Do y’all remember the Sugarbutch Star stories? It was a series where readers sent in a scenario and I wrote up the story. This is the last of the 5 stories from the 2008 “contest,” the others being Eileen, Matt, Green-Eyed Girl, and Maze. This story idea comes from blkndblue.
Warning: This story is long, about 18 pages. Click the “read more” at the end to read the final scene (it’s worth it, promise). I figure it’s a good way to kick off a (happy, sexy) new year.
Thanks to Dacia & BB Rydell for help with edits!
Sugarbutch Star: blckndblue
THE PINK DRESS
Emily emerges from the dressing room slowly, suddenly shy, though I’ve seen her naked in dozens of compromised positions. She fidgets with the dress, her hair, sucks in her stomach, but her eyes are lit up and she’s biting back a playful smile. She wants to wear this dress. Her inner three-year-old princess is aflame. “What do you think?” Emily asks; but the question isn’t really about my preference. She wants me to want it so she has permission to wear it. Then she doesn’t have to want it for herself; she is absolved of her own desires. I want to her to have permission to want anything on her body that she is drawn to, regardless of its gendered implications.
I finger the skirt of the baby pink dress, its satin fabric, abundant for its near-full skirt. She looks amazing in the plunging neckline in a gentle scoop, which shows off her round breasts generously. Sleeveless, it gathers at the waist where a thick white band wraps around, tying in a ribbon at the back. It could have been a bridesmaid’s dress, or a prom dress, or maybe someone’s fancy party dress. She’s been eyeing this dress in the window display, and today was the day it came down. She asked them to set it aside for her.
“So?” She is trying so hard to be patient. The words come out in a rush. “Do you like it?”
I come up behind her as she looks in the full-length mirror barely visible behind racks of gently used clothes. I wrap my arm around her waist, pull her gently back to me as she sighs, then smooths the skirt down.
“I think it’s perfect,” I say, my lips next to her ear. “No question.”
“Really?” She’s not sure I mean it, but she wants me to. “But it’s so … femme.”
“Yeah, it is,” I say.
“But, I’m not femme!” She argues.
“What do you mean? Of course you are,” I say.
“No, I mean …” she struggles for the words. “I’m not high femme. I hate that term. I almost always wear jeans and tee shirts.” We’ve been dating for on and off for a few years. We both have primary partners, but we make time to play and go on dates. When she dresses up, she adds heels and lipstick, rarely anything more. She has some impressive lingerie, but seldom wears dresses. She wears power suits for her professional office work, where she has to keep control and is in charge of a dozen people’s activities on a daily basis. She spends a lot of time looking put together, climbing the corporate ladder, and fighting the male privilege in her office, and she’d rather kick around in something comfortable and durable when she has the option.
“I know that’s what you prefer, and it’s perfect—your ass looks great in jeans,” I counter. “Look, you’re twice the femme most self-identified high femmes are. You’re at home in your body, awake in your skin, not judgmental about your own waistline or anyone else’s. And you have your circle of femme friends without gossip or backstabbing. If that’s not high femme, I don’t know what is.”
“Yeah, but you have to say that.”
“And I want to. I know the dress is a stretch … but it’s amazing on you. It looks like it was made for you. Doesn’t it?” I ask the passing sales girl. “Doesn’t it look like it was made for her?”
“It is, like, so cut perfectly for your body,” the girl, probably barely twenty, replies. “It makes your curves look even more curvy. It’s practically, like, perfect.”
“Yeah. Perfect,” I echo, and Emily grins at herself in the mirror.
“It is, isn’t it. Yeah. Okay,” she kisses my cheek and zips back into the dressing room, and buys the dress.
The date is my idea, and a surprise. I enlist her friend Sam, a gay boy also known as Serena, who does a fierce drag queen act and has every feminizing, over-the-top accessory one would need. We’ve been out drinking and galavanting dozens of nights in the past few years. Sometimes Emily and I go see him perform. Last time, he did a Judy Garland number with an incredible outfit from the forties that made him look like a black and white movie star.
“I could never do that,” Emily must’ve whispered to me five times that night, but the spark in her eyes told me that she wanted to. I knew Sam would love to see Emily all dressed up.
And tonight, with this pink dress, he’s going to help. I enlist Sam because Emily doesn’t have the femme things I need, and I can’t afford to buy them all. I meet Sam around the corner and pick up the fluffy underskirt that’s used to puff out full skirts, called a crinoline.
I knock on Emily’s door, and she throws it open. “I’m here to pick up the dress,” I say, after kissing her hello. She fetches it from her bedroom, still in the thrift store’s lavender-colored paper bag with their logo on it, and hands it to me across the threshold.
