A Familiar's Fate Ch. 02

Chapter 2

It was a restless night, and I woke from my sleep several times throughout the night. Fortunately, I was allowed to sleep in. When I awoke, I didn't know exactly what time it was, as there were no clocks upstairs, and I had left my phone downstairs. Yet I decided I should start by cleaning up.

I made my way to the bathroom just down the hall. A quick dash in my underwear, hoping she would not catch me. Fortune favoured me this time. I showered using the flower-scented body wash and shampoo. That was to be expected, so I never gave it much thought.

On this particular morning, I was thankful that I didn't really grow much facial hair since it allowed me to go a day or two without shaving. There was a pink razor on the ledge, so I subconsciously checked for body hair. Once again, there was no shaving required.

There appeared to be an unused hair brush, so I brushed my hair back straight. With its shoulder length, I typically either dropped it below my shirt collar, or spread it out with an unkempt look. Today, I decided to keep it in a clean straight back style.

Fortune favoured me once more as I dashed from the bathroom to the spare bedroom. At least this time, I had a towel wrapped around my waist.

And now was the moment I had to decide. For which, the anxiety had caused my restless night. What was I going to wear?

Perhaps I should shock the hell out of her by wearing a dress, makeup and heels. How would she react to me truly being feminine?

I decided that I really didn't want to know the answer. There was every possibility that she would love it. Would I love it? I dismissed that thought as well, not wanting to know the answer.

I started with something easy, finding a pair of ankle socks and sliding them on. Clearly ladies socks, but not overly so.

I then rummaged through the panty drawer. Lots of lace, lots of sheer fabric, lots of thongs, and lots of pink. My choice was not easy. At last I found a pair of plain white briefs. They were unmistakably feminine, but at least they weren't sexy.

I noticed the matching bra. Would she like me to wear that? No, I wasn't going to do that. The fantasy part of my brain led my hand along the delicate fabric, This would be so exciting. It was certainly exciting me at that moment. Too soon. I closed the drawer.

Next up were shirts. They were mostly pink t-shirts or camisoles, or shirts with a lace trim. I considered my options, and then shut the drawer.

Perhaps there was a dress shirt I could use. I shifted to the closet. Once again, lots of pink or lavender coloured shirts with lace trimmed collars.

This was certainly not Karen's style. Everything was delicate, soft and feminine. While her wardrobe certainly highlighted her beauty, the clothes she wore in the office exuded strength and class.

Eventually I found a white cotton blouse. It was clearly a woman's blouse based on its cut and style. Yet given the other options, it was the closest to a man's dress shirt. I then turned my attention to pants. If I could find any. There was mostly skirts in the closet.

Some athletic stretch pants would fit, but I definitely didn't want something skin tight. I didn't want fabric that shaped my ass and left a revealing lump in the front. Perhaps, I was worried that it would show only a small lump.

There was a pair of tight ladies jeans. I gave them some thought. They were tight and form fitting. Unmistakably ladies jeans. Yet they were still just jeans. It bothered me that I could fit into all these clothes. For most men it would be physically impossible to fit into these clothes. Yet for me, there was an undeniable fit. I simply had to choose what I could accept.

I chose none of the above. The pants I wore yesterday were still clean. I could wear them for another day. With this fateful decision behind me, I wandered downstairs.

* * *

As I wandered into the living room, I heard the back sliding-door open.

"Good morning sleepy head."

I heard her before I had turned my head. And what I saw left me tongue tied. She was walking into the house, still dripping wet from the outside pool. She wore a skimpy, 2-piece, black bikini which barely covered her. It was like one of those slow-motion scenes in the movies when the scantily clad woman walks in, and time seems to stand still. The water droplets made her skin shine.

She walked up to me, and I lowered my eyes reverently. I worried, hoped, she saw the arousal she provoked within me. There would have been a tent in my pants, if not for certain limitations.

She ran her hand along the sleeve of the blouse and smiled. Then looking down at my pants, she remarked. "I have the skirt that came with this blouse. Didn't you find it?"

The skirt. The skirt? Why would I wear a skirt? "Uhmm, I'm fine." I didn't know what else to say. My arousal heightened in direct contradiction with my thoughts.

"Are you sure? I think it would look much nicer." She was staring at me, trying to unnerve me. And she was having some success.

"No, I'm good." I mumbled, looking down to the floor, afraid to look her in the eyes. She really was trying to emasculate me.

"Okay, fine." She sounded disappointed, as she turned towards the stairs "I'm going to get dressed. Would you mind making me a coffee?" It was more of an order than a request. "You know how I like it, black, no sugar."

