Make Up Sex

MAKE UP SEX

brIAR

I t was nice to wake up in a bed that wasn't a twin.

My dad, Alan, had gotten a gift certificate through some corporate sponsor at his work for a free weekend at a five-star hotel in Richmond and passed it on to me, so Casey and I drove up there to celebrate me finishing my first semester at Lassiter and not flunking a single class. It had been touch and go there for a while. The hotel was amazing, far more extravagant than any place I'd stayed before. We even had a suite, not just a regular room.

Last night, Casey had taken me on a dinner date, and for once it wasn't to Sheetz. We'd gone to a place with linen tablecloths, chandeliers, and actual candlelight. I'd ordered the lobster, because it felt like the sort of thing you had to order in a place that fancy. Casey had to help me get it out of the shell, so we'd shared it and I'd had some of his steak.

The whole dinner, he hadn't been able to keep his eyes off me, and it had nothing to do with our romantic surroundings. I'd once promised Casey I'd wear stockings, heels, and the blue and black skirt he liked out on a date, and last night I'd delivered. With the right makeup and hair products, I'd looked enough like a flat-chested woman that nobody in the dimly lit restaurant had noticed I wasn't. Or maybe they'd seen right through me, but they were too classy to cause a scene.

Then, later, back in the hotel, Casey had bent me over the back of the couch and eaten me out for what felt like hours. He was only pretty new to rimming, but holy shit, he was so good at it. I'd come so hard by the time he got his dick into me, that by that point I was having an out of body experience and watching the whole scene from where my spirit was floating about ten feet above the floor.

And then it was lights out until right now, when I woke up starfished across a bed that was actually big enough to hold an entire aquarium, and at the same time soft enough that it took me a while to realize I'd actually floated down from the ceiling after last night. I also realized I'd drooled into the pillow.

Despite being stretched as far in all directions as possible across the bed, I couldn't feel Casey beside me. I rolled over, still blinking awake properly, and saw him wandering through the wide expanse of the massive suite, picking up the trail of clothes we'd left strewn over the floor last night. He was wearing nothing but a pair of tight black boxer briefs, which was a fan-fucking-tastic sight to wake up to.

He looked over to me, and gave me a smile. "Hey, you're awake."

I yawned and stretched. I ached from the night before, but in the best way. "Why're you wearing briefs?"

"I ordered breakfast." He stooped down and picked up my blue satin underwear from the night before. "I didn't want to scare the room service person."

"Your dick's that not impressive," I said, which was a total lie.

"Yeah?" Casey said. "Because it seemed to impress the hell out of you last night."

I gave him a lazy smile. "Don't forget your tongue. That was pretty great as well. "

Casey grinned, looking like the cat that got the cream. Which he had.

There was a knock at the door and he dropped the clothing onto the couch and ducked into the bathroom. He came back out wearing a bathrobe and answered the door. He was back a moment later with the little room service cart.

After a quick detour to the bathroom, I wandered over to the pile of clothing and shimmied into the dark blue, barely-there satin panties I'd worn the night before and sat down at the dining table while Casey unloaded the cart. He'd ordered bacon and waffles with coffee and juice for both of us, and while we ate I took in the details of the suite. It was five star for sure, but it wasn't intimidatingly fancy. The furniture was sleek and modern and the living area had been decorated in soft creams and browns. The full-length windows that opened out onto the balcony let in enough daylight to make the space feel open and fresh. I could hear the faint sounds of traffic drifting up from the street below. What I couldn't hear were the sounds of a fraternity house waking up.

We were alone , and it was giving me all sorts of ideas. I grinned at Casey as I pushed my plate away. "Hey, wanna fuck me over the balcony and hope nobody looks up?"

He choked on his juice. "Jesus, Briar! No!"

"Well what, then?"

His brow creased.

I stood and walked around to his side of the table and slid into his lap, draping my arms around his neck. "Casey," I said in a low voice, "we are in a hotel. Alone. And I mean completely alone. There's zero chance of Marty or Scout or Trey or anyone else disturbing us. So, what do you want to do?"

"Oh." He swallowed. He rested one hand on the ass of my panties, stroking the fabric with his thumb. Then set his hands under my thighs and stood. I hooked my legs behind his lower back and as he carried me over to the couch. He didn't manhandle me that often, but I fucking loved it when he did. He set me down on the couch. "You look so sexy."

