Lipstick & Miniskirts

by John Dylena

  As much as she loved dressing Brian up as a beautiful, sexy, and oftentimes slutty woman, she still loved having him around in his normal male form. They’d made up for lost time during the week that Lee was out of town, going out almost every night and staying up late talking, cuddling, or having sex.

  Leah smiled at him and her mind went back to when Brian stayed the night at her condo that first night. She undressed him before they fell asleep, and when he’d woken up, she was gone. There was a note on the pillow saying that she had simply gone to work and would be back in a few hours.

  He rolled out of bed and sighed, stepped into his boxers and walked out into the kitchen, his stomach grumbling. After breakfast, he sat around on Leah’s couch and watched TV, often checking his phone to see if he had gotten a text from her.

  But there was nothing. Leah remained quiet until several hours later when she texted him to say that she was on her way back, and that if he didn’t want to be punished, he would be waiting for her in his bedroom, naked except for the chastity belt.

  Leah returned stressed. Work was driving her crazy, and she wanted nothing more than to relax when she got home. But the moment she laid eyes on Brian waiting for her in her bedroom like she asked, the stress of the day faded and she couldn’t wait to play with him.

  It was like this day after day as the week went by, and she purchased additional items like the new wig and breast forms to enhance their play. Only occasionally did she require him to call her mistress, primarily when she decided to bring out her bondage toys.

  “Let’s do something different tonight,” she said as she kissed Brian’s painted lips.

  “What did you have in mind?”

  “How about you return to your apartment and sleep there dressed up as Brianna?” Leah said as her fingers moved through his hair. “I can give you some sexy sleepwear.”

  “No… I can’t do that. What if people see me and recognize me?” He sat up and looked away from her.

  “You think anyone would recognize you? You look beautiful, and rather convincing.”

  “Even so, people will get suspicious if they see a blonde woman entering the apartment using a key. What if they call the cops ‘cause they think I’m breaking in?”

  “How about this, then,” Leah said as she climbed on top of him. “Why don’t we both go back, then once you’re all settled, I’ll head home and meet you in the morning?”

  “I don’t know. I’m still afraid people will notice me.”

  Leah placed her hand on his cheek and made him face her. She leaned in close and looked deep into his eyes. “Brian, no one will recognize you. I promise.”

  “Okay, I’ll do it. But only if you come with me.”

  “Deal.” Leah bent down and kissed him, then climbed off of the bed and disappeared into her closet. She returned a couple of minutes later with a small bag in her hand. “Let’s head back to your place.”

  “Like this?” he said, motioning to himself. He climbed off of the bed and stood in front of her. “You want me to go back to my apartment wearing this?”

  He wore black patent pumps with dark stockings fastened to a lace garter belt that matched his panties and bra.

  “Of course not! I’ll just give you a dress to wear and you’ll be fine.” Leah set the bag down and returned to her closet, coming back with a long black dress. She helped Brian into it and zipped up the back. “There, now you’re all ready to go.”

  “What’s in the bag?”

  “That’s a surprise,” she said as she grabbed his hand. “Come on, let’s go.”

  Brian hesitated as he stood at the front door of her condo. It was the first time he’d ever gone out into the public dressed up like a woman, and he was sure that everyone who saw him would know exactly who he was. He poked his head out into the hallway and saw no one.

  Like a little kid afraid to step into the pool, Brian slowly eased his foot out into the hallway. His face was bright red. Noticing, Leah held out her hand.

  “Take my hand, Brianna,” she said. “Everything will be okay.”

  He looked into her eyes, and all at once the fear and anxiety melted away.

  She smiled as he took her hand and exited her doorway. The weight of his concern fell off his shoulders, and he decided there was no going back. Leah locked her door, grabbed his hand, and together they headed down to her car.

  Brian sighed with relief as he slid into the leather passenger seat, for the couple had crossed paths with no one.

  “See? That wasn’t so bad, now, was it?”

  “It was… actually quite exciting!” Brian said as he drummed on his legs.

