Lipstick & Miniskirts

by John Dylena

  “Say: ‘I’m such a slut.’ ”

  “I’m such a slut,” he replied softly, his voice weak and feminine. His body temperature rose and the women continued their erotic torment.

  “Say: ‘I love wearing fishnets and high heels.’ ”

  “I love wearing fishnets and high heels,” he repeated again, his voice louder. Oh god, I can’t stop.

  “Faster, Sapphire,” one of the women said. As he stroked, they sat him down on one of the couches. “Say: ‘I love wearing lipstick and I crave cock.’ ” The ladies looked at each other, waiting for him to say it. Some of them were so turned on by it they’d begun to play with themselves.

  “I love wearing lipstick… and I… crave… cock.” Girlish moans escaped his lips. They grew louder as his hand moved faster up and down his shaft.

  His hips jerked and a stream of cum erupted out of his dick as he cried out. The white fluid went everywhere, most of it landing on his stomach with some of the smaller globs landing on the couch. He breathed heavily, exhausted from the sexual ordeal.

  Amidst the sounds of his breaths and the other girls talking, he heard the familiar sounds of a camera. He looked up to see the woman who started this whole thing smirking behind her pink smartphone.

  “All right, Sapphire. Now you have to stay. If you try to skip out on your duties tonight or act out, these photos and videos hit the internet.”

  Scott looked around to see other women holding up phones as well. He discovered that he wasn’t the only one to get off. Some of the women had to change their panties after watching him.

  “Clean up your mess before it stains.” They handed him tissues and he obeyed, fearing their wrath now that they had evidence of his transgressions.

  I can’t believe that just happened. I can’t believe I actually said those things. He stood up and pulled down his skirt.

  “Have you ever worked as a waiter, Sapphire?”

  “Yes, I have,” he replied.

  “Hold up. You can’t talk like that. You have to talk like a woman. Now, say it again.”

  “Umm, yes, I have,” he said again with his best female voice. The women nodded.

  “Not bad. It could use some work, but the men out there will be too drunk to notice.”

  “It’s the same kind of thing, only the customers are drunk and horny. The better you serve them, the higher your tips will be.”

  “Yeah, don’t be afraid to get up close and personal. Men like it if you sit on their laps or touch them.”

  “If anyone gives you trouble, wave over Roger or one of his associates.”

  Scott froze. Roger. He had forgotten all about him.

  He turned to the doorway, and there he stood. He was watching me the entire time.

  Roger winked and Scott turned back toward the women. The announcer’s voice came through the speakers in the changing room.

  “That’s our cue. Sally here will take you out onto the floor and give you a quick rundown of procedure.”

  “We can’t wait for you to get back.”

  “Why? What happens then?” he asked.

  Becca grinned. “We dress you up for the stage!”

  Before he could reply, the crowd dispersed and Sally grabbed his wrist, pulling him out the door. Some of the women walked out onto the stage while Sally led Scott down the small staircase alongside the wall. In the dark corner of the club behind a privacy curtain, she gave him his instructions.

  “Okay, Sapphire, this is how it goes. Every waitress has a section, and this is yours.” She circled an area on the laminated floor plan with her finger. “This is different than a restaurant, because people are coming and going constantly and moving about the building. Your job is to make sure everyone gets a drink if they are over twenty-one. Walk up, introduce yourself and take their orders. Remember, we make most our money off of tips, so if you want to—”

  “Hey, Sally. Who’s this?”

  Recognizing her voice, Scott kept his back to Allie as she walked up to him.

  “Oh, you don’t recognize her?” Sally said with a smirk. Scott looked down at the ground as Allie stepped in front of him.

  “Oh. My. God. Is that…?” She turned to Sally, who nodded her head. “Hey, look at me!” Allie snapped her fingers in Scott’s line of sight and he slowly looked up at her. “Damn! Look at you. If I didn’t know better, I’d say this was your calling. Although, you could use bigger tits.”

