Lipstick & Miniskirts

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Lipstick & Miniskirts Page 50

by John Dylena


  “Oh, that’s not fair!” Brian shouted. “I had no—”

  “I’m sorry, what was that?” Leah interrupted him and cupped her hand to her ear. “Do you know what happens to subs to speak out of line to their mistresses?”

  Brian closed his mouth and looked away from her as she sat down next to him and waved the black rubber cock in his face.

  “Well, my little pet? What happens to slaves who speak out of line?”

  “They get punished, Mistress,” he mumbled.

  “Good answer. Now, what punishment would fit speaking out?” She waved the toy slowly in front of him and gave him the clue to her answer. “Open up.”

  Brian closed his eyes and let his mouth open slightly. She pressed the tip against his lips and pushed it in further. “Keep going. Yes, that’s it. I want to see you lather this up like you did Lee’s cock.”

  His cheeks turned bright red as his jaw opened further, widening the entrance to his mouth just enough for the rest of the head and the shaft to slide in. Leah moved it in and out of his mouth, twisting and turning it as he covered it with his saliva.

  As the toy slid in and out, his jaw relaxed and his resistance faded away. He gripped the comforter of her bed as he wrapped his lips around the dick, his tongue sliding under the base. Blood flowed to his cock and it strained against its cage. Brian groaned from the pressure, his body shifting uneasily.

  Leah looked away from the cock that she was filling his mouth with to this groin and the cage that locked it away. “Oh, what’s the matter, Brian? Are you getting aroused by this cock in your mouth? Are you imagining it to be Lee’s, or perhaps some big, black stud’s?”

  Brian mumbled an answer, and Leah took the cock out of his mouth so he could speak clearly. “Yours, Mistress. I’m imagining it’s your cock.”

  Leah blushed. Her cheeks were so hot she could cook an egg on them. She covered her mouth and looked away from Brian, and when she turned back, he could see a tear in her eye.

  “Damn it, Brian! I can’t be your Mistress if you make me cry like that.” She leaned forward and kissed him on the lips. “Why did our first date have to fail like that, and why did we grow so far apart? But that is a discussion for later, when we have had our fun and when our bodies need to rest.”

  She got up off of the couch before Brian could answer and moved behind him. Leah placed her hand on his ass and pressed the head of the cock against his asshole. Brian took a deep breath and grunted as she gently eased the toy inside of him. She pushed it in slowly, then pulled it back before going deeper, twisting and turning it with her wrist until the entire length of it entered and the flared tip with the only part visible.

  Brian let out his breath and relaxed his body as Leah secured the toy inside of him. Looking back between his legs, he could see the narrow tube and ball pump. It swung freely until Leah grabbed it and gave the pump a squeeze.

  He moaned as the toy swelled up inside of him, drops of precum oozed out of the tip of his caged cock. Leah pumped it one more time before she was satisfied.

  “How’s that, Brian? Any pain?”

  “No, no pain, Mistress,” he grunted. “It’s just… tight.”

  “Well that’s the point,” she said as she placed her hand on his back. “We need to loosen you up a little. Go ahead and stand up for me, slowly.” He obeyed and she took his hand. “Come, let’s get you dressed. I have just the outfit in mind for you today, one that goes with those sexy heels of yours.”

  Brian followed Leah over to her closet. He looked back at her bed and noticed none of the toys were as big or bigger then what she seemed to be prepping him for. The suction cup dildo was about the size of his own cock, and the vibrator was bullet shaped, something she must’ve purchased for herself.

  She must be hiding it from me. He had no doubt in his mind what it was that Leah decided to keep hidden from him. It was obvious she was planning to fuck him, which meant that she had a strap-on tucked away somewhere, waiting for her to equip it when the moment was right.

  His cock twitched in his cage at the thought of being fucked by her. Brian bit his lip as lust filled him. Up until this morning, he had always wanted to be the one fucking her, but now the thought of her filling his ass with a strap-on made him weak in the knees.

