"Swiping Right" with Hilary Duff
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With Hilary Duff
Written by TPG (inspired by a dream)
CODES: MF, public, kissing, fingering, blowjob, anal
DISCLAIMER: This FICTIONAL story was written for entertainment purposes only.
If someone had told me a few months ago that one day I'd score a date via social media, I would have laughed in their face but that's precisely what happened. In fact I wasn't even looking for anything "serious" when I loaded up the Tinder app, and I watched it locate and match me with people in my area - with the implication of hooking up for a quick fling.
I guess living in the surrounding suburbs of Hollywood had its benefits, and I should have expected that I'd see a few familiar faces, but even I was surprised by the way things turned out. Amusingly enough I was initially let down with the app's results and almost considered deleting it from my phone when I was suddenly matched with "Lizzie27" who was just 4 miles away.
Given my recent experience with dating, I made it clear from the start that I wasn't looking for a "soulmate" but simply wanted a bit of casual fun. I was pleased to learn that "Lizzy" had similar intentions, and we soon began to text back and forth until she finally sent me her phone number.
I honestly didn't know what to expect, particularly since she had used an old promotional photo of the Disney character Lizzie McGuire for her profile pic, so she was obviously self conscious about the way she looked.
But when she answered the phone I was relieved to hear her speak in a sweet and confident manner, and we ended up talking till midnight - two complete strangers comparing notes on life, love, and prior experiences, during which we both agreed on the importance of "chemistry" and the lost art of kissing.
"I think a lot of people take kissing for granted." she stated at one point, and I had to agree.
"Yeah. Sometimes if you meet the right person it can almost be as powerful as having sex."
"I know right!"
Our conversation was comfortable and easy. We didn't have to force any topic and easily opened up to each other, telling one another some of our most intimate experiences. As the hours passed "Lizzie" finally said that she needed to get to bed, so I wished her a good night and assured her that I wouldn't contact her again until SHE made the effort and reached out first.
"—but what if I want you to chase me?" she teased. "Maybe I like that sort of thing."
"I guess we'll play it by ear. " I replied. "Besides. I like to keep things fun and spontaneous."
"Hmm. Good answer."
She smiled and hung up the phone, and I felt like we had made a genuine connection. In fact a few days later I found myself thinking about her again and decided to sent her a quick note.
"I know I promised not to contact you," I wrote. "But I'm free at the moment and figured I'd say hi."
She texted back almost immediately.
"Speak of the devil. I was just thinking about you."
"Good thoughts I hope."
"I was just wondering if you wanted to meet up?"
My jaw dropped, even though it was exactly what I had been hoping for. We arranged to meet at a local coffee shop within the hour. I barely had time to change before I drove across town to make it to the impromptu date.
Fortunately for me the traffic was light and I managed to arrive with just a minute to spare. But as I climbed out of my vehicle, I glanced across the parking lot and recognised her sitting in her truck, playing with her phone. I almost shit my pants when I realised that the woman I was there to meet, the girl I had been flirting with on the phone, was none other than the actress and singer Hilary Duff!
Suddenly her profile pic made total sense, as Duff had portrayed Lizzie McGuire back in the nineties. I walked towards her large SUV and smiled as she looked up and recognised me immediately - all of my "plans" and schemes flew right out the window.
"Lizzie?" I asked.
"Are you freaking out right now?" Hilary grinned, referring to the fact that her true identity had been revealed.
"Err, a little." I admitted. "This is like an episode of the Twilight Zone or something."
"Are you disappointed?"
I assured her I wasn't, but was still a little shocked to discover that her identity matched the photo. I then held the door for her to get out of her truck, before we entered the coffee shop together.
With our drinks in hand, Hilary nodded her head to the side summoning me to follow. Her table of choice was somewhat secluded, tucked around a corner beyond the main area. Strangely enough it didn't take long for us to chat like we were old friends, instantly comfortable with each other while the conversation drifted on to more conventional topics.
This only seemed to heighten the tension between us. Not addressing the mutual attraction we had was just the perfect sort of denial. We talked about work, weather, and funny moments online. But just when I thought the day couldn't get any more surreal, Hilary seemed to contemplate something and then spoke her mind.
"So tell me the truth. How bad do you want to kiss me right now?"
"Excuse me?"
The singer blushed.
"I mean, we're obviously attracted to each other."
"Obviously."
"—and I have to admit I've been thinking about it ever since that first phone call."
