A Tipsy Makeover

"Ashley!" I squealed, pulling my best friend into my arms on my doorstep.

"Anna! What's up, girlie?" Ashley asked as she stepped inside, shrugging out of her jacket and dropping her overnight bag on the floor. She wore sheer black leggings and a low-cut burgundy tank top, with a black knit beanie. Her caramel-brown locks fell just below her collar bones in soft waves, framing her sweet, round face. Her dainty nose was flushed bright pink from being outside in the cold, and her eyes were icy blue and rimmed with smoky black eyeliner and fake eyelashes. Briefly, I felt embarrassed that she was dressed normally, and I was in my pajamas — a tiny pair of pink shorts and a black camisole, my blonde locks scooped into a high ponytail.

"I was just making us some popcorn. And I convinced Jake to get us a bottle of wine," I giggled, referring to my twenty-three year-old brother. Jake totally understood when I asked him earlier, since he always asked his friends to buy him alcohol when he was nineteen, too. Technically, I was eighteen, but Ashley was nineteen. And he knew we would drink responsibly. since we were staying in for the night.

"Oh, sweet!" Ashley smiled. "But won't your parents be home tonight?"

"They're out for the weekend for a business conference. They left like, an hour ago."

Ashley nodded and headed upstairs to my bedroom, and I stopped in the kitchen to collect the popcorn and the chilled bottle of cheap white wine. The clock on the stove read 8:39 P.M., and I heard Jake yelling into his gaming headset in the basement — which was also his bedroom.

When I got to my bedroom, Ashley was laying on her stomach on my bed, in front of the TV, having kicked her boots off near the door. Her round eyes were fixed on her iPhone. Embarrassingly, I noticed how nice her ass looked in her leggings. Maybe I should buy some leggings like that.

"Scoot over, bitch!" I poked at her playfully, and she wiggled over on the bed as I dropped the popcorn on the side table, the wine on the bed next to us. I perched myself on the bed next to the wall. Ashley was scrolling on Instagram, and she shoved the phone in my direction.

"You would look so hot with your makeup done like that," she declared, referring to a blonde model with smoky eyeliner and red lipstick. Ashley was very interested in cosmetics, always chattering on about makeup and skincare trends.

"I'm not sure about red lipstick on me," I disagreed gently, taking a sip of wine out of the bottle. "I've got green eyes. It doesn't match."

"That doesn't matter! Don't be ridiculous. Where's your makeup bag? I can do your makeup, it'll be fun!" Her eyes lit up like a Christmas tree at the opportunity to do my makeup.

"It's in the bathroom, on the counter."

With that, Ashley darted to the bathroom, returning seconds later with my small bag of products that I hardly ever used. I heard her manicured nails clicking against packaging as she laid out each item carefully on my duvet, selecting my most expensive red lipstick — one I bought for special occasions, and had never worn.

When she was satisfied with her set-up, she straddled my lap, and tucked the few loose blonde tendrils of hair behind my ears before taking a big sip of wine.

Wow, she smells good. Like cinnamon and apples.

I flushed pink at how close she was to me, how soft her legs felt pressing into mine. Her full breasts were perched in a lacy push-up bra that poked out from neckline of her top... right in front of my face. Thank God she didn't notice my blush — too busy analyzing my makeup brushes. She applied a thin layer of concealer under my eyes and over my chin and forehead, then dusted my face with powder.

"You have such nice skin," she pouted, stroking my cheek with her finger. "I wish my skin was this nice."

God, she's... cute. Fuck, I'm not gay! I'm just getting flustered because she's sitting on top of me like this, I feebly reasoned with myself as Ashley swiped something through my thin, blonde eyebrows and dabbed shimmery powder over my cheekbones, her touch feather-light.

"Close your eyes," Ashley demanded. I did as I was told, and she applied a creamy black eyeliner, smudging it with her fingers. She leaned back to check her work, and forward again to keep working. The friction on my lap of her leaning back and forth left me feeling incredibly flustered. She clapped her hands together, clearly proud of her artwork. She took a few sips of wine as the eyeliner dried.

"Okay, now open your mouth," she said gently, focused. I did, hoping she didn't notice the flush that crept over my cheeks again. She painted the crimson liquid lipstick over my lips, and to my shock, dips a finger into my mouth.

"Suck."

My eyes widened, and something tingled deep in my stomach, but I sucked her fingertip as I was told. She twisted her finger and pulled it out.

