Pretty in Pink Ch. 02

"I'm sorry, Miss," Thomas whimpered. "I'm sorry."

"Now you're whimpering?" I hissed, narrowing my eyes at him and feeling a warm, pleasant darkness rise up inside of me. "You're whimpering, when you know exactly what your whimpers do to me?"

"I'm sorry, Miss, I—"

"Not another word, panty boy."

I could feel the darkness more prominently now, as it twisted and turned inside of me, making me cold and grotesque all at once. All the cruelest, most sadistic parts of myself were clawing their way to the surface, like a Pandora's Box of my most perverse desires. It terrified me, but it also felt so...right. So natural. Up until this point, I'd largely being playing a part—putting on the show I thought Thomas wanted to see. But now, after tasting his screams on my lips? The monster inside of me had awakened and though a part of me yearned to push back and fight it, I also knew that I couldn't. Thomas wanted this—I wanted this—and as long as I stayed within the boundaries he had set, I could do whatever I pleased. Anything I could imagine—any twisted, devious torture I devised—could be made real. As the darkness washed over me, I reminded myself that Thomas enjoyed being hurt just as much as I liked hurting him. My insecurities be damned, it was time to take control. I had it inside of me, I just had to trust that I could let it out and that Thomas would love me all the more for it.

Fuck it. He could always use his safe-word.

"If you insist on running that mouth of yours, you might as well put it to good use and help me get a little relief," I reasoned and by the look on Thomas' face, I could tell he knew exactly what I intended. Shoving my panties into my skirt pocket, I stepped over the head of the table so that, once again, Thomas could see under my skirt. This time, however, he'd get an even better view: my gorgeous ass and bald pussy. Lowering myself onto Thomas' face, I could feel the warmth of his skin as it pressed against mine and his muffled protests as I smothered him with my swollen sex. "Go on," I told Susan. "Let him scream into my cunt and while he's eating me out, do his balls and taint."

Susan nodded and as she ripped off the first strip of wax, I could feel Thomas screaming into my soft, aching flesh, sending vibration after vibration through my clit and setting the nerves aflame. After each new gasp of pain, I'd sit up for just a moment—only long enough to get a few breaths in—and then I'd be straddling his face again, feeling him hiss in agony against my cunt. His cries reverberated throughout my entire being, making my body shiver and my toes curl beneath me.

It was pure ecstasy; it was heaven.

"Suck my clit," I ordered, firmly, but gently, and I pressed the tender nub to his lips. "And I don't care how much pain you're in, don't you dare bite me."

I could feel Thomas' lips envelope my clit as he began to suckle, gently at first—my boy knew how to properly please a lady—then more insistently. Wrapping my fingers in his hair, I pushed his face up into my crotch and hissed in pleasure as his tongue got to work. Beneath me, I could feel him arch his neck—trying to get still closer—and it occurred to me just how difficult this must be for him, tied up and unable to get any real leverage.

It made the moment so much hotter.

"Poor panty boy, this must be so frustrating without the use of your hands," I laughed, stroking his hair as if he were a mere pet, rather than a person. "Not that that's any excuse." But rather than an insult, Thomas seemed to take this as a challenge and with a grunt of effort, lifted his face just enough so that he could shove his tongue into the warm, wet hole of my cunt. It took me by surprise and I gasped, moaning as the sensations washed over me. "Wow, not bad, panty boy. Not bad at all."

As my body rocked against his tongue, I couldn't help but look back and admire his freshly waxed flesh, now mine to exploit and enjoy. I'd never had a boyfriend so completely naked before—his pale, white skin totally vulnerable beneath the fluorescent lighting—and we weren't even finished yet. Out of the corner of my eye, I could see Susan open the second crock-pot—the one with the hard wax—and scoop a generous portion onto her wooden spatula. Thomas wasn't at all prepared when he felt her hands on his balls—pushing his still-hard cock aside in order to apply it—and I could feel him stiffen underneath me.

"Don't be such a baby," I panted, still grinding against his face and loving it. "I got my pussy waxed so that you could enjoy it and now that it's time to return the favor, you're getting cold feet?"

"Men are so pathetic," Susan sighed, and as she spread the wax over his balls and bikini line, I had to admit, even I was a little intimidated by her attention to detail. The woman didn't miss a single nook or cranny. Not one hair on his sack was safe. "They're always so quick to brag about how tough they are and to flex their muscles—barking at strangers and picking fights—but put a little wax on their balls and suddenly, they crumble."

