If the Shoe Fits: A Voyeur Story

If the Shoe Fits: A Voyeur Story

Summary: Shoe obsession leads to submissive sexual exploration.

Note 1: This is dedicated to Kevin, who requested this fantasy.

Note 2: This is part 2. In part 1, If the Shoe Fits: A Shoe Fetish Story, A college freshman named Kevin, home for the summer, is looking after his next door neighbours' cat while they're away. Roxy and Mike are a very hot and fit couple in their thirties who also run the gym he goes to. They return home slightly earlier than Kevin expected, and find him fucking one of Roxy's high heels. Which leads Kevin to becoming their extremely willing submissive sex servant, where he orally services Roxy's feet, shoes and pussy, joins her in sucking Mike's cock, and soon gives up his anal virginity to Mike. A real shocker is when the couple mentions in passing how Kevin's parents are also their submissives, one detail of which is how much Kevin's Dad loves giving up his ass to Mike. Kevin returns home that night with lots to think about.

Note 3: Thanks to Tex Beethoven for editing this story.

If the Shoe Fits: A Voyeur Story

The next morning, a Sunday, was surreal.

First, the memories from last night came flooding back and made my dick harden in a heartbeat; Mike had ass fucked me... hard... and I'd loved it.

Second, I'd discovered my Mom eats pussy, Roxy's pussy to be exact, like I already had, and also gets fucked by Mike, just like I was last night.

Third, if that wasn't enough to blow my mind, my father sucks cock and takes it in the ass too.

Surreal!

Wild!

Unbelievable!

Yet it must be true. Why would Mike or Roxy lie?

I was dying to discover how that could possibly have come about, but alas, neither of our next door neighbours would tell me any further details, only saying it was a story my parents could tell me if they wanted to. Which placed me in an awkward position. It wasn't like I could just blurt out, "Hey Mom, Hey Dad, can you tell me how you became sluts for our hot neighbours like I have?"

So as I sat at the kitchen table, my Dad reading the newspaper (yes, we still had the paper delivered to our house every day as if it were still the 1980s) while drinking his coffee, and my Mom making me breakfast (yes, we had a resemblance to a 1950's family too)... I couldn't fathom a scenario where what I'd learned last night could possibly be true.

How did it start?

Were my parents swingers with anyone else?

How long had it been going on?

So many questions, so few answers.

I asked, trying to be a detective, "Do you guys spend much time with the Jacksons?"

"Pardon? Why?" Mom asked, as Dad looked up from his newspaper.

"I don't know," I said, digging for info while also keeping my own secret, "it's just since I've been cat sitting for them, I think they're really nice."

"We do hang out sometimes," Dad said, in a way that didn't at all hint at what 'hang out' really meant.

"Cool," I said. "They seem like really fun people."

"Yeah, we have a blast when we're with them," Mom said, glancing at her husband in a way that I instantly knew this was innuendo I wasn't expected to catch on to, but made my Dad smile ever so slyly.

"What do you four do together?" I asked, as I took a bite of toast to hide any embarrassment or amusement I might show on my face.

"Just hang out," Mom said.

"Cool," I said. "Maybe I can hang out too the next time."

"We'll see," Dad said, as I tried to imagine him with a dick in his mouth or up his ass... which still seemed impossible... but fucking hot!

It was hours later, early afternoon, I was watching television, binge watching the old Magnum PI after watching the new Magnum PI, when I got a text from Roxy: Get over here now!

I didn't need to be told twice. I turned off the television and headed out.

Mom asked, "Where are you going, honey?"

"Just for a walk," I said, unsure what else to say.

"Okay," Mom said, as I headed next door in hopes of having sex with Roxy.

I walked over, glancing behind me to make sure my Mom or Dad weren't looking out the window at me for some reason... which of course they weren't.

I knocked on the door and Mike called out, "Come in."

I walked in, got out of my shoes and went over to him. He was lounging on the couch, naked, watching television, his big cock semi-erect.

"Get naked, sexy," a feminine voice said from the television.

I looked behind me at the sixty-inch television and gasped as I saw Roxy, wearing sexy red lingerie, sitting on a brunette's face. Whatever she was looking at must have been some sort of two-way setup, since as soon as I turned to face the television, she smiled and waved at me.

"H-h-hi, Roxy," I stuttered, waving back.

"I'm at a friend's for the night, and figured you could keep my man entertained for me," she said, as she combed her fingers through the brunette's hair.

"S-s-sure," I agreed, instantly in awe of the beautiful Roxy in such sheer red stockings, picturing her sitting on my face.

"Well like I said, get naked silly," she said.

