Anal with Georgie

"Damn," Georgie said.

"What?" I looked down at my painfully hard member. It was swollen and angry with desire.

"It's just... I just wasn't expecting..."

"You've seen my penis before, haven't you? You seem to have no problem walking in on me when I'm peeing."

"But that's not how it looks when it's... damn." She swallowed, "I'm not sure that's going to fit."

"Oh," I began to tug my shorts back up.

"No," Georgie stopped me, "It's okay. It's just... Damn. I didn't know that's what you were packing, Johnny. Well done, sir." She tipped me a quick two-fingered salute.

"Thanks," I shrugged slightly self-consciously. My hard cock was an inch away from brushing her bare thigh.

"I'm glad I can confirm all the shit written about you on the walls of the girl's bathroom isn't true."

"What stuff? Wait, never mind, that can only be Sally. She's such a bitch. Well, the stuff written about you in the boy's bathroom definitely is true. You do have the best ass in school. Probably on the planet."

"Really, tell me more." She shifted her weight coquettishly, drawing my attention back to her bottom.

"That's about it. It's not a poetry corner, George. I mean, some of it rhymes, and the imagery is quite vivid, but I won't repeat it in polite company. Suffice to say, there are a lot of guys who would literally kill to be where I am now." While I was talking I realized that I'd started stroking my dick. When I saw Georgie's intense gaze fixed on my cock head, bottom lip being gnawed between her teeth, I stopped, my face suffusing with heat. I'd just realized that under normal circumstances she'd basically just caught me jerking off, to her naked backside no less. But these were anything but normal circumstances.

"So... We gonna start this?"

"I guess," It was my turn to swallow hard, feeling like this was my first time all over again. In so many ways it was. "How do you want me to start?"

"Maybe some lube? I didn't bring it just to be the centerpiece for our debaucherous little picnic."

"Okay. Um, how do you want me to..."

"I don't know, John. Use your imagination."

"Okay," I willed my shaking hand to steady. I reached out and placed it on one broad, pale cheek. She closed her eyes. Her skin there was several degrees cooler than the rest of her body. With my other hand I picked up the lube. Mom's lube. Gross. I turned it over in my hand. This was not rocket science. Just a simple application. I could do this. I popped the lid. Clear gel oozed out before I'd even squeezed it. I scooped it up with a finger. I stared at the shiny glob, then down to Georgie's asshole. It winked at me in nervous anticipation.

Carefully I reached out. The moment took an age. Then, like the kiss of a butterfly, I touched the lube to the ring of her sphincter. Georgie gasped and jerked forward. I paused but she rocked back and I found my finger pressed to her asshole. Hot, slippery, and tight as a drum.

"Fuck," I breathed the word out long and low. My finger daubed a circle around her pursed sphincter. "You okay?" I asked.

"All good. Are we doing this?"

"We really are," I gritted my teeth and let the tip of my finger slip onto pinprick in the heart of her anus. I began to apply pressure. Georgie sucked in a breath and arched her back but she did not stop me. I increased my pressure and, gradually, the tip of my finger crept through the constricted purse. My digit sank deeper and deeper into her warmth.

"Christ," she winced, "Are you sure that's just your finger? You haven't got a baseball bat back there?"

"That's just the tip."

"Damn. I'm starting to wish that what Sally wrote about you was true. I'm not sure I can take that thing of yours."

"Just relax," I soothed, carefully dipping my digit in and out of her. Gradually, with measured probing, I began to loosen her up. She shifted her weight to spread her legs a little wider. By the shortening of her breaths, I surmised that the experience was beginning to improve for her.

"What are you doing?" Her question came out surprisingly husky.

Puzzled, I looked down to see what she meant and was surprised to find that the hand I was not fingering her asshole with had crept up to cup her pussy.

"Um," I was not sure how to answer, "Sorry, just an instinct. I forgot you were... we were... never mind." I pulled my hand away and only then became truly aware of her by the absence of heat.

"No," She gave me a bashful look, "you don't have to stop. It felt... It felt kind of nice."

"You sure?" I paused the retreat of my hand, "It's not taking things too far?"

"Your finger's in my butthole, John. That's pretty damn far already. Besides, I think it's helping me to relax a bit. Maybe you could do a little more?"

