Contractual Obligation Ch. 02

Chapter 2: Education & Understanding

The lawyer made certain I understood what I was signing before he allowed me to call it final. My new residence was the manor and I was shown up to a room right away. The older man who escorted me explained that I would be roused early in the morning and that I should plan for a long day. He left me with a pitcher of water and everything I needed to clean up before bed.

I was already feeling strange but when I heard the door lock behind him, I started to get really nervous. Typical thoughts came into my head. What the hell did I get myself into? Was I insane? What if this was all a ruse? Why would I take all this on faith? Even exhausted, I couldn't settle down and I didn't fall asleep until nearly two in the morning.

Even then my dreams were out of control so it wasn't restful. When I was awakened to the door unlocking, I nearly fell out of the bed but my eyes ached with exhaustion.

"Miss Dupont is here to begin." It was the old guy from the night before. "I suggest you put on your clothes and make your way downstairs immediately."

"But...shouldn't I get cleaned up first?"

"I did say 'immediately'...did I not?"

"Fine, fine...I'm on my way."

I threw on the clothes I wore from the night before and rushed out the door, fighting to remember exactly how I got up to the second floor in the first place. I had been in quite the daze when I finished with the contract so I wasn't paying that close of attention. When the door had closed, I couldn't think of anything but what I was doing. The manor was a mystery to me which made it all the more creepy.

The hallway was long but I found my way and entered the foyer. That much I remembered. I recognized the room where I had met the benefactor and signed the contract and decided to try the opposite door. It was also ajar and sitting down on a cushy leather armchair was a stunning woman dressed to the nines.

Her short black hair was slicked back and pressed tightly to her head. Wide eye brows knitted over blue eyes that seemed to shimmer even from across the room. She was pale, wearing quite a bit of makeup which made her all the more severe. A black blouse was unbuttoned to just below her breasts, revealing a lacy black bra beneath and her skirt waistline was high, the hem stopping just above her black stocking clad knees. The heels were at least six inches and they buckled around her trim ankles.

A cigarette casually hung between her fingers, blood red nails filed to points.

"Good morning, Cecile." When she said my new name, I felt a thrill dance in my stomach. I could barely swallow let alone reply so I just waved. "Are you shy?"

"Not really...just tired," I replied meekly. "I'm afraid that last night was quite a lot to take in. I didn't sleep very well."

"Trust me, after today, you'll sleep like the dead." She tapped the ashes in a tray nearby and crossed her legs. "I suppose that I should tell you that your belongings have all been moved to storage and your landlord knows that you won't be coming back. We've paid off this month's rent and terminated your contract. Also, all of your bills have been taken care of as well. Your cell phone has been terminated. As of six thirty this morning, your old life gave way to the new. Congratulations."

"Thank you." I trembled despite myself. This was what I wanted but it didn't make it easy to take. I couldn't believe that I was committed. I was getting everything and all I had to do was accept it. Hell, they were making it easy. I won the lottery... I just had to let that sink in.

"You're welcome," she replied. "Please, sit down. I'm going to give you an overview of what you can expect over the next couple of days. I know that you've gone through the psychological evaluation process but all that means is that we've proven that you're not supposed to be a man. You've still lived as one for the last twenty-five years. That means that we have a lot of work to undo, a lot of habits to break and more importantly, a lot of things to learn that no one learns naturally. Do you understand?"

"Like...what do I have to learn? You make it sound really complicated."

"Darling, gender roles aren't about the bits you've got between your legs. Those don't define you. Even that feeling in your soul that you're not meant to have a penis doesn't make you a man or a woman. Not in the social context. I'm talking about basics. How to move, how to look, how to walk and talk, how to carry yourself and how to not only mimic those things but to embrace them as you.

"Take right now for instance. You're slouching with your legs parted, your feet resting on their heels. Do you think that's attractive? Or ladylike? Imagine sitting like that in heels and a skirt, showing the world your panties. I want that thought to generate shame in you. I want that to be wrong in your mind so that you don't even think twice about keeping yourself proper. This is what I'm going to teach you and trust me, there's a lot to learn.

