If the Shoe Fits: A Voyeur Story

"That's so hot," Amy moaned, her eyes bright as she watched me cum.

"Such a tight asshole," Mike grunted, as he kept pumping his load into me.

"Kevy, you're such a sexy slut," Amy purred, really enjoying seeing me getting fucked and cumming.

"As are you," Roxy said, really pounding Amy.

"Please don't stop, Auntie," Amy moaned, clearly close to an orgasm herself, as I remained on all fours, watching Amy with all my focus, as Mike pulled out of my ass and I felt cum oozing out.

"Come for me, slut," Roxy demanded, really giving it to Amy.

"Oh fuck, yes, fuck me, fuck me, fuuuuuuck," Amy babbled, closing her eyes as her orgasm rose, and then erupted through her. In porn, watching a woman come was incredibly hot... but watching it live, even on a television screen, was even more delicious. Amy looked so beautiful in her vulnerability as she surrendered to the pleasure cascading through her.

I was entranced by what I was watching, not budging from my submissive place on all fours, even though Mike had pulled out.

After another minute, Amy opened her eyes and asked, "Did you enjoy watching me getting fucked, Kevy?"

"I plead the fifth," I said, even though it was obvious I had.

"I really enjoyed watching you get fucked," she said, as Roxy pulled out.

"I'll let you two plan your date for tomorrow," Roxy said, "But then Amy has some pie to eat."

"Actually, she never said yes to the date, just to fucking me," I pointed out.

"Yes, I'll certainly go on a date with you, silly," she smiled.

I looked behind me and saw I was alone too. I took the wig off and asked, "Dinner and a movie?"

"Sounds great," Amy said. "Although perhaps a little anti-climactic after today."

I laughed, "I'm sure we can make sure to include a climactic experience."

After a brief pause, I asked, having learned at college not every family was like mine and ate at five or five-thirty... my Mom's diabetes meaning she had to eat at regular times, "Are you a dinner at five person or a dinner at seven person?"

"Definitely seven," she said.

"Then I can pick you up at six-thirty," I offered.

"Sure," Amy agreed.

"Hurry up, this pussy isn't going to eat itself," Roxy called out, presumably from a bedroom.

"Duty calls," Amy smiled. "I'll get your number from Roxy, and maybe we can chat later tonight."

"I'd love that," I said, finding how I'd gotten a date simultaneous with cross dressing and being ass fucked pretty surreal.

"Bye," she said, blowing me a kiss.

"Bye," I said, as I watched her get up and walk away, getting a nice glimpse of her torn pantyhose-clad ass.

I got up, took the nylons off, got dressed and left.

Two hours later, I got a text from an unknown number: Hi sexy, time to chat?

Pretty confident it was Amy, I replied sure, and asked if we could Facetime. I hated texting.

Two minutes later, we were both on our laptops and I was looking at the very pretty Amy. She was fully dressed now, not particularly sexily, just casually, like I was. We chatted for almost two hours. Not once mentioning what had happened earlier in the day. We chatted about school, family, travel, music, movies, summer plans, fall plans, where we looked forward to seeing each other at college, and other random things. It was the most relaxing and comfortable conversation I'd ever had with a girl.

Then out of the blue she asked, "Will you do something for me?"

"Sure, what?" I agreed without any hesitation, without even knowing what it was... yet after a shared twisted sexual encounter and a two-hour conversation, I already knew I'd do anything for this girl. I'd never been in love, so I had no idea if I loved her... but in some way I did know... I was strongly enough attracted to her, that this was very likely love at first sight.

"May I watch you fuck a shoe?" she asked.

"P-p-pardon?" I stammered, having heard her question, but was stunned by it.

"Roxy was telling me you fuck her open toed heels," she said. "That sounds so hot."

"Oh," I said, her knowing this somehow more embarrassing than being sodomized while dressed in thigh high stockings and a wig.

"You can watch me fuck my pussy while I watch you do it," she offered, lowering her phone to show me her completely shaved pussy. I'd thought she was demurely dressed, while the vixen had apparently been naked below the waist the entire time!

"I don't have a heel here," I said, as I admired her pretty pink pussy.

"If you go downstairs and just outside your front door, I believe Roxy has left you a gift," she said.

