Kelsie’s First Anal Experience

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Part I – Morning, Kelsie’s Apartment

“Andrew, hurry up we’re going to be late!” Kelsie called back over her shoulder. I walked quickly down the dark street, breaking into a jog as I struggled to catch up to Kelsie’s quickly disappearing form. As I ran, I glanced down at my bare feet quizzically, realizing I had forgotten shoes in my haste to get out the door. Where was Kelsie going? I ran faster, confused but now desperate to get to my girlfriend. Suddenly I heard the blare of a horn approaching from my right, turning and bracing myself for the impact of an onrushing vehicle that never came.

*Beep beep* *Beep beep*

Kelsie’s alarm chirped again as I swam from the depths of sleep, my heart pounding lightly in my chest as I realized it had all been a dream. I rolled over and cracked one eye open groggily, peering at the clock and seeing that it was only a few minutes after 8:00 a.m. Perfect, just enough time to catch up on a few more minutes of sleep before my girlfriend got home from the gym. On Saturdays, Kelsie normally left early for a seven o’clock cardio class at a workout studio just down the street, letting me sleep in before coming back to cuddle for a few minutes before we got ready for the day. I quickly hit the snooze button and rolled back into the pillows, closing my eyes as I relaxed back into the warmth of the mattress and my dream again took hold.

“Scoot over.” Opening my eyes at the sound of Kelsie’s voice, I lifted my face from the bed and saw her standing in the bathroom doorway, wisps of steam wafting around her tan form. Kelsie was a 5’6 brunette with a toned, athletic body, her ample tits balanced by a round bubble butt that turned heads every time she entered a room. At the moment she was stark naked, her shower-damp skin glistening and nipples hardening in the cool room as she settled down from her workout and hot shower. Kelsie leant forward, gathering her wet hair in one hand before wrapping it in a white towel and coiling it above her head to dry. At the sight of Kelsie, I felt my morning erection throb into the mattress beneath me. I rolled onto my hip, scooting down the bed and tossing off the covers so Kelsie could lay on her stomach next to me with her head resting on the pillows. “Mmm the shower felt good,” Kelsie said, her voice relaxing as she nestled into a comfortable position, “but I’m going to be sore tomorrow, I can already feel it in my ass.”

I smiled mischievously, “Oh yeah? I’ll bet you like that.”

Kelsie giggled, “Shut up, you know what I meant. And for the record, before you even say anything, no I don’t want to feel anything of yours in my ass!”

I leaned in and kissed her hip softly. “Are you sure? You could have skipped the gym this morning babe, I would have been more than happy to give you a butt workout,” I said with a stupid grin as I reached to jiggle her firm, toned ass with one hand.

“Oh haha, super original. I’ll bet you would; you’re always trying to play with my ass, it’s like you’ve developed a kinky side.”

“You just have such a nice ass. I can’t help it.” I sat up and swung one knee over Kelsie’s outstretched legs to straddle her thighs, yawning and rubbing my eyes blearily before I reached to grab a bottle of moisturizing lotion from Kelsie’s night table. Squeezing a glob into my palms, I rubbed my hands quickly to warm the cool liquid and reached down to palm both of her rounded asscheeks, my erect dick straining upwards against my boxer briefs.

Kelsie raised herself on her elbows, looking back over her shoulder as I began to massage her round butt with firm circular motions. “I have to admit, it does look pretty good,” she laughed, “all of those damn squats are paying off I guess. My ass is gonna be HUGE before long. You’re pretty lucky,” Kelsie teased, sticking her tongue out at me.

“I know how lucky I am to have you, Kelsie,” I said sweetly, still smiling as I surprised my girlfriend by pulling one firm asscheek to the side, exposing her swollen pussy lips and the puckered skin of her asshole. I slid the index and middle fingers of my other hand slowly upwards from the mattress towards Kelsie’s perineum, feeling the warmth emanating from her core as I teasingly spread her pussy lips and brushed against the edge her tight asshole with my fingers.

“Hey!” Kelsie squealed, slapping back at my hand and scooting forward involuntarily. “Nice for you to look at, but not to touch! And don’t even start getting any ideas,” she said, her green eyes alighting on my cock as it strained against my boxer briefs. “You’re *definitely* not putting your dick in there.” On cue, my hardening cock throbbed again, fully erect and tenting my shorts uncomfortably.

“Hmmm are you sure?” I teased, rubbing my bulge gently as Kelsie gazed at me, biting her lower lip. “You might like it. You don’t mind when I massage your butt.”

“Hmmm,” Kelsie sighed, subconsciously running her tongue around her lips before turning to settle back into the mattress as I resumed rubbing the soft skin on the backs of her upper thighs. “I guess you’re right. Fine, new rule: you’re allowed to use your hands.”