"You'll have so much to practice, you won't have time to think of anything else. The regimen that I have designed for you will make it so you think like a woman, not just feel like you should be one. There's a tremendous difference."

"So...I mean...does that mean...I guess I'm trying to ask, does this mean that I won't be... I mean...I won't be me anymore?"

"You can't be you anymore. You need to let that person inside you that you've been forced to suppress out. She's a terrified woman who would love to walk freely in the world but right now, she's hampered by a defense she had to create in order to function at all. That defense is what you're referring to as 'you'. Once we break that down and teach that poor hostage girl what it means to be a lady, then you'll finally feel right for the first time in your life.

"But to answer your question more directly, no you won't be that guy who's name I won't even say. Unless you lied to your therapist and made up stories to get him to give you a clear bill to pursue becoming a woman...unless you want to do this for some fetish or other and want to pretend...then you're in the wrong place and I would like to terminate the contract immediately."

"No! It's not that at all!" I put my hand out. "I'm just...please, be patient with me. This is happening really fast."

"I don't think that you can wait much longer to embrace who you want to be." She stood up and stubbed out her cigarette. "I think it's time to get started. First thing's first, we have your measurements from your doctor visit and we bought you a training wardrobe. Later, one of your lessons will be how to pick your own clothes but for now, you will dress like a woman every day...more so even."

"What's that mean?"

"I mean that women don't dress in skirts and stockings every day with heels. They wear jeans or sweats or capris...they wear sweaters and tee shirts. You will be wearing skirts, stockings, heels and blouses every day until you can buy your own clothes. The key is to learn how to live in that sort of thing, to embrace that aspect of yourself in a dramatic way. It'll be shellshock but it's going to be like diving into the deep side of the pool. That and it will help you learn to walk properly."

"When do we start?"

"The first thing that I want to do is take care of some hygiene issues. Let's start by getting that outfit off."

"What...now? Here?"

"Cecile," again she used my name and again, it gave me a thrill even with the severe tone in her voice. "There's something you should know right now. I don't tolerate being questioned. If you have a legitimate question, such as you don't understand an instruction I've given you, then you're free to speak but otherwise, I expect compliance. Now, telling you to strip can't have been so challenging that you needed to question it but you're new to all this and it is a lot...I'll give you a pass today. But tomorrow, you won't question me. Understand?"

"Yes, ma'am."

"That's even better. Show some respect." She turned away. "What the hell are you waiting for? Get those clothes off now!"

I fumbled to my feet and kicked off my shoes while stripping off my shirt. There was a cool breeze that tickled my flesh and as I dropped my pants, I was instantly chilly. I couldn't tell if I was trembling because of the cold or because of fear but exposed and completely naked in that wide open room, I never felt so vulnerable in my life.

Until she started to admire me. Then I felt more vulnerable...and scrutinized in a way that I didn't think was possible.

"Okay, there's some good news here," she said, stepping around me. "Not a lot of body hair, you're blessed in that regard. It'll all have to come off of course and you'll need to keep on that until you can go in for a procedure to keep it away. I think waxing for the first time...at least with the upper body. Shaving for the lower body. Today, you'll learn how."

She continued around me in a circle and stopped in front of me, bending her knees. She was directly in front of me, her face mere inches from my cock. I bit my lip and stared up at the ceiling, unwilling to watch her appraising me. There was something beyond humiliating about it and I couldn't understand why. One thing was certain, I'd be thinking about it later.

"This is also fantastic news. First, you don't appear to be attracted to women and if you are, then you're even smaller than I think. But secondly, your penis is unusually small and your testicles will be simple to tuck. You'll be a passing woman for quite some time before you have to have these removed but really, this is little more than an engorged clit. That's good news for lines."

Whatever was left of my masculine side shriveled up. I never really felt like I had much male pride but as she criticized what I lacked in manhood, I realized that there was some semblance of it lurking just beneath the surface. My cheeks burned with shame and as she stood back up she took note and grinned.

