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.

The Sissy in the Wig Store

My thoughts on my other story about needing a wig remind me of a funny story.

I had been debating for a while about going to a store to get a wig.  The first couple of times that I went out, I used my wife's Halloween wig, which was a decent wig that she spent a lot of time styling, so it wasn't bad.  It wasn't the best though either, and the hair color was different than mine.  I knew that a good wig was the last piece of the puzzle that I would need in order to be able to step out of the house as a reasonably passable woman (and it ended up coming in very handy during my first big adventure out to the clothing store.)  But just like everything else related to these types of decisions, the decision to go into a store and buy a wig is a lot easier than plucking up the courage to go to a store and actually do it.

I know I probably could have gotten one online, but I wanted to be able to pick one out myself and prove to myself that I had the courage to do it.

Months literally went by while I tried to make the decision to do it.  I was pretty happy with dressing at home, so it wasn't that big of a big deal.  The more I delayed, however, the closer Halloween approached, and I knew this would be the time to act.

The week of Halloween, I knew this was my one, good opportunity.  The timing was perfect.  No one would suspect much from a guy buying a wig for a Halloween costume.  I went to a wig store near my house, and took a deep breath and walked in.

"I don't know any of these people," I told myself, reassuring myself that their opinion of me did not matter.

Walking in, I began to peruse the aisles of wigs.  The store was Korean owned, but most of the workers and customers were black.  Some ladies were back at some chairs in an area like a hair salon getting their wigs adjusted, and they kind of looked at me strangely.

I somewhat skittishly looked for a wig that I liked, when all of a sudden a saleslady, an older woman, came up from behind and asked me if I needed help.

"Um, yeah...I need a wig, preferably something long that matches my hair color."

She gave me a look that said, "Okay, whatever, sissy boy," and pulled out a long wig.

"Will this do?" she looked at me, “Is this long enough?”

I scrutinized it a bit, and accepted it.  I didn't want to seem like I was being too picky about a wig, but it was actually a nice one, so I just let fate decide for me.

"Would you like to try it on?" she asked.

"Sure," I said unwittingly, not knowing what that entailed, and she grabbed the wig and had me follow her back to the area where the other ladies were trying on their wigs.

"Sit down," she pointed to the salon chair, and I began to feel out of place seeing the crazy looks from the other ladies.

I did as she asked, and she put the wig on me and showed it to me in the mirror.

"Is that okay?"

"Yeah, I guess.  Wow, it is really long, isn't it."

"We can cut it if you like."

"No, it's not a big deal.  It's just for Halloween," I said defensively.

I didn't want to lie.  I kind of promised myself that I didn’t want to be ashamed and lie.  I thought that maybe the best thing was just to keep them guessing, but I felt that I was making them uncomfortable, and felt the need to explain with a lie.

"That's what I figured," said the lady smiling, reassured.

The ladies in the chairs seemed to doubt my explanation.  As I took the wig to the counter to pay, a young, pretty black girl (young for me, perhaps mid 20's) came right up to me.

"What's your costume?"

"Oh...a rock star."

"Oh that's great.  That's a nice wig.  What are you going to do with it after Halloween?"

"I don't know, just stick it in the closet I guess."

"Well you can give it to me if you're not going to use it," she fluttered her lashes at me.

"Un uh!" said one of the ladies in the chairs obviously disagreeing with her choice of flirtation.  Her vocal objection was so loud it still makes me laugh thinking about it.

Of course I'm married, and didn’t do anything else, but I was curious.  I think this girl saw through my disguise, and was turned on by a guy buying a wig.  I politely exited the conversation, and smiled at her, and went home with my prize.  It was an adventurous and trying day to say the least.

Stepping Out: After the First Time (Part 2)

The first time I really had a good chance to really step out, I happened to have a week all to myself.  My wife was out of town you see, and that's a rare occasion.  Usually she's always here, and she would very much disapprove of me leaving the house in a dress. When she told me she was taking a trip, a plan began to come together in my head.

Yes, I know there are some of you who are probably getting an urge to type some sort of nasty message like, "How dare you do that to her.  You're a bad person."

Fine, I'm a bad person.  Can I get on with my story?

My initial preparations took place weeks before.  Ordering makeup was my first mission.  I knew that if I was going to do this right that I needed foundation, blush, eye shadow, mascara, eyeliner, and fingernail polish.  From my other experiences, I knew that I didn’t want to be seen as a man when I was out.

