Anal with Georgie

It has been pointed out to me that there are two big problems in my relationship with my sister. The first is that we are too close. Too close in age, too close in habits, and too close in interests. She is my twin and we have been inseparable pretty much since birth. Our mom says that even as babies we used to howl if they tried to put us down to sleep in separate rooms. They've tried everything; setting us up on separate playdates, attempting to send us to other schools, and even sitting us down with a psychiatrist. None of it worked. We can't help it, we just really like each other's company. No one gets me like Georgie does. I understand it makes us a bit weird, but I can't make myself care.

The second problem, apparently, is that we share too much. Brothers and sisters are supposed to develop a natural propriety, or so we've been told. They're supposed to bond with classmates of their own gender and share their secrets and desires with them. Again, I don't get that. My sister is the one person I know I can trust absolutely. Georgie and I tell each other everything. We told each other about our first times and we still laugh about the failures and triumphs of our love lives. One of my girlfriends told me that I will never form a long-term relationship as long as I remain so attached to my sister. But, as I told her then, "If you can't deal with my relationship with my sister then we're not meant to be together."

That being said, Georgie and I had never been anything more than best mates, despite some of the commentary and speculation that was directed our way in high school. That all changed in the vacation before we went off to college (Yes, the same college, despite our parent's best efforts).

We were outside on the lawn on a big tartan picnic blanket Georgie had laid out in the shade of the huge oak. The tree was a special place for us. During our childhood it had been a castle and a tall tower in which a fair maiden was trapped (If I told you that I always played the fair maiden, perhaps you will understand Georgie a bit better). It was a shop, a space rocket, a haunted forest, and, on more than one occasion and in a moment of desperation, a bathroom (Georgie again. And me. But, mostly Georgie).

On that day it was just the coolest place in the garden. It was warm with a sky as clear as a polished lens. We'd placed the blanket half in the shade and half in the sun so that we could intermittently work on our tans. Our grandpa often told us the story of how he'd fallen in love with our Abuela while on holiday in Mexico and brought her back with him. We had her to thank for the way we could both pick up a cover model tan in a few hours. I also had her to thank for my thick, dark eyelashes, and Georgie, as she always put it, kept her south of the border, "south of the border." In the cutoff jean shorts she wore today that big, round ass of hers looked especially good. Good brother that I am, I made sure to tell her. She slapped my thigh playfully and grinned her wide grin back at me.

The only other bit of clothing she wore was a white bikini top so brief her breasts threatened to bubble over. Yet I was perfectly at ease, shirtless and lying so close to her our skin brushed when one of us shifted even slightly. This is the way we'd always been with each other. Comfortable.

We could hardly be blamed for being close. We had grown up on a farm about ten miles outside the nearest town. Apart from the other kids when we were at school, we had been each other's only playmates for most of our childhoods. Dad worked in the dairy and surrounding fields all day and, since we'd started high school, mom was back working again in the accounts department for the biggest tractor dealer in town. So, the farm was our own private universe.

Of the two of us, Georgie was the farmer. She was going to take over the running of this place one day. We'd agreed on that without ever saying the words before we were even nine. She wanted the college experience though and was studying something in agricultural management. I was, to be honest, terrified of the thought of college. I was going along with Georgie purely because I had no idea what else to do. I didn't want to miss out on doing anything with her. So, we would share accommodation while I studied the most general degree I could find and prayed inspiration would strike. This would be our last vacation before I had to face that reality and with each day that passed my anxiety grew.

It was easy to forget all that though as we lay there and regaled each other with tales of some of our less successful sexual encounters. I was just finishing a story about trying to go down on a girl while I had a pube caught in my teeth and Georgie was rolling around in fits of giggles.

"Why didn't you stop?" She gasped out.

"You can't stop when you're down there. It's all very complicated for guys. It's like being dropped into the cockpit of a fighter jet and being told you have to land the thing on your first attempt without crashing."

"Cockpit," Georgie snorted.

"You're such a child," I swatted her bare calf muscle, "Anyway. If you have the thing flying smoothly you can't exactly take your foot off the gas."

"Wait, I thought the vagina was a fighter jet in this analogy. Do fighter jets have gas pedals?"

"I have no idea, and that's exactly my point. If the buttons, or levers, or pedals, or whatever you are pushing are working then you don't stop pushing them."