“Ok çeşme escort good,” I joked, digging my fingers in to knead her firm flesh. “So just my fingers in your ass then.”

“Shut up and keep massaging,” Kelsie grunted into the pillows, wiggling her ass back at me.

“Don’t tell me you’ve never even thought about it,” I persisted, squirting more lotion onto Kelsie’s legs as I began to work it into her supple skin. “The girl in that video you wanted to watch last night was begging to get fucked in the ass.”

I had been teasing Kelsie about trying butt sex all week, after she had let inadvertently let slip that watching anal porn turned her on when she was feeling kinkier than usual. The night before we had hooked her Apple TV up to the living room television, streaming porn while Kelsie blew me lazily before finishing in a steamy fuck with Kelsie bent over the couch. Kelsie and I normally watched lesbian videos when we were together, both turned on my the sight of two gorgeous women pleasuring each other in front of a camera, but last night Kelsie had pulled up a video of a petite blonde taking it in the ass from her partner as she used a sex toy on her clit.

“That’s just porn!” Kelsie exclaimed, lifting her head. “I mean, I’ve heard it makes you cum like, incredibly hard, but I’ve always been too scared to try it.”

“See? You’d definitely like it!” I replied cheerily, again spreading her cheeks and gently sliding my thumb along the forbidden skin around her asshole. Kelsie moaned softly but didn’t pull away at my touch.

“I don’t know,” Kelsie said, looking back at me and wrinkling her nose as she appeared to actually consider my suggestion for the first time. “Hannah’s done it. She told me the first time was awful, but now she lets her guy buttfuck her all the time apparently.”

“Wait really?” I mused, squeezing Kelsie’s butt as I pictured her friend Hannah on all fours with a guy buried deep in her ass. The image did little to relieve the painful ache in my balls, as Kelsie’s firm bubble butt and our conversation had me incredibly turned on even before Hannah entered the picture.

“Ok ok, we’re stopping this conversation now.” Kelsie said, rolling over and sitting up to face me, patting my erection through my boxers. “I need to get dressed to meet Hannah and *you* need to get in the shower if you’re going to make it to your meeting today,”

“Come onnnn,” I groaned in protest, “don’t leave yet!”

“Oh stop complaining,” Kelsie said, poking me in the ribs as she clambered from the mattress to begin dressing. “If you’re lucky, maybe I’ll let you look at my butt again tonight.”

Moving from the bed, I resignedly grabbed some of my work-appropriate clothes from Kelsie’s wardrobe and walked into the bathroom across the hall, turning on the shower to warm while I brushed my teeth and strained to pee through my insistent hard-on.

Stepping into the large, glass shower enclosure, I left the door ajar to release the steam and stood under the showerhead, letting the spray machine-gun into my chest as my engorged cock bobbed angrily in front of me. I quickly soaped myself up, taking a few minutes to relax under the massage of the warm shower as it hit my scalp before rinsing off. As I showered, the bathroom door opened and I heard the clicking of Kelsie’s heels on the tiled floor as she stepped inside, moving to stand in front of the vanity where she fixed her hair and applied a brief touch of makeup in the mirror. “Hey babe,” I called, “sure you don’t need another shower?”

Kelsie poked her head into the open door to the shower stall, her brown hair now falling in glossy waves around her shoulders. As her eyes alighted on my throbbing erection Kelsie broke into a cheeky grin. “Sorry babe, but I have to go.” Kelsie raised her voice slightly over the noise of the shower, “I didn’t realize you were so worked up this morning. Why didn’t you say something?!”

“Wait, so you’re really going to leave me like this?” I whined, gesturing at my engorged cock, “come on the shower feels great.”

“Hmmm that sounds nice but I think you’re on your own with that one!” Kelsie laughed. “I’ll see you later, don’t work too late and we can cook together tonight.” Kelsie winked, pulling the shower closed before she exited the bathroom and shut the door with a click.

Groaning in disappointment, I reached down and grasped my thick cock, sliding my hand along my shaft and visualizing Kelsie on her knees in front of me. I hadn’t jerked off in several days because I had spent the weekend with Kelsie, but I had several hours worth of documents to get through this afternoon at the office and I desperately needed to cum first if I was going to get anything productive done later. Closing my eyes, I stroked myself firmly, picking up the pace as I imagined Kelsie on the tiled floor tugging at her own nipples as she forced her head down onto my cock. I felt a familiar ache in my balls as my orgasm approached, my right hand now a blur on my dick. Urging myself towards release, I thought back to the night before, picturing Kelsie bent over the couch, escort çeşme her moans echoing loudly through the house as I pounded into her tight pussy and roughly pawed at her tits before erupting inside of her.

