Sexcapades Of Cassidy And Annalise

"Don't you ever get bored?"

I blinked in surprise, the unexpected question rousing me from my contemplative trance. Turning away from my computer, I glanced over my shoulder. My body followed the motion as my chair swiveled slowly to complete the action. Facing the open door to my study, I cocked my head to the side, quirking my eyebrows curiously at my bestie.

Annalise stood in the entrance, leaning against the doorway in her black tank top and red short shorts. One hand perched against the curve of her waist, her other arm was hidden behind the wall. Short and svelte, her body language and demeanor told me that my redheaded housemate was bored and looking for conversation.

"Of what?" I asked innocently. She pouted at me, snorting a short harrumph'd breath of annoyance through her nostrils as she frowned. The action was almost childlike but it somehow suited Annalise. I'd always thought she was cute.

"You know what I'm talking about." Moving fully into the doorframe now, I saw that she held an apple in her hand.

"Of writing?" I knew it wasn't the answer she was looking for, but she was fun to tease. I shrugged, "Nah, I have too many stories to write to ever get bored of it. Plus, if I stopped, I wouldn't be able to afford rent." I flashed her a sassy grin. "And that'd be just tragic."

She bit into her apple, rolling her eyes at me as she crunched away. "Not of writing," she said with her mouth full, chewing between syllables. "Not that you do very much of it anyway," she scoffed. "Half the time I see you, you're just staring off into space."

It was my turn to roll my eyes at her. Leaning back into my chair, I gestured as if my finger were a pointing stick, wagging it to punctuate each word. "Thinking happens before writing," I replied matter-of-factly.

"Pshh," she rolled her eyes back at me, this time more dramatically. We had silly competitions sometimes. Doesn't everyone? Seemed like today's theme was going to be eye rolling. I made a mental note to one up her later. "Anyway, that's not what I meant."

"Then what did you mean?" I knew what she meant. We'd talked about it plenty of times already. It was an uncommonly common topic that often popped up when we were drunk or high. Or rather, only ever popped up during those times. Until recently, in the last few months...

"I meant, don't you ever get bored of...y'know!" She gestured at me at my desk, sitting in front of my computer's double monitors. I stared blankly back at her, my expression a careful display of silent bemusement. Exasperated, she finally blurted out "Daydreaming!"

I clapped my hand over my heart dramatically, my body language a show of mock offense. "How dare you. I don't daydream. I build worlds! I create stories! I -"

"Constantly daydream about sex yet never get laid," she cut in sarcastically.

Ouch. She'd gone straight for it this time, poking right into the heart of things.

It was my turn to pout at her, though it was tinged with a slight scowl. I let my chair swivel back slightly so that my side was facing towards her as I turned slowly, each inch bringing me closer to facing my monitors again. "Well, if you have nothing nice to say to me then I guess this conversation is over." I waved her off dismissively. "I have a lot of work to do."

Annalise took this as an invitation to get comfortable. Still munching away, making steady progress snacking on her apple, she plopped herself onto the window seat across from me. Noticing this, I resigned myself to her company and turned so that I was once again staring at my current work-in-progress - a blank page. From the corner of my eye, I could see her pulling her legs up to sit cross-legged on the window seat.

"I mean it!" she continued where she'd left off, as if unaware of my response. She waved her half-eaten apple at me, gesturing with it as she spoke. "Don't you ever get bored of just writing about it? Like, seriously Cassidy. When's the last time you got laid?"

"Just last night," I replied dryly, still staring determinedly at my monitor as if words would suddenly start appearing across it. Masturbating counts as sex, right? It wasn't technically a lie.

"With an actual dick."

"Yep." That's what I call my vibrator, I thought to myself, sniggering silently at my own silliness. Actual Dick.

"Your vibrator does not count," she replied flatly, showing that she knew me far too well.

I made a face at her, it was time to admit defeat. But she wasn't done yet.

"See?!" The apple rose and fell as she waved her arm around in exasperation. "You can't even remember the last time you fucked someone!" I blew out my cheeks, pouting sullenly at my blank monitor. There was no stopping Annalise once she got started. She was honestly starting to sound like my mother.

"When was the last time you went on a date then?" She didn't even wait for me to reply. "You don't fucking know. It's been so long that you probably can't even remember the last time you got dressed for a night out."