There was a lot to order.  I had no makeup, so I bought some large variety palettes for the eye shadow and blush, several colors of lipstick, lip gloss, and fingernail polish.  Also, I decided to order some other things like false eyelashes, fake nails, and a few other things.  I didn't want my week to come and not be prepared.

The items came, and I stashed them away so that I could initiate my plan.

The makeup sat there waiting for me all week, and then the day finally came.  When I got home from dropping my wife off at the airport, I was in heaven.  The world was my oyster for seven glorious days.  I started by epilating my legs, painting both sets of nails hot pink, and slipping into my best lingerie - an all silk tap panty and camisole set.  It was deliciously feminine, and I was enjoying it immensely, but I knew that wanted more.  My whole plan was to go out dressed as a woman, and that’s what I began to work on next.

Sitting in a chair with boxes of brand new makeup in front of me, I did my best with the makeup that I ordered online.  Unscrewing the top on the foundation, I began to apply it to my skin, and found out that yes, foundation should be purchased at an actual store.  It didn't look that bad though, and I began to apply the other makeup.  A girl would definitely find many critiques in what I did, but all I was interested in was passing while I was out.  As I looked at my reflection in the mirror, it looked to me like the makeup that I applied would do the trick.  All in all, it wasn't bad.  In fact, I think it was rather good, because that day, I don't think I was made by anyone, so I must have done a decent job of it.

It was still morning when I got ready to leave.  I had a whole day of being a woman ahead of me, and I knew that I wanted to go shopping.  That was my goal, to go panty and dress shopping in a big clothing store.  Slipping on a few outfits, I settled on my red dress with an accordion-pleated overlay and a black ribbon that tied at the waist.  It was pretty dressy for a Saturday afternoon shopping, but that's what I wanted to wear.  In my mind I told myself that I could be a girl who was on her way to somewhere formal, and just decided to do a little shopping.  That story sounded believable.

Up until this point when I went out dressed, I had hidden behind the safety of my big sunglasses.  Along with my wig they helped to hide my face.  Even if someone recognized me as a man, they wouldn’t know who I was.  Taking off those glasses was a big risk.  I had a big fear of running into someone that I knew at the store.  Going into the store would be a big risk too.  I had never done something this bold before.  I knew these things, but I willed myself to act. Pulling up to the store, I got out of my car.

"You're really doing this?  You're really going to go in there?  Are you crazy?" I said to myself as I felt myself in that dress in the naked sunlight, and saw myself emerge from the safety of my car.  Walking as gracefully as possible in my black heels, holding my shoulders back, and being loose, I remembered to feel feminine and smile.

I walked past a few people (In a dress!!!!) and they took little notice.  Then it was time...I walked into the entrance of the large clothing store.  The doors slid open, and I looked around at the bustling entrance.  People were coming in and going out and there were all kinds of people in line at the register.

This was the moment.  I took off my sunglasses and carefully put them in my purse.  I kind of waited for a reaction, but there was none.  There were no gasps, no one pointed; I didn't even get any looks.  I think people are just too busy and caught up in their world, for one thing, but I know if they would have spotted a guy in a dress, they would have at least given me that look.

The fact was, though, that they didn't.  No one looked, no one stared, no one did a double-take, no one laughed.  The register beeped, and people walked to and fro.  I was amazed.  I had passed on my first time going out dressed.  Casually and guardedly, I walked down the aisles of the store trying to enjoy my experience.

The fact that the store was so crowded obviously made me nervous.  People were walking by me every few seconds.  It was a lot more to mentally handle than I thought, especially when I was walking in that entrance.  There were so many people, it was intimidating to be in a dress to say the least, but the fact that I got no stares made me want to continue.

Carefully, I made my way over to the intimates aisle, and casually perused some of the panties.  It felt good to be able to touch and see them in person instead of online.  I could lift them, touch them, and it didn't seem weird to anyone because I was perceived as a girl, although I still felt like an imposter who shouldn’t be touching them.  I stayed there for about five minutes, and brimming with confidence wanted to do more, but I felt that this was enough for now.  I didn't want to press my luck.  Going back to my car, I got and pulled away, happy that I was safe, but a bit sad that I wasn’t shopping around people in my dress anymore.

On a high from my success, I drove home and saw another store that was having a big going-out-of-business sale. On impulse, I parked and went in.