My orgasm hit with a sudden rush, warmth shooting up from my balls as cum spurted from my cockhead to land on the shower floor before swirling thickly down the drain. With a few final strokes, I coaxed the remainder of my orgasm from my dick and caught my breath before cleaning my hands and turning off the water. Grabbing a towel from the rack, I dried myself and pulled on a pair of grey slacks and a crisp, white oxford shirt, pausing to check my reflection in the mirror as I headed for work.

Part III – The Office

*Bzzt bzzt* *bzzt bzzt*

My phone buzzed on the desktop, a lock-screen alert notifying me of a new iMessage from Kelsie. Grabbing my phone, I noticed that it was already after 7:00 p.m. “How did it get so late!?” I wondered briefly, disheartened but unsurprised. Work had been like this lately. I had arrived at the office intending to work for a few hours and leave around 5:00 so I could get to the grocery and grab food for dinner, but I had apparently lost track of time as I worked steadily throughout the afternoon and hadn’t realized when the daylight faded and the chill evening took hold. I shook my head wearily, opening my texts to read the most recent message.

“Want to see what I bought today?”

“Yes pls” I responded, my mood already improving.

My phone buzzed again almost instantly.

I quickly opened the attachment, inhaling sharply at the image of Kelsie and Hannah standing side-by-side in a floor-length mirror, their hips touching, as Hannah’s right arm wrapped around Kelsie’s waist to cup her hip and she held her phone camera towards the mirror in the other. Both girls wore matching royal blue high-cut bikinis, with the straps of Kelsie’s top untied to hang loosely down from her shoulders as she cupped both breasts shyly in her hands. Gazing at the picture closely, I zoomed in on Kelsie’s chest, noticing that she appeared to be tugging slightly at her right nipple, green heavy-lidded eyes giving away her barely-noticeable arousal. I shifted uncomfortably in my desk chair as blood surged to my groin.

“!!” I texted, “god Kelsie you’re so hot.”

“Want to see more? I might have gone a little overboard at the mall.”

“Damn, Kelsie,” I thought to myself, adjusting my growing erection to rest more comfortably in my pants. How was I supposed work like this? Already giving up on the thought of getting anything else done, I replied to Kelsie’s message: “You know I do.”

My phone buzzed for a third time with a new picture and text message. The photo Kelsie had sent displayed a closeup shot of her rounded ass with the thong back of her new bikini bottoms wedged deeply between her cheeks. “Come over. I’m getting hungry and you’ve been working all afternoon!”

Shaking my head quickly, I briefly attempted to refocus on the word processor document in front of me. There was no way I would be able to concentrate distracted by the thought of Kelsie and Hannah’s alone time together earlier today. Quickly giving in to Kelsie’s unspoken desire, I hastily typed up an email to the partner assigned to review my filings, tossed my laptop in my bag, and texted Kelsie back as I grabbed my keys and headed for the door. “On my way.”

Part IV – Night – Kelsie’s Apartment

“I’m getting sleepy, let’s go to bed.” Kelsie stood, stubbing out the remainder of our shared joint and bending forward to stretch her lower back.

Taking her lead, I grabbed our wine glasses and opened the sliding-glass patio doors to head inside, stepping through the living room towards Kelsie’s kitchen. Kelsie followed me in with the empty champagne bottle and our plates, depositing them in the sink before locking the front door and dimming the lights. She stepped back into the darkened kitchen to stand in front of me, taking both of my hands in hers. “That was delicious,” Kelsie smiled up at me, “thanks for cooking tonight.”

“Of course,” I replied, “We don’t cook here often enough, I love hanging out with you like this.”

“Suddenly you’re full of compliments when we’re about to get in bed, somebody’s trying to get laid!” Kelsie teased, smirking at me slyly.

I rolled my eyes. Kelsie had been teasing me all day. “Don’t act like you didn’t plan this. Since when would you have all the ingredients for dinner in your refrigerator? Or the champagne you just happened to have on ice? Or a pre-rolled joint, or…” I went on, “you’ve been planning something special for tonight! Ooh I know…” I teased her, grinning devilishly, and squeezing her hands, “are you trying to seduce me to get me to fuck you in the ass?”

Kelsie laughed. “Oh my god. Don’t even start or I swear you’re not getting anything tonight.” Kelsie’s smile softened into a seductive grin, wordlessly communicating that she needed me to take her soon.

I pulled Kelsie into me for a deep kiss, slipping my tongue between her lips to run along her small, çeşme escort bayan even teeth and nibbling softly on her lower lip before planting a trail of kisses from her collarbone up her neck, stopping to bite gently at her earlobe as my hands roamed up and down her back. Kelsie inhaled deeply, pressing herself into me and reaching down to grasp my swelling shaft through my pants as I licked at her ear.

