Diary: Writing a Diary

Several months ago, I started keeping a log of my crossdressing sessions. I've been curious about identifying habits, patterns, and themes over time. I had an identical process years ago, but I stopped when it became tedious to record all the details after the fact.

Recently, I realized that it would be sort of fun to describe at least some of these sessions publicly. There's some value to others in reading about my real-life experiences; and there's a certain thrill I get out of writing about it. There's a huge amount of fiction out there that purports to do this, but veers into fantasy. This is going to be quite a bit more boring, but will likely include some description of what I'm fantasizing about.

Enjoy!

Busted

It's been very quiet around here for a long time now. But, I've continued to dress up mostly in swimwear. I got into a naughty habit for a while earlier this year, which I'll describe some other time. The usual routine of indulging in some femininity while my family is out of the house continued happily, until a couple of weeks ago.

My wife found my stash.

Or rather, I had absent-mindedly left it out, in plain sight, and went to work for the day. She texted me asking what it was, and I knew I was sunk. I felt physically ill. I considered coming up with some crazy explanation, but ultimately, I knew I had to tell her the truth, as painful as that would be.

So when I came home, I sat her down, and told her that the bathing suits, lingerie, and shoes in the bag she had found are mine. And that I wear them. Because I like it.

She was horrified. She felt like I had betrayed her. It's a huge lie, that I've concealed this from her for over ten years. In fact we just came home from a 10th anniversary trip when this happened. She suddenly felt uncomfortable in my presence. She didn't trust me with our son.

We spent the next several evenings talking about my secret. I told her almost everything. She's mostly concerned that I'm gay, and I assured her that I'm not. I'm actually quite confident that I'm not, in spite of all of this. She made me throw away my stash, while still feeling bad about it. She's very conflicted about it. She wants me to stop doing it altogether. I told her I would, and I'll really try, but I also told her that it's not really possible to stop. For now, I'm more than willing to at least pause so she can process it.

After we talked, each evening, we made love. We have always been very close and intimate and in love. Except for this, we've had a very open and honest relationship. In some ways, it's brought us closer together. She feels like she needs to fuck more to break this habit from me. She doesn't understand that it just doesn't work that way. The sex has tapered off a bit the last few days, but I've been constantly horny every since she found out. I'm thinking about wearing women's clothes non-stop.

She asked me not to wear her things. I promised her I won't. I really will try not to, as much as I'd love to. It's especially hard that I don't have my own things anymore. She sort of understands that I need to do it sometimes, but she really doesn't want me to.

When I told her that my habit was to wear things while she's out of the house, at first she felt reluctant to leave me alone, for fear that I'd do it again. I'm alone now, and I'm sure it's crossed her mind. It's like a test. I want to tell her that I desperately want to order some things for myself: a swimsuit, some panties, a bra, and even some shoes. I'm taking a business trip this week anyway, and I don't know how I'll handle being alone in a hotel room with nothing feminine to wear. It would have been a perfect opportunity, but now I'd have to buy something first.

She's not at all interested in ever participating in this with me. She wants a manly man, and this utterly turns her off. I still hold out hope that she'll come around. It's too soon now, though. The alternative is that I continue to do it in secret, and she may be OK with that. She'd rather not even know.

Meanwhile, I have felt somehow more free since she found out. It's a relief that I no longer have to bear this secret anymore. I fantasize now that eventually she'll accept this, and I can openly keep some feminine things in my dresser. I'm already toying with ordering some things. But I need to be patient.

She doesn't know about this blog yet. She doesn't know the full depths of my fantasy. I did explain to her that it's all about becoming a woman. She doesn't understand it at all. But she still loves me. She says so, and her actions prove it. This does put some doubt in her mind. I'm doing what I can to convince her that I love her still, that I'm the same person she married. But from her point of view, because she never knew this side of me, and it's not something she ever wanted or expected, she feels like she didn't truly know me. So I'm not at all who she thought I was.

Commitment

It's hard to find the freedom to fantasize about being a woman at this time of year. All the same, the only way this blog can work is if I commit to posting something regularly. So that's what I'm trying to start now. I'm aiming for at least one post per week. I'll keep mixing fantasy and reality, but everything is clearly labelled, so there should be no confusion.

Meanwhile, I have to use my precious little time wisely. I'm continuing to work on some fantasy stories, but I can't help but spend a lot of it on just looking at dirty pictures and masturbating.

Yes, I'm Still Here...

