A Sister's Boots

I shoved the boot deep into my mouth, the toe hitting my throat. I started to fuck myself with the boot, but I had to contend myself with keeping it stuck in my throat when Ben continued thrusting his cock through my ass, going faster than ever and still slowly accelerating. My limp body shook wildly, and not only due to pleasure; with each thrust, he smacked his pelvis against my ass, and I thought that without his arms around me, he would have sent me flying forwards.

My pussy reacted heavily to the boot--my boot--in my mouth. Yeah, you like that, don't you? I thought. In fact, my pussy liked it so much...

The most ridiculous plan formed in my head.

I waved my arm behind me, hitting Ben's thigh. He understood the signal, though he kept his cock buried deep in my ass. I would've wanted it no other way. I took some time to recuperate from the vigorous fucking, but he showed no sign of slowing down. He moved down from my neck, twisting around me to kiss my breasts. He sucked on my nipple, taking with it as much of my breast as he could into his mouth, then letting it pop out again. I removed the boot from my mouth, moaning, "Uhhh, yes!"

I lowered the ankle boot to my pussy, running the heel against my lips. The blocked heel felt massive, but my pussy knew what it wanted.

I put my hand on Ben's head, and he looked up at me, my breast still in his mouth. "Don't you think it's time to change positions, sweetie?" I said. I didn't yet tell him what I was planning; he'd find out soon enough.

He pulled his cock of out my ass, waiting for me to take on a new position. My ass felt empty without his cock, stretched out but holding nothing. It was a weird sensation. I reclined on the bed, spreading my booted legs wide. I set the ankle boot just before my pussy, and reached down with my hand.

"This might take a moment," I told Ben. I slid two fingers into my pussy, quickly stroking my inner walls. It felt good, but two fingers were hardly anything, so I added a third. And a fourth.

My pussy was much more pliable than my ass, and soon I fit in my thumb. Ben watched with fascination, by this point aware of my plan. I grinned at him, and he shot one back at me. I was satisfied when I could comfortably stretch out all five fingers inside, widening my pussy. I vacated my wet hand from my pussy, closing it around my ankle boot.

I ran the heel over my pussy, as tenderly as I could, for I didn't think my pussy would feel tenderness again in quite some time. Though the cylindrical heel wasn't quite as long as my brother's cock, had twice the area. It would be a lot for my pussy to take.

Well, there's no sense in putting it off, I thought. I held the heel parallel to my pussy, holding the entrance open with my fingers, and then pressed, slowly and with great care not to hurt myself.

I held the tip of the heel between the lips of my pussy. "Aahhah," I panted. It was so big! I longed to have the rest of the heel inside of me, to have it fill me completely, to stretch out my pussy on all sides. To be fucked by my own boot.

I slid the heel further in, bit by bit. The heel's tip wasn't pointed or rounded like other objects made to drill; it was blunt, without avant-garde to ease up my pussy for what was to come. It made getting it into my pussy harder, but also so much more pleasurable. Though I pushed it in as slowly as I could, it still felt like the heel crashed through me, like it fucked me as hard as Ben had before.

I got the heel all the way into my pussy, my lips closing around the place the heel was attached to the boot's sole. I looked down at the boot, its toe pointed up at me. The thigh-boots around my legs rested beyond. Ben's cum on them had dried, they were so sexy and so hot. I wouldn't allow them to be forgotten.

My pussy closed tightly around the heel, grabbing onto it. It was huge, and it made me feel a little like I had to pee. I was familiar with the feeling, and I knew I didn't really have to; the heel had made me so horny, and I was close to orgasm.

Ben bent down between my spread legs, kissing the boot that stuck out of my pussy in an intimate gesture. "You know, I never thought I'd wear three boots at once," I joked to him.

He laughed. "So, is it going to be the new norm?"

"Of course it is."

I raised my booted legs up high into the air, the movement opening my asshole right in front of him. Though I wanted to fuck myself with my boot already, my pussy needed some time to adjust to the new arrangement. In the meantime, I wanted Ben back in my ass. He plucked my boots right out of the air, resting them on his shoulders as he took my hips and placed my ass in the perfect position. Then he thrust his cock into my ass again in one fluid motion.

With the massive heel in my pussy, I underestimated what his cock could do to my ass. "Ooohhhhhh, FUCKHHHhhh..." He picked up right where he left off, fucking me hard. With each thrust his pelvis hit the boot, and though it only moved the heel slightly, it felt like the heel was thrust through my pussy with the same brutality his cock handled my ass. The difference was that my ass had grown accustomed.

