Man Disciplines Sissy Ch. 05

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.

*

I was jittery all the next day. I hadn't slept well, at first, either. As I lay in bed thinking about Daddy, the things he said, what we had done, alone in the locker room, I squirmed, tossing and turning. I even started to whimper and cry a little when I remembered thinking I had finally managed to quit my sissy tendencies. They were tears of confusion more than real emotional distress. Well, maybe a little-the emotional part. I was thinking, too, in an uneasy way about what he had said about contacting me.

I had to see what he would want, Monday night, and the rest of the week. It made me think again about dresses, swishing around my thighs, tight silky panties, nylons and high heels. All the pretty little things I didn't have any more. Ray had been so disappointed when I'd told him I didn't have my outfits, that I'd purged it all. And he said he was going to contact me with instructions. Would he tell me, command me to buy some clothes? Was that what I was expecting? My mind kept returning to it, because it was very much what he would be expecting.

I dozed, then awoke and tossed and turned again, and I noticed my hard little cock, throbbing as I squirmed under the hotel covers, emotionally confused about what I was, and what I craved, and I thought about stroking it off so I could get to sleep, but no. I didn't want to surrender to it, I didn't want the pleasure. Finally though I did drift into real sleep, and slept hard for almost seven hours. When the alarm went off, it startled me awake, and almost instantly, I thought of him again, and a shiver ran through me. Remembering, I felt his hand sliding into the back of my damp bathing suit, and in my bed my knees clenched together and I moaned into my pillow.

And later, at the conference, I tried to concentrate on my work, talking to customers and partners, going to meetings, attending sessions. Every once in a while though, my mind wandered...back to Daddy and things he had said. And him behind me in the shower, soaping me, humiliating me. I squirmed a little in my seat in the meetings, and hoped nobody noticed. My bottom still felt a little warm and sore from his spanking me in the locker room, and later too, when he had me leaning against the wall in the shower, penetrating me, and when I sobbed through a ruined climax.

My mind raced back and forth. I remembered him catching me earlier in the locker room, and standing in front of me as I sat on the bench, looking at my face, watching my eyes as he slowly pushed his sweaty workout shorts down to his knees. His hard cock sliding between my lips. I thought of his soapy twisting finger. The anal wink. A couple times as the morning passed, daydreaming, I wasn't listening when people talked to me, and in the afternoon my concentration was even worse.

Sometimes at a session I would glance around the conference hall, wondering if he was there, if he was watching me, but I never saw him. When I got back to my room at the hotel, a little after 4:00 PM, I threw myself on the sofa, and my mind was racing. Maybe I could avoid him, I thought. Part of me wanted to. I had purged, I wasn't a sissy anymore. But now I wasn't so sure. He didn't know where my room was. He didn't even know my real name. He had said he was going to contact me with instructions, but I had deleted Lana's secret sissy email account. Maybe I could just push it all out of my mind.

But instead I pushed myself up off the cushions, up to my knees, leaning on the back of the sofa, and I looked over at the little desk, with my briefcase on it, and my laptop.

Daddy was waiting. I knew it. Although I hadn't seen him all day at the conference, I knew he was out there. Somewhere.

And I could simply avoid him, if I stayed in my room as much as possible. It was a big hotel, a huge business and event complex, and he didn't know where I was located. Was it foolish, wishful thinking to believe I could simply avoid him?

And a creeping, infiltrating thought; what was it about Ray, about Daddy that made it seem like he could read my mind, could read Lana's mind, even when he wasn't anywhere nearby?

Still, I was in town on business, and I needed to check my work email. I went over to the laptop computer and switched it on, out of standby so it came up quickly.

There were fresh emails from the office, and a few clients.

But there was one email, one that had arrived about halfway through the day, that didn't look familiar, but its subject line and sender sent a chill up my spine.

The subject was: MB2SBx Conf: Compliments on Best Practices Forum This A.M. The sender was R. B-...

My heart started to quicken, my breathing speeded up, and I could feel my veins jumping a little I stared at this unfamiliar email in the list. Was R. him? Ray was somewhere in this hotel, I knew that. Or somewhere nearby. I was thinking about him. All day, my mind kept returning to him, and last night, and what he had said. What we had done.