"Boys are dumb."

"We're not the ones who put the flight controls on the outside of the cockpit."

"Haha, cockpit!" Georgie started to giggle again, her plump breasts jiggling on her chest. I shook my head but could not help a wry smile. "I think that would be my ultimate fantasy," she sighed, calming down.

"Flying a jet?"

"No. Not flying a jet. Having someone 'fly my jet.' Or, more precisely, having someone down there who actually knew what they were doing."

"That's your greatest sexual fantasy?"

"Hell, yes. In fact, I'd settle for someone who could accept direction and not take it as some sort of fatal wound to their male pride."

"Shit, I'd love directions when I'm going down on a girl. A map, GPS coordinates, I'd even take a compass if it was offered."

Georgie grinned and asked, "So what's your ultimate sexual fantasy then?"

I shook my head, "You'll judge me."

"I won't."

"It's a cliche. You hate cliches."

"No!" Her eyes widened.

"Yup."

"Isn't it kind of... gross?"

"The heart wants what the heart wants."

"And you've never?"

I shook my head sadly.

"Not even with Sally Higgins? I heard she gave up the ass to half the football team."

"Serve me right for playing soccer," I sighed.

"What is it with guys and anal? I mean, an asshole can't feel as good as a pussy."

I shrugged, "I honestly can't say because I've never tried it. It's the mystery I think," I gazed wistfully towards the horizon before continuing, "And because it's something different. But mostly it's because it's the one thing we can almost never have. Just once I'd like to try it. Is that so bad?" I delivered the end of this speech like I was in front of a crowd, fighting for human rights.

"Okay, you've convinced me," she laughed, holding her sides, "Is it too late to change mine?"

"Are you serious?"

Her hands played with the string holding her bikini cups together. "As you said, I want to try it. You know me, I'll try anything once."

"Ha," I scoffed, "And how's that worked out for you in the past?"

Her dark eyes narrowed as she replied coldly, "My ankle tattoo of Pickle Rick is a conversation starter."

"It looks like a grinning turd."

"Exactly. Some of my most interesting conversations with strangers have started with those exact words."

It was my turn to laugh. Wiping at my eyes I said, "I wish they made more girls like you, George. Funny and willing to take it in the ass. You're the perfect woman."

"I cook too."

"Marry me," I said, jokingly.

"Let's try it," she replied with no hint of humor in her voice.

"Huh?" Her last sentence confused me so much with its unexpected bluntness it sobered me right out of my laughter.

"Anal. You want to try it. I want to try it. Let's try it."

There was a long pause as I contemplated precisely what she'd proposed. It was so unexpected, so out of left-field, that I began to laugh. I laughed so hard I was rolling around on the blanket. It was only partially forced.

"What?" Georgie demanded, a trifle peevishly.

"Holy shit. You had me there for a minute, Georgie. Can you imagine? You... and me...? Hells bells, woman. You got me good."

"I wasn't joking," her reply was level, her gaze firm. The laughter in my throat dried up for a second time. I wasn't sure it would ever come back.

"Come on, Georgina. It was funny once, but it's not cool to mess with a guy's head like that," I nervously dusted something imaginary from my body.

"I'm being serious. Why not? You want to try it and so do I. You'll never have the courage to suggest it to any girl you date and I will never let a guy try it on with me for two reasons. Firstly if things go wrong it could ruin a relationship."

"Couldn't it ruin our relationship?"

"Hardly. We've been through everything together, Johnny. We've seen each other's worst, most embarrassing moments. This is hardly going to scare one of us off." I silently concede the point. "I love you and you love me, right?"

I nodded at this and admitted, "Sometimes I think you're the only person I will ever love, George."

"So, that brings me to my second point: If things don't work or get too painful you're the one guy I can tell to stop without pricking your precious male pride."

"That's because I have no pride."

"Is it ironic that you said that with so much pride?"

"I don't have any shame either."

"Until today, apparently."

I shook my head, "Man, you've really thought this through." When I looked at her, her dark eyes, so nearly identical to mine, were downcast. She would not meet my gaze. Was this spur of the moment, or was there calculation behind it? Even I found it hard to tell with Georgie sometimes. Slightly worried, I asked, "Wait. We're not actually considering this, are we? It's incest."