  “Kerri and Bree overheard him saying how terrible the dancers are and how easy it is to dance. And after hearing what he said about you, they decided to bring him backstage and have him put his money where his mouth is.”

  “Will he?”

  “Yes, she will eventually go on stage.”

  Allie turned to Scott. “What’s your name?”

  Scott said nothing. He looked away out of embarrassment.

  Allie grabbed his chin and made him face her. “What is your name?”

  “…Sapphire,” he replied in his best female voice. Allie burst out laughing and was quickly joined by Sally.

  “That is precious. Sally, what section is she working tonight?”

  “She’s got section four.”

  Allie grinned. “We’ve got some rowdy customers there tonight. A little too touchy-feely.”

  “Allie! What the hell are you doing back here?” A guy in a nice suit walked up to the three of them. “Oh, hey, Sally.”

  “Hi, boss,” the two women replied.”

  “And who are you?” he said to Scott, looking him over with a playful smirk.

  “She’s a new girl. We’re giving her a test run to see if she can work here.”

  “What’s your name, beautiful?” He placed his hand on Scott’s cheek.

  “Sapphire.”

  “Well, Sapphire, let’s hope what you lack in a body you can make up for in customer service. Break’s over, ladies. People are thirsty.”

  “Yes Boss,” they said in unison. He looked the three of them up and down and left.

  “That’s Rick. He’s the owner,” Sally said to Scott. “Best not anger him. Good luck, Sapphire!”

  Before Scott could reply, she headed off, returning to the floor.

  Allie turned to Scott and pressed him against the wall. “Listen, ‘Sapphire’, you were a dick to me all night, and just because I have to play nice doesn’t mean you are forgiven.” She reached under his miniskirt and grabbed his junk. “If you don’t work your ass off tonight to make up for the poor treatment you gave me, I’ll make sure you’ll never want to step inside a strip club again.”

  She released her grip and her anger disappeared. In an instant, she was smiling and playful.

  “I’ll do my best, ma’am,” he said.

  “Good. Follow me. I’ll introduce you to your tables.”

  As they walked through the tables and past the booths, Scott kept his eyes on Allie, refusing to make eye contact with any of the patrons. He doubted they’d recognize him, as this was his first time visiting this club. Even though he didn’t look at them, he could feel the weight of their stares as he walked by.

  He kept his hands clasped in front of his skirt as he walked, ignoring the cat-calls he was getting, but he noticed that Allie would turn and smile at the men who called out to her.

  At last, they stopped at Scott’s first table.

  “Okay Sapphire, these four tables and those two booths are yours.”

  Scott eyed his section of the club. Two of the tables and only one of the booths had customers. Of those three, only one had drinks.

  “Good evening, gentlemen,” she said to the first table.

  “Why, hello, Allie!” the two men replied.

  “This is Sapphire,” she said, moving Scott in front of her. “She’ll be taking take of you for the rest of the night.”

  “Hello, gorgeous,” the man closest to Scott said. He grabbed Scott’s waist and pulled him onto his lap. Scott jumped when he felt a playful squeeze on his butt.

  “Hello,�
�� he said timidly. “I look forward to taking care of you tonight.” The man let Scott go and slapped his ass as he stood up. The two drunk patrons laughed as Allie led Scott onto the next table.

  A couple hours went by, and Sally came for Scott. He was relieved to see her waving him over. He gave the customers he was serving their drinks, smiling and thanking them as they slipped cash into his thong straps and skirt. Sally led him back to the dark corner behind one of the privacy curtains.

  “Look at you,” she said as she examined the cash tucked into his various pieces of clothing. “How did it go?”

  “It was difficult at first, but as time went by, it got easier. My legs are going to be sore tomorrow from walking in these heels all night.”

  “Well, the night isn’t over yet. You still have to go on stage.” She smiled as she grabbed his wrist and led him back into the changing room. The women giggled excitedly when they saw him return.

  “Here is an envelope to put your tips in. The locker at the very end has your stuff in it, and here is the key.” She handed him a white envelope and a brass key.

