Anytime, Anywhere
by Pan
“Now,” my brother said with a grin.
My eyes grew wide as I realized what he was referring to. God, it had completely slipped my mind.
Why had I ever made that dumb bet?
As I got to my knees with a sigh, I seriously asked myself that question. Why had I made that bet? I couldn’t even remember what it had been for, but I must have been very confident in it, considering the stakes.
If I’d won, I would’ve gotten my brother’s car. But since I lost…
“Here?” I grumbled. “Now?”
But I already knew the answer to my questions.
“Anytime,” he reminded me. “Anywhere.”
I’ve always loved making dumb bets. That I can spot five white cars before you see a blue one, or which bird flying overhead will land first. I sometimes think I must have a fairy blessing or something, because…I dunno, I feel like I win most of the time.
Or maybe I just subconsciously pick bets I know I’m going to win. Whatever the reason, I’ve got a hot streak going on ten years.
The wager is normally pretty low. Five bucks, or loser does the dishes. Sometimes when we’re having a night out, we’ll do a bet for who has to be designated driver, stuff like that.
And just like I have a fairy blessing, I sometimes wonder if my brother has a curse. The number of forfeits he’s lost over the years…it must have been hundreds, if not thousands.
But not this bet. He’d won this one fair and square.
I just wished I could remember what it had been.
My mouth opened to engulf my brother’s cock, and I began running my tongue up and down his smooth shaft. He was already hard—he often was, when he reminded me of the bet. I don’t know if he only ever did it when he was turned on, or if he got turned on knowing he was about to claim his prize, but I guess it didn’t really matter. The end result was the same.
I don’t think I’ve ever seen my brother’s cock flaccid. When I’m done, he really quickly puts it away, so I guess it softens in his pants.
I rolled my eyes at my dumb thought process. What I had to do was bad enough, I didn’t have to expend mental energy thinking about it.
Trying to focus on the task in front of me, I opened my mouth and took my brother’s erection into my mouth. It was only a few seconds before I’d swallowed his entire shaft.
A feeling of pride filled me. I was getting pretty good at this.
I think my brother agreed, because it wasn’t long before he was cumming. I could feel his hot seed splashing the back of my throat, and I swallowed it down.
As soon as he was done, he quickly pulled out and tucked his cock away, before throwing me a sly glance.
I narrowed my eyes. What was he looking at me like that for? God, my brother could be so weird sometimes.
Shooting him a look, I glanced away. There was a weird, scratchy feeling at the back of my throat. I hoped I wasn’t coming down with something.
“Yo,” my brother said, making his way into my bedroom. I raised my eyebrows.
“What do you want?” I asked, and he grinned, like he knew a secret I didn’t.
“You know what I’m here for,” he said, and I froze.
Ah, shit. I’d totally forgotten. How did this keep slipping my mind?
“C’mon,” I said with a sigh. “I don’t even know how you…”
My mouth dangled open uselessly. I’d been about to question the fairness of the bet he’d won, but…it was the weirdest thing, I just couldn’t remember what it was.
What the hell had the bet been?
“…won,” I finished lamely. “You probably cheated.”
“It was your bet,” my brother said, a smug look on his face. “I just went along with it.”
“Yeah, yeah,” I grumbled, getting to my knees. He was probably right.
I just wished I could remember the specifics of what we’d bet on. Maybe then I could challenge him to double or nothing, or something like that. Though I didn’t know what double would look like, in this case. It was hard to get anywherer than what we were already doing.
“C’mon,” I said, pawing at his jeans. “Let’s get this over with.”
“Nah,” he said, using his head to point at my bed. “I think I want to fuck you this time.”
My eyes opened, and I held up one hand.
“Whoa whoa whoa,” I said defensively. “That was not the deal.”
“Anytime,” he said cockily. “Anywhere. The time is now, and the where…”
His eyes flashed down to the skirt I was wearing, and my face went red.
No. This hadn’t been what we’d agreed to.
Had it?
I’d thought I’d just agreed to give my brother head, but…no, that didn’t make any sense.
Why would I agree to give head to my brother?
If I’d won, I got his car. But even then, even in that situation, oral sex didn’t make any sense. No matter how confident I’d been in the wager, I just couldn’t imagine myself making that bet.
But of course, I didn’t need to imagine. I just needed to remember.
And for whatever reason, I couldn’t.
Agreeing to give my brother head…that was nonsense. That was something I would never, ever do.
So, yeah. I must have agreed to all types of sex.
Shit.
“Fine,” I groaned, getting on the bed and flipping up my skirt. “But let’s be quick about it.”
“I’ll do my best,” my brother responded, unzipping his pants and removing his cock. He never undressed when claiming his reward, which I appreciated. It would have been super weird to see my own brother naked. Definitely not something I needed in my life.
I reached down and pulled my panties to the side. Just as he was already hard, I was soaked. I guess my body had remembered the terms of the bet better than my head.
