Page 20

Chapter 3

"Here's how we're going to start," she whispered into my ear, her hands methodically removing my clothes. "I'm going to dress you up in the sweetest, frilliest panties I have. Then I'm going to put you in that gorgeous pink dress. Don't you love all the ruffles on it? And look at all those darling pink bows."

"Yes," I breathed, staring longingly at it. "It's beautiful."

Part of me had broken off. I could feel it hanging to me by a thread. It was the part of me that knew better, that knew that dresses were for girls. A part of me that filled me with shame for wanting what made me happy. It desperately clung to that thread.

The dress is yours, now, I thought in awe. It's your life — now.

She pushed my pants and underwear down to my ankles. My manhood sprang out in the cool air, the breeze blowing gently against it. Saskia looked at it openly, a wry smile curling the corner of her lips.

"And once your dress is on, you're going to put on that cloud of a petticoat over there. Then, when you're all done up in your make-up and pretty clothes and sexy lingerie," she continued, kicking my old clothes into the corner. "I'm going to reach underneath and find your little stiffie in all that lace and silk and start teasing you until you beg me to let you cum."

"And then what?" I asked in a choked voice.

"I guess you'll just have to find out," she purred.

I let that hateful part of me go and felt freedom spill through me.

Stockings first. The sheer white silk slipping up my legs made my heart skip a beat and my raging manhood stiffen even further. Saskia helped me put them on, kneeling in front of me and tugging them up my legs. She cast a sideways glance at my shaft, her expression somewhere between amused and annoyed.

I stepped into the pink satin garter belt next, pulling it up around my waist. Saskia showed me how to clip it onto my stocking tops, straightening the seams behind my legs. Every motion tugged the stockings across my skin, the sensation making me shudder. Saskia kept her eyes on my manhood, watching it twitch in response to the stockings.

I bent over and pulled the panties over my legs. The curtains fluttered behind me as the lace trim brushed against the stockings. I bit back a moan as they settled snugly into place. They felt right. The tip of my member peeked up over a satin rosette on the waistband, the last of my manhood disappearing into them.

"How does it feel?" Saskia asked, the iron edge in her voice gone now. "Is it what you always wanted?"

"It's amazing," I answered truthfully.

My skin was electric, awash in new sensations. Even the way the panties curved against my rear and cupped my package was new and exciting. Every step, every breath, every motion revealed new pleasures. The tug of the garter belt was delicious.

Her hands were suddenly on my panties — my panties — and I gasped. She was behind me, embracing me, pulling me against her. I could hear her breathing in my ear. Her mouth was close. Close enough to kiss me. Then she did, nipping at my earlobe as she pulled away.

"You're a perfect sissy in your panties," she whispered. "And now I'm going to break you."

Her voice was full and throaty. Her hands cascaded over my body, running down my naked chest and into my panties. She found my hot manhood and brushed the underside before pulling her hand back out, the fingers of her other wrapping around my satin-covered rear. My breathing was fast, my body loose. My manhood strained against my panties. I felt teeth sink into my shoulder, bright pain mixing with the pleasure.

"'Break' me?" I asked as a flicker of scorn flashed through me, drawing me out of the moment.

I do the breaking.

"Yes, Michael. I'm going to turn you into the sissy you've always wanted to be," she answered, hands sliding off my body.

I turned to face her, the sensation of my lingerie still sending goosebumps across my skin.

"How do you know what I've wanted to be?" I asked, eyes narrowing.

She met my eyes with a look like steel. "I've met a hundred boys like you, Michael. Deep down, every one of you is the same. You're all looking for something you want but won't let yourself have."

"I just take whatever I want."

"If that was the case, you wouldn't be here."

"I got caught what I wanted. That's exactly why I'm stuck here," I spat, feeling my arousal being replaced with anger.

"You can't take what I'm giving you, Michael. You can only be given it. Only a lucky few ever find it on their own," she said, her voice firm, arms crossed.

She took a step away from me, the gap between us swirling with the fresh spring air.

"What do you think you can give me?" I asked, voice rising.

Who does she think she is? She thinks she knows me better than I know myself?

My heart was pounding now. I could feel the anger rising in my chest like it always did, flooding my body.

Is this really what you want to happen? I asked myself, knowing my rage was almost out of my control.

Saskia stared at me for a long time before she finally uncrossed her arms and closed the space between us. She reached out to take my arm but I pulled away from her in a jerky recoil. I stared at the floor. After a moment's hesitation with her arm still outstretched, she reached for me again, and this time I let her touch me.

The warmth of her hand made my breath catch in my throat.

"Permission," she said softly, taking my other hand in hers. "I can give you permission."

"Permission?" I asked, the anger suddenly melting away. "Permission to do what? Put on panties?"

"No," she continued, her voice barely above a whisper now. "Permission to let go. To have the freedom to stop being what you think you're supposed to be. Now you can just be what you are. "

I finally managed to look at her. I was surprised to find her smiling. Her soft lips curved and made her face glow. I hadn't let myself notice it before, but she was beautiful in a hard-edged way, her sharp angles worn down but not gone. Her eyes shone in the dimming afternoon sunlight.

"Would you like to finish getting dressed now?"