"A ha, so there is something to break out of you. And here I thought I was getting the easiest payday of my life." She took my chin between her thumb and forefinger and forced me to look her in the eyes. "Have no fear, we'll overcome that particular foible together. That shame you feel right now will be twice as bad when you think back on your previous life and it'll burn you to the core when you think of your penis dangling there or the fact that you have one at all. If someone calls it a penis, you'll want to cry. Before long, it'll be your clitty and any other designation will just seem wrong."

Was this what I wanted? In a way, I felt like it was necessary. I mean, hopping out and getting some surgery didn't ensure that a person would be a woman. I could get my hair removed on my own, have some breast implants and hit the mall for some women's clothes but in the end, I'd just be crossdressing. I wouldn't have the tools I needed to truly BE a woman. If a little humiliation was going to help me get there, then by God I'd take it.

"I...understand. It's just going to be a little difficult to get over the initial shock of changing, as you said, twenty-five years of habit."

"I'll be patient...to a point." She snapped her fingers and tossed me a short, pink robe. "But enough of that, there are a couple of other things that you need to do. Put that on and come over to the table. Your new physician has prescribed a few things. He'll be checking up on you every couple of days but for now, let's go over what you do every day and night."

The robe barely covered my ass and roped off just above my waist. It was a frilly pink affair with long sleeves and a low cut front. I crossed it over as far as I could, mostly because I was cold rather than any feeling of modesty. Miss Dupont had already seen everything, there was no use hiding it from her now. Maybe that was the real point of the inspection: to break down the barrier of modesty.

"So, your breakfast is simple fruits and some cereal. Your diet will be carefully monitored. The doctor has created a balanced meal schedule for you. The medical side of your transformation is very complicated and you'll be taking hormones, honestly, for the rest of your life but just think of them as birth control pills. It might make it easier in the long run.

"Later, you'll be given injections too. We're easing you into this. Combine these with the other processes and you'll look as much like Cecile as you feel. For now though, eat up. When you're done, you'll get that nasty hair off your body, throw you in some heels and get you walking around this place. I want you to have something to practice by lunch time."

Breakfast was just as she said: a healthy cereal, some fruit and cranberry juice that I barely choked down. The hormone pills were massive and even holding them in my hand made me nervous. This was truly the point of no return. When I started to take those, then I'd be down the rabbit hole. Sure, one could quit but that commitment, that step...I mean, what could be more empowering than knowing that I was going where I wanted? That I had made a chemical as well as spiritual commitment to make it happen?

I finished my meal, brushed my teeth and was led by Miss Dupont into a bathroom that looked more like a spa. There was a massage table, a walk in shower, a sauna and a massive bathtub that could easily fit four people. She took my robe off for me and gestured to the shower. "Get very clean. I'm going to help you this first time with your hair but I want you to pay attention to how we shave your legs. You'll be responsible for that from now on...and for the love of God, be thankful that you have light colored hair. Brunettes the world over would kill for fair hair on their legs."

The hot water felt fantastic considering how cold I was and being clean was a rapture unto itself. I used the soap she had prepared for me, a berry scented stuff that was over the top feminine. I had never smelt so sweet in my life and when I got out of the shower, my skin was soft as silk. Miss Dupont ran her hands over my body appreciatively, nodding with approval. I felt my groin tighten when she ran her finger over my scrotum and across my penis.

"We'll milk you ever five days for a while," she said. "It won't exactly be an orgasm...but we'll keep these nice and empty until such time that you don't have to worry about that anymore. You know, before we start with shaving you, there's one more thing that I want you to become familiar with. I'm afraid we're going to have to give you an enema and keep them up too. Have you ever had one before?"

I shook my head 'no'.

"They're as unpleasant as you would imagine but they make anal sex considerably better. Anyway, let's do it over here. Throw some towels down and kneel on them, I'll mix a solution."

