Almost Every Inch a Woman

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I had my wrists in place and my head down in their places, ready to be locked in.

"He's very docile and obedient!" mentioned Sabrina.

"It's all in how you train them," chuckled my Mistress, and the three laughed.

Now, if I was going into the stocks, that meant they might attach a penis pump to me and allow me to cum! They dropped the top bar and locked it into place. I quivered as I felt the pump being attached to my prong. My heart rate rose, and my pulse skyrocketed as they turned the machine on. I quivered and quaked all over. I felt delicate hands caressing my ass and hips, then a she-prong being delivered into me. Again, I moaned, and the women giggled. The three of them took turns shoving their dildos into my open and gaping ass and I loved every minute of it after being conditioned to this for so long.

After the company had left, she took my head in her hand and pressed her lips to mine. "Perfect!" she beamed.

A few weeks later, the only part of my body I had to shave was my crotch, and breasts had begun to sprout. "Look at that," she beamed. They're beautiful, and what they do for your figure! All natural," she giggled. She took me out to find my first bra that same day. They progressed to B-cup before she cut back on my 'vitamins'.

One day, she came to me. "Justine, we need to get you dressed." She took me by the hand and led me into the bedroom where she picked a truly short, yellow skirt and matching top. She then walked into the lingerie and chose some white stockings, garter belt with rec accents, white garters and a matching bra. "Put this in," she commanded.

"Yes Mistress, "I answered as I began to put the garments on.

Next, she took me to her makeup table, and began to apply it to my face. The faded to intense blue eyeshadow she put on me really accentuated my eyes. This was her field, and she was a pro. Just enough blush and ruby red lipstick to go in my purse for touching up. She put fake red nails on me and then lastly, she styled my hair.

She brought me in front of the full-length mirror. "See how pretty you look?" she asked.

I had to admit, the gurl standing in the mirror would have attracted my attention in days gone by. I looked like a natural woman! "Yes Mistress," I automatically replied.

With her in a grey pantsuit, got into the car and got going. She drove across town to another high-rise building. She stopped, got out and consulted with the concierge, who proceeded to open the door and admit us. We rode the elevator all the way to the penthouse where we stepped out into an expansive foyer.

"Ah, come in, come in!" said a smiling voice as a man followed it around a curved wall and into the entryway.

"Hi Roger! How are you doing?" smiled my Mistress as a six foot two, two-hundred-and-twenty-pound man with dark hair and blue eyes dressed in beige pants, a white dress shirt and a beige cardigan thrown over his shoulder, appeared from around a curved corner.

"Annie! Great to see you again!" he exclaimed giving her a kiss on the cheek. "And who is this?" he asked looking at me

"This is Justine," replied my Mistress for me. "Justine, this is Roger Brandt." At this point, I had no idea what to expect. Was she going to cuckold me with him, too?

He took my hand and kissed it, just as I had done with Annie's hand so long ago. "Pleased to meet you, Justine," he said solemnly as he kissed my fingers. I felt it rather charming.

She gave him a key to my chastity cage. "He is now your keyholder," she stated. "You do whatever he says.

"Yes Mistress," I submissively replied.

"Okay, I have to go and get a few things done," she announced as she headed for the door. "You two get acquainted and I'll be back in a few hours to pick him up."

I looked at him and suddenly understood why I was all dressed and made up. I was to be a two hour treat for him.

"You are gorgeous, you know?" he asked as he closed in for a taste of my soft and willing lips.

"Thank you, Sir," I fluttered.

He took me into his arms and continued to probe my mouth with no complaint from me. "Let's continued this discussion in my bedroom, okay?" I followed him in where he began to strip me out of my outfit, an endeavour I eagerly participated in.

He let out a low gasp when he saw me standing in front of him with just the lingerie on and my caged cock hanging below. "You have got to be the most beautiful T-gurl I have ever had the pleasure to meet."

"Thank you, Sir," I blushed.