She paused for a moment. "There's some jasmine or camomile tea, or there is cranberry and orange juice. There's also some protein shakes if you would like. Help yourself."

She strolled off upstairs, giving me a gorgeous view of her backside in the thin bikini bottoms.

It left me to wonder, what should I have to drink. For some reason she didn't like the notion of me drinking coffee. Especially how she drank it, strong with no sweetener. I found what I needed in the kitchen, a premium dark roast blend, and made the coffee. Even from the aroma, I could tell it was a strong blend. I kind of resented the assumption that I would not like a dark roast or coffee in general. Yet truthfully, it was too strong for my taste.

I poured her cup, and selected a jasmine tea for myself. I didn't care what the perception was, I enjoyed its sweet fragrance.

I had just finished pouring when she returned. Karen was dressed casually in slacks and a t-shirt. Apparently she didn't find a skirt more comfortable. And I wondered why there were no black t-shirts in the room I used. Sure it was a ladies style, but it was a far cry from the pink and frilly options available to me.

There was no point in arguing over it. She tasted the coffee and smiled. "Excellent, thank you."

I could swear she was equally pleased by my choice of tea.

With our mugs in hand, we walked back to the living room. Karen sat back in her usual spot on the sofa. I then sat beside her and began booting up my laptop. She was staring at me, glaring.

I was stunned. Weren't we getting right back to the work? She glanced at the floor in front of her, and then back to me.

It then dawned on me, the reason for my silent reprimand. I wasn't in my place, on my knees, at her feet.

She watched me as I came to this realization. She was challenging me. Daring me to resist. I didn't. I slipped down onto my knees.

She petted my head like I was a dog. "Good boy, good boy..."

I was about to say something. To say how condescending she was being. To say that I was a man, about the same age as her, not a boy. Yet part of me loved it. Part of me stiffened despite my wish to be strong and direct. Before I could say anything, she had changed the subject.

"I like your hair like this. You should keep it straight like this regularly. Perhaps styled a bit."

I blushed. I had forgotten that I had brushed it back straight, showing its length at the back but behind the ears with an open neck. Very lady-like.

I really should cut my hair short. Of course, if I did, I would never hear the end of it from my lady friends like Joanne at work, and now apparently Karen as well. I smiled at her compliment.

My attention turned to my computer screen in a feigned attempt to be studious. I simply couldn't look her in the eyes without blushing. And from my position, on my knees, at her feet, I was continually on edge looking up to her.

* * *

We actually did get some work done over the next few hours. Like the previous evening I started to relax on my knees. Even on the occasions that I stood to retrieve something or grab a drink, I returned to my position at her feet.

It was disconcerting to have her leg brush against me on occasion. And when she leaned forward, she would come very close to me. Sometimes, her breasts would be touching my shoulders.

And there was no easy way to look at her. Looking up, I often found myself staring at those breasts pressing against her t-shirt, nipples clearly visible. If I did manage to stop myself from looking at her breasts, I was caught by those beautiful hazel eyes. And if I looked straight ahead, I was staring at her thighs. Or even worse, staring between her legs.

The only solution was to look forward at the computer. Even as she idly ran her fingers through my hair. 'Look forward'. Even as she playfully rested her feet on my thighs, or ran them along my side. 'Look forward.'

When I looked back with a questioning expression, silently asking if she was flirting with me, or teasing me? She simply gave this faux innocent smile. As if to say 'Yes, can I help you?'

We took a break around 1:00 for lunch. At her request, I made us some sandwiches and a salad. It was her home, but I took care of work in the kitchen.

Karen stood to the side observing me as we idly chatted. I liked being in the kitchen, and she was being so nice to me.

She ran her hand along the sleeve of my blouse. I mean her blouse, which I was wearing. Oh hell, I'd never seen her wear it, my blouse. I blushed and looked down. "I really like this on you. It fits you nicely."

I shifted nervously. The blouse did feel nice, but what did that say about me?

Her hand trailed downward. "But Chris, these pants don't fit you properly."

I didn't quite know what to say. I bought them off the shelf at Wal Mart. They weren't exactly designer pants or tailored. Yet there was nothing else for me to wear.

"Wouldn't you be more comfortable in a skirt?"

Oh crap, she's not talking about the skirt again. Yet involuntarily my penis stiffened in response.

"No, I'm fine." My calm response belying the turmoil I was in.

She was scrutinizing me. Did she see how aroused I was? I didn't see her look down. Was she looking for signs of arousal, for signs of a hard cock? If she did, there was no hard evidence. There was no revealing bulge. Was she debating how much she could push me?

