My New Lady

The shower was running.

My boyfriend William came into the kitchen wearing only a towel around his narrow waist. He went to start a cup of coffee when I pounced. I seized him by the arms and yanked them back to his surprise, and cuffed them with leather cuffs as quickly as I could before he had a chance to fight back.

He yelped in surprise.

"What the hell --" he began, but I quickly shoved a big red ball gag into his pretty little gaped mouth, and secured it tightly behind his head -- shutting him up.

I ripped his towel off so that he stood naked in our little kitchenette.

He had no clue what was going on, but I had been planning this for some time now.

We were two young men living together, and often toyed with the idea of crossdressing for the sake of play, but never took the plunge.

This morning, however, I would turn him into my pretty little girl...

William struggled as I quickly buckled a stiff leather posture collar around his slender neck, and tightened it just enough to reassure him that any slight turn of the head would give him a good choking.

Once I had William just as I had wanted him, I pulled his head back by his pretty black locks, and whispered into his ear, "Today's the day I make you, my lady."

"Hmm?!" William mumbled, his confused whimpers like music to my ears, as if he suddenly realized who was in charge.

"You heard me. Now, c'mon," I said, spinning him helplessly around in my grip. "We need to get you nice and smooth. Let's go! Let's go!"

I spanked his plump little buttocks hard, and he winced and marched forward as I herded him around the corner toward our bathroom; his posture upright, back arched and facing forward as the collar kept his head from swiveling as the big red ball in his mouth was now causing some drool to roll down his chin.

In the bathroom shower cabinet, the running spray of water was now nice and hot...

"Get in," I ordered, holding William by his leather-bound arms for support as with some difficulty, he stepped into the shower and under the running water. The looks his eyes was delicious, as he had no idea where I was going with all of this, but I knew what I had in store for today.

I turned the shower head down, and stepped William out of range of its spray, and then I snatched up a bottle of Nair from the counter.

William's eyes widened at the sight of the bottle as I squirted an ample amount of hair removing cream into my greedy palm.

"Hold still," I warned my helpless little bound and gagged femboy, who obeyed without question.

Quickly, I began to lather William's neck and chest, then his back and his arms, and even under his armpits before moving south, down his rather feminine body, across his flat stomach until I reached around and swathed his plump rounded buttocks until he was thoroughly coated, and I needed another handful of the hair removing soap.

"Lift your legs," I ordered, and William raised his leg and planted his foot on the edge of the seat in the shower, letting his manhood dangle helpless and free.

I reached between his legs, and massaged the Nair into his tight little boy-hole. I wanted that area nice and smooth for what I had in mind. Satisfied it would be, I lathered more Nair all around his pretty balls and little cock, which I felt stiffening slightly as I roughly stroked and lathered him thoroughly.

I was smiling to myself, knowing that William was beginning to enjoy what was happening to him. And to be honest, my own cock was getting hard beneath my trousers.

Next, I took care of those pesky little pubes of his, soaping, and not missing an inch.

William's whimpers and moans, so befuddled and feminine, sounded sweet to my ears, and I could tell that he wanted to look down and see what was happening to him, but the posture caller choked, and prevented him from doing so.

Another helpless reminder, I grinned to myself.

Now, William's legs were long and shapely, but thankfully I had plenty of Nair to cover the slender stems all the way down to his dainty little feet, and baby toes.

I stepped back and ignored William's eyes like a nurse just doing her job, and began washing my hands in the sink.

"In a few minutes, I'll hose you down, and you'll have a smooth, girly little body for what I have in mind," I smiled.

After William was thoroughly washed, and I completely dried, I ushered him into our bedroom and pushed him back against the wall to marvel at my handy work; inspecting his pale, freshly shaven body, so long and lean with his wide ultra feminine hips.

To my approval, the only hair left on my sexy little femboy was the curly black locks on the top of his head. He had adorable little ringlets of black hair that reminded me of Elijah Wood in the Lord of the Rings films, a tad longer though, like a young prince, with curls that framed his round, agile face, accentuating and illuminating his soft green eyes blazing at me with wonderfully docile bewilderment; so innocent and delicious to me.