Anytime, anywhere.
My hips involuntarily bucked with pleasure as I felt my brother’s smooth cock sliding inside me. I couldn’t remember how many times I’d had it inside my mouth—no, seriously. I literally couldn’t remember.
But I knew it had been a lot.
I was confident, however, that this was the first time I’d felt him between my legs.
As much as I hated to admit it, it felt good. I hadn’t been fucked in months, and I’d missed it. My brother may have been a moron, but he had a great cock. I gasped as he finished moving forward, his cock filling me up, his body pressing down above me.
Normally when I got my brother off, my mouth was full. He’d had me jerk him off once or twice, but then I’d swallowed his seed. Mostly just to avoid the mess.
This time, however, I wasn’t on my knees, or bent over his lap. I was on my back, his eyes staring lustfully into mine…and, embarrasingly enough, I was probably staring lustfully back.
Neither of us said a work as he proceeded to fuck me, but my non-full mouth started letting out little groans and pants of arousal. It wasn’t that I was into what was happening, to be clear. It just…felt good.
Annoyingly good.
It must have felt good for him too, because just as I could feel my crest starting to really build, he groaned, and his long, slow thrusts grew fast and sporadic.
Even if I hadn’t gotten way too familiar with my brother’s o-face, I know what it feels like to have someone cum inside you. I knew I was just a minute or two from my own orgasm, but as I was debating whether it was worth the humiliation of asking my brother to keep his cock inside me so I could cum, he’d quickly pulled out and moved my panties back into place.
“Thanks, sis,” he said with a leer. His cock was covered in a mixture of our juices, but he didn’t ask me to clean it up—he just returned it to his pants, and left me alone in the room.
I stared at the door, my brow furrowed.
For some reason, I was feeling hornier than I could remember feeling in a long while. My panties felt completely soaked, and I wanted nothing more than to lay down on my bed and get off.
I had no idea why I’d left my door open, but I quickly closed it. Didn’t want my brother to walk past and see me getting off, after all. What would he think?
“Your ass,” my brother said confidently, reaching down to grasp it.
I wanted to slap his hand away, call him a pervert, but…well, as soon as he touched me, I remembered.
Damn it, how did I keep forgetting?
Anytime, anywhere.
Including, I suppose, my ass.
I glanced into the kitchen, where our mother was preparing a meal. She probably wouldn’t come back into the living-room until she was done, and salmon took forever to cook.
Not that that really mattered. Anytime obviously included “while our mother was one room over”, and anywhere covered the living-room.
And my ass.
“Fine,” I sighed, unbuckling my jeans and pulling them down. My panties were next, and my brother smiled at the sight of my bare ass winking at him.
I’d never taken anyone in my rear before, but I couldn’t deny that the idea excited me a little.
I just wish it hadn’t been my brother.
Still, the terms of the bet had been clear. Presumably. I didn’t remember them exactly, but there was no way I would’ve let my brother fuck me so often if it hadn’t been for a good reason.
Anytime, anywhere.
I’d thought he was a horny bastard when it was just head, but once my brother had expanded the terms of the bet to my pussy, he was insatiable. Barely a day went by without him bending me over and using my wetness to get off, fucking me in every room of the house (anywhere) at all hours of the day and night (anytime).
I’d lost count of the number of times he’d finished inside me. No, seriously. I have no idea how many times it’d been. It could have been a thousand.
How long ago had we made that bet? Months ago?
Years?
I never came, I remembered that. He’d fuck me until he unloaded inside me, leaving me dripping—not only with his cum, but with my own juices as well.
I remembered that, but not how many times my own brother had fucked me. What was going on with my memory?
His hands roaming across my bare ass told me that this wasn’t the time to be thinking about that. Instead, my focus should be on my brother taking my ass for the first time.
“Are you ready?” I asked, and he looked at me like I was an idiot. I hadn’t noticed him lowering his pants—I’d been too lost in my own thoughts—but his hard cock was now exposed, staring at me as it had so many times before.
“I don’t have any lube,” he said, and I blushed. I probably should have had some on me. The rules were very clear: anytime, anywhere.
That meant I needed to be prepared, at all times, to take my brother inside me. Anywhere.
“I can use my mouth?” I offered, and he nodded, satisfied with my solution. I could have offered my pussy, I guess: I was soaking wet, as I always was when my brother went to claim his winnings.
I just wished I could remember what the damn bet had been for.
A smile crossed my face as I dropped to my knees in front of my brother, as I’d done so many times before. Not for a while, since he’d started fucking me, but before that...
As my brother’s cock slipped into my mouth, I focused my attention on it. I knew what to do; I’d done it hundreds of times. Thousands?
And I was damn good at it.
My tongue traced around the head, licking it clean. My lips caressed the shaft, teasing out a drop of pre-cum. Then I took my brother deep, my throat constricting around him.