Casey had a thing for my panties. Like, sometimes even more than I did. I liked the way they made me feel cute and sexy and naughty—but a tiny flash of satin and you could see the second that Casey's thoughts dissolved into a blast of static and Casey.exe stopped working.

I reached back and ran a hand over my ass, tilting my head back. "In these, you mean?" Like I was wearing anything else.

The click of his throat as he swallowed was audible in the quiet of the room. He sat next to me on the couch and reached out, running the tip of his thumb under one eye and holding it up to show me a smear of leftover eyeliner. "I mean obviously, but I just love how pretty you look like this, baby."

I got a flutter low in my belly, and my cheeks heated. "You too."

Casey shook his head. "I'm just regular looking."

And there was something about the way he said it, a sort of resigned acceptance, that made my chest go tight. Before I'd thought too much about it, I found myself reaching out and lifting Casey's chin up and tilting his face this way and that.

"Oh, I don't know," I said. "There's a lot of potential here. You've got good bone structure, and a kissable mouth."

I leaned in and kissed him to prove it, and he kissed me back, slow and lazy, one hand sliding into my hair.

When he pulled back, he said, "Maybe I'll let you give me a makeover sometime. I've always wondered what it's like to feel pretty."

His tone was light, but there was something in his expression, a flash of longing, that told me he wasn't joking.

Thing was, Casey was pretty much an open book when it came to what he wanted, and he didn't play games. So the fact he'd even brought it up told me he was genuinely curious.

And hell, so was I—I hadn't been kidding when I said he had potential .

"You're already pretty," I said.

He snorted and laughed softly.

"I mean it!" I shivered as he caught the edge of my satin panties between his thumb and forefinger, and rubbed the fabric. "I've got another few pairs in my suitcase, you know."

"What?" His face went red.

"If you wanted to try them," I said. "Maybe dress up a little, like a princess."

"Fuck." His jaw dropped. Oh, he liked the sound of that, but he didn't know it yet. He wrinkled his nose. "You don't think that'd be weird?"

It was my turn to snort. "You think I would think it was weird? Casey, you've seen me, right? You don't think it's weird for me to do it, right?"

"No! But you're..." He shook his head. "You're gorgeous , Briar."

"So are you. Even though you're a blockhead." I leaned in and kissed the end of his nose. "Want to find out how pretty you are?"

He blinked, then let out a long breath. "I think I do, yeah."

"You're going to look incredible ." I got off the couch and crossed the room to my suitcase. I hadn't brought much with me. There was no way last night's skirt would fit Casey—I was skinnier than he was—but I'd packed an elastic-waisted chiffon skirt that would work, and I took it out, along with some blue satiny underwear. My blouse from last night was tangled up in our mess of clothing, so I untangled it and hung it over the back of a chair.

"Put these on first," I said, "and then come into the bathroom."

He took the underwear and skirt. "Why the bathroom?"

"Because I need the bright lights," I told him.

His eyes widened when I went back to my suitcase and pulled my makeup bag out.

Like, I called it a makeup bag, but it was more of a modest shipping container. It took up at least half the space in my suitcase. Mel, my dad's wife, liked to send me makeup and cute clothes she spotted, so my collection had really grown in the past few months. My dad gave me gift cards instead, because he didn't know his autumnal tones from his elbow. I even had a lipstick in the most terrible candy pink imaginable—it didn't suit me at all, and I suspected it was composed of actual crayon wax—but might have been my favorite because it had been given to me by Emily and Bethany, my two little half-sisters. It was weird that I'd had to hide this part of me for so long, and now I had a whole bunch of people in my life who not only just didn't care that I was femme, but encouraged me. Sometimes it felt as though I'd tumbled into a parallel universe, and the fall had left me dizzy in the best possible way.

I hauled my makeup box out, and nudged Casey into the bathroom.

He set the shirt and the underwear on the counter, squinting at his reflection as I turned on all the lights. "Uh, I don't really know what to do."

But he was already peeling his underwear down.

I was used to how hot he was. I was used to the way he wore a grin even when he was wearing nothing else, so comfortable and at ease in his body. So confident. But right now his hands shook as he took his underwear off and stepped into the blue satin panties, and something about his nervousness made my body thrum.

"You're doing it," I said, trying to keep my voice steady.