"Yeah, sorry," I apologized, a little stunned, as I pulled my t-shirt over my head while watching Roxy climb off of the brunette's face.

"No worries, honey," she said, as she stood up and assisted the brunette to her feet.

As I pulled my pants down, I watched as the very pretty, and much younger than Roxy, she looked my age or younger, girl sat down beside her.

"Kevy, this is Amy; Amy this is Kevy," Roxy introduced as I admired the younger girl's small but perky tits, amazing eyes, sexy smile and the slight gleam on her face.

"H-h-hi," I stammered, now in awe of two beautiful women... Amy fully naked except for white pantyhose.

"I think he likes you," Roxy said, as I stood before them in my boxers, which didn't conceal my admiration for them at all... thankfully I'd gotten rid of my tighty whities a little while ago... they really don't flatter anyone.

"He's cute," Amy said, making my cheeks flush red in a heartbeat.

"And he has a nice cock too," Roxy said.

"Mmmmmm," Amy purred, looking at me the way I was looking at her... with intrigue, curiosity, and I think lust.

"Show her, Kevy; show us both that big cock of yours," Roxy said, as her hand went onto Amy's leg.

"O-o-okay," I stammered, this encounter more awkward and exotic than everything else I'd done lately... and the recent list was pretty crazy.

"Don't worry," Roxy encouraged, as I moved my hands to my boxers, "it's a very impressive cock."

Amy actually leaned forward a bit as I nervously pulled my boxers down. "Oh my," the cute brunette said, as she admired my very hard eight-inch cock.

"Told you," Roxy said.

"He's cute, smart, and he has a big dick," Amy said. "You did well, Aunt Roxy."

"Aunt?" I gasped.

"She's not really my niece," Roxy clarified. "She's my best friend's older sister's daughter."

"Oh," I said, that seeming like a Six Degrees of Kevin Bacon game kind of thing.

"And I told her I knew a hot guy she should meet," Roxy said.

"Oh," I repeated, this being the most surreal blind date ever, since I'd never heard of one where both parties began naked, and were on each other's televisions... was Roxy playing sexual Cupid?

"She's even starting college this fall at the same one you attend," Roxy continued.

"That's great," I said, my cock flinching (without even asking my permission), as I spoke with obvious excitement.

"It could be," Roxy said. She smiled as she instructed, "Now fetch the stockings from the table."

"Really?" I asked, noticing at the pink stockings on the table, as well as a red wig. This apparel could end any possibility of a relationship with Amy before it had even started.

"Yes, Amy is like you," Roxy said. "Bisexual."

I hadn't put any thought into the word... that term... one that before these last few wild days wouldn't ever be used to describe me... but now... now... it most certainly did.

I loved women. Pussy. Tits. Legs. Lingerie.

I loved sucking on their tits, caressing their nylon-clad legs, eating their pussies, and of course, fucking them.

I'd recently also discovered my love for cock. And for cum.

I now loved sucking Mike's ten-inch cock, and as of last night, getting fucked by him.

I also, of course, loved the feeling of wearing nylons... it made me feel sexy and feminine... it made me feel like the fuckee instead of the fucker.

Yet what were the odds of Amy respecting... or even understanding... my newfound bisexuality, my cross dressing, or especially my shoe fucking fetish. It seemed unlikely... and yet....

"Oh," I finally said, as I reached down and picked up the pink thigh high stockings.

Possibly sensing my concern, "I love a man who can embrace his feminine side, Kevy," Amy said, presenting me with a very pleasant surprise.

"I'm just discovering mine," I said, her simple sentence and her using Roxy's endearing name for me instantly making me more comfortable about the potential awkwardness of the situation.

I sat down on a chair opposite Mike, who'd remained completely silent ever since inviting me in, and began to put the first stocking on.

Roxy said, "I know this might seem crazy, and hardly the normal way a potential couple would ever meet, and my idea was completely spontaneous, but this could work."

"Maybe it can," Amy agreed, as she obviously enjoyed watched me putting on the stocking.

"You see, Kevy, I came over to look through some photos for a big 30^th birthday party for my friend Jane, who you'll meet at the sex toy party, but Amy's mother Tara is working late at the hospital, so Amy and I decided to kill some time."

"That's quite a sweet way to kill time," I laughed.

"Roxy has been helping me to explore my sexuality ever since my birthday," Amy said.

"Yes, I knew exactly what you needed for your birthday," Roxy said, as a strap-on suddenly was in her hand and within my view.

"Best present ever," Amy said.

"And now you really know how to fuck," Roxy said.

"And to eat pussy," Amy added.

"And to suck cock," Mike chipped in, doing something on his phone... his dick still just sitting there, likely waiting for some attention from me.

