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Thread: "Happy Trails" with Hilary Duff

  1. #1
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    TPG is offline Women are meant to be loved, not understood
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    Jun 2006
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    fanfiction "Happy Trails" with Hilary Duff

    Happy Trails
    With Hilary Duff
    Written by TPG (inspired by a dream)
    CODES: MF, gloryhole, ass play, blowjob, deep-throat, creampie, mutual mast
    DISCLAIMER: This FICTIONAL story was written for entertainment purposes only
    A/N: Had a dream this morning, decided to punch it up

    For as long as I can remember I'd always been obsessed with Hilary Duff, at least for as long as we'd been next door neighbors. Of course I never expected anything to happen between us, since she was in her early 30's, while I was in my late teens. However, this didn't stop her from openly flirting with me on a daily basis, and flashing as much skin around the house as possible. This was particularly true whenever she'd run to the store or do a few errands, and have me house-sit for her. Suffice to say I happily did this for free as seeing her bend over and flash me that magnificent rack of hers was reward enough.

    I can't even count the amount of times I'd seen her in a bikini over the years, or catch her wandering around her yard in the middle of the night completely naked, as she frequently enjoyed skinny dipping under the moonlight. This one particular afternoon I was watching her from my bedroom window as she lay out by the pool, and judging from the way she was giggling I suspect she was on her phone playing around on Tinder. In fact in recent weeks she didn't even hide the fact that she was using the dating app, and hooking up with complete strangers in the neighborhood. While most of my friends frowned upon this and considered it seedy, the notion that someone of her caliber was attainable actually turned me on.

    Naturally, I busied myself with Fortnite and kept an eye on her all morning until, I finally watched her go inside to get changed, before sneaking out the back gate of her property which lead out to a hiking trail. I found this strange since I liked to think I knew her well enough to know her daily routine, and knew Hilary would often workout early in the morning and then spend the rest of the day tanning by the pool. However that day she appeared to go to all the trouble of greasing herself up in suntan lotion, only to then change into her yoga pants and go for a run? The whole thing seemed suspicious to me, so I decided to grab my phone and follow her.

    Even though I knew it was wrong, I still convinced myself that I was doing her a favor and making sure she was safe. That and the fact, I also hoped that maybe I'd catch her meeting up with one of her Tinder dates, as I always wanted to see what kind of guys she was attracted to. That said, I kept my distance and watched as she hiked for about 10mins and finally stopped at a nearby lookout, which featured a park bench and a public restroom.

    When I realized this was nothing more than a late afternoon hike, I almost turned around and went home but instead decided to give it a few more minutes, and then watched her disappear into the restroom. I debated briefly about following her, but of course my excitement won out and I tentatively stepped into the deserted restroom only to find that Duff had locked herself in one of the stalls. My heart raced as I quickly duck into the very next stall, praying to god I wouldn't be found out – knowing how pissed Hilary would be if she knew that I had spied and followed her out there. However, whatever misgivings I might have had soon dissipated when I began to hear soft moans and whimpers emanating from the adjacent stall.

    Without thinking, I took out my cock and began to jack off as I listened to Hilary fumble with her clothes and apparently get off right there in the next stall. In fact her panting was soon accompanied by the sound of a very lewd, wet pussy which she was clearly rubbing and probing with her fingers. It was just about hottest thing I'd ever heard.

    "fuck.. I'm so wet right now." I heard her whimper, as she audibly masturbated.

    Just hearing this tone from her caused pre-cum to leak from the tip of my cock, causing my own fapping to increase. In fact, I was so caught up in my own pleasure, that to my dismay Hilary could hear me beating off beside her, but instead of being surprised or angered by this, she seemed aroused and encouraged it.

    "ah yeah.. stroke that cock for me." she whispered hotly.

    As far as I knew, Duff still had no idea who I was and just assumed I was either a guy she had contacted via Tinder, or a complete random she could mutual masturbate with, anonymously. Either way I was happy to oblige and help her get off. However, I was soon floored when Duff decided to take things to the next level, and I noticed her finger suddenly appear through a small hole in the wall between us. In all the commotion I didn't even notice it before, and I began to panic and wonder if she could see me. Then again, logic dictated that if she had known it was me she would have stormed out already.

    My mind began to reel as I weight up my options. On the one hand I knew it would be crossing the line, but then again I also knew that if I didn't take this opportunity I'd never forgive myself for the rest of my life. I also began to wonder just how many times she had done this before, and the more I thought about it the more it turned me on - Hilary Duff likes to suck dicks via a gloryhole? Amusingly enough the more I hesitate the more persistent she was, with her pleading for me to slide my cock through the hole.