It too was very crowded, and being in a dress around all those people was a rush, but still very scary.  Still, I felt a lot more confident since I wasn't getting any looks. 

I don't know particularly what I was afraid when I was at these stores.  In today’s day and age, I didn't have much of a fear of someone ripping off my wig and saying, "Look, he's really a boy!" but I did have a fear of maybe someone subtly pointing and snickering, and maybe drawing the attention of others.  The fact that none of this happened was awesome.

I went home confident that I had somewhat mastered this passing thing, however not all my experiences were as successful.  I would learn that in another outing.

Stepping Out: After the First Time

After the first official time I left the house in a dress - when I drove around for a bit, and the world didn't come to an end - I gained a little more confidence in this exciting choice of what I could do in a day.  I realized that there was a whole world outside that door, and I could be out in that world in panties and a dress like I truly desired.  I tingled at the thought.  Still, the act of doing it was a bit intimidating, but I knew after that first time that I stepped outside, that I wanted to try it again.

A few nights after my first official outing, I decided that this time I was going to get out of my car and walk around for my next adventure.  Now that I think about it, this was a pretty bold move for an amateur, but bold moves have sometimes been part of my forte. 

It was late, probably about 2:00 AM, and I drove down to the area by the casino.  Taking a deep breath, I opened the car door and stepped out in my dress, holding my purse.

It was a weird feeling.  Here I was in the middle of the world wearing nothing but women's clothing, and standing in the street in the middle of the night dressed like I truly wished I could be.  It was a dangerous feeling since I was out in the world in nothing but a thin dress covering my male identity.  In another way, everything else still felt the same. I was the same person, and the casino area was just like it always was.  The only difference was that I was out in the night wearing nothing but a dress and panties.

I walked up the sidewalk past the entrance to the hotel.  Some workers there looked at me.  Did they know?  I couldn’t tell.  I just kept my concentration on walking in my heels, and pretended to look the other way.

I walked the sidewalk loop leading past the casino, and contemplated going inside, but suddenly lost my nerve when a group of people came out laughing, so I just completed the circuit and went back to my car.  That was my adventure for the night, and it was thrilling to feel my dress against my skin in the cool night air, and I was walking around being pretty for all of the world (or at least a tiny bit) to see.  I had actually done it.  I went outside and walked around dressed as a girl!


The next night I repeated my steps, and plucked up the courage to walk into the casino, or at least the area outside of the gaming area with the bars, restaurants, shops.  It was dead since it was so late, but there were surprisingly a few people around.  Some were workers, some were patrons having a few drinks or walking around.  Many of them looked at the girl in the pretty dress walking by in her heels, but I couldn't tell if they knew or not.  I passed up about ten people, then satisfied, walked out of the casino, back to the safety of my car.

It was more of a challenge than a thrill the second time, kind of me willing myself to actually do it.  I was a little tight inside, and I wasn't thinking with a female mindset and enjoying the moment fully.  That made it a bit of a chore instead of a moment where I felt free and feminine.  The whole time, my male mind was on alert saying, "Okay, we're going to walk in.  Keep your shoulders back, walk like a girl.  If anybody says anything, here are my three options..." and that made me feel more like I was costuming than expressing femininity.

Still, it was good to challenge myself and actually do it.  I had gone inside and walked around in a dress!  The feeling sunk in a little more when I returned home.

After that, I began to think of some new challenges and adventures.  I wanted go to the park during the day, go to a store at night, go to the mall.  The thoughts tingled inside me as a whole world of possibilities began to open up to me.  The future new seemed more exciting than I ever imagined.

The Sisssy Truth

I just want to assure you, that if you're reading this blog, then you will be reading the truth.  I think I've lived so much of my life in denial that the truth just feels nice to say online.  Perhaps it's the somewhat anonymity of the internet, but this blog is going to tell the truth about my sissy experiences.

Of course, we all like fantasy, and I'm sure that I'll put some fantasy and fun posts on here eventually, but I'd also like to document how things really feel to me in the moment that I'm doing them.

My hope in this is to connect to a few of you out there who perhaps are experiencing something similar to what I'm going through.

My Bra Adventure that Almost Went Wrong

I was in one of those moods.  If you're reading this blog, then you probably know what I'm talking about - that impulsive crossdresser mood.  I was dressing at home, and my friend called me up, "Hey, I have that thing that you wanted.  You can come by and pick it up if you like."