I glanced down at myself quizzically. What was wrong with the clothes I was wearing? Sure, I perpetually wore baggy t-shirts as pajamas. Yes, I worked from home and usually rolled out of bed before plopping straight into my chair after my morning routine but...Okay, so I may have been wearing the same thing 24/7 for the past two weeks now but that's...that's normal for people who work from home, right?

Fine. Maybe Annalise had a valid point.

"What do you want, Annalise?" I turned to face her. "Why are you here?" I demanded, now feeling legitimately irate at the sudden critique of my sex life, or lack thereof. "Where exactly are you trying to go with this?" With each question, my tone grew a little more exasperated. I tried to pull back to a more neutral tone. I didn't want to sound like I was annoyed at her...even though I was; she could be rather annoying after all.

"I'm just say~ing..." she lilted placatingly, "that you need to get laid!" I glared daggers at her but she ignored them without blinking an eye and bulldozed on with her inquisition. "I mean, c'mon. Your poor neglected pussy deserves better! You need to go out there and just, I dunno, let loose a little!" She leaned back against the window, finishing off her apple while regarding me thoughtfully.

Picking up her previous thread, she continued as if uninterrupted. Annalise had a tendency to be all over the place sometimes. Constantly being distracted by a new thought, she'd sometimes stop in the middle of a conversation to suddenly veer a hard left and jump into an entirely new topic. But eventually she always circles back. "Anyway. For real. Don't you ever get bored of just writing about it? Like, don't you miss it? Experiencing the real thing? Se-ex~?" She smirked, wiggling her eyebrows while holding her hands up and waggling her fingers to motion invisible quotation marks when she said "sex".

"For those of us in the know, I'm talking about that good 'ol penis in vagina action." She mimed insertion with her hands before proceeding to exaggerate sucking on an invisible cock. I couldn't help but smirk a little, appreciating the show. "'Cus you know reality's better than your fantasies, right?"

"I dunnoo, my fantasies are pre-etty steamy," I replied jokingly. "You should read them sometime. I think you'd be surprised." It was hard to suppress my grin as I smirked at her.

She crinkled her nose delicately in distaste. "I've seen some of the shit you write, you sick perv. Noo thanks."

I gave a little snort, amused by her quick judgment. "I write more mainstream stuff too, y'know."

"Oh yeah? Like what?" She didn't look convinced. I didn't blame her. I took commissions and have definitely received my fair share of odd requests.

With a little shrug, I leaned back in my chair, swiveling it slightly from side to side as I replied. "Hmm, like regular light romance or just vanilla but rough sex. Believe it or not, sometimes I don't even write about sex."

She cut in. "Threesomes? Gangbangs? Orgies?" She counted each word out on her fingers. Obviously she had no interest in any of my PG writing.

"And you're calling me a pervert?" I laughed. "Someone's obviously got a fetish" My joke was effortlessly ignored. It didn't stop me from smirking at her, amused by the whole situation. "Yeah, I write all of that. Is that what you're craving? To be the star of a gangbang?" I knew she'd take my teasing in stride. Between the two of us, Annalise was definitely the bigger slut.

"You know it'd be a lie if I said no. That's like, every girl's fantasy. I'm sure we've all thought about it at least once." I nodded in agreement, I know I'd definitely visited those waters occasionally myself while masturbating.

My eyebrows quirked up with interest at her next question. "Do you ever write any girl on girl action?"

I couldn't help but be amused by her open curiosity. "Yep. I write about gay couples, lesbians, bisexuals..." Like Annalise just moments ago, I was also counting each word off on my fingers. I was about to start listing out different relationship dynamics when she cut in with her next question.

"But have you ever been with a girl before? Like, for real?" I paused, surprised at the question.

She pounced at my hesitation. "Ah-hah! I knew it! You've never been with another girl before!"

"Actually..." I replied slowly, mentally weighing the consequences of my answer. "I have been with another woman before." I couldn't decide whether I should be offended by the surprised mix of skepticism and interest on her face. "But I don't see what that has to do with my writing. After all, I write gay porn too but I don't have a dick!"

"Exactly! You fraud!" Her impish smirk let me know that she was joking, but it didn't stop me from rolling my eyes at her. "But forget about that." Her voice dropped low as a salacious smile quirked the corner of her lips. "So, tell me," waving her mostly eaten apple around before bringing it back up for one last crunch, "how many times have you slept with another girl?" Her face was an open book and mischievous curiosity was dripping off its pages.

