SIDESTORY - The Ditzy Dominatrix (Patreon)

Hi! There's three more stories to go in the month - Sandcastles/Luffy316 has been writing up a storm! We're very lucky to have him. Here's an OC of his own making; Connie, a pink-haired dominatrix with a very unorthodox attitude. Read on!

(And if you're a fan of his stuff, consider donating to his own Patreon here!)

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The young man double-checked the address. He was shy to begin with, so he wasn’t sure how he’d live with himself if he went to the wrong house and asked for his dominatrix. When everything matched up, he sucked in a breath and knocked on the door.

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“Oh crap! He’s early!” 

Connie Sawyer double-checked her makeup in the mirror and went bounding down the stairs. Her high-heeled boots clacked lightly against the hard wood of her stairs. Her round boobs jiggled with every hurried step, finally coming to a stop as she reached the bottom. She pulled a silky robe around her lewd attire, holding it tight against her chest as she opened the door a crack. 

Connie was in her mid-twenties with fair skin and long, straight pink hair. The hair WAS a bit messy from her race to the door, dangling just over her big blue eyes. She was a steady 6 feet tall, even before her boots, and bright purple lipstick stood out against her voluptuous lips.

“Hiiii~!” Connie chimed sweetly, wearing a big smile on her face. “Are you from the ad?”

“Yea! You’re um… Connie, right?”

“You remembered~! Come on in~!” Connie said happily. Her full-lipped smile widened as she opened the door wider and let her latest customer come inside. It was an old two-story house, looking large and tidy enough that the guy could almost mistake for a miniature mansion. He was so caught up in the atmosphere that when he turned back to face her, Connie had already shed her robe.

“Of course, you can just call me Mistress,” Connie purred. The bright-haired woman had an intense hourglass figure going on. She wasn’t terribly thin, but her rounded hips and breasts stuck out far enough compared to her slender belly that her stunning figure resembled that of a Barbie doll. The high heels boosted her ass into an even perkier shape and showed off her long, shapely legs. She wore a black corset that lifted up her well-rounded jugs and showed off her inner thigh, temptingly shy of exposing her privates. She had a small cap of matching black leather clipped neatly atop her hair to complete her dominatrix look. She even had long leather gloves and a riding crop that she’d hid beneath the sleeves of her robe.

“O… okay,” the young man babbled. He was a sub at heart (as well as a beta and a bottom), so his every instinct kicked in. He was dying to give himself over to this woman.

“Or, like… Connie’s good too,” the woman added with a more thoughtful expression on her face. “So like, whichever sounds better~!”

“Uh… mistress is fine.”

“Great! And as for your name…” 

“Oh, I’m T-”

“Shhhhh~! I wasn’t asking you, sweetie~.” Connie pressed a gloved finger to his lips. “I think I’ll call you… Mongrel for today. Do you like that, Mongrel?”

Mongrel was speechless. He shivered at her sweet voice dishing out such stern orders and nodded obediently.

“Well, no, actually… you’re too cute for Mongrel,” Connie backpedaled again. She took her hand from his lips to tap her chin. “How about… Puppy!? That’s a super cute name, don’tcha think?” 

Puppy paused at the change of heart. “That’s… fine. Anything you say, Mistress.”

“You’re such a good boy, Puppy!” Connie praised him with a pat him on the head. “Now follow me! I can show you to our special little dungeon.”

The taller woman giggled and trotted up the stairs ahead of him. Puppy watched her ass jiggle at eye level with him, wobbling freely around the thong back of her outfit. Even from behind, he could see her breasts wobbling back and forth. Connie definitely wasn’t what he was expecting when his friend recommended her as his first professional femdom, but he found himself following her hypnotically swaying booty.

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The room gave Puppy the same impression as Connie; exactly what he’d expected and yet completely not. A large canopy bed rested against the wall, its black, nearly translucent curtains pinned back to expose the mass of fluffy pink pillows and flowery bedspread. It contained several large dressers and wardrobes, and one of the walls had an ornate rack of sex toys. Handcuffs, blindfolds, gags, vibrators, strapons… and a few things that Puppy could only guess at their purpose.

Immediately next to one toy collection was a dresser absolutely covered in fluffy stuffed animals. They came in all shapes, colors, species and sizes, but a few stood out from the bunch. Some were nothing but fuzzy bunnies or cats, of course, but there was a turtle wearing tight-fitting bondage gear around its shell. A unicorn with a ball gag tied over its muzzle. A teddy bear in a full gimp suit, complete with a zippered hood over its mouth. That alone explained a lot about the woman.

“Okayyy~! Welcome to my dungeon~! You’re gonna be my cute little prisoner for a while, so let’s get you comfortable.”