I saw that, despite how hard he tried to conceal it, William's cock had firmly erected to a girthy rod no thicker than a carrot and no longer than a middle finger, and he was helpless to hide it with his elbows secured together behind his back.

"Before I began phase two," I smiled. "I'll have to take care of that now, won't I?" I said, indicating William's rigid cock.

By the look on William's face, he hardly understood what I meant, but soon realized it clearly when I got down on my knees and covered his girthy member with my wet lips and began to suck and swallow, engorging my tight throat, smelling the lavender scent wafting from his freshly smoothed skin.

William's knees buckled slightly, feeling my warm mouth over enveloping his cock, and I had to hold him up with two hands wrapped around his hips, gripping those two plump cheeks of his, squeezing the juicy flesh and pulling him forward, forcing his cock deep into my mouth as I did my job with thorough indulgence.

Soon, William's muffled grunts and moans behind the big red ball filled the room as he fired off a few rounds of scalding issue down my throat of which I gulped and swallowed until his balls were emptied, and his cock shrank within my mouth.

From on my knees, I peered up at William, licking the runaway come on my chin, and said, "There, that's better."

At once, I brought from trouser pocket a shiny new metal cock cage, and without hesitating I fastened it around William's limp cock, stuffing him inside and locking it firmly in place with a mini-padlock to ensure that it could never be taken off without my permission.

Now, William's eyes really bulged, as he realized the reason I allowed his cock and balls to be relieved and drained. Honestly, I thought I was doing him the favor; but truthfully within my trousers my own cock was as hard as a rock, pushing and dripping against my tight Jockey's...

"A perfect fit," I mocked, rising and smiling at the stunned look on William's innocent face. "Now you won't be a naughty little girl, even against your own will."

William moaned behind the gag at me, and I kissed him on the drool covered ball and said, "Don't worry, my sweet boy. There's more to come. Come here."

I tugged William forward, and laid him face down on our bed. "Spread your legs," I said, and without delay William spread those long shapely shaven legs for me.

His cheeks were so plump and luscious that they barely spread enough to expose to me that smooth pink little boy-hole of his...

"Wider," I said, and William obeyed, struggling to stretch himself even further.

"Perfect," I giggled, finally getting a chance to see his wonderfully smooth boy-hole, so cute and tight and ready to be plugged.

"Stay just like that," I said as I turned, and I strode to our closet where I extracted a small carry-on suitcase, and laid it on our bed so that William could see it plainly. He eyed it and me curiously as I opened it, and revealed to him the secret contents that I had kept waiting for him inside. William was more than surprised.

"These I bought just for you, my little femboy," I said as one by one I showed William each item within.

I showed him the phallic leather plug with a long tube and squeeze pump attached to the end that was going to fill and widen his tight little boy-hole.

I showed him the tall, yet manageable, four-inch black patent leather heels with locking ankle straps that were just his size; that he would soon enough be forced to parade around on.

I showed him the black make-up kit I bought to feminize his pretty little face into a perfect little goth girl with when the time came.

I showed him the black leather corset, with four garter straps attached, and the packet of ash-black fully-fashioned stockings that he would wear beneath his girly gothic clothes.

"You see where I'm going with this, my sweet boy, William?" I asked with a sly smirk.

Helplessly, William peered from the collection I had gathered for him for this special day to me with eyes that to me looked scared, but in many ways appeared ever so curious for this to happen.

With drooling dripping over his chin, and choking himself slightly, William nodded yes.

"Good, now let's started."

I slid off our bed, and came around behind William. He couldn't turn his head to see me as I opened our night stand drawer, and took out a bottle of quality lube we use play with. I squirted a good amount into my hand, and I know William heard that familiar sound as his head perked up, and he whimpered knowingly.

I reached over his shoulder, and I know his eyes followed me as I grabbed the butt plug with the pump from the suitcase.

Lathering and massaging his tiny boy-hole with lube was hardening my cock in my trousers, and right then and there I thought to unleash my erection, and give the defenseless boy-hole a thorough fucking, but I had to resist the temptation, and avoid spoiling the fun.