I didn't open the message. I just looked at it. I stared at it. I read the subject line, over and over. I stared at the name.

Had he found me? Did he know who I was? No, it couldn't be! No!

But I knew it was possible. And with a sinking feeling, a feeling that crept over me like an itchy blanket, I knew it was more than possible. A chill swept up my spine as I thought about it, the practicalities, how easy it would be to identify somebody. This business event had only five morning sessions, all on the same floor of the conference hall, and all he had to do was visit each panel forum briefly, spot me sitting and participating at the best practices panelists table, then look that session up in the conference program guide, and he'd have my email.

It wasn't just possible. It wasn't just probable. Staring at the letter R. in that subject line, I knew that this email was from Ray.

Daddy was on to me. He knew who I was.

I moaned, I sank, and I half collapsed on the comfortable desk chair there in my hotel room. And yes, inside me, Lana stirred, sparked, and came back to life. No! No no! I whispered.

And I realized that I was too excited, that if I didn't do something to shift or douse the erotic emotions I was feeling, that it would happen again, he would call me honey again, he would have me in a dress again, he would send naughty Lana to stand in the corner again, dress lifted and bottom bared, ashamed and exposed, and he would have her over his knee again, panties pulled down, spanked and sobbing, and on her knees, again, needily nuzzling his hardness through his gray flannel, his hands firmly cradling her sissy head.

He had ordered me not to play with myself. Well, I didn't have to listen to him. I needed to cum, I needed to clear the sissy thoughts out of my head, I needed to concentrate on my work, on my real responsibilities, and the best way to forget about Ray, about Daddy, was to masturbate, now. Then I could tamp down that sexual, erotic pressure that had been building up inside me for a week. I could avoid him, and finish this conference week, and go back to my home state.

Images I like to look at, when I masturbate, I guess they're considered fairly tame. I love pictures of mature women in pretty clothes, the way their lovely legs stretch out and down from their dresses and skirts, firm thighs, knees, calves, offset by glamorous high heels, pumps or sandals. I love their pretty hair framing their female faces, beautiful eyes and polished red lips. Busts, curves, hips, thighs, calves, ankles. I like vintage images, the ones with longer skirts, tight ones, or swishy dresses, and '60s housewives, looking feminine and alluring. Back views of the way their ample hips curve to slim waists. Short videos of feminine hips swaying, females walking in their high heels, seeing them walk and sit, their thighs crossing and uncrossing.

And I just love, maybe more than any other kind of image, the ones where an attractive woman is sitting in a pretty dress or skirt and blouse, perhaps doing her hair or makeup, her legs clad in silk or nylon, crossed at the knee, one high heel on the floor and the other hanging in the air. Or she's sitting legs not crossed, always in a suit or a dress, maybe a flirty skirt, knees together, the kind of view where that lovely triangle of shadow is visible between her knees, or sometimes even up inside that transparent shadow there's visible a hint of white, perhaps a lace trimmed triangle gleaming its subtly tasteful suggestion of feminine white panty.

I opened the directory where I keep a few hundred of these images, and opened the first one, and stared at those pretty plump knees as I opened my pants and slid them down, and stroked the front of my white briefs. My penis stiffened. I was looking at the pretty female, but I was thinking about Ray. About Daddy.

I slid my left hand slowly into the waistband of my briefs, and clicked back over to my email, and hovered over the one from R.

I moaned a little, thinking of R. as my fingers slid over my penis, cupping and teasing it. I clicked the message, and it opened.

Lance,

Nice insights on the morning best-practices panel. Glad I could catch a bit of your presentation. Very professional. We met briefly at the hotel yesterday, if you remember. I think I understand better, now, some of the unique challenges faced by someone in your specialty. Sorry I think I may have misunderstood your viewpoint when we chatted. Can you meet me in the lobby at 4:30? I'd like to explain, if you have a few minutes.

Ray B-

I had already slid my hand out of my briefs. I looked at the clock on the computer, which read 4:20.