It was after midnight, my parents were definitely both asleep, as I asked, "Really?"

Amy brought the camera back to her face and said, "Yeah, something sexy, I was told."

"You really want to see that?" I asked, thinking it was a very weird perverted thing.

"Yeah, I want to watch you fuck a heel, and I'll go and select a nice cucumber for you to watch me fuck myself with," she offered.

My eyes went wide, my already hard cock flinched in my boxers, and I said, perhaps a little too eagerly, "I'll be right back."

"Me too," she said.

I quietly left my bedroom, tiptoed down the hallway, opened the front door, and saw a black five-inch heel sitting on the doorstep.

I quickly picked it up, closed the door and returned to my bedroom. I stripped and got back onto my bed.

I waited a couple minutes, my cock throbbing, admiring the sexy heel, fuck was it a sexy shoe, when Amy returned and asked, holding up a cucumber, "What do you think?"

It was huge! I joked, "I think I'm going to be a disappointment."

"Oh, I'm sure you'll fuck me good when we have the chance," she smiled, and then asked, "Let me see the shoe."

I lifted it up and showed it to her.

"Mmmmmmm, that's a very sexy shoe," she said.

"I bet it would look great on you," I said smoothly.

"With or without a load of cum in it?" she asked.

"Your choice," I smiled, in awe that my perversion was turning her on.

"So how do you fuck a shoe?" she asked.

"Not easily," I said. "It'd be easier if someone was here to hold it."

"Mmmmmm," she moaned in a very sensual tone. "I'd love to be there to watch you fuck that shoe."

"And I'd love to be there to watch you fuck yourself with that huge cucumber," I said, as I pondered how exactly I was going to fuck this heel.

"You mean this cucumber?" she asked, as she put it to her mouth and slid it inside... taking a good eight inches into her mouth!

"Oh, God," I gasped, as I watched her deep throat the cucumber.

"Mmmmmmm," she purred again, making my cock long for her.

As she pulled it out of her mouth, she asked again, "So how exactly do you fuck a shoe?"

"It's not easy," I repeated, looking around. "The key is to get the shoe lodged someplace where it can't easily move."

"I see," she said, and she pulled her t-shirt off and slid the cucumber between her perky tits and shivered... her nipples instantly hard.

"Although if you keep doing stuff like that, I may shoot my load before I even get to the shoe," I said, kind of joking, but kind of not... it was somehow natural to have such a strange sexual conversation with a girl I'd just met hours ago... online....

"Well, we can't have that," she said, as she took the cucumber away from her tits.

"I have an idea," I said, as I got off the bed and grabbed my overpriced but handily heavy first year textbooks off the shelf and used them for something productive for once. I placed one on each side of the heel, and one behind, and had the open toe angled up slightly.

"Creative," she said.

"I'm a creative guy," I said, then realized how odd that sounded.

"And a cute one," she smiled.

"Thanks," I said, flattered by her compliment. "You're beautiful."

"Now you're lying," she said.

"No, I mean it," I replied, sensing that behind that self-confident sexual submissive was an insecure girl.

"You're sweet," she said.

"I think you're amazing," I said.

"That's only because you saw me get fucked," she said.

"Do you really think that?" I asked.

And for all of her sexual bravado, all her raw passion, all her wicked words, she was still at heart a girl needing to be loved. Like Julia Roberts' character in Notting Hill, or Kate Beckingsale's character in Serendipity... and our meeting and the cascading dominos series of events that had to take place for it to occur was the ultimate example of serendipity.

It was like Fate (in the person of Roxy) had brought us together.

Like Cupid had shot arrows into us both.

I couldn't explain why, I really couldn't, but I'd never felt like this about a girl... ever... and it wasn't just sex... it was something completely different... something that was making my heart beat faster and was shaking me to my core. Again, was this love at first sight? Even if it wasn't, it was pretty damn overwhelming.

"I don't know," she said, looking sheepish and very vulnerable.

There's something so heartbreaking about seeing a sad girl, but also something so beautiful about her open vulnerability. I said, "I know we've only just met, and under very strange circumstances, but I'm not just saying this: I really feel a deep connection with you, and it's not because of the sex. It's something else. Something I can't explain. Something bigger than you or me."

"Serendipity," she said.

