Why Am I Dressed Like This?

Printer-friendly version
Blouse.jpg
Photo by Anna Shvets: https://www.pexels.com

Preface

Every so often I check the Retro Classics Page here at BC just to see if I missed a good story. Today there was an entry for Emma Ann Tate's Software Update. Since this story continues my own Reprogramming Your Life, I was interested in the comment.

Now, naturally I couldn't just read the one comment, so I read them all. One by Patricia Marie Allen that included the phrase that inspired and became the title of this piece. When someone asks me 'where do you get your ideas?' they don't know what a can of worms they might be opening. Thanks to all of you for the inspiration.

A Philosophical Question

Can you call it a celebration when the root of the thing is the sale of your child? Now there's a question worthy of a philosophy seminar at some obscure university with half a dozen earnest young women and men quaffing coffee - or maybe something stronger - as they sit in a circle with some gray-haired instructor – pardon me, Professor – as he leads the discussion. Naturally you would need to hold said discussion in a venerable, wainscoted (dark walnut, of course) library amid shelves of pretentious tomes by such venerable figures as Locke, Kant, Nietzsche or Stan Lee.

Perhaps there will be references to the immortal Freud, not neglecting his Oral, Anal, Phallic, Genital and Latent stages. Someone is bound to come up with Plato, where in his Republic he proposes that children be taught the value of collectivity, community, and being one with the State. I don't really like that one since I sold my child for several million bucks and if the State owned her I would be out a whole pile of money.

Now that I've got you worried that I am indulging in child trafficking, let me assure you that I'm talking about my intellectual child, that is to say the software I wrote that I developed into a good-sized company that was bought out by an international megacompany. No flesh-and-blood humans, or even animals, were harmed in this story.

The Celebration

When the papers were signed, the money transferred, the taxman satisfied and the dust settled I decided to go out for an evening to celebrate. Since I was in a strange city for the fruition of the deal, I went out to a club and – to put it bluntly – I drank more than I have ever done in my life. I have vague memories of dancing with several women, being introduced to multiple curious concoctions of exotic liquors that my companions swore were hidden gems of the local culture, and having a pneumatic personage sucking on my semi-erect member until I was screaming with need. I do remember her red bra bouncing as she knelt above me and admiring her breasts within it. What happened when she finally relented and released me was still a mystery, other than a golden aura of an overwhelming satisfaction.

I plead temporary insanity, your honor. I don't drink that much and as a certified tech nerd I don't go dancing in clubs with any regularity. With a prodigious pile of cash in my pocket I had some nebulous idea that that's how The Beautiful People celebrate.

The Aftermath

When I awoke the next afternoon in my hotel room I certainly could not be included in The Beautiful People no matter how hard you tried to stretch the definition. Do The Beautiful People awake with an insane and urgent need to piss? I don't know the general answer to that question, but I certainly qualified on a personal level. Hell, what's one more insane urge after last night?

I stumbled out of bed, thankful I was not covered by any sheets or bedspreads, as I would have certainly been unable to cope with removing my numbed extremities from under them. Something felt off as I tottered to the bathroom, but the insane urges in my nether regions drove such thoughts from what was left of my mind.

I finally navigated to the toilet and realized I was not going to be able to stand and deliver as a manly man does, I was a bit shaky. So I reversed and sat, which is when I realized I was wearing underwear. My bladder was predictably annoyed when I rose and fumbled them down, then sat once more and let things rip. A minute or so later, with the pressure relieved, I opened my eyes and realized that there was red nylon stretched just above my knees.

If my slowly reviving brain had been up to it at that moment I might have called that surreal. I have never worn anything around my groin but white cotton. No boxers with hearts or speedos with contrasting elastic about the legs and waist. White, cotton, y-front, ordinary men's underwear. Just how did I end up in red nylon?

No answer came immediately, but a flash of red bra did pass through my consciousness. I remembered being fascinated watching that bra move as I was losing my mind with pleasure. Perhaps the red nylon on my thighs was somehow related to the red bra?

