Lipstick & Miniskirts

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Lipstick & Miniskirts Page 65

by John Dylena


  Oh well, work is work… then there was what happened to me after work today…

  “So it’s been four days now and you’ve completely organized all the paperwork. You’re well on your way to getting it all digitized. Not only that, but you’ve been completely submissive and never once acted out. I see a need for a celebration, don’t you think?”

  Reed continued typing away at the computer. His legs were crossed and the way he was sitting, his breasts were about ready to burst through the blouse. “What kind of celebration, Mistress?”

  “Tomorrow night is one of those rare Fridays when I finish before 8pm. So I think we need to go out to a club and I know of the perfect one.”

  He froze. His fingers stopped mid-typing and he turned towards her. “G-go out?! To a club?”

  “Of course! Don’t worry, I am a regular at this club, all the guys there are very nice and respectable.”

  “I… I… ” He was shaking nervously. Going out to lunch was fine because it only required interaction from one person, the waiter or waitress. Going out to a club meant interacting with a lot of people. A lot of horny and drunk people. He thought it was bad enough getting hit on by her clients, but going to a club where she has no authority would be a nightmare.

  She was oblivious to his nervous state. “That means we get to go shopping! And you desperately need to get your nails done.”

  “Shopping?! Nail salon?!”

  “Yes, don’t worry your pretty little head, it’s gonna be tons of fun. Finish what you are doing, then we’ll close up and head on out.” She exited the lobby and disappeared behind the black door. He waited for her to be out of sight before he panicked. He put his face in his hands as his mind went a million miles an hour. His thoughts raced through all the different scenarios from absolutely nothing happening to getting brought outside and raped in a dark alley by a group of drunk and horny men.

  Oh god, what am I going to do!?

  He finished up the client profile he was working on and turned off the computer. By the time he was done, Arina had gone up to her office, changed, and was back down at the lobby.

  “Grab your purse and let's go Raye.” He followed her outside and they got into her car. They drove for a few minutes and arrived at their destination, the local mall. They got out and headed to the women’s dress section. He constantly scanned his surroundings, hoping to not see anyone he knew.

  “Ok, we need to find a nice club dress for you, and a new pair of shoes to match.” For nearly an hour Arina was going around the store, looking at all the dresses. She’d occasionally find one, pull it out of the rack, examine it further then put them back. After going through many potential candidates, she finally decided on one. It was a blue cocktail dress that had no sleeves. It was made of a kind of shiny silk material and was rather form fitting.

  “You need to try this on, blue is definitely your color,” Arina said.

  “Yes Mistress,” he replied. She handed him the dress and they went into the women’s changing room. He went into the stall and removed his blouse and skirt, then he slid on the dress.

  “Come on out when you’re dressed, I want to see you in it.” He opened the door and stepped out. “Let me zip you up in the back… ok good. Now step back and give me a spin. Oh my god you look so gorgeous in that dress… its perfect!”

  “Really? I think it’s kind of revealing.” It was cut low in the back, so much of his upper back would be exposed, and it was even shorter than the skirt he had on earlier.

  “That's the point of a cocktail dress, you’re supposed to look sexy and kind of slutty.”

  A woman walked into the dressing room and stopped next to them. “Wow, that dress does look good on you… you have such nice legs, it’s perfect.”

  “Thanks,” he replied. He turned to Arina who was smiling. “Ok, I’ll get it.”

  “Yay! Now for some shoes, change back into your uniform and let's go shoe shopping.” He stepped back into the room and before he changed out of the dress, he gave himself one last look

  I do look really good in this dress, part of me really wants to wear it ...

  He changed out of the dress and they went to the cashier to pay for it. Arina took out a similar envelope and paid with cash.

  She saw that he was looking at the envelope. “Yes, all the stuff you’ve been wearing I’ve paid for with the money you gave me.” He grabbed the dress, which was now on a hanger in a plastic dress bag and they headed to the shoe section. After a much shorter search, Arina found a pair of shoes for him to wear.

  “Ok, these are perfect. You have to wear them, ok?”

