Pretty in Pink Ch. 01

"Oh, come on!" I groaned, frantically fishing about the bottom of my purse. "I put those fuckers in here two seconds ago!"

It took me a few more agonizing minutes, but finally, I found my house keys. Somehow, I'd managed to rip the lining of my purse and they'd slipped inside, hidden behind a broken brush handle and...oh god, was that a chicken nugget? I'd been meaning to clean out my purse for ages, but now I actually meant it. Okay, I mostly meant it. I'd been shuffling between meetings all day, wincing at every step from the shooting pain in my feet. My mandatory "business heels" were a royal pain in the butt and the pantyhose wedgies only exacerbated the issue. First things first, I was going to throw off my shoes, sink into a bubble bath, and drink an entire bottle of wine. Then, if I felt like it, I'd deal with the chicken nugget situation.

It was a relief to come out of the harsh, summer sun and into the cool, dark interior of my apartment. It wasn't extravagant by any means, but I had enough space to keep me happy. I'd insisted on a large kitchen, but the dining room and living room were kind of snug. The master bedroom had its own bathroom though, which was a bonus. I still had a few emails to send before the day was out, but fuck all of those. I had a date with some hot, steamy water and a new set of scented oils. Throwing off my heels at the door, I began shedding my business attire, one item at a time. First came the pantyhose, which had been stained through with perspiration, then the pencil skirt which usually forced me into a waddle. When I finally made it to the master bedroom, there was only one more button on my blouse to deal with, but it was being finicky and I was seriously considering ripping the damn thing off. I hadn't been expecting to see Thomas on the other side of the door, since he was supposed to be working late. I definitely didn't expect to see him in a pink baby doll and matching thong.

For a few awkward moments, we just kind of stared at each other. I suppose that the polite thing to do would have been to apologize, shut the door, and pretend the whole thing had never happened. But I just...couldn't. Even if my life had depended on it, I'm not sure I'd have been able to look away. It was my first time seeing a full grown man in lingerie and I immediately knew it wouldn't be my last. If you'd asked me ten minutes before what I thought of men in dresses, I'd have probably pictured a hairy old man in a tutu and laughed it off. But Thomas was positively adorable. I don't think I'd ever been more turned on in my life. I could feel the heat rising in my cheeks as I eyed him, from his sleek, black hair to the curve of his bubble butt. I'd never considered pegging before, but damn, that boy's ass looked like it was made for a pounding. He looked better in lingerie than I probably did.

It didn't fit all that well, which was part of the appeal. The strap on his left shoulder had fallen down and he was gripping it earnestly, trying to cover himself up, even though there wasn't much of a point. The baby doll was made of a soft, sheer material and I could see under it. The tiny, lace thong wasn't big enough to contain his raging hard-on either, which poked out from under the cloth, pressing into the soft, sensual flesh of his belly. He'd painted his toes a dark shade of blue and there was just the slightest hint of mascara on his lashes, making his already big, blue eyes even bigger and bluer.

There was just something so innocent in his demeanor—so soft and sweet and serene—that made me want to tear every last piece of clothing off of him and wrestle his pretty boy butt onto the bed. I wanted to touch everything—the curve of his hip, the tip of his hardening cock, the slope of his neck—first with my hands, and then with my lips. But I wasn't stupid enough to make this worse for him than it already was. Thomas and I had only been dating a couple of months and had moved in together out of financial necessity more so than anything else. This was already becoming way too intimate for his liking. I could tell by the horrified expression on his face.

"Wait a minute..." I began, squinting my eyes. "Is that...my baby doll?"

"Fuck! Oh, Jesus, Erin!" Thomas cried and he blushed even more furiously than before, so that his cheeks matched his—no, my—lingerie. Frantically, he tried to cover himself with his hands and hide the prominent bulge sticking out from the thong, but we both knew it was too late. There was no coming back from this. "I was just...this isn't...I thought you were supposed to be working late!"

"Yeah, and I thought you were working late; guess we both got off early," I told him, still unable to stop staring. "Isn't that a little too small for you? You've ripped it."