I squirmed in my seat, suddenly feeling self-conscious under the intensity of her inquisitive gaze. Seeing my hesitation, she tsked, clicking her tongue against her teeth. Rather than disappointment, cool indifference settled over her features as she nibbled at the rest of her apple. "I knew you were all talk."

"You didn't even let me answer!" I retorted, annoyed despite myself.

"Ooh? So you have slept with another girl?" Her eyes were practically sparkling.

"Ehh, not...exactly," I admitted sheepishly.

I should've known that her interest wouldn't wane. "I'm listening...~" It was clear that she wanted to hear every juicy detail.

Under Annalise's eagle eyes, I elaborated reluctantly through pursed lips, once again feeling awkwardly self-conscious. "It was during a party back in college. We met at a club near my university and spent most of the night dancing together. One of our drunken friends dared us to kiss and...we did." I shrugged. The end.

Or so I wished. "Uhm, no," Annalise protested. "Excuse me, but I'm going to need some details!"

"It was nothing special." I waved her excited look away dismissively. "He dared us to kiss and...next thing I knew she'd leaned in and...we...were kissing."

"Aand~?" I sighed, knowing that she wouldn't stop until she'd gotten all her answers.

"What do you want to know?" I leaned back in my chair, crossing my ankles while I thought back to that night so many years ago. It came back to me easily, the memories vivid in my mind's eye. "That her lips were soft and I could taste the mojito she'd had? That I remember the way we danced because I could feel her breasts pressing against mine while she ground her crotch against my thigh and all I could think about was whether she could feel how hard my nipples were against hers or how wet she was making me? That in between kisses that left us panting and breathless we'd be staring into each other's eyes but I have no idea what color her eyes actually are because it was so effing dark in the club? That we..." Ended up in the club's tiny restroom and our hands were so busy exploring each other while her mouth muffled every single one of my moans that I didn't even think to be bothered by how potentially disgusting the restroom was.

I blinked as I let my sentence trail off, catching the rest of my memories before I could voice the thoughts aloud. I wasn't quite ready to spill all the juicy details...yet. Glancing over at Annalise, I was surprised at the lack of immediate reaction from her. Rather than exclaiming 'AND?' as I'd expected, she sat in quiet contemplation.

"Let's go clubbing tonight," she suddenly blurted excitedly.

"What?" I laughed at the unexpected change of topic. "Uh, sure, I'll just go dig out my faux leather leggings and crop top from the bottom of my wardrobe and throw on my impossibly high four inch platform heels."

Annalise didn't appreciate my sarcasm and her frown said as much. "Well, why not?" she protested, somehow bristling and sulking all at the same time. "I mean, really. Do you even remember when was the last time you went out? 'Cuz I can't." She paused. "Or...is it that you don't want to go out with me?" Her face fell a little as she said this, looking so sincerely hurt and distraught that it cut my laugh short. .

"Whu-aat...?" My mind was having a hard time following this sudden turn of events. Annalise was a tease but she didn't seem to be messing around...? I decided to err on the side of caution. "What are you talking about? Of course I don't mind going out with you, I just...never go out!" I finished lamely, exasperated - at myself, at Annalise and this entire ridiculous situation.

I shifted uncomfortably in my seat, fidgeting through what felt like a long moment of awkward silence. My eyes flitted nervously away from her, only to flick back hopefully before quickly looking elsewhere again. It was a relief when she finally broke the silence.

"So you would go out with me?" She asked almost shyly, feigning nonchalance. I didn't see this side of Annalise very often. The softer, sensitive part of herself that she kept hidden beneath endless layers of wit and sarcasm. It made me want to hug her, she's so cute. It also made me want to tease her...

"Uhm, helloo? Pretty sure we just went out for groceries together the other day, or did you forget that? You still owe me for gas you know." I knew that wasn't the answer she was looking for, but I couldn't help it.

The apple core came flying towards my face so suddenly that I barely managed to dodge it in time. "Hey!" I yelled as I instinctively jerked away from the projectile. Admittedly, I probably deserved it.

"That's not what I meant and you know it!" Annalise was scowling, but it wasn't a cutesy teasing one. Was she seriously upset? The answer was clear when she got up from the window seat and huffily made a beeline for the door, her face scrunched up in a pouty frown.