  “Yes Mistress,” he said. They were a pair of 5” silver strappy sandals.

  Those are some cute shoes… wait a second, did I just say cute?! God, with that dress and those shoes, I'm gonna be getting a lot of attention tomorrow… I'm in for an interesting night!

  “Ok, let's pay and head over to the nail salon. Later we’ll get this dress cleaned.” After a painful hour, his finger and toe nails were cleaned, polished, shaped, and painted a bright crimson red.

  It’s a good thing I live alone. Don’t want anyone to see me with these nails!

  THE EXPERIMENT

  CHAPTER VII: AFTER DARK

  He barely got any sleep at all that night. Reed tossed and turned in his bed, his mind racing. In the glow of the moon, he could see his painted nails. They were so smooth and shiny. Many times he caught himself staring at them, lost in their beauty and elegance. All his life his nails were poorly kept. He would bite and pick at his nails, leaving them jagged, short, and uneven. Never once did he polish them. Seeing them in this newly renovated state was strange.

  When he did manage to get some sleep, he dreamed about being a woman at a night club. He dreamt about wearing a short dress and high heels; the gaze of the men upon his smooth and sexy body, the lights of the dance floor shining down on his body. The mass of bodies on the dance floor closed in around him and before he knew it, there was a group of guys surrounding him, cutting him off from the outside world. One stood in front of him and danced, his body rubbing against Reed’s. The man’s hands grabbed Reed’s ass and playfully squeezed it.

  Another man stood behind him, and Reed was stuck in a manwich. The man in front of him grabbed and played with Reed’s breasts. The man behind him reached around the front and rubbed Reed’s thigh. His other hand moving slowly north. Reed could feel the man’s hot breath on his back, it was intoxicating. The three bodies moved in unison.

  The man in front of him gently pulled down the front of Reed’s dress, revealing his plump breasts. Beads of sweat glimmered in the neon lights. The man’s tongue licked and played with Reed’’s nipples. The man behind him slid his fingers into Reed’s panties, pulling them down.

  Reed did not resist. The man’s fingers slid into his pussy and Reed bit his lip. The man in front of him continued playing with his breasts while the man behind him finger fucked Reed.

  Their pace quickened and Reed’s body temperature rose as he climaxed, his pussy oozing their juices onto the man’s fingers. Raye moaned and Reed sprang up. Breathing heavily, he looked around. Relieved to find himself in his house and alone, Reed rubbed his head with his hands. His body was drenched in sweat and feeling wet in his crotch, he pulled his sheets aside to find his boxers stained with cum.

  He climbed out of bed and staggered to his bathroom. He turned on the lights and looked at himself in the mirror. His male self looked back at him from the reflection. He splashed his face with cold water from the sink and took off his boxers, draping them on the shower door. He turned off the lights and crawled back into bed, too tired to put on a clean pair of underwear.

  Closing his eyes, he looked at the clock. 4am. Sighing, he drifted off into a dreamless sleep.

  “I'm so excited for tonight! Are you excited Raye?” Arina stood in the doorway, waiting for her next client.

  “Sorta, Mistress.” He said, his eyes remaining glued to the screen. His dr
eam from the night before has been bothering him all day. He kept it to himself, and he tried to get his mind off of it by focusing on the job in front of him.”

  Arina could tell something was bothering him, but she decided to let it be. “Oh, don’t worry. After tonight, you’re going to be glad you went out! Now be careful not to break a nail while typing on the computer, ok?”

  “Yes Mistress.” As the hours went by, the paper pile diminished. Pretty soon all that was left were bills and other financial documents that needed to get filed.

  Then 8pm rolled around.

  The phone rang, the red light signaling the call coming from Arina’s office flashed. Reed pushed the speaker phone button. “Raye, I've finished with my last client, finish up what you’’re doing and meet me in my office.”

  “Yes Mistress.” He replied. He hung the phone up and got to a stopping point in his work. Finishing, he stood up and as he did, he realized that his skirt had gotten caught and it rode up on his legs, showing off the tops of his stockings and his panties. What made matters worse was that the client happened to walk by when that happened.

