Man Disciplines Sissy Ch. 06

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Sissy ends purge, buys outfits, makeup, caught half dressed.
11.9k words
4.61
14.7k
18

Part 6 of the 7 part series

Updated 06/09/2023
Created 08/26/2014
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This is a fantasy. Scenes in reality should be built on consent, safety, and communication. No character in this story is less than 21 years of age.

*

Back in my own room, I threw myself on the sofa again, face down, and for a half a minute I just lay there, breathing a little fast, excited, ashamed, squirming a little in spite of myself, thinking of what I was becoming. Rolling over onto my back, I rested my head against the sofa arm, and I took the key card out of my shirt pocket, and stared at it. I took a deep breath, and another. Sissy. Cocksucker. I licked my lips reflexively, and got a little taste of him, his penis, salty and musky. I rolled a little back and forth, just to move, to do something with the energy and anxiety that filled me.

Alone in my quiet hotel room, rolling back and forth on the sofa, moaning softly, as I kept thinking about what we had just done, up in his suite. When he stood and unbuckled his belt and unzipped and opened his dark blue suit slacks, pawing his masculine bulge, that curled shaft making a lump in his underpants, the dick-shaped outline of it protruding over his big balls in their sack, and the grin on his face as he slowly slid his thumbs into the elastic and pushed his briefs down, looking me in the eye as it slowly sprang out and bobbed there, his drooping, swinging half-hard cock with its fleshy helmet knob flared on its tip. How I just stared as he sat, resting his weight on the sofa arm, man-spread so masculine and sexual, beckoning me.

He had just spanked me and I was at my most vulnerable, emotional, as he ordered me to my knees, and put a hand on my cheek, guiding my mouth to him. Licking it. Tasting his whole day of salty manliness. The tip of my tongue on the wet, sticky pee slit. The pink warm knob of it, wet with pre-cum, sliding between my lips, pushing them open, throbbing in my mouth. It was just ten minutes ago. Me on my knees, my bottom spanked sore and warm from his masculine hand, my eyes looking up at him as he held my head and slowly fucked my wet mouth, pulling his hard shaft halfway out and stopping, how he grunted and held absolutely still for some twenty quiet and rigid seconds. I remembered watching his straining face as he suppressed his orgasm, then pulled his oozing tip out of my mouth without ejaculating, the string of pre-cum that drizzled off the tip of his penis and landed on my chin...

Sissy. That word swam in my head, in his soft, low masculine voice. As I lay there on my sofa, I felt my adrenaline surge. My mind suddenly recalled my favorite dress, the swishy dark-blue one, and for a moment I was thinking of getting it from my suitcase, right now, and smoothing it out, sliding my hands between the front and back hems, slipping it up and over my head, wiggling into it, feeling how it hugs my hips and drapes its supple swishy heavy material around my smooth thighs...

But my favorite dress...was gone. My thighs weren't smooth.

It was nearly five o'clock. Daddy was coming back in a little over three hours. He was expecting Lana. And Lana needed a dress.

I got up, and went to the desk where I had my laptop computer, and I sat down.

Using my laptop internet, I did two map searches, for the exact kinds of stores I needed, convenient to the business hotel district where we were centered.

They weren't far away. After a ten minute taxi ride, I shopped. After another five-minute ride, I shopped again, and this time the department store had everything else I needed, in their lingerie, cosmetics and hair-care sections.

And, a little before seven o'clock, riding back to the hotel, in the taxi with my shopping bags, I had the following:

Two dresses, one maroon and swishy, the other tighter, and a pretty, pale blue.

A full slip and two half-slips. Altogether, I guess that adds up to two slips.

One black lacy bra, and a plain white bra and several assorted pairs of ladies' panties.

A pair of white satin sandals with 3.5 inch heels.

Two pairs of pantyhose, two pairs of thigh-highs, and one pair of vintage black garter-style nylons.

A vintage beige garter belt.

An auburn wig, synthetic but decent quality, with shiny wavy curls, shoulder length.

Nair.

Lipstick, eye liner and shadow, and a tube of neutral face makeup.

It sounds like a lot. But riding back to the hotel in the cab, I had to consolidate the four shopping bags I had ended up with, and all the underwear and fundamentals ended up taking up very little space in one medium-sized department store bag, so I decided to put the wig and the shoes in there too, and the dresses and cosmetics didn't take up much space in the other bag, so I nested that inside the first bag, and ended up with one bag, fairly full.