"Just like your Mom," Roxy said to Amy.

"Yes Kevy, she knows I'm Roxy's submissive pet," Amy said. "And she approves. But I don't think she'd like you playing matchmaker, Auntie."

"No? Why not?" Roxy asked, as I finished the first stocking.

"I don't know for sure," Amy said. "But I think she might still be hoping I'm a complete lesbian."

"But you love cock too much to be a lesbian," Roxy pointed out, as I slid the second stocking up my leg.

"I sure do," Amy said in a sexy voice. "Especially a nice big one."

"Hey, I have one of those," I joked, trying to go along with this crazy situation.

"Yes, you do," Amy and Roxy said simultaneously, both in a sexy as fuck tone.

"Thanks," I said.

"I have a big cock too," Mike pointed out, just as I finished with the second stocking.

"We haven't forgotten about you, Mike," Roxy smiled.

"You'd better not," Mike said, as he stroked his big cock, that had been in both of my holes just yesterday, and was now completely hard.

"Never," Roxy said.

"Yes, Uncle Mike, you have quite the fuck stick there," Amy said, which instantly made me assume everyone in this conversation had been fucked by Mike's fuck stick.

"Don't you forget it, baby girl," he smiled, as I stood up, now decked out in pink stockings.

"Ooooooh, you're so cute," Amy purred, turning her attention back to me. I noticed Roxy wasn't sitting beside her anymore.

"You're okay with this?" I asked, feeling feminine and sexy... and not masculine at all... which I assumed would be a detriment for whatever this thing between Amy and me might or might not be.

"Yeah," she said. "I want a man who's comfortable with his sexuality, able to invest himself in his carnal lust, and...."

"And what?" I asked, dying to hear what the third thing was.

"And who has a nice big cock," she smiled.

"As do I," Roxy said, now back in the picture and wearing the birthday black strap-on.

"Oooooh, nice," Amy smiled.

"Kevy, I want you to put the wig on for me," Roxy said.

"Yes, Kevy, let's get you looking all sexy and girly for us," Amy added, as she stroked the fake cock in front of her face.

"Okay," I said, as I fetched the wig.

Once I had it on, and could feel the hair on my back, I felt a rush of feminine excitement. I wondered what I looked like.

"So sexy," Amy said.

"Yes, she does look sexy," Roxy agreed, using a feminine pronoun for me.

"I feel sexy," I said, as I posed girlishly with my hands on my hips.

"Nice, very nice," Roxy said. "Now are you ready to be me for the night?"

"Y-y-yeah, I-I guess," I stammered.

"Good, so you and Amy will be doing the same things at the same time," Roxy said, as Mike stood up.

"Knees," Roxy ordered, and I watched as Amy obeyed and slid onto the floor in front of the huge black strap-on cock.

"You too," Mike said, as I stared at the big television screen.

I mindlessly obeyed, trying to focus on two things are once. The very pretty Amy in her knees slowly stroking the fake black cock, and Mike's big hard ten-inch cock right in front of me.

"Take our cocks in your mouths, my sexy sluts," Roxy ordered.

I watched Amy glance to me, smile playfully, and then take the black cock in her mouth.

I turned to Mike and took his big cock in my mouth.

"That's it, suck those cocks," Roxy purred, as I slowly bobbed, and assumed Amy was doing so as well.

I slowly sucked Mike's cock, enjoying the thrill of having it in my mouth while Roxy watched. Although I hadn't originally seen myself as a guy who'd suck cock or get ass fucked, now that I'd done both with Roxy's encouragement, I'd awakened another side of my sexuality I hadn't even known existed.

Licking pussy is amazing.

Fucking a woman is amazing.

Fucking a high heel is amazing.

Sucking cock is amazing.

Getting ass fucked is amazing.

I'd become more a man by becoming less of one... which I know is a strange contradiction of terms.

"Tonight Kevy, you're being me, and you're there to pleasure my man just like I would," Roxy said.

"Mmmmmm," I moaned on his cock in response, as I slowly sucked the nice hard cock.

"Let's fuck," Mike said, after a couple of minutes of me slowly sucking him, wishing I could see what was happening on the screen.

"Let's," Roxy agreed, as he pulled his cock out of my mouth, and I quickly turned to watch the strap-on leaving Amy's lips.

"Auntie, may I please watch Kevy get fucked while you fuck me?" Amy asked.

"Of course, honey," Roxy said, and they rearranged themselves, including moving to a different location.

As they did that, I got on all fours facing the television so I too could watch.

Mike asked, as the women reorganized themselves, "What do you think of Amy?"