"You scared?" I asked, standing up so that I could hear Thomas' answer. "You think your poor balls will be able to make it?"

"Just get it over with quickly," Thomas panted, his face shiny with my juices. "Please."

"We're begging now, are we?" I asked, pleasantly surprised. "We know who's in charge now, don't we?"

"Yes, Miss, please," Thomas begged, fear and desire intermingled in his eyes. "Have some mercy on me and just do it."

"You heard the boy. Let 'er rip."

Thomas' arms strained desperately against his bonds as Susan pulled away the paper strips, his cries coming in short, sharp little gasps of shock and pain. It was quick, just liked he'd asked, but I'm not so sure it was merciful. Susan didn't leave room for a single pause to breathe until Thomas' crotch was as bald and as red as a baby bird. It looked absolutely delicious. I could totally see why men were so insistent on eating waxed pussy. Waxed balls looked even better and bending over, I engulfed his cock in my mouth, gave it a good suck, and then released him.

"Don't spoil him," Susan warned. "He needs to learn how it feels to have his cock hard for a couple of hours or he'll just get entitled."

"I didn't say I was going to let him cum," I replied, as if offended by the mere thought. "But doesn't it look delicious? You can't blame me for wanting a taste."

Looking over at Thomas with my most seductive bedroom eyes, I leaned back down and engulfed his cock in my mouth. Our playtime had made him hot and eager, so it was the perfect opportunity for a good tease. I started out gently—just licking along his length, then moving to the ridge below the head, and finally the teardrop-shaped opening at the tip. Once I had his cock good and wet, I began bobbing my head up and down—sucking and slurping as I went—slowly at first and then faster. In no time at all, I could feel his cock start to thicken and tremble inside my mouth, on the verge of boiling over. He was so close I could literally taste it, the pre-cum overflowing onto my tongue. But just before he came, I released him, letting his ruined orgasm dribble out pitifully onto his freshly waxed balls.

"Miss, please, have some mercy!" Thomas cried out, his poor, unsatisfied cock still twitching. "Please, I'm begging you!"

"He's pretty good at the whole begging thing," Susan mused. "You gonna reward him for it?"

"No, not yet. Not until we're finished," I insisted, and I meant it. "Only pretty boys get to cum and he still looks like he lives in a tent by the side of the road."

"Alright. Let's get his arms, then turn him over and wax the rest of him before it gets too late. We still have a lot of work to do."

Once Thomas had been waxed from head to toe, we untied him. I'd always thought he looked hot—a little skinny, but cute, too, in that bookish, nerdy kind of way—and yet, even this small change had completely transformed him. Thomas wasn't just hot anymore; he was completely irresistible. With all the hair now ripped from his body, his perfect, flushed skin shimmered beneath the light and now, nothing was sacred. Every adorable imperfection—the dimples below his ass cheeks, the freckles on his chest, the mole right above his crotch—was exposed. My eyes drank in every inch of his nakedness and I licked my lips, hungry to possess him. Thomas looked so vulnerable—so fragile—that I was afraid I might break him and yet, I wanted nothing more than to watch him break.

"How are we feeling, panty boy?"

"A little cold," Thomas admitted, looking over his freshly waxed skin. "And a little...naked, too."

"Don't fret," I told him. "You won't be naked long. We've got something special planned for you."

Turning toward the vanity, Susan opened one of the bottom drawers, pulled out a small rectangular box, and passed it over to me. Inside—beneath layers and layers of pink tissue paper—were a pair of lace panties, a matching corset, and a garter belt with thigh-high stockings, all black and all silk. The entire set had cost me a pretty penny—I'd had to dip into my savings to afford it—but it was worth it. I'd had more fun picking this set out for Thomas than I'd ever had picking out something for myself.

"Put it on," I ordered, handing Thomas the box. "And do it slowly. I want to watch and I want to enjoy it."

"Of course, Miss," Thomas whispered, as if entranced by the fabric. "Of course."

Leaning back against the vanity, my arms crossed in front of my chest, I watched as Thomas first pulled on the corset, then stepped into the garter belt. It hugged his ass as he pulled it up and over his hips, the silk dragging sensually against his skin and making a lovely, sweet sound. The panties were even more enticing and as I watched Thomas slide them on, I eased my hand down past my skirt and began to play with my clit. Glancing over at me, Thomas did a double take, then stopped, blushing furiously. It was as if in that moment, he finally realized what a decadent piece of meat he was and how fully I intended to objectify him.

