The Realization

"Oh Lauren, I'm so sorry," cried Aida. "I was just so damn mad at that bitch with her 'bring your fiancé crap. She knew damn well that I don't have a fiancé."

"No, you've got a fiancée."

"What?"

"You've got a fiancée. I heard you say it myself. I think I just got promoted from girlfriend-first-class to fiancée for bravery under fire. Actually, considering what was happening at the time it should be bravery under water. I didn't realize that a woman getting wet with passion was quite so literal."

"You! You…"

"You wouldn't hit a poor, defenseless woman, would you?"

"Are you serious?"

"I told you I tested out halfway between man and woman. I even tried on my sister's bras a time or two when I was a horny teenager. Think we can tip the balance in what? Three weeks, was it?"

"Less this weekend. Jesus Lauren! All I was hoping for was a good time in bed, not a lifetime commitment."

"Engagements can be broken. Just think of the fun we could have with a spectacular fight at the party."

"You devil. You know I was joking about the girlfriend bit."

"Sure. I kind of liked the joke, though. I also like a challenge. At least we should be able to share the clothes if we try."

"You get your own lingerie, fella."

"Hey, I've already gotten into your panties, why not your bra?"

"Because… I don't know - just because!"

"I suppose my job is usually talking you out of your bra, not talking me into it."

"I haven't smoked any pot in like, months, but this conversation could only be happening if I was high."

"Girlfriends don't let girlfriends get high?"

"Maybe it's time…"

"Actually, one of the marketing plans I critiqued was for a dispensary that wanted cute names for the various kinds of pot. My best advice was to steer clear of anything that might attract kids. Things like cotton candy or sweet treat."

"Seriously?"

"Marketing run amok."

"So how would I market you as my fiancée?"

"Depends on the market. Are we going for sweet and demure, brash and bountiful, or maybe kickass bitch?"

"God, that last one is tempting!"

"Not sure if I could pull it off. I'm more the sweet and demure type, I think."

"How much cleavage could you show as a sweet and demure fiancée?"

"Depends on the makeup job. I could ask my father."

"Your father? You're shitting me!"

"Seriously, dear old Dad has some buddies in the movie business and those guys can do amazing things with makeup and silicone."

"You would actually tell your father you want his help to turn his son into a sweet and demure woman so she can taunt the raging bitch mother of a woman you hardly know?"

"I think we know each other quite well, at least in the Biblical sense. Here, just listen."

I finally found my cell phone in the pocket of my pants, which had gotten kicked under the bed in our hurry last night.

"Hi Dad!"

"Hey, son. What's happening?"

"You are going to have a hard time believing this. Maybe you ought to get Mom so you won't have to try and explain what your crazy child is about to do."

"It can't be that bad if you want your mother to know."

"Depends on what you mean by bad, Pops."

"Hang on a minute… MAYA! Lauren's on the phone… OK, she's here."

"What's this all about, Lauren? Mom asked.

"First, I want to introduce you to my girlfriend, Aida. Aida, my parents Andre and Maya."

"And when were you going to get around to telling us about this girlfriend?"

"I wasn't a girlfriend until last night, so give Lauren a break," Aida offered.

"It gets better, Mom. This morning I was promoted to fiancée."

"What? Have you been smoking pot again, kid?" asked dad.

"Natural highs only, Pops."

"I think we need to do a video chat so we can see your girlfriend."

"Uh, Mom - we aren't dressed for company."

"Who cares? Come as you are."

"He means we aren't dressed. Period."

"Oh."

"Can you think of a better way to celebrate an engagement?"

"That's the honeymoon, son."

"Darn, I get those two mixed up."

"Like fiancé and fiancée?"

"Actually, those aren't mixed up. I need Dad's friend's help so I can get a believable set of breasts that will last a weekend."

"Shit!"

"I didn't know you knew that word, Mom."

"I changed your diapers, kid. I am all too familiar with your shit."

"But why can't you just be a normal, ordinary fiancé?"

"Because I need to be a fake woman with a fake knockers so I can be a fake fiancée to piss off her bitch of a mother."

"Where did we go wrong, Andre?" asked Mom. "His sisters turned out normal, they got married and had kids and didn't ask you for a fake penis."

"And a good thing, too. Boobs are easy, penises are hard."

"Dad, that's despicable!"

"I kind of like it, Mr Cooke," my traitorous fiancée replied.

So we explained why I needed boobs and my parents got a good laugh, as well as some reinforcement that their son was insane. Dad promised to get hold of his friend and ask for help and we promised to be at their house for dinner on Saturday.

