Reunion with My Childhood Crush

Jade began to increase her speed. I enjoyed every second of it. The speed picked up, so much so that she had to start ramming her boot to the back of my head to go any faster. Slowly, my mouth opened up even further, to the point that her toe touched my throat.

I gagged. With her boot so far up my mouth, there was nothing else I could do, but it felt so good to gag on her boot, that I used the extra space to push her boot further in. I breathed furiously through my nose so that I could keep going.

At that point, Jade noticed I was gagging. To my disappointment, she stopped "Oh, are you OK?"

If I could have, I would have shouted at her to go on, but speaking is kind of hard when you have a boot up your throat. Instead, I gestured as urgently as I could for her to continue. She went back at it, fiercer than ever before.

At such a heated point, there's usually a climax, but we kept going for quite a while until I decided to give my aching mouth and jaws a little rest. I gestured for Jade to stop, and I let myself sag onto her boot for a moment. She smiled at me, and though it was a little hard to respond with my mouth, I believe my eyes spoke volumes.

Every moment of untangling my mouth from her boot pained me. It hurt my mouth and lips, as they had been stretched out further than they were meant to, and it hurt my soul, as I did not really want to take her boot out of my mouth.

I had ravaged her boot as much as it had my mouth. Large blobs of saliva clung all over it. It must have been as wet inside as outside. With my tongue, I smeared the saliva over the leather that I hadn't been able to fit into my mouth. It was only fair the rest of her boot got a taste, too.

"Why did you want to stop?" Jade asked. "Was it not fun?"

"It was extremely fun, but we had reached a point where we could go no further." I wiped my chin off on the blankets. "It was time we tried something else."

"Like what?" she asked excitedly.

"Shall we see if I can get one of these heels further into my mouth than the boot itself?"

Her face lit up at the idea. Then she started to look doubtful. "I'm not sure they are long enough to even stand a chance."

I grabbed one of her boots and placed the heel against my cheek for comparison. "OK, they do stand a chance," she admitted.

I rid myself of the rest of my clothes while I thought of the position that would be easiest for getting the heel into my mouth. I smiled when I thought of a fun position. I laid on my back on the carpet, and opened my mouth, anticipating.

Jade laughed as she understood what I wanted. "All right," she said. She started at my feet, spread her legs wide as she walked with one boot on either side of me over to my face. One boot slushed with every step she took. It was definitely wet on the inside. She stopped as she reached my throbbing cock, but I shook my head. Not yet. When she had placed both boots firmly on either side of my face, she looked down at me, and I looked up at her, past those long legs, past her wet crotch, past her beautiful breasts. "Aaaaahh," I said as if opening my mouth for the dentist.

Jade lifted the boot I hadn't just mouth fucked, and lowered the heel into my mouth. Before it was even halfway in, her sole hit my nose. I snickered. She made a ninety-degree adjustment, and it entered all the way. Her heels were large, but they still fit into my mouth, if only barely. It did go in farther than the toe of her boot.

Then she started fucking me, moving her heel up and down, from all the way up to my throat to right between my lips. Again, slowly at first, but gradually picking up pace. I grabbed the boot fucking my face and helped Jade thrust the heel down my throat. It came down hard, and it hurt each time, yet I loved it. Eventually, she went so fast, my hands could not keep up, so I went to stroking the other boot next to my face.

It was clearly not easy for Jade to keep her balance, standing on one heeled boot while stamping down on my throat with the other, and she spread her arms wide like some rope dancer. She stopped shortly after she couldn't go any faster. "Let's see how much you can take," she said softly.

She shifted her weight to the boot on my face. I was lucky she was lithe of build and did not weigh too much, or I think she would have gone straight through my throat. As a natural reaction, tears welled in my eyes, and I faintly gurgled and gagged under her heel. I clasped the boot on my face tightly.

Jade released the pressure from my throat, still keeping the heel lodged in there, and then she shifted her weight all over again. She fucked me that way, no longer shoving the heel down my throat, but dancing with her weight from foot to foot.

She continued like that for a while, increasing to speeds it seemed only she could. My cock was starting to hurt even worse than my throat, but as it stuck in the air, untouched and unstimulated, I couldn't come, no matter how much I wanted and needed to.