  Leah slid open the doors to her closet and Brian’s jaw dropped. It was far bigger than he imagined, and recalling the modestly decorated condo, he realized that her wardrobe was where she spent her money.

  She had a variety of dresses and tops, skirts from knee-length to micro, pants and jeans as well as coats and jackets. She had dressers full of lingerie in various colors, styles, and fabrics; rows of shoes—most of them high heels—but there were plenty of comfortable, sensible shoes too.

  In addition to the clothing and footwear, Leah had a collection of jewelry full of necklaces and chokers, earrings, bracelets, rings and anklets. In the far back was an armoire, and it was the only part of her closet that she didn’t show to him.

  “No, Brian, that is not for your eyes. Not yet. Come here. It is time to get you dressed,” Leah said as she opened the dresser full of panties.

  Brian hesitated for a moment, his eyes lingering on the old wooden cabinet. He wondered what mysteries it held. Was she some kind of witch and did it hold her spellbooks? Or had she murdered a guy and stashed his body there?

  He shook the thoughts from his head. What was he thinking? From the way she talked about her love of domination, she probably kept some of her more risqué bondage gear there.

  He turned around and froze, and his cheeks turned red when he saw her hold up a red lace thong.

  “Come here, Brian,” she said as she dangled the thong in front of him. “Put on your panties.”

  Leah snickered as he took them from her, slid his feet into them, and fed the tube for the inflatable toy through one of the leg holes. The insert was less noticeable now than it was when she’d first put it in him, but with every movement of his body, it squirmed inside him and rubbed against his prostate.

  He moaned quietly as it stimulated him, his cock begging for release from the cage as another drop of precum oozed out of it.

  “Look at how turned on you are! Shame you haven’t learned to control yourself.” Leah moved behind him and grabbed the pump, squeezing it once. “There, that should teach you a lesson.”

  Brian’s body tensed up and he moaned.

  Leah shuddered as his honey-sweet outburst filled her ears. She bit her lip and squeezed her knees together as she tried to mask the pleasure within her. Ever since she first walked in on him jerking off, she had been so incredibly aroused. She squealed with delight into her hand when he first ran back into his bedroom to get changed.

  She closed the dresser and looked down at her feet, twitching as a bead of liquid lust slid down the inside of her thigh, absorbed by the stockings she wore under her thigh-high boots. Brian was right to assume that the vibrator was hers. She had used to relieve herself of the built-up sexual tension while he showered.

  But it did little to relieve her. Her orgasm was forced, and very little satisfaction followed. By the time she’d finished putting her outfit on, she was back to where she’d started.

  She straightened up and smiled as she handed him the matching bra. He turned around as he put it on and she clipped the straps on the back together. Then she dug through another dresser and pulled out the dress for him to wear.

  “Oh, yes, this is perfect,” she said as she unfolded it.

  Made from a stretchy fabric, the black strapless dress had two large sections cut out of the sides, identical in size. Both of them were oval in shape and reached around the dress to the back.

  “I got this last year for Halloween when I went to a party with one of my ex-boyfriends,” she said as she handed it to him. “Pull it over your head like a shirt.”

  Brian shimmied into the outfit, which tightly hugged his body. He pulled it down to his waist and hips, tugging the hem down as far as it could go
, frowning and sighing when it barely reached his thighs.

  “It’s not going to get any lower,” she teased. “Now put these on.”

  Brian sat down on the little stool to put the white fishnet stockings on and twitched as the plug went further up his ass as he sat down on it. Fighting the feelings welling up inside, he slid his feet into the fishnets and pulled them up to his thighs.

  With the stockings on, she handed him his heels. He slid them on and she led him out of the closet into her bathroom and vanity. Sitting on the smooth counter top, she went to work on his face.

  “Would you say your makeup was convincing when you did it yourself?” she asked as she coated his eyelashes in mascara.

  “I didn’t look like I was in drag, if that’s what you’re asking, Mistress.”

  “And you’ve never had a woman do your makeup before?”

  He shook his head when she pulled her hands away to swap out her tools of the trade. She finished his makeover with a coat of lipstick and covered that in a layer of shiny clear gloss.