I stood up and looked more closely. I was wearing a pair of red panties, no doubt about that. About that time I once again realized my balance was a bit off. Looking in the bathroom mirror I saw I was wearing a frilly white blouse with a big bow tied in the front. That must have released the logjam in the rivers of my mind. I had last seen that blouse on the woman who I was dancing with last night. In fact, now I remembered her removing the blouse and revealing that red bra.

OK, I now had two facts to ponder, but no answers. I further reflected on my reflection in the mirror and realized that the blouse on my body showed evidence of breasts beneath it. Now this was getting very weird. Just why am I dressed like this?

At that point a couple of those logs that had been released from the frozen pond of my mind must have slid into my cortex and knocked a few more memories loose. The woman who shared my bed last night was… was… not a woman. She was trans… trans… what was that word?

Transgender! That was it! However, by the time I realized that her breasts were not a part of her body she was playing with my penis and urging me to the bed. They say that your small head can override your large head, and I had learned first-hand that it was undoubtedly true. She certainly had magic hands.

So now, standing in the bathroom the earlier and later memories joined up and I was recalling last night in some detail. I returned to the bedroom and sat at the little table there. Noticing the room service menu, I picked up the phone and ordered something to eat. Breakfast after the Noon had come and gone? No problem. Certainly we'll just leave it on a cart outside your door and knock.

The next memory was a bit harder to face. When I had masturbated there was always the results to clean up afterward. One of the nice things about fellatio was there was no messy cleanup, so when Paula – her name was now accessible – had finished she was able to remove her panties and slide them on to me. There certainly was no resistance from my penis as it was happily asleep.

With a giggle, Paula reached in her bra and removed her right breast, placing it in my hand. It was warm and soft and felt like the real thing; at least from my limited experience I was unable to tell any difference. Well, I hadn't felt a free-roving breast before, but what the heck? Out came the other one and off came the bra. Before I knew what was happening She threaded the straps over my arms and fastened the thing, then she inserted her still-warm falsies.

She smiled and lay on the bed, inviting me to learn just how to do what she had just done. I wanted to make excuses as I replayed the next few minutes of the evening, but maybe I was still a little drunk, certainly I was still a lot high on sex, and realized that I had absolutely no reason not to try something new. Wasn't that why I decided to go out and celebrate?

She was a good teacher, at least she said I was a damn good student when we were finished. I invited her for the night, but Paula had obligations in the morning. With a grin, she offered to leave me with her clothes if I would lend me some of mine.

Really?

Yeah, really. She was sure I was going to enjoy dressing up as I looked pretty cute even without makeup. As I played this back there was a knock on the door and a mumbled 'Room Service.' I waited a few minutes and cautiously opened the door and brought in the cart. Hanging on the clothes hook by the door was her skirt, so I put it on and settled down to have breakfast. That's when I learned that breasts – whether real or false – have a positive affinity for egg yolk.

Taking the cart out to the hall I noticed there was a note on the door.

Hey Lover -

Sorry to run out, but a girl has to earn a living even when she's not a girl. Welcome to my world, I hope you learn to like the trans life, you certainly seemed to take to it last night. I always worry what will happen when I take a chance with a man, but there was something about you that made me think it would work out.

You do a damn good blow job for an amateur! Here's hoping you get lots of practice and go for the gold!

Thanks to your generosity I'm going to be able to get a really good pair of falsies to replace the ones you're wearing. You didn't have to, really, but a girl does appreciate a generous lover.

If you still like being a girl in the morning, come on down to the Transformations Studio on First Ave, they can help you learn how to do it right. And no, they will not give lessons in fellatio. Not that you need much more help, darling.

Thanks for a great time, and I'm sorry you don't live here so we could get to know each other better.

Paula

My appointment at Transformations is at 10:00 tomorrow.

up
70 users have voted.
If you liked this post, you can leave a comment and/or a kudos! Click the "Thumbs Up!" button above to leave a Kudos

Comments

What Else?

joannebarbarella's picture

Did Paula leave? I hope there were some shoes.

New Beginnings!

Emma Anne Tate's picture

Fun story, Ricky! I hope your suddenly wealthy and adventurous protagonist enjoys the walk on the wild side! I wonder how she might look after her visit to the salon?

IMG_2365.jpeg

Emma

Paula

I have a trans friend with the name of Paula and it sounds like your MC just met her.