  Before he could say anything more, Leah grabbed the back of his head and brought it toward hers for a long, passionate kiss. She turned the car on and sped off toward his apartment.

  The parking structure was dark and empty as they pulled in. She parked in the visitor parking and got out. Brian’s anxiety had returned, and no comforting look or hug from his new girlfriend could suppress it.

  With a smile and a nod, Leah started walking toward the elevator. After a moment’s hesitation and another look around, Brian caught up to her, walking as quickly as he could in his heels. He wrapped his arms around hers and fell into stride beside her, his face bright red and his cock throbbing in its cage.

  As afraid as he was, being out in public dressed up like a woman was strangely arousing. Part of him wanted people to recognize him under the wig, makeup and clothes, to see what a good-looking woman he had become thanks to his new girlfriend: the tall, gorgeous blonde walking next to him.

  Unlike Leah’s condo, the couple walked past a fair amount of people, most of whom Brian recognized. But they paid him no heed. Instead, they gave the blonde couple a smile and a nod, or a courteous “hello” or “good evening.” They walked past a group of guys that he didn’t know, and Leah wrapped her arm around Brian as the men walked by, their eyes full of lust.

  Brian’s face turned scarlet as the cat calls and whistles filled his ears. “Looking good, ladies!” one of them shouted. “Yeah, give us a kiss!” said another.

  Out of nowhere, Leah turned and pushed Brian into the concrete wall and kissed him passionately. Her hand disappeared under the hem of his dress, its outline visible as it snaked its way to his ass.

  The group of men grew silent. Their jaws hung slack and one of them slowly covered his crotch with his hands. Leah pulled off of Brian, gave the men a wink, then grabbed Brian’s hand and continued walking.

  She opened the door to his apartment and Brian slipped in. He let out a huge sigh and fell onto the couch.

  “See? I told you everything would be okay,” Leah said, locking the door behind her.

  “You could’ve warned me about that kiss, though.”

  “Do you wish I hadn’t kissed you?”

  “No, no… it’s just… never mind.” Brian sighed as he sat up on the couch and watched Leah walk over to him. She set the bag down on the table in front of him and took out the items.

  “Strip naked for me.”

  Brian obeyed, carefully removing his clothes and folding them on the table. Leah took the items out of the bag and set them next to him.

  “This is what you must do for me tonight,” she said.

  “I thought I just had to sleep in your lingerie?”

  “Nope. Since you’ll be here alone, I would like to give you some tasks. But first, here is the outfit you’ll be wearing.”

  She placed in front of him a sheer pink chemise, matching lace panties, white stockings, and a tube of adhesive.

  “What’s the adhesive for?”

  “You will be sleeping in your breasts tonight, so the adhesive is for your falsies. Don’t worry, though. I’s only temporary and will come off tomorrow.”

  Before Brian could complain, she grabbed one of the silicone breasts and applied a thin layer of the adhesive. He silently protested as she pressed it against his chest, holding it firmly in place for a few moments before r
eleasing it.

  She then repeated the process with the other breast, and with both of them securely clinging to his chest, she had him test their strength.

  “Bounce up and down for me.”

  Brian obeyed, and Leah giggled as his breasts bounced. There was no sign of peeling off. They remained firmly glued to his chest. She applied makeup to the seams and turned the fake breasts into a realistic pair.

  “If this works out, we’re going to have to do this more often!”

  Brian frowned as he squeezed them. They looked so much more real now. The thought of having actual breasts sent a shiver down his spine and his cock twitched in its cage.

  Leah handed him the outfit and he slipped into it.

  “Before I leave, these are the tasks that you must do: you are not allowed to sleep in your bed. You are to sleep in Lee’s—”

  “What?! I… I can’t sleep there! His bed is disgusting!”

  “Don’t interrupt me!” Leah shouted. “One more outburst like that and you’ll be going to bed with a sore ass. Understand?”