"Did you just say serendipity?" I asked.

"Yes," she nodded. "Because I feel the same. I feel as if every moment of our lives was planned to bring us to this moment."

"I was literally thinking the same thing," I said.

"No way," she said.

"I'm serious. I literally was thinking how this connection was just like the connection between John Cusack and Kate Beckingsale in...."

"Serendipity," she said, finishing my sentence.

"Exactly," I agreed, now feeling an even stronger connection with her.

"You've seen that movie?" she asked.

"Many times," I nodded.

"I've never met a guy who's even heard of that movie, never mind liking it," she said.

"I bet you've never met a guy who knows what the word means," I smiled.

"No, I don't think I ever have," she laughed.

"It's my favourite movie," I said.

"Mine too," she nodded, looking at me with a sense of perplexed awe... and serendipity.

"Then you believe this was meant to be," I said.

"I'm beginning to think I don't have any choice," she said.

"Wow," I said, forgetting about the shoe, forgetting about the lucky cucumber, almost forgetting about my being able to see her tits and her hard nipples... I was just inhabiting this moment, and I didn't want it to end.

"Yeah, wow," she said.

"So, now what?" I asked.

"Well for one thing, let's not lose track of each other, so we won't have to go through all that drama to find each other again!" she laughed.

"Good idea!" I laughed in return.

"And," she said. "Even though that was a very special moment, and my entire body is filled with warmth, I still want to watch you fuck that shoe."

"And I want to watch that lucky cucumber filling you right up," I said.

"Then let's entertain each other," she said, as she brought the cucumber between her legs.

I reached for my lube and generously lubed my cock.

"Yes, get that cock lubed up for that shoe pussy," Amy moaned, as she pressed the cucumber between her pussy lips.

"I'm going to fuck this heel imagining it's your pussy," I said, as I moved my very slippery cock towards the tight open toe of the heel.

"Mmmmm, and I'm going to fuck myself imagining this is your cock slamming into me," she countered. "Can you angle your laptop down a little? I can't see the entire shoe."

"Okay," I said and then asked after moving it, "Better?"

"Perfect."

"Like you."

"Ah," she smiled, the cucumber just resting between her pussy lips. With my cock head at the small entrance, Amy asked, "Now fuck that shoe pussy."

"I love when you tell me what to do," I said, hinting at my natural submissiveness.

"Okay, then you'll be my bitch whenever I want you to be," she promised. "Now like Roxy said before, on three."

"Okay," I agreed, feeling a wild rush of excitement that I was about to fuck this shoe in front of someone who was perhaps my new girlfriend, and definitely my potential girlfriend.

"One..." she said, drawing the short word out for a couple of seconds.

"Two," I counted up, as I watched her rub that cucumber up as if she were stroking my cock.

"Three," she said, and slid the cucumber into her pussy. I was so preoccupied watching the green vegetable fill her I forgot to do my part.

"Kevyyyy," she squealed, "fuck that damn shoe pussy!"

"Sorry, you're just so distracting," I said, as I looked down at the shoe, pushed forward, wiggled my cock just a little, and slid it inside the tight, creative pussy.

"Sooooo hot," she moaned, as she pumped her pussy while watching me do inappropriate things to a sexy heel.

"You too," I said, as I began slowly to fuck the shoe.

"Yeah, fuck that shoe, Kevy, give it that dick," she moaned, really turned on it seemed, by watching me performing such a wicked act for her, and her wicked words only enhanced the sensual kinky act.

In just several hours she'd seen me kind of cross dressed, sucking a cock, getting fucked by that cock, cumming from getting anally pounded, and now using a heel to masturbate with... this was easily the strangest first kind of date in the history of mankind.

"You like this?" I asked, as she seemed entranced by watching me, as I realized in those same several hours I'd seen her having her face sat on, getting fucked from behind by a strap-on, walking her really cute ass away to eat Roxy's pussy, and now fucking a cucumber... while not as extreme as my list of kinks, still pretty kinky.

"I doooo," she moaned, as she fucked her pussy good.

I slowly fucked the heel, knowing the tight friction, mixed with watching Amy fuck herself, talk nasty, and the erotic voyeuristic act, was going to have me coming pretty quickly if I fucked it too fast.

