A Familiar's Fate Ch. 08

I was more relaxed when I arrived at work the next day wearing a white, silky cotton shirt, black skinny-fit pants, hose socks, the earrings, and a pair of flats.

Karen wasn't around, but she had been there earlier. On my desk was a note.

Dear Chris,

I hope you behaved yourself last night, and I trust you are dressed appropriately.

I'm out of the office until this afternoon. Looking forward to seeing what pretty

outfit my sweetie chose today.

Love,

Karen

I felt a tingle of excitement. She was eager to see me. She said "Love". Maybe that's just an expression that people say, but still. She said love. I only hoped that she liked my outfit.

The morning was largely routine, and I buried myself in the project. Only pausing every once and awhile as the fabric of my shirt caressed my skin, or the panties rubbed along my little penis.

Once again, I joined the ladies for lunch. And while I had always been welcome, I was really beginning to feel that I was one of them. They complimented me on my outfit again. It was unusual to get positive attention from women. Truthfully, it was somewhat unnerving. Yet I now knew that they were being genuine, and not teasing me.

Not surprisingly, the only negativity that day came from the guys. I hadn't given them much thought. I had been preoccupied with pleasing Karen, and having the approval of Mrs. Simmons, Joanne and the other ladies. Yet the guys, who had always treated me like a wimp, found my new attire quite amusing.

It started with a meeting request with Marcus, who was the Product Manager for one line we were marketing to a major client. Karen wanted to meet with him to review the specifications, and if the product could be modified to our client's needs.

The moment I was standing in the doorway of his office, I regretted it. I should have called him, or emailed him, except he likely wouldn't respond for a day or more.

Why did Karen ask me to make the appointment?

"Well, aren't you quite the cute secretary. If I didn't know better, I'd be hitting on you," he said sarcastically.

Marcus was known to be a womanizer. I recalled Joanne speaking in glowing terms of her long lunch at a nearby hotel. He was someone with a large package, as she referred to it, and he really knew how to fuck a woman.

Standing before him now, I didn't know how to react. I was red-faced with embarrassment. I had no desire to be one of his conquests, not that it was an option. And now standing before him, and being judged by this alpha male, it was humiliating how inadequate I was as a man.

I could understand the animal magnetism that swept women off their feet. Precisely the opposite of the soft and meek energy I evoked.

I tried to avoid the nerves by focusing on the task at hand. "Yes, well, uhm, Karen has some questions about the Enterprise MPL for the Harrington account. She would like to sit down with you to get some background. We will need some modifications."

Normally they hate any suggestion of customization. "Karen wants to meet with me, does she? I'm sure she does."

It was clear what he wanted the meeting to be about. Smug bastard, he thinks he has a chance with any woman. Problem was, he did with most women. He was tall, handsome with an athletic build, educated, and well off. What was there for the ladies to dislike? Yet for me, he was an arrogant prick who made me feel inferior.

"Yes, the Enterprise MPL doesn't have everything we need." I shied away from the subtext he was suggesting, and attempted to deflate him through his product.

To no avail. He chuckled at my weak attempt at dignity. "Ok, let's see, when can I meet with Karen." He opened up his phone calendar. "It will have to be at the end of the day, in case there are other... things... which need to be taken care of."

Bastard. I've been to her home, slept overnight. He's never been with her. Mind you, neither have I, not in the way he meant. I didn't say anything.

"Thursday at 4:30 works for me."

I looked at Karen's calendar. "Yes, that will work."

"Excellent. Just be a good secretary, and bring us some coffee and muffins, or something for the meeting."

I grimaced, but didn't say anything. I had grown accustomed to Karen giving me menial tasks, but not him too.

We needed him, and I couldn't fight him. I simply nodded, and left the office.

Later, I was sitting in the bathroom stall. This had become my habit, after being overly conscious about my short stature and small penis, when standing next to other men at the urinals.

I was accustomed to being ignored. What I was not prepared for, was being mocked behind my back. Two guys walked in, chatting and joking with one another. I think it was Ross and Jonathan, but I couldn't be sure.

