Lipstick & Miniskirts

by John Dylena

  “And the shoes,” she said, pointing to the box.

  Eric removed the lid and pulled the shoes out. They were a pair of tan round-toe pumps that matched his skirt. He wobbled around in the five-inch heels, much to the enjoyment of the witch he now belonged to.

  “Slutty shoes for my slutty secretary,” she said with a smirk. “Now Eric, why don’t you be a good boy and bend over so I can fuck you silly?”

  Eric’s heart shuddered to a stop. “What?!”

  “I said…” Audrey held up her hands and Eric once again lost control of his body. “…bend over!”

  Eric swung around and rested his elbows on the desk, his ass in the air ready for the taking. He brought his chin to his chest and looked at her between his legs as she walked past him to the other side of the desk. She dug through the drawers, her eyes fixated on his.

  “This is orientation, after all. I need to break in my new assistant.”

  Eric’s eyes bulged out past their sockets as she pulled a strap-on out of the desk drawer. She unzipped her tight skirt and placed it neatly on the desk as she slowly harnessed the dildo around her tiny waist and wide, curvaceous hips.

  His body was frozen stiff; hands on the desk, legs spread wide, ass in the air. The only thing he had control of was his head, and no matter where he looked, she was in his vision.

  Audrey’s obsidian-black hair fell loose past her shoulders. The strands glistened in the light, falling just above her ample breasts shrouded beneath the fabric of a low, V-neck sweater.

  They were perfect in Eric’s eyes. Large, round, and bouncy, the kind he could stare at for hours. Unfortunately for him, she kept her top on while she stepped into the leather harness and adjusted the straps.

  The strap-on was double-ended, and Eric felt a rush of heat flow through him as he watched her insert the shorter, curvier end into her warm pussy. His dick throbbed in his panties when her little squeal of pleasure filled his ears.

  His smile quickly faded when his eyes spotted the tiny electrical cord snaking out of the base of the toy to a small rectangular switch. He gulped and looked away from the eager witch to the desk in front of him.

  Only once in his past relationships had the subject of pegging been broached. It was his most recent girlfriend who had mentioned it, but as excited as she was to try it, Eric quickly shot it down. He was a man, and men don’t get fucked in the ass by women.

  Maybe that’s why this is happening to me.

  He stared down at the desk in thought as the clicks from Audrey’s high heels filled his ears. Eric lifted his head and whimpered at the cool application of lube.

  She rubbed her finger around his clenched asshole, coating his skin with the clear goo.

  “So tense. Why don’t you relax a little, Eric? It’ll make the process go smoother, and it’ll be much more enjoyable for you that way.” He moaned quietly as her finger slid into his asshole and pushed all the way up to her knuckle.

  He jerked forward, his mouth open as her finger rubbed his prostate.

  “Like that, don’t you?” Audrey purred in his ear from behind him. “There are a lot of straight men who enjoy pegging. The prostate is the male g-spot, after all. Who wouldn’t want that stimulated? But you won’t be a straight male when I’m through with you.”

  “W-What do you mean?” he mumbled as she pulled her teasing finger out of him.

  “Why ruin the surprise?” she said as she thrust her hips forward, completely stuffing his asshole with her dildo.

  Eric regained control of his body, but all he could do was fall forward onto his elbows. His knees buckled and body rocked back and forth as Audrey thrust deeply into him, relentlessly pounding his ass with her pretty pink strap-on.

  She fucked him with so much force that Eric could hardly breath, riding his ass like he was a wild stallion to be broken in by her thick, veiny dildo. She held the reins, and he was just along for the ride.

  His jaw hung slack as he tried his hardest to stop himself from moaning at the insurmountable pleasure that came from being penetrated. He felt so full, and vulnerable in ways he had never experienced before. Part of him even felt complete. He bit on his hand, stifling the cry that came when she slapped his ass.

  But it was when she flipped on the vibrator that his walls came crashing down.

  He heard the click from the switch, and before he could prepare, the vibrations wriggled through his snug walls, and his body was pushed over the edge toward erotic oblivion.