  “Yes, Leah,” he replied. His voice was quiet, his tone submissive. Leah was scary when she was angry, and the last thing he wanted to do was upset her.

  “Good,” she said with a nod. “Now, you will be sleeping in Lee’s bed, and before you do, you and I will have a nice fun video chat session,” she said, holding up the realistic dildo. “Understood?”

  She handed it to him and he nodded meekly, examining the toy in his hands. The cock was flesh-colored with veiny bulges and a pair of balls that hung from the hilt with a suction cup attached to the base.

  “I’ll text you when I get back to my place.” Leah kissed him on the cheek and left the apartment. Brian remained where he stood, his eyes glued to the dildo long after Leah had locked the front door and left.

  He bit his lip as his thumb rubbed across the smooth surface of the toy, and he looked away from it to his bedroom door. He sighed as he walked into his bedroom and looked around. He stared longingly at his bed and his computer that had been ignored since Leah first walked in on him in his maid outfit.

  Brian closed the door behind him and entered Lee’s room.

  He had been in there before. The last time was when he cleaned it as part of the maid deal. Brian sighed when relief when he walked in, as it was still mostly clean.

  He cringed as he slowly sat down on the edge of the bed and held the dildo in his hand with his phone in the other. He slid further onto the bed, laid on his back and waited for Leah to call him.

  His phone rang and he hesitated, answering it just before the machine kicked in. “Hello?”

  “Hello, Brianna. Let’s begin, shall we?”

  He heard his phone beep, signaling the start of a video chat. He held his screen up in front of him, and moments later, Leah appeared. From her background, Brian could tell she was in her condo’s living room.

  “Show me the room.”

  Brian rolled his eyes as he turned the camera away from him to the room around him.

  “Good. Now the toy.”

  He picked it up and held it in front of him.

  “Good girl. Now, set the phone down beside you and prop it up.”

  He positioned the phone up against one of Lee’s pillows just as she’d asked.

  “Now, slide that cock into those pretty pink lips of yours.”

  Brian’s cheeks turned red as he brought the head of the cock to his lips. He followed Leah’s command and slid it in.

  “Slowly, now,” she purred, grinning from ear to ear. “I want to see you enjoy it.”

  Brian closed his eyes and nodded as he pushed the cock deeper into his mouth. He could hear her egging him, on and he moaned as her voice filled his head.

  Brian moved the cock deeper into his mouth, groaning around it as it slipped past his tongue. His body squirmed and twisted as lust washed over him.

  “You like that cock, don’t you?” Leah said. Brain said nothing, only nodding quickly as he continued to slide it in and out. “Do you like sucking Lee’s cock?”

  Lee’s cock. His mind flashed back to his day as a maid when he had knelt down in front of his roommate and pleasured him. Instantly his body grew hot and the pleasure increased ten-fold.

  “That’s right, Brianna. You’re sucking him off. You’re in his room, on his bed, with his cock between your lips. You’re his slut tonight. You have to pleasure him.”

  Brian nodded fiercely. He slid the cock all the way to the hilt as his left hand reached down to his caged dick. He slipped the tip of his finger into the little hole of his chastity cage and rubbed the head of his cock like it was his clit.

  “Say what you are.”

  He let the cock fall out of his mouth and moaned. “I’m… I’m Lee’s slut! I want your cock, Lee!” His voice was soft and feminine, every word saturated with lust.

  “Now he wants to fuck you,” Leah said over the phone. “Bend over and let him.”

  Brain rolled over onto his hands and knees and reached back. He pulled down the waistband of his panties and slid the soaking wet cock into his ass. He moaned into the pillow as he fucked himself with it.

  As he slid the toy in and out, Leah grew quiet. She gave no further commands. The only sounds that came from his phone were muffled moans and groans.

  Back at her apartment, Leah had dropped her phone onto the couch. She used her now free hand to pull apart her cunt and rub her clit as she shoved her vibrator inside of her.

  Brian’s moans made her squeal with delight, and she bit her lip as she turned up the power on the vibrator. It turned her body to jelly as she threw her head back and cried out in erotic bliss.