That was the reason I eventually stopped her, waving with my hands. She raised the heel from my throat, my saliva dripping down on my face. I did not move while Jade crouched down beside me, her beautiful face hovering over mine, her eyes gleaming. She was panting slightly, though I did not know whether from exertion or arousal. Looking at her wet crotch, I decided it must be a combination of both. I wiped the tears from my eyes while trying to remember how to close my mouth, moving my sore lips to each other, instead of away from each other. " 'Turns out, the heels can go in deeper," she said. "It's good to know."

I croaked in an attempt to speak.

"Are you OK? Did I go too far? You should have stopped me earlier."

This time I regained my voice, though it was still a little shaky. "No, no, no, don't worry, I'm fine." I smiled, "it was fun."

She smiled back at me. "It was, wasn't it?"

"Yeah, and I loved your improvisation at the end. Very creative. Just when I thought you could go no further, no deeper..."

She beamed at me, proud. "Thanks."

I scrambled to my knees in front of her, our faces now at an equal level. Her eyes shot down at my cock. "So, tell me," I asked, "why exactly are you enjoying yourself so much?"

"Is it not sufficient to know that I am?"

"I answered you when you asked. I ask this now because it makes no sense to me that a girl like you would indulge me in my fantasies. You don't have to tell me if you don't want to, but openness is healthy. Any bit of an answer you are willing to give will suffice."

She smiled and took a hold of my hand. "I am not indulging you in your fantasies. I mean, I am, but I am also doing it for my own enjoyment."

She took a deep breath. "You know that feeling when you're doing something...not allowed. Not that what we're doing is not allowed, but...there's a thrill to the unconventionality of it. It's exciting to me; it turns me on..."

I grinned at her crotch. "I can see that."

"...Also," she continued, exhibiting only the slightest signs of satisfaction at my comment, "a small part of it is the boots themselves. I feel sexy wearing them, as they are distinctly a female item of clothing, whereas other types of shoes are not. I am more in touch with my femininity in them, and that makes your love for them more satisfying. For that reason, I don't think I would have indulged -- as you say -- you in your fetish if you had had a fetish for something else. And then there's just your reactions to my boots. It's quite fun to see what they do for you. I get off on that, too."

I was astonished. "Wow, you really know yourself. Compared to your nuance, my sexuality feels somewhat...crude."

She laughed delightfully. "I am a woman. And besides, I had some time to think about why I wanted to do this so much during our walk from the train station. But, there is also another, much simpler reason."

"What?"

"I really like you, James."

"Ahw, I really like you, too," I told her, pulling her into a kiss.

"So, what do we do now?" Jade asked playfully, almost innocently. Oh, she was so sexy.

"How would you like to sit on my face?"

I felt exalted at the way her face lit up. "Oohh," she said excitedly.

Though it was not boot-related, it was another hot fantasy of mine to have a girl like Jade sit on my face. Even though she said she had been satisfied up to now, I wanted to do more for her, and I also figured I was not going anywhere anytime soon, so there would be more than enough time for her boots later.

"Let's get some clothes off of you, too," I said, as I had been completely naked for quite some time, while Jade still wore most of her clothes.

Picking up on what I mean by 'some,' Jade said, "don't worry. I'll keep my boots on."

Trying to be smooth, I lifted her tank top over her head, but taking off someone else's clothing is harder than your own, and everything quickly tangled. Luckily, with extra care, I also managed to untangle quickly, but my face was hot and, I imagine, very red when her face reappeared, her hair in disarray.

I was relieved to see amusement on her face, however. "I'll take care of the rest, sweetie," she said, placing a hand on my chest. "Lay down, I'll be on you in a minute."

What I really wanted was to make up for my embarrassment, but she'd called me 'sweetie,' so in my joy at hearing her call me that, I let it go. I returned to the position I just came from, flat on my back on the floor, and tilted my head to watch her unhook her bra, her small yet beautifully round and firm breasts bouncing free.

She stood up, unzipping her jeans and pulling them and her panties down to her knees, giving me a first look at her shaven pussy. She was one of those girls who got extra wet during arousal, and that made me all the more eager to have her sit on my face.

She did not descend on me immediately, looking at me for a few moments in thought, then awkwardly wiggling over to her closet, as the pants around her knees impeded her movement.

