A Familiar's Fate Ch. 06

Chapter 6

I slept contentedly wearing my babydoll nightie, on the bed with pink covers, in the room with pink floral-designed wallpaper. However, when I woke up, reality set in. All my clothes had been destroyed. I had nothing I could wear to work.

I knew from experience that there was nothing in this room's closet, so I grabbed a pink satin robe and went in search of Karen. I heard something from downstairs, so I wandered down and found her in the kitchen. She had showered, but was only wearing a long t-shirt and her robe. Simply enjoying her morning coffee before getting ready.

"Good morning Christine," she said casually, as if it was perfectly normal for a man wearing a nightie and a pink robe to be in her kitchen.

"Oh, uhm, good morning." It was hard to match her relaxed demeanor with my anxiety.

"Would you like some tea?"

I had completely moved beyond her expectation that coffee was too strong for me. I was on edge, and in no mood for a soothing tea. "I don't have any clothes to wear."

She sipped her coffee, and then looked at me. "What do you mean? I told you before that you can help yourself to whatever you want."

"Yes, but they are all dresses, skirts, blouses. They're all women's clothing."

"Yes, well, we've talked about this. That's what fits you better."

I was stunned. It's hard to make a claim to be masculine wearing nothing but a nightie and a pink satin robe. Yet here I was, desperate to maintain some semblance of masculinity in public, at work. I started to cry.

Yeah, I know, a really effective way to show how manly you are.

Karen set her coffee down and hugged me.

"I really like being with you," I blubbered between the tears. "And I have to admit I do like wearing pretty clothes when I am with you."

I wiped the tears from my eyes. "But I can't do it. Work was my one refuge. Now I'll look foolish. A freak in a dress. I know my job isn't much. Yet it was the one place I could feel somewhat in control, a man taking care of himself."

This probably didn't make sense to her. I'm not sure it did to me. Yet I was brought up believing I needed to depend on someone else. Believing I could never be independent. Doubting my masculinity. And the fact that I was still a virgin, working as a junior clerk who was just scraping by, did not strengthen my self-confidence. Yet wearing a dress would cement those feelings, both for myself and how people perceived me.

Karen looked at me and kissed my forehead. Her embrace still holding me steady.

"Go take your shower. I'll find something for you."

I looked at her, uncertain of whether she was playing me. Yet I wanted to trust her, and still wanted to please her, no matter what. I nodded.

* * *

When I entered my bedroom after my shower, Karen was sitting on the bed with some clothes beside her. I noted with some relief that there was a pair of pants and a shirt.

Karen was now dressed in a sharp looking black pant suit with a white blouse. Once again she took my breath away. The epitome of feminine power.

Standing naked, except for the towel, I was getting nervous. Of course, she had seen me naked before, and knew my penis was small. Yet it was never comforting to remind her of my inadequacy. To make matters worse, my nerves made my penis shrink, compounding the embarrassment.

Noting my reluctance, Karen took control. "Drop the towel."

I dropped it, and stood nervously before her, awaiting her chuckle, or derisive 'It's so cute'. None of that came.

"We don't have all day. Put on your panties."

I was so startled by her direct tone that I immediately found a pair in the drawer and put them on, not thinking about the undergarment I would be wearing at work.

She then handed me a pair of nylons. Once more, I didn't question her. Yet I was beginning to wonder if the option of male clothing was just an illusion. She hadn't actually said she had men's clothes for me to wear, or that they would even fit me.

Once more, the hose kept my little penis quite snug, so there was no bulge at all.

Karen stared at me for a moment, running her hand along my thighs. With the nylons, my skin tingled with the slightest touch. "Are you sure you won't wear a skirt? I have a long black one, very professional."

I shook my head profusely. "No, I can't." I was almost ready to burst into tears once more.

"Very well. But remember, whenever you are here, in my home, I insist that you wear a skirt, or a dress. No pants. Understood?"

I nodded. "Yes."

She stared into my eyes. "Remember your promise. I will be very upset if you forget."

I nodded again, nervously looking down as her gaze was upon me.

She handed me the slacks, which I immediately put on. Only once they were fully on did I pause to look down at the pants. The style, the material, everything indicated these were a woman's slacks.

"But, but... these are for women."

"Yes, I told you I don't have any men's clothing here. And these fit you nicely. Perfect size."

