tagTransgender & CrossdressersPretty in White Ch. 01

Pretty in White Ch. 01


Pretty in white...

That's what my Mistress whispered in my ear after she finished dressing me in a white bra, a white knit camisole, a white linen blouse, white sheer pantyhose, and the palest-of-pink panties over them. She stood me in front of her full-length mirror in her dressing room, and she came up behind me. I was wearing white open toe sandals with four-inch heels. I wondered why she had chosen white for me, but I knew better than to ask.

I had already bathed, and I made sure there wasn't the faintest trace of body hair anywhere. There rarely was anymore after nearly a year of hormone therapy and electrolysis treatments. And of course, as my Mistress always demanded before I bathed for one our sessions, I gave myself an enema just as she had shown me and so I was squeaky clean inside and out. After lingering for an hour over my eyeliner, mascara, foundation, blush, and lipstick, everything was perfect. To my delight at the last moment my Mistress handed me a pair of small hoop earrings to wear.

Earlier in the day, I had my hair done so the last thing I wanted from my Mistress was criticism about my makeup and hair.

When she saw me, she brushed my hair back as she whispered about how pretty I looked and probed my ear with the tip of her tongue. Breathlessly, I watched our reflection in the mirror, and I again saw how she was the most beautiful woman I had ever known. Taller than me by a several inches, Mistress had a complexion of perfectly alabaster skin, like fine Chinese porcelain, coupled with along raven mane of hair. Today she was dressed in a tight pair of beige twill jodhpurs with a cream-colored silk charmeuse blouse unbuttoned just enough to reveal the swell of her gorgeous breasts. Her riding britches were tucked at her knees into a pair of black patent leather boots with five-inch stiletto heels. It only added to her beauty to smell her intoxicating, one-of-kind, Swiss perfume.

I was in a state of utter intoxication with her beauty, as she slipped her left hand down under my pantyhose and then my panties. I flinched slightly; she worked my testicles up inside of me pushing my semi erect penis between my legs and smartly tugging the back of my panties and pantyhose upwards to trap my cock. Even though I'd felt her do this before, I still gasped at her touching my maleness and as I leaned back into her, a moan escaped my glossy pink lips.

"Shhh!" she commanded as I naturally shifted my weight from one foot to the other trying to rub my confined penis between my thighs. Knowing she didn't want me to have pleasure now, I saw her smile deviously and then she pinched my ass real hard. "Stop that, or I'll lock you back up." Just as she knew I would, I stopped immediately under the threat of being returned to the hateful chastity device she made me wear most of the time.

Despite what others may think, I love wearing pretty clothes especially when my Mistress chooses them for me and it's even better when she takes the time to dress me in them. There's no better feeling than rubbing my thighs together when I am wearing sheer stockings held up by suspenders, or the wonderful feeling of soft silk panties on my ass and cock. I try to be the prettiest girl that I can be, but all of it comes at a cost. For nearly a year, I've been in the care of my Mistress who can be extremely demanding. Being her girl requires the utmost attention to details and unquestioning devotion to her, a fact that my Mistress constantly reminds me. To help me achieve the goal of perfect femininity, she locks my cock and balls up in a variety of different chastity devices for days or weeks at a time. This means, like almost every decision in my life, my Mistress controls when I can cum as a male. Before I came under my Mistress's care, I was a habitual masturbator, wasting time and energy jerking off three or four times a day, but now I climax only when Mistress allows which is up to her and a subject of great anxiety for me.

At first, I was distressed about my lack of control orgasms, but Mistress wisely pointed out how much better my climaxes are now. "Did you ever explode like you do now when you jerked off five times a day? No, by denying you I've made your orgasms much better. You should thank me."

It didn't take me long to realize, she was right and she clearly knew the power that orgasm denial has over submissive males like me. To be truthful, some of things she's made me do over the past ten months have left me shaking my head in total disbelief and I understand now how there's a lot more to being her girl than dressing up and being pretty.