It's been over a year since I've posted here. What a shame.

I've been writing my stories very slowly. There just isn't time, now that I have an active toddler. When I do get into the mood, which is still quite often, I'm consuming, not producing. I'm sorry, but I haven't got anything to show you.

My enthusiasm for cross-dressing has changed somewhat over the last year. It has gotten to the point now that whenever I do it, I feel rushed, so I end up climaxing long before I want to. Sometimes I don't even get a full erection. More often than not, I now either borrow my wife's things, or wear nothing and just fantasize while I wank. It has become much more of a cerebral activity. I rarely go to the trouble of digging out my stash anymore. In a way, I like it better like this. The duplicity wears on you after a while.

Thinking back, I used to take such huge risks. I used to wear swimsuits in the garage early in the morning while my wife slept. I no longer feel confident enough that I can get away with such things, and I no longer even feel that it's necessary.

Meanwhile, whenever we have sex, I'm secretly fantasizing about being her, or about becoming a woman. It's the only thing that turns me on. She still hasn't got the slightest clue.

Part of the reason I stopped posting here is that I'm not sure what this blog is for. What do I want to do here? There's such a huge mix of different things going on here that rather than try to continue doing something -- anything -- I just throw my hands up and write nothing. It feels like there are two voices here: the fun one with the sexy fantasies, and the depressing introspective meta-voice of this post. I'm beginning to wonder whether the two should never co-exist. I think they need different blogs.

I've noticed that the blogs that turn me on are most likely heavy on embellishment. Confessional stuff like this is pretty rare, and for a good reason: it's anti-climactic, for the most part. I don't feel quite right about feeding people all kinds of bullshit about my sex life, but I do feel like there needs to be somewhere to reveal these dirty little secrets of mine. As for my fantasies, they'd benefit from being unburdened by any pretense to truth.

Stay tuned. Things are going to change.

Story in the Works

I have a new story in the works. It's been a very long time coming. It's been fun and exciting coming up with the outline, to the point where it's all I can think about, even when I'm making love to my wife. It creeps into my mind when we fool around, and I fantasize about the juicy bits so much that it keeps me hard and ready to go at any time.

The story is about two life-long rivals, constantly competing with each other over money, power, sports, women, and anything else you can think of. One finally gets the upper hand, and utterly destroys the other, taking possession of everything he has, including his woman. Thus defeated, the loser is forced to become his rival and ex-wife's sissy maid slave.

There's nothing particularly revolutionary going on there, but it's awfully fun to write! I'll post some juicy bits as a teaser when I'm further along. It's going to take some time, though, since I can't safely work on it very often, so please, be patient.

The Long-Lost Diary

At last, I've gotten around to publishing my long lost diary, which goes all the way back to the mid-90's. It tracks my thoughts and fantasies through all those years.

Feel free to start at the very beginning. I've added some commentary here and there to explain some things. Rereading it was fascinating for me, as I relived some key events in my development as a sissy. Here it is for posterity, for the whole world to enjoy. Names of people and places have been censored to protect the innocent.

Enjoy!

I Finally Got My Swimsuit!

My exchanged swimsuit has finally arrived! I lugged it around all day yesterday, unable to stop thinking about it. I couldn't wait to try it on to see if this one fits. I even considered slipping into it in the restroom at work, but I was thwarted by the impracticality of having to take off all my clothes with the risk of people coming in at any time.

I eventually put it on late at night after coming home from a planned excursion. I snuck into the bathroom to put it on, with the pretext that I was using the toilet.  It was still somewhat difficult to get my shoulders through the arm holes, but it was definitely much easier. It still felt like a trap that I couldn't easily escape from, which in itself is arousing. The bathroom wasn't adequate for truly enjoying it, so I decided to retire to my office to continue. To that end, I wanted to hide under my male clothes just in case my wife got up. I couldn't risk just putting my white t-shirt over the top of the suit, because it would be visible through it and would stick out at the back of my neck, so I zipped it down and shimmied my shoulders out without too much trouble, and peeled the top down and folded it into my pants. The bottom part stayed as it was.

Once I was comfortably hidden in my office, I was better able to appreciate it. It took a while to get a good rhythm, given the circumstances, but I did manage to succumb to its femininity. Amazingly, I found it much more difficult to get out of, weakened as I was by my climax.

I'm looking forward to more in-depth experiments.

Disappointment

Sadly, my wife didn't end up going on her trip. She's feeling too sick from the pregnancy. Therefore, there will be no girlie bender.

