tagTranssexuals & CrossdressersMan Disciplines Sissy Ch. 01

Man Disciplines Sissy Ch. 01


I enjoy nice undies, sexy undies, soft and pretty lingerie, and delicate and dainty clothes whenever possible. I put on these things, and feel feminine and aroused, eroticized....the pretty dress, the wig, the nylons, panties and bra, heels...

I also feel the misbehavior aspect. A boy/male like me, even if it looks sexy or feminine on me...dressing girly is at best questionable behavior and I wonder about being caught and disciplined for it.

On business, I was traveling alone, visiting a large Midwestern city, and I was very excited. I had invited an admirer over to my hotel room.

I think he was a little angry at me when he arrived. He had asked me to meet him first in the lobby, fully dressed, but I wouldn't do it. I am very shy about being my feminine self, even in private, so of course I couldn't do the lobby for him.

When he got up to the room, I heard his knock. Nervous, I had been fussing with my clothes and my face at the last minute, so I had to call to him "be there in a minute" while I slid my blue dress back on, over my white satin bra and panties, black sheer thigh-highs. I had selected dark pink lipstick, clip-on earrings, some face powder and eye shadow. I slid the white satin high-heel sandals on. Finally, I felt ready, and I stood by the sofa, and said "come in."

He was a few inches taller than me, short blond hair combed neatly. A little on the stocky side, he looked strong, and like I already said, he seemed a little impatient, a little irritated. He was dressed like a business golfer, yellow polo shirt, pressed khakis, brown belt and shined brown shoes.

He walked around the room, and looked at me from various angles. He grunted and hummed and syllabled without saying words. But he was nodding too. I think he liked my dress, my legs, my long blonde wavy wig, the way my high heel sandals flattered my calves, and lifted and enhanced my curves, made me more feminine. For a man, I'm small, and on the slim side, which helps. I watched him as he moved, as he looked me up and down.

The first thing he actually said, he scolded me. I had displeased him, he told me in a low, serious voice that held an edge of actual disappointment and a touch of angriness, and I trembled hearing it. This was while he was still standing, walking between the big window and the entry way, watching me, my body language, looking at my body. He made me feel very ashamed. I looked down, clasping my hands in front of me. He scolded me for not meeting him downstairs, and for making him wait in the hall.

Finally, he sat. There was a little round cocktail table, sort of a high table not a coffee table, and he sat at one of the stools.

Then he called me over. He was sitting at the little table.

I was feeling very ashamed and contrite. I hesitated. I didn't want to go to him, I was afraid. He became very firm, his voice dropped lower and quietly angrier. He said "You don't want me to have to get up."

"Get over here," he said.

Slowly, I moved toward him, little steps in my high heels, my dress hem swishing a little around my thighs, looking down. I didn't want to raise my eyes, to see his angry face.

He just looked at me for awhile. I was very nervous. I stood there, and I would look at him, but I couldn't look in his eyes. I looked away. He said, "You must learn to obey, and behave." I nodded, but I was starting to feel emotional.

He backed his chair away from the table a little, and leaned forward, and took a firm grip on my wrist. He tugged, and I shuddered feeling his strength. He pulled my arm, and moved me close to him.

"Look at me," he said, and I looked at him. "You're to be punished," he said. I looked away, and had to try to get control of my breathing. He had a natural authority. It wasn't at all playful

I sniffled a little, I was shaking. I couldn't look at him. But he wanted me to. He had something more to say. He said "look at me" still low, but more forceful. When I didn't look up, he let go of my arm, and then suddenly I felt his hand. He slapped me. I looked up at him, and he said. "That's better. I'm going to spank you, honey," he said.

I was so ashamed, I wanted to cry. I felt very sorry, and very small. I was confused and still trembling, and my face was hot where he'd slapped me.

Then he took charge. He said "Let's have a look," I felt his strong hands on me, grasping both my hips, and he firmly turned me around so that I was facing the table. He was controlling me so I had my hands up sort of, my elbows raised out of his way as he moved me by taking hold of my hips. He was still sitting down. He moved up to the edge of his seat, and I could feel his hands slide down from my hips, to my legs, and then lift my dress by the hem. I felt the coolness of fresh air on the backs of my thighs.

"Look at these panties" he said. I felt his fingers, lightly touching my bottom, tracing around the edges of my panties. "You've been very bad," he said. "And look, you're such a little sissy, wearing these."

I moaned in reaction, and I felt my knees trembling, as he held my hem up and looked at my bottom, toying with my lingerie.

"We'll have to pull them down," he said softly, "You naughty little girl, getting a spanking from her Daddy."

I put my face in my hands, standing there, but he wanted my reaction. My breathing wasn't working right; I couldn't speak for some reason. I was emotional.

"Should I pull your panties down now, honey?" he said. I just sort of shivered, moaning into my hands. "Answer me," he said, but I couldn't. "Hmm," he said, then I felt his hand. On my bottom this time. The first slap was hard and stung in a surprisingly sharp way, and I jumped and my voice made an involuntary sound, a moan. He spanked me through my panties, holding my dress up with his other hand.

"Speak up," he said. "Take your hands away from your face, and answer me honey. I moaned, "No," and took my hands down. "Put them on the table," he said. He stood up. I put my hands on the table. "Look at me," he said. But I didn't, and earned another slap. I felt like I was really about to cry, but I looked at him.