    "Why don't you let me take care of that for you?" I heard her offer.

    Despite my better judgment, I did as she asked and carefully slipped my teenage cock through the hole, only to feel her immediately wrap her warm lips around it. I could barely believe my luck as Hilary then proceeded to not just blow me, but worship my cock – sucking, licking, and slurping loudly on the head, before dragging her tongue up and down my vein-lain organ.

    In all my years I'd never experienced such an exquisite blowjob. I would tell she had done this before, and was a god damn expert at it. God only knows how many times she had ducked into that very same stall to give countless hikers the same treatment. The idea alone almost made me pop. As expected, I couldn't last very long and grunted as I approached my climax, only to feel her wrap her lips around the head of my cock and invite me to nut inside her mouth.

    "give it to me..." she purred. "give me that hot load!"

    I came so hard I almost blacked out, as I felt her moan around my spurting rod and gulp down every last drop. However, before I even had time to pull up my pants we heard a group of fellow hikers loiter just outside the restroom, and prayed they wouldn't come in. This caused us both to panic and attempt to leave, and while I rushed to pull up my pants, I leered out of the door to see if the coast was clear, only to exchange eye contact with Hilary in the mirror!


    "Err, um... I can explain!"

    Fortunately for me Hilary's temper was interrupted by the hikers who then entered the restroom, causing Duff to rush into my stall to hide, before shutting the door and locking us in together. I'd never been more embarrassed in all my life, as we heard the girls laugh and chat loudly on the other side of the door.

    "You're in so much trouble when we get home," Hilary said. "I can't believe you'd do something as low as this."

    "Low? I just..."

    "Save it," she cut me off, before she was forced to reach over to place her hand over my mouth.

    I don't mind admitting that the entire incident really turned me on, particularly as I suddenly realized that I could smell her pussy juice on her fingers.

    "I can't believe you followed me up here," she hissed as she listened at the door.

    I don't know why but her attitude really pissed me off. I mean I'm not sure what I expected her to say, but considering she had just BLOWN me and swallowed my wad, I guess I kind of expected her to be a little grateful, or in the very least pleased? So with nothing to lose, I decided to just throw caution to the wind and reached up to cup one of her breasts. To my amusement, Duff didn't respond. In fact she just stood there and rolled her eyes and smirked to herself as I fondled her. I took this as permission, as she didn't seem to care either way. In fact I dare say she kind of liked it, if those hard nipples were anything to go by.

    "You spoiled little shit," she whispered. "You're going to get us both in trouble."

    I responded by plunging my hand into her yoga pants – stretching them out and almost ripping the seams - to make direct contact with her incredibly soft, bare butt. I noticed two things almost immediately... 1) her booty seemed to soft and warm to the touch, and 2) that she didn't appear to be wearing ANY panties whatsoever. She moaned softly to this action, but then freaked out and squirmed as my other hand plunged down the front of her pants towards her sex. At this point I was as hard as a rock, as all my fantasies were coming true and I was permitted to touch her just how I had always imagined I would.

    "Stop it, we can't." she hesitated. "What if they hear us?"

    However, when my hand slipped further inside and finally came in contact with her dripping wet sex, Hilary immediately reached down to grab hold of the cock, gripping it firmly in her hand.

    "ugh.. you're gonna get us caught!" she whined just inches from my face.

    God how I wanted to kiss her.

    Instead, I ignored her words and skimmed the very tips of my fingers along her hot, slick cunt-lips, causing her to coo into my mouth. Despite her dithering, I could tell she was getting off on the danger of it all, and moreover impressed with the size of my package considering she not only refused to let go, but was now actively stroking it.

    "you're wet," I whispered back at her. "your so fucking wet."

    To emphasize the point, I effortlessly plunged two of my fingers knuckle-deep into her pussy, causing her groan and open her stance for me. Hilary now stood there with her eyes shut and her mouth open, moaning softly while I finger-banged her in the small stall. It was without doubt the single best moment of my life, and something I'll remember for the rest of my days. I continued to probe and finger her for several moments before she took my breath away, and leaned in close.

    "Don't make a sound," she said before she fished out my cock and fell to her knees.

