Hillary Duff / Lizzie McGuire - Italian Interlude

BY : Tricky_Dick
Category: Celebrities - Misc > Threesomes/Moresomes
Dragon prints: 1509
Disclaimer: This is a work of FICTION. I do not know Hillary Duff or have anything to do with her. I make no money from this story.

A few glasses of wine and they made out….. Gio convinced Hilary to stay over…. It’s late.

The next day it was a tour of the grounds and food…. And they kissed a lot….. It got pretty heavy… but Gio kept it under control.

Later that night they had a wonderful dinner and after he convinced her to go swimming in their pool…. There is an extra suit for her to wear.  They kissed more and after some groping…. He took off his suit and teased Hilary  into going skinny dipping with him.  They felt each other up and then Gio led her off to bed.

Hilary was excited to be with this tall, dark and handsome young man.  He was what romance novels look like and she wasn’t a virgin so she decided to sleep with him.

Gio led her into a large bedroom.  They were already naked so he turned her and kissed her passionately.  Hilary’s nipples were hard thinking of what is about to happen.  As they kissed he let his hands roam all over her soft skin…. Grazing her nipples and lightly pinching them.  He stroked her pussy lips as she sighed…. And then he laid her down on the bed.


Hilary watched as he kissed her feet and sucked on her toes…. Also a new thing… She giggled and squealed a bit as he teased her feet.  Gio gazed into her eyes as he gently opened her thighs.  The lights were on and she had never had sex like this…. She’d only had sex with the lights off and under the covers.  Hilary watched as he kissed and nibbled on the inside of her thighs…. Little licks and sucks as he moved closer and closer to her tender treasure.  Her eyes widened as he looked up at her just before he slipped his tongue inside her.  “MMMMMMMUUUUGGHH”, she moaned.  Hilary was really turned on by this whole experience.  Gio’s tongue found a home and Hilary’s hands went to his head as he painted her teenage slit.  “AHHHHH… she groaned as he slipped his fingers inside her.  Hilary let go and threw her arms and head back as Gio fingered her.  Two and then three fingers wormed around inside her…. He pumped them until she started to buck her hips…. “OOHHH…… OHHHH….. UUUUMMM….” She cooed as Gio added forceful licks to her swollen clit.  Hilary was on the verge of cumming…. She gripped his head again and looked down at him.  Their eyes met as she came…. Gio watched her eyelids flutter along with her cunt…. He hungrily lapped up her juices and then turned his head to his friends hiding in the closet and winked at them.  The two friends had watched them skinny dipping and hid in the bedroom with a video camera to capture the whole seduction.  Hilary was writhing blissfully and didn’t notice.  She was about to get MUCH MORE than she bargained for.


Gio moved up between her legs and kissed the teenage starlet…. Before she could ask about protection Gio pushed the head of his cock inside her.  Hilary immediately thought about the dangers but she was a little drunk…. Very turned on…. And with Gio’s tongue in her mouth she just decided that she was going to “risk it.”  Hilary broke the kiss…. “Don’t cum inside me.” She said.  Gio nodded as he bottomed out inside his lover.   He supported her legs and pulled out and thrust into his prize.  “UUUUUUUHHHHMMM” she moaned and Gio watched her as he began to pump the teen queen.  Hilary was on fire.  She hadn’t had sex without a condom so it felt very different.  Gio’s cock wasn’t huge but it felt really good inside her…. Something about having this tryst had her whole body on fire…. She was going to cum again very soon.  Gio was careful…. He didn’t want to cum too soon…. But still he pumped her tight pussy forcefully…. He wanted to please her…. And he was showing off for his friends.  “UGH…. HUUGH….. HMMMM…. UGHHH…. OHH….. OHHH….. GIO!..... MMMMHHHMMMM…..” she moaned.  Hilary wrapped her legs around the young man as he fucked her well….. She clutched his head to her as her orgasm crested.  “AAAHHHHHOOOOHHHHHHGGGAWWWDD”, she cried…..   Gio was there…. He had to pull out. 