It felt so clinical, I was back to trembling and as I dropped to my knees on the towels, I felt shame hitting me again. I couldn't tell why though. Was it because I was likely filthy and needed this treatment to clean me out? Was it because I was being treated like a project and not a person? I couldn't tell...it was another thing to file away for a quiet time when I was alone. Not that it sounded like a healthy thought process.

Miss Dupont brought a low foot stool over and set it in front of me. "Rest on your chest, I'll need access to your stomach." I complied, wincing at how cold the metal was. "Sorry about that. Don't worry, the next part will make that discomfort seem like a picnic."

At least there wasn't excitement in her voice. I could at least trust that she wasn't a sadist enjoying my suffering. This was just something that had to be done. There was some clattering behind me, a plastic bin placed down between my ankles (which she urged apart, exposing me). She separated my ass cheeks with one hand and a gloved finger began prodding my hole with lubricant. The goo was cool and I had to concentrate very hard not to tighten my muscles and deny it access.

She worked it around slowly, pressing in and out as she worked down my resistance. Each time she pulled out, I felt empty and each time she came back, another wad of lubricant was massaged into my skin. I lost track of time but it seemed to go on forever before the plastic tip pressed gently into my ass, and though I have no idea how deep it went, it seemed like she was digging for China.

Slowly, I felt a little pressure begin to build as the solution was introduced to the tube. Miss Dupont kept it going at a subdued pace, letting my body have time to acclimate. The water was lukewarm and a total shock to my system. I tensed up but she soothed me into relaxing, petting my back like a prized hound. I had to take long, deep breaths to stay calm. Administering the solution took fifteen minutes.

At that point, Miss Dupont massaged my abdomen, moving up and down my sides nearly to my chest. Each time I felt like I couldn't hold it anymore, she had me take deep breaths and forced me to relax. It was uncomfortable but not painful, I would never look forward to such a sensation but there was nothing really wrong with it.

The worst part was just how taboo it felt to have this woman who was not a doctor administering such a personal thing. Maybe she didn't think of it that way but in my mind, there was an intimacy when sliding something into someone's ass. She performed the service with all the decorum of a physician, all the impersonal touch of a professional caregiver. For me, it was something else...it was a symbolic cleansing as well as physical.

Another fifteen minutes passed and I swore it was a miracle that I was able to hold it that long. She helped me to the toilet but wouldn't let me sit. I had to crouch over it so that the muscles in my abdomen would push more, getting even more out. The relief to let that solution out of my body was a rapture that I had never known but when it was all gone, and it took some time to pass, I felt hollow and vacant.

I never wanted to use the bathroom again. Especially if it meant I might need another enema.

"Very good." She patted my shoulder. "Let's get you cleaned up again and we'll go to work on that body hair."

We shaved it all. She had me apply a women's shaving cream to my arms and chest first. The little patch of hair between my nipples was gone in three strokes of the blade. My arms were a little more cumbersome. She went with the grain the first time then relathered me for another pass back against the grain. She was patient and methodical and careful enough that I didn't bleed at all.

When she finished, she washed me off with the hand sprayer. I ran my fingers over my arm, now more pale without hair and felt more girly than I thought I had the right to. I was so smooth, without that hair, so much more feminine...I couldn't wait for the next steps which were considerably more intimate.

We started with my legs, working up from the feet. I only had a few strands on top of my foot but my lower legs were outright furry. She once again took her time relathering before each swipe. "You won't have to go through this ever again because you're going to keep it up," she said. "So don't ever let it go. It'll be a real pain to catch back up."

She had me spread my legs and got everywhere, all of my intimate parts. My scrotum was shaved bare, inside my thighs, my abdomen so that I had no more pubic hair, all of it gone. She sprayed me down when we were done and showed me a mirror. All we did was take care of the hair on my body and I looked like a new person.

I applied a lotion all over, a moistener that would offset the shaving. This was one of many products that she explained to me. The others were cleaning supplies for my face, my hair, my hands, my arms, my body...she explained exfoliation to me and when I should use a luffa and when a soft rag would due. I was introduced to plucking my eyebrows and how to take care of my cuticles.