It was disturbing and pleasant how the ladies clothing fit me perfectly. Usually I had to struggle to find the right sizes when I was shopping for clothes. Yet all these women's clothes fit me instantly. And the fabric brushing against the nylons felt amazing. My penis would have been erect if it was not being tightly held.

Karen next handed me a white camisole. I looked at it and gave her a bemused look at her, and then back to the camisole.

"I don't have any undershirts, but this will be fine."

Yeah, sure that makes sense. Wait a minute, none of this makes sense. I put on the camisole.

I reluctantly took the dress shirt which Karen now handed to me, and put it on. It was a cream coloured, satin shirt. Professional, but clearly meant for a woman. I ran my hand along my arms, and the fabric made me skin shiver with excitement. How did women wear all these clothes on a daily basis? I was so aroused by the feel of them that I could barely concentrate, and this was simply a pretty shirt and slacks set.

"What about some makeup? And I wish we had time to do your nails."

I vigorously shook my head. "No." I couldn't believe I had come this far.

Karen simply nodded. She had already assumed that I would not allow makeup, much as she may have wanted to apply a touch of blush and lipstick.

Karen walked over to the closet, and returned with a black pair of flats.

"Karen, I do have my shoes downstairs."

She looked at me, clearly having forgotten the one item of clothing which had not been destroyed. Something she would have to rectify. "No, these will match your pants a little more. And the fit is nice. They are a simple black pair, no bling, no heels. You should be fine in these."

Reluctantly, I stepped into them. The soft leather wrapping around my nylon covered foot felt wonderful. And like she said, there was no heel, so they shouldn't stand out too much.

Karen smiled. "OK, brush your hair, and let's go."

Upon her insistence, my hair was brushed back straight so it hung neatly at my shoulders. It still needed a cut but with the perm on Sunday, it was soft. I loved the way strands of hair brushed along the back of my neck.

And with that final touch we were out the door, driving to work. The smiles I received from Karen were intoxicating, and I was enjoying the way this fabric felt. I did kind of miss my delicate dress, but I was nervous enough as it was. Nerves which intensified as we pulled into the company parking lot, making me reluctant to get out. It was only one of Karen's dreaded stares of disappointment that dragged me out of my seat.

I walked slightly behind her into the office, hoping to go unnoticed. At any moment, I expected someone to laugh at me. No one said anything. And I could have made it to my desk and sat down away from scrutinizing eyes. However, Karen picked just this moment to ask Mrs. Simmons for a particular report.

I shifted nervously in my manager's doorway while the ladies spoke. I was expecting a reprimand for wearing something inappropriate. There was nothing revealing, but still.

For some reason I have always been nervous around Mrs. Simmons. Sure, she was my boss, but she was never mean or demeaning, and I had never been reprimanded. She was a good boss, but I was always on edge around her at the best of times. And now, I wanted to be hiding under a desk, rather than be standing before her.

As they were wrapping up, Mrs. Simmons smiled at me. "That's a nice blouse Chris. The colour suits you."

I blushed, and mumbled, "Thank you."

The ladies exchanged a knowing glance to one another and nodded. And then we were off, and I was finally allowed to sit at my desk. The pretty secretary sitting outside Karen's office.

* * *

Work did perform its magic. Over the course of the morning, I forgot about what I was wearing, and just lost myself in data queries.

A little after noon, Joanne approached me. The ladies were going out for lunch, and she asked me to join them. It was a nice routine, but I had been out of the circle since starting work with Karen and changing desks.

Karen was off site with a client, so I accepted.

It wasn't until I stood up that I thought about my clothing. The motion of my pants brushing against the nylon stockings below brought me back to reality.

I paused for a moment, thinking I should decline Joanne's invitation. Were they going to tease me?

Joanne said nothing, though she clearly noted the ladies-style of pants. She simply waited. Her light hearted smile helping to assure me.

These were my friends. The ladies who had come to my defense when guys were harassing me. They had always accepted me. So with that thought, I joined Joanne, and walked over to the restaurant.

To my relief, she didn't say anything about my clothing.

It was Lisa who remarked, as we sat down at the table, "I like your top Chris. Where did you get it?"

I blushed profusely, thinking she was making fun of me. She wasn't. Ladies notice clothing, and will compliment another woman. That's all this was, a compliment.

"Oh, uhm, it was a gift," I stuttered.

That answer made things worse. "Oooh, Chris is getting gifts from his lover. Who is he? Do we know him?"