“Oh… okay,” Puppy said as he squirmed anxiously.

Connie slapped her riding crop against one of the dressers.

“I said get in bed, bitch!” she snapped suddenly. “Lose the shirt and drop those pants!” Puppy didn’t think twice before hurrying into bed, pulling his pants off as quick as he could.

“There’s a good boy~,” Connie cooed as she slid into bed after him. “Now can you roll over like a good boy?”

Puppy nodded and rolled onto his stomach. Connie giggled sweetly as she adjusted his hips for him, guiding him until he was on his knees with his ass raised in the air.

“There’s mommy’s good boy~!” Connie praised. She cleared her throat and raised her voice a little. “I mean... ‘naughty boy!’ You’re a naughty boy, aren’t you!?”

“Yes, Mistress. Very naughty.”

“Well naughty boys get a spanking!” Connie clapped her gloved hand across Puppy’s juicy little ass. He sighed and shivered as her fingers brushed against his balls, getting him fully erect in an instant.

“Whoopsie~! That sounded really loud. Are you okay?” Connie asked fussily.

“Um… yea. It’s… it’s fine, Mistress,” Puppy muttered. It had stung a little, but that was the point, wasn’t it? Some arousal that numbed him to that kind of pain.

“Are you sure? Come on up here. Get yourself comfortable.” Connie urged him back to his knees and moved him around until his head was resting on her thick, pillowy breasts. She stroked his hair before her hands slid down his sides. She pressed her breasts into his back as she groped around the front of his boxers, squeezing the rock-hard cock inside.

“Ooh! Okay, definitely wasn’t too hard~,” she muttered. “Not you, of course! I meant the spanking. You’re very VERY hard, aren’t you, Puppy?”

“Yes, Mistress…” he moaned as she fiddled with his cock. Her leather-clad fingers crept curiously under his waistband to stroke the smooth material across his erection.

“Good! I do want my puppy to feel good, after all~! Now what do good puppies do?”

“Woof woof?” Puppy yelped meekly. Connie outright gasped as she let go of his shaft cupping her mouth to hide her massive smile.

“OMG that’s so fucking cute~!” she gushed. “Oh I just wanna turn that into my ringtone~! What a good booooy~! In fact…”

Connie set Puppy’s head on the actual pillowss and went over to her rack of toys (the kinky ones, that is; not the fluffy ones). Running her finger along a wide selection of dildos, she plucked up a rather small item; a soft purple choker with a little silver heart in the front.

“Every good boy needs a collar. That’s how he knows he belongs to a mommy that loves him~!”

Connie happily trotted back and slid into bed next to him, pressing her breasts against his chest. Even with the soft leather between them, her soft and round breasts ballooned over her corset so he could feel the warm flesh against his. Connie cupped Puppy’s chin and tilted it up to face her, carefully snapping the choker around his neck. Puppy could feel the silver heart against his Adam’s apple when he swallowed, and he could feel the collar against his skin without really choking him. Connie clearly had experience in fitting these on others.

“There you go~! Doesn’t that look pretty?” Connie cooed as she batted her big baby blues at him. Puppy stared back as if hypnotized by her affectionate gaze and melted in her leather-clad grip. The gleam of the silver against the black collar reflected in her staring eyes until he nodded meekly.

Connie just beamed proudly at the blushing boy before kissing him full on the lips. He shut his eyes and started to squirm without wanting to leave her grip. All her cutesy language and praising sweet talk was overriding Puppy’s expectations for whips and gags and being called a dirty boy. Connie’s pouty purple lips parted as she pushed her tongue into his mouth, bringing the taste of her bubblegum lipstick with it and spreading it around his mouth. She gave such warm, happy hums as she kissed him that he felt like her sweet kisses and praise alone could drain the cum right out of him.

Connie finally broke the kiss when it was clear Puppy had nowhere near the willpower to do so. He still had a trickle of her candy-flavored drool pouring over his lips as he laid there dumbfounded.

“Aww, poor baby. You’re just shaking in mommy’s hands,” Connie cooed, lightly jostling his head around between her gloves. Puppy sluggishly opened his eyes as she peeled herself off him. “You know what we need?” she said with a chipper smile. “Handcuffs. That’ll help keep you still.”

For all her bubbly and clumsy behavior, Connie was a lot more experienced in the bedroom than she behaved. She plucked two sets of handcuffs off her showcase of sextoys, twirling them around her fingers as she strutted back towards the bed. She sat next to Puppy’s head, her fair and round hip pressing against his cheek as she lifted one of his listless arms. She cuffed it to the bedpost before leaning over him, mashing her breasts into his face as the worked on the second set. The mix of pungent leather and overflowing breast flesh nudged past his nose and lips all the while, jiggling her cleavage right in front of his eyes. When Connie finally climbed off him, Puppy could see that the cuffs were not only comfortable, but they had happy chibi bunny patterns along the surface.