"Does anal sex count as incest?"

"It's not not incest."

"And you're not not a total virgin and yet you always act like one."

"A compelling argument."

"Come on. I'm bored and you know I like to do crazy shit when I'm bored."

"I think Pickle Rick can attest to that."

"What's the harm? We try it and if we don't like it we stop. I know where you've been, I'm discounting Sally Higgins by the way. If you'd caught anything off her it surely would've presented by now."

"I've had all my shots."

"And you know where I've been."

"Tobey French," I made a gag face.

"Yeah, yeah. That was my goth phase. I got that out of my system. Move on. Let's see, what else is there?... I have a great ass... It's not like I can get pregnant this way, so no mutant babies... Did I mention that I have a great ass? Feel free to stop me if you have any counter arguments."

I didn't. I couldn't. My mouth was dry and I was staring at the swell of her ass, encased tightly in insubstantial denim. This was suddenly starting to feel very real. I swallowed hard and managed a throaty, "What if people find out?"

Georgie waved an arm around the empty yard and asked, "Who is going to find out?" We were bordered on all sides by a fence and a thick hedge. Dad had turned the place into a private compound and the only way in was through an electric gate. We knew how to effectively monitor that from the days when we used to sneak booze from the liquor cabinet. And mom and dad hardly ever came home during the day. Not without alerting us first. "Besides, everyone we went to school with already thinks we secretly bone each other."

"Bone' each other?"

"Not my words. That's what happens when your best friend is your twin brother. So, we might as well do the deed if the suspicion is already there."

"Sound logic. You should change your major to law."

"And it's not like you're not attracted to me."

"Hey, what do you mean?"

"Please. You think I don't see you peeking down my top sometimes? I know I just have to put a bikini on and you get a boner."

"I do not," I protested, "And can you stop misusing the word 'bone.' It sounds ridiculous when you say it."

"I'm wearing a bikini now. Should we test to see if you're packing bone?"

"No," I placed a defensive hand over my crotch. She was right, I'd been hard pretty much since we got out here and all this talk of putting my dick in her ass hadn't helped. "And that's not even a real euphemism."

She gave a careless shrug, "Relax, I think you're cute too. It's an objective fact. All my friends agree."

"Wait, your friends agree? Even Steph?"

"Focus, Johnny." She took a breath before continuing, "In the grand scheme of things we really wouldn't be doing anything wrong."

"Try telling that to mom and dad," I thought, but didn't voice it.

Georgie rolled onto her stomach and subtly lifted her hips. Giving her backside of callipygian perfection a subtle wiggle she said, "So, decide already. This is a once in a lifetime, bone your twin sister in the butt opportunity. Are you in?"

I took a deep breath, ignored her deliberate attempt to bait me, punched my fist into my palm, and practically whooped, "Hell yes! You've convinced me. I'm in. Well, Not yet. But I definitely want to be."

"Great!" She gave me another brilliant smile. "You stay here. I'll go get ready." She bounced up to her feet, "Back in a bit."

"Ready?"

"Yeah. Ready. Prepared. I've got stuff to do. I can fill you in on the details, but I think a little mystery is always good in these situations."

"Sure. Yeah. Me too. I feel the same every time I contemplate a round of incestuous butt sex." I waved her away, "Prepare away."

Georgie sashayed her beautiful big ass back into the house and I lay back on the blanket and closed my eyes. This had to be a dream. I was going to open my eyes in a minute and find that I'd fallen asleep in the shade and Georgie would be there and everything would be back to normal. It wasn't the first time I'd had dirty dreams about my sister. It was just a dream. A wonderful, wonderful dream.

Maybe I really had dozed off because the next thing I was aware of was Georgie's big toe poking me in the ribs. I didn't want to open my eyes though, it was such a great dream.

"Don't make me change my mind, Johnny-boy," Georgie said.

I did open my eyes then and took in the full length of her beauty as she stood over me. Strong, elegantly formed legs. Hips with a wicked flare which then cut back to a narrow waist and tits that hung ripe and full off her chest, straining against the mere strings tasked with securing her bikini top.

Her smile was timid but no less radiant for it. She waggled a small tube in the hand she held next to her face and announced, "I'm as ready as I'll ever be. Are you?" Glancing down, she poked her toe at the bulge in my shorts and said, "He certainly seems to be."