"Have you seen Chris." My ears picked up upon hearing my name. "That dude is finally going full-on sissy. Wearing a blouse, women's tight pants, shoes, and earrings. God only knows what he's wearing underneath, but I'm betting it's panties."

His friend laughed. "The guy was always a weak little dweeb. Maybe he finally realized he couldn't cut it as a man."

"I bet he's still a virgin."

"Of course he is. What woman wants to sleep with a wimp like him? So if you can't sleep with them, join them."

They both laughed.

"I wonder how far he'll go. I'd love to see him in a skirt, doing his nails. Looking the part of a sexy secretary."

"Yeah, with heels, styled hair, and makeup."

"He might even look hot as a chick. Kind of does already."

"Well I'm not letting that sissy get near me."

"I don't know. I hear sissies are the best cock suckers. They're eager to please, and know how to worship a cock."

They were both laughing, as they finished washing their hands. I waited a few minutes after they left before exiting the washroom, not wanting anyone to see me.

When I arrived at my desk, Karen was now here. She looked at my outfit and smiled at me.

I smiled weakly in return. I was still slightly red faced from tears and humiliation in the bathroom.

Karen motioned me into her office, and we sat down.

"I really do like that outfit on you. And the earrings really compliment the look."

I nodded. Appreciating the compliment, but not really accepting it. This was why the guys made fun of me.

"What's the matter?"

"Nothing," I muttered.

"Christine, you can tell me sweetie."

I looked up at her, startled that she had used my femme name here in the office. I was about to object, but then I lowered my head again. What was the point of arguing?

"Did the ladies not like your clothing? I'm assuming you joined your friends for lunch again," she prompted.

"No, they were fine," I mumbled.

Karen continued to stare at me.

"It was the guys. They think I'm a sissy cocksucker. Someone who should wear a dress, because he has no hope of ever being with a woman."

Karen moved around the desk to stand in front of me, resting against the desk. She stroked my face gently.

"I understand why you're upset." She paused, not sure if she should continue. "But this can't be the first time you've had guys making fun of you."

"Well, no." I looked up into her eyes. "But are they right about me being a sissy. A loser."

"Oh Christine," she feminized my name again. "You're not a loser. I love you. You're sweet, and gentle, and affectionate."

"And a virgin," I interjected.

"Well yes, we talked about this. Your little penis doesn't belong inside a woman. You give pleasure to women, to me, in other ways?"

"Yes," I nodded reluctantly. "Happy, Obedient, Powerless, Empty."

She gave me an odd look, not understanding the reference, but seemed pleased by its core message.

"Yes, you should be happy being obedient. What was that again? Happy, Obedient, Powerless?..." she trailed off, trying to remember the exact phrase.

"Happy, Obedient, Powerless, Empty. It's a meditation, or hypno therapy if you like, for sissies. Someone gave me a link some time ago, but I only watched it last night. I needed some help obeying your rules, and this helped. I think."

"Someone?" she gave me a questioning look. I only blushed and looked sheepishly to the floor. "Well," she decided not to pursue the question,"... I think it worked based on your outfit and demeanor today. Very becoming." Her smile was reassuring. "I trust it helped you keep the other rule as well."

I nodded my head. Though the news pleased her, I was embarrassed to look her in the eyes.

"Well, I'm glad you were a good boy?"

"You mean be a sissy who does whatever you tell him to do."

"I mean a boy who is pretty, and likes to wear pretty things to make me happy. I mean a boy who gets to spend time with me, to touch me, and lick me."

I noted that she called me a boy, and didn't deny wanting me to be an obedient sissy. Yet the truth was, those things did make me happy when I was around her.

"And what about the guys joking about the dress, and the cock sucking?"

She sighed. "I've told you before, I don't think you're gay." She paused to stroke my hair, and look me in the eyes. "But they are right about the dress."

I was startled. "What?!"

"I think you look pretty wearing a dress or a skirt."

I shifted nervously in my seat but didn't respond.

She continued to stroke my hair. "You have no idea how much I wish that I could put you on your knees, and have you licking me right now."

I stared at her with wide eyes. Shock? Arousal? What did it matter? We couldn't do it here. But then again, why not? I would hardly be the first secretary to do some 'work' under the desk.