"She's really hot," I answered.

"Yeah, she is," Mike agreed. "And she's really sweet too."

"The perfect girl," I said.

"And a slut who will do pretty much anything," Mike said as he lubed up his cock.

"The icing on the cake," I said, fascinated by this girl I'd only kind of met so far.

"You already look ready," Roxy said, as she came over to Amy, who was on all fours and looking at me.

"Hey Kevy," Amy said, rather casually... as if we were just meeting somewhere and not about to be fucked by a married couple.

"Hey Amy," I replied, as I felt Mike moving his cock to my ass even as I was mesmerized by this cute girl... with the perfect sweet girl next door vibe.

"So, weird first date, huh?" Amy asked.

"This is a date?" I asked.

"A blind date," Roxy said, as she ripped Amy's pantyhose.

"We certainly won't be able to tell our kids how we met," I joked.

"We could," Amy said, "we'd just have to leave out some details."

"Like how hot you look naked," I suggested.

"Or how much I like the looks of your big, hard cock," she tossed back.

"I guess," I laughed, finding the most authentic if surreal connection with a girl on a screen in the most surreal of situations. I mean what were the odds I could meet a girl this way... or that she'd be okay with my very kinky fetishes, although I didn't know if she knew about my shoe fucking one yet.

"You two could go on a real date tomorrow, or some other day soon," Roxy suggested.

"But now it's time to fuck," Mike added.

"I'm free tomorrow evening," Amy said rather quickly, seeming to want to get to know me better, just as much as I wanted to get to know her better.

"For sure," I replied, excited about the opportunity for a real date with her.

"Aaaaaah, I knew you two would hit it off," Roxy said.

"Enough romantic shit," Mike said.

"Ignore him, he forgets how romantic he used to be," Roxy said.

"Fuck me, Roxy, I'm so horny," Amy said, breaking our brief romantic interlude, as she also broke eye contact to look back at the redheaded beauty.

"Yes, fuck me, Mike," I added, wanting Amy to see me getting fucked as I watched her getting fucked... somehow trusting she wouldn't find me less manly for taking a dick in my ass... which was promising, since I was already in thigh high pink stockings and a wig at the moment.

"On three," Roxy said.

"Count fast," Mike said, his cock positioned at my no longer virgin hole.

"Just shove it in," Amy begged, assumedly Roxy's dick poking at her pussy,

"One, two, three," Roxy counted quickly and with a bit of a chuckle, as Mike's cock slid into my ass and like last time, the pleasure-pain principle went to work as I moaned, while a burning sensation coursed through my body and my rock-hard cock throbbed.

"Oh yes," Amy moaned as her pussy was filled. "Fuck us, fuck your sluts."

I looked up and saw Roxy fucking Amy while Amy was looking right back at me.

"You two are darling together," Roxy said, as we both got fucked. "Don't you think, Mike?"

"It's the weirdest matchmaking I've ever seen," Mike said, as he slowly fucked me, thankfully giving me time to get used to his big cock in my ass.

"Mmmmmm, are you going to take me on a real date, Kevy?" Amy asked, looking at me with the sexual glazed look of a woman in the throes of pleasure.

"I'll do anything for you," I moaned, as I was taking all of Mike's dick, and after a couple dozen slow strokes, the pain was beginning to fade.

"Ask her out, Kevy," Roxy said, as she began fucking Amy faster and Mike followed her lead, picking up speed and power as he now slammed into me for our mutual pleasure.

"Fuuuuuck," I moaned much more like a woman than a man, as he reached new depths, now creating a new pain, a new pleasure.

"Fuck him, Mikey, fuck him good," Amy said, seeming to really enjoy watching me get fucked.

"Oh Amy," I moaned, trying to get up the nerve to say the words, and also the mental acuity, since Mike was really giving it to me by now.

"Yes, Kevy," she moaned too, as Roxy was equally really giving it to her.

"Will you," I began, the pleasure consuming me, my cock throbbing from the really deep, hard pounding, "will you... go out... on a... oh fuck...."

"Well, that's pretty forward of you for a first date," Amy teased, as I could feel my orgasm rising intensely and rapidly inside of me.

"No, no, I meant..." I struggled to correct myself as Mike really railed my ass, giving me such intense pleasure.

"But sure, I'll be glad to fuck you," Amy agreed, although I wasn't sure if she meant have sex where my dick was inside her, or she meant fuck me with a strap-on.

It didn't matter what her intentions were, her wicked words, mixed with Mike's rough pounding, and then his sudden without warning massive cum deposit in my ass, had me spewing my load all over the floor, as I bellowed, "Oh fuuuuuck!"