I really don't like to cross my dressing into the reality of my relationships with my friends, but for some reason, on this day, I was like, "What the hell."

I was wearing a big, thick bra that I like.  It reminds me of being a nerdy girl or something.  Usually I like wearing my petite training bras with their delicate lace edging, but this one is thick - oh so nerdily, sexily thick - with a wide strap at the back and three hook and eyes.  The front is thick too, and a little padded, but surprisingly still an A-cup.

Putting on a thick flannel shirt, it was barely noticeable - I checked in the mirror - and besides, I was just going to pick up one thing and leave.  Cheap thrill, I guess.

I got over to my friend's house, and he's the type of guy who likes to talk.  "We did this," and, "I got a new one of these," and, "Oh come look at this."  Blah, blah, blah, he went on, and although I liked talking to my friend, I began to feel a little weird in my bra.

Suddenly his phone rings and he answers and talks for a few seconds.  When he hangs up, he says, "Our mutual friends are in from out of town.  They'll be over in about five minutes.  You might as well wait for them and say, "hi."

Inside my head, I'm saying, "God damnit," but I agree to wait.  What's the harm?  They arrive, and I greet them.  The guy slaps his hand into mine in an excited manner and goes to give me one of those guy hugs, you know, the slight slap on the back.  He slaps my bra strap, and I freeze at the touch, but he doesn't seem to notice.

Then the girl is excited to see me too, and wants to give me a big hug.  I give her a stiff, distant hug, but her hands go right on my bra strap in the back, which should have been quite noticeable, but I don't think it registered with her.  She did notice my kind of standoffishness - I think both of them did - and I kind of felt bad that I kind of physically rejected their embraces of friendship.

I talked with them for another few minutes, and then said I had to leave.  The girl kept giving me a look, and I wondered if it had finally registered with her, or if she thought that I was being rude and bugging out right when they got there.

I often wonder if they went home and talked and said, "Did you feel something weird under his shirt..."

But two lessons learned:  #1 - Don't mix crossdressing and friends that you want to keep in the dark, #2 - Expect the unexpected

Stepping Out: Before the First Time

Of course I didn't just step out of the house in a dress one night out of the blue.  There were all kinds of test runs leading up to that moment, but the incident described in my last post was the first official time that I stepped outside in a dress - no safety net - but there were definitely some memorable events before that.

I guess everyone starts under-dressing with panties.  That's how it all begins.  The first time I did it, I was so nervous that someone would see, or my pants would come down for some reason.  It was one of those decisions where I was like, "Should I wear these pettipants under my clothes today?"

Pressed for time, I gave in to my morning impulse, and zipped up my pants, forcing myself to have to wear women's underwear for the entire day.  That day, I was so distracted with making sure my pettipants weren't showing, I was constantly secretly checking them, and making sure my shirt was tucked in.  It was more of an uncomfortable feeling than I had anticipated.  I remember being invited to lunch with some colleagues that day, and the whole time I was anxious that the lace hem was showing through my thin, nylon pants.  I kept rubbing it and feeling it to see if it was showing. 

Now I wear panties almost without thinking about it, but at first it was nerve-racking.

After getting used to panties, I would safely find adventures, maybe wearing a bra under a thick shirt or coat (although I'll post another story about that later.)

Eventually, I felt the need to get a little more adventurous.  I guess the first time I really went out fully dressed, I put on a thin, little skirt under my shorts, and a frilly blouse under a flannel, buttoned shirt.  When I got to my car, I discretely stripped out of my male clothes and began driving.

In my mind, I was safe and in a car, and no one would notice, but I soon realized the number of people who actually look at you while you're driving.  There are the cars next to you, and there are people on the street.  Even a guy several feet away at a gas station was looking at my car.  I wasn't wearing a wig or makeup, so I'm guessing that he either saw the shirt and perhaps thought I was a girl, or was wondering why a guy was wearing a blouse with floral appliqués on it, with a bra showing through.

Obviously, I turned right around after only two minutes of driving, and went back to the drawing board, knowing that I better get a wig and some makeup if I was going to go out again.  This was getting more complicated than I thought!