Right before we left her dressing room, she reached into a drawer and pulled out a pair of white satin opera gloves. She told me stick out my hands and she pushed them all the way up to my elbows which of course obscured my perfect nails. "I'm sure you'd love to touch your little clitty with these on, wouldn't you, but you know what will happen if you do, don't you?" She smirked, but she was completely right, I did know the sort of punishment which would ensue if I jerked off with the satin gloves on.

She led me out of her dressing room and downstairs by my gloved hand into her large photo studio where, to my surprise, three of her friends were waiting. Shocked and more than a little afraid, I put my eyes to the floor as I wondered what was about to happen as my impression had been this was going to be a private photo session with just my Mistress and me. Amongst her other achievements, my Mistress was an internationally known professional photographer. In the past year, I had become a constant subject in front of her cameras; and she had splashed images of me on the Internet in all sorts of poses; many of which were extremely provocative, lewd, and even downright hard core pornographic.

Mistress took my hand and led me past her friends as if she was showing off my utterly feminized body.

"Oh, she looks like a perfect little virgin," One of her friends exclaimed.

"Really, well I guess that shows you can't tell a book by its cover," replied my Mistress with a sly smile.

Mistress ended her show of my body by bringing me to the one friend I recognized, a Miss Patrice who I'd had a previous experience with. Once, about a month or so ago, she had quite eagerly spanked my panty clad ass with a hair brush as I lay across her lap. Once my bottom was tenderized, she flipped me over and dumped me unceremoniously onto the floor. Then she stood up, hiked up her skirt and bared her shaven pussy to me as she squatted down on top of me. Miss Patrice rode my face until she came, gushing her juices all over me as my Mistress applauded her efforts.

At that point, I had thought the experience over, but I was all too wrong. Miss Patrice returned to the hairbrush and yanked my panties down to expose my very erect penis. She then asked if I wanted to come, but I looked at Mistress knowing that was her decision.

"You may force her if you wish." Mistress replied and her words seemed cold and unfeeling to me.

While pushing my erection down in the direction of my feet, Miss Patrice began to vigorously rub the shaft of my swollen cock and balls with it. Then she began to slap my helpless flesh with the sharp bristles of the brush.

It was hard to believe she wanted me to climax under these conditions and I started kicking my legs and screaming for her to stop while I looked pleadingly at my Mistress. However Mistress simply observed me being ravaged and soon I was writhing in pain, but I tried not to cry.

"Well, why don't you cum?" Miss Patrice screamed at me. "Don't you want to get off? How long has it been since your last orgasm, you little slut?"

Finally, after what seemed like an eternity, my Mistress spoke. "She can't cum, Pattie, as long as you're holding her little clitty down. Males can't ejaculate from that position. If you do really want her to cum, let her thingy up."

Miss Patrice looked up at my Mistress. "Do you want her to cum? I don't really care if she does or not." She laughed as she released my erection.

"Well then, stop torturing her and leave something of her little clitty for another day." Mistress stated making me happy the torturous hairbrush ordeal was over.

It was then that I realized Miss Patrice was mostly motivated by raw sadism, as the sight of my very red, raw, and now flaccid penis provoked a final comment. "You may not need a chastity for her now. I'm guessing she won't want to touch herself anytime soon."

Needless to say, this was why the sight of Miss Patrice in the studio gave me a sick, queasy feeling in the pit of my stomach. Apparently, Mistress noticed my look of anxiety at Miss Patrice.

"Look, Patti, my little slut is terrified of you."

"As well she should be, but don't worry, sweetie, I'm not playing with you today, or at least not right now." Patrice's response made a lot of tension leave my body.

Mistress led me over to a divan in the center of the large, high ceiling studio, where she told me to lie down. After arranging several light stands with soft, light bank strobes, she started taking pictures of me and soon I could feel my trapped cock hardening as it fought to come forward and become erect.

After several minutes of pictures, another woman came forward. Taller and thinner than Mistress, she towered over me and she wore tight, black leather pants with a blue sleeveless T shirt and four-inch heels. Her reddish blonde hair was cut short and parted to the left side, but she was not excessively made up as her high cheek-boned face had just some eyeliner and lipstick.