  It was too much. Too wonderful. He was losing control of his mind and body quickly.

  “Oh god, yes!” he screamed as his cock hardened instantly. The head poked out of the waistband of his panties and gobs of precum flowed from his tip.

  “Does my little slut like that?” Audrey hissed through clenched teeth. She slapped his ass. “Beg for more!”

  She thrust into him so hard that the desk moved underneath him. He leaned forward, raising his ass as high as it could go, his breath leaving fleeting ghosts of his passionate exhortations on the polished surface of the wood.

  His knees threatened to give out on him as she turned up the vibrations. Eric knew he was on the brink of cumming, and if she kept this up, he wouldn’t be able to hold back.

  Before he could even finish the thought, he felt his balls tense and the pressure build.

  “Oh god, I’m cumming!” he cried out.

  “Good! Cum for me, slut!” she commanded.

  The dam inside him burst, and his hot, sticky cum gushed out of his dick and onto the desk, shooting so far that it almost landed in his wide-open mouth. Eric spasmed and writhed, gobs of his lust oozing out as the sensation of rapture filled him to the tips of his fingers and toes. His head swam in carnal ecstasy, but even with his load blown, Audrey continued to fuck him.

  “Time for round two!” she said, pulling out of his ass. Eric was almost sorry to feel her go.

  She grabbed his hips and turned him toward her. His skirt was bunched up at his waist and his panties hung at his knees.

  Audrey put her hand on his chest and mumbled something Eric didn’t quite understand. He tried to make out what she was saying, but his focus shifted from her voice to the sharp pain that shot through his body.

  She back away from him and he doubled over, groaning as he felt his insides rearrange themselves.

  “What... what did you do to me?” he grunted.

  “I said that when I was finished with you, you wouldn’t be a straight man,” she answered smugly.

  Eric straightened up and watched as his chest swelled up just as it had in his dream. Perky C-cup breasts filled the cups of his bra, pushing out against his blouse and threatening to pop the buttons.

  The tightness around his stomach vanished as he thinned out. His waist narrowed, creating a smooth curve between it and his widening hips. His ass rounded out and ripened, filling out the curves of his skirt. The tightness in his groin could have only meant one thing, and lifting up the hem of his dress, he watched his cock and balls shrivel up and disappear inside his body, replaced by a sopping wet cunt.

  He looked away from his new pussy to his fingers, watching as they become more slender and his nails grew long and manicured.

  He lifted his hands to the golden locks tickling his ears and realized his hair had grown down past his shoulders.

  “You turned me into a chick!” Eric covered his mouth, startled at the honey-sweet female voice that flowed from his pouty lips. He blinked, his iceberg-blue eyes staring at Audrey with confusion and panic.

  “I said you wouldn’t be a male when I was through with you,” she repeated, placing her hands on her hips. “Now, why don’t you plop that round ass of yours onto the desk so we can finish what we’ve started?”

  Eric looked down at his new female body, taking in his long, smooth legs; his mouth-watering curves; his eye-catching breasts. He ran his fingers through his silky blonde hair. I look like the women in my dreams!

  “Will it hurt?” he asked, his vo
ice quiet and shy. It was strange hearing this soft, sexy voice coming out of his mouth, but as weird as it was, it was also soothing. It was the kind of voice he could listen to all day.

  “Only in the beginning,” Audrey answered, her eyes hungrily scanning every inch of his creamy buttermilk skin. “But once you push past it, the pain gives way to marvelous pleasure, and you forget all about it.”

  “There’s no getting out if this, is there?” He looked back at the desk and the pools of cum splattered across the surface, the only evidence that he’d ever had a cock—that he was ever a man.

  “It’s not all that bad,” she assured him. “Besides, working for me has its perks. For one, I am a witch, and that opens up a whole realm of things that a normal woman can’t do. Like this.”

  Audrey snapped her fingers and Eric went weak in the knees. He had to grab onto the desk in order to stop himself falling. His whole body was on fire and his skin glowed. His face was cherry red as he looked around the office, light-headed.

  What is this feeling? I... I feel so... horny!

