Misadventures of the Duff Sisters 01

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Hilary and Haylie share an afternoon of lesbian fun.
1.5k words
4.56
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Part 1 of the 3 part series

Updated 01/21/2024
Created 07/21/2023
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The Misadventures of the Duff Sisters 1

(This is a stand-alone story, not a continuation of anything previous. It is the first in what will be a new series of stand-alone stories. Enjoy.)

"Hey! What's taking you so long?" shouted Hilary Duff from her bed. "We only have a few hours before Matthew and the kids get back from the movie."

From the adjoining bathroom her sister Haylie called back, "Be patient. They only left ten minutes ago. Besides, you aren't going anywhere." And then the older sibling giggled.

"That's really funny, sis" sighed Hilary, once again glancing up at the silk scarves which bound her wrists to the bedposts. The 36-year-old singer was totally naked, and her creamy pale skin looked even more porcelain against the deep plum comforter. An ultra plush pillow cradled her head, with another underneath her round, bulbous ass. She was curling and flexing her toes anxiously.

"Well, was I worth the wait?" Haylie stood in the doorway of the ensuite striking a seductive but playful pose. She was wearing a faded, oversized 'Lizzie McGuire' fan tee shirt with no bra, and her hair was tied back in a slightly boyish ponytail. Jutting out from under the hem of the shirt Hilary could see that her sister was wearing a rather large, strap on dildo. Apart from that, she was naked. While keeping her hands hidden behind her back, the brown-haired beauty crawled on her knees up onto the bed and slithered up between her sisters' open legs. "I have a surprise for you", she teased.

Hillary was smiling and squirming now, like a child anticipating Christmas. Her nipples were rock hard, and her clean-shaven pussy had been lubricated since waking up that morning. "What is it? Gimme gimmie gimme. I'll be a good girl, I promise. See?" Then she gestured towards her dripping girl-hole as best she could with a nod.

"Yes, I see" cooed the 38-year-old. Leaning down, Haylie took one of her sisters erect, pink nipples into her mouth and suckled. When she started nibbling, Hilary let out a soft moan and arched her back to better offer up her breasts for her siblings' affections. Then Haylie did the same to the other.

"My God, Hay. Are you going to fuck me, already? I can't take it. I've been horny and looking forward to this for hours." The former pop stars' juices were now trickling down between her meaty cheeks and a wet spot was beginning to spread. Her Labia were flushed, open and demanding attention.

From behind her Haylie brought forward a large, chrome, cone-shaped plug. It quite resembled a soft ice cream swirl and was about as big as a fist. Placing the tip against her younger sisters lips she instructed her to "Suck it. Get it nice and slippery." It wasn't possible for the blonde to fit the entire object into her mouth, so she also spit then licked her saliva around it's many swells and grooves.

"Put it in me, Hay. Here, take your pick. I need you to fuck me so bad. Do it!" Hilary was spreading her legs open as far as possible, holding her feet in the air and serving up both of her glistening openings for her sister's pleasure.

Working the tip between the curvy, former Disney stars slippery ass cheeks, Haylie popped it inside her wriggling sisters' rear entrance and slowly pushed. It slurped in one ridge at a time, until only the flat, jeweled base was left exposed. Hilary's rectum was now stretched and filled with the cool, metal plug. "How does that feel, sister dear?" the brown-haired actress asked, leaning forward and giving Hilary a long, deep and sloppy kiss.

"A-amazing. Please, I want to see and squeeze your tits now. Untie me. Untie me, please..." Hilary's desperation made Haylie smile as she casually raised the tee shirt over her head and tossed it aside. Her 34B breasts were plump, natural and perfect. They jiggled and swayed as she moved in on her knees and steered the tip of her strap on against her younger sibling's gooey girl-hole.

"Get ready, sexy" taunted Haylie, pressing her fleshy tits against either side of her sisters sweaty, hot cheeks, their erect nipples tickling the bound beauty's earlobes. "I'm going to tear that beautiful ass of yours up." With that, Haylie thrust her hips forward and began driving the dildos' 12-inch length up her juicy sex tunnel. The plug inside her anal passage made the journey a struggle, but the 38-year-old kept pushing until Hilary could feel it's head against her cervix. They were now clit to clit.