  Red with embarrassment, Reed apologized to the client.

  “Don’t be, you have nice legs.” He said, winking.

  “Thank you.” Reed replied, his face still red. He waited for the man to leave before having a panic attack.

  How embarrassing! Thank god I have this bodysuit on or else he would’ve seen my package!

  He fixed his skirt, locked the front door and headed upstairs. Reed opened the door to her office and caught her changing. “Oh, sorry Mistress, didn’t mean walk in!”

  “Nonsense, we’re both women here,” she joked. “It would be different if you were a man. Your stuff is in your locker, keep only your panties on, you won't need your bra or stockings.”

  Reed ignored the comment about him not being a man. He stripped off his clothes and put them in the basket. He unclipped his bra and removed his stockings and garter belt, placing them in the hamper too. He opened the locker and there it was: the blue dress, and right below it were the shoes. He took a deep breath and took it out. He slid on the dress, zipped up the back, and straightened it out, then he put on the heels, and fastened the straps. He turned and looked at himself in the mirror.

  God damn. Once again I’m looking at the kind of woman I’d want to pick up at a club. Why do I have to be that woman?

  “Looking good,” Arina said. He turned to thank her and froze in shock and awe. She was wearing a black and red leather mini dress.

  “You look amazing Mistress,” he managed to say.

  “Thank you Raye. Now come here, you need some last minute accessories.” He walked over to her, and since the heels were the same height, he had no problem walking in them. One thing he did notice was that the soft material of the dress was rubbing against his legs, and it felt like everyone could see his panties. She pointed to the vanity chair. He sat down and she began ruffling through some of the drawers.

  “Since you have that collar on, you don’t need a necklace, but you do need these.” She pulled out two earrings and clipped them to his ears. Then she gave him a gold bracelet and a ring. She also touched up his makeup with a nice layer of shiny lip gloss and a couple sprays of perfume. “All done, now, grab your purse and let's go clubbing!”

  And with that, the night officially began. He climbed into her car and they drove off. After a little while they arrived at the club. The entire car ride he tried to hide his nervousness, his thoughts constantly bringing up the dream from the night before.

  No matter what happens, I’m not going to lose myself in there.

  When they pulled up, Reed felt as though his heart was gonna burst out of his chest. Arina had the car valet parked and they walked towards the doors. Reed could feel the eyes of every man, and woman, on him. He bit his lip and tried to hide the nervous shaking in his legs. “Wow, that's a long line, you sure we’re gonna get in?” He asked, hoping she would give up and call it a night.

  “Of course. Raye, do you doubt your mistress?”

  “No Mistress.” He said quietly, hoping no one would hear him. They walked past the line and up to the entrance, where they were greeted by a big bouncer.

  “Hello Arina… and who is the brunette?” he said, pointing to Reed.

  “Oh she is with me.”

  The man looked hard at Reed.

  Oh god, he knows… he knows I’m a man. He’s going to call me out in front of all these people.

  “Alright, have a good time tonight ladies.” He removed the velvet rope and waved them in, smiling happily. Reed followed Arina up the stairs into the club. He heard complaints coming from the people in line, but they were silenced when the door closed behind him.

  He turned away from the door and stayed close to his mistress. The last thing Reed wanted was to get separated from her and be on his own. It was a large club, in the middle was a huge dance floor surrounded by lights. There was a long bar and many chairs and tables and an upstairs section that overlooked the bottom floor.

  “Come on!” Arina yelled over the music. She grabbed his hand and led him over to the bar, where they sat down. Reed’s eyes were everywhere. He death-gripped his purse and kept his body turned away from the viewing public.

  “What will it be ladies?” the bartender asked.

  “Jack and coke and a cosmo.” Arina replied, “Put it on my tab.”

  “Of course, Lady Arina.” The bartender said, shying away. Reed did a double-take between the bartender and Arina. She tapped her nose with her finger.

  “So, what do you think?” she asked.

  “It's pretty happening tonight, but I am very nervous,” Reed replied.