Life goes on.

Diary Transcription Project Continues

Over a year ago, I had started blogifying my many diary entries from years gone by. I had abandoned the project because it's somewhat tedious, but now I'm interested again.

I have accumulated vast amounts of writing about my fantasies over the years, and it seems a shame to have them hidden forever. Of particular note are some epiphanies I had along the way, and how I marked major milestones in my feminine development.  The beginning of the diary itself was a major turning point in my life. It was the first time I ever admitted to myself that I love wearing women's clothes. Moving past denial after so many years was instrumental in making me the happy crossdresser that I am today.

Incorrigible

I've had a decent bit of fun with the garter slip I ordered, but not as much as I'd imagined. Not yet, anyway.

This happens to me every now and then with certain outfits, particularly ones that I'm experimenting with. I latch onto a lovely picture of some garment, and I become obsessed with wearing it. Then I get one, and it's not as much fun as I'd hoped.  In general, I think the first time is never as much fun as later incidents. Often, however, the same garment later becomes one of my favorites.

For example, there's the blue one-piece swimsuit I bought years ago. I had picked it out of a rack at a drug store, and gotten nasty looks from the cashier. When I first wore it, I didn't like it at all. Eventually, it became the one thing I wore most of all! Then there's the teddy I ordered from VS a few months ago. I was unhappy with it the first couple of times, but now it's definitely one of my favorites. I haven't worn it all that often, but something about the lacy fringe on the leg holes drives me absolutely crazy with femininity.

Anyhow, I found my stash to be quite complete after that last purchase, so I didn't renew my P.O. box. I have so much girlie stuff now that I can't even hope to keep up!

But there's always more stuff to be had.

T__ decided to do a bit of spring cleaning. She was going to donate a bunch of stuff, and while she had stepped out for a bit, I inspected the items she was getting rid of. Sadly, one of them was the bikini panties, missing their bra, which she often wore when we first started seeing each other. I've certainly worn those panties far more than her. Those are now gone.  But at the bottom of one of the boxes was a little black dress that she used to wear in those days. I saw an opportunity to have something I wouldn't otherwise be likely to get for myself, so I stashed it away.

Yes, I now own my very own little black dress! Finally, I can wear something reasonable with my stockings and knee-high boots!

I'm wearing it now, along with some pantyhose I bought at the grocery store the other day, and my VS satin panties and bra. I feel like I'm living the dream now.

Shipment #3

I was pretty saturated with the last shipment. I have so much feminine stuff now I don't know how I'll ever wear it all. Remember my declaration that I'd focus on swimwear? Well not too long ago, I got tired of all the bikinis, and got a strong hankering for some lingerie.

On a strong impulse, I went for the white garter slip I'd been dreaming of for months, and an appropriate pair of white panties. They finally arrived today.

I must admit, I wasn't feeling particularly keen on my little adventures lately. With the package in my car with me on the long ride home from work, I tried so hard to get myself into a little fantasy so I could get more enthusiastic about my new frillies. Try as I might, I just couldn't sustain a fantasy. Too much else on my mind.

Tonight was perfect for bringing this home, because the wife is out. When I arrived, I promptly unpacked my goodies, and inspected them, more interested in hiding them than wearing them. When I felt the unreal softness of the slip, my heart melted. It's exquisite! And now I had to put it on!

I rushed into the bedroom and squeezed myself in. It's wonderfully tight, all the way to my butt, where a set of garters await my stockings. It clasps in the back like a bra, which gives that wonderful feeling of being harnessed into something feminine, with no way out. The panties are OK. I have similar ones. I think I would have preferred something a little different, but I'm sure I'll enjoy them anyway.

Tomorrow morning, I'll put them both to the test. I'll have the time to put on some stockings and shoes with them.

Saturday will be even better, as I'll have the entire day and night to myself!

Another order...

Having committed myself to a life in women's swimwear, I stumbled onto a 20% off sale at Victoria's Secret.  I spent less than $30 on the ringed bikini, and a plain neon pink string bikini.

This is what I really wanted in my original order, but they no longer have it in pink, which I would have preferred.  This will do just fine.

Why Fight?

Whenever I browse for girlish things to wear, I inevitably end up concentrating on swimwear. Even before I got myself a PO box to get secret deliveries, I would always spend most of my time contemplating bathing suits.