Instead, I slid my fingers, one, then two, then three, into the tight little sphincter, listening to William's moans heighten as I coaxed and readied him the plug.

I lubed the plug generously, and gently slid the three-inch shaft with relative ease into the beautiful boy-hole until it vanished inside and the rubber stopper was all that I could see.

William winced, but accepted the plug with little resistance. Though only his elbows were secured together, and his forearms and hands were free to roam, William did nothing to protest.

"Beautiful," I said, proud of the obedient little femboy. "Now get ready, and don't tense up, because I'm going to give you a few pumps."

William spoke, mumbled really, but I only heard something like indiscernible garble, and spittle.

I squeezed the pump several times, and I could imagine that now inside of William's rectum the plug inflating and swelling to three times its size, about the size of a small avocado, stretching that tiny hole nice and wide and filling William up from within.

William's hisses and moans sounded to me as if the engorged phallus shocked and took his breath away, but then quickly abated, and were at once replaced with the sounds of sensations and titillation now surging through his quivering body.

"Moving on," I said, spanking each rounded fleshy cheek to hear William squeal in surprise as his body trembled and jiggled.

I lifted William up onto his feet, holding him upright as I turned him around to face me.

The sweet boy's face was a mixture of pain and pleasure, and his beautiful green eyes twinkled as his long dark lashes batted at me, as if he was beginning to relish his predicament, and wonder what else I had in store for him this morning. His posture collar kept him forward and attentive, and his elbows leather cuffed behind his back jutted his chest forward, and arched his feminine back.

"First, the corset," I said, taking the leather corset from the suitcase and holding it up in front of William. It was the type that used clasped in the front instead of lacing in the back, and based on William's naturally feminine form I knew that a size small would cinch his narrow waist just tight enough to give him that hour-glass shape.

And it did. Once fitted, and clasped, his femboy body took on a truly womanly figure.

William breathing became labored, and more drool spilled from the big red ball, but cruelly I knew he would just have to get used to it...

"Next, the stockings," I said, taking out a fresh packet from the suitcase. "These are fully-fashioned," I said, "And very delicate, so I want you to be very careful when you're moving around in them, is that understood?"

William nodded once to avoid choking himself.

"Good girl," I smiled. "Now sit," I commanded, and William, although slowly, took a seat on the edge of our bed and I could tell by the squinting in his beautiful eyes that by sitting down on his bottom the inflated plug burrowed itself a little further up that narrow little rectum of his.

Nevertheless, I smiled, and slit open the packet of fully fashioned stockings, and delicately removed them, and with much care, I slid each soft, weightless stocking up William's long, smooth legs, aligning the seams, until I settled the wide welts high on his womanly thighs. I attached the welts to the frontside clasps first, then ordered William rise and hold still as I attached the stockings in the back.

I stood back, full of glee.

The picture was coming together now.

William's body looked amazing in the tight corset, and the stockings were perfect in the way the shadows accentuated the contours of his legs, defining his calves and thighs wonderfully. He looked remarkably natural embellished this way, and I knew by the drips seeping from his stringent cock cage that William was loving the way the nylon felt against his skin.

"Perfect," I said, admiring my handy work. "Now, sit back down -- carefully!" I reminded.

William did as he was told, drool dribbling from ball gagged mouth; his eyes doleful and full of wonder at this new feeling.

"Now," I continued. "The heels."

I reached into the suitcase, and took out the four inch heels, then bent to one knee, and fit the shoes with Cinderella perfection onto each of William's dainty little feet, adjusting the wide leather ankle straps snugly, and locking them on with a mini-padlock, which meant the heels could not be kicked off, or removed no matter what, I grinned.

"Now, stand up," I said.

William, with some difficulty, rose onto the four-inch heels and at once began to wobble like a baby deer until he found his balance and straightened his posture, accentuating the soft muscles in his legs, jutting his chest forward, increasing the arch in his back...

"So beautiful," I smiled with approval. "Now, let's see how fast you can learn to walk in these heels," I said. Come with me."