Curious to see what she was up to, my eyes followed her. She pulled two pairs of boots from a drawer, a plain, brown pair of ankle boots, and pair of black, buckled ankle boots. Biker boots they were called. They had a zipper in the front under the buckles. I loved those. They were worn boots, yet they still looked amazing.

She held both pairs up for me to see. "Just an extra little treat. D'you like these, or these?"

"The biker boots," I told her. I had an inkling as to what she would do with them. She dropped the brown boots and wiggled over to me, lowering her pussy to my face so that she could play with my cock. She pressed the boots in her hands down on my chest to maintain her balance, and she had to move around before finding my mouth with her pussy, already covering my whole face with her juices.

Her sex tasted even better than it smelt. I had planned on working my way to her pussy from her thighs, but she gave me no chance. At a steady pace, I let my tongue run circles over her lips, enjoying the slightly sweet taste of her pussy. Above me, she gasped and breathed hard. I moaned, too, letting her know how much I enjoyed her pussy.

Jade took my cock in her hand, spreading out my precum to use as a lubricant. It was not sufficient for a slick layer, and I was glad to hear her spit onto her palm and mix it with my precum so that whatever she decided to do with the boots, it would go smoothly.

She started moving slightly, rubbing her pussy over my circling tongue. I tried to be as consistent as I could so that she would know where my tongue would end up next. Not that it really mattered. The result was a messy, odd counterpoint, as her movements had no rhythm or thought to them. She had somewhat lost control of her body with pleasure.

For that reason, she had some trouble when she tried fitting the boot around my cock. I now understood why she'd smiled at my clumsiness trying to unclothe her. It was endearing, and it made me want her even more. Also, her hand and boot touching my tip felt good with each failed attempt to fill the boot with my cock.

I'd had my eyes closed since she sat down, as to not get any of her juice in my eyes when she searched out my mouth. But occasionally her ass cheeks slapped against my face when she made a particularly wild move, and I had to take a look.

When she finally got her aim right, she managed to slam the boot all the way down my cock, for she had lubed me that well, my tip hitting the inside sole. "Do you like the boot?" she said, almost shouted with excitement. My tongue otherwise occupied, I let her know I did with a low, and I hope sexy grunt.

At that same moment, my eyes sprang open, giving me an amazing view of her hind. It was there, under Jade, that I began to comprehend the beauty in contrast. Certainly not why contrast made for such beauty, but I could appreciate it. My face was so close that her ass cheeks, bouncing happily, seemed huge. And there, between them, was her tiny, pink asshole. It made for an amazing sight. I moaned involuntarily.

Jade was a lot more vocal than me, gasping for air, and then releasing it loudly in whatever way struck her horny state pleasurable. Unlike with the boots she fucked my mouth with, she did not build up speed. She pounded the boot down hard on my cock, gripping it tightly, my tip, out of which I was squirting a lot of precum, hitting the sole. The buckles jingled merrily. I had been ready to cum since before I finished cleaning her boots, and everything, the boot around my cock, Jade's moans, her pussy I was licking, and the sight of her cute asshole almost pushed me over the edge. Still, I decided I wanted to hold on to my orgasm until after Jade had come.

But I knew it could take a while for a woman to climax, so I tried my best to ignore the boot around my cock, and start focusing on Jade. I had to accelerate her orgasm, and delay mine.

I had a few ideas. I reached up with my left hand, blindly grabbing for one of Jade's breasts. She took my hand, guiding it onto her breast so that her stiff nipple stuck out between my fingers.

"Pinch!" she ordered me. I obliged, pressing my fingers together on her nipple, but she wasn't satisfied. "Harder!" I squeezed her entire breast, too, giving me an extra grip for my fingers. "Aahhh, yes! That's it!" she moaned.

I had another hand free. Momentarily stopping my tongue, I ran two fingers through her pussy, gathering up some of her juice, which she had in excess anyways. I pulled my arm around and smeared it over her asshole.

"OOH, YES," was the reaction I got. "Put in a finger, James."

I rubbed some more, then eased in my index finger. For all my care to do it gradually, one of Jade's shakes impaled her ass on my finger anyways. It was tight and hot in there, and though the presence of my finger kind of broke the earlier spell of her ass, it was replaced with a whole new sensation.

"Ah, yes, keep it there," she panted.