Gio knew what he wanted…. So he immediately moved over Hilary’s body until he was straddling her chest.  He put his cock between her breasts and began to rub his cock against them.  Hilary watched until he tugged her head up enough so the tip was close…. She knew…. But she was nervous.  Hilary had never swallowed and she certainly didn’t want him to cum on her face…. But then Gio took charge.  He pushed forward and thrust his cock into her mouth.  Hilary took it…. She was enjoying his aggressiveness.  It turned her on that he wasn’t asking…. He was so masculine and “in charge”.  He didn’t force it down her throat…. Just enough so she could suck it and he could cum.  Hilary was enjoying this…. She accepted that he would cum in her mouth.  She could taste his pre-cum…. He tasted good…. This was going to happen.

Gio had her right where he wanted her.  Hilary was completely enamored with him…. And preoccupied with sucking his bursting cock.  He was ready to cum but holding back just a little longer…. Until the trap was closed.  He motioned to the guys in the closet and they both crept out.  One held the camera as the other friend moved onto the bed.  This friend Paolo quickly approached Hilary’s dripping love box without touching her.  He had to be fast with his attack or she might resist. 

On the signal Gio gripped Hilary’s head and began to moan his approval to let her know he was close….  Paolo opened her thighs a bit more and put his mouth right onto her pussy pushing his tongue inside the starlet.  Hilary’s eyes flew open but Gio’s eyes were closed on purpose.  He thrust passionately holding her head tight as Paolo licked and sucked on her clit.  Paolo pushed three fingers inside her and pumped them quickly to overwhelm the teen.  Hilary squealed a bit but Gio pretended to be oblivious as he was about to cum…. Hilary’s hips were unconsciously thrusting to meet the fingers.  She moaned around the throbbing cock in her mouth.  Paolo was winning….. Hilary started to tremble…. He was going to make her cum.  Her thighs gripped him….. she began to buck….. Gio came loudly, pumping streams of hot cum into her hungry mouth…. It was all too much….. Hilary came in Paolo’s mouth as his fingers continued to work in and out of her clutching channel.  Her head was spinning….. she swallowed the burning fluid with a sigh.

Paolo quickly positioned himself before Gio moved and He urgently entered the hot teen’s willing pussy.  “MMMMMMMHHHHHHHMMMMMMMM” she groaned around the shrinking cock in her mouth.  Hilary’s eyes closed as Paolo began to pump her tight cunt.  Gio climbed off and Paolo immediately leaned in and kissed.  “You’re amazing!”, he whispered in her ear as he fervently rocked his hard cock into their conquest.  Hilary was shocked by all of this but the cock had her under its spell….  She was so fired up she just gave in and let Paolo fuck her.  “UUHHH…. MMMMHHHHAAAHHHH….. OOOHHHH…. UHHHHH….. GAAAHHHH ……  GOD…..  …. OH GOD…. OH GOD…. OH GAAAAAWWWDDDDD!”, she cried out as she came again.  Hilary had succumbed to the immense pleasure she was getting, coupled with the daring conquest performed on her by the young men.  She squealed gleefully as Paolo continued to fuck her tight teen cunt.  She’s never had crazy sex like this and there was no turning back now.  Her juicy pussy was blissfully tightening and she was going to cum even harder now….. 

Gio kissed her as the last friend set the camera just out of sight so he could join in.  Gio whispered into her ear as she was cresting again.  “You’re the most beautiful girl in the world”, he purred into her ear as Paolo banged away at her treasure…. Hilary bucked and moaned as Paolo sent her over the edge again.  “AAAAHHHH…. HHAAHAAAA…. OOOOHHHHHH MMMYYYY GAAAWWWDDDDD!” she moaned. 

Now for the final member to join.  Gio offered his cock to their panting prize…. Hilary hungrily took it.  Gio’s cock throbbed back to life and she smiled on it as he began to pump.  Then on cue Paolo rolled Hilary over and started to fuck her doggie style as Gio fucked her mouth.  In this position Gio and Paolo changed places….. Hilary sighed as Paolo filled her mouth with his fiery rocket.  Gio rocked right back into her clutching cunt…. Hilary groaned as the two set up a rhythm.  Paolo enjoyed playing with their little sex toy…. He was excited about what was to “cum”….. and the video they had to document them fucking this Disney star. 