  “Are you aching, Eric? Or should I say: Erica?”

  Audrey took another step forward and a second wave of erotic energy passed through him. He looked at her and found his gaze lingering on her cock.

  Why can’t I take my eyes off of it? I... I want it so badly.

  “Well? Shall we seal the deal?”

  “Y-Yes, Ms. Feana,” Eric said, biting his lip. He was burning up, his body hungry, craving her toy cock. He wanted to be stuffed so badly.

  Regaining control of his body, he heaved himself onto the desk and looked to his boss expectantly.

  “Look at you, so eager and willing! Hard to believe you were once a man.” Audrey grinned as she pulled his soaking wet panties off of his legs and held them in front of him. “Look at the mess you made!”

  “I... I’m sorry, Ms. Feana,” Eric whimpered, batting his lashes.

  Audrey licked her lips. “Sorry ain’t going to cut it, slut. Spread ‘em!”

  Eric opened his legs, exposing the hot, wet sheath between them. She rubbed the insides of his thighs as she lined up the head of her cock with his quivering entrance and pressed it against his delicate lips.

  “How bad do you want it?” she whispered.

  Eric whimpered. “Please... please fuck me, Ms. Feana.”

  “Oh? I’m not convinced,” she said, rubbing her shaft between his inner folds.

  “I want it so bad!” he cried, wriggling his hips against hers. “Please, fuck me!” Eric fell back onto his elbows as he moaned, pushing his cunt forward toward his boss’ dick.

  “Now that’s what I’m talking about!” she praised, grinning wide.

  Eric threw his head back and cried out as she plunged into him, filling his sopping wet cunt with her smooth, thick cock.

  She thrust deep into him, grinning from ear to ear as she watched him succumb to the pleasure of being fucked like the dirty little sluts he always dreamed of. Eric’s inner walls gripped her meaty cock, pulling it in deeper and not letting it go. Audrey rocked back and forth, rolling her hips and picking up the pace as his cunt desperately milked her.

  “Are you ready, slut?” she asked him, her voice strained with pleasure.

  Eric looked up at her through half-closed eyes. He was in a daze, his mind flooded with bliss as she ploughed him ravenously. Never before had he felt this wonderful. As good as it was fucking a woman, being fucked as one was a thousand times better.

  How could he ever go back to being a man? Would Audrey even give him the chance to return to his old self? If she did offer it to him, would he even take her up on it after experiencing the heavenly rapture that came from having his pussy fucked?

  The flip of the switch and the pulsating rhythm from the vibrations cleared his mind of all thought. The only thing he could focus on was the pleasure and how wonderful it felt. It touched him to the very core of his being, reverberating throughout his body from the tips of his toes and his fingers to the crown of his head.

  “Oh, god!” He threw his back into the air, lifting his hips off of the desk as he plummeted into an abyss of ecstasy. His eyes rolled back into his head as his pussy shuddered violently, spraying Audrey’s dick with a torrent of his sweet juices.

  Eric shuddered as the last of the waves subsided and he stared up at the ceiling, his body quivering and his heart beating furiously. His breasts bounced with the rhythm of his pulse, eliciting quiet simpers from between his full, sumptuous lips.

  Audrey pulled out of him and the buzzing of the toy filled his ears like the distant hum of a beehive. She flipped the switch off and put her hands on her hips.

  “Well Eric, orientation is over. Now put your panties back on and get cleaned up,” she said, looking at her watch. “I have an appointment in twenty minutes and I don’t want my guest seeing you all sexed up.”

  “Yes... Ms. Feana,” Eric whimpered as he slid off of the slippery desk. He bent down and picked up his panties, shuddering as the still-wet fabric pressed up against his dripping pussy. Beads of lust slid down his legs as he wobbled behind the desk and plopped down on the leather chair.

  He barely had a minute to compose himself before there was a knock on the door. It opened only a moment later, and Eric scrambled to tidy himself. His eyes widened when he spotted the pool of cum on the desk.

  Grabbing a tissue, he wiped up the ejaculate and tossed it into the trash before the visitor knew what just happened. He stared at Eric and smiled.