"Did I tell you stop?" I hissed, and he blushed even more furiously. "I told you I was going to enjoy the show. Does that make you uncomfortable?" Sitting atop the vanity, I pulled up my skirt and spread my legs wide, giving him a good view as I masturbated, so that he'd understand just how few fucks I gave. "I paid good money for that lingerie. Put it on. Now."

With a gulp, Thomas nodded and pulled the panties up and over his cock, creating a little bulge in the lace that was absolutely tantalizing. Circling my fingers, I picked up the pace, totally entranced as he reached for the nylon stockings. They took on the shape of his calves as he pulled them up and over his freshly waxed legs and my fingers began to work even faster. He clipped the tops of the stockings to his garter belt, accentuating his bubble butt, and I began to feel an orgasm build, just a tickle at first, then a persistent, agonizing ache between my legs.

"We're not done yet," I told Thomas, gasping, and with my left hand, I thrust two fingers into my cunt. "Turn around for me. Good boy. Now, bend over." Thomas obeyed and I could see his incredible ass in front of me, perfect and pale. "Alright, now turn back around. That's it. Oh, god. Pull your cock out. Jerk it, but don't cum."

Pulling his cock out the side of his panties, Thomas grasped it in his hands and began to masturbate, slowly at first, then faster. His head rolled back as the pleasure washed over him, but it was too much—he was too close to cumming—and the poor thing had to stop, his engorged cock twitching as he moaned in frustration. That's what did it for me. As his body trembled in need and agony, I felt my cunt clench and the orgasm finally washed over me, causing me to gasp and writhe on the vanity, my whole body spasming as wave after wave of pleasure crashed over me.

"That was amazing," I panted, but we still had work to do, so I quickly wiped my hands clean and jumped from the vanity. "Thank you, panty boy."

"But, Miss, please," Thomas begged, looking absolutely miserable, with his unsatisfied cock so hard, it hurt. "Please, Miss, please..."

"I told you, not until we're not done," I snapped. "Susan, help me restrain him, won't you?"

"Oh!"

Each grabbing an arm, Susan and I half-guided, half dragged Thomas toward the bondage chair by the vanity. I could tell that he was nervous—when I pressed my ear to his back, I could hear his heart racing beneath his rib cage—but he let us sit him down and strap him in. It was a very intimidating piece of furniture: there were black leather straps for his wrists, ankles, legs, and arms. There were even straps for his waist and torso. By the time they'd all been tightened and secured, Thomas was completely immobile.

Well, almost.

Gently, I pushed him back against the headrest and as I pulled the final strap across his forehead, I could feel Thomas shudder.

"What's that for?" Thomas whispered, sounding a little hoarse. "Erin?"

"Don't be so jumpy, panty boy, we're just gonna make you beautiful, that's all," I told him, and I knelt down so that we were at eye level. "If you were to move—even accidentally—you'd ruin my perfect canvas and then I'd have to punish you. Really, Tommy, this is more for your benefit than for mine."

"I could do my own makeup," Thomas replied, smiling nervously. "It wouldn't take long."

"Oh, please," I snorted, standing to my feet and rolling my eyes. "You don't know the first thing about makeup."

"I've practiced. Dozens of times. While you were at work or at a function."

"You've dabbled," I corrected, walking over to the vanity and carefully looking over my options. There was a jar of brushes beside the mirror and smiling, I selected a small one with a just a bit of 'poof' and a tapered tip. Turning toward Thomas, I dangled it in front of his face and waited. "What's this?"

"An eyeshadow brush."

"Very good, but what kind of eyeshadow brush?" I prompted, and Thomas' face—so proud just moments before—fell. "Come on, what's it used for?"

"For...applying eyeshadow?" Thomas finished weakly, and Susan laughed.

"And what's face primer for?" I pressed. Thomas opened his mouth, then closed it, looking a lot like a deer in the headlights, the poor guy. "Come on, Mr. 'I Can Do My Own Makeup.' What sort of face primer would I use for someone with your complexion?"

"I'm...not sure..."

"You're not sure?" I teased, relentless as ever. Thomas tried to look away, but with his head strapped down, there was no way to escape my mocking gaze. "This is basic stuff, panty boy. Do you wanna explain how to pull off full face contouring? I'm listening."

"I'm sorry, Miss, but I...I can't."

"I bet you just throw on a little blush and mascara and call it a day, don't you?" Susan jeered, and when Thomas didn't answer, it just emboldened her. "Yeah, that's what I thought."