"You have, huh?" I grinned. "You really don't believe in wasting any time do you."
"Why pussy-foot around?" she shrugged. "We both know we like each other. We should probably see if we're physically matched too."
"Physically matched?"
"Kissing, I mean." she clarified with a grin.
Our conversation on the phone had highlighted her fondness for kissing, so while I kind of anticipated the topic, I wasn't expecting things to progress so quickly. I struggled a bit with my coffee as I suddenly wondered if she meant getting down to "business" right away, and prepared myself to lean across the table to kiss her on the lips.
But Duff matter-of-factly pulled out a lipstick-sized breath spray, and spritzed her mouth a couple of times before offering me the same treatment.
"Go ahead. It's peppermint flavor."
"Great." I chuckled, finding her OCD strangely charming.
Thankfully the spray was pleasant, and I didn't pass out and wake up to find myself tied to a bed with my liver missing.
I suppose Hilary just took making out a lot more seriously than I thought. Being an actress as she was I suspect she had a time and tested routine. Unfortunately for us, just as we were about to take things to the next level we were interrupted by her phone, which forced me to sit there awkwardly as she conversed with her friend (agent)
Amusingly enough, Hilary sat there throughout the call flashing me a playful grin, knowing how anxious I was. In fact I dare say she actually got off on it, knowing how frustrated I was by the rude interruption and mere notion of sharing a kiss with her.
When she finally hung up the phone she then reached into her bag and applied some shiny lip balm to her lips, which completely confused me as I now wondered whether or not we were still going to make out, or had she changed her mind about the whole thing?
My heart then sank when she collected her things and claimed that she had to run. We got up from the table and I followed her out to her truck, kicking myself for wasting what little time we had together and letting any opportunity to kiss a celebrity slip by. I held the door open for her as she climbed into her large truck and opened her window.
"We should probably do this again." she smiled while starting her G-Wagon.
"I guess, but we never did get to that kiss."
There was a long pause before Hilary smiled and nodded her head.
"Come here."
I stepped forward and placed my head through the window allowing our lips to meet - the contact between us absolutely electric. In fact the kiss was so incredible that I vaguely remember reaching in to place my hand on her neck and felt her respond by brushing the tip of her tongue across my lip.
I instantly responded by sliding my hand around her waist, almost pulling her towards me through the window of the vehicle and causing her to sigh into my mouth. To her credit we never broke contact with our lips, even as my hands began to wander around. At one point I heard her coo, just a tiny expression of excitement before pulling back and telling me to get in the truck.
I didn't need to be asked twice, and quickly hopped around the vehicle and climbed in. So much for her having to be someplace, I thought.
Within seconds Hilary was on me like white on rice, her tongue snaking into my mouth, probing wildly as if battling mine for supremacy. I was only too happy to oblige, and tongued her back with the same amount of force she showed me.
That was until she finally pulled back slightly and helped slow down the pace and focus on just using our lips - our noses periodically switching sides as we kissed each other slowly and sensually.
All I could taste was her frothing saliva mixed with lipstick, as we let spit build up in our mouths before French-kissing one another over and over. Our kissing took pauses. Short pauses. Long pauses. Tongues were sucked. Lips were bitten. Large amounts of spit were swapped.
"ugh. I really have to go." she finally whined, her plump lips gleaming wet.
I responded to this by giving her an innocent farewell peck on the cheek, which quickly set off another series of kisses and probing from the two of us. We just couldn't keep our hands off each other! ...at least long enough for us to say our goodbyes.
With nothing to lose, I took this opportunity to place my hand on her hip and slowly slid it up until I was cupping the side of her breast. It was a bold move to be certain, and one I wasn't sure would be welcomed, but she countered this by sticking out her chest and pushed her tongue deeper into my mouth.
Duff then reached down and squeezed the straining cock in my pants, the unexpected action almost made me jump out of the seat.
"Mm-Yeah. I bet you've got something down there for me." Hilary purred while palming the huge bulge.
Her actions literally rendered me speechless, as the singer then proceeded to unzip my pants, all the while glancing at the clock and arguing with herself about not having enough time to have fun.
"—ugh. We don't have much time." she mumbled between kisses, while taking me out and stroking my bare cock directly in her hand.
I eventually found my bearings and countered in kind, reached up under her shirt to fondle her ample breasts directly through her bra. Even through the lace fabric I could feel how erect her nipples were, and massaged her tits accordingly.