"Oh Kevy, fuck that shoe, destroy that pussy, fuck it good," Amy urged me, all with soft sexy moans, as she was fucking herself rapidly with her makeshift fuck stick.

"I won't last long," I warned, wanting this wild encounter to last as long as possible.

"Oh Kevy, I'm not going to last long watching you fuck that shoe and admiring your cute ass," she moaned. "Just fuck it like Roxy fucked me."

"Okay," I said, noticing my setup wasn't completely working. I reached down and gripped the back of the shoe as I began pumping faster.

"Oh yeah, give it to that shoe, fuck it, hammer it good," she moaned, as I glanced over and watched her furiously fucking herself while watching me intently, even lifting up her ass while she fucked herself.

"Yeah, fuck yourself too," I said, as we watched each other fucking things or being fucked by things never intended for that purpose.

"Oh yes, Kevy, yes, fuck that shoe pussy, fuck it, fuck it hard," she continued, watching me, fucking herself and talking nasty seeming to bring her close to orgasm... which was good, because I too was close.

"Oh yeah, shoe, take my cock," I said awkwardly, talking dirty to an inanimate object, knowing I was close, and desperately trying to hold on as long as I could.

"Yes, Kevy, don't stop, don't stop fucking that shoe! Fuck it Kevy, fuck that shoe pussy, fuck it, fuck it, fuuuuuuuuck it!!" she cried as she fucked herself fast, bucked her ass to take it as deep as humanly possible, and I fucked the shoe as fast as I could until she came.

Once she came, I didn't hold back any longer, and a dozen strokes later, I grunted and filled the inside of the shoe with a massive load.

"Yes, Kevy," she moaned, although a lot more softly now as she enjoyed her orgasm, the cucumber lodged two thirds in her pussy while she watched me spewing into a shoe.

"Fuck," was all I could muster, the wild encounter and orgasm usurping all the energy in my body.

Once I was done, she ordered, "Show me the cum."

I decided to keep my cum-coated dick in the shoe as I brought it and my cock close to the computer camera.

"Fucking delicious," she said.

"Let me see that cum-covered cucumber."

"Nice alliteration," she smiled as she pulled it out and a gush of cum squirted out of her and even onto her computer. "Sorry, I squirt... a lot."

"Yummy," I said, both to that, as well as to the very wet cucumber.

"Likewise," she said, as she inspected the large load in the heel.

There was an awkward pause while we each considered now what. Finally she said, "I should get to bed. I have school in like seven hours."

"Right, you're still in high school," I said, having forgotten that completely. I asked, in joke form, but actually kind of curious, "you're eighteen?"

"What, no. I'm only sixteen," she said, deadpan.

"W-w-what?" I stammered.

"I'm kidding," she roared with laughter... even her laugh was sexy. "I turned eighteen three months ago. Remember how Aunt Roxy gave me that birthday present?"

"Thank God," I said, mockingly wiping sweat off my head, and then realized I did have some sweat on my head.

"So, see you tomorrow at six-thirty?" she asked.

"Definitely," I said.

"I'll text you my address," she said. "You can meet my Mom."

"I can't wait," I said, wondering what the Mom of such an amazing girl would be like... plus, she was friends with Roxy.

"Yeah, I think she and Roxy are still fucking," Amy said.

"Roxy is still there?" I asked, surprised.

"She was when I went to fetch the cucumber. She was ass fucking Mom while Mom was eating out our neighbor," she said casually, as if this was as normal as walking in on a bridge game.

"No way," I gasped.

"Yeah, my Mom is a submissive like me, well, actually I'm a switch, and she only eats pussy," she said.

"I see," I said.

"I assume you eat pussy," she said pointedly.

"You assume correctly," I said. "And I can't wait to prove it to you."

"Well, goodnight, Kevy," she said, yawning and stretching her arms, showcasing her perky tits.

"Night, Amy," I said.

She blew me a kiss and logged out.

I logged out too and looked down to see I still had my dick in the shoe.

I shook my head and gave my cock time to shrink before pulling it out of the well fucked shoe.

I put it on the side of the bed, cum still in it, closed my laptop, shut off my lights by clapping twice (yep, I had the clapper... eBay is cool).

Suddenly exhausted, I closed my eyes and wondered what tomorrow would bring.

The end