    I barely had time to process what was about to happen, much less think of anything witty to say, before Hilary engulfed the head of my rod with her warm mouth and proceeded to blow me while gripping the base of my shaft. In fact she almost moaned audibly and clearly relished the feel of a hard young cock in her mouth. I watched as she swiveled her head from side to side while she polished me, while I reached down and ran my hands through her blonde hair. This swivel-action was soon replaced with her bobbing her head back and forth, while still trying our best to stay quiet.

    I then took her direction and quietly sat back down on the toilet, and spread my legs for her, as she instructed me to raise my knees up in the air. I almost gave us away and moaned out loud myself, when she dragged her tongue down to my nuts!! This incredible display went on for several minutes, while I had to use every ounce of strength I had not to cum. She then got up from the floor and indicated with her finger to stay quiet, and peeled off her pants and proceeded to straddle me. I watched dumbfounded, as she carefully sank herself down onto my sword, and took me all the way in, in one smooth motion. The sensation was so intense, we dare not move for a few seconds knowing we'll both moan out loud. She felt like a tight warm glove. We were both so aroused, we could feel the other tensing and throbbing inside.

    Thinking quickly, I pulled her down into a deep kiss and the moment our tongues met and swirled around each other, I suddenly exploded inside her. We both grunted to the action, and twitched as we felt my cock spasm and blast several ropes of spunk deep inside her. All the while the other hikers continued laughing and ranting as they finally left. Hilary and I stayed locked in that position – having just creampied her - making out furiously as my twitching cock remained rock solid. All things considered, I probably should have been more surprised than she was by this, but the fact that I was still rock hard seemed to drive her crazy.

    "Ah shit... you're still hard! you're still hard for me." she moaned between kisses, and proceeded to move her hips.

    The moment we heard the others leave the restroom, Hilary proceeded to whip her hips back and forth and rode me more intensely, milking my cock and causing the existing ejaculate to seep out of her cunt. Having just blown my load (for the second time in as many minutes) my balls hurt with every movement she made above me, but I just couldn't make myself stop her. The sensation was both painful and exquisite as she rode me harder and faster on that toilet, the sound of skin slapping against skin echoing throughout the tiled room.

    "Think you can cum again, huh?" she urged as she slammed her plump ass down on me again and again.

    I pulled her into another deep kiss, which caused me to throb inside her. Noting this Hilary groaned and shoved her tongue down my throat, and stopped briefly to drool her spit into my mouth. All the while she continued to slam her ass down on me, taking me balls deep until she gasped and came - tensing up and shaking violently above me. Having had her fill, Duff shoved her tongue down my throat.

    "You're going to get me into so much trouble," she said.

    We ended up leaving the restroom a few minutes later, with her instructing me to give her a few minutes head start in case someone sees us together. I followed her instructions and used her back gate to get into my own yard. However, just as I passed her pool I could see Hilary was standing by the side door, waving me over. I assume she wanted to remind me not to tell anyone about our little liaison. However the moment I approached her at the door, Hilary pulled me into the laundry room, pinned me up against the wall and kissed me again.

    In an instant my hands were at her ass, groping and squeezing her again. She then followed this up by dropping to her knees and hungrily wrapped those sweet warm lips back around my cock again. This time however it was a totally different experience – way more thrilling - as we were doing it in her house and just a few feet away from home. Duff also seemed to put extra effort into getting me off, and seemed keen to make me cum as quickly as possible. I ran my fingers through her blonde hair, only to see her glaring up and keeping constant eye contact with me.

    Feeling emboldened, I proceeded to fuck her drooling mouth with deep long thrusts, my balls striking her chin. She grunted erotically to this as she was forced to take me into the back of her throat. Fucking her mouth in this way (roughly) really seemed to turn her on and it didn't take long for me to nut once again, only this time instead of letting her swallow it, I pulled out and shot ropes of spunk across her pretty face, completely coating her in jizz.

    "You better get out of here before someone sees you here." was her only response.

    When I got home a few moments later, my folks stopped me in the kitchen.

    "By the way, next door (Hilary) wants to know if you're available to house sit for her tomorrow night, should we tell her you're busy?"

    "Nah, I'll do it." I shrugged. "Might as well, I got nothing better to do."

    "Don't worry son," dad chimed in. "I'm sure she'll repay you one of these days for all the hard work you put it."

    "Yeah, maybe." I grinned, before running up to my room.

  2. #2
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    Nov 2011
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    It's been far to long since a Hilary Duff story was posted on here.

    Thanks for sharing this, TPG.
    Recently Completed Stories
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  4. #3
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    Jan 2019
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    Great story, love reading about Hilary Duff. Glad to see she is still getting some love.

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