Lipstick & Miniskirts

by John Dylena

  He’s feeling me up! And why am I not disgusted?! Am I… am I enjoying getting felt up? I… I must not let this get out of control.

  He separated his body from Dave’s and turned around to face him. He grabbed Dave’s arms and placed them on his hips and he put his arms around Dave's shoulders. Thanks to the heels he was wearing, Reed was almost as tall as him.

  Dave slid his hands further south, stopping above Reed’s butt. Dave pulled Reed closer to him and he could feel Dave’s hot breath on his face.

  Well, that didn’t help either, now I'm face to face with him. At least his breath doesn’t smell bad.

  Dave looked down into Reed’s eyes and smiled, and Reed smiled in return. Then it happened: Dave leaned forward and kissed Reed.

  Oh shit! Need to think, I got to—

  His train of thought was cut off as his body reacted on its own: by kissing Dave back.

  What is happening to me! I'm kissing a cute guy, wait did I just say cute again?! But I'm not a woman, I am a man… a man… a—oh fuck it, I'm a god-damn woman tonight!

  Raye continued kissing Dave, going further with the addition of tongue. After what seemed like an eternity, they separated.

  “You’re a good kisser,” he said.

  “Thank you,” she replied.

  “I had a really good time with you tonight.”

  “So did I.”

  “Here, call me sometime.” He said, handing Raye a business card.

  “Thanks.” Raye tucked the card into her cleavage.

  “No, thank you,” He replied. He gave her a quick kiss on the cheek, and left the dance floor. The switch flipped back. Dumbfounded at what just happened, Reed headed back up to the bar. Arina was still there, chatting up some guy.

  “Bartender, shot of whiskey!” He said.

  “Coming right up miss.”

  “So, how was your first kiss?”

  “Magical… wait, no, it was horrible. I kissed a man for Pete’s sake!”

  “From my point of view, you looked like you enjoyed it and hell, you should’ve seen yourself dancing… you were wonderful.”

  “Yeah, I didn’t know I could dance like that,” he said drinking the shot. “Another.”

  “Coming right up.”

  “It was strange. There I was dancing with this guy. I looked around and saw all the other girls dancing there, and then bam, it was as if Raye just switched on, taking full control… it was weird.” He took another shot. “And with that music, the booze, and that god damn heat, I just lost myself, I mean, look, I'm all sweaty!”

  “Yea, you do reek of BO. Let's get out of here… back to my place. You ready to go?”

  “Yes,” he said, finishing the last shot. “Thanks barkeep.” he said, now drunk.

  “Have a good night miss.”

  Arina helped Reed up, gave him his purse and they left the club. They stepped outside and the cool night air was refreshing.

  “Ahh, that feels good. It’s like 400º in there.” The valet returned with Arina’s car and they drove off, arriving at the dungeon in no time. They got out and headed inside. They went to her office and Reed sat down on one of the chairs. Arina opened her locker and began to undress. Reed turned and saw her standing there in nothing but lingerie. In an alcohol-induced fit of confidence, He stood up and walked up to her.

  “What do you want Raye?” she asked.

  “This.” He grabbed her head and kissed her. Seconds later the scope of what he did hit him. “Oh crap, I'm so sorry Mistress! I didn’’t mean to.”

  “You know Raye, you’re quite the little tramp. First you make out with a guy at the club and now you’re kissing me.” She said, wiping her mouth.

  “I'm sorry, Mistress, I'm sorry.” Reed said, backing up into the corner.

  I’m in deep shit.

  “Raye! Take off your shoes and your dress and hang it up,” she ordered. “I’ve been waiting for you to slip.”

  “Yes Mistress.” He quickly unzipped the dress and slid it off, hanging it up in his locker and setting the shoes on the bottom. Now he was standing there in nothing but his panties and the collar.

  “You’ve been a bad girl and now you need to get punished.”

  Oh crap.