William followed me out of our bedroom, down the hall and into the living room where I set up a treadmill for training. I arranged the treadmill to face the window so that William trained he could watch the city, with all its pedestrians and cars roaming about below, unbeknownst there was a helpless femboy in training inside of our apartment.

I peered back, and saw that with each step in the tall, yet manageable heels, William tittered and wobbled until his feminine hips found their fluidity, and his gait in the heels seemed to come natural to him, which I had a feeling his feminine hips would. And he hardly seemed to mind the plump plug stretching his boy-hole...

"You're a natural," I said as I guided William to the treadmill. "You're going to practice from me for a little while until I can get everything ready for the next phase of your feminization. Is that understood?"

William nodded that it was, and without hesitation, I noticed.

Either he was really enjoying being feminized, or maybe he just realized that he really had no say whatsoever. Nevertheless, it aroused me to think of both, but the stiff cock in my trousers, which I knew by now had soaked my Jockey's, found the latter far more titillating.

"Hopefully no one below will see you, but that's not our choice, is it?"

William shook his head in agreement.

"Good. Now step up."

William stepped carefully onto the treadmill.

"Now," I began, "For this exercise, I wanted to add an element of danger that will instill within you just how crucial it is to learn how to walk in heels without fault. All feminized boys must learn to master this skill," I said. "Understood?"

William nodded that it was.

"Good. Now give me your wrists."

William's eyes bulged.

"Now," I said, spanking his plump rounded cheeks so hard that the smooth pale skin reddened slightly.

The little femboy let out a girly squeal, and jiggled, but then at once obeyed, bringing his palms together behind his back. I quickly belted them together, and then turned the treadmill on at a slow pace.

The runway began to cycle, and William had no choice but to step forward, and keep his stride as even as possible as the moving track simulated a real-life catwalk.

"Good, girl," I said with a smile. "I'll be back in a few minutes, and don't worry, I won't leave you for very. I'll just be -" but, I stopped, realizing that William was far too focused, and determined to learn that I don't even think he heard me.

Before I left the room, I paused and looked back at William, strutting with ease in the four-inch heels, his long legs defined so wonderfully in the fully fashioned stockings, the seams lined up perfectly, and his plump buttocks jiggling back and forth with each step as the tube from the plug in his pretty little boy-hole dangled and whipped to and fro...

My cock was rock hard in my trousers, and once again I thought about unleashing it and accelerating my little game. I had a ring gag in the suitcase that would stretch William's big wet mouth perfectly wide enough for me to face fuck him for a good time until I pulled that plug out of his tender tush and ravished him roughly until I filled his gaped hole with my filthy hot issue...

Shit! I thought. That has to wait, plus I had more feminizing to do. I squeezed my cock, and shook the naughty thoughts from my mind and refocused on the task at hand.

After about twenty minutes, I returned to William who by now was exhausted and moaning.

I noticed outside of the window that a few bystanders below had stopped, and where filming William from the sidewalk with their phones.

I giggled and waved to them, as if to say the show was over, before I switched off the treadmill, and helped William down. His legs trembled as I walked him into the kitchen where I arranged a wooden chair in front of a well-lit vanity mirror.

William stopped short when he saw that fixed in the middle of the wooden chair was a decent sized rubber cock, ribbed with tiny rubber knobs, and shimmering with lube, just waiting for him to sit on.

"That's right," I whispered into his ear. "Now that your little boy-hole has been good and stretched, I thought his might suit you a little better while I doll up that pretty little face of yours."

William's girly little moans were a combination of fear and intrigue.

"Now, let's get that little boy-hole of yours ready."

I pressed William face forward against the wall, and twisted the valve on the pump to deflate the plug inside of that tight hole of his, then pulled the plug right out with a juicy wet little pop.

William breathed a sigh of relief, but he knew it would be short lived as I hustled over to the chair, aligned his gaping hole up with the ribbed rubber cock, about five inches in length, but thick, and placed him down easily so that the cock impaled him slowly until his plump fleshy cheeks touched the wooden chair, and he breathed in his new friend.