  He slipped the cash out of his clothes and stuffed it into the envelope, then put it in his locker. He turned around and saw all the women eyeing him. He felt like a zebra in a lion’s den. They all looked at him hungrily.

  “Time to get you changed!” They pounced on him, stripping him of the outfit he had on, tossing the items into the laundry baskets and leaving him standing naked in the center of the room. The women chatted as they planned his outfit.

  “Well, she can’t wear a thong on stage, ‘cause then everyone could see her junk.”

  “Yeah, it would be okay if tonight was a gay night.”

  “We could use latex panties. They’re snug and we can just tuck everything in.”

  “That’ll work.”

  With a consensus achieved, they went about dressing him up for his big stage show. They handed him a pair of red latex panties and he slid them on. The material was constricting, but with a couple adjustments, his manhood was hidden away.

  They wrapped a black lace garter belt around his waist and gave him black stockings to wear. They fastened the tops of the stockings to the clips, and he was given a pleated skirt as well.

  This skirt was even more revealing that the one he’d had on earlier. Instead of covering his legs, the fabric flared out sideways. All it would take was for him to turn too fast and his groin would be exposed.

  He was also given a red latex bra which matched the panties, and they stuffed it with not only the breast forms, but some stockings too, enhancing his bust.

  “We’re going to need to get you some bigger falsies.”

  Yeah, as if I’m ever coming back to this place, Scott thought dourly.

  He put on the button-down blouse and tied it as they requested. They redid his hair and makeup and gave him an extra coat of body glitter. They topped it off with a magnetic clip-on belly button ring. Sally gave him his shoes, the same ones he’d had on earlier, only the soles and straps were cherry-red to match the rest of his ensemble.

  “Okay, Sapphire. This is the big finale. You’re going to be on the left pole, facing the audience. Music will play and you must dance with it. Now, with this being your first time, don’t worry about doing fancy things with the pole. Just work the crowd. Find the people waving cash and dance close to them so they can tip you. You’ll be done when the music ends.”

  “Our last dancers for the night will be coming out shortly,” the announcer said over the PA system, “and we have a special treat for you all tonight. One of the dancers will be our newest addition: Sapphire!”

  Scott listened as people cheered. The two other women sharing the stage walked up to him.

  “Good luck, Sapphire,” they teased.

  Scott shivered as the announcer’s voice returned. “And here they come!”

  The two women walked out the door, and Scott felt hands pushing him forward. He left the changing room and followed the two women. The lights were bright and all eyes were on him. He walked down the steps and to his designated pole. Men were leaning on the stage looking up at him. Most of the crowd was gathered in front of the other two dancers.

  The music started. The song was simple enough to move to and he danced, trying to emulate what he remembered. All night while he’d been waiting tables, he had kept his eyes on the dancers, studying their movements and seeing what worked. He thought about what he would like to see a dancer do and he did his best to cater to the small crowd at his feet.

  He danced around the pole, moving his body in waves and sticking his butt out as he squatted. In the corner of his eye he saw a man waving cash at him. Scott walked toward the man and turned, squatting and sticking his ass in the man’s face. He felt the bills slide into his garter belt and he stood back up, moving and dancing for the man. Then the music shifted, and his routine changed with it.

  Time flew by, and before he knew it, the music had stopped.

  “And that’s it for tonight! Thank you, ladies!”

  Scott looked back to see the other women leaving the stage. He bent down and picked up his skirt and top, which had come off sometime during the show.

  It’s weird. I don’t even remember taking these off. Was I that into it?

  Scott followed the women into the locker room, where he was greeted by cheers and applause.

  “Nicely done, Sapphire. You looked like you were having fun up there.” Bree walked up to him and shook his hand. He walked through the crowd of women changing and stepped up to his locker. He unlocked it with the key he’d stored in his stocking-stuffed top and filled the envelope with the tips.

  “Hold up, Sapphire. You’re not allowed to leave just yet,” Allie said to him.

  He sat down on the couch and watched the women change. No one seemed to care that he was in there. They must’ve thought of him as one of the girls. It didn’t bother him. He got to see all these pretty ladies naked.