"Let this be a learning experience, panty boy," I told Thomas, grabbing a few makeup wipes from the vanity. "So pay attention."

Gently, I wiped my juices from his face, so that I'd have a clean slate to work with. Thomas had already shaved earlier that day, so there wasn't much prep work required. Selecting a face primer from the vanity, I returned and began to rub it into his skin, being careful not to over-saturate it. I'd gotten facials before and while this wasn't quite the same thing, I could tell Thomas was enjoying it. It's always nice to have your temples and cheeks massaged.

"Since your skin is a bit oily, I'm using a matte primer, to help with your natural sheen," I explained, dabbing it under his eyes and then going back for just a touch more. "It's also got a green tint to it to help balance out any redness. But the main purpose of a face primer is to make sure everything else 'sticks.' There will be a separate primer for your eyelids, to help bring out the pigmentation of the eyeshadow."

"Are we going for a natural look?" Susan asked, gathering up a little tray of supplies by the vanity. "Or something else?"

"I just want a splash of color on the eyes and lips. Nothing too fancy, but I don't want to go neutral, either."

"So what's next?"

"Hand me the scotch tape," I told her and with careful precision, I placed a strip on either side of Thomas' face, lateral to the eyes and at an ever-so-slight angle. Thomas raised his eyebrows at me, confused, and with a little laugh, I felt myself break character. "I know, I know! It looks ridiculous, but it keeps the fallout from the eyeshadow under control."

I applied the eyeshadow primer, then motioned for Susan to bring me the makeup tray. The palette she'd selected was gorgeous—high quality pigmentation with a good mix of matte, shimmer, and metallic formulations. It was big, too—one of those samplers with a whole rainbow of colors to choose from. Too many to choose from. I pondered the palette for a moment, trying to pinpoint the look I wanted.

"Since the lingerie is dark, I was thinking something with a yellow undertone," Susan suggested. "Maybe even a little gold, along the upper and lower lashlines."

"Yeah, I like that," I mused, and the more I thought about it, the more I liked it. "It's classy, but it's also got a hint of flashiness, too. It says, 'I'm a total slut, but I'm not gonna brag about it.' It's just perfect for Tommy, and we can do gold nail polish to match."

"Sounds good to me."

Kneeling beside Thomas, Susan reached under first one armrest and then the other, pulling out two hand-shaped extensions. There were tiny leather straps for each of his fingers and slowly, she began to strap them down, so that he couldn't even move those. One thing was certain, Susan wasn't fucking around. When she said "forced feminization," she meant it.

"Jesus fucking Christ," Thomas gasped, sounding both impressed and a little afraid, all at the same time. "You're a monster."

"Yeah, I know, it's hot, right?" Susan replied, smiling. "My daddy was a carpenter and taught me well, thank god, or I would have had to pay out the nose for all the custom furniture in this place." Turning toward me, Susan nodded toward the vanity. "Can you grab me the yellow matte and gold glitter polish? Oh, and a base and top coat, the insta-dry spray, and maybe some cuticle oil, too?"

While Susan did his nails, I started work on Thomas' face. Grabbing a blending brush from the tray, I dabbed the bristles in a light, honeysuckle yellow and told him to close his eyes. He was tense at first—no doubt trying to stay still for me—but as the seconds turned into minutes, he relaxed back into his seat and I could hear him moan as the bristles tickled his skin. Gently, I began applying the shadow to his eyelid, starting at the crease and moving toward the brow bone in tiny, circular motions. With one hand, I steadied his face and with the other, I blended outward, so that the color got lighter the farther I went. First one eye, then the other. The next shadow was just a shade brighter—lemon drop yellow—and again, I started at the crease and moved outward, this time stopping just a little lower. The final color—bright yellow, like a daffodil—was packed onto the lid with a precision shadow brush, then only lightly blended out.

"You like that?" I whispered, letting my lips tickle his ear. "Does it feel good?"

"Mm-hmm."

"Just wait until I let you open your eyes, gorgeous," I teased, and I kissed his forehead. "You're absolutely stunning, do you know that?"

Next up was a gold shimmer shadow. Dusty, but not unmanageable. After applying another layer of primer to the upper and lower lashlines, I carefully dabbed it on using an angled liner brush, then reached for the eyeliner. I'd always had trouble drawing wings on myself, but drawing them on Thomas was surprisingly easy. All that was left were the false lashes—the full volume variety, for elegant parties—which I added with a little glue and patience. Once done, I removed the scotch tape, and that was it.