Casey pulled the panties up, the fine hairs on his legs catching against the elastic. His dick was at half mast, and any other day I would have loved to play with it, but watching him adjust himself in the panties was a whole lot more fun. There wasn't a lot of room in them, and his hips swayed as he tried to find a way to make it work. When he pulled his hand free, I could clearly see the satin tugging hard against the bulge of his dick and balls .

Casey pulled the skirt on next, and the way the hem fluttered around his thighs made my breath catch.

He gave himself a dubious look in the mirror.

"You look incredible," I said, and turned him around so he had his back to the mirror before he could argue the point. "Sit up on the counter for me."

Casey hoisted himself up onto the counter, and I stepped into the space between his knees. I ran my fingers over the hem of his skirt, and the prickling skin of his thighs. Then I put my hands on his waist, and kissed him softly on the lips. He let it happen, gazing at me with eyes full of questions.

I leaned past him and turned the tap in the sink on. I wet my hands, and then finger-combed Casey's hair down into a smooth, slick style. Very Liza in ‘Cabaret'—if you squinted. It was different to his usual haphazard style, and it worked with the shape of his face to make him look softer, sleeker. He wrinkled his nose, and so I leaned in and gave him another kiss before snapping my make up case open.

Casey peered down at the contents, eyes wide. "Are you sure I won't look…"

I prodded him lightly in the chest. "If you say stupid, I'll be highly insulted. Don't you trust me?"

Color rose in his cheeks. "Nah, you always look good. I just... I do trust you."

I wondered which one of us he was trying to convince. "It's not a tattoo, Casey. If you don't like it, you can wash it off straight away."

He nodded. "Okay, yeah. I knew that." Some of the tension in his spine eased and he gave me a slightly sheepish grin. "I know you know what you're doing, but you ever hear the phrase ‘put lipstick on a pig?'"

I snorted. "If you think pigs aren't adorable anyways, you're a fool."

He laughed softly, tugging at the hem of the skirt. "Now I feel like I should be insulted. "

"Why would you be insulted?" I asked. "I'm the one dating a pig."

His laugh was louder this time, echoing off the walls of the bathroom.

"Now, sit still," I said, grabbing my BB cream. "I don't want to mess this up."

No way was I going to do a full face. Not when I was so impatient to see the results myself. Contouring would have to wait for another day. I just wanted to give him a little base, some blusher, some lipstick, and do his eyes. Maybe one day, if he liked it this time, he'd let me do a full session, but for now all I was doing was showing him what it was like to see another, softer side of himself. And I appreciated that he was even willing to let me put lipstick on him—a lot of guys would balk at the prospect. But the longer we dated, the more Casey continued to surprise me.

"I don't think I am dating a pig, by the way," I said, as I dabbed the BB cream on his cheeks and forehead, and then reached for a sponge. "I think I'm dating a princess ."

Casey's breath shuddered out of him as though the word had stabbed him, and his eyes grew wide. I could feel the heat rising off him from where I was standing between his knees, and I brushed my knuckles against the chiffon fabric of the skirt just to be sure. He was hard. So hard that his dick must really be testing the limits of those panties.

I smiled as I smoothed out the cream. "You like that, huh?"

He didn't answer, just squirmed a little. Which was an answer all in itself. Whether he was getting turned on by being called a princess, or by me being bossy as hell and pushing him out of his comfort zone, or, like me, by embracing his feminine side, I didn't know yet. But it was working for him, and it was sure as shit working for me too.

I stepped in closer and slipped a hand under the hem of his skirt, resting it against his thigh and enjoying the way his muscles jumped under my touch. He really was getting off on this.

I ran the sponge over his jawline, blending the BB cream in expertly, and then pulled out my eyeshadow palette. I considered the colors for a moment and tapped a fingernail against a soft plum shade. "This one?"

Casey swallowed and nodded, and his eyelids fluttered closed. I leaned in and added a swipe of color across the top of each eyelid, then applied a softer contrast to the top part, blending the edges of the color with the applicator. I retrieved a liquid eyeliner from the bag and drew a thin line under each eye with a deft hand. Casey blinked at me, and fuck, he already looked incredible. "Such a pretty princess," I said quietly.

Casey's breathing hitched and a soft moan escaped him. I smiled to myself. He really liked that.

I put a hand under his chin and tilted his head from side to side, checking my handiwork.