"There you go, my little girl. How does that feel, all nice and tight inside that pretty little hole of yours?"

William moaned, and whimpered, and try to say something like -- "Thank you."

I smiled, and then leaned over his shoulder, showing him a small remote I held in my hand.

"This playful cock comes with a little secret. Here, let me show you."

I pressed the ON button on the remote, and the cock burrowed inside of William came alive. His eyes closed and he groaned and wiggled as the vibrating sensations assaulting him inside immediately took over his labored breaths.

"Not bad is it," I smiled. "Now, for your make-up. I want you to be my little gothic femboy," I said. "But, first, let's get you nice and secured."

I lifted William's bound arms over the back of the chair, and tied his wrists to the frame so that he couldn't move. Then, I spread his legs wide, knowing the plug would drive a little deeper, and secured his ankles to the wooden legs of the chair.

By now William was moaning, and listless, and his head bobbed back and forth, and his cage was a mess of precum with sticky strings spilling onto the seat of the chair.

I left him a moment, and knew his eyes trailed me from behind as I exited the kitchen, and soon returned with the make-up kit, and began to lay everything I would need to doll this little sissy up out on the vanity table: mascara, dark eyeliner and eye shadow, black lipstick, fake black porcelain nails, fake eyelashes, and powder to whiten his pale skin even more, essentially everything it would take to feminize William in the cutest little gothic femboy.

"Ready to look beautiful?" I asked.

William nodded weakly, his head bobbing as the thick rubber cock inside of him vibrated and tormented him slowly. Based on his moans, I feared it was about to come. I took the remote and switched off the vibrations.

"No, no, no," I smiled, deviously. "You haven't earned it yet."

William groaned in frustration. He looked at me like I stole something from him. He knew he was so damn close.

"Stop that," I said. "It's time for your make over."

I reached around William's head to remove the big red ball gag.

"No talking once I remove the gag, or it goes right back in, and you go right back on the treadmill. Is that understood?"

William nodded, more than ready agree to those terms. His mouth by now must be sore anyhow, I figured, but realistically it had only been an hour since I captured and showered William. Gee, time was flying fast...

I removed the ball gag, and it dislodged from William's big mouth with a trail of drool spilling out at once. I wiped it clean with a towel. There was nothing I could do about the lines from the ball gag strap across his cheeks, but that wouldn't affect the make-up process.

The posture collar I kept on for good measure.

"Now, hold still," I said.

Within twenty minutes, I had feminized William into a sexy little gothic girl, with pale skin and plump black lips, dark and shadowy green eyes, black nails and dark locks that I parted and swept over his brow line, and adding a cute little black bow to the top of his head.

"You're ready for the next phase," I smiled at William.

"What's the next phase?" William asked, a tad timid and a little worried as to the next part of my playful little game.

"We're going to go out for brunch," I said. "To your favorite little café in old town."

"Wait, what?" William's gaped expression was priceless.

"You heard me," I said.

I untied William legs and released his arms; he took a deep breath before I lifted him off the thick cock in his tight boy-hole, then gasped in relief as I stood him upright onto his high heels.

I removed the posture collar, and said, "Follow me into the room so we can get you dressed."

"I love you, but you can't be serious," he moaned. "You're going to take me out in public like this? To my favorite spot?"

"Of course. No one's going to notice a thing. Besides, it's not as if you'll get hard or anything with your cock in that little cage."

"Yeah, but still. It seems a little over the top, doesn't it?"

"Look," I said, turning to William sternly. "You're my little femboy for the day, so you better get used to obeying my orders. Or would you rather me tie you to the treadmill, leave you here and go out to lunch by myself? I could be gone for hours..."

William sighed. "Fine. I'm your femboy, and I will obey you."

"Good girl." I gave his plump cheeks a little spanking, ushering him forward. "Now let's get you dressed."

For William's outfit to go over his corset and gartered stockings I chose something simple, yet adorable enough to give him that playful and rebellious gothic girl appeal.

It was a short black school girl pleated skirt that wasn't so short that it would expose the tops of his stockings, but just short enough that it would come so desperately close that any passerby would pray for a breeze.