This goes back to my initial fetish for swimsuits, which were, during my formative years, the only reasonably sexy garments available to me. To this day, I still wear swimwear far more often than anything else. In my nascent fantasies oh so long ago, I used to imagine that lingerie was the next level up, an unattainable wish that I would never be able to fulfill.  You'd think that by now I would have made the switch, now that I have virtually unlimited access to just about anything.

I've already placed an order. I'm already getting excited about my next one. And what is it that I'm mainly interested in? Swimsuits! I want to have every possible kind of swimsuit!

It's really quite ridiculous. I keep telling myself that I need more lingerie, that I need to build a panty collection, like any self-respecting sissy. But when I browse, I can't help but gravitate to the swimwear.

So why fight it? It's what I like, isn't it? So what if I have more swimsuits than any woman even has? So what if when I get horny, I have dozens of bikinis to choose from? I might as well just embrace my preverse need for bikinis, and enjoy it!

Therefore, I've decided to stop trying to conform to what I think I'm supposed to do, and either explore every possible facet of swimwear into infinity, or get this swimwear fetish out of my system, whichever comes first.

I hereby embrace my predilection for swimsuits, swimwear, bikinis, monokinis, tankinis. All hail the mighty bikini!

First Order

Having secured a PO box for deliveries, I wasted no time in starting to put together an order from my favorite vendor.

The main mission was to fill in my underwear collection.  I realized recently that my current stash only includes two pairs of panties, one of which is part of a lingerie outfit.  I thought it would be important to embrace my feminine side by wearing panties more often, possibly even when out in public, but I would need a whole lot more for that to be possible.

The first order of business was finding suitable panties, and then getting a matching bra. The ideal panties, in my mind, are silk or satin, and off-white. This is perhaps the first distinction I was able to make between boy underwear and girl underwear, and it seems quite true in its simplicity.  Surprisingly, this wasn't the easiest thing to find at a lingerie store, given that they specialize on the edges of the spectrum: fantasy lingerie from the minds of horny men on one side, and comfortable everyday cottons on the other.  However, I did pick out a winner: ivory satin bikini panties with lace accents, and a matching bra.  For good measure, and given the discount when buying more than one, I also selected the same in black.

Then I fell into the usual trap: I spent an inordinate amount of time looking at swimwear. I wanted something cheap to fill out my collection, and wanted something with decorative hardware. I almost ordered a lovely bikini with rings at the sides, but I balked at the color and pattern, and anyway was unsure whether it really did come with the rings. I instead chose a double-string bikini, in the same metallic silver of my old favorite bikini that I wore hundreds of times back in the day.

The bra I chose was a push-up halter, pictured here in gold.

Then I threw in a super-cheap but sexy teddy just for fun.  It was only 6.99, and the lace and bows at the legs were simply too pretty for me to pass up at that price.

Now I was ready to complete my order, but I wasn't quite convinced.  The total was rather high, and I wondered whether I was really getting exactly what I wanted.  I thought about ditching the teddy, but it was so cheap as to make no difference.  Then I thought about the underwear.  Sure, it would be nice to have more underwear, but I wasn't even totally sure if the kind I had chosen would be suitable. I realized that I was getting sucked in by the discount for buying more than one, and that it wasn't a very good deal after all.  So on a whim, and with a devilish grin, I dropped the black panties and bra, and added a pair of super-cute shoes.


I've wanted some tall strappy sandals for a long time, but I've never had the courage to buy any.  I've bought FMB's, but I've grown tired of them.  At last, I will have appropriate footwear to feed my perversions.

I filled in my info, and clicked submit.  I now have a bunch of lady clothes on their way to my secret postal box, and I can't wait to get my hands on all of it.

I'm particularly excited about the shoes.

The Next Level

I've been going crazy reading a set of blogs about some college girls who turn a couple of guys into sissies. Their stories have me obsessed with emulating their predicament.

Over the last few days, I've caught up with all of their collected posts, in order. Every time I come near those blogs, I'm possessed with such an intense desire to feminize myself that I can barely get through reading a post without rushing off to my secret stash and indulging myself.

Alarmingly, as satisfying and gratifying as these sessions have been, I inevitably return moments later, and find myself in the exact same position. No matter how hard I come, I still want more the moment I allow the fantasy to re-enter my mind.