“Thank you. Now, you remember what I told you? What’s the plan?”
“First, I’m getting my nails done across the street. Then I’m going to go to Sam’s at 5pm to get my hair and makeup done. Then I’ll come meet you at your place, and bring the bra and panties.” I know she doesn’t wear the white bra and panty set with the lace trim often. I like that she saves it for me.
“What time, at my apartment?”
“Good. Perfect. Don’t be late,” I add. As if she would be. She shifts her weight from foot to foot very slightly and I can see her ears beginning to flush pink.
I tuck the box with the crinoline under the arm that holds her dress in a shopping bag and draw her to me with the other, smiling as our faces get closer, drinking in her skin and hair and the sweet way her body fits.
“I won’t. I promise.”
“Good girl,” I say, and kiss her.
At seven twenty-eight, she knocks on my apartment door. I greet her with more kisses and lead her into the bedroom before she sets her purse down. Some of the things are laid out on the bed: the crinoline skirt, white thigh-high stockings, a white garter belt, and her new pink dress, which I had dry cleaned and pressed just this morning. I see her hand flicker slightly as she reaches out and touch the dress, then pulls it back and makes a fist.
“Are you ready for tonight?” I take a seat in the small armchair in the corner of my bedroom and I take a sip of the glass of water I’d poured just before she arrived, with extra ice so she can hear the clink of it in the glass. She nods. I notice Emily picks at her nails, then stop when she realizes she is probably chipping her nail polish. She must be nervous. The icy liquid is cool in my mouth and I feel it run down my throat. Her chestnut hair is mostly a silhouetted shadow, but I can see it is piled on top of her hair in spirals and curls in a way that is much more complicated than she would usually entertain. It reveals the curve of her neck, which swoops into her collarbone and, later, will lead right to her cleavage.
“Did Sam send you with jewelry?” I ask.
“Get it out, and put it on the top of the dresser.” I cleared it in anticipation. She goes to her bag, removes a couple small boxes and a tiny clutch purse, then arranges it all so each are neat and not touching, then goes back to standing, shifting her weight from foot to foot and looking around the room.
“Take off your clothes,” I say. “Slowly. Fold each piece and put them on the bed.” She starts with her v-neck grey fitted girly tee shirt, quickly pulling it over her head. “I said slowly,” I say, and she pauses, moves a little slower. She folds the thin fabric easily and places it on the bed, then steps out of her low, simple black flats. She’s not wearing a bra; she often doesn’t, not encouraging the curve of her breasts to be shown off. Her bare skin glows in the lamplight. She pulls down her tight blue jeans and steps out of them, folding them a little thoughtlessly, but I don’t tell her to slow down again. She slides her plain black cotton underwear down over her legs and adds it to the pile. She fingers the worn grey tee shirt and looks at it longingly, then glances at the lingerie laid out on the bed and moves her hand to touch it, smiling as her fingertips make contact, her face relaxing.
She stands again, naked this time, crosses her arms in front of herself, then drops her arms and holds one wrist with her hand. After a moment she straightens up, and clasps her hands behind her back like she is presenting herself to me, a blank canvas. She shifts her weight from foot to foot, drops her hip, but tries to stay still. She bites her lip.
“Very nice,” I murmur from my corner. I uncross and recross my legs, ankle to knee, and pick up the cane from next to my chair. I can see her nipples, even in the shadows, hard and dark. “Get the bra and panties out of your bag, lay them on the bed.” She does. “Now, get dressed. Start with the garter belt.” She takes a breath and turns to the bed, picking it up and sliding it up her legs, securing it in place.
“Now the stockings,” I say. “And the bra. Leave the panties off, for now.” She dresses quickly, fumbling a little with the clasps and the delicate fabric, sitting on the side of the bed to fasten the stockings to the lace. “Now the petticoat.” She looks at me a little questioning, then realizes I mean the white crinoline skirt, and pulls it in a flourish from the bed to step into it.
“The dress,” I say. She pulls it over her head, evens it over the petticoat, and does her best to tie the white bow behind her back. With the extra layers of under the skirt, the pink dress is even more stunning than it was in the store. “And the jewelry,” I say, as she admires herself in the mirror hanging over the dresser. She takes a step closer and puts small two-stone droplet earrings in; they’re delicate, just an inch or so long, hanging just enough to move when she does and sparkle when the light hits them. She reaches for the matching necklace and raises her elbows to buckle the clasp behind her neck. Her fingers tremble and it takes her three tries to hook it correctly.
Emily steps back and looks at her reflection, buzzing, hardly containing the thrill of happiness at her own reflection. Her smile is as big as I’ve ever seen it. She turns her head, then shakes it to see the sparkle of the earrings, tilts her chin down to see her fancy hair-do, fluffs the skirt out to the side, and finally twirls, watching the dress in the mirror and laughing, giddy.