"Sure, if it's helping." I let my hand creep into the supple flesh between her thighs. The folds parted and my fingers found liquid heat. It was like tapping the bark of a maple. Desire oozed out of her, slicking my fingers and making them slide with near-frictionless ease over her skin. I explored her thick flaps and swampy inner recesses while my other finger toyed her asshole ever wider.

"Okay," a while later her voice surprised me out of my focused attention. I was almost disappointed, I'd really been enjoying teasing her holes.

"Yeah?" I asked, a fist of excitement clutching my throat.

"It's now or never. Just make sure you use a lot of lube."

"I will," I growled. I pulled my finger free of her bowels a little too eagerly.

"Hey!" She squawked, "Did you just finger pop my asshole?"

"Maybe."

"Don't take too many liberties back there."

"Sorry," I offered a regretful grin but wasted no time in getting the cap off the lube. First, I couldn't resist rubbing her slippery juices all over my cock. Only when my dick was shiny and I could smell her scent all over me did I squeezed a slug of clear gel onto my dick. This I smeared up and down my length until it glistened in the midday sunlight. I shifted back into the shade and poised on my knees behind her. Georgie was watching me apprehensively through a curtain of her dark hair.

I gripped my cock and stared at her closed asshole, doubts creeping into my chest. "So, do I just...?" I shrugged. My free hand held her ass in place.

"I don't know any more than you, bro. Let's see what happens."

"Okay," I took in a sharp breath, "Here goes." I carefully lined my pulsating tip up with her petite, pink starburst. I let my head kiss her already well-lubricated hole. I felt her muscles go tense as she prepared for the invasion of her body. Slowly, ever so slowly, I leaned into her. My cock pushed a deepening depression into her soft skin. I caught a grimace on her face. But, though I increased the pressure to the point where my cock started to bend, I failed to pierce her impossibly tight hole.

"Mother fucker!" She grunted.

"Sister fucker actually," I corrected but, sensing Georgie's growing discomfort I withdrew. "But you know what they say: 'It's all relative."

This earned a laugh from her, despite her red-face pain. I let her relax and, seeing her give a brave nod, I reset myself and tried again.

Again I was repulsed by her body. I was so close. I sensed that if I just forced it an extra half-inch I would breach the barrier and be inside her. I ached to do it, but this desire was outweighed by my love for Georgie. She was putting a lot of trust in me here and I was not going to let her down.

"Sorry," Georgie gave me another pained expression after our second failed attempt.

"Hey, don't worry about it. I'm not sure it's going to work George. We can stop if you want?"

"Maybe one last try? You're just too damn big, John."

"It's my burden to bear," I lowered my head in mock resignation. While I was looking down I had a thought. Playing with her pussy had helped relax her the first time. I couldn't hurt to try again. It was such a juicy pussy, so tender to the touch. It really would be a waste if I didn't pay it a little more attention while I had the chance.

I brushed the smooth folds with my fingertips. I waited to see if there was any reproach, but she only tilted her hips up a minuscule amount to improve my access.

"That's it," I soothed, as I stroked through her sleek, sticky cleft. She widened her stance again and pushed out her magnificent buttocks.

"You're... pretty... good at this," her words came out in little pants.

"Thanks," I grinned, feeling genuinely complimented, "Are you feeling more relaxed?"

"I feel... really... really good."

"Ready for one last try?"

"Shove it in there, big boy."

I laughed, "Do me a favor, George. Don't try to talk dirty. I can't take you seriously."

She laughed too and, as I lined up for my final approach she grunted, "Go on. Stick that fat dick of yours in my tight little virgin asshole. Do it, brother. Fuck me good."

"Stop," I chuckled, "I need to concentrate." I pushed my plum-sized head against her sphincter again.

"Do it," she said through bared teeth, the irony fading from her tone, "Shove it in. Own your sister's tight butt."

Comical as her words should have been, they were having an effect on me, driving up my hunger and animal lust. I forced myself harder and deeper. The skin above her fleshy pussy lips concaved in deeply where I was driving in my shaft.

"Fuck!" She cried out, "Don't stop. You're... almost there... just another..." She squeaked as the resistance suddenly gave and I plunged two inches into her body. Her ring turned a deep pink and looked painfully stretched around my girth.

"Oh. My. God!" I bared my teeth at the sky, eyes closed in sheer ecstasy at the pleasure that engulfed me. She was so tight and warm. My dick felt like it was in a vice made of warm, rubbery flesh.

Georgie was faring less well. She winced and buckled forward. Her body taking strain from the sudden, oversized intrusion. She cursed again.

