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gurugirl · 3 months

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Dress up

sugardaddy!harry x yn | An extra for The Arrangement

Summary: Y/n dresses up in diamonds and jewels and thinks she looks sexy so she secretly makes a solo video of herself. But then she goes out on a limb and sends the video to Harry while he's working.

A/N: Sorry it's been so long since I've given you an update for these two! This was requested! Here

Word Count: 4,548

Warning: 18+ only, smut, use of toys, spanking, sharing of a solo sex tape

The Arrangement Masterlist

. .

Y/n remembers a time when she’d wear clothes that were slightly unkempt. Clean but perhaps maybe a little wrinkled. Shirt hems and collars would be folded funny, buttons misaligned, sweaters and dresses not fitted properly…

Back then she relied on the drier to de-wrinkle her clothes. Nowadays a professional service delivered her freshly cleaned and pressed items to her door. All of which were tailored to fit her perfectly.

So it wasn’t unusual for Y/n to play dress up with herself when Harry was away at the office and she was at home alone. She enjoyed having such nice clothes and things filling her closet. It’s something she never had before.

She’d layer on a silk Chanel dress with her Ferragamo belt, a Hermes scarf, and the expensive custom disk hat with silk roses Harry bought her when they went to the Kentucky Derby. She’d watch herself in the long floor-length mirror and practice walking like a woman who owned the kind of clothes she was wearing.

But sometimes she focused on the jewelry. The pretty shiny rocks and jewels, delicately woven precious metal bands and chains… Harry had bought her more jewelry than she’d ever seen in her life. Diamonds, gold, platinum, rubies, emeralds, pearls, silver… Rings, watches, brooches, necklaces, anklets, earrings, belts, and bracelets. You name it.

And on this particular evening, Harry was at a dinner meeting that was going to run late. She’d bathed and put on her perfumed moisturizing balm and then walked naked into her massive walk-in closet where she opened up her lingerie drawer and spotted the elbow-length velvet opera gloves. She’d only ever worn them once but she remembers the way they felt on her arms and how luxurious it made her feel.

Watching herself in her mirror she slid each glove up her arms and posed, raising her arms over her head to lift her tits and make her tummy appear more svelte.

She grinned as she turned and then she had a sudden idea. Opening up her jewelry armoire she was presented with shiny, sparkly bobbles and jewels.

“Siri… shuffle music by Sara Vaughan to the master bedroom speakers.”

When the jazzy slow music began to play she traced her gloved fingers over the diamond necklace she often wished she could wear every day. It was littered in diamonds, the drop cutting down to just above her cleavage. Lifting it up she placed it gently over her head and laid it over her bust. It was spectacular. Heavy and twinkly and chilled on her skin. She smoothed her hands down her body and stared at her figure in the mirror wearing nothing but gloves and the ridiculously expensive necklace Harry had bought her.

Which then gave her the idea to add on the pretty rainbow jewel body belt. The thin chain was loaded with various colored diamonds, emeralds, rubies, topaz… The end of the chain draped down her back, laying just over her bum with a pretty pearl at the end. Then she put on the drop diamond earrings that matched the necklace. The bottom diamond was so big it nearly reached her shoulder when she shrugged.

She layered pearls and opals and her diamond bracelets over her gloved wrists and then slid on her black high heels, doing a dramatic twirl and bending to see her backside with a giggle.

She swayed her hips to the sexy music crooning through the speakers and then grinned at herself in the mirror, “Look how pretty… Daddy would love this.”

Feeling her naked skin under her gloves was a dream. The way the velvet ran smoothly over her flesh felt sexy and the more jewelry she layered on the prettier she felt. All sparkly and fancy with soft skin and perked nipples.

Sitting her video camera on its stand next to the mirror she hit record and began dancing slowly with herself, all decked out in diamonds. Running her hands over her curves and up to her tits she bit her lip and looked at the camera, “There isn’t anyone that wouldn’t want to have this…” She spun around and laughed to herself before bending at the waist and spreading her thighs just enough that the camera could catch the view of her pussy from behind.

Peeking over her shoulder she stared into the lens and drew a hand down her back and over her bottom before swatting a cheek and moaning softly, “Not so bad with the glove,” she spoke aloud as she lowered her fingers until she could feel the velvet sliding over her pussy, back and forth.