As we resumed kissing (hotly) I worked one of her bra cups down to give me full and unfettered access to her entire breast, squeezing and kneading the soft flesh. Hilary moaned and picked up the pace of her stroking and now jacked me off a little faster - her sexy green eyes burning deep into my retinas.
"—think you can come right now?" she whispered seductively, urging me to hurry up and shoot my load.
I responded by circling her nipple with my finger and pinched it between two digits, which caused her to gasp and literally melted in my arms. It was at this point that I slid my hand down her body and towards her pants, hoping to give her a piece of her own medicine.
"You know, two can play at this game." I said as we simply sat there panting and staring into each others eyes.
The actress watched silently as I fumbled with her pants and finally shoved my whole hand inside. To her credit she didn't object and just blinked back at me, as I ultimately made direct contact with her hot, smooth mound. When I felt her swivel her hips and push my fingers against her cunt, I knew I had all the permission I needed and I proceeded to stroke the length of her pussy - feeling the soft texture of her thick rubbery lips.
"Lizzy" was now trying to control her breathing, letting out long, deep, shallow gasps. She soon began to squirm and gyrate her hips, matching my rhythm with her own, though she tried not to show it.
Every time she opened her mouth to try and say something I'd interrupt her with a deep kiss. Ultimately she just gave up trying and gave herself over to the moment, spreading her knees wide to accommodate my hand.
I added more pressure to her pussy, and paid special attention to her grinding hips as they now dictated what she wanted. In truth, I had only intended to tease her a little before sending her on her way, but the singer was now on the verge of experiencing an rather powerful orgasm.
Her bucking had become less controlled, and her eyes were almost shut, her mouth hung open.
I was going to make her come right then and there in the parking lot, in board daylight no less. It was only when I heard myself groan that I realised her hand was still pumping my cock furiously. In fact she was doing such an exceptional job of jacking me off that pre-cum now leaked from the tip which only seemed to encourage her.
"You have to come." she whispered breathlessly. "I'm serious."
"You first."
"ugh-god."
"I'm not letting you leave until you come Hilary." I told her. "Not until you come all over my fingers."
Suddenly, her legs clasped shut and an orgasm ripped through her - bringing her hips up off the seat to hump against my hand. With the last few thrusts of her hips, she suddenly began kissing me hard on the mouth again before pushing me back into the seat and lowering her blonde head into my lap.
I let out an audible moan as I watched her suddenly take me into her hot mouth!
"Jesus."
I felt light-headed from the action and was forced to muster all of my will-power not to explode right there. Hilary pulled back slightly, swirling her tongue around the tip before abruptly dropping it back down, this time engulfing my entire staff in one go.
The action sent tremors up my spine as her free hand came up and began to fondle my balls, while her head proceeded to bob up and down with a more regular motion.
"fuck fuck fuck." I squirmed in my seat as the one time Disney star sucked my dick.
I grabbed a fistful of her blonde hair and pulled her mouth off of my cock, only to hear her groan lustfully to the aggressive gesture. Then turning her face to the side, I smacked my cock against her mouth and chin, causing her to groan and grunt lustfully.
"Unngh-Yeah." she groaned erotically. "Slap it against my face. I like that. More!"
In an instant her mouth opened and she devouring me again, as I began to shove her down harder and harder on my cock, thrusting deep into her throat with my hips. My actions were greeted with an animalistic moan from the mewling star.
I felt pressure building in my balls as I quickened the pace, until I could bear it no longer. With a half-moan, half-yell, I thrust one final time, burying her face in my lap, my cock pumping its load into the depths of her narrow throat.
I felt Hilary gag and gasp for air, but could not stop as my cock jerked painfully hard, shooting wad after wad hot syrupy spunk into her famous belly. I literally crumpled back into the seat as she came up for air, still licking my hard shaft, slurping up the cum that had dribbled down the side of my penis.
Her movements were almost frantic like those of a starving animal, and she was making desperate little groans as she lapped at my balls with her tongue. My head was still spinning when Duff suddenly grabbed my spent cock and looked me deep in the eyes.
"Ugh. I wanna fuck." she hissed. "I wanna fuck you right NOW!"
I needed no further motivation to kiss her hard and pull her over the middle console and onto my lap. Her hands struggled to push her pants down to her knees before my cock was greeted by the heat of her sex. I quickly moved the seat back to give her more room to get comfortable as we kissed each other zealously, feeling the intense heat of her pussy as she lowered herself down on me.