  “Perfect,” she said as she smiled.

  Even without his wig on, Brian looked convincingly feminine, leagues better than when he’d applied it himself on that fateful day.

  “Wow.” It was all he could say.

  Leah slid down off of the counter and returned with his blonde wig. She put it on his head and finished the transformation. Other than his Adam’s apple, there was no hint at his masculinity. It was all gone, skillfully masked by a true professional.

  “Much better, don’t you think?”

  Before Brian could answer, Leah helped him out of his chair and back into the closet where she gave him jewelry to go with his clothes and makeup: another pair of clip-on earrings, some bracelets, and of course, an anklet.

  “I believe this is yours?” she said, holding up the ‘slut’ anklet. “Lee put it back with the rest of the jewelry he borrowed from me. I think you shall wear again.” She smiled as she bent down and wrapped it around his ankle.

  Leah took his hand and led him back to the bedroom.

  “Just one more thing.” She reached down and grabbed the collar, wrapping it around his neck and tightening it. “There. The transformation is complete. You are no longer Brian. You are Brianna, a woman and my little subbie. Understood?”

  “Yes, Mistress,” he said as his cheeks turned red.

  “You sure don’t sound like a woman, Brianna.”

  “I’m sorry, Mistress,” he said again with best female voice.

  “Much better. Now, clear off the bed so that we can begin.”

  Brian bowed his head, then grabbed the remaining toys and returned them to the bags they came from. Leah sat on the edge and watched him intently. Once he was done, she ordered him onto his knees.

  “I’ve become quite aroused from all of this. I want you to pleasure me.”

  Leah grinned as Brian knelt down in front of her. His fingers reached up under her dress and pulled down her thong.

  Holy shit, she’s soaking wet! She wasn’t kidding about being turned on. All of this from today? He swallowed hard as he buried his head between her thighs and she squealed with delight as he tongued her.

  Brian wrapped his arm around her right leg and covered her supple flesh in innumerable kisses. He parted her outer lips and lifted up her tiny clit hood with his fingers, giving his tongue access to the sensitive pearl beneath it. Leah responded to his movements with a drawn out moan as she fell back onto the sheets.

  He looked up at her from in between her legs, his tongue flicking back and forth. Brian’s fingers moved to her inner lips, tenderly pulling them apart and fully exposing Lean’s pussy.

  “Oh god, yes!” she cried out, squirming on the bed as he kept up his assault with his tongue. “D-Don’t stop!” She squeezed his head with her thighs, holding it in place as he brought her closer and closer to sensual bliss.

  Her strong legs muffled his hearing, but he could still make out the sound of her scream as she arched her back and filled his mouth with her juices. She relaxed her still-quivering legs, releasing him from her grip.

  “Oh, Brianna, that was wonderful,” she said breathlessly. “I didn’t know I could moan that loudly. It’s time I rewarded you for your excellent demonstration.”

  She climbed up off of the bed and he watched her enter the closet and close the doors behind her. Moments later she returned, brandishing a bright pink strap-on attached firmly to her hips.

  “Up on the bed, Brianna,” she purred.

  “Yes, Mistress,” he replied, climbing up.

  She stood behind him, lifted up his dress and pulled aside the thin strap of his thong. Leah released the air out of the plug and slowly worked it out of him. He grunted and sighed with relief when she pulled out it, but the sensation didn’t last long.

  Leah placed the head of her cock against his asshole and slid it in, slowly burying the entire length of it inside him. Brian moaned loudly as she filled him, and he gripped the sheets as she pulled back out.

  It was slow at first, but as she repeated the in and outward thrusts, Leah picked up speed until her hips were slapping against his. Brian met her thrusts, pushing back against her as she moved forward.

  “Oh, god!” he cried out, his voice soft and feminine. He could hear it in his head and his cock throbbed. He wanted release so badly, but it was locked away. He looked back at her over his shoulder and saw the key chain around her neck, bouncing up and down off of her body as she fucked him.

  “I’m… I’m going to cum!” he said.