It was a strange feeling, having my brother’s cock buried down my throat. Equal parts weird and wonderful. I’d missed it, I realized. I’d missed the taste of my brother’s cum.
But that’s not what we were doing today.
For the next few minutes, I used my mouth to prepare my brother’s erection. To lubricate it, for where it was going next. For where no man had ever gone before.
And when his cock was dripping with my saliva, I bent over the couch.
I could hear my mother humming in the next room over, a tuneless song she always sang when cooking. I closed my eyes as the head of my brother’s cock pressed against my virgin asshole, bracing myself. I’d done all I could to allow for a smooth entry, but as he slowly began pushing forward, it still hurt.
Not an agonizing pain, though. Just…a new kind of discomfort. I took a breath, bit my lip, then I pushed back against him and let him in. I stifled my groan, knowing I couldn’t make a noise, not with Mom so close.
The sensation of my brother taking my ass was a little different than I’d imagined: it hurt more, for sure, but it was also...better. More intense, in both directions at once. My entire body began to tingle, just as it did when he fucked me, when he brought me to the edge of orgasm but never let me tip over.
I wanted to move, but my brother was holding me tight. He just kept thrusting, harder, faster, deeper. It was a lot of effort for me to hold back my moans of pain and pleasure, and he laughed. I guess laughter was okay; Mom wouldn’t need to come and investigate that.
“This feels great, sis,” he said, and I silently nodded. I hadn’t even noticed the tears beginning to stream down my face, but they were. I was unwittingly crying at the intensity of feeling my brother’s cock inside my ass for the first time.
And I knew it wouldn’t be the last. Anytime, anywhere.
He thrust forward again, and as I felt his pubic hair against my bare ass, I knew he was in. My brother was inside me; my ass was full. I’d never had anything in it before, and now my brother’s huge cock was all the way inside me, filling me up.
I wanted to groan at the thought. It had been a dumb bet (probably?) but damn. Losing sure had its perks.
Just as slowly as he’d entered me, he pulled out, then thrust forward again.
I felt it, that familiar, incredible pressure. “Oh, god, you’re so fucking big,” I gasped, as quietly as I could.
“You like it?” he asked, and I nodded, my face stretched with agony and joy.
At my response, he started pounding into me, taking my ass without mercy. Not that I wanted it, not really. The feeling of my brother’s cock stretching me, of his balls slapping against my thighs, of him fucking me so hard that I couldn’t breathe...it was too much.
I felt him grab my hips, pulling me into him as he started fucking me with reckless abandon. The sound of our flesh hitting each other was so loud, I was worried Mom would hear, come and see what her two children were doing…but she didn’t.
I wasn’t quite sure how much longer I could take this, but my brother didn’t seem to care. He was enjoying it as much as I was...and I have to admit, I was enjoying it. I’d always liked it when my brother fucked me—sure, I only did it because of whatever the bet had been, but that didn’t mean I didn’t enjoy it.
My brother was slamming into me, taking my ass, using me for his pleasure, and I was loving it.
“I’m going to cum,” he grunted, my body shuddered as my brother filled my asshole with cum. I cried out, not from the pain of my brother’s cock, but the intense pleasure of it.
I was surprised at how good it felt. How good it felt for my brother to cum inside my ass. I had been so close to cumming, but it was just out of reach.
As I continued to tremble, my brother’s cock still buried in my asshole, my brother’s seed still coating my insides, I breathed heavily. I could feel it, that thick, heavy load of semen, slowly leaking out of my ass.
It was a strange sensation, not unpleasant. It was one that I knew I’d get used to.
“Wow,” I said, once I’d recovered enough to speak.
“Yeah, I know, right?” he replied, his voice strained.
I was still shaking as my brother pulled out of me, my body still trembling, my pussy dripping. I pulled up my panties, pulled up my jeans, and collapsed onto the couch. I was a little sore, but that was to be expected.
My brother smiled as he moved towards the bathroom. “I need a shower.”
If he’d asked me to join him, I would have. Anytime, anywhere. That had been the bet.
But he didn’t. Instead, as I sat on the couch, I blinked twice, confused.
I felt like I’d just done a full-body workout. My muscles were stiff, and I felt like I needed to wash myself off, but I also felt like I could sleep for days.
Weirdest of all, my ass was sore.
I could hear my mother humming in the kitchen, and the shower turning on upstairs. I was all alone.
All alone, and inexplicably horny. It would be a little risky, a little naughty, getting off in the living-room where anyone could catch me, but I didn’t care. If anything, the risk of the situation turned me on.
With a wicked smile, I decided to do it. I was going to get off.
As I unbuttoned my jeans and moved one hand between my legs, a strange phrase appeared in my head. It kept repeating until my orgasm hit just a few minutes later.
Anytime, anywhere. Anytime…anywhere…