All things considered it was an incredibly awkward place to have sex, but we were so worked up and "in the zone" we didn't care, we made it work - we just had to fuck! As it turned out Hilary's fucking was much like her cock-sucking skills. She would slowly raise herself until just the head of my cock remained inside before letting herself drop to the sound of her firm ass slapping my thighs.
The actress moaned and nuzzled her face into my shoulder where she began to suck and bite my neck, sending jolts of pleasure to course through my veins. My hands instinctively moved to her thick rump where I began to squeeze and knead her flesh, pulling her cheeks apart as she rode me in the passenger seat of her G-Wagon truck.
Her fucking became quicker and more feverish, abandoning her slow ride of earlier for a more frantic bucking. Finally with a loud gasp Hilary pulled herself completely off my cock and paused to catch her breath - her chest heaving against me.
"You're fucking amazing you know that." I snickered as I wiped the sweat from her brow.
"I need you back there." she breathed raggedly, before snatching my cock to position it between her ass cheeks.
"—wait, what?"
I barely had time to register what she was saying as she directed the head of my cock towards her ass. Unfortunately for us, Duff's initial attempt was unsuccessful and I heard her muttering to herself as she grabbed my cock again, this time lowering herself down while holding me in place.
"Holy-Shit." I groaned as I suddenly realized what was happening.
Not only was I having hot, spontaneous, car sex with Hilary Duff but now I was in the process of taking her backdoor?!
The insertion itself was painful for a moment, but then I felt a "pop" and her ass opened up and engulf my head. I slowly began feeding her my length, as she whimpered and moaned and fidgeted about. When I was finally embedded about halfway inside her poop-shute, Hilary began to grind her hips in slow tortuous motion, rising and falling, using her momentum and weight to slip me further inside.
"Fuck. Hilary."
"Ugh. Don't move." she whispered hotly above me. "—let me do all the work okay. Trust me. I know what I'm doing."
"Jesus. You're so tight." I gasped. "You're so fucking tight back there."
I wasn't kidding either. Her ass was so tight it was like fucking a closed fist.
"Yeah. You like it?" she moaned, slowly resuming her fucking. "You like being balls deep in my ass!"
"Fuck." was all I could muster as my hands gripped her hips and maintained our thrusts.
Her moans got louder and more punctuated as my thrusts picked up. Her nails dug into my shirt, gripping it like handles as she began taking me harder and deeper.
"Ugh-Fuck." she cussed erotically in my ear. "—don't stop now. Yes. Fuck my ass!"
All I could hear was the sound of her panting and the slap of her ass coming down on my legs as I fucked her shit-pipe. In fact our fucking got so fierce that I felt the entire car rocking from side to side but we couldn't care less - lost in our own little world.
"Yeah. Fuck my ass! Fuck it." she ranted.
I slapped her ass for good measure which set off another series of moans from her.
"Take it. Take that hard cock!" I hissed in her ear while wrapping my arms around her body and pounding up into her ass.
Suddenly that familiar tightness in my balls returned and I knew I couldn't last long.
"Hilary. I'm gunna come." I growled while gripping her ass-cheeks with both hands. "—do you hear me?"
This elicited another growl from her throat as she shut her eyes tight and slammed her ass down on me.
"Ahh. Do it!" she commanded. "—blow your load. Blow your fucking load inside me!"
Her thrusts intensified as I felt her sphincter tighten around my shaft, desperate to milk me dry.
"I'm gunna come." I chanted again. "You hear me. I'm gunna come in your ass!"
"—shoot that hot load inside me!" Duff pleaded before shoving her tongue down my throat.
Finally, unable to hold back any longer I exploded - my cock jerking intermittently as it filled her backdoor with spunk, her sphincter squeezing down around the base of the rod and draining thick ropes of cum into her bowels.
At that exact moment I felt her teeth sink into my neck as her moans grew to shrieks of ecstasy, before she twitched wildly and slumped forward atop of me in total hot mess.
We lay in this precarious position for some time before I finally spoke.
"Hilary—" I said with a face full of blonde hair draped across me. "Your call. What about your meeting?"
"huh...?" she muttered incoherently while still seeing stars.
"You still have to go and make your other meeting don't you?"
There was a long pause.
"Meh. Screw the meeting. I'm too tired." she said out of breath. "You drive."
"Drive?" I repeated. "—drive where."
"Drive me home. I need a shower."
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