"May I check her out?" she asked my Mistress.

"But, of course, Wendy", my Mistress replied as if she were eager to watch.

Miss Wendy brushed her hand over my bra and gave my breast forms a firm squeeze. "She still has fake tits, I'd thought you'd have gotten her real tits by now."

"No, not for another six months or so. She's been on a hormone regiment now for months and you know how long it takes to totally take hold. I want her to grow some small ones before I make them bigger", Mistress replied in a somewhat bemused voice.

Miss Wendy now trailed her fingers down my flat belly to my panties where she began exploring between my legs. "Spread, bitch!"

At her command I spread my legs allowing her complete access. Soon I felt her hand grab my growing erection, which was both embarrassing and not allowed without Mistress' permission.

"Oh, she's getting hard. The little pee-pee wants to come forward and show. She really is a slut." Wendy emphasized her point by rubbing the tip of my trapped penis with her fingers, which only increased my desire and I became worried I'd get pre-cum and stain my panties.

At this point my face felt hot and my throat was dry, but things got even scarier when I heard the sound of a zipper. My eyes must have widened in sheer terror as out of Miss Wendy's black leather jeans tumbled a huge strap-on. Somehow, I had missed the bulge in her jeans before, but this flesh-toned latex cock was the largest strap-on I had ever seen, perhaps twelve inches long two inches in diameter.

I knew immediately what was to happen and I was stunned. Oh god, there's no way I can take something that big. Mistress won't make me, will she? Truthfully I didn't know, but every muscle in my body wanted to flee, to run out of the studio and hide, but I knew the consequences if I did such a thing.

Miss Wendy stood over me pumping her hips suggestively to make the monstrous phallus wiggle and sway before my disbelieving eyes.

"Cat got your tongue, sweetie?" Wendy purred. "Don't try to tell me you've never seen a cock up close before, not a little sissy slut like you."

"Uh, uh, no...I mean yes. It's just, well, I've never seen one this big before," I stammered hoping to be saved from Miss Wendy's jutting erection.

"Well then, how about you crawl down here and take it in your mouth, bitch." Miss Wendy glanced over at my Mistress to see if this was okay with her.

Nervously, I also looked to my Mistress, but my hope was for some kind of reprieve from what I knew Wendy intended.

Mistress bent over close to the divan and spoke tenderly to me, like I was a child about to do something I'd never done before. "Taking big cocks in your mouth and sissy pussy is expected of you now, Claudia. Remember when you pretended to be a man, how much you liked a girl to suck your little clitty, well no one's ever going to suck it again and now it's your turn to pleasure other cocks, like a good little slut." Mistress helped me down from the divan and soon the rubber cock was right in front of my face.

Miss Wendy smirked, "Yeah, Claudia, suck it good and be sloppy, get it all wet because you know where it's going next."

I looked at the huge strap-on and then I turned my head to look up at Mistress with pleading eyes.

"Go on, eventually you'll learn to love sucking cock and I'm giving you a break by not making you start on a live dick." Mistress laughed. "At least Wendy won't shoot all over your pretty face."

Oh my god, this is a break. I gathered myself and took a deep breath when I realized that they could have made me service a man.

Suddenly, Miss Wendy had apparently had enough of my hesitation and she reached over and grabbed me by the hair yanking me closer to the waving cock. The room was suddenly filled with the sound of chairs being repositioned by the other ladies so they could get a better view.

Miss Wendy pushed my head closer. "Now open up and say ahhh!" With only that warning she pushed the tip of the phallus to my lips and rested it there. From this position I saw the false cock had an enormous pair of faux testicles. There were also big authentic-looking veins running through it and the shiny mushroom-shaped head even seemed to have a hole like a man's urethra.

Now unceremoniously Miss Wendy forced my head towards her cock and guided the monster through my lips and into my waiting mouth.

Squeezing my eyes shut in fear, I reached out and grabbed Miss Wendy's legs with both of my hands for support.

