Lipstick & Miniskirts

by John Dylena

  “Oh… I see.”

  “If you choose to do so, you’ll have a special new body suit to wear. Which means that you’ll have to shave your arms and legs for they will not be covered by the material.”

  “I’m interested, but may I have some time to think about this?”

  “Of course you can. Either get back to me by the end of the day today or before noon tomorrow. Now back to work.”

  “Yes Mistress. Thank you Mistress,” he said, turning back to his lunch.

  When she left, he stopped eating. He leaned back in the chair and rested his legs on the desk.

  For a while, he just stared at the bottom half of his body; the skirt he was wearing, the stockings, the heels. He looked at his hands. His nails were still painted red, and in near perfect condition, considering all the typing he’s done. He put his legs back down, straightened his skirt, and crossed his legs. He continued eating his lunch, his mind debating the terms of the deal.

  Hours passed and after finishing another client profile, he stopped once again. Arina’s proposal echoed in his head and he couldn’t focus on the work in front of him. He thought about living an entire week in the body suit. What would happen if he lost the bet? What would Arina do to him? He’s heard and read stories about what dominatrixes had done to some men. What would happen if he won? What would he ask of her? Would he demand revenge for what she did to him the other night? Or worse, would he ask her to do it to him again?!

  Then an idea popped into his head and he knew what he was going to do.

  Challenge accepted.

  He picked up the phone and pushed the button, calling her. “Mistress?” He said, hearing the other end of the line pick up.

  “Yes, Raye?”

  “I've decided to accept your bet.”

  “Good, I’ll begin the preparations… now back to work.”

  “Yes Mistress.” He said, grinning.

  Journal Entry, Day 7:

  What a busy and eventful weekend. First: on Friday, Arina and I went to a club. I got drunk, danced with and eventually made out with a guy. I kissed a guy! Afterwards we got back to her shop and I still don’t remember what happened then, but the morning after gave me some good clues. I was wearing this ridiculous pink mini dress, like something a hooker would wear. Topped off with fishnets, pink leather lingerie (including a thong) and pink platform heels—oh and my ass was sore—apparently in my drunken state I asked the mistress to dress me like that then to fuck me. I'm glad I don’’t remember any of that.

  Whatever happened, she felt bad for what she did. She mentioned that it was because I wasn’t in my right mind, so she offered to make it up to me, by placing a bet: if I were to live and work as a woman for 24 hours for 1 week, she said I could do anything and ask anything of her. However if I somehow failed (I'm guessing by acting as a man) I had to be her client for a day. Who knows what will happen should I lose the bet?

  I decided to take her up on the offer, seeing as how for the past week I feel as though I've done a pretty convincing job. She hasn’t said anything or punished me since that one incident. Then again, she could just be doing that so I get too complacent and mess up. Man I'm paranoid! She did have some terms which I had to follow: she is getting me a new body suit and so I have to completely shave my body. I figured it would be the price I would have to pay during this little ‘experiment’, but oh well.

  Her shop is pretty busy on the weekends. One thing Arina failed to mention to me was that she had a fellow dominatrix come in and help her out so she can get a couple extra clients in there. I was constantly answering the phone and escorting her VIP clients to the lounge and printing out invoices and stuff. I noticed that a lot of her weekend clients were newcomers, most of them young guys, who looked awfully nervous—others not so much.

  Her dominatrix friend was named Susana, and she looked to be just a little bit older than Arina. I was introduced to her during the lunch hour and the whole time I wasn’t sure if she knew my ‘secret’’ .

  After she left on Sunday, I asked the mistress and she said Susana didn’t know the truth, but Arina did ask her what she thought of me. She said I looked “very beautiful, and was a stunning woman and she had no doubt in her mind that I was 100% born and raised a woman””

  That was the big confidence booster I need for the week long trial.

  Tomorrow I have to get up early so I can shower and shave.