Perhaps with a small penis that could barely show in my pants when fully erect, I should be wearing a skirt.

Karen shrugged. Now she was the one hiding her desire. She clearly wanted me in a skirt, emasculated.

I sighed with relief, or was that disappointment that she had not pushed me further. After our short break, we were back in our place in the living room, with me on my knees of course.

Over the course of the afternoon, it was difficult to find a comfortable position. My pants pulled against my knees and they chaffed along my thighs. As I shifted to find a more comfortable position, she took notice.

"You don't look comfortable in those pants. Are you sure you don't want a skirt?"

Immediately, my penis stiffened in response, which only made my pants more uncomfortable. I was flustered, and looked down. Perhaps I should say yes. A skirt would actually be more comfortable, physically at least. Yet I couldn't. I shook my head.

She continued to stare at me, sensing I was loosing my resolve. "Are you sure? There's a white skirt with pink hearts and a lace trim. That would look nice on you."

I looked up to her, stunned. That skirt was so feminine. Weren't all skirts? Men don't wear skirts. Yet my penis was as hard as a pencil, thinking about it. "No, I'll be fine."

She continued to stare at me, particularly my pants. I wasn't sure how much longer I could hold out against her disapproving frown. My Pavlovian response was craving her smile.

Karen stood up and started walking towards the kitchen. Pausing at the doorway. "Let's pack it up for the day Chris. I think we've done everything we needed to accomplish."

She then proceeded to the kitchen. We did already have our tasks laid out for Monday back at the office. Yet I feared another reason for her wrapping things up. I had resisted her, and now she had grown tired of me.

I knelt up, looking towards the kitchen. I wanted to cry out. 'Karen I'll be good. I'll wear the skirt. Just don't make me go.'

She sauntered back into the room, wine glass in hand. When she saw me kneeling up, staring at her, she chuckled. "Don't you look cute. Like a little puppy anxiously waiting for its mistress to return."

I blushed and looked down.

"Let's have some dinner. Shall we order in, or would you like to impress me with your culinary skills?"

I practically leapt to my feet. "I'll cook."

I actually am a good cook. I have spent countless hours, with mother's encouragement, learning from Alex. This was my opportunity to impress her. They say that the way to a man's heart is through his stomach. Hopefully, it was true for women as well, or at least this one woman.

Either way, we were having dinner together. And there was no rush to dismiss me as I had feared.

I set to work in the kitchen, and she stood to the side observing and chatting. It felt good to be in the kitchen. I asked about her favourite foods, spice preferences, any allergies, etc., and adjusted the dish accordingly.

I was pleased that she allowed me to set the dining table. It provided a sweet romantic setting.

And it was romantic, at least from my perspective, being able to stare into those beautiful eyes and make small talk over dinner.

She was suitably impressed with the meal. "Your place is definitely in the kitchen."

It was an odd compliment, particularly with the old patriarchal role assigned to women. Yet, I simply took the compliment and smiled.

After dinner we returned to the lounge. She sat down on the sofa, and looked down at me affectionately as I naturally returned to my knees. Only this time, I had changed my position and was now directly facing her. She petted my head as if I was a puppy, and smiled at me.

I smiled back, and looked down nervously at her feet. She leaned forward, stroking my hair. And then I felt the warm liquid along my crotch. At first, I worried that I had lost control. I had been extremely aroused and my penis was as hard as it ever could be.

But it wasn't me. She pulled back and spoke rather flatly, "Oh, I'm sorry. How clumsy of me."

I looked down and saw the dark stain over the crotch of my pants. A red wine stain. I looked at her in shock. She was sitting impassively staring at me. Her words were apologetic, but her tone and manner suggested this was deliberate.

"Let's go upstairs and get you cleaned up." She stood and offered me her hand. It was like a mother taking her child's hand, 'oh dear, you've had an accident'.

Despite, or perhaps because of her attempts to infanticide me, I took her hand and proceeded upstairs to the bathroom.

Karen dampened a cloth and then began to wipe the stained area. I immediately attempted to cover myself and reach for the cloth. "Karen, I'll do it."

She pulled the cloth back behind her. "No Chris, I'll do it. I made the mess."

Yes, but it is my crotch she was rubbing through the wet pants. That's what I wanted to say. What I should have said. My little member was throbbing with excitement.

"It's not coming out," she advised. "They'll have to be dry cleaned. I'll pay for it. Or better yet, I'll buy you a new pair. In the meantime, let's get you some clean clothes."