I moved my tongue to caress her clit. She pressed my tongue down into my mouth, allowing me to suck on her clit. After the kiss, she pulled back, my tongue following her. We repeated the move over and over again in a simple dance.

I could tell she was very close, and to aid her, I shoved my finger up and down her ass. It was the right move.

"Another one!" she ordered.

Not sure how to fit in another finger, I pulled out, pressing it together with my other finger, and slowly forcing my way back into her slightly stretched-out hole.

It was not stretched out quite far enough, as she gasped loudly as I made extra room. I now stroked her with two, and that did it.

"oh. Oh. Ooh, Ooh. OOOoh. Ah, FUCK! JAMES!" she screamed as she came.

She buckled over, releasing her hold of the boot around my cock, leaning with both hands on my thighs for support as her entire body spasmed. I pinched extra hard in her nipple, knowing she'd enjoy it. I especially enjoyed her orgasm in her ass, feeling her muscles spasm, slowing my fingers down a little to match the rocking of her body.

I had her clit between my lips when she came, and, a little unsure what to do in my inexperience, I let it go, seeking it out with my tongue instead. She took charge herself, grinding herself against me, more sensuously than she had been all night.

She orgasmed over three times longer than I estimated my record to be, all the while writhing, whimpering, and gasping, "Oh, James," until she eventually came down.

Her gasps turned into shaky laughter as she pulled her ass from my fingers, discarded the boot from my cock, turned around, and laid with her belly on mine, her breasts pressed to my chest. Tiny beads of sweat gleamed on her forehead.

"That was fun," she purred, cupping my face with both hands and forcing her mouth to mine. At first, she needed to recover, but soon she slowly started grinding her pelvis against my cock. "Tell me how you want to cum." She tenderly ran her hand over my jaw. "In my mouth? My pussy? Ass?" A soft kiss. "I will make it happen," she breathed. "Anything for my sweet James."

Again I found beauty in the contrast in this girl. She had been so rough with her boots, and now she was grinding at me with such gentle care. She had been so loud and wild, and now she spoke to me in barely a whisper.

I'd already made up my mind about how I wanted to cum, but I wanted to enjoy this soft, post-orgasm version of Jade a little longer. I kissed her, throwing one arm over her back to push her breasts further into me, and one hand on her ass to put more force of her pelvis on my cock.

"I want to cum in a pussy of your boots," I whispered. I wanted to do everything she'd just suggested, but just not quite as much as that.

Jade chuckled. "Of course." She rolled off me and got to her feet, zipping up her jeans again. Her stomach glistened with a layer of my precum and her saliva from my cock.

"We'll need to lube you again, I think," she said.

"What you did before worked nicely. I'll also lick your boots again, that should be sufficient."

Jade added her spit to my precum and the remainder of the previous layer, then sat on the bed as I, on my knees, licked her boots until they were completely wet again.

Once done, I straightened my back, her boots in my hand, ready to place them around my cock. I was already panting heavily without her touching me. I looked at her and smiled.

"Yes, fuck my boots, James." Jade moaned. "My boots are yours. Fuck them. I want your cum on them."

I leaned in and slid my cock between her boots. Jade and I both pressed them together on my cock, I with my hands, she with her legs. I gasped.

I slowly started fucking her, in, and out, in, and out of that delicious pussy of boots. I was well lubed, and her boots gave me no resistance. More precum oozed out of me, creating a silky canal for me to fuck her boots.

"Oh, Jade, I love your boots so much," I moaned in the heat.

"Fuck them, then," she moaned. "Fuck my boots, and cum on them," she repeated.

I made use of every bit of her boots. I pulled out until her boots held my tip between the sides of her soles, and then rammed myself back in until I could go no further, her toes pressed into my stomach and her heels grazing my thighs.

I changed it up after a while, fucking only her blocked heels. She clamped the heels around my cock, then moved them up and down my shaft. Before returning to the position I started in, I fucked her in the space between her heels and her inclined soles.

I was ready to cum, but still held back. She wanted my cum over her boots, and the longer I held out, the more of my cum I could give her.

But she and I picked up the pace, and my balls were starting to boil. I groaned, "Jade, I'm cumming soon."

"Stop!" she said suddenly, pulling her boots away from my cock.

"What..." I started, angry, annoyed, and confused all at once.