I smiled mischievously at her.

Karen chuckled and shook her head. At the mere mention of cunnilingus, she had me hooked.

She leaned forward and kissed me. "I missed you last night." She sighed, "And unfortunately I have an event tonight as well." She was staring at me, delighting in the pretty blouse and my look of longing, and wishing she could do more.

She stood up straight, and walked back behind her desk. "This does not mean you have permission to play with yourself tonight."

I looked like a forlorn puppy. Yet, I didn't say anything. I knew I would obey her, no matter how much it frustrated me being on edge.

"And keep watching your videos. Happy, Obedient, Powerless, Empty."

I nodded. "HOPE videos."

She grinned. "Hope. I like that. Just keep it up. And no touching."

I nodded once more. My gaze once more on the floor, submissively.

"OK, let's get back to work. I need to wrap up a few things before I head to tonight's forum."

That evening was agonizing. I fantasized about her constantly, and when I watched the videos I was craving the chance to once again be kneeling before her. I had to make a conscious effort not to touch myself.

* * *

Thursday morning I awoke with a sense of relief that I had made it through the night without touching myself.

Deciding to wear the pink pajamas to bed made it all the more difficult.

I looked at the closet and pondered my options. Getting dressed in the morning used to be something I did with barely any thought. Yet now there were choices. How daring was I willing to go? I knew Karen wanted me in a dress or skirt. Frankly, I suspected the other ladies would like it as well. Yet, I didn't have the courage to go that far. And there was only the dresses I wore home on Sunday and Monday evening.

Part of me still thought this was ridiculous. I should grab one of my shirt and pants from the pile of clothes on the floor waiting to be donated. Yet after 2 evenings of meditation encouraging me to surrender, the thought barely occurred to me. I wouldn't dare receive Karen's cold rebuke, as I did on Monday.

The rose-coloured blouse I selected would please them. And while I selected a simple pair of black pants, it was clear that they were meant for a woman. I debated wearing the heels I wore on Sunday. However, they didn't match the pants. Given the positive response I had received thus far from the ladies, I really wanted to impress them by wearing heels. For a moment, I looked back at the dress. The shoes would go with them. It was tempting, but I still couldn't do it. Yet, I resolved to buy a pair of black high-heeled shoes.

Now out of habit, I brushed my hair back straight and elegant, and put in the earrings.

* * *

At the office, the warm smile I received from Karen removed any second thoughts I may have had. I should have worn the dress.

After not being with her for the past 2 nights, and most of yesterday, I was delighted to see her. I was like a faithful dog, staying close to my owner.

It was nice to be back in our routine. She deliberately gave me menial tasks, which I promptly did. Her brushing against my back or arm, to make me acutely aware of her presence. And these subtle touches, now through my satin shirt, sent shivers down my body.

I was surprised when she encouraged me to join the ladies again for lunch, and did not join us. I suppose she wanted me to feel that I was just one of the ladies in the secretarial pool. Even understanding her manipulation of my self-perception, I enjoyed myself.

They liked my new top. And seeing their delight in my feminine attire, I once again wondered if I should have simply accepted it and worn the dress.

As 4:00 came around, Karen gave me one more menial task. She asked me to grab two coffees and muffins for her meeting with Marcus.

I grimaced slightly. This was precisely the task which Marcus had assigned me as a good secretary. I was happy to do it for her, but it was humiliating having to defer to him as well. Despite my embarrassment, the order came from her, so I obeyed it.

Before the meeting, Karen called me into her office and shut the door.

"Christine," she had returned to her practice of feminizing my name in private. "I really missed having you at home last night."

She missed me. She missed me. How can I adequately explain the exultation I felt from those words?

"Now, I may be a while with Marcus, but I'd like you to come to my place tonight."

She handed me a key, and a scrap of paper with the PIN # for her alarm written on it. "Would you mind making dinner for us? You may have to pick up some groceries on the way."

I was stunned and overjoyed. She was giving me the key to her home. Another first. I had never been in a relationship, and certainly not one where I received a key to the woman's home. I nodded vigorously.