  Leah sped up her thrusts until Brian’s head swam with erotic bliss. His moan was long and drawn out as cum erupted out of the tip of his cock. It oozed onto the sheets, but with it came a different from of release. His dick still longed to be freed, and as sweet as it was, it did nothing for him.

  Even after the last drop fell out, his body still cried out for release. He fell forward onto the sheets, his body spent but still incredibly aroused.

  Leah pulled out of him and walked away from the bed. He watched her return to her closet and return sans strap-on.

  She climbed onto the bed, laid down next to him and cuddled.

  “It’s okay now, Brian. You can drop the formalities.”

  “Thanks, I appreciate it,” he said.

  “Did you enjoy that?”

  “I did, though this cage is getting uncomfortable.”

  “Oh, I’ll let you out later. I think it’s cute seeing you all locked up and helpless.” She wrapped her arm around him and rested her chin on his shoulder. “Say, Brian, whatever happened that night when we were supposed to go out on a date?”

  Brian sighed as he rolled onto his back. “Well, Lee and I were on our way back from the store. He had an apartment key, so I took what I could carry and ran up to the apartment to shower and get dressed ‘cause I didn’t want to be late.

  “When I came back, Lee was putting the groceries away so I said goodbye and went down to my car. I got down to the lot and discovered I had a flat. I was going to text you to say that I was going to be a few minutes late, but I had apparently left my phone in the apartment.

  “I ran back upstairs and asked Lee for the keys to his car and to text you to say that I was going to be late, but he said you had already texted him to say that you had changed your mind and decided not to date me.”

  Leah shot up. “What the fuck? What a load of horseshit.”

  “Wait, what? Jesus, Leah. I was telling the truth.”

  “I know. I believe you,” she said with fire in her eyes. “I never texted Lee and told him that. In fact, he texted me to say that you had lost interest. I was devastated, and then a day or so later, he asked me out.”

  Leah fell onto her back and rubbed her face. “No wonder you were so distant with me.”

  “I can’t believe it,” Brian said, “Lee lied to both of us. He didn’t want you to date me ‘cause he wanted to date you. That two-timing son of a bitch!”

  “Brian…
” she began. He looked over at her. Gone was the hatred and rage. Instead there was sadness, a longing. “Lee is going to be gone for a whole week. How about we save the revenge plotting until later and instead we make up for lost time?”

  Brian said nothing as he nodded.

  Leah smiled as a couple tears rolled down her cheeks. She reached up and removed the necklace holding the keys to his cage. Brian bit his lip and watched as she unlocked the padlock and freed him. His cock hardened almost instantly and Leah smiled as she lifted her leg and straddled him. Then she bent down and kissed him tenderly on the mouth.

  TORN APART PART 3:

  REDECORATING

  Leah had grown quite fond of Brian’s new submissive side. She threw her head back and moaned as his tongue wiggled its way deeper into her cunt. She squirmed and giggled with delight as he once again brought her to climax.

  She sighed heavily and smiled as Brian stood up in front of her. The corset he wore shaped his body wonderfully, and the fake breasts that she had stuffed his bra with added to the feminine illusion. His cock was safely tucked away in his panties, locked up in its cage only to be let out at night when they had sex like any other vanilla couple.

  He tucked a loose strand of blonde hair behind his ear and Leah looked up at the new wig she’d bought him. The long hair fell down past his shoulders in waves and he winced as he scratched the back of his neck.

  “Still not used to these nails,” he said, holding his hand out in front of him. His once short, rough nails were now long and smooth. The acrylics that Leah had glued to them were painted hot pink with a rounded tip. They matched the lipstick Leah had applied earlier and the rest of the outfit he wore.

  He reached back and pulled down the hem of his dress. Made of a stretchy fabric, it was hot pink in color and just barely reached his thighs.

  In addition to the dress, Brian wore gold hoop earrings, a rhinestone choker and several gold bracelets decorated with rhinestones. On his feet were pink platform pumps with an anklet, not the ‘slut’ one that Lee had purchased, but a simple gold chain.

 

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