"Okay, you have to open your mouth for this bit," I said, and his eyes flashed open. I waved the mascara wand at him. "Don't ask me why, but it's impossible to keep your mouth closed when you put mascara on. Just look up at the ceiling for me." I laughed. "No, don't move your head. Just move your eyes."

He blinked a couple of times, then rolled his eyes upward. I was quick with the mascara wand, adding the barest amount to his lower lashes, and Casey didn't even flinch. I had him look down and repeated the action on his top lashes.

"Now blink again," I said, twisting the wand back into the tube. "To make sure it doesn't clump."

He blinked. "Feels weird. Like my eyelashes are heavy."

"You'll forget it's even there in a second," I said.

"You learned to do this all yourself?" he asked as I rummaged for some blusher.

"YouTube tutorials, mostly." I snapped the blusher open and dusted the brush over it. "You have great cheekbones."

"Thanks," he said. "They hold up my face. "

I laughed and jabbed him in the ribs before adding a touch of blusher just under his cheekbones.

I loved that he was enjoying this, despite the newness of it, and, for him, the weirdness. He'd got over his nerves, although he hadn't actually seen himself yet. He hadn't seen what makeup could do, and right now? Right now Casey looked so fucking hot. His eyes seemed larger, his lashes longer, and with his slicked down hair he looked nothing like the bro he usually glanced at in the mirror. He looked pretty .

"Nearly done," I said, and reached out and ran a thumb over his lower lip. I reached into the makeup case and pulled out a couple of lipsticks—one bright red, one a darker burgundy—and held them out on my palm. "Pick one."

Casey didn't hesitate, picking up the burgundy one and holding it out. I wasn't surprised—it was one of his favorites. I took it from him and stepped in closer, crowding our bodies together. Casey swiped his tongue over his bottom lip, and I smoothed a hand down his arm to relax him. He held my gaze as I opened the lipstick, and I carefully applied it to his mouth. Upper lip first, trying my hardest not to make a mess of it—this was new for me too. I knew makeup, but I'd never put it on someone else before. Well, not unless you counted helping out my little sisters when they wanted to be princesses. But this was different. The air was charged, and there was a heaviness in the moment that both of us could feel. A connection, too, because Casey was allowing himself to be vulnerable. For me. He trusted me.

I applied the lipstick to his bottom lip, the tender skin dragging under the slight pressure. God, it was such a little thing, but the difference it made was like night and day. My frat boy boyfriend had a femme side, and I was the first person who ever got to see it. I was seeing it even before he was.

"Wow," I said. "You look amazing." He tried to turn to look in the mirror, but I held him still. "Just one more thing!"

I grabbed the blouse I'd worn last night and held it out to him. It was loose on me, but when Casey slid his arms into the sleeves, it was a snug fit, and the way he looked had my dick straining against the satin of my panties.

He swallowed. "Can I look now?"

"Almost. We just gotta blot your lipstick. Usually you'd use a tissue, but"—I stepped back between his legs—"I think we might do it this way."

And then I tangled my hands in his hair and kissed the fuck out of him.

Casey's breath caught and then he was kissing me back, his hands roaming over the planes of my back and his tongue dipping inside my mouth, claiming it, like he owned me. Which he kind of did.

I could feel the hard outline of his dick through the soft fabric of his skirt, and I reached down and flipped the hem up, running a hand over the bulge there. Casey moaned into my mouth and when I pulled away he was panting like he'd run a mile. His lipstick had smudged and he had a slightly startled look about him but somehow that just made him sexier. I kissed him again, softer this time, and guided him off the counter and turned him around so he could see himself in the mirror, settling my head on his shoulder and wrapping my arms around him.

"Do you like it?"

Casey stared at his reflection and I held my breath. I'd meant what I said. If Casey didn't like it, we could just wash it off, no harm no foul, but I hoped he'd see what I did—that he really was beautiful.

He blinked, then blinked again. His fingers trailed down the blouse, and then the skirt. He pressed his palm against the bulge of his dick, but didn't once take his eyes off his reflection. "Fuck. I look—Briar, I look good. " His voice shook a little as he said it.

"Of course you do. You're my pretty princess."

He smiled widely at that, and then he reached out and picked up his lipstick off the counter and applied another coat. It was a bit wobbly around the edges, but I was too distracted by the wicked gleam in his eye to care. "What are you doing?"

He turned and grasped my hips, steering me around until it was my ass pressing against the edge of the counter, and then he dropped to his knees, blinking up at me with big bambi eyes. "Want your princess to suck your dick?"