  “Have a seat, sir,” Eric said to the man.

  “Thank you, miss,” he said in turn.

  “Ms. Feana, your appointment is here,” Eric said into the phone.

  “Send him in, Erica,” she replied.

  He twitched, his legs squeezing together as the burning heat passed through his body.

  “Go on in, sir,” he said, trying to hide his discomfort.

  “Thank you, miss,” the man said, walking past him into Audrey’s office.

  Eric moaned the second the door closed and he fell forward onto the desk, exhaling deeply. And this is just the first day!

  NIGHT OF THE BIMBO

  It was a dark and starless night, and Sean walked down the street on his way back from a visit to the local strip club. He was an average man, thin with brown hair and eyes and a little bit of scruff on his chin. His job was mediocre, but paid well enough for him to live a comfortable life.

  He was minding his own business when a van pulled up beside him. The doors flew open, and two masked women jumped out and grabbed him. He resisted and tried to break free, but soon felt a pinch in his neck where a gleaming syringe pierced his skin. The clear fluid inside its chamber entered his bloodstream, and in moments, Sean was out cold. The ladies dragged his body into the van and drove off.

  When he awoke, he was not only tied to a chair, but was also naked and hairless from the neck down. Two beautiful blondes watched him while a third had her back to him.

  “He’s awake,” one of them said. He tried to talk, but his mouth was gagged.

  “Do you know who we are?” the woman with her back to him asked.

  Sean muttered a muffled “no,” and the woman turned, revealing her identity. He instantly recognized her.

  A week ago, he’d been sitting at the strip club bar, and after a few too many drinks, he’d said some harsh things to one of the waitresses—something along the lines of calling her an “air-headed bimbo.”

  Instead of making a big deal about it, she’d seemingly ignored him and kept her feelings on his commentary to herself. Sean, in his drunken state, forgot the words he’d said minutes later when he turned his attention back to the ladies on the stage. But now it seemed that the waitress hadn’t let what he said to her go without consequence.

  “You said some harsh things to me last week,” she said, smirking smugly. “And I figured I should teach you a lesson. My friends and I are going to help you experience a night you’ll never forget.”

  She
walked up to the table next to him and grabbed another syringe. This time, the fluid was a pale orange color. She stuck it into his shoulder and injected him.

  “This is a paralytic. You’ll have no control over your arms and legs. Don’t worry; it’s only temporary. But it will last long enough.”

  The three women laughed as they untied him. Try as he might, Sean couldn’t move his arms or legs.

  The three women picked him up and laid him down on a cold metal table. He felt a chill race through his body as gooseflesh prickled his skin. He looked up at the ceiling and saw his reflection in a mirror. Not only was his body hair all gone, but his face was free of stubble.

  The women walked behind him and returned with the last things Sean wanted to see.

  “Phase one,” one of the ladies said, showing him the metal chastity cage before locking away his manhood. The other two were applying glue to a pair of very large silicone breasts.

  “Bimbos have very large boobs—like, bigger than double D’s.” They laughed as they pressed the falsies onto his chest, gluing them in place. Afterward, they applied concealer to the seam, making them look like real breasts.

  “Bimbos also have very curvy bodies.” They lifted his waist off the table and slid a skin-colored corset underneath. One of them climbed on top of him and fastened it, squeezing his waist into an hourglass shape while the other two glued matching padding to his hips and butt. One returned with a black bra, and the other with black panties.

  “I hope this will hold those massive melons you got there.”

  The three women laughed as they continued dressing him. The bra fit perfectly and the lace panties covered his caged manhood.

  They left again, only to return with a bright pink dress with a shiny silver trim. Lifting him up, they slid the dress down his limp body. The thin fabric hugged his curves and the hem barely went down to his thighs. If he bent over, his panties would be exposed for all to see.

  After the dress, one of the ladies held up a shoe box and removed the contents: a pair of glittery, bright pink heels with a locking ankle strap. She slid them onto his feet and locked the straps, pocketing the key to the tiny locks that kept them on his feet. From the neck down, he looked like a big-breasted slut.