At one point while I was redistributing my items, I felt eyes on me, glanced up and noticed the driver was looking at me through his rearview mirror. He returned his attention to the road, saying nothing. I shifted my glance from the mirror, and, self-conscious, I wondered if he'd been watching while I rearranged my feminine purchases. I felt my face go warm at the thought, but from where I sat in the back seat, I couldn't tell if he was interested, or indifferent. I was sort of glad to not know. In just a few minutes, we would arrive back at my hotel and I would gather up my things and he would drive off to his next fare.

I was a few blocks from the hotel, and the coming of dusk was just beginning to darken the city with the shadows of the taller hotels and office buildings. The driver was a middle aged Caucasian man, heavyset, with faded blue tattoos on his forearms, graying hair. My cell phone rang. I paused my nervous rebagging of panties and slips, and looked at it. It was an unknown number. I was tempted to ignore it, because I needed to get back to my room and...get ready.

I slid my finger across the bottom of the little screen, and my hand trembled as I raised the device to my ear and quietly said "Hello."

For several long, quiet moments, all I heard were the sounds of the city in the afternoon, and the driver's radio, talking about sports.

"Hello?" I repeated. Nerves made my voice squeak a little higher, and a different kind of nerves also made it softer in volume. I guess I was self-conscious about traveling around a busy city, carrying a complete assortment of feminine clothing and accessories.

"Hi Honey," he said. A bolt of sensation surged through my body, delivered by his voice, soft, low, and spiced with judgment, superiority, and flecks of want, desire.

Without wanting to, not yet ready to speak, I pulled in a quick breath and said, "Oh!"

He kept his voice stern, softly scolding; "Is that any way to greet your Daddy?" he said.

"No, I, how did you...do you have my cell number?" I whispered. I looked at the driver; I looked out the car windows.

"Honey," Ray said, his voice still low, a little harsher. "I said, 'Is that any way to greet your Daddy!"

"Umm," I spoke quietly, holding the phone near my mouth, "I can't really talk now, Ray." The driver was looking at me in the rearview mirror.

For several long seconds, the phone remained quiet. Too quiet. Then, he spoke up, his voice dry, careful, and forceful without being raised. "Well, Princess," he said. "Well now. We'll see about that. Now, listen carefully, honey. I don't care where you are, or who you're with. Speak up clearly now, hon, and greet your daddy properly. And while you're at it, apologize for not doing so in the first place."

"Hello, Daddy," I said, clearly now, but not very loud. "Daddy, I'm in the taxi, I'm sorry but, well, you know..."

I felt the driver's eyes on me again, so I looked up, and saw them looking at me through the rearview mirror. They were dark brown eyes, and he had bushy eyebrows.

"Oh, I see," Ray said. "And you don't want the driver, the taxi driver, to know what a sissy you are?"

"Yes, Daddy," I whispered, whining. "Please Daddy..."

"Louder, honey," he said simply. I could hear the cruel amusement in his voice.

"Yes, Daddy," I said louder, and I raised my eyes and stared at the eyes in the mirror, and there was amusement there, too. I heard the driver chuckle. I felt the hot blush of shame reddening my cheeks.

"Yes what, honey?" Ray said. "Speak up, princess!"

"No, Daddy he doesn't know..." I was squirming in the back seat, and my voice was loud enough for the driver to hear me clearly. "He doesn't know what a sissy I am, Daddy." I lowered my voice to a whisper when I said sissy.

"Well, honey," Ray said. "Maybe he knows now."

I squirmed. I took deep breaths.

Ray had to rub it in. "If you had greeted me properly in the first place, honey, we would have been fine. But now princess, he knows a little more about you, doesn't he? All because you couldn't be a good girl and speak up when Daddy needs a proper greeting."

I was angry with Ray for teasing and toying with me this way, out in public, but I didn't dare show my emotion, my frustration, so I just said, clearly but firmly, "Yes, yes, Daddy. Please--" And he interrupted me again.

"He probably doesn't know what a naughty girl you are either, does he?"

I didn't answer. Maybe a little breathy whine, the kind of sound that just happens when you can't quite communicate with any clarity.

The driver was staring, leering at me, his amused eyes reflected in the rearview mirror... I squirmed in my seat.