I'd always fantasized about being doubly penetrated, to take two cocks inside me at once. I thought it would feel twice as good as one cock. In reality, it was much better. One guy was missing, but the huge heel had replaced the cock that would fuck my pussy, and it was doing a much better job of filling my pussy than any cock could.

My brother was completely obsessed with that heel, his eyes glued to the boot that stuck out of my pussy. I watched him, my suede ankles wrapped around his neck. Yes, my ankle boot fucked my pussy, but my thigh boots were also so hot... This morning I'd gone to campus in my other pair, and they'd made me weak in the knees by simply wearing them. They wouldn't be forgotten.

But Ben needed a reminder. I took his face between my boots, pressing them together. "Kiss my boots, Ben, lick them," I said urgently, increasing the pressure on his face for emphasis. He cast down a final look, then did as I told him.

I could clearly feel his lips through the leather of my boot, and it was almost as if he ran his tongue over my leg instead. Logically, the heel in my pussy and my brother's cock fucking my ass should have been plenty to make me orgasm, considering that together they brought me near the amount of pleasure an orgasm did. But my body didn't work that way; I could endure that for a long time. I needed something to seal the deal.

That something turned out to be Ben worshipping my boots. Watching him, feeling his attention for my boots, which made me feel so sexy, my orgasm built up. I felt it in my pussy, my ass, throughout my entire body.

Ben had delayed his orgasm earlier. I had no such intentions, welcoming and even encouraging mine. I'd been so pent up for so long that I needed some relief.

My entire body tensed up like a bowstring before releasing an arrow. My pussy boiled my heel, my stomach boiled itself. I grabbed my breasts, pinching my nipples between my fingers. And all the while my brother fucked my ass and licked my boots.

"Oh fuck oh fuck, ooohhh, fuuuckhhh, yesss!" I moaned softly. He noticed how close I was, and drilled my ass even harder.

"oh yes Ben, oohh yess fuck me yes, kiss my boots, ohhh fuckhh, oh yes fuck my ass, oh fuck, oohhh yes fuck Ooohhooh fuckhhh OOOHHhhh FUCK O FUCK O FUCK O FFFFUUUUCCCCKKKKKHHHHH!!!"

I pressed my boots into Ben's face, roughly forcing a heel into his mouth and covering his eyes with my soles. Waves of ecstasy washed through my body, and I shook uncontrollably. Ben steadied me--his hands firmly holding down my hips--while, with his cock, he attempted to destroy the balance he created, pounding my ass harder than ever, making me shake as I dampened his every impact with my body.

My pussy clamped onto the heel, and I released a nipple from my fingers to grab the boot, needing to feel more of it than just the heel. I wanted to plunge the heel into my pussy, again and again, but I didn't think my pussy would even let go of the heel if I tried to pull it out.

I rode out my orgasm shouting for Ben to fuck me. When I came down, he started to slow down his fucking my ass.

"Don't stop!" I ordered him. One orgasm wasn't nearly enough, and my body was even tauter with sexual tension than before I came. Now more than ever I needed him to fuck me.

My pussy relaxed slightly around my boot's heel, and I felt I could finally fuck myself with it. I carefully pulled the heel out, Ben leaning back to give me some space. "AAAaahhhh..." There were no words to describe how good it felt to feel the heel move through my pussy. I took a deep breath when the heel's tip rested between my lips, my pussy so empty... The heel glistened with my juices, and I saw my little brother watching hungrily. The heel was meant for my pussy, but another boot lay next to me.

I pulled out the rest of the heel, giving the boot to Ben, who immediately started licking off my juices. Smiling, I replaced the boot with its friend, pressing the new heel between my lips. I gasped, as it was cold compared to the other heel which I'd warmed up. Luckily, it didn't absorb my pussy's warmth too quickly, so the cold was manageable.

I slid the heel into my pussy, its tip--the edges barely rounded, almost sharp--rough against the wall of my pussy, mercilessly granting itself access. I leaned back my head, taking a moment to enjoy the heel, Ben's cock, the boots I wore... "Oooh fuckhhh..." I moaned.

I got back to it quickly, however, now truly starting to fuck my pussy. I didn't thrust the heel through my pussy in its entirety, however, making movements of only half the heel's length. First I'd get my pussy accustomed to this, then I could work the whole heel.