Finally it was time.  Gio pulled out and Antonio buried his tongue in Hilary’s pussy.  “MMMMMMMMMMMMM” she moaned around Paolo’s cock.  Gio moved off and took up the camera to get close ups of Tony sucking Hilary’s pussy.  He slipped his fingers into the babe and finger fucked her until she was cumming again.  He smiled at the camera as he lapped up her juices.  The final capitulation was at hand….. Tony entered Hilary’s tight teen pussy.  His cock was bigger than the others…. Hilary groaned and pulled off Paolo’s cock.  She looked back and saw Antonio.  She knew even before she looked because the trio had been together before so she had a feeling when she felt this new hard cock….. and while this was another lover and that freaked her out….. it was also very exciting…. She was having sex with THREE HANDSOME MEN!!!  What a crazy story this would be, if she ever told anyone.  Tony looked her in the eye and spanked her ass…… then started banging away at her delicious dessert.  “UUHH UHH UHH UHH UHH HHHUHH…. MMM…. AHHH… AHHH… OOOHHH OOHHH OHHHH…. OHMMMMMMMM” Hilary yelped as Tony fucked her deep until Gio pushed his cock back into her mouth.  Then as Tony banged the sweet angel Gio and Paolo switched off fucking her face.

Tony rolled Hilary over and put her ankles on his shoulders.  She looked up at him with nervous anticipation as he reentered her….. Tony started to pound away at her pussy.  For a short time he had her complete attention as he compressed her body and fucked her hard….. Hilary came violently, clawing at him and begging for more.  “YES…. YEAHH… YEAAAHHHSSS….. GOD…. YEAHHASSS….. TON…… NY…. FUCK ME…….. FUCK….. ME….. GOD …. OH GOD… OH YEASSS….. YEAHSS.S….. PLEASEESS…..  GODDD….. GAWWWWDDDDAADAAHAHHHHHHH!”

Tony pulled out and the trio helped her to her knees on the floor.  Hilary wasn’t expecting this but it excited her.  They all wanted her to suck their cocks.  Again…. They just did it…. They didn’t ask….. They just moved her and Gio pushed his cock into her mouth.  As each man took his turn fucking her mouth, Hilary thought…. “At least I can’t get pregnant like this.”  Little did she know that the camera was pointed right at her face and this final “money shot” was framed perfectly as she serviced the trio.

Hilary was wildly excited and she enthusiastically sucked each guy trying to make him cum.  The guys savored this beauty queen’s transformation into slut.  They made sure the camera could see her and they each fucked her mouth until they were all right there.  Hilary “thought” that she was expected to swallow them all, but that wasn’t the case…. Since they stroked their cocks between sucking she wasn’t prepared when they all jerked it right at her face.  Antonio grabbed the back of her head and Hilary’s eyes went wide when she realized what they were about to do….   and then just like a porno, one after the other they erupted, spraying gobs of hot cum onto her face.  She was going to turn away but Antonio held her fast and she squealed as her face was covered in hot sticky cum….. The guys then pushed their dripping cocks into her mouth to be sucked until she had cleaned off all three.  The guys rubbed their cocks across her cheeks and lips as they smeared the cum all over her…. Hilary sucked and sucked on each cock until she was just done…. Totally exhausted the guys lifted her to the bed and laid her down.  In minutes Hilary was out and slept the rest of the night.

The guys couldn’t wait to watch the video.  They cued it up on the big screen and sat watching it and complimenting each other’s performance.  “We just fucked Hilary Duff!”, they chimed.  “Who?”, a man’s voice came from behind.  The guys jumped up and turned around…. “Papa….. um…. I have a guest.” Gio replied… startled but still proud of his achievement.  “She’s beautiful…. Is she famous or something?” he continued.  “Yeah… Yes…” they all replied…. “She’s a Disney movie star.” Gio replied.  “Very good…. Well why don’t you boys get to sleep… it’s late.” He suggested.  Gio shut off the TV and they all went off to the different rooms….. The trio had crashed at Gio’s house before so they had a system.  Gio’s father looked in on Gio’s room as he was entering and he could see the sleeping teen still naked.  “How long is she staying?” he asked.  “I don’t know.” Gio replied.  “She’s rich and famous so she doesn’t have to leave until she wants to…. I guess.”  “Does she know about the movie you made or is this like the other girls?”, the father asked.  Gio just smiled…. The father smiled back and shook his head.  “Get to bed…. And let her sleep.”