Wrapping her muscled, shapely legs around her sisters 28-inch waist, Hilary groaned and drew her incestuous lover in tight. "God, Hay. I'm so full. You're going to rip me apart but, I want you to. Fuck me. I can feel them rubbing against each other. Oh my God! FUCK ME!"

Haylie was pumping now, slowly, evenly and deeply. Hilary's face was contorted from a mix of pain and pleasure, her blonde hair damp from perspiration as she raised herself up to accept every thrust. "Are you going to cum for me, Hil? I want you to. Let go and cum for your big sister. Tell me how much better I fuck you than your husband."

"Harder, Hay. Fuck me harder. Matthew fucks like a girl compared to you. Give me your cock and make me cum. You're the best lay I've ever had. Fuck me. Yes. Yes. YES!!" It was then that Hilary Duff exploded in orgasm, her pussy grasping the silicon penis tightly as her nude body tossed and flailed. Her milky, 34-26-39 figure was wet and shimmering, and floods of her warm girl juice glazed her ass cheeks and the dildo still buried inside her.

After carefully pulling out her strap on, Haylie dipped her face down and began licking her sisters sopping, dripping pussy. Her clit was swollen and easy for the 38-year-old to locate, teasing it with her tongue while manipulating the plug still impaling her rear entrance. Hilary quickly came again, her exhausted, 5'2" frame shuddering quietly before collapsing into a pile of spent flesh.

Wiping the fluids from her chin, Haylie untied the scarves binding her siblings' wrists and gently placed Hilary's arms at her sides. Lying down next to her, she wrapped the younger woman's nude body in her arms and held her tightly against her own. Sleep took them both.

Haylie was having a wonderful dream. She was on a tropical beach wearing a very tiny bikini surrounded by handmaids delivering on her every need. Her husband and children were nowhere in sight, which made it even more perfect. Slowly the dream began to fade, and she was brought back to wakefulness by a tickling in her nether regions. Fluttering her brown eyes open, she looked down to see Hilary's face nestled between her legs enthusiastically eating her pussy. All that was visible of the blondes' face were her doe-eyes looking back up at Haylie over the older woman's well-trimmed bush as she licked, sucked and slurped.

She must have been doing it for quite a while as Haylie could tell her cunt was hot and flooded with juice. "Ooh. That's nice, Hil. I wish I could wake up to that every morning. Yeah, right there. You know just what to do to me. Mm. Nn. Oh, yes. You're gonna make me cum, sis. You're gonna make me cum, sis. YOU'RE GONNA MAKE ME CUM!" As the warm fluid gushed freely out of Haylie's sex-tunnel, the older Duff clasped her hands around her sisters' head and pulled her mouth into her gooey slit. Hilary darted her tongue inside the slippery hole like an eel burrowing into its hiding place. The brown-haired sister had three orgasms, one after the other.

As the sisters sat facing each other, admiring each other's bodies while playing with their tits, a chime sounded on Hilary's' phone. After giving each of Haylie's soft breasts a playful squeeze, the former pop star crawled to the nightstand and studied the screen. "They're at the gate. Matthew and the kids. Guess we'd better get dressed."

While both women struggled to find their respective clothes, Haylie laughed and said to her sister "I think you're forgetting something."

Slipping a flowy sundress over her head, Hilary looked at her older sister quizzically. "What?"

Even though she looked great in tight jeans, Haylie was struggling to get them up over the swells of her hips. "The plug. You still have the plug in your beautiful, perfect ass."

"Oh, yeah. Right. Well, I'm not going to let him anywhere near there tonight, so I think I'll just leave it and think about who put it there."

Once again wearing her Lizzie McGuire shirt and jeans, Haylie wrapped her arms around her sisters' waist and lovingly cupped her bountiful ass-flesh in her hands. "You mean me?"

Kissing her deeply, her tongue and lips still seasoned with the taste of Haylies' pussy, Hilary responded, "Always. It's only you."

The End

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