“There you go~! No more scared little Puppy. Are those on tight enough for you, sweetie~?” Connie chirped as she gave the short chains a testing tug. Puppy did the same with his other arm, his heart racing with excitement. His submissive side went along with a fondness for bondage, but he wasn’t taking anything at face value with Connie involved.

“Yes, Mistress.”

“Now we can have some real fun~! Just make sure you put on a good show for your audience.”

“My… audience?”

“Of course, silly~!” Connie gestured towards her small army of variously kinky stuffed animals. “They love to watch. Especially Miss Diamond over there…”

She pointed out a large, overstuffed pink rabbit on one end. It was wearing a leather corset dotted with silver studs and an eye mask, a cute little cat-o-nine-tails was velcroed to her paw. Puppy gulped quietly.

“Sometimes she gets so horny that she can’t help but join in the fun~! But don’t worry. I’ll protect you. You’re alllll mine this time~!”

Connie planted a loud, wet smooch on Puppy’s cheek and he could feel the dull stickiness of her lipstick being left behind. The ditzy dom started to kiss slowly lower, teasing along his jawline and lingering around his throat. Her long, moaning kisses went agonizingly slowly as Puppy sluggishly kicked his feet, stirring up the blankets as he squirmed. That only seemed to amuse his cutesy captor further.  

When she reached his chest, Puppy could finally see the trail of purple lipstick marks running down his body. She lingered there to let him admire her work, lightly pinching her teeth around his nipple. He squirmed and squeaked as she smiled wider, curling her plump lips to bare more of her teeth.

“Aww, you need more petting, Puppy?” Connie cooed as she slid a finger beneath the waistband of his boxers.

“Woof woof!” Puppy pleaded, hoping his desperately cute noises would win her over. Connie giggled happily and slid down his underwear, Puppy glad to lift his legs to make her job easier. She planted a few last, tickling kisses down his belly before she tossed the boxers off the bed and turned away from him.

…just to sit her juicy ass on his face. Connie giggled and shivered as she felt his throaty moan vibrate between her cheeks.

“Woopsy~! Didn’t see you there!” Connie chimed as she ran her hands up and down his thighs, stretching herself out on him like a tall and busty kitten. She wiggled her barely covered booty in his face, looking ready to burst out of her clingy clothes as she kissed around his lower body. Her mouth smooches announced her further marking of him like he was her property, branded by her big purple kissy marks.

Her gloves delicately tilted his cock this way and that, letting her lips mark all around it in a crude but cute circle. She held it upright as she kissed right between his balls before planting a couple right up the full length of his shaft. Puppy just mewled and couldn’t sit still, making his struggles contribute more attention to her warm and excited pussy.

“There’s a good boy~! Now here comes a big one. You ready~?”

Puppy mumbled what sounded like another “Yes, Mistress,” as he nodded his head, bobbing her cheeks against his face as he rubbed his mouth against her groin. Connie sighed and opened her lips with a hungry smack before she kissed right on the tip of his cock, her soft lips naturally yielding just enough to slide half the head inside.

“Mmmmmwa~! Ooh, that’s so nummy~!” Connie chimed, cupping her face with delight. Puppy couldn’t see her cutesy nature bleeding through her dom side, but her happy squirming rubbed her cheeks over his face. He moaned as his hands ineffectively tugged against his cuffs in an attempt to grab at her hips and bury himself even deeper. He could feel the same faint tingling as her earlier kisses, though this time in a neat ring around his cockhead.

“Oh I can’t help myself~! I should really be on a diet buuuut… you’re such a tasty little snack. Now say ‘ahhh~!” 

Connie opened her mouth and went down on him again, the tall dom burying his cock past her pouty lips. She rolled her tongue around and moaned as she savored the taste of his light sweat and leaking precum, all but making out with his shaft more than she was sucking on it.

Connie shut her eyes and ran her curling tongue up the top of his shaft when Puppy’s hips bucked, spurting a clumsy mess of jizz into her mouth. Connie gave a startled gasp as she shot back upright, drooling some of her customer’s cum over her cleavage. Puppy’s cock twitched and shot another glob across the kneeling dom’s chest before his hips started to settle down against the bed.

“Oh snap~!” Connie squeaked in surprise. “I’m like, sooooo sorry! I didn’t think you were going to finish so soon! I know you paid for the whole hour and everything…”

Once she lifted her butt from the moaning Puppy’s face, he shook his head wearily.