The next morning the father was up early and made coffee.  He heard a noise and went for a look.  Gio was asleep in his bed and the girl was up….. he could hear the shower….. he licked his lips thinking of her naked body all wet and inviting.  He went to the door and opened it…. Hillary didn’t notice.  She was enjoying the soothing wash of hot water.  The father quickly stripped off his robe and shorts and eased in behind her.  He tucked his head close to hers so she’d have to fully turn around to realize it wasn’t Gio.  Then he started to rub her shoulders.  “Mmmmmm…… That feels wonderful.”, she purred.  The father then reached around and caressed the delightful teen.  “Mmmmmmmm…..”, she sighed as he began to stroke her tits and squeeze her nipples.  He sucked on her earlobe as his hands roamed her silky body until he found her treasure.  “OOOHhhhhhh”, she groaned.  The father had her…..  his expert fingers worked their magic on her clit as it swelled in response.  The father continued to kiss, nibble and suck on her ears and neck as he fingered her.  He dipped his finger into her tight pussy.  “Aaahhhh.”, she moaned.  He coated her clit with her juice and stroked it with a purpose.  Hilary began to buck….. “UGH…… UGH…. GAAAAHHH….. OHHHH….OOHHH…. OOOHHHHHH”, she cried as she came on his hand.  The father smeared her juice all over his hand and then rubbed it over his big hard cock…  Yep it was bigger than Gio’s and Hilary was about to find out for herself.

The father pushed her towards the wall and Hilary braced herself as she felt the head rub against her tender slit.  “MMMOOOOHHHHH!”, she groaned as the tip was pressed in.  Hilary felt something but it didn’t register until the father pushed more of it into her hot teen cunt.  “AHHHHHHHH GAWD!!!”, Hilary moaned.  Finally, she turned her head back and saw the adult man behind her.  He gripped her hips and finished the push into her velvet vice.  “UUUUUGGGGGHHHHHHHH”, she grunted as he buried his tool.  “Oh Gawd….. who are you?!”, she shot at him…. Even while falling under his spell.  The man began to thrust into the teen and she could not resist the power of his thick, long tool.  “MMMMAAAAAHHH”…. She cried.  The father pulled her body back up against his….. He grabbed a breast as his fingers found her clit.  Once again his expertise was too much for her.  He fucked her tight cunt, fingered her clit and pinched her nipples as he whispered into her ear.  “My name is Ricardo….. I’m Gio’s papa.  I see you like my cock don’t you principessa…..”  “UHHHHHHHHMMMMMMM”, she sighed in response.  Hilary was beside herself…. She was being fucked by the FATHER of the guy who fucked her last night….. It was beyond surreal…. But every thrust was like glorious electric shocks.  Ricardo fucked her harder as he watched the teen surrender….. She was just like the other girls…. Easy to please and unable to resist his big cock.  It was the biggest Hilary had ever had…. It stretched her tight tunnel and he didn’t even have to try hard to get her off….. Her teen pussy was about to tilt….. She felt it….. He felt it….. It started to flutter and Hilary gripped whatever she could hold onto as her pussy exploded.  “AHH AHH AHHH AHHH UGGHH…. MHHHH…… SIRR….. OH….. SIR…. OH GAWDD…. OH….. UHHH…. UHHH….. AHHH…. HHAAAA…. OHHHHH PUULLLEEEASSEEE DOONNTT STOPPPP……. YESSSS…. YESSS….. YEESUUUUUUSSSSSSSS….. UHHHHHHHHHHHHHHHHH!!!!”

Ricardo turned the teen around and kissed her.  Hilary was infatuated with this handsome older man.  As he kissed her, he lifted her leg and bent down to enter her tender pussy.  “UUUUGGGGHHHHHH GAWD!” she moaned into his shoulder.  He lifted her off the ground and she wrapped her legs around him.  Ricardo then banged the Disney star against the wall hard!  She was beyond orgasmic….. This time her cunt latched onto his rocket and just kept fluttering again and again….  It was blissful.  Ricardo kissed the teen sensation as she came again and again until he couldn’t last anymore.  He pulled out of her tight pussy and set her down.  “Now principessa….. suck me now.” He moaned.  Hilary was actually excited about swallowing his cum.  She finally got a look at this huge cock….. Her eyes were wide when she saw it up close…. But she couldn’t wait to get on it.  The hot teenager stuffed as much into her mouth as she could!  She moved her head quickly sucking and rubbing her tongue on the sensitive underside.  Ricardo stroked her cheeks and held her head as he fucked her face.  Hilary moaned and groaned as his sticky juice oozed out…… Then she felt his balls clutch as he legs trembled and he exploded blasts of hot cream into her mouth.  “MMMMMPPPHHHH…. MMMHHHHMMMMM…… MMMMMHHHHMMMM”, she purred as he emptied his load. 