Yes, I finally looked at him, but I could feel the emotions of shame and sorrow and couldn't hold my face from showing it. I was so upset. "Good girl," he said. "Keep your hands on the table". Then he lifted the back of my dress again, and with his right hand, stuck his fingers into the waistband of my panties and started to pull them down, working his hand back and forth.

Now I knew, now it wasn't just going to happen. It was happening.

He scolded me. He told me I was misbehaving, and a prissy sissy. And I started to moan, my face was very red, and I felt his hand sting my bottom. My bared bottom. Again and again and again and again and again and again.

I was gasping, sort of hiccupping, trying to speak. I said, "but, but, you asked me if you should pull them down, then before I could answer..."

He said "Oh, yeah, you speak up now?" and his hand started spanking harder. Oh it hurt.

"Naughty, naughty sissy girl," he said, spanking with the words' rhythm. And then I felt the tears coming. I think he saw it happening too. There was a low armchair not too far away. He moved toward it, pulling me with him. Actually after he sat down he grabbed me by my panties which were bunched above my knees, and pulled me over close. The sheer white nylon and elastic panty waistband stretched as he pulled, and I stumbled a little because I couldn't move my legs well with the panties bunched around my knees. He sat down in the chair, and pulled me close, pinning me between his knees, as he pushed my dress up again and spanked my bottom over and over with his big flat hand, and I really started to cry.

I was sobbing into my hands, and I noticed that he had stopped. He wasn't spanking me.

I was standing between his legs, and he let his legs relax so that I wasn't clamped in anymore. He still held my dress up with one hand, and his other hand was feeling my bottom, instead of spanking it.

"You have a nice fanny, honey," he said. Then he grasped my hips and moved me a foot or so away and turned me toward him.

"Look at me," he said. I sniffled and wiped my eyes a little, trying not to think of how messy my eye makeup must be. I looked at him.

He nodded. Sitting in the chair, he still had his legs open a little from letting me out. Holding my eye, he reached down and put a hand on his thigh, then reached in a masculine way between his legs, and adjusted his crotch. There was something vaguely aggressive, and at the same time nonchalant, about this gesture. It was his cock, his balls that he'd just touched, moved, while I was watching. While he watched me watch him touching. He wanted me to see. And I glanced down afterward, and saw there was still movement in his pants, under his zipper. The long shape there moved gently, as if it was uncurling under the cloth of his pants. He saw me looking, and reached down and adjusted it again. The length of it was sideways, a fat, curled bulge.

"What are you looking at?" he asked.

"You told me to look at you," I said. There had been a little menace, some edge of cruelty in his voice, and I was a little scared now. Before I could stop it, another sob escaped my throat, and a little moaning cry trailed off from the sob.

"Don't get cute," he said, and laughed a little. His laugh was soft of stiff and hollow. "You're looking at my cock, you little sissy. You need cock, don't you?"

He reached down and now openly fondled the front of his pants, grabbing himself in a masculine, sexual way. I gulped. I found myself staring.

"No, I, um, oh I..." I trailed off.

After groping himself through his pants, he kept watching me, but both his hands went to the belt buckle, finding it without looking. His fingers unlaced and unbuckled his belt, then unbuttoned the khakis' waistband. "That's right, sissy," he teased, "Keep watching..." And he unzipped his pants, and pushed the flaps open, and I could see that bulging in his white cotton briefs. Now he pawed his package again with his big right hand, watching me. I could see his cock under the thin cotton, its fat length crossing the front his underpants, not erect but not limp either.

"Yes, honey," he said squeezing himself through the cotton, "Daddy needs some attention from his sissy girl."

He sat up straight again, and reached for me. Once again, his fingers latched onto my panties bunched above my knees, and he pulled. I stepped forward, close to him. "Come sit on Daddy's lap," he said. He turned me around, facing away, and pulled me back to his lap. The backs of my knees hit his knees, and I eased myself down.

I reached back. I was going to smooth my dress under me as I sat, but I guess I was a little rushed, a little flustered, instead I lifted it out of the way, so that I sat on Daddy's lap with nothing under my bare thighs and bottom. My panties were still bunched around my knees.

He scootched me back on his lap, and nuzzled my neck. I could feel his penis against my bottom, warm and starting to uncurl inside his underpants.

"Where did you learn to lift your skirt when you sit on a man's lap?" he said, and laughed.

"And your bottom's warm from your spanking," he said. He was moving his hips, working his cock against my bottom, I could feel it getting harder, straighter. It worked its way between the cheeks of my bottom, and he grunted softly and made little thrusts with his hips. His big hands held my waist, and his strength and confidence made me feel small and in his power. Nervously, I moved on his lap, responding to his motions and, of course his increasingly aroused, erect penis under my bottom. Somehow it seemed more exciting that he still had his briefs on, that there was yet another layer of sensation still to come.

"You feel very natural on a man's lap," he said. "On Daddy's lap."

I felt myself blush. "Aw, you're so cute!" he said, and the edge in his voice was a little weird, sarcastic, and blush turned to shiver.

His hand caressed the side of my face, and I felt his breath on my ear. He whispered, "Such a pretty little sissy you are, baby. Daddy had to spank right away because baby kept daddy waiting and was stubborn, but daddy is pleased you're such a girly boy in your pretty dress, your smooth legs and cute little sissy panties and..."

He slid a hand up my dress, way up, and I felt fingers touching my bra. Fingers slid inside and pinched a nipple.

He continued to get harder under me, wiggling on his lap, and his hand came out from under my dress and wandered up the front of my body. "...and your pretty sissy slut mouth," he said.

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