Ben gave me back the first boot, the heel now glistening with his saliva. We swapped boots again. I figured it couldn't hurt, as I was wet enough to sustain it for a long time, and it was so hot to stick a heel with his saliva in my pussy. The only problem was that it deflected his attention from my thigh boots. They rested on his shoulders again, all but forgotten now that he had my ankle boots with my pussy's juices.

I watched those boots so fondly, my feet sticking into the air, swaying with our rhythm. I inspected the patterns of Ben's cum on them and wriggled my toes around. They were so sexy, so pretty. Their soft suede was wrapped tightly around my legs, stopping halfway up my thighs, as if reaching up to my pussy. In my boots, my feet rested slanted, supported by those long heels that stuck out under the soles, adjusting my posture to highlight my chest and ass. They elevated me to their level of sexiness, and it was one of the reasons I loved them so. Yes, even when a different heel and a cock penetrated my pussy and ass, I'd make sure they got the attention they deserved, though all I could do was watch.

And... "Ooohhh, fuckhh..." For the second time, they sent me into an orgasm, just by watching and wearing them. It was the perfect way to express my feelings for them.

Just like the first time they made me cum--when Ben had licked them--my thigh boots weren't the sole reason I came; the heel and his cock were what brought me close. My boots were simply what triggered it.

My brother bent over me, doubling me over as my legs still rested on his shoulders. He bent me into a compact package and picked me up after putting his hands on my back, his cock still deep in my ass.

"Oh fuck, ohhh, fuckkhhh..." I breathed as he carried me through my room. I couldn't see where to; I'd leaned back my head, my eyes closed as I felt my orgasm warm up throughout my entire body, just not hitting me.

Bang! My back slammed into a wall just as my orgasm coursed through me, "Aaahhh FUCKKHH!" I screamed. Ben immediately continued fucking my ass, this time not so careful not to touch the boot in my pussy. He smashed against it, shoving the heel through my pussy in phase with his cock through my ass. It was like the boot fucked me of its own accord.

He sandwiched me between himself and the wall, dampening the uncontrollable shaking of my orgasm. I was completely his, and... "Oohh, fuck, fuck, fuck." I'd gone from screaming to a mere whimper.

It was so much--too much. I felt so good, so good. It was my longest orgasm ever. Oh, I was getting light-headed. I held on to my brother and his cock in my ass, my sexy boots. I wouldn't faint. I refused to miss the best orgasm of my life.

I was almost glad when my orgasm ebbed away. I smiled proudly, relaxing and letting myself sink, trusting Ben to hold me in place. I hadn't fainted. But from the ashes of my second orgasm rose an intense, new feeling, bubbling up in my stomach, first spreading to my pussy, then the rest of my body. It was the same I'd felt after the first time I came, only magnified by what felt like tenfold.

My body wasn't close to done, my orgasms doing nothing to smother my arousal. Great desire for my brother, for boots burned inside me. I knew those boots would sate me in the end, however. I'd see to that.

Ben was already doing his part. He had learned from the last time and hadn't slowed down a bit after I came down, his cock and my heel still firmly pounding me. I heard him groan softly. He was close to cumming. That was good. The way I felt, it wouldn't be long before I came again, too.

I found myself suspended between Ben and the wall, my legs draped over his shoulders. The position placed my ass perfectly for him to penetrate. I hadn't noticed how he fucked me before, completely occupied with my orgasm.

His head rested beside mine, so I could easily speak into his ear. "Just a bit longer," I whispered, "I'll tell you when." I felt him nod just before he kissed my neck, passionately licking me all over.

We were both stretched to our limits. I could feel him getting tired, thrusting his cock into my ass with less speed than he had before. It also couldn't be easy to keep me up in this position. Best to go out with a bang than let it fizzle out.

I had to cum again as soon as possible, and I knew just what would help me get there.

Ben had me bent double, and my knees--my suede-clad knees--rested just before me. I attacked my own boots, taking long licks of the suede. It was too bad my heels and feet and soles were out of my tongue's reach, dangling far behind my brother's back; I'd have to do with what was given me.

It was good enough, though. I already worshipped the heel of my ankle boot with my pussy. I moaned as I licked and kissed my boots' shafts, covered in Ben's cum. It had dried, and no matter how much I licked at the stains, they wouldn't come out again. I grinned. Good.

I was ready to cum again within minutes. My body was so tensed up, ready to explode. That was not surprising, with Ben's tongue on my neck, his cock in my ass. I didn't even have to handle the boot in my pussy myself for it to fuck me, his fucking taking care of that. This allowed me to give my thigh boots every bit of the attention they deserved.