She then led me by the hand, not to her room, but to the pink room. Oh goddess no! I knew what was in this closet. Before I could say anything, she was reaching for the button of my pants. "Let's get these off."

I stood completely stunned as the pants were unzipped and pulled down. Standing with my pants around my ankles, and my erection now showing through the white, wine stained panties.

"Come on silly, step out of your pants." I remained speechless. Yet followed her instructions.

She now had her finger under the waistband of my panties. She was going to see how small I was. She was going to laugh.

Of course, I had fantasized about her stroking my cock. Yet now the reality set in. My fully erect penis could be held in her fingers.

"It's nice to see you wearing panties. Yet why did you choose such an ordinary pair? There's much more pretty ones in the drawer."

"Uhmm, I don't know." I had forgotten that I was wearing panties. My earlier embarrassment was now being far exceeded by what was about to happen.

She pulled down on the waistband with both hands, down past my hips, and allowed the panties to drop to the floor. I stepped out of them out of routine, my mind was frozen. She could now see me.

Karen reached out gently to touch my penis and I flinched. She looked at me and smiled, that wonderful smile, and I relented.

As I feared, she held my fully erect penis in her fingers. All 3 inches. And since I was hard, I couldn't lie and say it was just nerves or the cold.

"It's so cute," Words that no man wants to hear about his cock. Yet Goddess help me, I stiffened even more if that was possible.

She was gently holding my little penis in her fingers, causing me to tense up immediately. I tried controlling my breathing. Tried controlling my excitement. Yet she was staring at me with that addictive smile, and touching my penis.

"Uhmmm... Karen," I looked down at her hand.

She pulled her hand back. "I'm sorry." She laughed. "Not much control of your little friend is there?"

It was more of a statement than a question. I nodded, ashamed. Yet, also relieved that I had not ejaculated from the slightest touch of her fingers.

"I don't imagine it," she looked at my penis, "gets much attention... I mean besides you rubbing yourself."

My eyes were on the floor, my face was red with humiliation. Yet still my little penis was hard and twitching, aching for her hand to finish the job. I nodded in agreement.

"Poor little sissy."

My eyes darted up.

"Oohhh, touched a nerve, did I? " She chuckled. "The boy wearing a blouse and panties doesn't like being called a sissy."

I flinched as she said the word once more.

"The boy with the small penis, who ejaculates at the slightest touch doesn't like being called a sissy."

I was looking down with shame, but glancing up into her eyes. Begging for a reprieve.

A prayer unanswered. "The pretty boy with smooth skin, long hair, and a thin figure which many women would love to have. That boy doesn't like to be called a sissy "

My penis twitched. She called me pretty. A pretty sissy. While my mind was screaming 'No, no!', my little penis and my flushed skin was saying 'Yes, yes!'. My mouth said nothing.

Karen was staring at me with an amused grin, clearly sensing my conflicted emotions.

Reaching into the drawer, she pulled out a pair of pink satin panties. "These are much prettier than those Plain Janes you were wearing." She handed them to me.

There was no denying they were pretty. I stood motionless, looking at the smooth pink fabric in my hand. They were pretty, and I would look pretty wearing them. Not what a man wants. But a sissy? My little penis twitched with excitement.

I now only had two choices. Continue to stand before her, naked and exposed. Or, l could wear the pink panties.

I slowly stepped into them and pulled them up. My erection wouldn't go down. Yet even in this state, it fit nicely in the panties. The satin pressed against my penis excited me even more.

"Very pretty. Pretty in pink," she remarked with a smile.

I blushed. Was it a blush from humiliation, or was I happy to please her?

She walked over to the closet, and I followed. She flipped through a few items, and then pulled out a blue-striped skirt.

"I thought you wanted the skirt with pink hearts?" Why did I say that?? I was now in a panic.

She had selected something professional looking. Still a skirt, but something modest. Now I had effectively requested the most girly option available.

I was surprised by how excited she was. She hugged me. "Yes, you're absolutely right! That one is much prettier it's shorter as well."

I wanted to argue that it wasn't my idea to wear the skirt. Yet the point now seemed to be moot. And I was too happy now, in her embrace, to make any complaint. She rummaged through the closet until she found it. And it was just as bad as I imagined. Yet my fight was over. I put on the skirt without complaint.

There I was fully emasculated. Standing in the pink room which was my room last night. Every item of clothing I was wearing was meant for a woman, even the ankle socks. It was impossible to see oneself as a man when I so easily fit into a blouse, panties and a skirt.

She smiled, clearly pleased to see me in the skirt. I had tested her will all day, and now she had finally won. I was her submissive sissy in pink.