Humming she looked at herself in the mirror and then pressed her finger over her other tight hole, “Needs a little sparkle, doesn’t it?”

She stood up and pulled open her toy drawer to select the plug of the night. It was an easy choice. The anal plug with diamonds. Real diamonds. Another thing she didn’t often wear because it was the least practical of her plugs. But it was pretty.

Stepping back up to the camera she held the plug up and drizzled lube over the tip then repeated the words of the song Whatever Lola wants, Lola gets…

Bending at the waist, ass aimed toward the camera she took her left hand and pulled at her cheek as she began to push the plug into her hole with her right hand. Y/n had become quite the expert at putting in her own plugs. She was used to it now. Even though Harry always told her to not do it when he wasn’t present, she often did it anyway. They had fun with it every time he found out she disobeyed him (but she knew he secretly loved it).

“Oh!” She squeaked when the cool metal fit into place and stretched her out. “Feels so good…” she swayed her hips as she spread her ass cheeks for the camera and hummed to the music.

Turning around to face the camera she tutted at herself, “Beautiful… So sparkly. Think I deserve a treat,” she grinned at her reflection and brushed her hand down her torso to her hips, and raised the other arm over her head as she toyed with her clit and gasped.

Of course, she was putting on a little show. Something to watch later on in private. She’d gotten in the habit of making little videos of herself dancing naked or masturbating. Or just talking about nothing really. She’d started to feel so confident and happy with herself thanks to Harry. And the videos were her naughty little secret. Sometimes, with the extra sexy ones, she’d even touch herself as she rewatched them later on, loving the way she looked.

This time was no different. She was stunning with sparkly jewels and velvet gloves. Long stretched of bare skin, breasts bouncing as she swayed and twirled.

Reaching for her breasts she squished them together with a moan and then jiggled them at the camera before swiping her thumb over each nipple, “Get those nice and hard. We know how much I like hard things don’t we?” She laughed to herself.

Reaching into her toy drawer she found her tiny pink vibrator and turned it on, “Gonna feel so good,” she ran the small toy down the center of her body, between her breasts, over her belly button, and then circled it over her pussy with a sharp inhale.

Moving to the music she kept her eyes on the camera and continued pressing the toy against her clit, “Oh… I’m getting so wet.”

Her breathing picked up and her nipples tightened more, goosebumps covered her skin as she felt the yummy sensation of arousal fill her veins.

“Mmm… I do it so well. Always get myself off. Don’t need Daddy every time, do we?” She chuckled and then gasped when she pressed the toy harder against her bud.

“So wet already. Such a dirty, horny girl…” she bit her lip and turned off the pink toy before placing it on the counter and running her velvet-covered fingers up and down her swollen, wet pussy, “So messy… mmm… Gonna get in so much trouble doing this. I think Daddy’s gonna have to spank me.”

The more she stroked her pearl the wetter her gloves got. She clenched her empty hole and moaned, “Need more. Like all my holes stuffed,” she spoke breathily as she peeked into her drawer and pulled out her clear silicone dildo. The extra long one that was ridged thickly and made her come so fast. She needed to get on with the show. Harry would be coming back soon.

Pulling her soft chair in front of the mirror and the camera she gently sat and cooed at the feel of the plug shifting under her bum, “Oop! Fuck that’s feeling really good.”

Y/n lifted her legs, planting her heeled feet on the seat cushion and spreading her thighs so there was an excellent view of her plug and her pussy.

“I’ve gotten myself all wet,” she drew a finger over her inner thigh and licked at the velvet-gloved finger, “Mm! I know why Daddy says it tastes so good. So yummy,” she sighed as she spread her legs wider and placed the dildo against her pussy lips, running it through her slippery folds before finally pushing it in slowly.

She parted her lips and stared into the camera as she began to work the silicone toy in and out until she could push it in deep and it pressed into the shared wall where her anal plug was. The toy tucked in her ass bobbed every time she thrust the dildo in deep and she moaned at the sight, “Oh my god… that’s so hot isn’t it? Look at how both holes take everything I give them so well.”

Fucking herself with the dildo and rubbing her clit with her gloves she stretched her neck back and whined loudly.

The slick sound of her cunt around the silicone toy filled the spaces between the notes and the music playing, just loud enough for the camera to pick up the sound. Going in faster she lulled her head forward to keep her eyes on the camera but she was in a bit of a daze. She always tried to keep her eyes open for the camera when she came because that was her favorite.