  “Don’t worry, once you get a couple drinks in you, all those worries will vanish and you’ll enjoy yourself.”

  Reed said nothing. The dream still lingered in his consciousness.

  “Here you go.” The bartender placed the two drinks on the table. Reed reached for the jack and coke, but Arina slapped his hand. She wagged her finger at him and grabbed the drink, leaving the cosmo for Reed.

  Shit. She is totally messing with me.

  She laughed as Reed sipped the cosmo.

  For a while they sat at the bar and chatted. Arina asked him about working for her and how he was doing. Then she asked him about being a woman and if he was enjoying that too. He replied and honestly said that each day it was getting easier and easier, and that it was also getting more and more interesting. Part of him was truly enjoying the experience, and another part was still uncomfortable about it.

  “Glad to hear it. Now if we can only suppress that male subconscious of yours, you’d have more fun… and so would I!”

  A couple drinks later and the alcohol was helping Reed relax.

  That’s when everything changed.

  The bartender placed another cosmo in front of Reed. “Here you go, from the man over there.” The bartender said, pointing to the man.

  Arina patted him on the back. “Wow, congrats Raye. The first time a man has ordered you a drink… and he’s cute too,” she said. He didn’t know how to reply. He looked over and saw the man. He was staring at him and looked as though he was checking Reed out. Reed blushed slightly at the embarrassment.

  “Oh my god, you’re blushing!” Arina said, laughing.

  “No I am not!” he replied, sipping the drink.

  “Don’t look now, but I think he’s coming over here.”

  “Shit, what do I do?!”

  “Act natural honey. Do what a woman would do.”

  “Thanks for the advice,” Reed replied sarcastically.

  He turned and the man was already next to him, the suddenness of his appearance startled Reed. “Oh, I'm sorry, I didn’t mean to scare you,” he said. “My name is David, but you can call me Dave.”

  Oh god, what do I do, what do I do?

  “Heh, don’t worry about it. I'm kind of a wuss,” Reed replied.

  The man laughed. �
�So what may I ask is your name?”

  Reed said nothing, and Arina immediately nudged him in the back.

  “Oh, sorry, my name is Re—Raye,” he said, extending his hand.

  “Nice to meet you Raye.” Dave replied, shaking his hand. “Care to dance?”

  Reed felt another nudge in his back.

  “Oh, yea, of course.” He said, scratching his head. Dave stood up, and stuck out his hand. Reed took a deep breath, and grabbed Dave’s hand. He helped Reed up and led him to the dance floor. As they were walking, Reed looked back to Arina, who set his purse and drink next to hers, and gave him a ‘thumbs up’. They went down the steps and went out on to the dance floor and Arina vanished behind the wall of people.

  Dave made his way through the crowd, keeping Reed close. He stopped at a clearing and began to dance.

  Ok Reed, you can do this. Just dance and maybe he’ll lose interest and find another chick.

  He started dancing. The DJ was playing a catchy electronic-dance song, and Reed tried his best to move with the music. He looked up and saw Dave was getting close to him. He looked again and saw that Dave was looking up and down, admiring Reed’s figure. Hoping not to meet eye to eye, Reed looked around at the crowd. All of the other girls were pretty much right on top of their guys. Some were facing each other, while others had their backs to them. He remembered that pretty much since high school, this is how couples danced at clubs. He turned back to Dave who was now looking into his eyes. Their gazes met and a switch flipped in Reed’s head. He put his hands in the air and turned around, allowing Dave to get right on his back.

  So this is what it’s like to dance as a chick.

  Dave put his hand on Reed’s hips and pulled him in closer. The two bodies appeared to have merged into one as they moved with the music. The two of them danced like that for the remainder of the unusually-long song. A mixture of the heat from all the nearby bodies and all the alcohol he had fogged his mind and his vision. Thanks to the catchy beat of the music, he danced more freely. He could feel beads of sweat form at his brow and slide down his neck and through his cleavage. Dave’s hands moved slowly, one went around Reed’s hip and onto his thigh. The other went up past his waist and up to his breast.

 

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