  Back in Lee’s room, Brian finally came. His sticky white cum oozed out of his caged cock and he fell onto his side. He reached over and grabbed his phone with his last ounce of strength.

  “Leah?” he said softly.

  A moment later, her hand appeared on screen and the camera refocused on her face. She was breathing hard and covered in sweat.

  “Yeah? What is it, Brian?”

  “Can I go to bed now? I’m really tired.”

  “Go ahead. I’ll see you in the morning. Love you.”

  Brian smiled. “Love you too.”

  The call ended and Leah tossed her phone back onto the couch. She sighed heavily and looked up at the ceiling. Never before had she felt so strongly for someone, but there was still something wrong.

  She wasn’t sure what side of Brian she loved more: his normal male side, or the sexy female that she turned him into. Fuck… I can’t believe I did that to him, she thought as she rubbed her face with her hands. Making him say that shit about Lee.

  Leah was torn. On the one hand, she had vowed to get revenge on Lee for what he did to Brian and her, but would it be worth it? She had yet to tell Brian of her plan to get back at Lee, namely about how it involved him.

  Her plan was simple: make Brian as convincingly female as possible, then use him to have sex with Lee. Brian’s goal would be to get Lee to suck his cock, and then Leah would walk in and take pictures. She would use that to get the truth out of him on whether or not he really did sabotage their relationship.

  But what if Brian failed to get Lee to suck his cock? What if Brian just ended up pleasuring Lee once more, both orally and anally, and Brian decided he’d rather be Lee’s cross-dressing, gay pleasure toy?

  What if I lose him? No, there has got to be another way.

  Her head fell forward as she began to doze. Her post-orgasm glow was lulling her to sleep. A moment later, she jerked into wakefulness again and climbed off of the couch, stumbling toward her bedroom and falling asleep, dreaming of Brian.

  Leah woke up early in the morning, much earlier than she was used to. The sun was just beginning its climb over the horizon, its pale light filling her bedroom and illuminating the rest of her condo. She had tossed and turned at first, and after failing to fall back asleep, she changed into some clothes and went for a run in silence
.

  She remained quiet as she stripped off her sweaty clothes and showered, but her mind was anything but mute. For a long time she stood still, gazing down into nothing as the hot water flowed across her body.

  Until at long last she smiled.

  Leah climbed out of the shower, dried off and got dressed, then packed up some clothes for Brian. She knew what must be done, but there was no way to exclude Brian from her plan.

  She drove over to his apartment and found him silently sleeping on Lee’s bed. The toy that he had played with the night before had fallen onto the floor.

  “Wake up, Brian,” she said as she sat down on the edge. He mumbled as his eyes slowly opened, and he smiled when he saw her sitting there. “Lee is coming home today, so we need to get ready.”

  “You never told me about your plan,” he said, sitting up. “Only that it involved me.”

  “I will tell you when you are dressed and ready. Take a shower and get all cleaned up. Then I’ll get you dressed, do your makeup, and we’ll ready the trap.”

  “So, what’s this plan of yours?” Brian said after another failed attempt to lower the hemline of his pink dress.

  “Sit down, Brian. There’s something I need to ask of you first.”

  He nodded and sat down next to her, still tugging on the hem of his dress.

  “Stop that,” she said, slapping at his hands. “You’ll stretch it out, or worse, tear it.”

  “Sorry,” Brian said with a frown.

  Leah paused and her cute smile vanished. A solemn look covered her face as she turned away from Brian.

  “What is it? What’s bothering you?”

  “It’s you, Brian. You are what’s bothering me.”

  Brian slid back on the couch away from Leah. She kept her gaze forward, her hands locked in front of her.

  “What do you mean? What did I do?”

  “You,” she said, finally looking at him, her eyes wet with tears, “you did nothing—except be everything I wanted you to be and more. No, it’s all my fault.”

  “I still don’t get what you’re saying,” he sighed.