  One by one they left, until only Bree, Kerri, Allie, and Roger remained. Outside the locker room, the bouncers ushered everyone out and the place was locked up.

  Kerri turned to him. “Well, Scott, it seems you outdid yourself. I’d say you’re a natural.”

  “We did some background research on you while you were working tonight. It seems you just lost your job and you’ll lose your apartment if you don’t find one soon.”

  Scott watched as Bree opened his locker and took his envelope and counted the cash. “Three hundred and fifty dollars—not bad for a first-timer, and a man at that.”

  Wait, three hundred and fifty dollars?! That’s how much I used to make in a week!

  Bree smiled as she divided up the cash amongst Allie, Kerri, Roger, and herself. “It’s a shame you won’t get any of it. However, if you come back tomorrow night… say, seven p.m… and work for us again, you’ll get to keep what you earn. After the typical expenses, of course.”

  Bree took his phone out of his locker and programmed her number into it. “If you do decide to come back, give me a call no later than five p.m.”

  “See you later, Sapphire.” Bree and Kerri walked down the hallway, leaving Roger and Allie with Scott.

  “He looks pretty cute dressed like that, doesn’t he?” Allie said to Roger. “You see, I heard about the ‘fun’ you had before you started work, and I feel bad that I missed out. What about you, Roger?”

  “Left me with an itch that I’d like to scratch,” he said, his voice deep and menacing.

  “Tell you what, Scott. We’ll give you our share of the money you earned if you do us a solid.” Allie waved the stack of bills in front of him.

  “What do I have to do?”

  “Oh, you know what you have to do.” She pointed to Roger and Scott turned to see his pants coming off and his monster of a cock hanging free. He sat down on one of the couches and spread his legs, waving Scott forward.

  “Go on, Sapphire,” Allie said. “You want that money, don’t you?”

 
; Scott did need the money, and badly. He was behind on most of his bills, and he was on his second extension for his rent. If he didn’t give his landlord some cash soon, he’d be out on his own.

  He stepped forward and knelt down in front of Roger. His meaty shaft dwarfed Scott’s own dick, making his look like a cocktail weenie. Scott grabbed the man’s dick and stroked it, watching it harden as he played with it.

  The man’s aroma was powerful and Scott felt lightheaded. He grabbed the meaty pole with his other hand, and continued. Allie pushed his head forward and his lips pressed against Roger’s head.

  “Kiss it. Use your tongue,” Roger commanded.

  Scott kissed the head with his ruby red lips and caressed it with his tongue. He had never tasted another man’s dick before, but it was somehow familiar. He licked the bottom of the shaft as he slid down to Roger’s massive balls. Scott got a full whiff of Roger’s musk as he sucked on them. Just like what he did on stage, he reenacted what he remembered the women doing in the pornos he’s seen.

  He must’ve done something right, as Roger let out a groan of approval. Scott moved away from the scrotum and returned to the head. He wrapped his lips around it and slid down and pulled back. His lips came off the prick with a pop, and after a moment’s rest, he slurped the dick back into his mouth.

  Roger put his hands on Scott’s head, pulling him further down the shaft. He was halfway down when Roger let go, allowing Scott to pull free and catch his breath.

  “She’s good,” Roger said to Allie.

  “Keep going, Sapphire,” she ordered.

  Scott put Roger’s penis back inside and slid halfway down before pulling back and repeating the process.

  Remember, Scott: you’re doing this for the money, not because you enjoy it, he assured himself.

  He picked up his tempo as he bobbed up and down on Roger’s rock-hard penis. Each time he went further and further down, until he was sliding the entire dick in and out of his mouth. He breathed in through his nose to keep himself from passing out as he deep-throated Roger’s massive dick. Scott’s own prick grew hard in his latex panties as the blow job became more and more enjoyable.

  Roger moaned and groaned, blurting out compliments and expletives. “Oh! Oh, yeah, Sapphire! Suck it! Suck it, slut! Don’t stop!”