I could tell this would be my last orgasm. The third would be to one that finally washed away all that tension. I felt sore, in my pussy and in my ass, in my legs and in the muscles on my stomach, though the tempest raging inside me subdued that for now.

Ben and I were both breathing heavily. Deep in my stomach, I felt the first signs of my impending final orgasm. It would be greater than the two I had before combined.

"Oh, Ben... Oh, Ben... Ben..." I moaned. It was all I could say, unable to further warn him he could cum soon, too.

He understood me, of course. I didn't know why I even doubted that. Even if I'd said nothing, he could feel me beginning to shake, unimaginable pleasure rippling through my body.

He thrust his cock into my ass a few final times, as hard and deep as he could, eliciting an "AAAAHHHOOOOHHHHHHhhhhhh..." from me.

He pulled his cock out of my ass, setting me down. Suddenly I stood again, resting on my sexy heels. I gasped at the sudden emptiness of my ass, reaching down my back with my hand, filling myself up again with three fingers. No, not enough. I had to add a fourth.

I grabbed my ankle boot, my pussy still clamping onto the heel. Though I thought my pussy would never truly get used to the heel, it was close. The heel was huge and still felt as such, but I rammed it through my pussy as if it were a toy three times as small.

Ben sunk to his knees in front of me, holding his cock in his hand and jerking himself to completion, aiming at my thigh boots in front of him.

Usually, it wasn't too hard to maintain balance on blocked heels, even those as tall as mine, but as I shook harder and harder in the moments before I came, I had to lean back against the wall to remain standing.

His eyes locked with mine, moments before we came together. We didn't touch but were still so intimate.

There was a moment of silence, tranquility before the storm that would be our orgasms.

Our breaths were deep and long, but they started to come quicker, getting increasingly shallow, approaching the rhythm of the movements of Ben's hand around his cock and the heel through my pussy.

...And then we came.

I barely heard his low grunts over my screams, "OOOOOHHHHHH, YEEHHHHHESSSS... FFFFUUUUCCCCKKKKKHHHHHHHHHHHhhhhhhhh......!!!" All that tension in my body... finally it exploded, ripped out of me so that my every nerve was only touched by pleasure.

I kept leaning back against the wall, acquiring much-needed support for my shaking body. My sight was hazy but good enough to see Ben shoot his cum all over my boots. He shot it hard so that I felt it land on my feet, my shins and calves, my knees and thighs. He gave my boots their second load and made sure to miss nothing.

My pussy pulsated around my heel, contracting and grabbing the heel tightly, then relaxing slightly before going again. I faintly felt my ass do the same around my fingers.

My pulsating orgasm didn't stop me from fucking myself with my ankle boot. It only made the heel feel so much better, as I rammed it through an even tighter pussy.

oh fuck o fuck o fuck o fuck... I voiced my thoughts, "o fuck oh fuckhh OOHHhh fuckkhh FFUUCKKHHHhhh!!!" Oh, fuck, the feeling couldn't be compared to any other. The first and second time I came I'd thought that had been my best orgasm yet. My body had just been preparing; they hadn't even come close to the ecstasy I felt now.

Ben had risen from his knees, now spraying his cum over my ankle boot. I looked down. My thigh boots were completely covered in white, his cum dripping down all around the suede shafts. I agreed with him. They were done; he should cum on my ankle boot now.

He squirted and sprayed it over the smooth leather, some strings of his cum disappearing inside the boot. I still held it, pumping the heel deep into my pussy, and he shot some on my hand, too. Men and their terrible aim, I thought with an inward laugh.

His orgasm had lasted long, and there was so much cum! But mine lasted longer. I could tell he was close to done when the stream of cum from his cock slowed. He buried his cock inside my ankle boot, so it acted as an intermediary between him and my pussy, giving the boot's interior the last bit of his cum as his orgasm died out. Oh, how I would enjoy walking around in that.

He wrapped my orgasming body into a hug, kissing me and stifling my moans. "Hmm, Hmm, Hhhmmmmhh." I found I could still moan through my throat, however, and I settled for that. With his body against mine, Ben pressed the heel as deep into my pussy as it would go, firmly keeping it there. AAahhhh, that felt so good, to have my pussy contract around the entire heel.

I hugged my brother back, riding out the last moments of my orgasm in his loving arms. It died out quietly, and we stood there for a moment, motionless, our breathing the only sound.