"Oh, shit, I'm really sorry. I promise, I'll replace it," Thomas pleaded. "Just go ahead and pick something out online. I'll pay for it."

"Well, obviously, if you break someone else's stuff, you should pay for it," I told him, fiddling once more with my blouse, just so that I had something less enticing to look at and something non-molesty to do with my hands. "I...I'm sorry, I really should have knocked. I just didn't think..."

I didn't think you'd be wearing my clothes and putting on my makeup.

The words just sort of hung in the air like that—unspoken and yet somehow, all too loud—while we both twiddled our thumbs, looking at the ground and waiting for the other to say something, anything. It was killing me and finally, I got up the nerve to take in a deep breath and dart back behind the door and out into the hallway. Clearly, Thomas wasn't comfortable with me seeing this side of him and I was drawing out his embarrassment by standing there. I needed to get out of the house and give him some space. I'd never bring it up again, not unless he did. I'd give him an out. Maybe we weren't in love yet, but I liked the guy. No reason to ruin a good thing over a torn baby doll and some painted toes.

"I'm...I'm going to go get dinner, okay?" I shouted from behind the door, trying to sound as normal as possible. "We haven't had Chinese in a while and there's a new place a few blocks from here. I'll get us the usual, alright?"

Quickly, I started following my trail of clothes back out into the vestibule, shoving my hips back into the pencil skirt, searching the floor frantically for my pantyhose, only to find them flung onto the tacky, 70's era chandelier in the dining room. I was shoving my bloodied, bruised feet into the same god forsaken heels I'd worn to work when Thomas burst out of the bedroom, pulling on a pair of jeans as fast as he could and nearly tripping over himself in the process. He'd tried to wash the mascara off his face and hadn't been very successful. It was running down his cheeks, messing up his blush and making it all patchy.

"Erin, wait!" Thomas cried, stepping out in front of the door and blocking my only exit. "Erin, you're not going to leave me, are you?"

"Because you like wearing girls' clothes?" I laughed, incredulous, but Thomas winced and I realized he was serious. "I mean, Jesus, Tommy, I'm a little fucked in the head, but I'm not that fucked in the head."

"Erin, I...I know this is a bit much after only two months. I wasn't trying to trick you or anything. I really thought you'd be home late. I swear."

"Whatever you like to do on your own time isn't any of my business. You like to wear girls' clothes; I own a couple of butt plugs. We all have our quirks. I'm just sorry I didn't knock—you live here, too—so why don't I just grab us some Chinese and we forget about it? No need to ruin a good thing over this."

"Erin, do you..." Suddenly, Thomas looked like he might burst into tears. "Do you think differently of me?"

"You're pretty damn cute," I blurted, without even thinking about it, and now I was the embarrassed one. Oh god, I hadn't meant to admit that and a small part of me hoped that Thomas wouldn't notice. But his head suddenly jerked up and he was looking at me strangely, his expression intrigued. "Anyway, next time I'll knock, so we're cool now, right?" Quickly, I headed for the doorway, hoping to escape, but Thomas wouldn't budge.

"What did you just say?"

"No worries. I like dressing up, too. That's why I bought that baby doll in the first place. I understand the appeal. It's not really that big of a deal."

"Do you really think I'm...you know..."

I was staring into the carpet when he asked me that, but I couldn't just ignore such a straightforward question. Besides, I'd gotten myself into this mess in the first place, by staring when I should have been ducking out of the room, apologizing profusely. Reluctantly, I looked up, my eyes roaming over the adorable creature in front of me, so eager, with mascara running down his face and his pretty blue toes peaking out from his jeans. I could feel another blush rising in my cheeks, my heart beating heavily beneath my breasts. He could see his answer now; there was no sense in hiding it.

"You look pretty in pink," I admitted, but it wasn't the truth or at least, not all of it. "Ugh, that's not right," I sighed. "Tommy, you're gorgeous. Like, certified hottie kind of gorgeous. The kind of gorgeous other girls get jealous of."

"Erin, you really think so?"

"Not that it matters, of course," I stammered, getting redder and redder in the face. "This is your thing, I'm sure you don't want me bothering you about it."