"See?" she asked, motioning toward the lipstick on her fingertip, "All this lipstick would've dried and ended up on your teeth if it weren't for that little trick."

Oh. "Oh, t-that's cool," I stuttered once the lipstick was dry, unable to shake the blush from my cheeks.

Ashley made an excited noise, clapping her hands together again, and handed me the hand-held mirror. "I was so right. You look hot! Wait, take your hair down first!"

She slid the ponytail out of my hair, and pale golden waves cascaded around my shoulders. I stared into the mirror, and Ashley's makeup artistry was immaculate. I looked almost like the model in the photo. My pale green eyes were accentuated with dark, smoky black wings, and my scarlet lips looked full and soft. My ivory skin glowed.

"Wow, Ash, great job. I wish I was as good as you are with makeup," I squeaked, giving her a shy smile. She beamed, proud as ever.

"What can I say? I'm good with my hands," Ashley winked at me.

Is she flirting with me? I giggled in response, sipping at the bottle of wine to hide my embarrassment. Maybe I am into girls... But Ashley has had plenty of boyfriends, so there's no way she's a lesbian. She rolled over on the bed again, clicking the remote to the TV at the foot of my bed.

"Wanna watch Orange is the New Black? I've heard it's super good." Ashley suggested, scrolling through a streaming service's options for movies and "binge-worthy TV shows".

"Sure," I agreed and shrugged. I hadn't heard of Orange is the New Black, but I was still a little distracted from the makeover, and didn't really care what we were going to watch. She clicked on it and scooted next to me, offering me the bowl of popcorn. I accepted it, and we started to watch the show.

About thirty-five minutes passed. Thirty-five minutes of me sitting on my bed next to a girl I was, as embarrassed as I was to admit it, extremely attracted to. Ashley frequently made comments on the show, and we laughed a lot. Turns out, Orange is the New Black contained a lot of lesbian-themed content. We drank almost the entire bottle of wine between the two of us, and every time Ashley laughed, she put her hand on my thigh, leaning towards me affectionately. Ashley was so charming. Funny. Hot...

After Ashley and I finished laughing at something she said, we looked back to the screen, which unapologetically displayed two naked women... in the shower. Having sex. One of the women was on her knees with her head between the other's thighs, while the women moaned and arched against the shower wall. I blushed immediately. I wondered briefly what that would feel like. None of my boyfriends had ever done that to me before.

"Have you ever done that?" Ashley asked quietly, as if she read my mind. Did she notice me blushing? It only makes me blush more.

"N-no... None of my boyfriends have ever done that to me before," I stuttered, suddenly feeling uncomfortably warm.

"I meant... never mind." Ashley shook her head, clearly trying to fight a smile. Anxiety and something else tingled deep in my stomach. Wait... did she mean, 'have you ever fucked a girl'? Does she want to fuck me?

The wine gave me a burst of courage, and I didn't even think before saying it. "Oh... did you mean to ask if I've fucked a girl before?"

Even Ashley, who never seemed flustered, seemed flustered at my comment. Or maybe it was the wine that caused her to cheeks to flush pink like that. She giggled, this time in a shy way. "Yeah, that's what I was asking."

"No. Uh... I mean — I'm not gay."

"Oh. Right, right." She fixed her eyes on the screen again, and I downed the last of the wine. The wine made me feel so good. It took so much of the edge off my anxiety, and it made my whole body feel warm and tingly and happy. Fuck it.

"I'm not going to lie, though... I kinda want to." I surprised myself with how bold my comment was.

She looked at me, obviously still trying to hide a smile. "Wanting to fuck a girl doesn't always make you gay."

That made no sense to me, but I giggled and played along. "Well, have you ever fucked a girl?"

"Yeah," Ashley said with a soft laugh, and nodded. "A few times." Her laugh was so pretty.

"Oh..." I didn't know how else to reply. The wine complicated the process of trying to come up with a sentence that wouldn't embarrass me. I just blinked at her, gently biting my lip as I tried to come up with something else to say. I didn't have to, though, because she put her hand on my thigh again. She moved closer to me, and my heart started to beat a little quicker.

"That lipstick really does make you look hot, Anna," she whispered, moving her hand to swipe a blonde wisp of hair out of my face. I pressed my thighs together as it became evident that Ashley was, indeed, trying to flirt with me.