She smiled and kissed me on the cheek. "Good boy."

There was no time for anything else. Yet now I knew there would be time this evening.

As I exited the office, Marcus was approaching. He noticed the coffee and muffins on the table and grinned at me.

At any other moment, I would have been bothered by him, but I had just received Karen's key. Nothing was going to get me down.

On the metro train, I did receive the odd questioning look, 'Is that a guy or a girl?' I even had one glance from a guy who was attempting to surreptitiously check me out, thinking I was an attractive woman. It made me suppress a giggle. If he only knew. Or maybe he did, and cross-dressers were his 'thing'.

It was hardly the first time I had received odd glances in public, but I was becoming strangely comfortable with it.

I found a grocery store near Karen's home. And now that I was making dinner for her, I bought better quality ingredients than I would normally for myself.

And when I arrived at her home, I was so excited that I had trouble keeping my hand steady to unlock the door.

And once safely inside, I rushed to the kitchen and began preparing dinner. She was already pleased with my cooking, but now I really wanted to impress her.

Once again, I was happy to be in the kitchen, preparing a meal for my lover.

My timing was perfect. The dinner was ready, just as she came in the door. Even the table was set, including a set of romantic candles. I was beaming with delight, anxious to see her smile and expecting her kiss of approval.

I was dead wrong. There was that dreaded icy stare the moment she saw me. I was crestfallen and confused. What had I done wrong?

"Christine." She was at least feminizing my name, which was generally a sign of affection. However, her tone was that of a disapproving parent. "Leave the food. Put it on simmer, or whatever you need to do. Then meet me in the living room."

She then turned and left the room.

In & out. Cold stare. Sharp-toned instructions. No kiss. And then out.

I felt like I had just been hit by a tornado. And it was still not clear what I had done wrong.

It wasn't the dinner. She hadn't even tasted it. Could it be something at work? That bastard Marcus, what did he say? What could he say? Goddess knows, I don't trust him. Yet there was nothing to tell.

I quickly had things wrapped up in the kitchen so everything would be warm and ready when we were.

I found her sitting on the straight-backed chair. The one she was seated at on Saturday evening when I was permitted to lick her. Was her anger a ruse, a means to quickly get me on my knees and servicing her? My little penis twitched at the memory, and the faint hope.

I stood before her nervously, wishing she would point to the floor at her feet. Please let me kneel down before her, and worship this beautiful woman.

No such luck.

"Christine, you broke your promise."

"My... promise?" My mind was circling, what promise?

"What are you wearing?"

I looked down at myself. I was wearing the same slacks, blouse and flats I had been wearing all day. The outfit she liked earlier.

"You promised that you would wear a skirt or dress in my home. No pants. That was only 2 days ago, the last time you were here. And here you are, breaking your promise, the first chance you got."

"Oh, I'm sorry." I looked sheepishly at the floor. "I was so excited about dinner. I didn't think about it."

It should be noted that she was wearing pants. She rarely wore a skirt or a dress. And it's not like I was wearing overtly masculine clothes, quite the opposite.

She sounded calmer, but still upset. "I appreciate your instinct to please me. And you do belong in the kitchen. The dinner smells delicious. But a promise is a promise. I let you wear pants in the office, so you could maintain your masculinity. Your sense of independence as you described it."

Woman's slacks were masculine? Not to mention the rose-coloured satin shirt, pantyhose, earrings, and lady's flats, which I was also wearing. Wasn't that enough?

The fact that I was terrified to wear a dress at the office told me that it wasn't.

Even sitting down, her presence was commanding. "When you are here, I want you to look pretty. I want you wearing a dress or a skirt. I want your clothing to be feminine. That means pink, flowers, hearts, frilly, lace. Nothing that is remotely masculine. Heels. It was a pleasant surprise when you walked in heels with ease. They give your legs a lovely arch that I want to continue to see. You know how to apply makeup, and brush your hair. I expect it!"

I had a lump in my throat. Yet, it was also exciting. Her control both scared and aroused me. And there was no question that I was starting to enjoy dressing as a woman.