I was breathing a sigh of relief when we hung up the phone until Aida looked at me and said "You do realize that this is going to take more than a quick change if we're going to pull it off. That means that my girlfriend will be spending the weekends with me until the party."

"No problem from my point of view."

"It also means my girlfriend will be escorting me to dinner at her parents' home next Saturday."

"Uh… problem?"

Rehearsal

Suddenly, what I had hoped would be a lazy day of hanging out with my new lover, interspersed with interludes of passion, became a concerted effort to tick off items on an ever-growing list.

The first item was to get dressed. Since we were not ready to perform an instant gender change, that meant I needed my laundry that was out in my car. That meant that Aida had to get dressed first and select my wardrobe since I had managed to split the seam in my shorts in my hurry to dispose of them last night.

Watching her get dressed was a fascinating experience, and if you think I was doing so to be able to know how to dress myself as a woman you are living in a fantasy world even richer than the one I was headed for.

Before I dressed, Aida measured various portions of my body. Not that she needed to know my inseam for my upcoming impersonation, but it was rather nice when she measured it anyway. When we had both progressed to the point where we could exit the apartment without being arrested for public lewdness, we headed for breakfast out. Too much to do to cook for ourselves that morning. Well, afternoon.

Aida proved to be no yogurt and granola muncher; IHOP's Big Steak Omelette, complete with a stack of pancakes, handily replaced all the calories we had expended. We partook of the Seasonal Fresh Fruit, so that made it healthy, right?

I'm afraid the next stop will be a disappoint for many of you who are reading this. The stop was at Target, the purchases were a couple of plain cotton bras, the things were about as sexy as the halter on a horse. Also a ten-pack of granny panties and some pantyhose. I was instructed to put on the pantyhose and then we found a pair of simple black flats to fit my clodhoppers. We might be able to trade clothes, but my feet would never fit in her shoes. I felt like Cinderella's ugly stepsister.

At the checkout I reached for my wallet, but Aida told me to put it away.

"Look, we're doing this as a command performance for my father and my bitch mother. No way I'm going to let you spend money like this on me. I have his credit card and his accountants won't even notice it if I spend less than a megabuck. If this test run proves successful we are going to go shopping with a vengeance. You are going to look like a million bucks.

Just what I've always wanted to be - a clothes horse. Filly?

Leaving the store with pantyhose under my trousers was an interesting experience, especially as we had neglected to perform the ritual leg shaving common in these stories in our rush to get going. Such are the woes of the novice crossdresser.

Now comes the embarrassing part. Yes, I had tried on my sister's bras. Yes, I had stuffed them with socks and such. Yes, they looked lumpy and stupid. Yes I had tried on her dresses. No, I hadn't gone any further. This had all been done in splendid isolation, well away form prying eyes.

Now I found myself the owner of two of my very own bras. The phrase teats on a bull was passing through my mind at regular intervals as we entered a veritable palace of feminine delights, where there were prying eyes aplenty. I was beginning to realize that the afterglow of my first successful sexual experience might have warped my judgement just a teensie bit.

Somehow, when Aida had been tossing the term prosthetics around when explaining her advice to women who wanted more, I had imagined some sort of medical supply house. You know, a place full of wheelchairs, hospital beds and urinals for both men and women.

I had been in such a place to rent a wheelchair when Dad had broken his leg some years ago. As a kid, I was fascinated by the illustrated labels on the female urinals - even if the woman was fully dressed when demonstrating the proper placement.

Shows you how far I was going to get by making assumptions.

Aida's confidence was present in full measure as she explained my needs. I swear the woman she was speaking to looked about fourteen years old and could have used a bit of enhancement herself. Sorry, I still think like a guy despite the direction my life was headed.

So the lady confirmed my bra size and my desired cup size. They spent a few minutes debating shapes and materials, and off the lady went to some undisclosed location. She returned with a pair of boxes, which she handed me. Aida and I retired to a changing room and she handed me my bra from her purse. I felt a bit smug when I adjusted the straps and donned it, snapping the hooks behind me like an old pro.

So I shaded the truth a bit when I said I wore my sister's bras a time or two.

The falsies dropped into place without ceremony and I found I had to have Aida adjust the straps a bit. The falsies were heaver than rolled up socks and needed shorter straps to keep them in place.

The room had one of those three sided mirrors so you could see your back. With my long hair, darned if I didn't look like a believable woman from the back. The unmistakable curve of my bra promised further delights on the other side of the body. Of course that was a politician's promise, void once elected.

Actually, it felt pretty good to have some heft in my bra, more like the real thing. Aida and the saleslady conferred and were less satisfied than I was. The forms were returned to their box and the lady again went in search of the proper item. She returned with a teardrop shape that did look more natural on my body. I could just see some miniature ski-jumper yodeling down the curve of my breast and launching himself from my pseudo-nipple for an Olympic record.