“Come on.” Now taking the lead, Kelsie guided me down the hall towards her bedroom. As we reached the bathroom, Kelsie let go of my hand, stopping in the doorway.

“I’m gonna get ready for bed, wait for me?”

I kissed her again. “Of course.”

Stepping into Kelsie’s room, I flipped on the lights and unbuttoned my dress shirt, tossing it onto a nearby chair and quickly stripping out of my slacks and socks. Turning down Kelsie’s bedcovers, I plugged my phone into a bedside outlet and lay down, lazily scrolling through Instagram as I waited for my girlfriend.

“Hi…” A soft voice greeted me from the doorway a few minutes later. Kelsie entered the room, dark brown hair down around her shoulders and wearing a short, sheer black nightgown displaying her fit legs and the deep v of her tanned cleavage. The bedroom light seeped through the thin material as it clung to Kelsie’s tight body, shadows outlining her well-defined abs and toned thighs. Pausing just inside the doorway, Kelsie dimmed the lights and turned for me, lifting the back of her skirt as she spun to show me that she was completely bare under the sexy lingerie.

Blood surged to my cock as I felt myself instantly straining against my boxers. “Damn Kelsie, you look amazing.”

“Hmmm good,” she purred, “I thought you’d like it,” Kelsie softly trailed her hand across her chest, stroking her hardening nipples through the silky gown as her other hand moved to her crotch. “I saw this while I was shopping today and couldn’t wait to wear it. Just putting it on makes me want to fuck you.” Kelsie paused, reaching to lift her skirt slightly and allowing me to glimpse her clean-shaven pussy as she slid her index fingers between her protruding pink lips. “God I was so horny while we were shopping, you have no idea.”

Moving to sit on the edge of the bed, I extended my arms to Kelsie, grasping at her greedily as she stepped forward and leaned down to kiss me. Kelsie’s lips parted, her warm tongue snaking into my mouth as she grabbed the back of my head and pulled me up towards her.

“Tell me about it.” I murmured into Kelsie’s lips as I stood, knowing she enjoyed talking about her fantasies when she needed to get fucked. With one hand I reached beneath her dress to stroke her wetness.

Kelsie hissed in pleasure. “No, I don’t want to talk. Undress me.”

Wordlessly, I moved to stand behind Kelsie, placing both hands on her shoulders and bending her forward as I kissed the back of her neck softly. Kelsie’s breath quickened, her smooth skin breaking into tiny goosebumps at the feeling of my hot lips and tongue against her neck. Pushing the straps of Kelsie’s lingerie from her shoulders, I slid the thin material down her torso to bunch at her hips before tugging it over her rounded ass and allowing it to drop to the floor.

I trailed my hands lightly down Kelsie’s back and grabbed her by the hips, pushing her forward to slide onto her knees on the mattress. Tugging her back towards me, I positioned Kelsie with her feet hanging off the edge of the bed, pushing her head down so she lay with her large tits smashed into the sheets, already moaning softly in anticipation. Spreading Kelsie’s legs, I knelt on the floor and leaned in to kiss the back of her thigh as I used one hand to rub along her swollen pussy lips. Extending my tongue, I moved to lick Kelsie from bottom to top with one long, slow stroke, eliciting a loud gasp.

Now burying my face in Kelsie’s crotch, I stuck my tongue out and licked her wetly, grinding my bearded chin into her sensitive pussy as Kelsie’s musky scent filled my nose and mouth. As I continued to eat Kelsie’s delicious pink slit she spread her legs slightly farther apart, reaching back to rub small circles on her clit.

“Fuck your tongue feels good,” Kelsie rasped. “Ungh. Finger me.”

I pulled back, firmly grasping Kelsie’s ankle in one hand and quickly wetting the fingers of my other hand with my tongue before reaching to finger her. I teased at Kelsie’s pussy lips with my index and middle finger before slowly thrusting into her, her slick pussy gripping me tightly. Bending my fingers, I worked my hand in and out, scraping firmly along the sensitive spot just above the inner wall of her vagina.

Kelsie moaned, her legs twitching. “Oh my god your fingers feel so fucking good, keep doing that.”

Twisting my hand to rotate my fingers inside of Kelsie, I stood up, grabbing her by the left hip and pulling her back against my hand as I picked up the pace. Kelsie groaned, reaching to pull her hair up off her neck and over her head, her entire body shuddering at the feeling of my fingers sliding in and out of her. Letting go of Kelsie’s hip, I reached to spread her ass, leaving the fingers of my hand inside of Kelsie’s pussy as I placed my thumb on the skin between her slit and asshole. Slowly, I lightly stroked my thumb up and across Kelsie’s hole, causing her asscheeks to quiver and her pussy to clamp down suddenly on my unmoving fingers.

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