He took the key out, unlocked my cage and set it aside for future use. "Bet that feels better, eh?" he smiled.

"Yes Sir," I replied. "I had been in it for just over two weeks since my mistress had unlocked it for me last time. I think she was saving me for you."

"Oh, goodie!" he grinned as he put his hands on my shoulders and pressed me to my knees then snapped a leash to my ever-present collar. "Undo my pants and take them off," he commanded.

"Yes sir," I replied unbuckling his belt and the button of his pants. His eight-inch-long member was separated from my watering mouth by a thin strip of cloth. He whisked away the cloth revealing his wonderful cock to me in all its glory. "What do you think of that, Justine?

I stroked his magnificent manhood, entranced by his length and girth. "It's magnificent, Sir!" I quietly exclaimed. "Truly extraordinary... Sir"

"What do you want to do with that?" he asked as he angled his waist toward me.

I looked up at him with smouldering eyes as said, "First I want to kiss it," I leaned forward caressing his cock with the softness of my lips. "Then, I want to lick," then licked his wonderful cock. By the time my lips were at the tip of his prong his hands were on my head, ready to guide me, and guide me he did. His fingers entwined in my hair and told me exactly what to do as my mouth rode up and down his prong and a half. I swirled my tongue on the underside as he passed in and out.

His huge head brushed the back of my throat. It was one of the single most glorious feelings that I had ever had. I realized now why I had never had a lot of success dating women. I was meant to be one and my Mistress had teased out the T-gurl in me.

After an eternity of time passed, I felt his body stiffen and his cock pulse as he released precum into my mouth. I realized his orgasm was imminent. The thought horrified me for a moment, but then, I had been cleaning other men's cum out of my Mistresses pussy for months and relaxed.

He held my mouth exactly where he wanted it as he began to shoot great blasts of cum into my mouth. I tried to keep up with it, but it overflowed my mouth at the corners.

"How long has it been for you, Justine?" he asked.

"I told you that I've been locked up in chastity these past two weeks, and not allowed to cum at all, Sir." I answered.

"No, no," said Roger. "How long has it been since you last got a blowjob?"

I thought for a moment before answering, "I can't recall, Sir."

"Really?" he asked as he placed his hands under my arms, hoisted me off my feet and threw me over his shoulder as I giggled and shrieked. "We shall have to remedy that then, won't we?"

The journey ended when he threw me onto his huge bed and watches as I bounced to a stop with lust in his eyes. I looked up at him demurely as he crawled up my body to take my entire small, soft dick into his mouth at once.

"Ahh, Justine!" he erupted. "I love your little cock! Always nice and soft. You can't get hard anymore, can you, Baby?" he asked. "Your Mistress kept you in chastity for that long?"

"No Sir. Thank you, Sir,"" I beamed, albeit a little flummoxed. "I don't fuck that way anymore, either." He went back down on my tiny body in earnest, tickling my head and stimulating me. He sucked my little cock in and out of his mouth, licking the head of my cock as it came by the tip of his tongue. I blew a huge load into his mouth, moaning and crying in pleasure as he finished me off. His was the first mouth I had cum into in an exceedingly long time.

He rolled off me, crawled up and took me into his arms, cuddling me close to his manly chest. I melted into him.

Again, he got restless. He stood up at the edge of the bed while I lay on top of it and jacked into my waiting mouth until he was hard as a rock again. He then took me by the hand and led me out to the kitchen table. I looked at him with a quizzical look on my face, so he grabbed both my wrists in one massive paw, dragging me over the surface. God, you look so good like that!" he exclaimed as he pushed easily into my well-prepared ass.

He hammered into my ass as I huffed for breath, each one accompanied by moans and cries of pleasure. He grabbed my arms and held them behind me to ach my back as he ploughed his huge cock into my gaping ass. He grabbed me by the hair and walked me over to a counter which he bent me over and lifted my leg to continue ploughing into my wanting and waiting hole. I was moaning like the whore I knew I was, but his cock breeding me felt so good, I couldn't help it.