  THE EXPERIMENT

  CHAPTER X: UNCHARTED TERRITORY

  The morning came quick and Reed sprung out of bed, eager to begin the week-long challenge. He jumped into the shower and shaved off his body hair. It wasn’t until he stepped out and dried himself off that he realized the consequences. First the painted nails and now the hairless body. There would be no way to defend himself should he run into someone he knew.

  It’s a good thing I don’t go out much.

  Arina was waiting in the lobby when Reed arrived. “Good morning.”

  “Morning Mistress.”

  “Ready for your big test?

  “Yes I am.”

  “Good, follow me.” When they arrived at her office, he was told at once to strip. “Arms and legs out!” He stuck them out and she thoroughly examined them, occasionally stroking her finger across his skin, as if searching for dust. “My, my, you did a fantastic job shaving, not a hair to be found. And I see you still have your nail polish on.”

  “Yes Mistress. I don’t know how to remove it.”

  She laughed. “Yes, that is a good thing. We don’t want you to remove it do we?” He shook his head no. “Well then, after we put your new body suit on, I’ll fix those nails right up.”

  “Oh, thank you Mistress.”

  She reached into the locker and pulled out the body suit. It was nearly identical to the previous one, except that the arms and legs were a lot shorter. Now he knew why he had to shave.

  “Put it on in the same fashion.” He did so effortlessly and slid the breast forms in their spots. He was about to head over to the vanity when she stopped him. “Because this suit is designed for more extended wearing sessions, certain parts of it have been slightly altered.”

  “How so?”

  “The rectum for one. The tube is a little bit longer and more flexible, so you need to do a little more adjusting.” He went to reach for a pen but she stopped him. “You have to use this.” She tossed to him a black rubber dildo, and he nearly dropped it like a hot potato.

  “Mistress, I have to use a dildo?”

  “It's a training dildo, and yes, now adjust!” He took a deep breath and bent over. He slid the dildo up his anus and could feel the material adjusting to his insides. “All the way in, and make sure you twist it around in there.” He slid the whole thing in and twisted it. When he was done, he tossed the vile object aside.

  “Now that wasn’t so bad was it?”

  “No Mistress, it wasn’t,” he lied.

  “Good, now sit down at the vanity. I have something special for you today.”

  Not another “surprise”.

  She pulled out a small box and opened it. Inside were a full set of false nails, painted red. She put them on his fingernails, and then painted his toe nails the same color. “Lovely, don’t you think? Now get dressed, your clothes are in your locker.” He stood up and went over to the locker and removed the shrink wrap packages. When he opened them up, he was surprised to see that his typical uniform wasn’t in there, but a completely different outfit.

  “Don’t worry, you’ll still have your normal outfit, but I wanted for you to wear this instead for today.” He gulped as he examined the contents: a black thong and garter belt, black fishnet stockings, red leather tube top and a black leather miniskirt. She handed him a shoe box and inside was a pair of red-leather thigh high 5” boots.

  She’s messing with me; trying to get me to fail.

  “You know, you could always give up. I’ll understand if you not woman enough to wear that.” She grinned.

  �
��You underestimated me, Mistress.” He said, smiling back. He got dressed, putting on the garter belt and stockings first, then the thong. Then he pulled on the tube top and mini skirt.

  Damn these are revealing. When I sit down at my desk, the skirt is going to ride all the way up!

  He sat down and slid on the boots, zipping up the backs. With the slutty boots on, he stood back up and walked over to the vanity. He put on his mask, the voice patch, his collar, and did his makeup.

  “Well then, I’d say you’re ready to get to work.”

  “I am, Mistress.”

  “Good, go downstairs an open up the shop.”

  “Oh my way, Mistress.” He went downstairs, unlocked the door and went back to his desk and sat down. The entire way he had to work to keep his balance. Even though the heel height was the same, the material went all the way up his thigh, restricting his movements. He felt like a robot with the way he was forced to walk. Sitting in the chair, he looked down at his skirt. His fears were coming true. The skirt rode up his legs when he sat down and the straps from the garter belt were in full view. Leaning forward an inch he could see up his skirt.