And, God help me, I had no intention of stopping her.

Slowly, her lips found mine, hovering just over them as she wound her fingers in my hair, just behind my neck. The area between my legs tingled as she tightened her grip, gently stroking my jawline with her other hand, finally pressing her soft lips into mine. I skimmed my hands hesitantly over her waist, resting them on the soft swell of her hips. I nervously wondered where it was okay to touch her... The thought made me realize I had no idea how to pleasure a girl, which both frightened and excited me.

Kissing her back, I carefully molded my lips to hers, savoring the soft femininity of her touch. I eased her hat off, tossed it away, and wrapped my fingers through her chocolate-colored locks. I could smell the wine on her breath just as I could feel it making me tipsy. In a moment of bravery, I delicately slid my tongue between her lips. She tasted so good, like sweet, apple-flavored lip balm. Suddenly, I'm realizing how much I like apples.

She eased her tongue against mine, welcoming my tongue pliantly. She skimmed her thumbs over my forearms and gripped my wrists, guiding my hands over her breasts, compelling me to squeeze them. Fuck, they're soft. I continued to fondle her, stroking every supple curve. I pulled at the hem of her tank top — a question — and she nodded into the kiss. I pulled the top over her head, revealing her large breasts in the lacy black bra, which featured a tiny black bow in the center. She pulled my camisole off as well, and it was not until now that I remembered I wasn't wearing a bra. My nipples stiffened as cool air washed over them, and I felt extra vulnerable, extra horny, as she trailed her fingers over them, squeezing my breasts, which were quite a bit smaller than hers.

Ashley broke the warm, feminine kiss, and slipped her fingers down my shorts, trailing over my thin, lace panties. Her touch was gentle, teasing. I didn't stop her, just panted against her mouth, and then felt warm desire clench deep in my stomach. Her fingers smoothed over my clit ever-so-slightly, over my panties, and I writhed gently under her touch. Her lips were so smooth, just grazing mine.

"So you've really never been with a girl before, Anna?" she whispered, her voice lower, seductive.

"No..." I whispered, my cheeks hot — I still wasn't sure if it was the wine or the attraction to my friend.

"Do you want me to make you feel good?" she asked, caressing me over my panties. "I can show you how to fuck another girl."

Warm wetness rushed between my legs as she asked the question. I was embarrassed to be reacting in such a slutty way, but Ashley was so hot. So different from any boyfriend I had ever had. I nodded desperately, staring into her molten blue eyes.

"Please," I whispered, spreading my legs for her. She smiled into our kiss, and brushed her thumb back and forth over my nipple, continuing her slow, torturous caresses over the thin lace panties. I allowed my hands to skim around her waist, down her back, down to her ass. The fabric of her leggings clung to her tightly, and I caressed her behind and thighs before slipping my hand down the back of her pants to grip her ass underneath her panties.

Ashley slipped her tongue back into my mouth seductively, a bit more demanding this time. She controlled the kiss, this one filled with more passion, with need. Her fingers gripped the back of my neck, pulling me further into her as she continued to tease me. She just barely stroked underneath my panties, and I lost track of where I ended and she began. We were a mess of tongues and lips, gentle strokes and hard squeezes.

Finally, she pulled my shorts and panties down, and I helped her strip me, leaving me completely naked under her gaze. I took her leggings off, arousal clenching deep in my stomach when I saw her perched over me on my bed, in only her underwear. I dragged my hands down her body, starting at her round breasts, down to her beautiful, porcelain thighs. Her body was perfect, round and curved and soft in every way. Her thong was intricate red lace, the straps sitting high on her wide hips. Her eyes were heavy with desire, and her wavy hair was tousled from my grip during our make-out session.

She kissed my jawline, stroking her fingers over my breast, dragging them down to my pussy. I gasped sharply when her fingers reached my bare pussy, skimming over my sensitive, wet folds. A hot wave of pleasure crashed over me as she finally started to drag circles around my swollen clit. I pressed my hips desperately into her hand, letting a quiet moan fall from my lips.

"Does this feel good, Anna?" Ashley murmured, her voice feminine and dripping with sex appeal.

"Yes," I gasped. My breathing grew heavier as she planted gentle kisses down my neck and collarbone.