Ricardo lifted the starlet to her feet and turned off the water.  He helped her out of the shower and started to dry her off.  “You are amazing….. and so beautiful.” He praised.  “I can’t believe I just has sex with my boyfriend’s dad.” She quipped.  “Boyfriend?”, he replied.  “Well…. I guess technically …..” she started.  “What about the other boys?” he asked.  “He told you!!??” she exclaimed.  “I saw the video.” He replied with a knowing smirk.  “WHAT VIDEO???  OH MY GOD…. THEY FILMED ME!” she spat….  “Relax principessa…. You’re not the first and you won’t be the last.”, he replied.  “You don’t understand….. a video like that will ruin my career.” She cried.  “Yes….. he said you’re a Disney star?” he asked.  “YES….. and if that video gets out my career is over…. Oh my GOD….. where is it….. give it to me.” She begged.  “Principessa…. Don’t worry.  I won’t let him keep it…. Just relax.  I’m going to take care of you.” He offered.  Hilary was almost in tears and he brushed her hair back and kissed her again.  “Come with me.” He ordered.  Hilary followed with a towel around her.

They went out into the living room and he located the TV and the video camera attached to it.  He unplugged it and led Hilary to the master suite.  He plugged the camera into the TV and started up the video.  “HOLY SHIT!” she exclaimed….. “You can see everything…. I can’t believe they did that to me.” She cried.  “Principessa…… it means they love you… so much that they all make love to you.  You look like you’re very happy here…. Yes?” he posed…..   “Yeah but….” She started.  “And you cum many times?” he continued.  “Well….. um…. Yes….” She continued.  “And the only worry is other people will see the video?” he asked.  “YES!..... It will ruin me….. I’m not a porn star….. it looks like a porno movie.” She lamented.  “Yes…. Yes it does.” He replied as he squeezed her ass.  Hilary leaned into him as she felt some of her shock dissipate.  “Principessa…… You have my word that this video will never leave this house.” He promised.  Hilary looked up at him with pleading eyes….. “Can’t we just erase it?” she begged.  “Don’t you want to make a movie with me?” he countered with a smile.  Hilary’s eyes widened at his proposal….. “Um…. I …. I…..”, she stammered.  He kissed her again….. “Should I hide the camera?” he offered with a laugh.  Hilary couldn’t help it…… she smiled and realized that maybe she was overreacting.

He reached over and pulled off her towel.  Then he lifted her up and tossed her on the bed….. He turned on the video and crawled up to her.  He gave her some kisses and propped her up with a pillow.  Hilary watched herself getting her pussy licked, and like the video Ricardo slid down between her sexy thighs and buried his tongue inside her.  “OOOHHHHHHHH YEEEESSSSSHH” she moaned deeply enjoying his touch.

Now Ricardo expertly tongued and fingered her teen pussy as she watched her own porn…… Soon he was hard again and he mounted his tender conquest.  Hilary was completely taken by this man.  She blissfully sighed as he plunged back inside her juicy teen cunt.  Hilary wrapped her legs around him and held on.  Ricardo fucked her slow and easy knowing that every thrust was the best sex she’d ever had.  He could feel her cunt trembling and clutching at him over and over again…… Her head rocked from side to side as he pumped her delightful pussy.  Hilary was his prize…. He had completely won her over…. So much so that as he approached his own orgasm she wanted him to cum inside her…. But Ricardo didn’t want to risk it so Hilary sucked him off again swallowing another hot load.  Then she slipped off to sleep.

Over the next week Ricardo, his son and his friends had their way with Hilary….. she just let them do as they please with her….. They even made more videos.  Something about Ricardo’s promise…. She just trusted that her videos would never see the light of day.  She was infatuated with Gio and his friends but she secretly LOVED his dad…..  So much so that Ricardo flew back to the states with her so she could join the Mile High Club.  This would definitely not be the last time she visited Italy.

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