Stepping Out: The First Time

I've only been back in my crossdresing habits for a few years now, but since that time, I've felt the need to explore it a little more with each new, passing day.  It's astounding to me how an old fetish came back so strongly for me.  I mean, one minute I'm convinced that I'm a regular guy, and the next thing I know, I'm sitting here and typing a sissy blog, while being fully dressed in wedges and a cute horizantally striped skirt, and wouldn't have it any other way.

My rediscovery of crossdressing all began again with a pair of panties.  One pair turned into two, then a few weeks later I added a bra.  For some reason, my next purchases were some thigh high stockings and some heels.  Standing there looking at myself in the mirror, I knew that it somehow looked incomplete.

I needed a dress or a skirt, but debated about my growing secret stash of clothing.  One night while online, I saw a dress that I needed to have - a pink dress with a wide, flared skirt.  I wanted it so badly, and on impulse I clicked on the online button and purchased it.

Flash forward to today, and I have so much clothing that my secret stash isn't a secret anymore.  I can dress freely when my wife isn't home, but lately I've had the urge to step out.

Don't get me wrong, being dressed at home is fine for the most part, but my fantasy begged me to step out that door.  It was almost as if I were dressed up with no place to go.

Several times, I played with the idea, and stood on the threshold of that door as if there were some great abyss on the other side.  Several times, I chickened out, but the thrill of the thought was more than enough to drive me crazy.

One night, I got the courage to finally do it, and snuck outside in a dress, wig, some decently applied makeup - but probably not the best either - borrowed from my wife's makeup bag.

Feeling the fear and the thrill as I stepped past the door was intense.  "I can't believe that I'm actually doing this!  This is crazy!  I mean I know I'm daring myself to do this, but I'm actually doing it!" my feet entered the hallway, and I was officially out of the house as the door closed behind me. 

I felt tense walking down the hall of my building.  The sound of my heels on the hard floor at night scared me, since I didn't want to draw attention to myself.  I really didn't want anyone to catch me.  As I walked, my heart beat, and my senses were on alert.  It was thrilling, but mostly scary.  My heart beat in my chest.  Still, there was that thrill of actually doing it.  At times, I looked around and marveled that I was actually in a dress walking down to my car.  I was actually outside in my panties and a dress.  There was such a naked and vulnerable feeling in being dressed like this.  There was no hiding any truths if I got caught.

I got in my car and drove around a bit, and every now and then I'd look down at myself and realize that I was driving my car while wearing a dress.

"Wow, I can't believe I'm actually doing this," I thought to myself.  I never would have imagined that I would be doing this at some point in my life.

In a way it was thrilling, but in another way it was almost a bit underwhelming too.  I kind of built up so many expectations for this moment, but the world didn't stop spinning, lightening didn't come down from the sky.  The only thing that happened was that I had taken a step further down the road of my femininity.  A question was answered, but many more began to pop up in my mind.

I finished my dare, and drove back home and snuck back into the house.  (Not being caught coming back in the house was another peril that I needed to avoid.

That night was memorable but almost forgettable.  Basically, all I did was drive around at night, it just happened to be in a dress.  I guess to me, it showed that it wasn't such a big deal after all, but the realization of this fact is a big deal, the kind that can change a person forever.

And of course there is the nagging urge to do it again...

Sissy vs. Crossdresser

Am I a sissy or just a crossdresser with a need for a thrill?

There are many things that people associate with the label sissy.  Usually it's a very feminine man, perhaps even at the stage of being TG or at least starting on hormones.  Sometimes sissies are pictured as frilly little girls in hyper-girly pink satin party dresses layered in endless bows, ribbon, and lace.  Often times, sissies dream of being kept doing domestic duties or being degraded somehow.  Sissies seem to really enjoy cock, to the point of either being gay or so girly that it just seems natural.

Looking at myself, I wouldn't say that I'm overtly feminine.  I often wonder how much of my personality is real, and how much is learned.  I definitely look back at my life, and realize that I was faking my masculinity (and masking my femininity) at times.  Still, I don't feel like a complete girl, just like a feminine man, kind of a 50 / 50 split.  So the question is, "Am I feminine?" and the answer is, "Yes...and no."  Confusing, isn't it?

Do I want to be TG or on hormones or a full time crossdresser?  Right now, I would have to say, no.  I'm not too sure how much of this is completely real and how much is fantasy.  All I know is that while I would love to toss out all my male clothing, and strut outside to the world and say, "Hey!  This is the real me!" I think that it probably sounds better in fantasy than reality.  I don't hate being a male, and I don't know if I'd want to give up everything related to my male life, although the thought is tantalizing.  Right now this is a "Probably no, but then again, full time crossdressing does sound exciting..."