I flipped over to the pretty pictures again, and slowly stroked the front of my briefs. My penis was very hard, straight up, its three-and-a-half inches forming a hard little rod under the white cotton. I sighed.

I closed the picture, closed the lid on the laptop, and pulled up my pants. Ray knew who I was. But he had the class and courtesy to send a safe, "business" email. I really couldn't ignore him, and I wasn't sure I wanted to. I wanted to want to. I wanted to be a man, again. One way or another, since he knew who I really was, I had to go down to the lobby and talk to him.

++++

He had his suit on-dark blue flannel, smartly tailored, with a blue oxford shirt and a maroon silk tie. Looking very handsome, of course, sitting in one of the furniture groupings in one of the lobby nooks a bit removed by plants and screenings, with one ankle up on the opposite knee, he was reading the sports page of USA Today.

He spoke right up, lowering the newsprint to nod at me. "Ah, there you are. I'm glad you came, Lance. Please have a seat." Hearing him say my name out loud reinforced his newfound power over me, and I looked at his eyes, and he looked at mine, and we both realized this. He put the paper down on the coffee table and nodded me to the chair across from where he sat. His voice was smooth, friendly, casual but businesslike.

"I got your message," I said, sitting. I gave him a little smile and nod to indicate that I knew he pretty much held all the cards. I took a solid breath, ready for him to put me back in the girly place where he liked me to be.

But he didn't.

"Yes, or else you wouldn't be here, would you?" he said, with good humor. "But you know, Lance, I'm impressed. I meant what I wrote, in the email, about your participation on the panel. You really know the details; you're quite thorough and organized. I think I need to re-evaluate the impressions I had formed about you."

"Um, well, R..." I hesitated. He knew why.

"Yes, call me Ray!" he said, quickly, relaxed and assuring, but not without a small ironic daddy chuckle. "By all means! I want you to think of us as colleagues, I mean it." He waited.

"Well, yes. Er...Ray. And, um, what about..." I hesitated again. There was something weird about all this. After what we had been through. Last night, and before. He was so regular now, just Sales Manager Ray, doing his business-pro thing in a hotel lobby.

He nodded. "Last night? I'm sorry Lance, I know I can be, well, somewhat excessive in my attitudes sometimes when I get lost in the moment. And listen, that's what I meant in the email. We can be professional. I'm interested in you, Lance. We're professional colleagues. I'd like to sort of, well, get a do-over, start fresh, on that basis."

He was sincere, serious, and very effective. I was buying it. Also, in the back of my mind, I was probably thinking, I have no choice, really. He knows who I am.

"Okay," I said. Ray uncrossed his leg, both feet were now flat on the carpet, and he leaned across the little coffee table, looking at me, and he reached over to give a friendly, reassuring tap on the side of my knee.

"Good!" he said. "Listen, I've still got a few minutes before I have to go to that reception banquet. How about we have a drink together?"

"Sure, Ray," I said.

We headed for the lounge. As we were passing a central area with a small fountain and some floral plantings, Ray looked at his watch, and then he snapped his fingers, seeming to suddenly realize something.

"Hey, um, I just remembered I need to check something for a client I'll see at the banquet, on my laptop," he said. "Okay if we have that drink from the mini-bar in my suite?"

Hesitating, I slowed my next steps, but then felt Ray's hand on my back, not forceful, but firm and friendly, steering me. "Uh, okay," I said, and we were heading for the elevators.

"We can speak more openly in the suite anyway," he chuckled. "Don't worry; I've got to head over to the Crown Plaza in about twenty minutes, anyway."

In the elevator, I watched the numbers blinking on and off as we approached the fourth floor. As it slowed to a halt, again I felt Ray's hand on my back, steering me out of the elevator, taking a left, and then his arms are swinging freely again as we walk down the hall, stopping at 419. Ray gave me a little grin as he swiped his key card, and we went in.

Ray went straight to his laptop, already opened up the long counter-style desk area with a wall-length mirror above it.

"Go ahead, help yourself, this'll just take a minute," he said, pointing at the mini-bar refrigerator combo, while he sat in the desk chair and woke up the computer.

"Can I get you something?" I said. I selected a ginger ale.