Karen paused for a moment to gauge my reaction to her ultimatum. Was I going to challenge her or would I submit?

I continued to look to the floor, and didn't say anything.

"Now I believe broken promises should have consequences. Take off those pants."

I looked at her, puzzled. I now expected to go and change. Yet her eyes were upon me, not dismissing me.

"Now Christine!"

I scurried to comply.

"You better be wearing panties under there, or else I'll be extremely disappointed." She remarked, as I started to undo the zipper.

"Yes ma'am," I blushed. "I threw all my underpants in the garbage."

"Good," she responded with a smile. Equally pleased that I called her ma'am, as by the pink panties I was wearing.

I shifted nervously before her. My little penis strained against the panties and pantyhose, but there was no noticeable bulge.

"Now, over my knee."

"What?!"

"Over my knee. I'm going to spank you for breaking your promise, and wearing pants at home."

"Spank me?"

"Yes dear. It's time for your punishment, and then we can move on from this."

I looked at her for a moment, staring into those unrelenting eyes.

"Don't make me wait Christine, otherwise I'll have to punish you harder."

Reluctantly, I bent over her knee. My hands and feet braced against the floor, leaving my ass in pink panties, perfectly placed for the spanking.

Mother had always been strict with me as a child, so I was not unfamiliar with this position. Although, it had been many years since then, and I was no longer a child. It was humiliating but that only fed my excitement. This being Karen, the woman of my fantasies and not my mother, my little penis pressed into her lap.

WHAPPP. The first blow caught me by surprise.

The second blow landed on the other cheek. I believe she was pausing for effect, as she altered slaps to each cheek. WHAP, WHAP, WHAP, WHAP.

A few more in quick succession, caused me to gasp.

She then hooked her fingers into the waistband of my panties and hose, and pulled them down to my knees.

My penis was now exposed and pressed into her lap. My humiliation and excitement intensified in equal measure.

And then the slap landed with a loud crack. WHAP. It really stung.

It was amazing how the thin panties had shielded me from the pain. And now that her blow landed on my bare bottom, the sharp pain radiated through me.

A second blow. WHAP. And then more in an even flow. WHAP. WHAP. WHAP.

My bottom felt like it was on fire. And no matter the pain, no matter how much I attempted to will it away, my erection would not go down. I was nearing the point of climax as my penis rubbed along her inner thigh.

WHAP. WHAP. WHAP.

I started to cry and whimper, begging her for mercy. However, she was not having any of it. Instead it intensified.

There was a slight pause as she retrieved something from the side of the chair.

I attempted to get up, but she immediately placed her hand on my back, locking me in place.

And then a hard WHOPP. It didn't have the same sharpness of her hand, but it was a stronger blunt pain. I suspect a wooden hair brush was the instrument of my discipline.

WHOPP. WHOPP. WHOPP.

I was groaning and whimpering. My ass burned with pain. Yet with each blow, I shifted forward and my little penis rubbed against her. It was an overwhelming mix of pain, pleasure and humiliation.

WHOPP. WHOPP. WHOPP.

I squirmed, and attempted to break free. Yet her hand on my back was firm. No escape for me.

I whimpered and begged. "Please Karen. I'm sorry. Please. I'll wear a dress. Please." Tears rolled down my eyes.

Yet even as I begged for mercy from the pain, I was struggling not to climax from the pleasure. That would seal my humiliation.

My pleas went unanswered. WHOPP. WHOPP. WHOPP.

And then it was over. Karen released her hold on me, allowing me to roll off to the floor.

She held out the hairbrush to my lips. Her demanding stare making it clear what protocol was expected.

I kissed the wooden hairbrush.

She smiled, and patted my head affectionately. "Good boy. Now you can go get changed. There's some lotion in the bathroom which I suggest you use to cool your bottom."

She was so matter of fact. I needed punishment, and she had put me over her knee and spanked my bare bottom. Me, a grown man. Yet for her, this just seemed appropriate.

I certainly wasn't going to argue and risk further punishment. "Yes ma'am."

I pulled up my panties and hose, stood up, and walked upstairs.

She was right about the lotion. It did help. And the reprieve allowed my erection to subside.