"No! No, no, no! Erin, are you crazy?" Thomas cried, grabbing me by the shoulders and giving them a little shake. "I'd love to dress up for you! It's one of my favorite fantasies!"

"It's your fantasy to dress up for a pervert that wants to tear the lace right off you and fuck you in the butt?"

Oh god, did I just say that out loud?

"Yes, do you know how many guys would love to be fucked by a girl like you?"

"I don't know, like, three maybe?"

"Crossdressing, forced feminization, pegging...they're pretty popular," Thomas replied, an amused half-smile on his face. "You're not the only one out there who's perverted."

"I don't know," I drawled, narrowing my eyes at him suspiciously. "How come I've never seen porn of it?"

"Have you ever looked for porn of it?"

"No..." I began, and then the realization hit me like a ton of bricks. "You mean there's stuff like this on...on the internet?"

"Are we about to watch porn together?" Thomas asked, biting his lip like an excited school girl who had just been asked to the prom by the football captain. "Are we?"

I couldn't believe we were moving so fast—that in just under an hour, I'd found a whole new fetish and was as eager to try it out as my new boyfriend. A part of me thought it might not be a good idea, to just jump in like this. This was a lot more taboo than my butt plugs, shouldn't we talk more? Do a little research? Step back and think about things and maybe re-evaluate in the morning? But my cunt was on fire and I couldn't take it much longer; I made the executive decision to make mistakes now and worry about the consequences later.

"Go get the porn, I need to take these fucking heels off again."

Thomas took one last glance at me before heading to the bedroom, almost as if he weren't entirely sure this was real. Gingerly, I sat down on one of the dining room chairs and peeled my heels off again, wincing. From the bedroom, I could hear Thomas booting up his laptop and took a deep breath. The evening had certainly taken an interesting turn and there was no going back for either of us. It was exciting, but it was also...well, it was also scary.

What sort of deviants were we becoming? Exactly how deep did this rabbit hole go and how far would we end up falling?

"It's ready!" Thomas called.

"Coming!" I called back and, taking another deep breath, I headed toward the bedroom.

Thomas was lying belly down on the bed, his laptop open on the mattress and his feet kicking idly. Now he really looked like a girl, humming to himself as he scrolled through his files, his blue toes flashing in the florescent light. His pants had fallen down past his buttocks and I could see that he was still wearing my pink thong. It was like I had just walked in on my college roommate, checking her email while she waited for her toes to dry, not really caring if she was half-naked so long as she was comfortable. But his ass was so much nicer than her's had been and once again, visions of ass pounding started to dance in my head.

"Come here, don't be shy!" Thomas quipped, patting the space beside him. "Trust me, this has been a lot worse for me than it has been for you. I'm the one on trial here, you don't have anything to worry about."

"I don't know..." I drawled, still looking down at his ass and feeling the nub between my legs tingle. "What if we watch this stuff and I'm...what if we find stuff that I like and..." Thomas was looking at me peculiarly and it was making me self-conscious. "I mean, what if I...ugh, forget it, I'm just going to say it, alright? What if we watch this stuff and it turns out I'm even more perverted than you are?"

Thomas started laughing.

"Hey!" I grumbled, a little indignant. "I'm a repressed woman, alright? I grew up in a Catholic household, went to a private Catholic school, was pressured into going to a Catholic university. I don't know what I like. Not really. What if deep down, I like some really sick stuff and you decide you hate me?"

"I'd love if you turned out to be a huge pervert, Erin."

"You don't know that!"

"Alright, alright..." Thomas chuckled—enjoying this way too much for my own liking—and he pulled out a pad and pen from the night stand. "Let's watch some porn together for a little while. We'll start with some of my favorite videos—stuff I enjoyed enough to download—and then we'll take it from there. You go ahead and write down all the stuff you see that you're into—I won't look at it until we're all done—and then I'll circle all the things I also like. Deal?"

The grin on his face was starting to get a bit patronizing, but he was right, overall this must be far more nerve-wracking for him than it was for me, so I let it go.

"Alright, deal." I plopped down onto the bed and covered the pad of paper with my arm. "No looking, you swear?"

"Super swear!"

"Alright then, whatcha got?"