  He made a mental remainder to sit very close to the desk when clients were leaning on the wall talking to him.

  “Now Raye, your punishments are going to be more severe this week so don’t break any rules.” Arina said through the speaker phone.

  Worse? How could they get any worse than what you already did to me?

  “I won't, Mistress.”

  “Good, now get to work. My first client should be arriving shortly.” He adjusted his chair and began typing, crossing his legs in a feminine manner.

  I can feel my ass on this chair, and the thong keeps getting deeper into my crack. Every time I move, the fishnets and boots rub against my legs. It’s as if I'm getting turned on dressed like this. If this keeps up, I'm going to need a release.

  He picked up the phone and called Arina.“Umm Mistress?”

  “Yes, what is it Raye?”

  “What do I do if I need to you know… release some ... tension?”

  She laughed. “Is my little slut getting aroused from her outfit?”

  “No… Mistress,” he lied. He bit his lip and played with the phone cord.

  “Don’t lie to me. You’re allowed to ‘release some tension’’ but it has to be the way a woman does it.”

  “Does that mean?”

  “Yes, you have to either fuck yourself vaginally or anally with a dildo, no jerking off! Though it will be a huge chore for you to whip your dick out… still, no wanking! There should be a vibrator in one of the desk drawers, you can help yourself to it.”

  “Oh… ok, thank you Mistress.”

  “Enjoy.” She hung up the phone, leaving him hanging.

  Fuck… now what?

  He set the phone down and slowly opened the drawers until he found the dildo she mentioned. It was pink and about eight inches long. He sat there examining it, his full concentration on the toy. The phone rang, startling him and he dropped the toy on the desk. He grabbed the phone and answered it. The entire time he talked to the client, he didn’t take his eyes off the dildo.

  He scribbled down the appointment notes on a piece of paper, his eyes still glued on the object. The when client hung up, Reed finally took his eyes off of it and turned to the screen. He entered the details of the upcoming appointment into Arina’s calendar and kept his eyes on the screen. However, he could still see the pink dildo in the corner of his eye. Afraid that the toy would come to life and possess him, Reed quickly grabbed the dildo and put it back in the drawer and did what he could to keep his mind off of it while he worked.

  THE EXPERIMENT

  CHAPTER XI: POINT OF NO RETURN

  Several hours had passed since the inquiry with Arina and Reed’s situation hadn’t improved. He’d had too much coffee to drink which had led to him getting up to go to the bathroom often. Each trip both to and from the bathroom made matters worse.

  It wasn’t walking in the heels that complicated things; no after the first two trips, he had that down. What made things miserable was the fishnets that constantly rubbed against his smooth hairless legs. That, and the miniskirt that funneled air up to his crotch. The endless wedgie from the thong didn’’t help either. The tube top just enhanced his cleavage and made his breasts bounce with every step. The erotic build up in his body was reaching its boiling point, and he was about to blow like Mt. Saint Helens. He cursed his body for betraying him.

  I can't take it anymore, I need some release!

  He hurried back to the desk and sat down. Looking at the schedule, he realized it would be now or never. Arina’s next client shouldn’t be here for another hour and she was busy with a client at the moment. Any longer and he would have to remove the suit and jerk off, and if he did that, then the bet would be over. But if even if she caught him masturbating with a dildo and the source material being his own slutty appearance, then he would lose the bet. He needed to make it look like he was satisfying his “female” urges.

  Shit, what would be appropriate masturbating material for a woman? It would have to involve a man ... a magazine picture? Some image on the internet? Porn?

  He opened up the internet and looked for stuff to masturbate to. His body was squirming with nervous energy. He needed sexual release and he needed it now. His body betrayed him. Before he knew what was happening, he went onto a porn site and loaded a video of vanilla, heterosexual sex. He was breathing heavily and was starting to sweat as his fingers fumbled around the drawer. He grabbed the dildo and set it on the desk. He stood up, slid down his thong and rolled up his skirt and inserted the dildo into his ass.