  “Downstairs, now!” He turned and ran out the door. He went down the stairs and waited in the lounge area. “Go through that door and go down the hall to the red door and wait there.” He opened the door behind him and maneuvered through the short hallway and stopped next to the big red door. He waited there for several minutes, wondering where Arina was. Then he saw her turn down the hallway. She was dressed in her dominatrix outfit. She opened the door and motioned for him to go in. Inside was a vast assortment of machines, torture equipment, leather straps, chains…… the whole shebang. She walked over to a closet and opened it up.

  “Come here,” she ordered. He ran up to her and waited. “I'm going to give you some clothes, and you’re gonna put them on, no questions asked, got it?”

  “Yes Mistress.” She nodded and reached into the closet. The first thing she pulled out was a pink leather corset. She slid it on him and fastened the back. It squeezed his body, giving it a more defined hourglass curve, as well as enhancing his cleavage.

  “Take those panties off.” He did and set them aside. She handed him a pair of white fishnet stockings and ordered for him to put them on. After he put them on she handed him a pink leather thong, which he immediately put on.

  “The best part,” she smiled.

  She then pulled out a pair of pink, 6” heels with clear soles. Stripper heels. He slid them on and fastened the buckle. At first he wobbled thanks to the added inch, but he managed to gain his balance. She pulled out a pink mini dress, which was made of very thin and stretchy material. So when he pulled it down, it barely covered his ass. It had long sleeves and at the each wrist as well as at the hemline there was pink fuzz.

  “Almost done. Looking good slut.”

  Reed said nothing.

  “I said, looking good slut!”

  “Thank you Mistress!”

  “You’re damn right whore. Now close your eyes for a couple of seconds.” When he was given the go-ahead to open them, he was confused because nothing was different about her. But then he looked down. Arina had put on a strap-on dildo. “Seeing as to how you easily let a guy dry-hump you on the dance floor, then you swallowed his tongue, and then you tried to make a move on me, I'm guessing you’re one hell of a slut. And sluts like you deserve what they crave so they learn the consequences, you understand?”

  “Yes Mistress.” Reed was scared shitless, but there was something about her presence. He wanted to run away, but he stayed and obeyed her every command. He needed to be punished.

  “Good, now walk on over to that horse.”

  “Yes Mistress.” He turned and walked away.

  “Wiggle your butt you tramp!” She slapped his ass with a riding crop. He squirmed and made sure to wiggle his butt as he walked through the room. He arrived at the horse and turned to look at Arina. “Bend over it.” He gulped and bent over it. She walked over and fastened his heels and wrists to the machine.

  “You ready to get fucked whore?”

  He gulped. “Yes Mistress.”

  Not like this… not like this.

  “I’ll bet you are.” She lubed up the dildo and lifted up the bottom of the minidress. She pulled down the pink thong and played with his ass. After teasing him for a couple of seconds she slid the dildo in.

  Reed yelped, and she pulled out. “What a tight little pussy we have here.” She put the dildo back in and began sliding in and out, going deeper and faster each time. In no time she was thrusting the whole thing in, and continued to go faster. Amidst the sounds of bodies slapping into each other, Reed moaned and groaned.

  “Ohhhhh yes,” she yelled, tilting her head back. Reed continued to moan. “You like it bitch?”

  “No-OOO!” He said, trying to fight it.

  “No?! it sure sounds like
you do.” She squeezed his ass as she continued fucking him.

  I can’t think straight… it’s too much…

  “I… I… ”

  “Say it,” she ordered.

  “I… do.” He replied.

  I can’t fight it any more. It feels too good…

  “What?” She grabbed his hair, pulling his ear to her mouth.

  “I like it!” His jaw went slack and his tongue hung loose.

  “Say it!”

  “I like getting butt-fucked!” He gripped the supports of the horse as the tone of his voice shifted.

  This is amazing… I… I love being fucked like a girl!

  “What is your name?”

  “My name is… Reed.”

  “Wrong!” she said, slapping his ass.