I was beet red, and shook my head nervously. "No, no, no guy. It was from Karen."

"Karen?" Lisa responded uncertainly. The other ladies also seemed rather skeptical.

Fortunately Joanne came to my rescue. "Chris has been spending a lot of time with her. More than just work."

Cheryl piped in. "Sleeping with one of the executives in Account Management. Better watch out Joanne. Looks like you have some competition."

Joanne wagged her finger at Cheryl and laughed. Her reputation for sleeping with guys from the office was well known. For my part, I was just relieved that the attention was off me.

Perhaps too little attention as the waiter came to the table. "What can I get for you ladies?"

No exception. Even as he took my order, there was no correction. Did I really appear so feminine that I was passable without makeup, and a flat chest? My insistence on wearing a shirt and pants now seemed pointless.

Over the course of lunch, I did have to elaborate further on my new relationship. When did Karen and I become an item? I was prompted to reveal that I had spent the weekend at Karen's home. This was after all some juicy office gossip. Yet they were all happy for me, even if they were skeptical.

Cheryl summed up the general consensus. "We're happy for you Chris. You two look good together. I just worry that you're pretending, afraid to come out. But you don't need to. We accept you, no matter what."

The others nodded in agreement. I didn't know what to say. They were being kind, but still thought that I was gay and afraid to come out of the closet.

Joanne broke the uneasy silence by pointing to my ears. "What happened to your earrings?" And then for our friends benefit, added, "Chris had a lovely pair of ruby earrings yesterday."

"Amethyst," I muttered.

Joanne looked at me, not hearing me. "What?"

"They were amethyst," I stated more clearly. Most guys wouldn't know the difference, much less wear them.

"Oh, that's too bad. I think you would look pretty with earrings." Lisa said with nods of agreement from the others.

Alas, I was saved by the bell, or in this case the bill. Lunch was over, and we headed back to the office.

* * *

Back at the office, things were good between Karen and I. Gone was the frosty air of silence and glaring stares from yesterday. Now there was the gentle touch to my arm, which sent shivers down my body, and the warm smiles.

She even remarked, "Did you have a nice lunch with the ladies?" Clearly, there was no hint of jealousy. I was simply one of the girls.

This was an office, so a certain level of decorum was required. Yet I got the distinct impression, she was undressing me with her eyes. I was not accustomed to a woman looking at me, finding me attractive. It was a lovely feeling, but also scary.

Towards the end of the day, I was standing in her office, notepad in hand. Initially we covered off some work items. Then she noted that she had a dinner appointment.

She actually sounded disappointed. There was that lustful glance again.

I looked down demurely, blushing. Acutely aware of the women's clothing I was wearing. My penis twitched within the constraints of my panties

"I do have something for you."

I raised my eyes to look at her.

"I don't want a repeat of yesterday's clothing mishap. However, I did like the earrings. So, I noticed you left them behind this morning."

Karen put her hand out with the earrings in her palm.

"Oh, uhm, thank you." I picked them up and stared at them for a moment.

"I'm sorry I didn't give them to you earlier. I'm sure the ladies would have liked to see you wearing them."

I sheepishly looked to the ground. "Yeah, Joanne did say they were pretty."

"Well, what are you waiting for? Put them on."

I hesitated for a moment, but then relented and put them on.

"Very cute." She smiled and then kissed my cheek.

I blushed and looked to the floor, avoiding her gaze.

"I really think you should be more relaxed and happy dressed like this." She pointed to my satin cream-coloured shirt, cotton slacks, and now the earrings. She could see that I wasn't really accepting this. "Didn't your friends, the ladies at lunch, like your outfit."

I nodded, almost uncomfortable with how much they encouraged me to continue dressing effeminately.

"Well, I really think you should learn to relax. To be more at peace with yourself."

Unfortunately, our brief pause from the workday ended. Yet not without that animalistic look from Karen which said she was ready to devour me. She leaned forward and kissed me, taking my breath away. Then she calmly walked back behind her desk and sat down. "Goodnight sweetie."

For the moment I got what I hoped for. Karen kissed me.

Before I could exit her office, the strict mistress suddenly returned. "And don't forget the rules. I expect you to be wearing one of the outfits I gave you tomorrow. And I also don't want you to be playing with yourself when I'm not around. Your little penis belongs to me."

I looked to the ground and nodded. Terrified and aroused. In love? All I could think was, she kissed me.