As such, I find myself at a crossroads. For years, I've been dressing up in secret, on average, about twice a week.  It'll range from full-on lingerie to simple little prances in bikinis.  I've even been documenting all of these incidents in a spreadsheet for the last two years, to keep track of all the things I've worn, and how much fun I've had wearing them.  Part of the reason why I've gone to such lengths to track my excursions into womanhood is to figure out just how big a part of my life it really is. I'm a married man, and my wife has no idea; I struggle with hiding my secret from her, and wonder if there's any way I could ever tell her. Another solution would be to stop, but we all know that's not feasible. I've been doing this since I was about 10, and I tried to quit many times when I was a teenager, but I always found myself fatally drawn to resume, always with more intensity. There have been dry spells of months when I didn't feel any particular need to do it, but eventually, the desire comes roaring back, and I'm mincing around in panties again.

In short, I know what I've gotten myself into, and in many ways it's not good. This fetish is baked into my psyche. I'm a sissy, and all of my sexual thoughts revolve around it. Even when I'm making love with my wife, I'm invariably fantasizing about what it must feel like to be her. She has, as I've mentioned, no idea.

My stash is anemic by most sissies' standards. I've had to keep it that way for it to remain well-hidden. But my needs are outgrowing my modest collection. I borrow a lot from T_'s wardrobe, but it's always stressful to avoid leaving suspicious stains or wrinkles, and to put everything back exactly as I found it. Also, she doesn't have everything I want, and some of her clothes (i.e. ALL of her shoes) don't fit me. There are some things she'd never wear, and for those, I've had to take matters into my own hands.

I've developed a strategy for hiding my stash, which I haven't followed particularly well. Sometimes I keep it all in a place where even if I died suddenly, nobody would find it. Currently, I keep it hidden in almost plain view, although under lock and key, such that it could be discovered at almost any time by a determined snoop. Since I never want my wife to find out, I fear that this will lead to disaster. But I need my girlie stuff close at hand! The super-secret spot is not easily accessible, and therefore not conducive to easy pleasure sessions. I had been thinking recently of returning my stash to this spot, for fear of getting caught. Then I found those blogs.

Now I'm seriously considering expanding my collection in a big way. I realized as I followed the sissies' progress that I have very little actual underwear! In fact, I am so biased to swimwear that it takes the place of everything else. Therefore, I desperately need at least a matching bra and panty set, so I can pretend that I have the beginnings of a realistic feminine wardrobe. Then I need to get some variety of panties and a few bras to fill it out. And of course, what would be the use of this if I didn't wear them as often as possible?

That's when the idea popped into my head that I, like the blogging sissies, should wear panties at work, in secret, since it would be so easy for me to do given T_'s schedule. Now I'm obsessed with getting started. I wore my one pair of everyday panties (a blue stretch lace boyshort) all day at the office today.

Now, the trick is getting my new stuff. I tried in the last couple of days to go to Victoria's Secret, but I chickened out. I just don't have the nerve to do it. So instead, I've hatched up a plan to get a post office box, and order everything I want.  I would pick up my deliveries during my lunch break, and T_ would never know about it, because I'd stash it all away before she comes home. I can even return stuff I don't like, without having to face the humiliation of going into the store in person! Imagine the possibilities: lingerie, swimsuits, skirts, dresses, SHOES, SHOES, SHOES! All with minimal chance of ever getting caught!

So, the big question is: am I nuts? Just a short while ago, I was going to tone everything down a bit and try to scale back. Now I've swung completely in the opposite direction, and I'm planning to scale up, dramatically. I'm succumbing to my perversion even further than I ever thought possible, by planning to wear women's underwear all day, five days per week, from now on, and essentially placing no limit on what else I can wear.

Should I wait a bit to come to my senses, and abort this crazy plan -- which I've fantasized about before, but gave up as impossible? Or do I go ahead with it anyway, and increase my risk of being caught?

Is it worth it?

Right now, as much as I resist it, the answer is a resounding YES, it is worth it.

Changes

I'm taking a new stab at this. Previous attempts were far too explicit and potentially non-anonymous. What can I say? I was in the grip of my delusions. Looking back, it was little more than an exercise in exhibitionism.

While I stopped posting out of sheer embarrassment, I haven't stopped dressing up like a girl and frolicking about like a randy tart. I've also developed some ideas for content offline, which I am glad to start sharing. I have multiple streams of thought to dip into. Perhaps someone will even read it.

Updates will be irregular and infrequent. There will be no photos.

Hello, world.

Welcome to casualtranny. Just remember, all of this is a big secret. I would never admit publicly to anything I'm going to say here. This is a testbed for some kinky ideas I have always had. This is the painful first post.

Enjoy!