  “Ohhhhh,” he grunted.

  “What is your name whore?”

  “Raye.”

  “And what are you Raye?”

  “I'm a slut.” His total submission sent him over the edge. His body was swimming in erotic ecstasy. His mind went blank as he felt his dick throb and pulse. He orgasmed, and a flood of white fluid leaked out his vagina. At the same time Arina screamed, her desire sated, or so he thought. She pulled the dick out of his ass and walked in front of him. His eyes followed the black rubber dick as it bounced. He craved it like a dog craves a bone.

  “Not done yet.” She opened his mouth and slid the dildo in. “You like the taste of cock?”

  “Mmmmmmrmmm,” he mumbled.

  I do… I love it.

  “What?” she said, pulling out.

  “Yes Mistress!” She stuck it back in and continued.

  After sometime, she pulled out. Reed was exhausted, breathing heavily. Arina uncuffed him and helped him stand up, putting him next to a chair. She sat down and pulled Reed in front of her. She guided him down onto her and she aimed her dildo into the false vagina. It entered the cavity and Reed rode Arina in the cowgirl position.

  Arina flipped a switch, turning on the vibrator. Both were moaning in pleasure. Reed came again as he continued to ride Arina’s cock. Arina grabbed him, stood up and laid Reed down on a nearby table. Arina climbed on top of him and he wrapped his legs around her as she continued to fuck him.

  After several minutes, she pulled out, turned off the vibrator and helped Reed up. He had no strength left and she had to do all the work. She helped him back up the stairs and into her office where she laid him out on the couch. She took off his heels tossed them aside. Reed instantly passed out from exhaustion, and Arina didn’t last long either. She left the office and went downstairs, falling on a couch. She drifted off to sleep, wondering what tomorrow would bring.

  I broke him. I turned him into a slut. If I’m lucky and he wakes up back to his old self, he’ll leave and never come back. Not after what I did to him.

  She felt a tear slide down her cheek.

  I liked having him around.

  THE EXPERIMENT

  CHAPTER VIII: LIES AND PROMISES

  Saturday morning came quickly and Reed woke with a massive hangover. He sat up on the couch and rubbed his throbbing head. He kept his eyes closed, cursing the bright fluorescent lights in Arina’s office.

  I must’ve been too drunk to drive home so she let me sleep in her office.

  Arina opened the doors to her office and walked in, wide awake and ready for the day. “Morning! Would you like some coffee for that hangover?”

  Reed stretched out his hand towards her. “Yes please.” He opened his eyes and looked around. He stood up off the couch when she walked up to him with the coffee and he noticed he was still dressed. ““Wait what? Why am I still dressed?” He looked down and saw the pink dress and the white fishnets. “What the hell happened last night?”

  “What?” Arina pretended to be clueless. She remembered every detail of what went down the previous night. She remembered how in his drunken state he tried to kiss her. She got angry and took it out on him, dressing him like a whore and fucking him until he passed out. It wasn’’t until afterwards did she realize the mistake she made. It wasn’t all his fault he’d kissed her. All week she had been teasing him sexually and with the outfit she had on last night, it was a miracle he didn’’t try to rape her.

  I did go overboard last night. I hope he’ll still want to stay here with me.

  “Why the hell am I dressed like this? And why is my ass so sore?”

  “You don’t remember?”

  Reed scratched his head, realizing he still had the mask on. “No, but I do remember having a lot to drink.”

  She sat down on the couch, debating whether to tell him. “Well what do you remember?”

  “Last thing I remember was us leaving the club last night, everything else since then is well, black. I got nothing from that point on.” Arina shrugged. “Can you tell me why I'm dressed like this?”

  Do I lie? Or do I tell him the truth?

  “Yes, I can… you were well, drunk and when we got back here last night, you insisted on wanting to try on something a little more, kinky.”

  “What? Really?” He looked at her in disbelief.

  “Yea, you picked that outfit out yourself. The heels are over there,” she said pointing to the corner.