“Come here,” I say. She turns her head to me and takes short, quick steps across the room to where I am sitting next to the window in her stockinged feet. She notices the cane I have been stroking.
“Is that for me?” she asks.
“It’s for your ass. For later.” I set it on the table with my glass and reach out for her waist, pull her on to my lap. “Very nice,” I say, stroking the skin on her arm, the the slick fabric of the top of the dress, brushing my fingers against her breasts and nipples. I offer my mouth for a kiss and she wraps her arms around my neck, opening her mouth, gently kissing back. “You look gorgeous.”
“You really think so?” she bats her eyelashes. She looks like a sunrise, peeking over the horizon, breaking the dark, reaching up into the sky. She still looks like herself—just polished up a little, enhanced, prettied.
“Really. Very much.” We kiss again and I get lost in her lips, her tongue, the way her hands grasp gently at my neck and shoulders. I let my hands trace her stockings, wander up under the many layers under her dress. “Do you like the crinoline?” I ask.
“Oh yes,” she breathes. “Is that what Sam gave you?”
“Yes. On loan.”
“It’s so … pretty.”
“You’re pretty, sweetheart.”
She smiles shyly, kisses me again.
“Did you like getting your nails done, and your hair and make-up done?”
“Yes! It was really fun. More than I thought it would be. I thought it would be weird but it makes me feel fancy. And important. And … ” she lowers her voice, her eyes a little and brings her hands up to straighten my tie, pinch my collar between her fingers. “And I knew I was doing it for you. That you would like it.”
“Mmm. And you did a very good job getting all ready for me.” I find the patch of skin at the top of her stockings, her sweet smooth inner thigh, and rest my hand there gently.
“I like doing what you say.” It lets her mind rest, she’s explained to me, and is a relief to trust enough to follow orders instead of second guessing and being in charge of everything.
“I know. And I have a few more things to do before we go to dinner. Are you ready?”
“Yes.” I toss her a questioning look and she corrects herself. “Yes, sir.”
“Good.” I take a breath. “I’m going to warm you up for the evening. I want to give you something that will serve as a reminder that this body—” I shift my hand quickly and palm her pussy, making her gasp, then quickly attempt to maintain her composure and keep her eyes open, looking at me, “—this pretty little body of yours is mine to play with tonight.”
She nods, quick, tiny movements of her head, and her eyes flicker with a hint of nervousness.
“Are you worried?”
“No, sir. I know you will take good care of me.”
“That’s right. Good.” I move my hand away and she breathes in, her thighs quiver. I lean in to kiss her again, bring my hands to her waist and then up to cup her chin, neck, the back of her head, careful not to mess up her hair. She relaxes, her mouth softens. She tastes like cream.
“Get up and bend over my lap. I’m going to make some marks on your ass before we go out.”
She delicately places herself over me with more care than usual, though we’ve been in this position many times. She doesn’t want to muss herself. This chair is perfect for over-the-knee spankings, with wide, low arm rests. Her stockinged tiptoes just barely reach the floor. She arches her back automatically, presenting her ass and slit to my right hand.
I caress her neck and shift my arm to cradle her collarbone and begin peeling up the layers of her pretty pink dress and petticoat. The peach of her ass is perfectly framed by her stockings and garter belt, the layers pushed up to her hips. Softly, I bring my hand to her thighs and ass and begin caressing.
“So nice,” I murmur into her ear. I start with some rapid tap-tap-taps with my fingers tight together on the sweet spots on her ass, the ones that make the flesh shake and that makes her muscles relax. She sighs, keeps breathing, keeps filling her lungs and breathing into the increasing sensation. She’s done enough yoga, we’ve played with enough sensation play—she knows how to open.
I keep going with light taps and occasional full-handed gentle swats until I can see a pink flush starting, just a hint. She loves being hit; she snuggles down into it as if I was reading her a bedtime story. I increase my swing, raising my arm higher, and give her a few open-palmed, but not too hard yet. Her skin is fair and it is easy to leave long-lasting marks, easy to bruise and break capillaries on the surface of her skin.
Which is exactly what I want.
I continue, warming up her ass until it is bright and hot, flushed and red, beginning to show some darker parts where it will be easy to leave marks. She moans, sinking into me, humming with pleasure. When we are both warm, when my shoulder feels like it is loose and liquid and easy, I raise my arm high and let fly a few hard wallops, pausing in between, but just for a moment, to let her react. Her body shudders and I feel her tense, then relax, over my lap. I can feel the impact of my hand through her and onto my thighs, can feel her growing heat and intensity. I let my hand down again, and again, allowing gravity to pull me, sucking up the power she’s handing over while I have her upturned and stunned, ready to take more.