For William's top, I chose a sheer nylon teddy that fit like a swimsuit, but had a lace embroidered turtle neck, and long nylon sleeves that covered his arms and hands, but were fingerless.

To my surprise, William actually found the found outfit quite stylish, and a little risqué to say the least. He began to dress when I stopped him, and said, "Wait just a minute. First, we have to plug up that little hole of yours. I want you teased and titillated the entire time we're out there in public."

William grinned. He loved it. "What do you have in mind this time?" He asked.

I smiled and showed him a hard black rubber plug that was as thick as an overgrown strawberry and one that I knew once inserted into that tight boy-hole properly would have no choice of slipping out.

William raised his brows at the sheer size of the plug, but by now I knew his tiny hole had been stretched and was well prepared for an upgraded plug.

"Bend over the bed," I said, already lubing up the frighteningly wide plug.

"Yes, sir," William said with a sly grin, planting his hands on the bed, and presenting his pretty plump cheeks to me. I saw that his once tight little boy-hole had indeed stretched to the size a small black cherry, which for William was a definite increase in size.

"Ooo, sir," I chuckled. "I like that. Very obedient. Now get ready."

The large plug seemed a bit challenging at first, but after twisting and pushing and using some force, William let a faint yelp, and the plug breeched and filled him up to the brim. And once this plug was in, I knew that it would never accidentally slip out.

"Fuck, that's huge," William breathed shakily. "Oh, my god. It's stretching me so wide. I feel like I'm taking a fat cock right now."

"Good," I whispered in William's ear. "Now, you can get dressed. Be careful with the teddy. It's delicate. I'll be waiting in the living room for you when you're all dressed up and ready to go."

"One thing," William said.

I turned to find him looking down at the locking high heels. "Do I have to wear the locking heels while I'm out?"

"Oh, you're right. I almost forgot." I went to the suitcase a took out a pair of black oxford loafers with four-inch heels and dainty laces up the front. "These ought to do," I said, handing them over to William. "They'll be easier to walk in, too."

William smiled, approvingly, and I left him to dress.

In the living room, I poured myself a drink at our bar, and thought about how I was going to control my own erection. In all honestly the beast beneath my trousers had been alive and tormenting me all morning ever since I bathed and smoothed out William at the start of my little game.

Oh, how I desperately wanted spill my hot creamy issue in that tight boy-hole of his, or down the slender throat of... Huh? I though. And right then and there, just like that, I had an idea of what I was going to do with that pretty little mouth of William's as soon as we were out in public, and possibly alone...

After a few minutes, and a second drink, William strutted gracefully into the living room. The oxford heels where much simpler to control, I noted, and I was floored by how cute and sexy he looked all dolled up with the dark makeup, the sweep of his bangs across his forehead, looking rather goth in the black schoolgirl skirt worn high on his waist with the nylon sleeved turtleneck top tucked in, and the oxford loafers accentuating the adorable and fallen school girl look.

I'm not sure where William got it, but he wore a black cross around his neck, laid over the sheer black nylon of his top perfectly in the middle of his chest.

"Turn around," I said, grinning, and William did as he was told, spinning around and facing the wall. "Lift your skirt," I said. He lifted the short skirt slowly to reveal the thong backed teddy bisecting his two juicy butt cheeks perfectly, the straps of the gartered corset crossing his pale buttocks, and the stopper of the great big plug just visible beneath the thin string of the thong.

"How does that plug feel?" I asked.

"It's feels huuuuge. Has me all filled up. Thank you, sir," William said.

"And the cage?"

"Tight and unfair," he complained. "I feel like I'm going to burst."

"Well, let's hope you keep it together long enough in public. We don't want to make a mess now, do we?"

"No, sir," William grinned. "We most certainly do not."

PAUSE

AUTHOR'S NOTE: This is starting to sound like some sort of dating story. I got way off track. Let me know in the comments what I should do to carry on with this story. In my mind it gets a little naughty yet maintains a sort of romantic fantasy played out by a loving couple.