“No, it’s okay. It’s so good… I’m sorry I couldn’t last longer, Mistress Connie.”

“Oh don’t be sorry~!” Connie giggled, licking up a wad of semen dribbling past her lips. “It’s really flattering when someone cums that fast to me. That just means I’m doing my job right, y’know~?

“You did a really good job,” Puppy said, unable to contain a giggle of his own. Connie was just making it contagious as his head spun in the afterglow. A part of him wondered if that was how the bubbly woman felt all the time.

“Could you… keep going?” Puppy asked timidly, finally unclenching his fists as his huge orgasm faded.

“Ooh~! Can I really~!?” Connie asked excitedly. Puppy nodded and she turned around to kiss him firmly on the lips, refreshing the taste of her candy-coated lips.

“Thanks, sweetie~! Your new dommy mommy know just what to do with her good little Puppy~!”

Connie rearranged herself to straddle his hips, peeling aside the narrow crotch of her corset. Even if Puppy was still mostly flaccid from his orgasm, that didn’t stop her from grinding and moaning on the soft cock sliding inside her. She bobbed hard enough on his cock that he could feel the length of her clit sliding wetly along his recuperating hardon, her breasts bobbing like oversized water balloons. She ended up sliding down that part of her corset as well, never quite removing any of her clothes while still riding Puppy’s cock. She pinched her long, painted nails over her nipples, which that looked almost tiny on the tips of her massive rack. Her bright eyes batting wildly as she got lost in her self-satisfying pleasure and her bubble butt slapped against his lower thighs. Puppy didn’t mind at all. It wasn’t ideal for getting him off, but his ditzy mistress looking so pleased with his contributions that he didn’t care. Her sweet, painted lips were curled into an endless smile as she seemed to know just what she wanted and took it for herself now that Puppy had asked her to do so. Connie might still be getting the hang of the hard dom part, but her happy, gentle femdom was a fresh take that Puppy was glad to experience.

At last Connie gave a long, high-pitched whine as she slapped her hips into his, cumming all over his lap. She elegantly brushed her pink hair back behind her shoulder, giving a relieved sigh as she sank more heavily onto Puppy’s semi-hard cock.

“Phew! That one was a doozie~!” she purred as her warm, clear cum ran down his thighs. She leaned over and rested her hands on his shoulders, planting another sweet kiss. “You were really good, Puppy.”

“Thank you, Mistress,” Puppy said sheepishly. “I’m just glad-”

“Oh crap!” she gasped as she sat back up. She checked the cute little alarm clock on her bedside table. “That was wayyyy more than an hour! I’m soooo totally sorry I kept you so long~! I hope I didn’t make you late!”

She scrambled off the bed and tossed him his boxers. Puppy just stared at them as they landed in his lap.

“Oh. Right.”

Connie took the key from her dresser and unlocked Puppy’s handcuffs. He chuckled as he started to get dressed.

“Really, I’m fine. I wasn’t doing anything else today,” Puppy assured her. “It was outstanding. Thank you so much.” It wasn’t until he swallowed again that he realized he was still wearing her heart-shaped choker. He reached to unclasp it but Connie waved a hand dismissively.

“Oh go ahead and keep it. It looks super good on you~!” she praised. 

Puppy blushed harder than he would have if she’d spat on him and called him a slut. He pulled on his pants before handing her the cash from his pocket. Her given price was surprisingly cheap, so he gave her a little extra.

“Well thanks again~! It was totally super fun~!” Connie chimed. She put her robe back on to see him to the door, planting another brightly colored kiss on his cheek. “And tell Piggy thanks for the referral.”

Puppy smiled and waved goodbye, weighing whether or not to call Bill ‘Piggy’ next time he saw him.

---

Connie shut the door behind him and hung up her robe. She was done with her appointments for the day, so she showered up from her latest sweat and cum-soaked job. She carefully combed her hair before returning to her bedroom, loosely wrapped in a towel that she hugged to her massive breasts. Without the corset on, they looked even bigger hanging loose. She looked at the bed where she had forgot to pick up her handcuffs. She picked them up and looked at them thoughtfully.

“Well he was nice,” Connie noted to herself. “I just hope he doesn’t think I screwed up too bad.”

Connie set the cuffs back on her rack, hesitated, then reached behind her. She picked up a fluffy blue teddy bear and held it up in front of her. He wore a little gasmask and a toy-sized strapon. Connie furrowed her brow and lowered her voice.

“No way, Connie. You were totally sexy back there.” She spoke gruffly as she bobbed it back and forth, pretending to be assured by the toy until she broke into a snicker.

“Thanks, Subby. You’re such a sweetie.” She gave the bear a peck on the cheek and carefully set it back into place before getting dressed in front of her little audience.