Frilly Dresses - Although I have an intense fantasy of being feminized as a youth - and I even went out and bought some of the sissy dresses, panties and nighties - I'm going to have to say, that being a satin sissy really isn't my thing.  I have a babydoll chiffon-over-satin dress that I wear as a nightgown that I enjoy, and I have a satin nightie that I like, and the frilly panties can be fun and different, but when it comes down to it, most of the time I just prefer to dress as a woman.

Domestic Duties - Once again, I often have a fantasy of being made to clean, and have even pretended that my wife has commanded me to do the dishes or some similar task.  At first, it's sexy - maybe for about five minutes - but after that, it just becomes work.  I get wet, dirty, sometimes sweaty, and I think about how much easier this would all be in regular clothes.  Besides that, I'm kind of lazy, and prefer to be in my own world instead of servitude.  For this, I'd say maybe if I got into the habit, it would be fulfilling, but I'm on the fence with this one too.

Cock - You know if you would have asked me a few months ago about cock, I would have drawn a firm line in the sand.  "No way.  That's something I'm not into!"  But being on sissy websites, I seem to be inundated with it, and toying with this taboo has been interestingly exciting at times.  But is it me?  Not really.  I'm still attracted to women, although the thought of sucking a cock makes for good sissy fantasy.

So this brings up the initial question:  Am I a sissy?  Do these things just make me a crossdresser with a vivid imagination? and the only answer I can come up with is, "I don't know, maybe."

Up Until This Point

Although a sissy beginner, I have a long history leading up until the point that I first started entertaining thoughts of sissy delights.

I won't bore you with all the details, but I did start crossdressing around age 11.  I've often wondered what possessed me to don those panties for the first time.  I know part of it was the sexual thrill, but I've often wondered why wearing those panties was like a bolt of lightning to my soul.  (I think I know the answer now, but more on that later)  The powerful feeling of those panties was like, KA-BLAM!!!  I just stood there shocked, having never felt something so strong in my life before.

After that, I vowed to myself, "Never again!" and I think it was about an hour later that I was sneaking them out of the laundry again.

I was hooked for a while, but towards the end of high school, I started to taper off in my crossdressing.  I knew it wasn't cool, and I wanted to fit it.  Eventually I broke myself of the habit, got some girlfriends, got married, and I had completely forgotten about it for years.

One day, I was kind of sexually bored and reading some femdom porn where the guy had to wear panties and clean the kitchen.  It was sexy, and I remembered how it used to feel.  On a whim, I went out and bought a pair of panties for my entertainment.  They did the trick, and embarrassed, I threw them away, but an old creaky closet door in my head had cracked open again.

Flash forward to today, and that closet door finally opened, and all kinds of mental baggage came tumbling out.  Dresses, skirts, panties...I have closets and drawers full of them, and I'm starting to realize that it's more than just a sexual thrill.  This whole thing means something else.

Of course I can look at it all rationally, and know the reasons for my crossdressing, but deep down I feel there might be something else awakening in me.  It's both a frightening and exciting experience.

Am I a Sissy?

It seems sort of a silly question to ask from someone writing a sissy blog, but the answer is that I really don't know.

I guess it brings up the question of, "What is a sissy?" 

Sure, you laugh to yourself, and say, "Well if you don't know what a sissy is..." but I don't think the answer is that easy.  I don't really know who I am right now, and this is why I'm exploring.

There are some things I feel that I like; there are other things that I thought I'd never like, but I am starting to enjoy; and there are some things that I still have yet to discover.

The short answer is, that I don't know.  That's what I'm trying to discover.  That's what this blog is about.

Why Start a Sissy Blog?

There are two reasons that I wanted to start this blog.

#1 - I thoroughly enjoy reading other sissy blogs, but it seems that out of the many blogs out there, a lot of them are about the person who is in the advanced stages of being a sissy.  I'm personally at that stage right now where I'm exploring - a sissy beginner - and I'd like to document my progress and capture my thoughts as I move along in my discovery of this new world.

#2 - I like participating in sissy forums, and I find that I post a lot about my feelings and adventures, almost to the point where I have too much to share on a forum, so all of these thoughts are going to spill over into my new blog.  I hope that a few people out there enjoy some of my thoughts.