"Don't worry hon," the driver said, with a dry chuckle. "I'm not into it. You can talk to your, er, your Daddy as loud as you want, or as loud as he wants, no skin off my elbow." Somehow it didn't, well, it didn't help to hear that he was a regular guy, a heterosexual male. I felt my face flushing hot and red again with the shame.

"Please, Daddy," I said. "I'm doing what you told me to do!"

"Uh huh," Ray said. "A pretty dress to wear for Daddy?"

"Yes Daddy," I said softly. "Two of them, one is maroon, one is blue."

"Speak up, honey, I can barely hear you."

"No Daddy please, I don't want to say it out loud, please, the driver..."

The line was silent. He was waiting. Inside me, something that was finely balanced suddenly reached a tipping point, and then...tipped.

"Okay DADDY," I yelled suddenly, "OKAY, OKAY, yes I got a PRETTY LITTLE DRESS TO WEAR FOR DADDY!"

The line was silent again. The driver was shaking his head, and rolled down his window a few inches. He looked like he was feeling a little awkward, I could tell. I heard a high, soft moan break the silence, and I realized it was my own voice.

"Daddy?" I said. The line remained silent, but still no dial tone. He was on the line, waiting.

"Mm hmm," he said, finally. It was just that, just a little soft grunting, but in those two little syllables I could hear all of Ray's displeasure.

I slumped against the window of the cab, still listening to the roaring silence of my phone, and with my free arm, I hugged my bag of girly clothes and accessories for comfort, but it wasn't much help.

"Daddy?" I said. I felt, and heard, my voice crack a little. I was emotional. He still didn't reply.

I tried to take a very deep breath, to regain some calm, but the breaths were just coming and going too fast. I felt a little light headed.

"Daddy, please, I--" I said. Ray interrupted me. The irritation in his voice was even clearer now. His tone was flat, stern, and his words, brief.

"Quiet, princess," he said softly. "But you do realize," he said softly, "we'll see about this when Daddy gets home. Your little...temper tantrum will have to be addressed when we're reviewing your recent behavior."

I started my reply; whining. "Yes, Daddy, but--" And he interrupted me.

Daddy's irritation was even clearer in the next words he said.

"And when I do, princess, one bad little girl will be feeling very, very sorry for herself." And before I could say another word, he clicked off.

I watched the driver as he spun the wheel, pulling up to the hotel's lobby entrance. He had a smirk on his face, and I felt the opposite, because even though I hate when it happens, I couldn't help it but I felt my lips trembling in their emotional frown. Daddy was angry with me.

***

An hour and a half later I was still getting ready.

I had showered and lotioned my legs smooth, and I already had my lingerie on. I had paid extra attention, to my face and body already, nervous and flustered about it, about Ray, about myself. About how he'd managed to persuade me right back to being his needy little sissy, in less than a single day. Feeling half naked in my heels and my half slip, I was about to select one of the dresses, when I heard the knock on the door. Knock, knock, knock-knock-knock. A crisp knock. Firm. A knock that meant business, as they say.

What was this? My heart jumped. Visitors? Who would come to my door? Oh no-no-nooo not a co-worker, no colleagues please please please...

I glanced quickly at the bedside clock: 8:14. Too early for Ray...besides, he had made it clear that I was to get ready, get girlied up and wait for him in his suite. I was almost ready. I just needed to get my things together, final preparations, and there was just enough time to get up to his suite, certainly well before 8:30.

So who was at the door?

I debated in my mind about whether to answer at all. If it was somebody from the office, it would be better for me to remain completely quiet, to not answer at all. I'm standing by the bed, wearing just the white bra, the brand-new smoky-pink satin bikini panties trimmed with silvery gray lace, a slim cream-colored satin half slip, my auburn wig, the caramel thigh-highs, and the white satin sandals, and looking at the dresses I'd bought.

I dropped the little blue dress back on the bed, and as quietly as I could, I glided in my high heels across the room to the door, and if anybody looked I would have looked ridiculous because walking quietly in heels is almost impossible. The stiletto heels still made quiet little clicks as my feet left the carpeted part of the room and contacted the hard tile flooring the room's entranceway.

Just as I was reaching the doorway, the knock sounded again, louder this time, and the sudden sound startled me. The blood was rushing in my ears and I must have jumped a little, my heels clattering just audibly on the tiles. I held very still, and leaned forward to look into the peephole.

The glass lens, already distorting because of its fish-eye shape, must have been scuffed because I could only really see that there was a person there. I took a deep breath, and tried wiping it with my finger, but it didn't clear.