"What are you having?" I held up the green can.

"I'll have one too, perfect," he said. "Make yourself comfortable." He nodded toward the sofa, coffee table, and chairs arranged in the large suite. With the drapes open, the afternoon light slanted into the room, keeping the whole space bright.

I handed him the ginger ale and sat in one of the chairs, across the coffee table from the sofa. Ray put his can on the desk and tapped a few more words out on the laptop keyboard, then picked the ginger ale up again, swiveled his chair around, and we both opened our drinks, and sipped.

He raised his can. "I'll be into the scotch at the banquet, but even then, just one, maybe two. My days of convention excess are way past!" He sipped again, and I took a good drink from mine.

"I don't like alcohol much," I said.

"Good!" Ray said. "That's interesting! I meant it; I'm interested in learning more, more about Lance, the professional, the man. What makes him tick, where those insights come from." The swivel chair squeaked as he got up, then he stepped around the arm of the overstuffed sofa, and sat in the middle of it, directly across from where I sat.

I was still uneasy, wary. Ray was being friendly, and I'd seen little flashes of a tender side, but this was really new, this we're really buddies attitude, and I wasn't sure it was real, or if it was, whether it was a good thing.

He looked at me as he settled into his seat, and sipped his drink.

And we chatted about work, the conference, the industry. He asked me some of my work history, the companies, positions and promotions, we compared notes on some things, and also remarked on some of the differences he'd seen in this industry, the changes, him being over a decade my senior.

During a lull, we both stopped chatting and sipped our ginger ales. He looked at me, and slowly put down his can on the coffee table.

"And there in your office," he said. "Nobody knows? Nobody has a clue?"

My hand tightened on my ginger ale. Although I tried to remain unfazed, I became suddenly self conscious. As I looked at Ray, I tried to breathe and move naturally, but I was sort of frozen.

"What?" I managed to say. I unfroze my arms and put down my can of soda. I looked across the little coffee table at Ray. He stared back at me calmly, and then gave a little smile.

"I think you know what I mean," he said. He didn't move, somehow managing to look relaxed at the same time as he remained completely still, focused on me. I felt an internal squirming. A flush rose up from my chest and my neck, and I felt my face turning red.

"No," I said. "I thought-"

"You thought I said we were going to talk about work? Yes, I did say that. And that's what we're talking about, Lance, isn't it?"

"Yes," I said, quietly.

"So your colleagues at work don't know about you-well, about Lana?"

I shook my head. I looked down. My face stayed red.

"They don't know you like to wear swishy little dresses? Your pretty panties?"

I found myself breathing deeply. The pit of my stomach was a knot of anxiety.

"Look at me, honey," Ray said. His calling me that was like a jolt back to...another reality. I looked at him. He leaned back on the sofa, and his knees drifted apart. I looked at him, because he told me to, and called me honey, and wearing his dominant grin he leaned back in his neat blue suit and crisp maroon tie, and I watched him rest his right hand casually on his right thigh, his masculine fingers curling down and in toward his manhood. Just that gesture, subtle but somehow aggressive, made me feel suddenly weaker, more compromised.

"The men and women in your company have no clue what a sissy you are, do they honey?" he said softly, and his hand slid down and in, a few inches closer to his crotch, and he adjusted his position just slightly, but the effect was a slight thrust, and my sense of weakness, and vulnerability, increased.

Sitting opposite him, listening to him humiliating me, looking at his alpha gestures, my knees moved together, an unintentionally feminine mannerism, and my hands fluttered. I tried to stay centered, but my breathing was already getting faster, in a panicky way. My body was reacting, submitting against my conscious wishes, falling into its latent and effeminate pattern, responding to alpha male body language.

"Speak up, honey," Ray said, words and gestures amplifying his male power. "Answer the question." His hand slid a little further toward his crotch, but his fingers stayed extended, non-clutching. I didn't look, but he knew I saw. I could tell by the way his eyes flashed mine, that he'd seen my oh-so-brief downward glance.

I took a careful breath. "No, they don't know," I said. My voice was small and weak again, trembly and almost feminine, and I wanted to say something else with more voice, but Ray spoke up.