“Good girl, baby… Taking your toys so good. Fucking look like a goddess right now. Oh shit… that’s it… doing it so good…”

Her chest was rising and falling and she heard the chime of an incoming text, which she was sure was Harry, “Daddy’s trying to reach me,” she laughed playfully, “But his little girl is busy fucking herself, isn’t that right?”

It wasn’t long before she was shaking and her body was covered in a light sheen of sweat. Her velvet gloves were ruined with her arousal as she fingered her swollen clit and clamped down on the dildo and the plug with a soft cry, “Oh god! Right there… Fuck…”

Her orgasm had wiped her out. She tried keeping her eyes on the camera but her whole head was swirling with pleasure and lust as she trembled and moaned, creaming all over her dildo.

She heaved and pulled the toy out, dropping it to the floor, and leaned back into the cushion to recover for a moment, “So good. You always do it right. Even better than Daddy sometimes,” she snorted a laugh and sat up to look at the camera teasingly before wobbly legs took her across the space to turn off the recording on her camera.

. . .

Y/n had watched her newest home video at least four times. And she was so turned on every time she watched it, she’d make herself come in record time, rubbing her clit and feeling so proud of how pretty she looked and how brave she’d become since she’d been with Harry.

And the recent video with all the jewels was her best work yet. She really loved it. So much so that she was thinking about sharing it with Harry. She wondered what he’d think about it. She was positive he’d just go nuts over it like she did. He’d act all upset and stoic. Probably give her a good spanking (at least) but she knew he’d adore it.

So, in a moment of sheer insanity or bravery (she wasn’t sure which) she tucked her top row of teeth into her bottom lip, attached the video to a text message for Harry, and squealed when she hit send. She couldn’t believe she’d sent it. All of her solo videos had been her little secret all this time but now she was bringing Harry into the mix by showing him.

It was 2 pm on a Wednesday. He was at the office and probably just getting out of his most recent meeting. And she knew he’d see it shortly after she sent it.

She kept her eye on the screen of her phone, waiting for the message to say ‘read’. It only took a few minutes. She giggled to herself as she snuggled into the couch with her laptop and watched the video, trying to time it so that she was watching it at the same time he was. Wondering what he was thinking with every minute that drew on.

Her heart was racing in anticipation of his response. She knew she’d be in for a bit of punishment but she didn’t know exactly what to expect from it.

But then minute after minute drew on. The video had ended and there was no word from Harry. No bobbing dots to indicate he was texting. No phone call. Nada.

She felt heat creep over her skin as she thought about all the ways Harry would teach her a lesson. Y/n knew Harry was making a plan. Surely he was devising some kind of punishment for her misbehavior. She couldn’t wait.

Less than an hour later Harry was walking through the front door. Y/n peeked over the back of the couch toward the foyer entry and she saw him pass through but he didn’t look in her direction. He breezed by cooly and went into the kitchen.

Y/n scrambled off the couch to follow after him. He was pouring a glass of water for himself silently when she rounded the island and put her hands on his shoulders, “Hi, Daddy.”

He grunted and moved away, making her hands fall from his back as he put the water pitcher back into the fridge before taking a long gulp of his water.

Waiting silently for him to award her a glance she watched her man place the empty glass into the sink as he sighed, placing his palms flat onto the marble countertop, “So you think you can take care of yourself better than I can? Is that right?”

She knew that line would stick out to him.

“I was just teasing. You know no one does it better than you, Da–“

“And you disobeyed me. Looked like you were having the time of your life, Y/n. Did you enjoy wearing all the expensive jewelry I bought you? Enjoyed getting yourself off while I was working hard to keep a roof over your head?” He turned and looked at her. Stern and serious.

Now she knew he was being dramatic. The whole keep-a-roof-over-your-head comment was a bit silly. Harry could retire right then if he wanted to.

“I did enjoy it, actually,” she quipped back before biting her lip.

“Well now at least you’re being honest with me. When did you make the video? Was this today?”

Shaking her head she leaned into the counter, “A week ago.”

He nodded slowly, his green eyes trailing down over her body. She was only wearing one of his t-shirts.

“And what were you up to today that compelled you to send me this one-week-old video?”