My knees almost gave out, and I gripped the edge of the counter tightly. "Hell, yes."

He nearly ripped my satin panties in his haste to get them down. I wouldn't have cared.

I squeezed my eyes shut as he took the head of my dick in his mouth, afraid that if I looked at him I'd come too fast. I mussed up his hair when I grabbed it, and almost cried out when he squeezed my balls with his clever fingers. Then he let go of them and pressed my taint, hard.

"Casey!" I gasped, my eyes flashing open. My hips gave an involuntary thrust, and Casey made a gagging sound. "Oh, shit, I'm s?—"

He pulled off, and asked in a rasping voice, "Are you trying to make my mascara run, Briar?"

"Uh."

"I could be into that," he said, the asshole, and leaned in and sucked my dick back into his mouth. And now he'd planted the idea in my head it wouldn't leave me alone—so I took it as permission, and fucked up into his mouth, hard.

He gagged again but didn't pull off, just blinked rapidly as he swallowed around my length and took me deeper, wet heat surrounding my length. The lone tear that slid down his face as he choked himself on my dick was the single hottest thing I'd ever seen. Then he followed it up with the second hottest thing I'd ever seen—he shoved a hand under his skirt and into his blue satin panties and began to jerk himself off with a frantic desperation.

I didn't even have a chance to warn him before I unloaded down his throat, my grip on his hair tightening as I held him in place. My cock pulsed and every nerve in my body lit up like a pinball machine as I shuddered and came. Casey moaned around my dick and worked me through the rest of my orgasm, licking at my still-leaking cock. The hand under his skirt sped up until he made a broken sound and sagged against my thighs like all his strings had been cut.

I tilted my head back, staring at the ceiling and waiting to get my breath back. I stroked Casey's hair as he breathed heavily against my hip. His hand curled around my thigh.

It took a long time for me to be able to move again.

"Casey?" I helped him to his feet, and we kissed. "Holy shit."

He quirked his mouth. "Yeah." He glanced over my shoulder into the mirror, and his smile widened. "Take a photo of me?"

"You're all mussed up."

He shrugged. "I know. That's why it's hot."

He wasn't wrong. Casey looked like he'd been ridden hard and put away wet. Which, coincidentally, gave me a great idea of how to spend the rest of the weekend.

"Okay," I said. "But you'll have to let me do your face again sometime. Properly."

He stared at himself in the mirror. "Okay."

"Really?"

"Yeah." He tore his gaze away from his reflection and ran a fingertip over his puffy lower lip, smearing his lipstick even more than it already was. "If you promise to do one thing for me?"

"What?" I asked, though I would have agreed to anything at all to see him like this again.

Color rose in his cheeks. "Call me your princess again."

Oh hell, yes.

"You don't need to be wearing lipstick and eyeshadow for me to call you my princess," I said, and reeled him in for a slow kiss.

He hummed against my mouth. "If I'm your princess, what does that make you?"

I didn't even have to think about it. I nipped at his earlobe and whispered, "It makes me very, very lucky."

Casey pressed a kiss to my jaw. "Love you."

My heart fluttered every time he said that. I'd never get tired of it. "I love you too." I squeezed his hand tightly and added, "Princess."

Casey smiled, and drew me out of the bathroom and back through the main room and straight to the bedroom.

He was such a fucking cuddler. Sometimes I pretended to hate it, but of course I didn't. He pulled me down onto the bed with him, and I went without a fight. He tugged me into place so I was curled up against his side and kissed the top of my head as he settled in to cuddle. I thought about suggesting he get undressed and clean the makeup off his face, but honestly? I was too comfortable to move.

"Casey?" I ran a hand down his side.

"Mmm?"

"I love you."

He pulled back and opened his eyes. "Didn't we just do this part?"

"I like sayin' it, is all."

He grinned. "Me too. Love you, Briar."

"Love you more."

"Not possible," he said.

We cuddled together in the middle of that massive bed, and I knew he was right. We were both crazy about each other. Casey dozed off first, and I lay there and watched the sunlight filter through the sheer curtains. Outside, all the way down on street level, the Richmond traffic hummed, and there was a whole city to explore. But, honestly, if Casey and I never got out of bed for the rest of the weekend, I wouldn't be mad about it.

In fact, it would be pretty much perfect.