  In the background he could hear the sounds of the porn; the man grunting, the woman moaning and letting out subtle screams of pleasure. The sounds echoed in his head as he slid the dildo in and out of his ass. In no time he had his heels on the desk, his feet spread-eagle, and the entire dildo sliding in and out of his ass.

  He switched on the vibrator and the pleasure from it exploded exponentially. Girlish moans escaped his lipstick-clad lips as the porn in the background filled his mind. He began envisioning himself being the girl getting fucked.

  “Ohhhh god yes,” he screamed. “Ohhh… ohhh…… … OHHHH!” He climaxed as his moans now echoed in the lobby. A white fluid escaped through the hole in his vagina. But he didn’t stop. The ecstasy was overwhelming and he continued to fuck himself in the ass while the porn went on.

  He started hearing voices in his head.

  That's it slut, take it… scream you little whore… beg for more… ahh yea……

  “Ohhhhhhhhhhhh yes, yes, YES!” He screamed. “Fuck me harder.” He continued to slide the dildo in and out of his ass as another stream of cum oozed out. “Oh god yes, harder, harder,” he said. He pulled the dildo out of his ass and slid it into the vagina. It became coated in his white man juice as he fucked himself more.

  Lost in the erotic cloud, he didn’t realize he had a guest. “Enjoying yourself?” the voice said. It took a second for him to register it, then it hit him like a ton of bricks. He pulled the dildo out and it slipped out of his fingers and landed on the floor. Then his ass slipped out of the chair and he fell, landing on his side. He opened his eyes to see a pair of black leather boots. He slowly followed them up to see Arina smiling down at him.

  “Oh my god, what was I doing?!”

  “By the looks of it, having a good time.”

  He was red with embarrassment. “How long have you been watching?”

  “Not long, but I could hear you in my office, now tell me—” she said looking at the screen, “which role were you imagining yourself in?””

  “The… the… ”

  “The?”

  “Woman’s.” He said truthfully. He couldn’t believe what had happened. How carried away he got. She must’ve spiked the coffee with aphrodisiacs or something.

  “Thank you for being honest, besides I would’ve known y
ou were lying.”

  “How so?”

  “Let me quote… ” She said clearing her throat, “Oh yes, fuck me, fuck me harder!”

  Reed said nothing, but the sheer embarrassment of getting caught with a dildo up his ass, begging to get fucked harder was too much for him. He stood up his legs shaking, and collapsed in the chair from exhaustion. Broken and defeated, he broke out in tears.

  “Now now, Raye, there's nothing for you to get upset about.”

  “Yes there is Mistress. I'm a man, a man damn it, and here I am, dressed in this slutty get up, fucking myself with a dildo!”

  “Ahh, but you aren’t a man.” She pointed to a mirror, “I don’’t see a man, do you?”

  Reed looked at his reflection in the mirror. He saw no man staring back at him, just a woman in an incredibly provocative outfit. “No Mistress.”

  “Then why are you getting so upset? Women all over the world do what you just did.”

  “But… but… ”

  “No buts. Now, if you were here, in this same situation, but dressed as a man, than you should be upset.” What she just said made perfect sense, but it still upset him. “Look Raye, when you’re here, in the guise of a woman, you have to do womanly things. If you were a man, you would be doing manly things… understand?”

  “Yes I do Mistress, but still, underneath it all, I am a man.” He continued to cry.

  She placed her hand on his shoulder. “At times I may look like a woman, but inside I feel like a man. When I'm dominating someone, I feel all tough and manly inside, but I don’t let that bother me. So when you’’re en femme, you shouldn’t let womanly things bother you.”

  “I see your point, Mistress. I guess I just let myself get carried away.”

  “Yes you did. I have never seen someone masturbate that intensely before. Now, I have an idea for you. What would you say to some real cock?”

  “What?!”

  “Real cock. How would you like to get fucked by a real man, not one that you see on the screen or a toy?”