She gulped, “Nothing really. Um… I just wanted to share it with you because I liked it. Thought you’d like it to.” She said blinking her eyes innocently at him.

Harry sniffed, “It was very pretty to look at. But you went against my explicit rules. Does Daddy not give you enough orgasms every day? Every morning and every night I work to keep you satisfied. Are you so desperate for an orgasm that you can’t wait a few hours until I get home?”

She breathed shallowly and looked down, “I just sometimes like to do it myself. And I felt so pretty.”

Y/n felt Harry’s touch on her arm, “Come.”

She followed him upstairs to her closet where he opened up her drawers until he found her toys and then her gloves and opened up the jewelry armoire.

“Put everything on that you had in the video. Meet me in the bedroom when you’re ready.”

Y/n felt her nerves bubble as she put everything on. The jewels, the gloves, the plug, and her heels. She sighed as she gave herself a once over in the mirror before stepping out into the bedroom where Harry was seated at the end of the bed facing the TV. Her video on the large screen paused at the beginning. He had his sleeves pushed up to his elbows, ready to get to work.

“C’mere,” he patted his lap. He kept his eyes focused on her body as she neared him and placed her hand on his shoulder to sit down but he pulled her over his thighs, tummy down, and ass up where he gave her a very swift smack and then massaged at the meat of her bum, pulling her plushy cheeks apart and tapped her plug, “Good. Looks like we’re all set.”

Her head was hanging down and the weight of the necklace was especially heavy in her new position, the earrings pulling at her lobes as she rocked over him to stabilize herself. She imagined she was going to need to hang on to something.

“Watch with me. Lift your head. Let’s see this dirty little video my spoiled girl made.”

She scoured the screen with her eyes, her body in view and the jewels glinting off the light from above her. Y/n had to strain to keep her head up. She leveraged herself up with her hand on the bed next to Harry’s thigh.

She had seen the video enough times that she had the whole thing nearly memorized. The music, the moment she bends and shows the camera her plug, the lines she spoke…

Harry spanked her ass, two stinging open palmed swats to each side and she winced at the pain and gasped as she slid down, losing her balance when she kicked a leg up.

“Stay still for me and keep watching,” he spoke gruffly as he grasped the front of her neck and tilted her head back up so she could watch with him.

Gulping into his palm she arched her back when he spanked her bottom again, “Look at how pretty you are in my lap, baby,” he ran his hand down her spine to the little jeweled belt where the pearl hung at the top of her crack, “All these expensive things on your body, ass up for me,” he twisted the plug, “Pussy wet.”

She moaned when he ran his fingers between her crease and pressed his middle finger inside of her cunt before pulling it out and wiping it on the back of her thigh, where he then gave her another smack.

“Who bought all this for you, baby? Hmm? Who made this whole thing possible?”

“You, Daddy!” She didn’t hesitate to answer him.

“That’s right. This video wouldn’t exist if it weren’t for me. This pussy wouldn’t be wet if it weren’t for me.”

She nodded against his palm and moaned when his fingers circled her clit.

“Always my desperate, needy little girl, aren’t you?”

“Yes,” she gasped when he pinched her bud and she wiggled her hips but he gripped her neck tighter, “Don’t wiggle. You got yourself into this mess. These are the consequences.”

She squeezed her eyes closed as he swatted her again before he continued speaking, leaning down to groan into her ear, “Do you know how hard I got the moment I opened up that video at work? Walking down the hall to my office I had to hide my boner and click the volume off.”

She felt him pinch at her inner thigh, giving her clit a moment of respite from his fingers, “Had to calm myself down and lock the door. But then I finished watching your little video and I had to excuse myself to leave work early. Do you know how disruptive that was?”

She grunted as he pressed over her plug, “Right now, I’m supposed to be in a meeting with a potential investor. This was a big deal, Y/n. But I physically wasn’t able to stay at the office for a moment longer, and it’s your fault. Every time I thought about the way you came with your legs spread and this little plug flicking around from the dildo you were fucking yourself with… had to calm my cock. Was gonna burst in my pants.”

His fingers slid back into her cunt, two this time as he pumped into her walls and continued gripping her neck, “Look.”

She shifted her eyes to the screen and her voice filtered through the room, her gasps and moans as she began to come. And just as he described, her little plug was twitching in time with the way she was pressing the dildo into her cunt. It was a pretty sight.