All I wanted to do was push in deeper, to sheath my entire length in her and feel her body encase mine. But I was too aware of her distress. I tried to keep her calm by rubbing circles in the mushy flesh of her cunt. I held myself there, just barely inserted into her cramped back passage, and asked, "You okay, George?"

"I... will be. Christ, that is big. It should come with a health warning. Just give me a minute."

I considered her for a few seconds, her hunched-over body, the pained expression on her face, and I knew I didn't have it in me to hurt her further. "I think that's enough for today, Georgie," I announced.

"No," She gasped, "I'll get used to it, just give me a few seconds... Goddamn, that smarts. Do they hand out medals of valor to pornstars? Because they should."

"Yeah, no. Forget it. I'm pulling the plug," I knew I was making the right decision when she didn't rise to even that blatant innuendo. Her body clung to me and I had to lever myself out of her. I came free with a pop and her asshole snapped shut. I wondered how I'd even fit in there in the first place. My poor cock was swollen purple and dripping with precum and lube.

She stayed like that, upper body flat to the blanket and her ass up in the air. She had her eyes closed. I gnawed on my lip. I should have known that this would end awkwardly. It had to. What were we thinking? I was racking my brain for a way to salvage things when I realized that my hand was still nestled in her pussy, massaging soothingly into her soft folds. She was quite plainly enjoying this, the pain gone from her face and a little smile tweaking up the corner of her mouth.

"You okay?" I asked.

"Mmm," She hummed drowsily.

"Maybe," I started, balked, then tried again, "Maybe we can try your thing instead?"

"My thing?" She pouted. We could both hear the slosh of my fingers inside her crevice.

"Yeah, you know. The cockpit."

"Cockpit," she giggled softly. That was a good sign.

"Someone you can guide and control..."

Her eyebrows raised. I knew that meant that she liked the idea. "You seem to be doing a pretty good job already."

"I could do better," I offered. "I want to do better. Maybe if you roll over. I can... and you can tell me what to do."

One eye opened and watched me carefully from its corner. Her smile grew languidly across her face. Her body began to move, lithe and slow like poured honey. I supported her as she rolled over onto her back. Her tits jostled, still cruelly holstered in their bikini cups. Her legs fell open and I was greeted by the sight of her incomparable sex spread before me. The thickness of her thighs and ass served to push her plump pussy up and out. It was like a tulip just before it opened, a ripe bud of perfection and it was shiny with oily desire.

"God, I want to kiss your pussy," the words came out fast and unexpectedly. I hadn't intended to say it aloud, but Georgie did not look displeased.

"At least you won't have to worry about getting pubes stuck in your teeth," she grinned, enjoying the effect her display was having on me. She was not mistaken. Her pronounced mound above her sex was shaved perfectly smooth. It had a healthy bald sheen even in the shade. No pussy had ever looked so inviting.

She smiled and placed a careful finger in her slit. She drew a line upwards and came to a stop where the thick folds of her labia parted to reveal the oyster perfection of a fleshy hood.

"Here," she cooed softly. I licked my lips. I couldn't resist. I dove in. The first kiss was unlike any kiss I'd ever experienced. It had all the heart-thumping, skin-tingling thrill that felt like falling in love should, but with ten-fold the impact. Georgie moaned loudly as my lips made contact with hers.

She was so wet it was like eating a freshly peeled mango. Juices ran into my mouth and dripped off my chin. I drank from her like she were wine of the finest vintage.

"Mmm, that's it." She breathed out as I let my tongue slide up the channel of her cleft. "A little higher. Yeah."

I played with her at first, kissing and tonguing my way through her folds like I was working my way through a particularly engrossing book. With her guidance, I probed her tenderest parts and gradually zeroed in on the nexus of her pleasure. This was one time I barely needed the help though. When I reached her clitoris I found it sitting up, begging for attention. It was swollen as painfully as my cock and palpating with desire. Georgie was even more into this than I suspected. Had she been harboring the same secret desires I felt for her for so long? I began to tongue her clit and felt grateful to have such an honor.

Georgie moaned and writhed while I lapped at her sex. Her hands dug into my hair and, using a combination of this direct puppetry and some vocal suggestions, she guided me exactly where she needed me to be. She conducted my tongue, lips, and fingers like they were the sections of an orchestra.