I then went to what I now regarded as my closet. I flipped through a few options. I debated wearing a dress, but I still liked the pink blouse I was wearing. That led me to a cute black skirt with a red rose pattern. It matched nicely with my top, and I instantly felt better wearing it. I selected a pair of red heels which looked pretty with the rose-patterned skirt.

I was about to head back down, but then I remembered, makeup. Makeup and hair.

I sat down by the vanity table, and set to work. She was waiting for me, so I didn't want anything elaborate. Just some blush, eyeliner, and lipstick. A quick routine.

The time we spent on Sunday with my eyebrows now helped to get them just right with just a light touch-up. Fortunately, my eyebrows were naturally thin, and I had smooth skin.

The overall effect was amazing. Even I couldn't believe it was a man staring back at me in the mirror. I didn't just look feminine. I looked hot. I looked like a woman I would fantasize about, but never have the nerve to approach.

I was a happy, obedient, powerless and empty sissy. I did a little twirl before the mirror and giggled.

I then headed downstairs. Best not to keep Karen waiting.

I found her in her favourite spot, resting on the sofa. She had been reading something on her phone, but stopped the moment I entered the room.

She smiled. "Oh, that's pretty. Much better. Don't you feel more comfortable?"

I nodded in agreement. These heels were not designed for comfort, but that wasn't what she meant anyways. She meant pretty feminine clothes fit me, reflecting my true self.

She twirled her finger, and I obliged with a slow 360 turn. Karen ran her hand slowly along my bum, feeling the contour. "Very nice. This really highlights that pretty ass you have."

I blushed. No one had ever complimented my body like this. Certainly not in a sexually aggressive tone that Karen was using as she felt my ass.

My ass was still sore from the spanking, but that only heightened my excitement.

"OK sweetie, now that you are properly attired, let's enjoy the wonderful dinner you prepared."

I smiled. Everything was forgiven, and now I could woo her with the dinner I had carefully prepared.

"Yes ma'am." I rushed off to the kitchen.

We enjoyed our romantic dinner, with the candlelight setting a romantic mood. The light from the flames gave her face a golden aura. Staring at her, one could truly believe she was a goddess. And the moans of pleasure as she savoured the meal, priceless. I was gushing from the praise I received.

My reward was to make her gush. We returned to the living room, and once again she sat in the straight-backed chair. This now had two connotations in my memory: discipline and worshipping her body. Both requiring surrender.

She removed her pants and panties, and sat back down. Then the simplest of gestures which meant so much. She pointed to the floor.

I immediately dropped to my knees and kissed her feet. She smiled, appreciating my immediate desire to serve and pleasure her. I steadily kissed my way up her leg, kissing and tiny licks to taste her flesh. It felt like I was moving quickly, but it seemed she was anxious for the main event. As I reached her pussy, I could see how wet she was.

She pushed my head into her, forcing me to lick long and deep. And once again, there was that sweet aroma filling my nostrils. And her nectar on my tongue. I sucked it up greedily.

I licked, kissed, and caressed her through most of the night. Worshipping her gorgeous body. Responding to every demand. Eliciting multiple orgasms.

And at the end of the evening, sitting on my pink bed, she stroked my inner thigh, under the skirt. Her hand just graced my little penis and then moved away. It had been 5 days since I last had a sexual release. The quick handjob from Karen on Saturday evening in the hallway. She had forbidden me from touching myself, and I had obeyed. Suffice to say, I had a lot of pent up sexual energy. I was nearly begging for her to touch me.

She grinned, knowing full well what power she held over me. She clearly loved to torment me. Yet eventually she had her fun. Her hand gently rubbed my penis through the sheer nylon panties.

She stared into my eyes. "You have my permission to cum."

And just like that, I orgasmed. My ejaculate largely trapped within the panties.

She raised her fingers to my mouth, and I obediently licked up the bit of cum which had escaped.

"Good boy. Now get a good night's sleep." She kissed me goodnight, and was off to her room.

This left me in my sticky panties, but it didn't matter. I was home, my mistress was happy, and my pent up sexual frustration was now gone. All was right with the world.