So confident and upbeat just moments before, Thomas looked a bit pale as he selected a file and it started to play. But as soon as it started, I stopped paying any attention to him. Thomas wasn't the most exciting thing in the room anymore.

On screen was a massive bed with a solid wood frame—the kind that rich people in the movies always have—with dark red bedding and a matching canopy. And sprawled across it—tied spread eagle, a limb stretched toward each of its four posts—was a gorgeous young man dressed in pink lingerie with white lace. Pink panties, stockings, and even a garter belt, all accentuating his shapely calves and adorable round ass. His cock was hard as a rock, the head poking out just beyond his panties and shiny with pre-cum. He had been waxed completely clean—every inch of pale, pulsating flesh was visible—and his face was made-up like a doll's, with light blue eyeshadow, prominent fake lashes, and blood red lipstick. Very classy. He even wore a pink ball gag, with a little red heart in the middle. Honestly, he looked like a Valentine; all he needed was some chocolate coating and just the thought of it had me drooling.

Sensing I was being watched, I looked over at Thomas and caught him staring at me before quickly turning away, pretending to be fascinated with a clip he'd seen dozens of times before. He looked embarrassed; I probably looked a little embarrassed, too.

A woman with dark hair and dark eyes came into frame then, absolutely gorgeous. She was wearing a tight leather jacket, leather panties (those were a thing?!?!), and thigh-high leather boots, accented with small, silver spikes at the knee. Immediately, you knew that she was in charge, and not just because the only other person in the room happened to be tied down. The woman just had this...aura of confidence. Of complete control. Whereas I couldn't stop staring at the man on the bed, she didn't even look at him. She didn't even glance in his direction. It was as if he were part of the room itself—a piece of furniture, like a lamp, with no need for any special attention. I couldn't believe it, Why didn't she look? How could she not, when he was such an obviously tasty morsel, all dressed up for the occasion, totally exposed and at her mercy? And that's when I finally got it. It's not like he was going anywhere! He was on her schedule, not the other way around! It was the hottest thing I'd ever seen and she hadn't even touched him yet.

The leather jacket came off and suddenly, there were her tits—huge, way bigger than mine—barely contained inside her black leather bra. Then she walked around the bed—her heels clicking menacingly on the hardwood floor—and opened a bedside drawer. Her victim's eyes widened—And honestly, so did mine!—as she pulled out a decently sized strap-on, purple and studded with little metal pearls. There was no sound as she stepped into it and pulled it up over her hips, save for the sensual rub of leather against leather. Now properly outfitted, she crawled onto the bed and settled herself on her victim's hips, only a bit of cloth separating his cock from her pussy.

"Sorry, slut, but this is the biggest cock I could find." Thrusting her long, purple cock into his face, she began using her perfectly manicured fingers to trace its contours, ever so slowly jerking it and rocking her hips against his real-life, human penis. There was a teasing smirk on her lips and an evil glint in her eye. "A whole six inches, but that's probably just foreplay for a slut like you, isn't it?"

Admittedly, I had started out a little wet—just from seeing Thomas in lingerie—but now, I was soaked through. I could feel the nub between my legs ache with urgency—with need—and my cunt catch fire. We were a minute and a half into the first video and already I couldn't contain myself. Shameless, but unavoidable. I'd never before seen a man penetrated and yeah, it hadn't happened yet, but the anticipation was turning out to be a major hot button. The look on the boy's face—flushed and eager and a little bit scared, all at once—was intensely erotic. I couldn't wait any longer.

"Thomas, take it off," I whispered, pulling my blouse up and over my head. "Take it all off, right now."

"Already?" Thomas asked, but then he shrugged and went to turn off his laptop. "Okay." Without a second thought, I slapped his hand away.

"No! Don't turn it off. Just take off your clothes. You're hard, aren't you?"

"Yeah..."

Frantically, I squirmed out of my pencil skirt and then threw off my panties, but when I looked back at Thomas, he had barely started. In fact, he'd only just unbuttoned his jeans. It wasn't fast enough; I had needs, for fuck's sake—urgent needs!—and I couldn't wait for him to figure out how to take off his pants like a big boy.