From there, we moved to the back of his huge couch, which he threw me over and slammed into my ass, causing me to moan like a bitch in heat. "You like that, do ya?" he asked.

"Y-yes, S-sir," I said haltingly as explosions took place all over my system and I started cumming spontaneously through his thorough pounding of my ass.

"Good," he grunted as he penetrated me again and again. I was ready, open and waiting for him hen he began to pick up the tempo.

"Are you a slut?" he asked in bass tones as his magnificent pecker penetrated me to its deepest point.

"Yes Sir," I said meekly.

"'Yes Sir,' what?" he growled.

"Yes Sir. I am a slut, Sir," I whimpered as he forced the words out of me.

"Mmm, love to hear that coming from your sweet mouth, Justine," he replied. Little whore for your Mistress?" he asked.

"Yes Sir," I answered in chopped words as his cock blew away any chance at rational thought. Roger got really excited after my admission and began ploughing me like a freight train in heat. I was moaning and crying with pleasure as his fingers clutched as my ass as his hips pumped his prong in and out of my puckered ass.

I felt him strike bottom him and stiffen. His orgasm was a few strokes from happening and I was looking forward to an ass full of cum from this gorgeous man. He blew his load deep inside my ass. I felt the liquid splash and jump inside me making me quiver and squeal in pleasure.

We lay there with one another, spent, for a time. Then we got up and began getting dressed.

In time, the intercom buzzed to let us know that my Mistress had arrived. He tucked my cock back into its cage for me and locked it up and I got dressed in the scanty clothes I wore.

She arrived out of the elevator and eyed the two of us smiling. "How'd it go," she asked.

"Great," said Roger. "Can't wait to have him again!" he smiled, winking at me while handing my mistress a wad of bills.

"We can work something out," she said idly as she counted the money. Finally, she said, "It's been a business doing pleasure with you," smiled, then turned to leave.

"There's a whole lot of girl in that boy of yours," stated Roger.

"Oh, I know!" smiled my Mistress over her shoulder as I fell step at my place, two feet behind her. "Almost every inch a woman," she laughed.

This scene was to repeat itself over and over. My Mistress would dress me up in some slutty outfit then leave me with a stranger to satisfy only to return for payment. Thus, I became her new source of money. Soon I was getting fucked up to four times daily, five days a week, and then special events on the weekend.

Her plan had come to fruition. I was now the happy slave slut for my beloved Mistress, which is exactly what she wanted when this all began. She had chosen me as her prey, stalked me, caught me and then moved in for the kill with the precision and grace of an eagle on the wing. I was happier than I've ever been, and I'd have done absolutely anything for her. She had me for life, and she knew it and, if she hadn't died, I'd still be with her.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
6 Comments
88girfriend88girfriendabout 1 year ago

I loved the slow progression as Justin turned into Justine. His fall was slow but oh so satisfying. Clap clap clap. 👏

SDRogersSDRogersover 1 year ago

Well written and a beautiful turn of managed language. It is rare to find an author of this caliber online. Exceptional work. I'd love to meet the creator of this golden piece.

petey377petey377over 2 years ago

your stories are amazing & hot!!!!! i love how his mistress slowly brings out justine

petey377petey377over 2 years ago

another wonderful story

AnonymousAnonymousalmost 3 years ago

You are an ingenious author who perfectly mastered words and plots! But we were waiting for the continuation of the story of two dancing couples who will finally seduce the third!

Show More
Share this Story

Similar Stories

Her Presents She had a number of surprises for him.in Fetish
Sissification 101: Ch. 01 Straight guy is caught watching sissy porn and…in Fetish
My New Job A college kid undergoes a transformation at his new job.in Transgender & Crossdressers
Five A middle aged man explores his submissive fantasies.in BDSM
Locked Out of Apartment The sexy neighbor girls have a surprise.in Transgender & Crossdressers
More Stories