I jerked involuntarily at the contract. Georgie had just touched my hard cock. Sure, it was only with her toe, but a boundary had been crossed. "Um," I paused before nodding to the tube of lubricant in her hand, "Where'd you get that?"

She giggled before whispering, "It's Mom's."

"Ewww."

"She keeps it in the drawer of her bedside table."

"Ewww!"

"I've known about it for years."

"Please stop talking," I covered my ears.

"What, you think Mom and Dad don't do it?"

"Ewww. Seriously, stop. They don't, do they?"

"What, bone? Of course."

"Yuck! Stop saying that word. I thought they just did it once. You know, to have us."

"No way. They go at it like rabbits. Don't you hear them at night? It's probably why they need all the lube."

"Shut the fuck up."

"If you want to poke me in the ass you are not going in dry. It's this or nothing." She knelt down next to me and held out the tube.

I eyed it suspiciously. Coaxed by Georgie's expression I reluctantly took the bottle between my thumb and forefinger. I held it like it was a vial of poison.

"So," she put her hands on her thighs and bent forward. I found my eyes straying down to her ample cleavage. When I looked back up she was grinning knowingly. "How do we do this?"

"Um."

"Do we just get naked, or..."

"I don't know."

"Why don't we start by taking off our bottoms, at least? Then we can see what we're working with." She turned her body and presented her backside to me. The wide, curved expanse of her beautiful bottom stretched the fabric of her tiny shorts tight. Christ, I wanted it so bad.

"What are you waiting for?" She prompted. I was confused until I heard her snap open the button atop her denim cut-offs. She looked back at me over her shoulder, one eyebrow raised.

I scrambled to get to my knees behind her. This was happening. This was really happening. I placed a tentative hand on her hip. She did not flinch away but there was an involuntary muscle twitch when my skin touched hers. We'd never had a problem with physical contact before, but this felt very different.

Not certain how to proceed, I moved my hand down to the top of her shorts. Even with the button and fly open the shorts were still tight. I tried to casually slide them down, as if my hand had accidentally slipped. That did not work. They were unforgivingly wedged onto her thickness. There could be no qualms about it, if I was going to do this it would have to be with unflinching intent.

Georgie was watching me out of the corner of one eye. I didn't want to let her down. Taking a fortifying breath, I hooked my fingers under the hem of her shorts and dragged them down. They peeled away reluctantly, bringing with them the matching white bottoms of her bikini. Mocha skin gave way to untanned vanilla and then the two fat scoops of my sister's beautiful bottom were exposed. I could not stop now, not even if I wanted to. As the shorts rolled down onto her thighs the valley between her cheeks sprung open. I was now staring down at the perfect pink swirl of Georgie's pristine asshole.

"Fuck," I breathed out, "You have a really pretty butthole."

"Why, Thank you," she put a hand to her heart in mock coyness. "You know, so few people take the time to compliment me on that particular part of my anatomy."

"Well, they should. It's amazing."

"Such a gentleman. I can't imagine how you're still single."

"Yeah, yeah. Fuck you."

"That was kind of the plan. Hurry up, grandma."

"Okay. Okay," I waved away her chiding, "I've just never seen this side of you. It's.." I paused, ducking down and peeking into the secret glen tucked between her thighs. A deliciously plump pussy nestled there with thick, inviting lips pursed in a sensual kiss.

"Yeah?"

"Fuck, Georgie. It's amazing. You're amazing."

"Thank you," Her cheeks, olive-toned, flushed so subtly that only her twin brother would have noticed. "Do you see why I wanted to try this with you first? You always know the right thing to say."

I dragged her shorts and bikini bottoms to her knees. She lifted each in turn and together we got them over her feet. I tossed them to one side and sat back on my haunches to take in the full spectacle of her naked lower half.

"Well?" She interrupted and I realized I'd been staring with a fierce hunger at her parted ass cheeks for another long, silent moment. At my uncomprehending stare she rolled her eyes and said, "Aren't you going to join the no pants party? You're kind of leaving me with my ass hanging out here. Literally."

"Okay," I struggled with the knot on my board shorts. When I failed to get it untangled I grew impatient and wrenched them down. The progress was jerky and painful but I managed to get them over my hips and my cock leaped free, bouncing up like an eager puppy.