Soon her voice came in rising cries of pleasure as I licked her clit with robotic precision. At her instance, I shoved first one and then two fingers into her slurping entrance. Together we nurtured them into the perfect pace and depth of thrust, even adding accents with the slight twist and curl of my fingers. Her vagina felt as tight as her asshole and I wondered, not without a heart-clenching thrill, what I would feel like to squeeze my dick into it.

Tongue rolling like a tide, fingers pistoning in and out of her, I lifted her up, up, up. Higher than any heights she had known before, taking her to where the air grew thin, to where she could hardly breathe, and still I took her higher. I was now hunched over between her legs, which she'd thrown as wide apart as she could, and working with a manic intensity on her pleasure centers.

Her body was wracked. It convulsed spasmodically. Her eyes and mouth were open, her expression the blank stupor of mindless bliss. Her muscles did not know whether to contract or relax and they tortured her body with unsyncopated combinations of both. She was at the very edge of the atmosphere, floating. Poised between heaven and earth, the curvature of the Earth arcing beneath her feet. Her chest floundered as it tried for air but found only vacuum. Then, with one last, long slither of my tongue, which danced along the ridge of her aching clit, she fell.

Gravity asserted itself in a jealous rage. It pulled her screaming back down toward the ground. Her muscles locked, her body began to shake uncontrollably, her hips bucked up off the blanket into my face with bruising force. Her climax was a freefall of whirling, spinning madness which left her disorientated and slightly alarmed by its intensity. Still writhing it out, she grabbed my head in her hands and held it while she smeared her spasming sex back and forth across my face. Each movement seemed to eke out another magnitude of pleasure from her until relief from the divine pleasure finally came as she slammed back down to earth with bone-breaking force.

She lay in a crater of her own wide-flung hair and bodily fluids, with me still buried face-first in her splayed sex. Her lungs were working like a set of punctured bellows. I languished in the taste and scent of her, coaxing the last few dying shudders from her spent body.

"Wow!" She cried out joyously, when she managed to get enough air into her lungs, throwing her arms back over her head. "I mean, Wow! Fucking, Goddamn, Hells Bells and a cherry on top!"

"Good?" I looked up, my dripping chin bumping against her messy pussy.

"So fucking good. The fucking best. Why wasn't I doing this before?! Why weren't we doing this before? You have a fucking gift, Johnny. Sally is a total bitch, and an idiot. Shit, that tongue of yours should have been winning awards back in school."

"Well," I shrugged off the compliment, "I had some help. To be honest, it's never been like that for me either. I mean, don't get me wrong, girls have 'agreed' with before, plenty. But not like that. Never like that. You really fucking agreed with me there."

"Fuck yes I did."

I crawled up the blanket and flopped down beside her on my back. We were both shiny with lube and her juices. My poor cock looked like it was competing with the oak tree for height dominance. Suddenly, I felt my heart hitch in its beat when I turned my head and found her depthless eyes staring into mine. It should have been awkward, I'd just had an anal sex fail and eaten out my sister's pussy, but it wasn't. It was never awkward when I was around Georgie. The locked gaze, the silence broken only by the hum of insects, all of it felt comfortable. There was a dozy warmth to the afternoon. Georgie reached out a hand and placed it on my chest. I let it lay there. My cock gave a painful twitch.

Her thick lashes did a slow sweep across her brown eyes. "I feel kind of bad now," she said.

"Why?" I gave a short laugh.

"My dream came true, but yours didn't." Her eyes darted down to my straining erection.

I shrugged, "This was a whole other kind of dream, Georgie. Totally unexpected and all the better for it. Don't feel bad for me. Feeling you come on my face like that," I blushed when I realized what I was saying but finished with, "It was fucking amazing."

Her fingers made a slow spider crawl on my chest, without actually moving. I was looking up into the leaves of the oak tree but, when I looked back I saw her bottom lip was pinched between her teeth.

"What?" I asked. Enjoying the cool breeze on my bare shaft and balls.

Her eyes darted nervously to the side before she spoke again, "Maybe..."

"Yes?"

"Maybe we could try one more time?"

My heart nearly punched a hole through my ribcage. Georgie was now drawing circles in my unmanly tufts of chest hair. "We don't have to, George," I shook my head, "Maybe Forrest Gump was wrong. Maybe life is not like a porno."

"I'm pretty sure he said something else," she giggled softly. The sound made something flutter in my belly. It had never done that to me before.