"What? Hey, wait," I spun towards her, reaching out towards her half-heartedly. "Are you actually upset?" I gave a small laugh of disbelief. "C'mon, you know I was just kidding."

She stopped at the door, pausing at the threshold with her back to me. For a moment, I thought she was going to leave. But instead, she turned and looked straight at me, her hazel eyes held mine intently and I fought not to look away instinctively.

Too late, I glimpsed the barest flicker of a grin crooking her lips before it was gone again. Disappearing so quickly that it left me wondering if I'd seen it at all. Was this all an elaborate scheme of hers? Last time she'd somehow guilted me into trying out a hot yoga class with her. I was not about to let that happen again.

"Then kiss me."

I sputtered, stifling an incredulous laugh. "You can't be seri-..." My laugh died at the back of my throat as I noticed something flickering in her eyes, recognized the determined set to her chin.

Her lips pursed together at my laughter, her chin jutting out defiantly. I half expected her to turn on her heel and leave and I could see the thought turning in her mind as she considered it. But something else changed her mind. A smug, devious expression transformed her demeanor and she didn't even bother trying to hide it this time. Apprehension trickled down my back and I realized that I wasn't sure I was ready for that something else.

Dropping down onto her knees, she perched there, squatting on her heels, still looking straight at me. There was a slight moment of hesitation, but it was quickly replaced with a brazen boldness. She grinned meaningfully at me as she dipped down onto her hands before fluidly stretching into child's pose. She was the picture of a cat stretching languidly.

"If you don't believe me..." She let herself fall onto her side, still stretching lazily as if she'd just woken from a nap. She was lying halfway in my study, the doorway at her hips as her toes pointed and curled in the hallway. Once again, her eyes locked with mine and her hands started trailing down the front of her body. "I'll just have to show you..."

My eyes followed her hands, unable to look away because...I didn't want to. Instead, I watched as her fingers traced along the slopes and curves of her body. Teasing up and down her sides, up and down her torso from between the soft swell of her breasts to just above her pelvis. I watched, eagerly, as her hands cupped her breasts and I realized that she was braless as her fingers pinched her nipples through the thin fabric of her tank top, quickly bringing them to perky attention. I watched, greedily, as her back arched up off the floor as she pulled at the sensitive pebbles. Her little gasps and moans had me spellbound, sitting in rapt attention as I watched her writhe on the floor before me.

I choked down a little bubble of hysterical laughter - this all seemed so ridiculously surreal, I couldn't help but want to laugh. But the other part of me couldn't look away as one of Annalise's hands slipped down to her crotch. My breath hitched in a soft gasp, echoing Annalise's own gasp as her fingers pressed against her mound through her shorts. I found myself wondering if she was wearing any panties...

Entirely enthralled, I leaned forward without thinking, only wanting to get a closer look. My chair creaked loudly in protest and the sound startled the both of us. Lusty hazel eyes found my surprised gaze and all of a sudden Annalise was no longer squirming on my floor, moaning in quiet ecstasy. Instead, she was crawling towards me on her hands and knees with a predatory look in her eyes. She reminded me of a prowling jaguar on the hunt.

I felt a flutter of...excitement? anxious anticipation?...as I realized that I was her prey.

Again, I suppressed the urge to giggle madly. Part of me still couldn't believe everything I was seeing. But the other part of me was utterly enraptured and I couldn't tear my eyes away as the red-headed minx slunk across the carpet towards me.

I found my eyes drawn to the seductive sway of her hips, the outline of muscle along her toned limbs...I briefly glimpsed her swinging cleavage before my eyes flicked nervously away. Annalise's breasts were modest in size, but they looked so full on her slight figure that they seemed deceivingly big. Wait, why...was I...nervous?

I gave an anxious chuckle as I watched her prowl across the carpet, the distance between us quickly shortening. "C'mon Annalise, don't fuck with me." My weak protest fell on deaf ears. It only encouraged her smile to widen and her tongue flitted out to run along her teeth as she flashed another predatory smile at me.

As she closed half the distance between us with no indication of stopping, I instinctively pressed my legs together before leaning back in my chair with my arms crossed over my chest. I suddenly felt very...aware of myself. It was the way Annalise was looking at me - hot, intense and determined. I felt flatteringly wanted yet vulnerable at the same time, like a deer caught in the headlights - I was so surprised that I didn't know how to react.