I lean down so my mouth is by her ear again. “You are doing so well. Your ass is nice and red and starting to bruise. I’m going to get my cane out now.”
She manages to move her neck slightly, twists her head and looks up at me, and nods just a little. I grip the cane from the side table and it feels hard, solid in my hand. It slices through the air with a hiss and I love the way it extends my arm. The last time we used the cane, she told me every time she sat down, she thought about what I’d done and how I’d used her. That it made her wet to have to act like she could sit normally, when really it was excruciatingly painful. That’s how I want it to be tonight. Something to take away from the terror of being so femme, over the top femme, in public. Something to distract her.
The first hit with the cane is a little off, and not too hard. She gasps but does not squirm. The second is two centimeters toward her thighs and harder. Immediately a light stripe appears. She jumps a little and lets one arm drop, grabbing on to my pant leg, as she lets out her breath in a long thin stream through her teeth. The third, quicker now, is at a different angle, crossing the first two. She sucks air back in and lets out a laugh, bubbling like champagne, thrilling and tickling my nose. Good. She’s warm, dropping into that blurry area past the sharp pain and into sensation.
The next dozen or so are more rapid, in succession, some lighter and some fiercely hard and biting. She takes it well. She gasps and begins squirming, but not away, not off of my lap, just to wriggle and shake off some of the building energy. I fall into a pattern of hard-hard-quick-quick-soft-caress where my eyes glaze and my cock hardens. I can see her slit becoming wet, swollen, as pink as her sweet round ass cheeks.
The striping is beautiful, thin welts rising on bull’s eye circles where my hands bruised her first. I can already see some small places where my handiwork reveals itself.
I lean low against her ear again. “It’s going to hurt for a while when you sit,” I say, as a slide the cane away and bring my hand to her singed bottom. It is so tender and sensitive, like stretched skin over the frame of a drum, reverberating with every touch.
She moans. “Thank you, sir.”
I bring her up onto my lap again to hold her for a minute, her ass already uncomfortable. Sitting at the restaurant is going to be excruciating. I stroke her hair and neck, offer her some water and she takes it. She snuggles against my chest, lets me sooth her, then rocks a little on my lap and I realize she is searching for my cock.
“Looking for something?” I ask.
She falters, remembers herself. “No, sir.”
She nods, tries not to look disappointed.
“I have one more thing for you before we leave. Ready?”
She nods again, brings one hand up to her mouth to bite one finger, a childish gesture of nervousness.
I almost laugh. “Nothing bad, sweet girl. This is a present. A surprise.”
Her eyes light up as she slips off my lap. I go over to the closet where I stashed the bag, then sit on the bed, patting the bedspread next to me. She shuffles slowly over the thin carpet in her stockings, smoothing out the skirt of her dress and walking slowly because her legs are still weak from being bent over my lap and beaten. She brings her hands behind her, to touch her ass, as she walks, and I can tell the muscles are already sore.
I hand her the bag. She gives me a shy smile and pulls the shoe box out of the plain white shopping bag. Her eyes widen. She realizes she only brought the flat black shoes she came in.
“Oh!” She exclaims when she opens the box. They took me a few days to find: the exact pink shade as the dress, with a small strap over the arch of her foot, delicate white trim, and a tall, thin four inch heel. She pulls them both out and pushes the wrapping aside on the bed, holds them flat in her hands, grinning. “May I?”
I slip off the bed to kneel in front of her, holding my hand out. She blushes—adorable—and hands the shoes to me, offers me her foot so I can slide them on, one at a time.
She laughs, and twirls. “I feel like these are fancy shoes from my fairy godmother, and I’m Cinderella!”
“You look amazing,” I say, standing up, and offer my hands to help her stand. It may take a minute to get used to them. I take her in my arms again and she melts into me, offering her mouth for more kisses.
When I pull away I take the delicate white panties still laid out on the bed and offer them to her. “Put these on, we wouldn’t want you getting your dress any more wet than it already is. Freshen up your lipstick and let’s go to dinner. Are you hungry?” Her lipstick is smeared from kissing me, and she hasn’t noticed. It’s probably on my mouth. I quickly wipe my mouth in the bathroom mirror and when I come back in, she’s sitting on the bed to step into her panties, pulling them up over her shoes and stockings, leaving them on the outside, so they can be the first thing that comes off later. She stands and picks up the tiny clutch purse she laid out on the dresser, checking her make-up in the dresser mirror. I slide my suit coat over my shoulders, watching her twist the lipstick up and pucker her lips. She would never do these things on her own, but she is flushed and giddy and thrilled, ready to go.