  “I wore those?!”

  “Yes you did. You moved quite well in them too,” she said, giggling.

  “Ok, then why is my ass so sore.” Reed still wasn’t convinced.

  Shit.

  She perpetuated the lie. “You fell down the stairs… and landed on a dildo.”

  “Oh… wait what!?!”

  “Ok fine, you didn’t fall down the stairs. You found a strap on and got a little carried away.”

  “And you did nothing to stop me?”

  “You asked for it.”

  “I asked you to fuck me in the ass?!”

  “Yes.”

  “Wow, I must've had A LOT to drink… ”

  She had to change the subject. The train was starting to derail and it crashing would be catastrophic. “Do you remember kissing the guy at the club?”

  “That I do remember. What have I done… what have I become?” He paced around the office, rambling to himself.

  “The answer is simple: you wanted to experience life as a woman. You’ve kissed a guy and you’ve been fucked in the ass; that covers the intimate part.”” Reed fell onto the couch, mentally exhausted. Everything was moving too quickly and it was getting out of control.

  “Well, to be perfectly honest, if you would’ve continued to work for me for another week, I would’ve introduced you to those things.””

  “Well the thing is, is that I actually planned on working for another week, but now… ”

  Arina was devastated. She knew this was coming. This was what happened when you forced a client, when you continued to push in a direction they didn’t want to go in. She hadn’t had a client get this upset with her since back when she first started. She was inexperienced and wanted to jump into the deep end early. She knew Reed wanted to take it slow and to do things at his own pace. She’d pushed him forward and he wasn’t ready. “Look, I want you to work for me. It’s been a ton of fun. You’ve made things run a lot smoother here, and well, I really like having you around.””

  Thats it, cards are on the table.

  He sighed. “Yea, but I'm guessing next weekend won’t go the way you planned it.”

  “Don’t worry, next time that happens, it will be purely your choice to do so. 100% sober of course.”

  “I don’t see that happening for a long time.” He said standing up. He was still mad at her for what she did to him, but he still wanted to continue working for her. ““I do like it here, and I like working for you. This has been an eye-opening experience for me.”

  “Will you continue to work for me?”

  He looked at her, the anger gone from his eyes. “Yes… as long as you keep your promise.”

  “Of course.” She held out her hand and they shook hands in agreement. “Thank
you. Don’t forget though, your shift starts in an hour. Better get yourself cleaned up and changed, Raye.”

  “Yes Mistress.”

  THE EXPERIMENT

  CHAPTER IX: CHALLENGE ACCEPTED

  The day passed by uneventfully. After their discussion that morning, Reed quickly changed into his usual uniform. He fixed his makeup and added an extra couple of puffs of perfume to cover up the smell from the events of last night. If any of the clients could smell his odor through the layers of perfume, none of them showed any signs of it. However, he did forget that the perfume was laced with small amounts of pheromones, and he did get a couple of glances that bordered on lustful stares.

  Lunch came with Reed leaving to go to a nearby restaurant to get some to-go boxes. It wasn’t until he got back that he realized that he just went out into the world solo en femme and didn’’t think twice about it. As he ate, his mind drifted. He was staring into space munching on a salad when Arina walked into the lobby. She leaned on the desk and her sudden appearance startled him.

  “Look, I've been doing some thinking Raye.”

  “What is it Mistress?” He swallowed the mouth-full of greens and focused on her.

  “I feel bad for what I did to you last night and I’ve decided to make it up to you.”

  This should be interesting.

  “How so?”

  “I want to make a bet with you.”

  “What did you have in mind?”

  “Starting Monday, if you decide to live as a woman full time—24 hours a day, for 1 week—I will allow you to do anything to me or ask anything of me, as long as its within my capabilities, both financial and physical, and legal.”

  “Anything?”

  “Anything.”

  “What is the catch?”

  “Should you fail, at the end of the week you will be my client for a day. You come in here dressed as your male self and I get to do whatever I want to you.”