"That's it baby, don't be afraid, take it in. Now use your tongue to lick around the head and tip first", she urged.

Even with my eyes closed, I heard the clicks of Mistress' camera and I knew she was taking pictures of me sucking my first cock. A flash of utter humiliation stabbed through me, but what could I do, I had to obey.

As I ran my tongue over the bulbous tip of the intruder in my mouth, Miss Wendy started to pump her hips a little as she urged me to take more and more of her cock.

"Good girl, take more, come on go deeper,, you little cocksucker!" she demanded of me. Soon the head began to intrude far enough to make me gag on it..

"Come on, take it all down your throat, I know you can and I'm pretty sure a slut like you wants too. " Miss Wendy laughed.

I wasn't so sure, but there were the physical dimensions to consider. It seemed impossible to fit the latex phallus down my throat and as she tried to force it my jaw felt like it was ready to break or, at the very least, become dislocated. Of course I was gagging and coughing up spit which was running out of the corners of my mouth, but there was a more important problem; I couldn't breathe.

Finally Miss Wendy stopped humping my face and pulled her latex cock away for a moment. Gratefully, I grabbed a big lungful of air, but as soon as I had, she continued; this time slapping my face with the huge strap-on. Thwack, came the sound as the organ slapped my cheeks and I could not stop her because she was still holding me by my hair.

"Are you ready to take it deep, bitch? I'll bet you are." Miss Wendy stopped slapping and pushed the latex cock deep in my throat making me think what more could she do to me.

After a few more pumps deep down my raped throat, Miss Wendy reached down and touched the faux testicles of her strap-on. "I'm nearly ready, whore, do you like to swallow? I hope so." With those words she squeezed the testicle sack and the head of the strap-on suddenly erupted with some kind of thick, viscous goo right into my mouth.

Immediately I gagged on the gunk and began to cough it up. I had no desire to swallow it, but Miss Wendy had other ideas.

Pulling the cock from my mouth, she instantly grabbed my nose and squeezed which of course forced me to breath, and swallow, through my mouth. With no other choice I began to swallow the vile-tasting goo hoping that once I did this ordeal would be over. I was so wrong.

"It's only simulated cum, but they make it nice and salty so it sort of approximates the real thing. Get used to the taste, slut." While holding my nose she actually used her fingers to push several gobs of the goo back into my mouth. "Best you get it all, real men don't like to see sissy sluts waste their precious cum."

She gave me a few moments to finish my task before she again reached for the faux testicles of her strap-on. When she did I nearly freaked out. Was there more of this disgusting stuff?

As the on looking women cheered, hooted and applauded, Miss Wendy cooed at me. "Now for the crowning glory, real men call this a facial." She squeezed the latex balls three times and each time a massive squirt of the goo splattered over my face. I barely had time to close my eyes and I had never experienced anything like this in my life. With my face covered in gooey cum, I could hear the catcalls and cheering of the onlookers.

"Turn this way, sweetie, to my voice. We must capture this for posterity. What would you say, girls, might it make the cover of Cum-drenched Sluts, the sissy edition?" The voice was my Mistress and even though my eyes were closed I knew she was capturing my splattered face to show others to my ultimate humiliation.

As the clicks of Mistress' camera died down, Miss Wendy asked. "Should we make her wipe it off and swallow every drop?"

There was a pause while my Mistress considered. "No, I think it might be better to save such an experience for when the cum is real. No sense in letting her gain too much experience too soon."

I was on the verge of tears under the coating of faux cum when my Mistress walked over and dropped something on my face. She cooed at me, "Go on and wipe your pretty little face."

Of course I did as I was told using the linen handkerchief to wipe the goo from my eyes and face as best I could, but when it was all off I realized my look, which Mistress had toiled on, was ruined. My mascara was left running down my cheeks and my pink lipstick smeared onto my chin and above my upper lip. I looked more like a cheap, slutty whore who had been sucking cock than the pretty girl Mistress had made me into.

End of Part One

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