She moaned when he kissed the back of her ear, “Fucking gorgeous when you come, baby. But this video? S’like a work of art. But you were still naughty. Didn’t get permission to do any of that did you?”

“No, Daddy. I’m sorry.”

His fingers were filling her up and squelching with every thrust, “You look so proud of yourself too. So confident. Like a big girl playing dress up with Daddy’s things. And if my cock weren’t throbbing right now I’d really teach you a lesson but I need to come inside of this little pussy. Been aching for it.”

She felt his legs shift and her body was moved, heels on the floor as he steadied her hips before he stood up and began to undo his pants, “Bend over the bed, spread your legs.”

She wanted to watch him pull his cock out. Wanted to see how hard he was but she knew better than to hesitate. She laid herself tummy down on the mattress and spread her thighs apart.

One of his hands was on her hip, lifting her slightly when she felt his thick cock drag against her pussy and then his chest was pressed into her back, “No one does it better than, Daddy.”

The moment he finished his sentence, lips against the shell of her ear, he slammed his cock inside of her. He took both of her hands in his, the velvet gloves keeping her from feeling his palms, as he pulled her arms behind her back and took both wrists in one big hand as he continued rocking into her.

She felt a sharp smack on her ass again and he grunted, thighs flexing as he worked into her. Her shoulders burned as he kept her arms held down at the middle of her back, one hand groping her ass cheek.

The view he had was gorgeous as always. Her plug pushed and pulled with every thrust of Harry’s cock and he could feel the press of it gliding over his cock through her tight warm walls.

The necklace was digging into her chest but she welcomed the way it felt on her skin as well as the burn of another swat to her bum because her body was giving itself over to him.

“My spoiled girl just keeps getting whatever she wants. Even when she’s naughty she gets all these pretty things; gets Daddy’s cock inside of her, gets all the orgasms she can handle. Guess you’ve got me wrapped around your finger, don’t you, baby?”

“Umph!” She croaked, her cheek smushed into the comforter, letting go of her ass as he leaned over, palm on the mattress, and drove into her with the kind of force she loved. It felt so much better than anything she could do to herself with her meager dildo. Harry’s cock was exactly what she needed.

“Yeah? Didn’t hear you make that noise in your little video.” He buried himself in, bullying another lewd sound from her throat as his hips rutted against her ass.

“Can’t help those pretty little noises can you? Daddy’s cock will always feel better won’t it?”

She was jolted forward, her mouth open with drool pooling over the blankets, “No… your cock… aoohha!”

Harry grinned at her inability to answer properly as he continued pounding into her, still holding her wrists together at her mid-back.

“Squeezing the fuck out of me baby. There you go… fuck…”

Y/n’s orgasm wiped her body out. The way the plug was stretching her out and Harry’s big cock was slamming into her guts she couldn’t hold on for a second longer.

She heard Harry panting between grunts and then felt both of his hands on her ass as he pressed in deep and unloaded himself, filling her insides with his come.

“My pretty baby. Love seeing you dripping in diamonds and all fucked out of your mind. Does it make you feel good baby? Wearing all these expensive things?”

He had his chest pressed into her back as he spoke quietly into her ear, hips pasted to her ass.

“I love it. It’s so nice, Daddy.”

He moved off of her, reaching an arm under her waist to pull her up to standing, and turned her in her arms, “Look at this,” bringing her gloved hands into his, he lifted them upward, “Ruined. Need to buy you new gloves it appears.”

She realized the cleaning job she’d done on them after making the video had been shoddy at best and now the tips of the fingers were steaky and lighter than the rest of the material, “Maybe dry cleaning?”

Harry pursed his lips as he began to take off her bracelets, unhooking each clasp, “Maybe. Not sure these can be salvaged, though.”

When he pulled her gloves off he reached around her neck to undo the necklace and then her jeweled belt before running his hands up and down her arms, “Gorgeous with or without all the diamonds,” he smirked.

“I like the diamonds, though. Fun to play dress up.”

He raised a brow and brought her left hand up to his mouth pressing his plush lips over her ring finger, “Thinking about what you’d look like with a pretty diamond right here.”

Y/n parted her lips and kept her gaze locked on Harry’s, “Like a… ring?”

Harry laughed at her shocked expression and pushed his fingers between hers as he cupped her cheek with his free hand, “Yeah. Like a ring.”

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