I unclipped Ashley's bra, tossing it aside, and her full chest fell into my view, just above me. Something clenched inside me, and I cupped her soft breasts in my hands, mirroring what she did to me earlier, stroking my thumbs over her pink nipples. I'm rewarded by her quiet mewl of pleasure against my lips, and I pressed into her hand again, feeling hot and desperate all over. How could a girl's moan make me feel so horny?

Her lips fell at my breasts, leaving wet kisses along each swell of my chest. When she reached my nipple, she took it into her mouth, sucking it sweetly while still rubbing circles over my clit. I moaned again, embarrassed at how high-pitched and slutty it sounded.

She continued to kiss down my stomach, and I realized she was going to kiss me down there. I clenched my legs up, starting to feel self-conscious. No one has ever done that to me before! Ashley shot me a comforting, reassuring look, and I relaxed back into her touch.

Finally, her lips reached her destination, and the feeling of her full lips on my clit was extraordinary. She sucked at my folds, kissed at my inner thighs, circled her wet tongue around my sensitive bud. She dragged her soaked tongue up the length of my vulva, over and over, eliciting a desperate mewl from me. I fell so far into her seductive spell, so entranced by her nipping, sucking, kissing, that my nervousness was lost immediately. Suddenly, two fingers thrust inside my pussy, and I hadn't realized how empty I had felt until I was so deliciously full. She pumped her fingers in and out of my tight hole, still sucking gentle circles at my clit.

Minutes of torturous ecstasy passed, winding me tighter and tighter, and I begged my best friend for release.

It came out as a desperate whisper: "Please, deeper, Ashley, please."

She gazed up at me with those beautiful eyes, and thrust her slightly curled fingers inside me to her knuckles. Everything inside me that had been wound so tightly released. The world fell away, and all I could cling to was the sound of my own cries of pleasure. Ashley continued to finger-fuck me through the sweet waves of my orgasm, holding my hips in place, and when I relaxed, she collapsed on the bed next to me, legs intertwined with mine.

I blinked at her, suddenly feeling much more vulnerable than I felt a moment ago. We stayed next to each other like that for a few moments as I caught my breath. I trailed my fingers up her thigh, desperately wanting to give her the same pleasure she gave me moments ago, but nervous to attempt to get a girl off for the first time. She pulled me into another slow, deep kiss, probably sensing my over-thinking.

I slipped my fingers under her thin thong, stroking her at the apex of her thighs, sliding my fingers between her soft lips. She moaned quietly and opened herself to me, blooming under my fingers like a beautiful flower. I continued to stroke her, swiping her wetness up into gentle circles around her already-swollen clit. I let a few moments pass in this way, allowing myself to savor the quiet, high-pitched sounds of pleasure she made into my mouth while I pleasured her with my fingers, using my other hand to gently circle her nipple. She continued to fervently kiss me, her dainty hands woven through my hair, bucking her hips against my hand. Growing more and more desperate, she pulled on my hair.

"Please," she purred, gently directing my head downwards, toward her pussy.

I obeyed enthusiastically, pressing kisses down her soft breasts, stomach, and hips. I pressed a tender kiss into each of her inner thighs before dragging her thong down her thighs and sliding my tongue lightly over her pussy. I was rewarded by a soft, pleasured cry that almost sounded like my name. Wetness had pooled already between my own thighs, and I realized that eating pussy, making another girl writhe and moan underneath me, turned me on. A lot. I relentlessly continued to lap and suck at her clit, just the way she did to me. Her wet, warm pussy clenched tightly as I slid a finger inside, pumping it in and out slowly. I was then distracted by an idea.

When I masturbated, I would always do it on my stomach. It had always felt better for me if I did it that way. Maybe it would feel better for her that way, too. I gripped her hips tenderly, guiding her to flip over, sliding a pillow just under her hips. She didn't stop me. I was rewarded instantly by the visual of my best friend, face-down on my bed, back arched with her ass and pussy fully exposed. She was hot with clothes on, but like this... Fuck.

I returned to what I'd been doing. After only a few minutes of being licked and fingered in this position, she started to moan a little louder, her breath getting quicker and shallower. I thrust another finger inside her, and her velvety, warm walls squeezed around my fingers while she writhed on the pillow.

"Go faster, Anna," she moaned, spreading her legs further. I picked up my pace, thrusting my fingers into her wet cunt rapidly, making a wet noise and eliciting the prettiest moans I'd ever heard. She cried out her release, arching against my bed and moaning much like I did not long ago, before finally relaxing.