The dress was heavier than I expected. Saskia zipped me into it from behind, sealing me within its satin confines. It pressed gently against me, the satin lining gliding over my naked skin as it settled into place. The lace trim of the neckline tickled my collarbone and chin.

It made my heart stop to wear it. I was desperate for a mirror, but Saskia insisted I wait.

The petticoat came next; a cloud of silk layers that held my ruffled pink skirt aloft and threw it outwards at a flat angle away from my body. Saskia tightened the thick ribbon around my waist, adding the weight of the garment to that of my dress. I bounced experimentally, feeling the heft and swing of the clothes around me. My hips began to wiggle of their own accord and I reveled in the feeling of the satin and silk spraying out around me.

Saskia directed me to the vanity and started on my make-up. I slipped my feet into the heels while she worked, tapping my toes. Finally, she told me to stop, the eyeliner pencil perilously close to my eyes. I breathed in slowly to calm myself. All I could smell were lilies.

And buried beneath layers of silk and lace and satin, my manhood tented my pink panties.

Finally, she closed the door, revealing a full-length mirror. She helped me walk to it. I teetered in my heels across the floor. I knew they were short and found myself hoping that one day I'd have the skills for taller ones. Hoping, in the part of myself I had always blocked out, that soon I'd be just as capable in heels as flats. And that Saskia would be there to see it.

I looked in the mirror. The girl who looked back was not me. Couldn't be me. She stood in my place next to Saskia, towering over the tiny woman. The girl's face was smooth and rosy, lips glossy and pink. The haircut was boyish in a sweet way, a charming contrast to the brilliantly feminine clothes she wore.

Slowly, as I bounced and twirled in the mirror, my brain reconciled what it saw with who I was. That wasn't Michael anymore — he was someone else. The girl in the mirror began to turn into who she was: me.

"You look absolutely gorgeous," Saskia said proudly, taking my hand and squeezing it. "You'll fit in perfectly here. This is right where you belong."

Her hand was suddenly on the back of my thigh, her fingers slipping between my legs. Her nails glided across my silk stockings until they found naked skin. I moaned as they followed the line of my garter strap upwards, disappearing into the froth of lace. I turned to face her. Another hand slipped under my dress, finding the waistband of my panties and pulling them down just far enough to free my raging erection.

"I love seeing how excited a sissy gets from her all pretty clothes," she said quietly as she began to stroke me. "All it takes is a pair of panties and you turn into a horny mess."

As she stroked, the lace trim of the petticoat brushed my shaft. The taffeta silk layers rustled as her hand moved. The curtains flapped in the breeze behind us, the smell of flowers filling the tiny space between us. She swirled her finger under the tip of my shaft and I felt a shock of pleasure burst out from me.

"Does that mean more panties?" I managed with a drunken half-smile on my face.

She let out a sound halfway between a snort and a laugh. "Oh yes. You'll have plenty of panties. And dresses, and beautiful things you don't even know about yet."

"I want to learn about them," I sighed, imagining sheer gowns and silky nighties.

"You will. But you might not like what you have to give up for them."

"Give up? What do I —"

"Hush," she silenced me with a finger to my lips. "You don't need to worry about that now. Just enjoy this."

Her hand returned, her motions changing, pulling pleasure out from deep inside of me. I shivered, my dress bouncing around me, the petticoat layers whispering sweet, silky things to me.

"Saskia, what do I have to do?" I managed.

"Are you sure you want to know?"

"I don't want to lose this, now that I finally have it."

"This is the last time you're going to cum for a long time," she whispered. "Let's make it count."

I could barely stand. I leaned against her, expecting her to collapse from my weight. She was a marble pillar of a woman instead. Her hands were exquisite, soft and smooth and constantly in motion. One traced a line around the waistband of my panties, pushing aside the lacy layers of my petticoat and finding my rear.

"What are you doing?" I gasped as a slim finger slipped down into the back of my panties, spreading my cheeks.

"Practice," she answered cryptically. "For when this is all you get to use."

I could barely think straight. Her words washed over me like waves, pulling me further and further out into her sea.

"Will it hurt?"

"Of course not," she whispered as her finger found its mark between my cheeks, pressing against, then into me.

I let out a low squeal that melted into a groan. My stomach clenched as sick pleasure radiated out from her finger. She traced it in tight circles while she stroked me, her hands now wrapping my manhood with my panties. The satin was slippery and sweet on my shaft. The pressure was mounting.

Then her finger slipped inside of me, barely past her nail. The sensation was electric and hot. My muscles tightened and I cried out. I came, hard, blasting jet after jet into the pink satin panties. She stroked me through it all, the slipperiness of the panties giving way to the hot stickiness of my cum. Somehow, feeling it there made it even better.

When I finally finished, I collapsed backwards onto the bed. My dress and petticoat settled around me in a tent of pink and white. The scent of lilies and grass blew against them, tickling the exposed skin above my stockings. I lay panting, recovering from it all.

"You said this was the last time I was going to cum," I said slowly, the memory of her words hazy. "Right? What does that mean?"

She settled primly on the other side of the bed, brushing her hair out of her face. I lolled my head to face her. She met my gaze over her shoulder, face stern. Her eyes searched mine.

"Do you know what a chastity cage is?"