I kept that thought to myself.

Satisfied with my new bustline, the women left me to resume my normal identity. I dressed, restored the teardrops to their boxes and found Aida at the checkout with several bags already rung out, just replacing Daddy's much-used credit card in her wallet. I can only describe the look on her face as smug.

No crossdressing story would be complete without a trip to the mall, so that's where we went next. Not to visit Vicky or any of her friends, but to see the ubiquitous Claire. In a perfectly unemotional and straightforward transaction I left Clair with a pair of golden studs in my ears. Also a dozen or so little cards in a bag against the day the starters came out, You didn't think I could only choose one pair of earrings, did you?

One final stop to pick up the makings for dinner and I was amazed to see it was only three o'clock in the afternoon. It seemed like we had been running around the city for days!

I'd love to report taking a relaxing, feminine bubble bath to prepare for my role as a femme fatale fiancée, but such things are not possible in a studio apartment with only a shower stall in the bathroom. I had to content myself with smearing hair remover goop all over my legs and chest. While I was marinating I mused on those commercials touting the permanent removal of 'unsightly body hair' and the lengths they go to so as to not specify just where that unsightly hair was located. I supposed having a hairy cleavage would be one of those areas, thus the pink stuff slathered on my pecs.

The timer on my cell phone beeped and I washed away the goop, appraised myself in the mirror once I had removed the condensation, then attended to a few spots that I had missed. I emerged, towel wrapped around my chest just like I had seen women do in a hundred movies, to find a smiling Aida. She was attired only in bra, panties and gartered stockings. Now don't take this the wrong way, but she proceeded to give me a very thorough blow job.

You did take it the wrong, way, didn't you? Be honest.

I was blown dry with warm air from her blow-dryer and my hair was styled in a much more feminine manner. With that accomplished, she proceeded to thoroughly remove the moisture from my skin. I will admit her attentions to my crotch did have some results besides dry skin.

Thoroughly cleansed and dried, I learned how to put on gartered stockings without ruining them, something I had never tried before. I'm tempted to spend a few paragraphs describing the sensation of stockings on newly hairless legs, but better you should try it for yourself. It's worth the effort, believe me!

Next came the panties, which proved to be crotchless. That accounted for the conspiratorial grins at the checkout counter at the boutique. Before she could move away, I reached out and proved to myself that she was similarly attired. She slapped my hand and firmly told me "Not yet!"

Darn!

Then came the next step in my transformation from acquaintance to friend to girlfriend to fiancée. Aida deftly spread glue on the breast forms, waited until it was properly tacky and then carefully placed them on my chest. I had never really considered that most women had to go through life coping with a few pounds of pendulous flesh hanging off them. For a guy, it's quite an enlightening experience. Before the day was over I learned to appreciate a bra as a very useful item of clothing, not just something alluring for a man to remove prior to sex.

Actually, wearing a properly fitting bra turned out to be a lot more interesting than when I was sneaking my sister's bras from the laundry hamper. I didn't dare adjust them and we were not really the same size.

"So Lauren, the foundations have been laid. Pick out something to wear."

Ah, a test. I had several role models to choose from. Mom was a very good dresser, but she was of another generation. My sisters were my contemporaries, but I hadn't seen them dressed to impress in some time. They were both suburban housewives and their days of getting gussied up for a party were few and far between, and they most certainly didn't include me in such festivities. That left Aida, and right before me was a treasure trove of what she chose to make herself beautiful.

But wait, I had only seen her dressed down to do her laundry and we were certainly not going to dress in anything fancy to hang around her house. Having clothed herself, she was wearing slacks and a blouse opened just far enough to be interesting. That would never do - the slacks were cut for her generous figure and would be insufferably baggy on my beanpole body. Ditto the open buttons, no way I wanted to have the plastic boobs showing to any inquisitive male.

In previous generations the answer would have been simple: a housedress. However, my grandmother had proudly claimed to be holding the sledgehammer when her generation drove a stake through the heart of that 'women don't wear pants' bullshit.

Lacking any appreciable hips, I figured that a skirt and top would not be the best choice, so a dress it was. Scanning through Aida's closet I found a burgundy double-knit that might work. It had a high neckline, was elasticized just below the bust and had a full skirt which helped to hide the lack of hips. I pulled it out, gave it the once over and removed the hanger. I slipped it over my head and shimmied into it, getting a kick as the elastic snapped into place after it cleared my bustline.

I gave a little spin as I had seen my mother and sisters do and said "Do I pass inspection?"