomfortable moment for both of us, but we both just pretended it didn't exist.

Still, it wasn't that bad.  I didn't really know that guy, and he could have probably cared less.

Walking out of the store, I felt elated at my adventure, and excited to try on my new shoes.  This was so much better than shopping online!

Stepping Out: After the First Time (Part 3: Going to the Mall)

In my last Stepping Out adventure that I wrote about, I plucked up the courage to go into a store on a busy Saturday afternoon.  I think the dress I wore in daylight fit my male form well.  It had short sleeves which hid my skinny, but still somewhat masculine shoulders, and the front of the dress was high enough to cover my chest.  As always, my long wig helped to hide some of my face.  Of course, I didn't know that my choice of outfit would make such a difference in my ability to pass as a woman.  I learned that lesson in a latter adventure, but more about that later.

Encouraged by by daylight experience, my next adventure was to go to the mall.  This was a big step, but after my trip to the store, I had some confidence that it wouldn't be bad.  This time, I wore a girls' white tee, a short but sweet juniors' skirt, and some three inch heels.  Of course my legs were shaved and both sets of nails were done.

Arriving at the mall, I knew that I just wanted to go to Macy's, and perhaps if I had the courage I would actually step out into the mall.  I entered Macy's through the parking garage because it was less crowded.  Right away, I ran into two sets of teens.  One was a set of girls walking out.  Pretending that nothing was amiss, I walked right by them.  They didn't even look at me.  The next was a rowdy group of about six teens walking in with me.  I had always heard that teens were the bane of crossdressers, and I cringed a little as we merged by the stairs, but they didn't seem to notice me either.  Still, just to be safe, I walked a little slower and let them get ahead.

Once inside Macy's, and the small fear had passed, I had that same thrill as when I was in the previous store the day before.  Here I was, in the middle of the mall in nothing but women's clothing - me - in the mall, in a skirt, panties and a bra.  Once again, I walked by several women, and none seemed to even notice me.  I know I would have gotten a weird look if they knew, but I got nothing back from them except two strangers passing.

That made me feel good, and my anxiety began to drop.  I rid myself of the tension, and told myself, "Enjoy this.  Don't treat it like you're getting a tooth pulled."  It was in that moment, that I seemed to take a metaphorical breath.  Everything seemed calm, the night was calm, and I could hear the music was playing overhead.  Walking through all the areas I began discovering all the different clothes that were available to me.  My painted nails felt so pretty, and I felt feminine picking up the clothing on the hangers with my pretty nails.  I suddenly realized that if everyone thought I was a girl, there was no shame in acting like one.  My gestures became more naturally feminine, my walk, my hands, my face.  I was on a cloud feeling pretty and feminine, doing what I actually wanted to do in life.  It was great.

I walked by the entrance to the mall, and it seemed tantalizing, but going out there would be like jumping from a pond into the ocean.  I would have to save that for another time.

Still, I was on such a high that I didn't want the night to end, so I hopped in the car and went to a nearby shoe warehouse...

Summer Panties: Cotton vs. Nylon

If you're like me, you probably like your silky panties.  I have been underdressing for several years now, and have been wearing my favorite nylon panties for years.  Most of the time they're great, but the one time I do notice them is on hot days.

You know the days: when you're out in the heat or working on something a little strenuous.  It's at those times that I've learned that my nylon panties aren't the best.  They hold in heat, and when I get home and want to feel sexy, I have the unsexy feeling of nylon clinging to my butt.

Most of the time, it's as simple as putting on a new pair of panties (I have many, many, many pairs of panties, so that's no problem : ) but sometimes when going out into the heat, I just go with a pair of cotton panties.

Cotton hasn't always been my favorite, but I've learned to appreciate it.  Women's cotton is different than men's.  It's like a soft hug, or a comfortable pillow, and is actually a nice feeling.  The only drawback is that there just isn't that silky feel.  But cotton isn't for sexiness, it's for comfort, and just feeling comfortable like a woman would is a subtle sexiness in itself.  I've learned to appreciate cotton panties; however, nylon is still my preferred panty for most occasions.  Sometimes, though, for a hot summer outing, I now find myself, at times, grabbing a fresh pair of cotton panties when I'm going out in the sun.

Still, I guess I can just avoid all that nasty sweating, and just stay cool and clean like a pretty girl, and stay in my nylon panties.  Who need to do all that sweating anyway?  But it can't hurt to have a few pairs of cotton panties on standby just in case.  Now, I'm just going to have to find something a little girly, maybe with some little flowers on them and a bow at the top...yes cotton panties, like the kind I should have worn as a little girl.