Then, he spoke:

"Open the door, hon. I heard you in there." He knocked again, his pace firm and insistent: knock-knock-knock.

It was Ray.

I swallowed, nervous, and spoke in a loud whisper, leaning against the door. "I...I'm not ready. You said--" But Ray interrupted me. The knob turned and stopped, the door shook a little. "Don't make me have to knock again, open the door," he said.

I turned the deadbolt, he heard the snap of it unlocking, and Ray opened the door and came into the entryway.

I tried to stand steady, but felt myself instinctively cringing a little, lowering my eyes as he looked at me. But his face was bland, inscrutable.

"Daddy--"

He interrupted again. "Let's stick with Ray for now, hon. Daddy will deal with all that a little later, okay?"

"Okay, uh, Ray," I said, touching my hair, oddly feeling self-conscious in my half-dressed state. "Do you still want me to go up to your suite?"

I felt his hand on the small of my back, just above the waistband of my cream satin half-slip. "Yes, of course, but I got done down there at the reception a little early. So here I am. Let's have a look, shall we?" he said, steering me toward the living area with the bed, the desk, the sofa, and the television.

Ray paused briefly to glance over the bed, with the two dresses, and various accessories arranged on the spread. "Mnn hmm," he said, and then he went on by, hitched his slacks using his thumbs and forefingers, and sat on the sofa's center cushion.

I stood, unsure, between the desk and the bed, looking at the dresses, glancing between them and Ray, and thinking about how this was disrupting my plans, expectations. I hadn't put the makeup on yet.

Ray's face eased a little, to a tight little smile. He seemed to sense my confusion, and my confusion was, and had always seemed to be, pleasing to him, and this time was no exception.

"See, honey," Ray said, "As much as I've been enjoying our little..." he paused to find the right terminology-- "Our little arrangement, last night and this morning have made me realize something."

"Can I put my dress on, Ray?"

"Don't interrupt me again," he said. "Leave the dress there, for now. As I was saying, I kind of like knowing your...let's call it your naughty boy side, too. Our meetings before, during last spring's conference, just with Lana...you--or, maybe she--you could hide in there, hide behind your feminine personality, couldn't you honey?"

I felt my face getting hot. I looked down, stepped sideways a few inches in my sandals.

"You were with a man, and you are a man yourself, but stepping into Lana, in a way you were hiding him away inside your feminine character. With your pretty dress on, the wig, heels, the lipstick, you could be Lana, and maybe pretend that this was just, well, a sort of a 'make-believe' thing, your girly side, an act, not really you at all."

I glanced at him. Our eyes locked, briefly. A little shudder of intense feeling passed through me, and his grin flattened a little; he saw it, he knew. He was hitting a nerve.

"But then last night, in the exercise area, and the showers, was quite a different matter," he said. "Lana wasn't ready for me. Lance wasn't ready." Ray grunted and chuckled, and stared so hard at me that I had to look away. I stared at the feminine items on the bed again, feeling a knot forming in my belly, my chest too.

"Last night, Lance, you were caught by surprise. I liked that. There you were, trying to be your confident, conventional self, a regular guy, man of business, on the road, doing your thing. But as soon as I saw you, and you saw me, I watched your manly spirit begin to falter. I liked that, too. Kind of a lot. Something else peeking through, something still male, but beta somehow. Sissy male."

I was taking deep breaths, listening to him, thinking about last night, today, and now. Yesterday, and these last weeks, feeling like a man again, and then Ray showing up and dashing, smashing that idea. And then today, even worse. Playing with my head, treating me like a friend, a colleague, then pulling the rug out from under that, putting me over his knee, and putting his cock in my mouth.

And now. I didn't look at him. I stood half dressed, in heels, nylons, panties, a half-slip and bra, being lectured to. To have somewhere to put my eyes, I kept looking at the clothing laid out on the bedspread. Pretty things. Lacy things. Slinky and swishy things.

And now. Half dressed. Half feminine. Neither here, nor there.

"Honey, look at me," he said, his voice soft but firm. I looked over at him, and he nodded. He had my attention.

"Come over here, honey," he said, and patted his lap. Then he resumed his talking-- "Last night, when you first saw me, that first recognition, when I looked at you there in your tight little Speedo swimsuit, I watched as your masculinity just dissolved right before my eyes. I saw your face fall right into sissy mode, because your daddy was back."